Indian Patents
Title of Invention

COSMETIC PREPARATION COMPRISING MEROCYANINE DERIVATIVES
Abstract Disclosed is the use of merocyanine derivatives of formula (I) for protecting of human hair and skin against the damaging effect of UV radiation.
Full Text Alkyl istfor example methyl, ethyl, n-propyl, isopropyi, n-butyl, sec-butyl, isobutyl, tert.-butyl, n-pentyl, 2-pentyl, 3-pentyl, 2,2-dimethylpropyl, n-hexyl, n-octyl, 1,1,3,3-tetramethylbutyl, 2-ethylhexyl, nonyl, decyl, n-octadecyl, eicosyl ordodecyl.
Alkenyl is for example straight-chain C2-Ci2alkenyl or preferably branched C3-C12alkenyl. Ci-C12alkyl, like vinyl, allyl, 2-propen-2-yl, 2-buten-1-yl, 3-buten-1-yl, 1,3-butadien-2-yl, 2-cy-clobuten-1-yl, 2-penten-1-yl, 3-penten-2-yl, 2-methyl-1-buten-3-yl, 2-methyl-3-buten-2-yl, 3-methyl-2-buten-1-yl, l,4-pentadien-3-yl, 2-cyclopenten-1-yl, 2-cyclohexen-1-yl, 3-cyclo-hexen-1-yl, 2,4-cyclohexadien-1-yl, 1-p-menthen-8-yl, 4(10)-thujen-10-yl, 2-norbornen-1-yl, 2,5-norbomadien-1-yl, 7,7-dimethyl-2,4-norcaradien-3-yl oder die verschiedenen isomeren von hexenyl, octenyl, nonenyl, decenyl oder dodecenyl.
C3-Ci2cycloalkyl is for example cyclopropyl, cyclobutyl, cyclopentyl, trimethylcyclohexyl or preferably cyclohexyl.
C7-C18aralkyl is for example benzyl, 2-benzyl-2-propyl, p-phenyl-ethyl, 9-fluorenyl, a,ot-di-methylbenzyl, co-phenyl-butyl, co-phenyl-octyl, co-phenyl-dodecyl oder3-methyl-5-(1\1',3\3'-tetramethyl-butyl)-benzyl.
(CrC^alkylidene is for example methylene, ethyl-1-ene, propyl-2-ene.
C6-Ci4ayrl is for example phenyl, naphthyl, biphenylyl, 2-fluorenyl, phenanthryl, anthracenyl
orterphenylyl.
d-Ci2heteroaryl is an unsaturated or aromatic radical having 4n+2 conjugated rc-electrons, for example 2-thienyl, 2-furyl, 2-pyridyl, 2-thiazolyl, 2-oxazolyl, 2-imidazolyl, isothiazolyl, tri-azolyl, tetrazolyl or another ring system from thiophene-, furan-, pyridine, thiazol, oxazol, imi-dazol, isothiazol, triazol, pyridine- and benzene rings, which are unsubstituted or substituted by 1 to 6 ethyl, methyl, ethylene and/or methylene, like benzotriazolyl, bei N-heterocycles optionally in the form of their N-oxides.
C2-Ci6heteroaralkyl is for example d-C8alkyl substituted with CrC8heteroaryl.
Preferably compounds of formula (1) are used,w herein Q is -OH; -OR7; -NR7R8; or -N=R9;

T is -COR5; -CN; or -S02-(C6-C12)aryl;
R-, is hydrogen; -OR7, -SR7; -NR7R8; C1-C22alkyl; C2-C12alkenyl; C2-Ci2alkinyl; C3-
C12cycloalkyl; C3-Ci2cycloalkenyl; C7-Ci2aralkyl; d-C12heteroalkyl; C2-C11heteroaraikyl;
C6-Ci0aryl; or Ci-C9heteroaryl; R2 and R3 independently from each other are C C12cycloalkyl, C3-C12cycloalkenyl; C7-C12aralkyl; CrC12heteroalkyl; C3-C12cyclohetero-
alkyl; C2-Cnheteroaralkyl, C6-Ci0aryl; or d-Cgheteroaryl; R4 is cyano; COR7f COOR7; CONR7R8; S02(C6-C12)arylr C2-C12alk-1-enyl; C3-C12cycloalk-1-
enyl; C2-C12alk-1-inyl;, C2-Ci2heteroalkyl, C3-C5heterocycloalkyl, C6-C10aryl; orCr
C9heteroaryl; R5 is -COR7; -COOR7; -OR7; -SR7; -NR7R8; CrC22alkyl; C2-C12alkenyl; C2-C12alkinyl; C3~
Ci2cycloalkyl; C3-C12cycloalkenyI; C7-C12aralkyl; Ci-C12alkylphenyl; CrCi2alkoxy-C6-
Ci0aryl; CrC12heteroalkyl; C2-Cnheteroaralkyl; C3-Ci2cycioheteroalkyl; C6-C10aryl; Cr
Ci2alkoxy-C6-Cioaryl or CrCgheteroaryl; R6 is CrC22alkyl; CrC22alkoxy; or COR7; R7 and R8 independently from each other are hydrogen; Ci-C22alkyl; C2-C12alkenyl; C2-
C12alkinyl; C3-Ci2cycloalkyl; C3-Ci2cycloalkenyl; C7-C12aralkyl; CrC12heteroalkyl; C2-
Cnheteroaralkyl; C6-Ci0aryl; o-C6-Ci0aryI; or d-Cgheteroaryl; R9 is a (CrCeJalkylidene radical; or Ri and R2, Ri and Q, Ri and R4, Ri and R6, R2 and R3, R3 and Q, R6 and Q, T and Q, each
independently, are linked together, so that 1, 2, 3 or 4 carbocyclic or N, O and/or S-
heterocyclic rings are formed, wherein each of them, independently from each other,
may be condensed with an aromatic or heteroaromatic ring, and/or more N-, O- and/or
S-heterocycic rings, and each N atom in a N-heterocyclic ring may be substituted by
CrC22alkyl; and n is 1.
More preferred is the use of the compounds of formula (1), wherein
Q is-OH;-OR6; or-NR7Rs;
T is -COR5 -CN; or -S02-(C6-C12)aryl;
RT is hydrogen; -OR7, -SR7; -NR7R8; CrC22alkyi; C2-C12alkenyl; C2-C12alkinyl; C3-
C12cycloalkyl; C3-Ci2cycloalkenyl; C7-C12aralkyl; or C6-C10aryl; R2 and R3 independently from each other are CVC^alkyl; C2-C12alkenyl; C2-Ci2alkinyl; C3-
C12cycloalkyl; C3-C12cycioalkenyl; C7-Ci2aralkyl; or C6-C10aryl;

R4 is cyano; -COR5, -COOR7; -CONR7R8; -S02(C6-Ci2)aryl; -CrC22alkylcarbonylamino-C6-C10aryl; or C6-C10aryl;
R5 is -COR7; -COOR7; -CONR7R8, -OR7, -SR7, -NR7R6, C1-C22alkyl; C2-C12alkenyl; C2-C12alkinyl; C3-C12cycloalkyl; C3-Ci2cycloalkenyl; C7-Ci2aralkyl; C6-C10aryl; orCr C12alkoxy-C6-C10aryl;
R6J R7 and R8 independently from each other are hydrogen; Ct-C22alkyl; C3-C12cycloalkyl; C3-C12cycloalkenyl; C7-C12aralkyl; or C6-Ci0aryl; or
RT and R2, Ri and Q, Ri and R4) Ri and R6, R2 and R3, R3 and Q, R6 and Q, T and Q are linked together pairwise, so that 1, 2, 3 or 4 carbocyclic or N-, O- and/or S-heterocyclic rings are formed, wherein each of them, independently from each other may be con¬densed with an aromatic or heteroaromatic ring, and/or more N, O and/or S-heterocycic rings, and each N atom in a N-heterocyclic ring may be substituted by CrC22alkyl.
Even more preferred is the use of the compounds of formula (1), wherein
R atom form an alkylene radical which my be interrupted by one or more -O- and/or -NR7-
or may be condensed with an aromatic ring; and R7 is Ci-C22alkyl; C3-C12cycloalkyl; C3-C12cycloalkenyl; C7-C12aralkyl; or C6-Ci0aryl.
Most preferred is the use of the compounds of formula (1), wherein Rt is hydrogen.
Furthermore, the use of compounds formula (1) is preferred, wherein
R2 and R3 independently from each other are C^Csalkyl; phenyl-CrC3alkyl; hydroxy-Cr
Ci2alkyl; or R2 and R3, or R2 and R4, or R2 and Q together with the linking nitrogen atom
form an alkylene radical which my be interrupted by one or more -O- and/or -NR7- or
may be condensed with an aromatic ring; and R7 is CrC22alkyl; C3-d2cycloalkyl; C3-Ci2cycloalkenyl; C7-Ci2aralkyl; or C6-C10aryl; And most preferably the use of the compounds of formula (1), wherein R2 and R3 independently from each other are C^Csalkyl; or R2 and R3 together with the
linking nitrogen atom form a C2-C4alkylene radical which may be interrupted by -O- or
-NR7; and R7 is hydrogen; or CrC5alkyl.

Preferred is also the use of compounds of formula (1), wherein
R4 is -COR5; phenyl, which is optionally substituted by CrC5alkyl; -CN; or -SO2-(C6-C10)aryl;
or R4 and T together with a bivalent C3-C7alkylene radical which my be interrupted by one or
more -O- and/or -NR7- form a carbocyclic ring which may be condensed with an
aromatic ring; and R7 is hydrogen; or d-Csalkyl.
Furthermore the use of compounds of formula (1) is preferred, wherein R4 is -CN; or COR5; R5 is CrCi2alkyl; or CrC12alkoxy; or R4 and T together with the bivalent radical of the formula o

(1a)

u , wherein

o
Ui and U3 independently from each other are a radical of formula -CHR7; -NHR7-; or -0-;
U2 is -CH2; or -CO-; or the direct bond;
R7 is hydrogen; or CrC^alkyl; form an aromatic ring.
Most preferred is the use of compounds of formula (1), wherein


T and R4 together with the bivalent radicals selected from

T R,

T R.

O

v
O

>=c;
NH






o
T R,


O
Q
o
/
M *
o
N

0 0 O

form a heterocyclic

ring.
Furthermore, the use of compounds of formula (1) is preferred, wherein R6 is hydrogen; CrC5alkyl; CrC5alkoxy; -O-(C6-C10aryl); or

R6 and Q together with a bivalent C3-C7alkylene radical which may be interrupted by one or more -O- and/or -NR7- or may be condensed with an aromatic ring, form a heterocyclic ring; and
R7 is hydrogen; or dC^alky!; and most preferably wherein
R6 is hydrogen.
Furthermore, the use of compounds ofse according to any of formula (1) is preferred,
wherein
T is -CN; -COR5; or -S02-phenyl;
R5 is CrC5alkyl; CrCsaikoxy; or NR7R8;
R7 and R8 independently from each other are hydrogen; or CrC5alkyl; or
T and Q together with the bivalent C3-C7alkylene radical which may be interrupted by one or more -O and/or -NR7- or may be condensed with an aromatic ring, form a heterocyclic ring; and most preferably the use of compounds of formula (1), wherein
T is -CN; or -COR5; and
R5 is CrC5alkyl; or CrC5alkoxy.
Furthermore, the use of compounds of formula (1) is preferred, wherein
Q is hydroxy; d-C5alkoxy; or-NR7R8; and
R7 and R8 independently from each other are hydrogen; CrC5alkyl; or phenyl, which may be
substituted by one or more CrCsalkyI or d-C5alkoxy groups; and most preferably,
wherein Q is hydroxy.
Furthermore, the use of compounds of formula
Ri 9 (2) 2^N' ^r ^K ^u is preferred, wherein
U4, U5, U6, U7 and U8 independently of each other are -CHR5-; -CO-; -NR7-; -CS-; or -Os
R5 is hydrogen; or CrC5alkyl; and
Ri. R2, R3, R6, R7 and Q are defined as in formula (1).
Furthermore, the use of compounds of formula

T
(3) f^^f^R4 . is preferred, wherein
R3 R5
R5 is is hydrogen; or CrC5alkyl; and
R3, R4, and T are defined as in formula (1); more preferably, wherein
R3 is Ci«C22alkyl; C6-Ci0aryl; or C7-Ci2aralkyl; and most preferably, wherein
R3 is C6-C10aryl.
Furtermore, the use of compounds of formula (1) is preferred, wherein at least one of the radicals Ri, R6 or Q is different from hydrogen.
Preferred is also the use of compounds of formula (1), wherein
Q is hydrogen; or Ci-C22alkyl;
T is -COR5; -CN; or -S02-(C6-C12)aryl;
Ri is hydrogen; or Ci-C&alkyl;
R2 and R3 independently from each other are d-C22alkyl;
R4 is CN; COR5; CONH2; or S02(C6-C12)aryl,
R5 is -OR7; -SR7) -NHR7, -NR7R8; CrC22alkyl; C7-Ci2aralkyl;
R7 and R8 independently from each other are hydrogen; Ci-C&alkyl; -(CH2)m-Si-RioRnRi2; Si(OR10)(ORii)(OR12); SiR10(ORn)(OR12); SiR10Rn(OR12), or a radical X-Sil;
R9 is a (C|-C6)alkylidene radical;
Rio, Rn, R12 independently form each other are CrC^alkyl;
X is a linker;
Sil is a silane-, oligosiloxane- or polysiloxane radical;
Ri and R2, Ri and Q, RT and R6) R, and T, R2 and R3j R2 and R4, R2 and R6, R2 and Q, R4 and R6) R4 and T, R6 and Q, T and Q, each independently, are linked together, so that 1, 2, 3 or 4 carbocyclic or N, O and/or S-heterocyclic rings are formed, wherein each of them, independently from each other, may be condensed with an aromatic or heteroaromatic ring, and/or more N-, O- and/or S-heterocycic rings, and each N atom in a N-heterocyclic ring may be substituted by Ci-C22alkyl;
n is anumber from 1 to 4; and
m is a number for 0 to 4; wherein at least one of the radicals R1f R6 or Q is different from hydrogen;

Preferred is the usse of compounds of formula (1), wherein
Ri, R6 and Q, independently from each other are hydrogen; or C-rC22alkyl, wherein at least
one of Ri, R6 and Q is different from hydrogen; and most preferrd the use of compounds of
formula (1), wherein
R-i, R6 and Q, independently from each other are hydrogen; or Ci-C5alkyl, wherein at least
one of Ri, R6 and Q is different from hydrogen.
Preferred is also the use according of compounds of formula (1), wherein
T and R4 independently from each other are -COR5; -CN; or -S02-(C6-C12)aryl; and
R5 is -OR7; -NR7R8; CrC22alkyl; C7-C12aralkyl;
R7 and R8 independently from each other are hydrogen; CrC22alkyl; ~(CH2)m-Si-RioRiiRi2;
and Rio, Rn, and R12 independently from each other are CrC22alkyl.
Most preferred is the use of compounds of formula (1), wherein
0-R7
T and R4 independently from each other are -CN; S02C6H5; -C~\ ; or a radical of
o
formula ,N—R7; wherein
0
R7 and R8, independently from each other are CrC12alkyl; or a radical of formula
-SiR7oRitRt2) and
Rio, Rn and R12 are CrC5alkyl.
Furthermore the present invention relates to the use of monomeric and polymeric compounds having the structural element of formula
R1 Q* O
(4) *•
wherein at least one of the asterix-marked radicals are joint with the monomeric or polymeric
radical; and
Ri, R2) R4 and R6 are defined as in formula (1).
Examples of merocyanine derivatives used in the present invention are listed in Table 1:

Table MC2a
R1 Q R3 R6 R4
Eg Es Q Re El T B4
MC01 i-propyl i-propyl OH H H 0
MC02
^-max =
374 nm CH3 CH3 OH H H : H
0
MC03
^•max =
375 nm CH3 CH3 OH H H 0 (T) A^
(RJ V o
MC04
^max =
363 nm CH3 CH3 OH H H %0
O
MC05
371 nm c CH3 OH H 0
MC06
^max =
384 nm CH3 CH3 OH H H 0
MC07 o OH H H 0

Table MC2a


N
R

2^

R, Q

T

^3 ^6 ^4

Ez

Ba

Q

Be

Bi

B4




MC08

CH:

n-butyl

OH

H

H

o
o



MC09

CH:

CH:

OH

H

s
I

A V




MC10

CH-

CH-

OH

-CN

-(CO)-CH3




0
MC11

CH.

CH-

OH

H

H


O^NH

o





o
0
MC12

o

OH

H

H

r

o



MC13

R2 + Ri

0-* (Ri) (R2)

CH

OH

H

-(CO)N(C2H5);

-(CO)-CH3



MC14

CH

CH

OH

X

-(CO)-CH3

(T)
(R,)



MC15

OH

H

H

Table MC2a
R, Q
R3 R6 R4
Eg Ba Q R§ Bl T S4
MC16
399 nm CH3 CH3 OH H H : H
MC17
^max =
373 nm CH3 i-propyl OH H H 0
MC18 i-propyl i-propyl OH H H 0
MC19
Amax =
380 nm CH3 CH3 OH CH3 H Y0
MC20 368 nm CH3 CH3 OH H H * * 1
0
MC21 CH3 CH3 -0-C6H5 H H -(CO)-CH3 CN
MC22 CH3 CH3 -0-CH3 H H -(CO)-O-CH3 CN
MC23 0 -OC2H5 H k -(CO)OCH3

Table MC2a
R, Q R3 R6 R4
Eg R3 Q Eg Si I R4
MC24 R9+R1:
Q
(R,) C2H5 -OC2H5 H -(CO)OC2H5 -(CO)OC2H5
MC25 CH3 CH3 t_;(Q)
(Re) H -CO-0-C2H5 -CN
MC26 CH3 CH3 Q+T:
A-
(Q) *
(T) H H -(CO)OC2H5
MC27 - CH3 CH3 Q+R,:
r? H -(C0)-0-CH3 -CN
MC28 CH3 CH3 Q+R!:
* *
(R,) (Q) H -(C0)-0-CH3 -S02"C6»H5
MC29
^rnax =
321 nm CH3 CH3 -N(CH3)2 H H -(C0)-CH3 -(CO)OC2H5
MC30 CH3 CH3 -N(CH3)2 H H -CN -(C0)-0CH3
MC31 321 nm CH3 CH3 -N(CH3)2 H H -(CO)OC2H5 -(CO)OC2H5
MC32 CH3 CH3 -NH2 H H -CN -(CO)OC2H5
MC33 CH3 CH3 0^ H H -CN -(CO)OC2H5

Table MC2a
R, Q


ns

Q

Be

Bi

R4



MC34

CH-

CH

Rfi+Q:

H

H

-CN

-(CO)OC2H5

(R„)


N-
/

*{Q)



MC35

CH

CH:

Rfi+Q:

H

H

-CN

-(CO)OC2H5

(Q).

MC36

R2+Q:
(Q)
*
I

CH:

H

H

-CN

-(CO)OC2H5




MC37

R2+Q1
H
(Q)

H

H

-CN

-(CO)OC2H5

(R2)


*"\ //
MC38

Rz+Q:
[ (Q) (*R2)

H

H

-CN

-(CO)OC2H5




o
(Q)
MC39

R?+Q:
I (C

CH-

H

H

-CN

Y
0

(R;


MC40
MC41

R?+Q:
I (Q) (*R2)
CH

CH

OH

H
H

H
H

-CN

-(CO)-0-C2H5
o ho
o #—
o

Table MC2a
R, Q




R

R3

Q

Ri

Bi

T

B_4



MC42

CH:

CH:

Q+T
0
A
HN N
,; J

H

H

-(CO)-0-C2H5

(T)

MC43

R2+Q:
(Q)
I IC

HO

H

H

-CN

-(CO)-0-C2H5

(R2)

MC44

R?+Q:
■n
I re
(Q)

CK

H

H

-(CO)-0-C2H5

-(CO)-0-C2H5

(R,


MC45

R9+Q_:
I tc
(Q)

H

H

-CN

-(CO)-0-C2H5



^•max
364 nm

(R2)



MC46

R?+Q:

H

H

H

-CN

-(CO)-0-C2H5


(Q)
(R2)



MC47

R2+Q:

(Q)

H

H

-CN

'Y
o

(Rs


(R2)
MC48

R?+Q:

(Q)

H

H

-CN

-(CO)-0-C2H5



MC49

CH.

CH

OH

H

H

: h°
o

MC50

CH:

CH:

CH:

H

H

-COOCH3

-COOCH3

Table MC2a
R3 R6 R4

B.2 B-3 Q Be Ri I S.4
MC51 CH3 CH3 CH3 H H -COO C2H5 -COO C2H5
MC52 CH3 CH3 CH3 H H -COO C3H7-(n) -COO C3H7-(n)
MC53 CH3 CH3 CH3 H H -COOC3H7(i) -COO C3H7-(i)
MC54 CH3 CH3 CH3 H H -COO C4H9(n) -COO C4Hg-(n)
MC55 CH3 CH3 CH3 H H -COO C4H9(t) -COO C4H9-(t)
MC56 CH3 CH3 CH3 H H -COO C2H5 -COOC4H9-(t)
MC57 CH3 CH3 CH3 H H -COOCH3 -COOC4H9-(t)
MC58 CH3 CH3 CH3 H H -COOC2H5 -COOSi(CH3)3
MC59 CH3 CH3 CH3 H H -COOSi(CH3)3 -COOSi(CH3)3
MC60 CH3 CH3 CH3 H H -C02CH2)3Si(CH3)3 -C02(CH2)3Si(CH3)
MC61 CH3 CH3 CH3 H H -CONHC2H5 -CONHC2H5
MC62 CH3 CH3 CH3 H H -CON(C2H5)2 -CON(C2H5)2
MC63 CH3 CH3 CH3 H H CN CN
MC64 CH3 CH3 CH3 H H CN SO2C6H6
MC65 CH3 CH3 CH3 H H CN COOC4H9-(n)
MC66 CH3 CH3 CH3 H H CN COOC8H17-(i)
MC67 CH3 CH3 CH3 H H CN COOCH3
MC68 CH3 CH3 CH3 H H CN COOC2H5
MC69 CH3 CH3 CH3 H H CN -CONHC2H5
MC70 CH3 CH3 CH3 H H CN -CON(C2H5)2
MC71 CH3 CH3 CH3 H H SO2C6H6 COOCH3
MC72 CH3 CH3 CH3 H H SO2C6H6 COOC2H5
MC73 CH3 CH3 CH3 H H SO2C6H6 COOC3H7
MC74 CH3 CH3 CH3 H H SOaCgHe COOC4H9
MC75 CH3 CH3 CH3 H H SO2C6H6 -COOC8H17(n)
MC76 CH3 CH3 CH3 H H SO2C6H6 COOC8H17(i)
MC77 CH3 CH3 CH3 H H SO2C6H6 -CONHC2H5
MC78 CH3 CH3 CH3 H H S02tolyl COOC2H5

Table MC2a
— — -
R3 R6 R4

E2 Es Q E6 Ei I Ri
MC79 CH3 CH3 CH3 H CH3 -COOCH3 -COOCH3
MC80 CH3 CH3 CH3 H CH3 -COOC2H5 -COOC2H5
MC81 CH3 CH3 CH3 H CH3 -COOC3H7(n) -COO C3H7-(n)
MC82 CH3 CH3 CH3 H CH3 -COOC3H7(i) -COO C3H7-(i)
MC83 CH3 CH3 CH3 H CH3 -COO C4H9-(n) -COO C4H9(n)
MC84 CH3 CH3 CH3 H CH3 -COO C4H9-(t) -COO C4H9(t)
MC85 CH3 CH3 CH3 H CH3 -COO C2H5 -COOC4H9-(t)
MC86 CH3 CH3 CH3 H CH3 -COOCH3 -COOC4H9-(t)
MC87 CH3 CH3 CH3 H CH3 -COOC2H5 -COOSi(CH3) 3
MC88 CH3 CH3 CH3 H CH3 -COOSi(CH3) 3 -COOSi(CH3) 3
MC89 CH3 CH3 CH3 H CH3 -CONHC2H5 -CONHC2H5
MC90 CH3 CH3 CH3 H CH3 -CON(C2H5)2 -CON(C2H5)2
MC91 CH3 CH3 CH3 H CH3 CN CN
MC92 CH3 CH3 CH3 H CH3 CN S02C6H6
MC93 CH3 CH3 CH3 H CH3 CN COOC4H9-(n)
MC94 CH3 CH3 CH3 H CH3 CN COOC8H17-(i)
MC95 CH3 CH3 CH3 H CH3 CN COOCH3
MC96 CH3 CH3 CH3 H CH3 CN COOC2H5
MC97 CH3 CH3 CH3 H CH3 CN -CONHC2H5
MC98 CH3 CH3 CH3 H CH3 CN -CON(C2H5)2
MC99 CH3 CH3 CH3 H CH3 SO2C6H6 COOCH3
MC100 CH3 CH3 CH3 H CH3 SO2C6H6 COOC2H5
MC101 CH3 CH3 CH3 H CH3 SO2C6H6 COOC3H7
MC102 CH3 CH3 CH3 H CH3 SO2C6H6 COOC4H9
MC103 CH3 CH3 CH3 H CH3 SO2C6H6 COOC8H17-(n)
MC104 CH3 CH3 CH3 H CH3 SO2C6H5 COOC8H17-(i)
MC105 CH3 CH3 CH3 H CH3 SO2C6H6 -CONHC2H5
MC106 CH3 CH3 CH3 H CH3 S02tolyl COOC2H5

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£(SHO)!SOOO- £ (eH0)!S0O0- H H £H0
zzion
SHZ0000- SHZ0000" H H £H0
I-ZIOW
£H0OO0 9H90z0S £H0 H £H0 * ¥*
n 03 LOW
(!HlH80OO0 NO £H0 H £H0
6 WOW
9H9OzOS NO £H0 H £H0
8H-0I/M
NO NO £H0 H £H0
ZUOW
e(eH0)!SOO0- e(eH0)!S000- £H0 H £H0
9U0W
SH20 000- SHZ0 000- £H0 H £H0
9W0I/M
9HzOOOO |A|0^0S H H £H0
ni-OIAI
£H0OO0 9H902OS H H eH0
ewow
SHZ0000 NO H H £H0
3W0IAI
9H902OS NO H H £H0
mow
NO NO H H £H0
OUOIAI
e (eH0)!SOO0- e (eH0)!SOO0- H H £H0
601OIAI
SHZ0 OOO- 9HZ0 000- H H £H0
8010W
sHz0HN00- |A|0^0S £H0 H £H0 £H0 £H0 LQIDW
*S i-l ^ "S 0 ga *s
*h 9a ea 6 ly

*zon ©iqei

Table MC2a
R, Q R3 R6 R4
R2 Ba Q Be Bi T B_4
MC134 i-propyl i-propyl CH3 H H 0
MC135 CH3 CH3 CH3 H H YN"
0
MC136 CH3 CH3 CH3 H H 0 0
MC137 c CH3 H H 0
MC138 R?+Ri: CH3 CH3 H VNX
0
MC139 CH3 H CH3 H CH3 -(CO)OCH3 -(CO)OCH3
MC140 . * H CH3 H 0
MC141 CH3 n-C4H9 CH3 H CH3 -(CO)-0-C2H5 -(CO)-0-C2H5
MC142 CH3 CH3 CH3 H CH3 -(CO)-O-Na -(CO)-O-Na

Table MC2a
R, Q


Bz

£3

Q

Be

Ri

154



MC143

fk+Bil
(R2) [ \ -O

H

CH

H

-(CO)-O-Na

-(CO)-O-Na




MC144

CH:

CH:

H

H

CH:




MC145

CH:

CH.

H

-CN

-(CO)-CH3




\ //
MC146

CH:

CH.

CH:

H

H

NH

%J-


MC147

CH

H

CH:

-(CO)(CO)OC2H5

O
^ //

MC148

R? + Ri:
* (R:
" p— 1R,

CH

t-butyl

H

H

-(CO)N(C2H5);

-CO-CH3




MC149

i-propyl

i-propyl

H

-CN

-CN



MC150

CH

CH.

H

-CN

-CN



MC151

-(CH2)3-Si(CH3)3

CH:

H

H

-CO-C(CH3)3

-CO-O-C2H5



MC152

H

CH:

H

-(CO)OSi(CH3)3

-(CO)OSi(CH3)3

o

Table MC2a
R, Q R3 R6 R4
B2 B2 Q Ee Si I R4
MC153 n-C3H7 CH3 H H -CO-CH33 I
MC154 CH3 CH3 C2H5 H H -NH(CO)C5H12 -CN
MC155 C2H5 C2H5 CH3 CH3 CH3 -(CO)-0-C2H5 -(CO)-0-C2H5
MC156 CH3 CH3 0 H CH3 -(CO)-0-C2H5 -(CO)-0-C2H5
MC157 CH3 CH3 H 0 CH3 -(CO)-0-C2H5 -CN
MC158 CH3 CH3 0 H phenyl -(CO)-0-C2H5 -(CO)-0-C2H5
MC159 CH3 CH3 C 6H5Br H CH3 -CN -(CO)-0-C2H5
MC160 CH3 CH3 biphenyl H CH3 CN -(CO)-0-C2H5
MC161 CH3 CH3 0— (Q) H CN -(CO)-0-C2H5
MC162 CH3 CH3 phenyl H CH3 CN -(CO)-0-C2H5
MC163 £?-. CH3 H H *~~\ CN -(CO)-0-C2H5
MC164 n-butyl n-butyl CH3 H H -(CO)-0-C2H5 -SO2-C6H5
MC165 CH3 CH3 H H phenyl -(CO)-CH3 Y ^>
0 '
MC166 CH3 CH3 H H * -(CO)-CH3 -CN
MC167 CH3 CH3 *
6 H H -(CO)-0-CH3 -(CO)-0-CH3
MC168 CH3 CH3 H H phenyl -CN -(CO)OC(CH3)3

Table MC2a
R1 Q R3 R6 R„
Eg Es Q Rg , Bi I R.4
MC169 n-butyl n-butyl H H 1 f -CN -(CO)OC(CH3)3
MC170 C2H5 C2H5 H H CF3
6, -CN 0
MC171 CH3 CH3 'XX. H CH3 -CN O
MC172 £ H H * 1
XX -CN 'YY
0
MC173 C2H5 C2H5 H H 0"
* -CN -(CO)-0-C2H5
MC174 CH3 CH3 H H -CN -CN -(CO)-0-CH3
MC175 -C2H5OH -C2H5OH H H *
0 -CN -(CO)-0-C2H5
MC176 H C2H5 H H $ -CN -(CO)-0-C2H5
MC177 C2H5 n-butyl (Q) H -CN -CN
MC178 C2H5 C2H5 C2H5 H H (T = R4) 0 0

Table MC2a
R1 Q
R-N-YYT
R3 R6 R4
E2 Es Q Eg El I E.4
MC179 C2H5OH C2H5OH CH3 CH3 H -CN 0
NH HO
MC180 H Na03S CH3 H H * -(CO)CH3
MC181 0
—J C2H5 H H -CN H9
0
0
J
V-Si-MC182 * * C2H 5 H H 0
H; /
O-Si * 0
/
N
H
MC183

H

0 0


N

N
MC184

MC185

MC186

MC187





MC188

N N

MC189


MC190



in
MC191

R

10

(CH2)S R

10



R

-Si-fo

/

Sr

O Si O

Si-R^



R

12

R

12



MC192


MC193


OH O
MC194

MC195

OH O
°^°
^N^^V^-O'
^°YV^N^ o^o
O OH





MC196

OH O

MC197 ^^
OH 0
II N
n
MC198 \/r l-
Si+O Sin 60 r I
-0 Si-
1 fo-
J4 /
-Si
/ HN -r\ ^
0 N
The compounds of formula (1) are prepared according to known processes, as disclosed for example in J.Org.Chem. USSR (Engl.Transl.) 26(8), p. 1562f (1990); J.Heterocycl.Chem. 33(3), p. 763-766 (1996); Khimiya Geterotsiklicheskikh Soedinenii 11., p. 1537-1543 (1984); Khimiya Geterotsiklicheskikh Soedinenii 3, p. 397-404 (1982); Chem.Heterocycl.Comp. (Engl.Transl.) 24(8), 914-919(1988).
The synthesis of the compounds used in the present invention is also disclosed in
WO 0234710, Eur. J. Org. Chem. 2003, 2250-2253, J. Med. Chem. 1996, 39, 1112-1124 and
J. Org. Chem., Vol. 37, No. 8, 1972, 1141-1145 as follows:
R2 O R6"^ T R2X R1 Q
R Ri Q R4 R3 T F1
R3 1 4 R6 R4
Vinylogene CH-acid compounds are reacted with acetales of amides.
In J. Heterocyclic Chem., 27, 1990, 1143-1151 aminoacrylic acid esters or aminoacrylnitriles are reacted with ethoxymehtylenecyanoacetates in ethanol to the corresponding compounds used in the present invention.
In J. Prakt. Chem. 327 (1985) 4, 567-579 iminoformylation reactions are carried out on substituted crotonnitriles:

Or) O


R2x H Q
NH
/
Ft
N^y. N
R6 ii
N
The compounds of the formula (1) according to the present invention are particularly suitable as UV filters, i.e. for protecting ultraviolet-sensitive organic materials, in particular the skin and hair of humans and animals, from the harmful effects of UV radiation. These compounds are therefore suitable as sunscreens in cosmetic, pharmaceutical and veterinary medical preparations. These compounds can be used both in dissolved form and in the micronized state.
The UV absorbers according to the present invention can be used either in the dissolved state (soluble organic filters, solubelized organic filters) or in the micronised state (nano-scalar organic filters, particulate organic filters, UV-absorber pigments).
Any known process suitable for the preparation of microparticles can be used for the pre¬paration of the micronised UV absorbers, for example wet-mifling,wet-kneading, spray-drying from a suitable solvent, by the expansion according to the RESS process (Rapid Expansion of Supercritical Solutions) by re precipitation from suitable solvents.
The micronised UV absorbers so obtained usually have an average particle size from 0.02 to 2, preferably from 0.03 to 1.5, and more especially from 0,05 to 1.0 micrometer.
A further object of the present invention is a UV absorber dispersion, comprising
(a) a micronised UV absorber of formula (1), each of them having a particle size from 0,02 to
2 urn, and
(b) a suitable dispersing agent.
The cosmetic formulations or pharmaceutical compositions according to the present inven¬tion may additionally contain one or more than one further conventional UV filter.
The cosmetic or pharmaceutical preparations may be, for example, creams, gels, lotions, al¬coholic and aqueous/alcoholic solutions, emulsions, wax/fat compositions, stick preparations,

powders or ointments. In addition to the above-mentioned UV filters, the cosmetic or pharma¬ceutical preparations may contain further adjuvants as described below.
As water- and oil-containing emulsions (e.g. W/O, O/W, O/W/O and W/O/W emulsions or mi-croemulsions) the preparations contain, for example, from 0.1 to 30 % by weight, preferably from 0.1 to 15 % by weight and especially from 0.5 to 10 % by weight, based on the total weight of the composition, of one or more UV absorbers, from 1 to 60 % by weight, espec¬ially from 5 to 50 % by weight and preferably from 10 to 35 % by weight, based on the total weight of the composition, of at least one oil component, from 0 to 30 % by weight, especially from 1 to 30 % by weight und preferably from 4 to 20 % by weight, based on the total weight of the composition, of at least one emulsifier, from 10 to 90 % by weight, especially from 30 to 90 % by weight, based on the total weight of the composition, of water, and from 0 to 88.9 % by weight, especially from 1 to 50 % by weight, of further cosmetically acceptable adju¬vants.
The compounds of formula (1) may also be used as as an anti-wrinkle perception modifier (see Example 29). This is a futher object of the present invention.
Preferably, the following combinations comprising UV absorbers are of special interest:
The cosmetic or pharmaceutical preparations may be, for example, creams, gels, lotions, alcoholic and aqueous/alcoholic solutions, emulsions, wax/fat compositions, stick prepa¬rations, powders or ointments. In addition to the above mentioned UV filters, the cosmetic or pharmaceutical preparations may contain further adjuvants as described below.
As water- and oil-containing emulsions (e.g. W/O, O/W, O/W/O and W/O/W emulsions or microemulsions) the preparations contain, for example, from 0.1 to 30 % by weight, pre¬ferably from 0.1 to 15 % by weight and especially from 0.5 to 10 % by weight, based on the total weight of the composition, of one or more UV absorbers, from 1 to 60 % by weight, especially from 5 to 50 % by weight and preferably from 10 to 35 % by weight, based on the total weight of the composition, of at least one oil component, from 0 to 30 % by weight, especially from 1 to 30 % by weight und preferably from 4 to 20 % by weight, based on the total weight of the composition, of at least one emulsifier, from 10 to 90 % by weight, especially from 30 to 90 % by weight, based on the total weight of the composition, of water,

and from 0 to 88.9 % by weight, especially from 1 to 50 % by weight, of further cosmetically acceptable adjuvants.
The cosmetic or pharmaceutical compositions/preparations according to the invention may also contain one or one more additional compoundsl like fatty alcohols, esters of fatty acids, natural or synthetic triglycerides including glyceryl esters and derivatives, pearlescent waxes:hydrocarbon oils: silicones or siloxanes (organosubstituted super-fatting agents, surfactantsconsistency regulators/thickeners and rheology modifiers, polymers, biogenic active ingredients, deodorising active ingredients, anti-dandruff agents, antioxidants, hydrotropic agents, preservatives and bacteria-inhibiting agents, perfume oils, colourants, polymeric beads or hollow spheres as spf enhancers,
Cosmetic or pharmaceutical preparations
Cosmetic or pharmaceutical formulations are contained in a wide variety of cosmetic
preparations. There come into consideration, for example, especially the following
preparations:
skin-care preparations, e.g. skin-washing and cleansing preparations in the form of
tablet-form or liquid soaps, soapless detergents or washing pastes,
bath preparations, e.g. liquid (foam baths, milks, shower preparations) or solid bath
preparations, e.g. bath cubes and bath salts;
skin-care preparations, e.g. skin emulsions, multi-emulsions or skin oils;
cosmetic personal care preparations, e.g. facial make-up in the form of day creams or
powder creams, face powder (loose or pressed), rouge or cream make-up, eye-care
preparations, e.g. eyeshadow preparations, mascara, eyeliner, eye creams or eye-fix
creams; lip-care preparations, e.g. lipsticks, lip gloss, lip contour pencils, naif-care
preparations, such as nail varnish, nail varnish removers, nail hardeners or cuticle
removers;
foot-care preparations, e.g. foot baths, foot powders, foot creams or foot balsams,
special deodorants and antiperspirants or callus-removing preparations;
light-protective preparations, such as sun milks, lotions, creams or oils, sunblocks or
tropicals, pre-tanning preparations or after-sun preparations;
skin-tanning preparations, e.g. self-tanning creams;

depigmenting preparations, e.g. preparations for bleaching the skin or skin-lightening preparations;
insect-repellents, e.g. insect-repellent oils, lotions, sprays or sticks; deodorants, such as deodorant sprays, pump-action sprays, deodorant gels, sticks or roll-ons;
antiperspirants, e.g. antiperspirant sticks, creams or roll-ons;
preparations for cleansing and caring for blemished skin, e.g. synthetic detergents (solid or liquid), peeling or scrub preparations or peeling masks;
hair-removal preparations in chemical form (depilation), e.g. hair-removing powders, liquid hair-removing preparations, cream- or paste-form hair-removing preparations, hair-removing preparations in gel form or aerosol foams;
shaving preparations, e.g. shaving soap, foaming shaving creams, non-foaming shaving creams, foams and gels, preshave preparations for dry shaving, aftershaves or aftershave lotions;
fragrance preparations, e.g. fragrances (eau de Cologne, eau de toilette, eau de parfum, parfum de toilette, perfume), perfume oils or perfume creams;
cosmetic hair-treatment preparations, e.g. hair-washing preparations in the form of shampoos and conditioners, hair-care preparations, e.g. pretreatment preparations, hair tonics, styling creams, styling gels, pomades, hair rinses, treatment packs, intensive hair treatments, hair-structuring preparations, e.g. hair-waving preparations for permanent waves (hot wave, mild wave, cold wave), hair-straightening preparations, liquid hair-setting preparations, hair foams, hairsprays, bleaching preparations, e.g. hydrogen per¬oxide solutions, lightening shampoos, bleaching creams, bleaching powders, bleaching pastes or oils, temporary, semi-permanent or permanent hair colourants, preparations containing self-oxidising dyes, or natural hair colourants, such as henna or camomile.
Presentation forms
The final formulations listed may exist in a wide variety of presentation forms, for example:
in the form of liquid preparations as a W/O, OAV, O/W/O, W/O/W or PIT emulsion and all
kinds of microemulsions,
in the form of a gel,
in the form of an oil, a cream, milk or lotion,
in the form of a powder, a lacquer, a tablet or make-up,

in the form of a stick,
in the form of a spray (spray with propellent gas or pump-action spray) or an aerosol,
in the form of a foam, or
in the form of a paste.
Of special importance as cosmetic preparations for the skin are light-protective preparations, such as sun milks, lotions, creams, oils, sunblocks or tropicals, pretanning preparations or after-sun preparations, also skin-tanning preparations, for example self-tanning creams. Of particular interest are sun protection creams, sun protection lotions, sun protection milk and sun protection preparations in the form of a spray.
Of special importance as cosmetic preparations for the hair are the above-mentioned prepa¬rations for hair treatment, especially hair-washing preparations in the form of shampoos, hair conditioners, hair-care preparations, e.g. pretreatment preparations, hair tonics, styling creams, styling gels, pomades, hair rinses, treatment packs, intensive hair treatments, hair-straightening preparations, liquid hair-setting preparations, hair foams and hairsprays. Of special interest are hair-washing preparations in the form of shampoos.
A shampoo has, for example, the following composition: from 0.01 to 5 % by weight of a UV absorber according to the invention, 12.0 % by weight of sodium laureth-2-sulfate, 4.0 % by weight of cocamidopropyl betaine, 3.0 % by weight of sodium chloride, and water ad 100%.
Other typical ingredients in such formulations are preservatives, bactericides and bacterio¬static agents, perfumes, dyes, pigments, thickening agents, moisturizing agents, humectants, fats, oils, waxes or other typical ingredients of cosmetic and personal care formulations such as alcohols, poly-alcohols, polymers, electrolytes, organic solvents, silicon derivatives, emollients, emulsifiers or emulsifying surfactants, surfactants, dispersing agents, antioxi¬dants, anti-irritants and anti-inflammatory agents etc.
The cosmetic preparation according to the invention is distinguished by excellent protection of human skin against the damaging effect of sunlight.

Preparation Examples


Example 1: Preparation of the compound of formula

A mixture of 8,58 g of dehydroacetic acid with 7,63 g of N,N-Dimethylformamid-dimethyl-acetate in 100 ml of tert.-butylmethylether is stirred for 8 hours at room temperature. Then the product is filtered off, washed with minor amounts of tert.-butylmethylether and dried in vacuum at 40°C. The yield is nearly quantitative. Fp: 159-161 °C.


Example 2: Preparation of compound of formula

A mixture of 1 g of 1-Ethoxycarbonyl-1-cyano-2-(N-dimethylaminomethylen)amino-4-di-methylaminobutadiene (prepared according to Chem. Heterocycl. Compd. (Engl. Transl.), 24, 8, 1988, 918) with 0,43 g of p-toluidine in 10 ml of dimethylformamide is boiled for 1 hour. The solvent is evaporated, the residue is ground in ether, filtered and dried in vacuum at 40 °C yielding 0,75 g of colorless crystals. Fp: 210-216 °C.

Example 3: Preparation of the compound of formula X^N

O

O^O
A mixture of 8.62 g pyrrolidine, 16.34 g malonic acid-cycl.-isopropylidene ester and 14.68 g acetylacetaldehyd dimethylacetal in 100 ml Toluene are stirred for 45 minutes at room temperture an kept under reflux for 67 hours.
The reactio mixture is sitrred for 4 h at 3°C and finally for 16 h at room temperture. The raw product is filtered off and washed with diethylether and finally 4 times with 10 ml methanol.
After drying in vacuo at 60 °C 2.70 g of the product of formula (1) are obtained as bright-orange crystals. ^max= 396 nm.


Example 4: Preparation of the compound: of formula

A mixture of 1,16 g of 1-Ethoxycarbonyl-1-cyano-2-(N-dimethylaminomethylen)amino-4-dimethylaminobutadiene (prepared according to Chem. Heterocycl. Compd. (EngL Transl.), 24, 8, 1988, 918) with 0,47 g of aniline in 11 ml of acetic acid is boiled for 1 hour. After cooling to room temperature the product is filtered off, recrystallized from toluene/ethyl acetate (1:1) yielding yellow crystals which were dried in vacuum at 40°C. The yield is 25 %. ^max = 363 nm.
Application Examples
Example 5: UV-A/UV-B Dailv Care UV Protection Lotion
INCI-Name % w/w (as supplied)
Part A Oleth-3 Phosphate 0.60
Steareth-21 2.50
Steareth-2 1.00
Cetyl Alcohol 0.80
Stearyl Alcohol 1.50
Tribehenin 0.80
Isohexadecane 8.00
Ethylhexyl Methoxycinnamate 5.00
PartB Water qs to 100
Glycerin 2.00
UV-absorber as described in examples 1 to 4 3.00
Disodium EDTA 0.10
Parte Water 20.00
Diazolidinyl Urea (and) lodopropynyl Butylcarbamate 0.15
Propylene Glycol 4.00

% w/w
INCI-Name (as supplied)
PartD Sodium Acrylates Copolymer (and) Paraffinium Liquidum (and)
PPG-1 Trideceth-6
Cyclopentasiloxane 1.50 4.50
PEG-12Dimethicone 2.00
Tocopheryl Acetate 0.45
Water (and) Citric Acid qs
PartE Fragrance qs
Manufacturina instruction:
Part A and part B are heated separately to 75°C. Part A is poured into part B under con¬tinuous stirring. Immediately after the emulsification, Cyclopentasiloxane and PEG-12 Di-methicone from part D are incorporated into the mixture. Afterwards the mixture is homo¬genized with an Ultra Turrax at 11 000 rpm for 30 sec. After cooling down to 65°C Sodium Acrylates Copolymer (and) Paraffinium Liquidum (and) PPG-1 Trideceth-6 are incorporated. Part C is added at a temperature Example 6: UV Day Lotion
INCI-Name % w/w
(as supplied)
Part A Cetyl Phosphate 1.75
C12-C15 Alkyl Benzoate 5.00
Cetearyl Alcohol/ PEG-20 Stearate 2.00
Ethoxydiglycol Oleate 2.00
Stearic Acid 1.50
Ethylhexyl Methoxycinnamate 3.00
Isononyl Isononanoate 2.00
PartB Aqua qsto 100
Xanthan Gum 0.35
UV-absorber as described in examples 1 to 4 5.00
Disodium EDTA 0.20
Propylene Glycol 2.00
Diazolidinyl Urea (and) Methylparaben (and) Propylparaben (and) 0.70

INCI-Name % w/w
(as supplied)
Propylene Glycol
Glycerin 1.50
Part C Cyclopentasiloxane (and) Dimethiconol 1.00
Ethoxydiglycol 3.00
Dimethicone 2.00
Part D Triethanolamine qs
Manufacturing instruction:
Part A is prepared by incorporating all ingredients, then stirred under moderate speed and
heated to 75°C. Part B is prepared and heated to 75°C. At this temperature part B is poured
into part A under progressive stirring speed. Then the mixture is homogenized (30sec,
15000 rpm ). At a temperature mixture is cooled down under moderate stirring, then the pH is checked and adjusted with
triethanolamine.
Example 7: Sun Protection Emulsion
Part A
PartB
PartC
PartD
% w/w
INCI-Name (as supplied)
Cetearyl Alcohol (and) Dicetyl Phosphate (and) Ceteth-10
Phosphate
C12-15AlkylBenzoate 4.00 2.00
Dicaprylyl Ether 3.00
Ethoxydiglycol Oleate 2.00
Stearic Acid 1.00
Ethylhexyl Methoxycinnamate 3.00
Sodium Acrylates Copolymer (and) Glycine Soja (and) PPG-1
Trideceth-6
Squalane 0.30 3.50
Aqua qs to 100
UV-absorber as described in examples 1 to 4 5.00
Diazolidinyl Urea (and) lodopropynyl Butylcarbamate 0.15
Propylene Glycol 2.50
Aqua 10.00
Cyclopentasiloxane, Dimethiconol 2.00
Ethoxydiglycol 5.00

% w/w
INCI-Name (as supplied)
Cyclopentasiloxane (and) DimethiconeA/inyl-dimethicone 2.00
Crosspolymer
Part E Sodium Hydroxide 0.10
Manufacturing instruction:
Part A is prepared by incorporating all ingredients, then stirred under moderate speed and heated to 75°C. Part B is prepared and heated to 75°C. At this temperature, part B is poured into part A under progressive stirring speed. Below 65°C the ingredients of part D are added separately. After cooling down under moderate stirring to 55°C part C is added. The pH is then checked and adjusted with sodium hydroxide. The mixture is homogenized for 30 sec at 16000rpm.
Example 8: Every Day Lotion
INCI-Name % w/w

Part A Stearyl Phosphate (as supplied) 5.00
Tricontanyl PVP 1.00
Ethoxydiglycol Oleate 3.00
Squalane 5.00
C12-15AlkylBenzoate 5.00
Ethylhexyl Methoxycinnamate 3.00
Glyceryl Stearate 2.00
Cetyl Alcohol 2.00
PartB Aqua 20.00
UV-absorber as described in examples 1 to 4 3.00
Parte Aqua qsto 100
Steareth-10 Allyl Ether/Acrylates Copolymer 0.50
Glycerin 2.50
Diazolidinyl Urea (and) lodopropynyl Butylcarbamate 0.15
Sodium Lauroyl Glutamate 0.70
PartD Cyclopentasiloxane (and) Dimethiconol 1.50
Triethanolamine 1.85
Manufacturing instruction:

Part A is prepared by incorporating all ingredients, then stirred under moderate speed and heated to 75°C. Part C is prepared and heated to 75°C. Part C is poured into the part A under moderate stirring. Immediately after the emulsification part B is added, then neutralized with a part of the-triethanolamine. The mixture is homogenized for 30 sec. After cooling down under moderate stirring Cyclopentasiloxane (and) Dimethiconol are added. Below 35°C the pH is checked and adjusted with triethanolamine.
Example 9: Spravable Sunscreen Emulsion
Part A INCI-Name
Ceteareth-15 (and) Glyceryl Stearate % w/w (as supplied) 3.00
Stearyl Alcohol 1.00
Cetyl Ricinoleate 0.80
Dicaprylyl Ether 3.00
C12-15AlkylBenzoate 3.00
Isohexadecane 2.50
Stearyl Dimethicone 1.00
Ethylhexyl Methoxycinnamate 4.00
Cetyl Alcohol 0.80
DI-C12-13 Alkyl Tartrate 3.00
PartB Aqua qsto 100
Steareth-10 Allyl Ether/Acrylates Copolymer 0.45
PEG-7 Glyceryl Cocoate 2.50
Glycerin 2.00
Propylene Glycol 3.00
PartC Diazolidinyl Urea (and) lodopropynyl Butylcarbamate 0.15
Aqua 20.00
UV-absorber as described in examples 1 to 4 12.00
Titanium Dioxide (and) Silica (and) Sodium Polyacrylate 8.00
PartD Cyclopentasiloxane (and) Dimethiconol 0.85
PartE PartF Sodium Hydroxide (and) Water Fragrance qs to pH 6.50
-7.00
qs

Manufacturing instruction
Part A and part B are heated up to 80°C. Part A is blended into part B under stirring and homogenized with an UltraTurrax at 11 000 rpm for 30 sec. Part C is heated to 60°C and added slowly to the emulsion. After cooling down to 40°C part D is incorporated at room temperature and part E is added.
Example 10: Daily Care Lotion
INCI-Name % w/w
(as supplied)
Part A Polyglyceryl Methyl Glucose Distearate 2.50
Cetearyl Alcohol 2.00
Octyl Stearate 3.00
Caprylic/Capric Triglyceride 4.00
Isohexadecane 4.00
Ethylhexyl Methoxycinnamate 2.70
Part B Aqua 64.80
Glycerin 5.00
Phenoxyethanol (and) Methylparaben (and) Butylparaben (and) 0.50
Ethylparaben (and) Propylparaben
UV-absorber as described in examples 1 to 4 8.00
Part C Cyclomethicone (and) Dimethicone 3.00
Part D Steareth-10 Allyl Ether/Acrylates Copolymer 0.50
Manufacturing instruction
Part A and B are heated to 75°C. Part A is added into part B under continuous stirring and homogenized with 11000 rpm for 1 minute. After cooling down to 50°C part C is added under continuous stirring. After cooling further down to 30°C part D is added. Afterwards the pH is adjusted between 6.00 - 6.50.
Example 11: Daily Care with UV Protection
INCI-Name % w/w
(as supplied)
Part A Glyceryl Stearate SE 3.00
Glyceryl Stearate and PEG-100 Stearate 3.50
Cetyl Alcohol 1.50
Myristyl Myristate 2.00

PartB
PartC

I NCI-Name % w/w
(as supplied)
Isopropyl Palmitate 2.50
Paraffinum Perliquidum 5.00
Octyl Dimethyl PABA 3.00
Aqua qsto 100
Propylene Glycol 7.50
Phenoxyethanol (and) Methylparaben (; and) Butylparaben (and) 1.00
Ethylparaben (and) Propylparaben
Aqua 30.00
UV-absorber as described in examples 1 to 4 10.00

Part D Sodium Acrylates Copolymer (and) Paraffinium Liquidum (and) 2.00
PPG-1 Trideceth-6
Part E Citric Acid 0.30
Manufacturing instruction:
Part A and B are heated separately to 75°C. After adding part B into part A the mixture is homogenized with Ultra Turrax for one minute at 11000 rpm. After cooling down to 50°C part C is added. Afterwards the mixture is homogenized for one minute at 16000 rpm. At a temperature Example 12: O/W Every Day UV Protection Lotion
INCI-Name % w/w
(as supplied)
Part A Glyceryl Stearate (and) PEG-100 Stearate 5.00
Stearyl Alcohol 1.00
Tripalmitin 0.70
Dimethicone 2.00
C12-15 Alkyl Benzoate 5.00
Isopropyl Palmitate 5.00
Ethylhexyl Methoxycinnamate 3.00
PartB Water qsto 100
Polysorbate 60 0.50
Glycerin 3.00

INCI-Name
Part C Water
UV-absorber dispersion as described in examples 1 to 4
Part D Phenoxyethanol (and) Methylparaben (and) Ethylparaben (and) Butylparaben (and) Propylparaben (and) Isobutylparaben Steareth-10 Allyl Ether/Acrylates Copolymer
Part E Water (and) Sodium Hydroxide
Part F Fragrance

% w/w (as supplied)
10.00
8.00
0.70
1.50
qs
qs

Manufacturing instruction:
Part A and B are heated separately up to 75°C, part C is heated to 60°C. Afterwards part B is poured into part A under stirring. The mixture is homogenized with an Ultra Turrax for 30 sec. at 11 000 rpm and part C is incorporated. After cooling down to 40°C part D is added. At room temperature the pH-value is adjusted with Sodium Hydroxide between 6.30 and 6.70 and part F is added.
Example 13: O/W Every Day UV Protection
INCI-Name % w/w (as suDDlied)
Part A Glyceryl Stearate (and) PEG-100 Stearate 5.00
Stearyl Alcohol 1.00
Tripalmitin 0.70
Dimethicone 2.00
C12-15AlkylBenzoate 5.00
Isopropyl Palmitate 5.00
Ethylhexyl Methoxycinnamate 3.00
PartB Water qs to 100
Polysorbate 60 0.50
Glycerin 3.00
Parte Water 10.00
UV-absorber dispersion as described in examples 1 to 4 8.00
PartD Phenoxyethanol (and) Methylparaben (and) Ethylparaben (and) Butylparaben (and) Propylparaben (and) Isobutylparaben Steareth-10 Allyl Ether/Acrylates Copolymer 0.70 1.50
PartE Water (and) Sodium Hydroxide qs

INCl-Name % w/w
(as supplied)
Part F Fragrance qs
Manufacturing instruction:
Part A and B are heated separately up to 75°C, part C is heated to 60°C. Afterwards part B is poured into part A under stirring. The mixture is homogenized with an Ultra Turrax for 30 sec. at 11 000 rpm and part C is incorporated. After cooling down to 40°C part D is added. At room temperature the pH-value is adjusted with Sodium Hydroxide between 6.30 and 6.70 and part F is added.
Example 14: Sunscreen Cream
(as supplied)
Cetearyl Alcohol (and) Dicetyl Phosphate (and) Ceteth-10
Phosphate
C12-15AlkylBenzoate 4.50 6.00
Caprylic/Capric Triglyceride 7.00
Pentaerythritol Tetraisostearate 2.00
Ethylhexyl Methoxycinnamate 3.00
Isoamyl p-Methoxycinnamate 2.00
Aqua qsto 100
Glycerin 2.00
Propylene Glycol 1.50
Magnesium Aluminium Silicate 1.20
Steareth-10 Allyl Ether/Acrylates Copolymer 0.50
UV-absorber dispersion as described in examples 1 to 4 12.00
Phenyl Trimethicone 1.50
Phenoxyethanol (and) Methylparaben i (and) Butylparaben (and ) 0.70
INCl-Name % w/w
Part A
PartB
Parte
PartD
Ethylparaben (and) Propylparaben
Part E Sodium Hydroxide 0.90
Manufacturing instruction:
Part A and part B are heated separately to 75°C. Part B is added into part A under con¬tinuous stirring and afterwards homogenized with Ultra Turrax for 30sec at 11000 rpm . After cooling down to 60°C part C is added. At 40°C part C is added and homogenized for 15sec at 11000 rpm. At room temperature the pH-value is adjusted with part E.

Example 15: UVA/UVB Daily Care Lotion, type O/W
Part A INCI-Name
Glyceryl Stearate (and) PEG-100 Stearate % w/w (as supplied) 5.00
Stearyl Alcohol 1.00
Tripalmitin 0.70
Mineral Oil 15.00
PartB Water qs to 100
Polysorbate 60 0.50
Glycerin 3.00
PartC Water 10.00
UV-absorber dispersion as described in examples 1 to 4 8.00
PartD Steareth-10 Allyl Ether/Acrylates Copolymer 1.50
PartE Phenoxyethanol (and) Methylparaben (and) Ethylparaben (and) Butylparaben (and) Propylparaben (and) Isobutylparaben Water (and) Sodium Hydroxide 0.70 qs
PartF Fragrance qs
Manufacturinq instruction:
Part A and B are heated separately to 75°C; part C to 60°C. Part B is poured into part A under stirring. After one-minute of homogenization at 11000 rpm part C is added to the mixture of A/B. After cooling down to 40°C part D is incorporated. At room temperature the pH value is adjusted with part E between 6.3 and 7.0. Finally part F is added.
Example 16: UVA/UVB Daily Care Lotion, type O/W
INCI-Name % w/w
(as supplied)
Part A Oleth-3 Phosphate 0.60
Steareth-21 2.50
Steareth-2 1.00
Cetyl Alcohol 0.80
Stearyl Alcohol 1.50
Tribehenin 0.80
Isohexadecane 8.00
PartB Water qsto 100
Glycerin 2.00

INCI-Name % w/w
(as supplied)
DisodiumEDTA 0.10
Part C Cyclopentasiloxane 4.50
PEG-12 Dimethicone 2.00
Part D Sodium Acrylates Copolymer (and) Mineral Oil (and) PPG-1 1.50
Trideceth-6
Part E UV-absorber dispersion as described in examples 1 to 4 10.00
Part F Tocopheryl Acetate 0.45
DMDM Hydantoin (and) lodopropynyl Butylcarbamate (and) 0.85
Aqua (and) Butylene Glycol
Part G Water (and) Citric Acid qs
Fragrance qs
Manufacturing instruction;
Part A and part B are heated separately to 75°C. Part A is poured into part B under stirring. Immediately after the emulsification, part C is added to the mixture and homogenized with an Ultra Turrax at 11000 rpm for 30 sec. After cooling down to 65°C Sodium Acrylates Copoly¬mer (and) Mineral Oil (and) PPG-1 Trideceth-6 At 50°C is added slowly to the UV absorber dispersion. At about 35-30°C part F is incorporated. The pH is adjusted with part G between 5.5 and 6.5.
Example 17: UV-A/UV-B Every Day Protection Lotion O/W
INCI-Name % w/w
(as supplied)
Part A Glyceryl Dilaurate 2.00
Ethylhexyl Palmitate 6.00
Cetyl Alcohol 1.00
Glyceryl Stearate 2.00
Laureth-23 1.00
Isopropyl Palmitate 2.00
Tribehenin 0.80
Beeswax 1.50
Lanolin Oil 1.00
PartB Water qsto 100
Propylene Glycol 4.00
Water (and) Titanium Dioxide (and) Alumina (and) Sodium Meta- 4.00

INCI-Name % w/w
(as supplied)
phosphate (and) Phenoxyethanol (and) Sodium Methylparaben
Part C Steareth-10 Allyl Ether/Acrylates Copolymer 1.00
Part D Phenoxyethanol (and) Methylparaben (and) Ethylparaben (and) 1.00
Butylparaben (and) Propylparaben (and) Isobutylparaben
UV-absorber dispersion as described in examples 1 to 4 8.00
Part E Water (and) Sodium Hydroxide qs
Manufacturing instruction:
Part A and part B are heated separately up to 80°C. Part A is poured into part B while stirring and homogenized with an Ultra Turrax by 11000 rpm for 30 sec. After cooling down to 60°C part C is incorporated. At 40°C part D is added slowly under continuous stirring. The pH is adjusted with part E between 6.50 - 7.00.
Example 18: Spravable Sunscreen Lotion
INCI-Name % w/w
(as supplied)
Part A Potassium Cetyl Phosphate 0.20
Isohexadecane 7.00
VP/Eicosene Copolymer 1.50
Di-C12-13 Alkyl Tartrate 6.00
Ethylhexyl Triazone 2.50
C12-15 Alkyl Benzoate 4.50
PartB Water qsto 100
Sorbeth-30 2.00
Sorbitan Stearate (and) Sucrose Cocoate 4.00
Titanium Dioxide (and) Alumina (and) Silica (and) Sodium 2.50
Polyacrylate
Part C Water 30.00
UV-absorber dispersion as described in examples 1 to 4 12.00
Part D Phenoxyethanol (and) Methylparaben (and) Ethylparaben (and) 0.70
Butylparaben (and) Propylparaben (and) Isobutylparaben
Part E Water (and) Citric Acid qs
Manufacturing instruction:
Part A and part B are heated separately up to 80°C, part C is heated to 50°C. Part B is
poured into part A and homogenized with an Ultra Turrax for 1 minute at 11000 rpm. After

cooling down to 50°C part C is added under continuous stirring. At 40°C part D is incor¬porated and homogenized again for 10 sec. at 11000 rpm. The pH is adjusted with part E.
Example 19: O/W Every Day UV Protection Lotion
INCI-Name % w/w
(as supplied)
Part A Glyceryl Stearate (and) PEG-100 Stearate 5.00
Stearyl Alcohol 1.00
Tripalmitin 0.70
Dimethicone 2,00
Caprylic/Capric Triglyceride 5.00
Isopropyl Palmitate 5.00
Ethylhexyl Methoxycinnamate 3.00
PartB Water qsto 100
Polysorbate 60 0.50
Glycerin 3.00
PartC Water 10.00
UV-absorber dispersion as described in examples 1 to 4 8.00
Part D Phenoxyethanol (and) Methylparaben (and) Ethylparaben (and) 0.70
Butylparaben (and) Propylparaben (and) Isobutylparaben
Steareth-10 Allyl Ether/Acrylates Copolymer 1.50
Part E Water (and) Sodium Hydroxide qs
Part F Fragrance qs
Manufacturing instruction:
Part A and part B are heated separately up to 75°C, part C is heated to 60°C. Afterwards part B is poured into part A under stirring. The mixture is homogenized with an Ultra Turrax for 30 sec. at 11 000 rpm and part C is incorporated. After cooling down to 40°C part D is added. At room temperature the pH-value is adjusted with Sodium Hydroxide between 6.30 and 6.70 and part F is added.
Example 20: Water resistant Sunscreen Emulsion
INCI-Name % w/w
(as supplied)
Part A Polyglyceryl-10 Pentastearate (and) Behenyl Alcohol (and) 2.50
Sodium Stearoyl Lactylate

INCI-Name % w/w
(as supplied)
VP/Eicosene Copolymer 1.50
Stearyl Alcohol 1.50
Squalane 4.00
C12-15 Alkyl Benzoate 7.50
Octocrylene 1.50
4-Methylbenzylidene Camphor 3.00
Ethylhexyl Methoxycinnamate 2.00
PartB Water qsto 100
Glycerin 1.80
Steareth-10 Ally! Ether/Acrylates Copolymer 0.80
Part C UV-absorber dispersion as described in examples 1 to 4 9.00
Part D VP/Hexadecene Copolymer 2.70
Cyclomethicone 1.50
Phenoxyethanol (and) Methylparaben (and) Ethylparaben (and) 0.70
Butylparaben (and) Propylparaben (and) Isobutylparaben Part E Aqua (and) Tocopheryl Acetate (and) Caprylic/Capric Triglyceride 3.50
(and) Polysorbate 80 (and) Lecithin
Part F Fragrance qs
Water (and) Sodium Hydroxide qs
Manufacturing instruction:
Part A and part B are heated separately to 80°C. Part A is poured into part B under con¬tinuous stirring. Afterwards the mixture is homogenized with an Ultra Turrax at 11 000 rpm for 1 min. After cooling down to 60°C part C is incorporated. At 40°C part D is added and the mixture homogenized for a short time again. At 35°C part E is added and at room tempera¬ture Fragrance is added. Finally the pH is adjusted with Sodium Hydroxide.
Example 21: UVA/UVB Sun Protection Lotion, O/W type
INCI-Name % w/w
(as supplied)
Part A Potassium Cetyl Phosphate 2.00
Tricontanyl PVP 1.00
Caprylic/Capric Triglyceride 5.00
C12-15 Alkyl Benzoate 5.00
Cetearyl Isononanoate 5.00

INCl-Name % w/w
(as supplied)
Glyceryl Stearate 3.00
Cetyl Alcohol 1.00
Dimethicone 0.10
Ethylhexyl Methoxycinnamate 5.00
PartB Water qsto 100
Glycerin 3.00
Part C Steareth-10 Allyl Ether/Acrylates Copolymer 0.50
Part D UV-absorber dispersion as described in examples 1 to 4 8.00
Part E Phenoxyethanol (and) Methylparaben (and) Ethylparaben (and) 1.00
Butylparaben (and) Propylparaben (and) Isobutylparaben
Part F Water (and) Sodium Hydroxide qs to pH 7.00
Part G Fragrance qs
Manufacturing instruction:
Part A and part B are heated separately up to 80°C. Part B is poured into part A under moderate stirring. The mixture is homogenized with an Ultra Turrax at 11000 rpm for 1 minute. After cooling down to 70°C part C is added under stirring. After cooling further
down to 50°C part D is incorporated very slowly. At 40°C part E is added. At room
temperature the pH is adjusted with part F to 7.00 and part G is added.
Example 22: UVA/UVB Sun Protection Lotion. O/W type
INCl-Name % w/w
(as supplied)
Part A Potassium Cetyl Phosphate 2.00
Tricontanyl PVP 1.00
Caprylic/Capric Triglyceride 5.00
C12-15 Alkyl Benzoate 5.00
Cetearyl Isononanoate 5.00
Glyceryl Stearate 3.00
Cetyl Alcohol 1.00
Dimethicone 0.10
Ethylhexyl Methoxycinnamate 5.00
PartB Water qsto 100

INCI-Name % w/w
(as supplied)
Glycerin 3.00
Part C Steareth-10 Allyl Ether/Acrylates Copolymer 0.50
Part D UV-absorber dispersion as described in examples 1 to 4 20.00
Part E Phenoxyethanol (and) Methylparaben (and) Ethylparaben 1.00
(and) Butylparaben (and) Propylparaben (and) Isobutylparaben
Part F Water (and) Sodium Hydroxide qs to pH 7.00
Part G Fragrance qs
Manufacturing instruction:
Part A and part B are heated separately up to 80°C. Part B is poured into part A under moderate stirring. The mixture is homogenized with an Ultra Turrax at 11000 rpm for 1 minute. After cooling down to 70°C add part C is added under stirring. After cooling further
down to 50°C part D is incorporated very slowly. At 40°C part E is added. At room
temperature the pH is adjusted with part F to 7.00 and part G is added.
Example 23: Sunscreen Lotion
INCI-Name % w/w
(as supplied)
Part A Cetearyl Alcohol (and) Dicetyl Phosphate (and) Ceteth-10 4.00
Phosphate
C12-15 Alkyl Benzoate 2.00
Dicaprylyl Ether 3.00
Ethoxydiglycol Oleate 2.00
Stearic Acid 1.00
Ethylhexyl Methoxycinnamate 3.00
Sodium Acrylates Copolymer (and) Glycine Soja (and) PPG-1 0.30
Trideceth-6
Squalane 3.50
VP/Eicosene Copolymer 2.00
Part B Water qsto 100
UV-absorber dispersion as described in examples 1 to 4 5.00
Part C Diazolidinyl Urea (and) lodopropynyl Butylcarbamate 0.15
Propylene Glycol 2.50
Water 10.00
Part D Cyclopentasiloxane (and) Dimethiconol 2.00

INCI-Name % w/w
(as supplied)
Ethoxydiglycol 5.00
Cyclopentasiloxane (and) Dimethicone/Vinyl Dimethicone 2.00
Crosspolymer
Part E Aqua (and) Sodium Hydroxide qs
Part F Fragrance qs
Manufacturing instruction
Part A and part B are heated separately up to 75°C. Part B is poured into part A under progressive stirring speed. At a temperature Example 24: W/O Sunscreen Lotion
Part A INCI-Name
PEG-7 Hydrogenated Castor Oil % w/w
(as supplied)
3.00
Polyglyceryl-3 Diisostearate 4.00
Microcrystalline Wax 1.00
Magnesium Stearate 1.50
Propylparaben 0.10
Mineral Oil 15.00
Octyldodecanol 8.00
Ethylhexyl Triazone 1.00
Ethylhexyl Methoxycinnamate 2.00
PartB Water qsto 100
Water (and) Citric Acid 0.05
Methylparaben 0.15
Magnesium Sulfate 0.50
PartC UV-absorber dispersion as described in example 1 or 2 Fragrance 9.00 qs

Manufacturing instruction:
Part A is heated to 80°C whilst stirring. Part B is added into part A and homogenized with an
Ultra Turrax at 11 000 rpm for one minute. After cooling down to 30°C part C is incorporated.
Example 25: Skin Protection Sunscreen Lotion W/Q
Part A INCI-Name
Polyglyceryl-2 Dipolyhydroxystearate % w/w
(as supplied)
3.00
Glyceryl Oleate 3.00
Cetearyl Isononanoate 7.00
Hexyl Laurate 6.00
Dicaprylyl Ether 6.00
Propylparaben 0.10
Hexyldecanol 3.00
Magnesium Stearate 1.00
Beeswax 1.00
Ethylhexyl Methoxycinnamate 4.00
PartB Water qs to 100
Methylparaben 0.15
Magnesium Sulfate 1.00
Parte UV-absorber dispersion as described in examples 1 to 4 6.00
Manufacturino instruction:
Part A is heated separately to 80°C under gentle stirring. Part B is added to part A and homogenized for one minute at 11000 rpm. After cooling down to 30°C part C is added under continuous stirring.
Example 26: O/W emulsion

INCI-Name % w/w
(as supplied)
Part A UV absorber of formula (MC 14) 3g
sesame oil 10g
glyceryl stearate 4g
stearic acid ig
cetyl alcohol 0.5 g

INCi-Name % w/w
(as supplied)
polysorbate 20 0.2 g
PartB propylene glycol 4g
propylparaben 0.05 g
methylparaben 0.15 g
triethanolamine 0.1 g
carbomer 934 0.1 g
water ad 100 ml
Preparation of the emulsion
Phase (A):
Firstly, the UV absorber is dissolved in sesame oil. The other components of (A) are added
thereto and combined.
Phase (B):
Propylparaben and methylparaben are dissolved in propylene glycol. 60 ml of water are then
added, heating to 70°C is carried out and then carbomer 934 is emulsified therein.
Emulsion:
(A) is slowly added to (B) with vigorous application of mechanical energy. The volume is
adjusted to 100 ml by the addition of water.

Example 27: Daily care cream, type O/W INCI name
Part A
% w/w
Glyceryl stearate (an
cocoglycerides
Ceteareth-12 d) cetearyl alcohol (and) cetyl palmitate (and) (as used) 4.0
4.0
Cetearyl alcohol 2.0
Dicaprylyl ether 4.5
Ethylhexyl stearate 4.0
Hexyl laurate 3.5
Ethylhexyl triazone 1.0
Benzylidene malonate polysiloxane 2.0
HDI/trimethylol hexyl -lactone crosspolymer (and) silica 5.0

INCI name % w/w
(as used)
Stearyl dimethicone 1.0
Dimethicone 2.0
Cetyl alcohol 0.8
compound of formula (MC 14) 2.0
PartB Water q.s. to 100
Water (and) scleroglucan (and) phenoxyethanol 2.0
Glycerol 2.0
Part C Steareth-10 allyl ether/acrylate copolymer 0.45
Phenoxyethanol (and) methylparaben (and) ethylparaben (and) 0.7
butylparaben (and) propylparaben (and) isobutylparaben Part D Aqua (and) tocopherol acetate (and) caprylic/capric triglyceride 4.0
(and) polysorbate 80 (and) lecithin
Part E Water (and) sodium hydroxide q.s.
Fragrance q.s.
Preparation procedure:
Part A and part B are heated separately to 80°C. Part A is poured into part B, whilst stirring continuously. Afterwards the mixture is homogenized with an Ultra Turrax at 11 000 rpm for 20 sec. The mixture is cooled to 60°C and part C is added. At a temperature below 30°C, part D is added and the pH value is adjusted with sodium hydroxide to between 6.5 and 7.0. Finally, fragrance is added.
Example 28: Sun-protection cream, type O/W
INCI name % w/w
(as used)
Part A Polyglyceryl-3 methylglucose distearate 2.0
Decyl oleate 5.7
Isopropyl palmitate 5.8
Caprylic/capric triglyceride 6.5
compound of formula (MC 14) 2.0
Ethylhexyl methoxycinnamate 5.0
Cetyl alcohol 0.7
Part B Glycerol 3.0
Carbomer 0.3
Water q.s. to 100

INCI name % w/w
(as used)
Parte Phenoxyethanol (and) methylparaben (and) ethylparaben (and) 0.5
butylparaben (and) propylparaben (and) isobutylparaben
Part D Methylene bis-benzotriazolyl tetramethylbutylphenol (and) aqua 8.0
(and) decyl glucoside (and) propylene glycol (and) xanthan gum
Water 20.0
Part E Water (and) sodium hydroxide q.s.
Fragrance q.s.

Preparation procedure
Part A and part B are heated separately to 75°C. Part A is poured into part B whilst stirring. The mixture is homogenised with an Ultra Turrax at 11 000 rpm for 15 sec. The mixture is cooled to 60°C and part C and part D are incorporated. The mixture is homogenised again for a short time (5 sec/11 000 rpm) and further cooled, with moderate stirring. At room temperature, the pH is adjusted with sodium hydroxide solution to between 5.5 and 6.0. Finally, fragrance is added.
Example 29: Daily care UV-protection lotion
INCI name % w/w
Part A
PartB
Parte

Oleth-3 phosphate (as used) 0.6
Steareth-21 2.5
Steareth-2 1.0
Cetyl alcohol 0.8
Stearyl alcohol 1.5
Tribehenin 0.8
Isohexadecane 8.0
compound of formula (MC 14) 5.0
Water q.s. to 100
Glycerol 2.0
Methylene bis-benzotriazolyl tetramethylbutylphenol (and) aqua (and) decyl glucoside (and) propylene glycol (and) xanthan gum Disodium EDTA 3.0 0.1
Water 20.0
Diazolidinyl urea (and) iodopropynyl butylcarbamate 0.15
Propylene glycol 4.0

INC! name % w/w
(as used)
Part D Sodium acrylate copolymer (and) liquid paraffin (and) PPG-1 1.5
trideceth-6
Cyclopentasiloxane 4.5
PEG-12 dimethicone 2.0
Tocopheryl acetate 0.45
Water (and) citric acid q.s.
Part E Fragrance q.s.
Preparation procedure
Heat part A and part B separately to 75°C. Pour part A into part B, whilst stirring continuously. Immediately after emulsification, incorporate in the mixture SF 1202 and SF 1288 from part D. Afterwards homogenise with an Ultra Turrax at 11 000 rpm for 30 sec. Allow to cool to 65°C and incorporate SALCARE® SC91. At a temperature below 50°C, add part C. At 35°C or below, incorporate vitamin E acetate and subsequently adjust the pH with citric acid. At room temperature, add part E.
Example 30: Sun-protection cream, type O/W
INCI name % w/w
(as used)
Part A Polyglyceryl-3 methylglucose distearate 2.0
Decyl oleate 5.7
Isopropyl palmitate 5.8
Caprylic/capric triglyceride 6.5
compound of formula (MC 14) 2.0
Ethylhexyl methoxycinnamate 5.0
Cetyl alcohol 0.7
Part B Glycerol 3.0
Carbomer 0.3
Water q.s. to 100
Part C Phenoxyethanol (and) methylparaben (and) ethylparaben (and) 0.5 butylparaben (and) propylparaben (and) isobutylparaben
Part D Methylene bis-benzotriazolyl tetramethylbutylphenol (and) aqua 8.0
(and) decyl glucoside (and) propylene glycol (and) xanthan gum
Water 20.0
Part E Water (and) sodium hydroxide q.s.

INCI name % w/w
(as used)
Fragrance q.s.
Preparation procedure:
Part A and part B are heated separately to 75°C. Part A is poured into part B whilst stirring. The mixture is homogenised with an Ultra Turrax at 11 000 rpm for 15 sec The mixture is cooled to 60°C, and part C and part D are incorporated. The mixture is homogenised again for a short time (5 sec/11 000 rpm). After further cooling, with moderate stirring, the pH is adjusted with sodium hydroxide at room temperature. A solution between pH 5.50 and 6.00 is obtained. Finally, fragrance is added.
Example 31: Sun-protection cream, type O/W
INCI name % w/w
(as used)
Part A Polyglyceryl-3 methylglucose distearate 2.0
Decyl oleate 5.7
Isopropyl palmitate 5.8
Caprylic/capric triglyceride 6.5
Mixture of the compound of formula (MC 14) (50 %) and Uvinul A 2.0
Plus CAS Reg. No. 302776-68-7 (50 %)
Ethylhexyl methoxycinnamate 5.0
Cetyl alcohol 0.7
Part B Glycerol 3.0
Carbomer 0.3
Water q.s. to 100
Part C Phenoxyethanol (and) methylparaben (and) ethylparaben (and) 0.5 butylparaben (and) propylparaben (and) isobutylparaben
Part D Methylene bis-benzotriazolyl tetramethylbutylphenol (and) aqua 8.0
(and) decyl glucoside (and) propylene glycol (and) xanthan gum
Water 20.0
Part E Water (and) sodium hydroxide q.s.
Fragrance q.s.
Preparation procedure:
Part A and part B are heated separately to 75°C. Part A is poured into part B whilst stirring. The mixture is homogenised with an Ultra Turrax at 11 000 rpm for 15 sec After cooling 60°C, part C and part D are incorporated. The mixture is homogenised again for a short time

(5 sec/11 000 rpm). After further cooling, with moderate stirring, the pH is adjusted at room temperature with sodium hydroxide solution to between 5.50 and 6.00. Finally, fragrance is added.
Example 32: Sun-protection cream, type O/W
INCI name % w/w
(as used)
Part A Polyglyceryl-3 methylglucose distearate 2.0
Decyl oleate 5.7
Isopropyl palmitate ■ 5.8
Caprylic/capric triglyceride 6.5
Mixture of compound of formula (MC 14) (50 %) and benzylidene 2.0
camphor, CAS Reg. No. 36861-47-9 (50 %)
Ethylhexyl methoxycinnamate 5.0
Cetyl alcohol 0.7
Part B Glycerol 3.0
Carbomer 0.3
Water q.s. to 100
Part C Phenoxyethanol (and) methylparaben (and) ethylparaben (and) 0.5 butylparaben (and) propylparaben (and) isobutylparaben
Part D Methylene bis-benzotriazolyl tetramethylbutylphenol (and) aqua 8.0
(and) decyl glucoside (and) propylene glycol (and) xanthan gum
Water 20.0
Part E Water (and) sodium hydroxide q.s.
Fragrance q.s.
Preparation procedure
Part A and part B are heated separately to 75°C. Part A is poured into part B whilst stirring. The mixture is homogenised with an Ultra Turrax at 11 000 rpm for 15 sec. After cooling to 60°C, part C and part D are incorporated. The mixture is homogenised again for a short time (5 sec/11 000 rpm). After further cooling, with moderate stirring, the pH is adjusted at room temperature with sodium hydroxide. A solution between pH 5.50 and 6.00 is obtained. Finally, fragrance is added.




















































The compounds of the formula (1) according to the present invention are particularly suitable as UV filters, i.e. for protecting ultraviolet-sensitive organic materials, in particular the skin and hair of humans and animals, from the harmful effects of UV radiation. These compounds are therefore suitable as sunscreens in cosmetic, pharmaceutical and veterinary medical preparations. These compounds can be used both in dissolved form and in the micronized state.
The UV absorbers according to the present invention can be used either in the dissolved state (soluble organic filters, solubelized organic filters) or in the micronised state (nano-scalar organic filters, particulate organic filters, UV-absorber pigments).
Any known process suitable for the preparation of microparticles can be used for the pre-paration of the micronised UV absorbers, for example wet-milling,wet-kneading, spray-drying from a suitable solvent, by the expansion according to the RESS process (Rapid Expansion of Supercritical Solutions) by re precipitation from suitable solvents.
The micronised UV absorbers so obtained usually have an average particle size from 0.02 to 2, preferably from 0.03 to 1.5, and more especially from 0,05 to 1.0 micrometer.
A further object of the present invention is a UV absorber dispersion, comprising
(a) a micronised UV absorber of formula (1), each of them having a particle size from 0,02 to
2 urn, and
(b) a suitable dispersing agent.
The cosmetic formulations or pharmaceutical compositions according to the present invention may additionally contain one or more than one further conventional UV filter.
The cosmetic or pharmaceutical preparations may be, for example, creams, gels, lotions, al-coholic and aqueous/alcoholic solutions, emulsions, wax/fat compositions, stick preparations,

powders or ointments. In addition to the above-mentioned UV filters, the cosmetic or pharmaceutical preparations may contain further adjuvants as described below.
As water- and oil-containing emulsions (e.g. W/O, O/W, O/W/O and W/O/W emulsions or mi-croemulsions) the preparations contain, for example, from 0.1 to 30 % by weight, preferably from 0.1 to 15 % by weight and especially from 0.5 to 10 % by weight, based on the total weight of the composition, of one or more UV absorbers, from 1 to 60 % by weight, especially from 5 to 50 % by weight and preferably from 10 to 35 % by weight, based on the total weight of the composition, of at least one oil component, from 0 to 30 % by weight, especially from 1 to 30 % by weight und preferably from 4 to 20 % by weight, based on the total weight of the composition, of at least one emulsifier, from 10 to 90 % by weight, especially from 30 to 90 % by weight, based on the total weight of the composition, of water, and from 0 to 88.9 % by weight, especially from 1 to 50 % by weight, of further cosmetically acceptable adjuvants.
The compounds of formula (1) may also be used as as an anti-wrinkle perception modifier (see Example 29). This is a futher object of the present invention.
Preferably, the following combinations comprising UV absorbers are of special interest:
The cosmetic or pharmaceutical preparations may be, for example, creams, gels, lotions, alcoholic and aqueous/alcoholic solutions, emulsions, wax/fat compositions, stick preparations, powders or ointments. In addition to the above mentioned UV filters, the cosmetic or pharmaceutical preparations may contain further adjuvants as described below.
As water- and oil-containing emulsions (e.g. W/O, O/W, O/W/O and W/O/W emulsions or microemulsions) the preparations contain, for example, from 0.1 to 30 % by weight, preferably from 0.1 to 15 % by weight and especially from 0.5 to 10 % by weight, based on the total weight of the composition, of one or more UV absorbers, from 1 to 60 % by weight, especially from 5 to 50 % by weight and preferably from 10 to 35 % by weight, based on the total weight of the composition, of at least one oil component, from 0 to 30 % by weight, especially from 1 to 30 % by weight und preferably from 4 to 20 % by weight, based on the total weight of the composition, of at least one emulsifier, from 10 to 90 % by weight, especially from 30 to 90 % by weight, based on the total weight of the composition, of water,

and from 0 to 88.9 % by weight, especially from 1 to 50 % by weight, of further cosmeticaily acceptable adjuvants.
The cosmetic or pharmaceutical compositions/preparations according to the invention may also contain one or one more additional compounds! like fatty alcohols, esters of fatty acids, natural or synthetic triglycerides including glyceryl esters and derivatives, pearlescent waxes:hydrocarbon oils: silicones or siloxanes (organosubstituted super-fatting agents, surfactantsconsistency regulators/thickeners and rheology modifiers, polymers, biogenic active ingredients, deodorising active ingredients, anti-dandruff agents, antioxidants, hydrotropic agents, preservatives and bacteria-inhibiting agents, perfume oils, colourants, polymeric beads or hollow spheres as spf enhancers,
Cosmetic or pharmaceutical preparations
Cosmetic or pharmaceutical formulations are contained in a wide variety of cosmetic
preparations. There come into consideration, for example, especially the following
preparations:
skin-care preparations, e.g. skin-washing and cleansing preparations in the form of
tablet-form or liquid soaps, soapless detergents or washing pastes,
bath preparations, e.g. liquid (foam baths, milks, shower preparations) or solid bath
preparations, e.g. bath cubes and bath salts;
skin-care preparations, e.g. skin emulsions, multi-emulsions or skin oils;
cosmetic personal care preparations, e.g. facial make-up in the form of day creams or
powder creams, face powder (loose or pressed), rouge or cream make-up, eye-care
preparations, e.g. eyeshadow preparations, mascara, eyeliner, eye creams or eye-fix
creams; lip-care preparations, e.g. lipsticks, lip gloss, lip contour pencils, nail-care
preparations, such as nail varnish, nail varnish removers, nail hardeners or cuticle
removers;
foot-care preparations, e.g. foot baths, foot powders, foot creams or foot balsams,
special deodorants and antiperspirants or callus-removing preparations;
light-protective preparations, such as sun milks, lotions, creams or oils, sunblocks or
tropicals, pre-tanning preparations or after-sun preparations;
skin-tanning preparations, e.g. self-tanning creams;

- dlepigmenting preparations, e.g. preparations for bleaching the skin or skin-lightening preparations;
- insect-repellents, e.g. insect-repellent oils, lotions, sprays or sticks; - deodorants, such as deodorant sprays, pump-action sprays, deodorant gels, sticks or roll-ons;
- antiperspirants, e.g. antiperspirant sticks, creams or roll-ons;
- preparations for cleansing and caring for blemished skin, e.g. synthetic detergents (solid or liquid), peeling or scrub preparations or peeling masks;
- hair-removal preparations in chemical form (depilation), e.g. hair-removing powders, liquid hair-removing preparations, cream- or paste-form hair-removing preparations, hair-removing preparations in gel form or aerosol foams;
shaving preparations, e.g. shaving soap, foaming shaving creams, non-foaming shaving creams, foams and gels, preshave preparations for dry shaving, aftershaves or aftershave lotions;
- fragrance preparations, e.g. fragrances (eau de Cologne, eau de toilette, eau de parfum, parfum de toilette, perfume), perfume oils or perfume creams;
cosmetic hair-treatment preparations, e.g. hair-washing preparations in the form of shampoos and conditioners, hair-care preparations, e.g. pretreatment preparations, hair tonics, styling creams, styling gels, pomades, hair rinses, treatment packs, intensive hair treatments, hair-structuring preparations, e.g. hair-waving preparations for permanent waves (hot wave, mild wave, cold wave), hair-straightening preparations, liquid hair-setting preparations, hair foams, hairsprays, bleaching preparations, e.g. hydrogen peroxide solutions, lightening shampoos, bleaching creams, bleaching powders, bleaching pastes or oils, temporary, semi-permanent or permanent hair colourants, preparations containing self-oxidising dyes, or natural hair colourants, such as henna or camomile.
Presentation forms
The final formulations listed may exist in a wide variety of presentation forms, for example:
- in the form of liquid preparations as a W/O, O/W, O/W/O, W/O/W or PIT emulsion and all
kinds of microemulsions,
- in the form of a gel,
- in the form of an oil, a cream, milk or lotion,
- in the form of a powder, a lacquer, a tablet or make-up,

- in the form of a stick,
- in the form of a spray (spray with propellent gas or pump-action spray) or an aerosol,
-=in the form of a foam, or
- in the form of a paste.
Of special importance as cosmetic preparations for the skin are light-protective preparations, such as sun milks, lotions, creams, oils, sunblocks or tropicals, pretanning preparations or after-sun preparations, also skin-tanning preparations, for example self-tanning creams. Of particular interest are sun protection creams, sun protection lotions, sun protection milk and sun protection preparations in the form of a spray.
Of special importance as cosmetic preparations for the hair are the above-mentioned preparations for hair treatment, especially hair-washing preparations in the form of shampoos, hair conditioners, hair-care preparations, e.g. pretreatment preparations, hair tonics, styling creams, styling gels, pomades, hair rinses, treatment packs, intensive hair treatments, hair-straightening preparations, liquid hair-setting preparations, hair foams and hairsprays. Of special interest are hair-washing preparations in the form of shampoos.
A shampoo has, for example, the following composition: from 0.01 to 5 % by weight of a UV absorber according to the invention, 12.0 % by weight of sodium laureth-2-sulfate, 4.0 % by weight of cocamidopropyl betaine, 3.0 % by weight of sodium chloride, and water ad 100%.
Other typical ingredients in such formulations are preservatives, bactericides and bacterio-static agents, perfumes, dyes, pigments, thickening agents, moisturizing agents, humectants, fats, oils, waxes or other typical ingredients of cosmetic and personal care formulations such as alcohols, poly-alcohols, polymers, electrolytes, organic solvents, silicon derivatives, emollients, emulsifiers or emulsifying surfactants, surfactants, dispersing agents, antioxi-dants, anti-irritants and anti-inflammatory agents etc.
The cosmetic preparation according to the invention is distinguished by excellent protection of human skin against the damaging effect of sunlight.










Manufacturing instruction:
Part A is prepared by incorporating all ingredients, then stirred under moderate speed and
heated to 75°C. Part B is prepared and heated to 75°C. At this temperature, part B is poured
into part A under progressive stirring speed. Below 65°C the ingredients of part D are added
separately. After cooling down under moderate stirring to 55°C part C is added. The pH is
then checked and adjusted with sodium hydroxide. The mixture is homogenized for 30 sec at
16000rpm.

Manufacturing instruction:

Part A is prepared by incorporating all ingredients, then stirred under moderate speed and heated to 75°C. Part C is prepared and heated to 75°C. Part C is poured into the part A under moderate stirring. Immediately after the emulsification part B is added, then neutralized with a part of the-triethanolamine. The mixture is homogenized for 30 sec. After cooling down under moderate stirring Cyclopentasiloxane (and) Dimethiconol are added. Below 35°C the pH is checked and adjusted with triethanolamine.


Manufacturing instruction
Part A and part B are heated up to 80°C. Part A is blended into part B under stirring and homogenized with an UltraTurrax at 11 000 rpm for 30 sec. Part C is heated to 60°C and added slowly to the emulsion. After cooling down to 40°C part D is incorporated at room temperature and part E is added.

Manufacturing instruction
Part A and B are heated to 75°C. Part A is added into part B under continuous stirring and homogenized with 11000 rpm for 1 minute. After cooling down to 50°C part C is added under continuous stirring. After cooling further down to 30°C part D is added. Afterwards the pH is adjusted between 6.00 - 6.50.



Manufacturing instruction:
Part A and B are heated separately to 75°C. After adding part B into part A the mixture is homogenized with Ultra Turrax for one minute at 11000 rpm. After cooling down to 50°C part C is added. Afterwards the mixture is homogenized for one minute at 16000 rpm. At a temperature


Manufacturing instruction:
Part A and B are heated separately up to 75°C, part C is heated to 60°C. Afterwards part B is poured into part A under stirring. The mixture is homogenized with an Ultra Turrax for 30 sec. at 11 000 rpm and part C is incorporated. After cooling down to 40°C part D is added. At room temperature the pH-value is adjusted with Sodium Hydroxide between 6.30 and 6.70 and part F is added.



Manufacturing instruction:
Part A and B are heated separately up to 75°C, part C is heated to 60°C. Afterwards part B is poured into part A under stirring. The mixture is homogenized with an Ultra Turrax for 30 sec. at 11 000 rpm and part C is incorporated. After cooling down to 40°C part D is added. At room temperature the pH-value is adjusted with Sodium Hydroxide between 6.30 and 6 JO and part F is added.

Manufacturing instruction:
Part A and part B are heated separately to 75°C. Part B is added into part A under continuous stirring and afterwards homogenized with Ultra Turrax for 30sec at 11000 rpm . After cooling down to 60°C part C is added. At 40°C part C is added and homogenized for 15sec at 11000 rpm. At room temperature the pH-value is adjusted with part E.




















Preparation of the emulsion
Phase (A):
Firstly, the UV absorber is dissolved in sesame oil. The other components of (A) are added
thereto and combined.
Phase (B):
Propylparaben and methylparaben are dissolved in propylene glycol. 60 ml of water are then
added, heating to 70°C is carried out and then carbomer 934 is emulsified therein.
Emulsion:
(A) is slowly added to (B) with vigorous application of mechanical energy. The volume is
adjusted to 100 ml by the addition of water.



Preparation procedure:
Part A and part B are heated separately to 80°C. Part A is poured into part B, whilst stirring continuously. Afterwards the mixture is homogenized with an Ultra Turrax at 11 000 rpm for 20 sec. The mixture is cooled to 60°C and part C is added. At a temperature below 30°C, part D is added and the pH value is adjusted with sodium hydroxide to between 6.5 and 7.0. Finally, fragrance is added.



Preparation procedure
Part A and part B are heated separately to 75°C. Part A is poured into part B whilst stirring. The mixture is homogenised with an Ultra Turrax at 11 000 rpm for 15 sec. The mixture is cooled to 60°C and part C and part D are incorporated. The mixture is homogenised again for a short time (5 sec/11 000 rpm) and further cooled, with moderate stirring. At room temperature, the pH is adjusted with sodium hydroxide solution to between 5.5 and 6.0. Finally, fragrance is added.

























wherein at least one of the asterix-marked radicals are joint with the monomeric or polymeric
radical; and
R1, R2, R4 and R6 are defined as in claim (1).
28. Use of the compounds of formula (1) as as an anti-wrinkle perception modifier.
29. A cosmetic preparation comprising at least one compound of formula (1) according to
claim 1 together with cosmetically tolerable carriers or adjuvants.
30. Cosmetic composition according to claim 29 wherein the compound of formula (1) is
present in the composition in the micronized state.
31. UV absorber dispersion, comprising
(a) at least one micronised UV absorber of formula (1), each of them having a particle size
from 0,02 to 2 µm, and
(b) a suitable dispersing agent.























R2 and R3 independently from each other are d-C22alkyl; C2-Ci2alkenyl; C2-Ci2alkinyl; C3-Ci2cycloalkyl, C3-d2cycloalkenyl; C7-Ci2aralkyl; d-C12heteroalkyl; C3-C12cyclohetero* alkyl; drdiheteroaralkyl, C6-C10aryl; or CrC9heteroaryl;
R4 is cyano; COR7, COOR7; CONR7R8; S02(C6-C12)aryl, C2-C12alk-1-enyi; C3-Ci2cycloalk-1-enyl; C2-C12alk«1-inyI;, C2-Ci2heteroalkyl, C3-C5heterocycloalkyl, C6-C10aryl; orCr Cgheteroaryl;
R5 is -COR7; -COOR7; -OR7; -SR7; -NR7R8; CrC22alkyl; C2-C12alkenyl; C2-Ci2alkinyl; C3-Ci2cycloalkyl; C3-Ci2cycloalkenyl; C7-Ci2aralkyl; d-C^alkylphenyl; d-d2alkoxy-d-Ci0aryl; Ci-Ci2heteroalkyl; C2-Cnheteroaralkyl; C3-C12cyc)oheteroalkyl; C6-doaryl; Cr Ci2alkoxy-C6-C10aryl or Ci-Cgheteroary!;
R6 is CrC22alkyI; d-C22alkoxy; or COR7;
R7 and R8 independently from each other are hydrogen; d-C22alkyl; C2-d2alkenyl; C2-Ci2alkinyl; d-Ci2cycloalkyl; C3-d2cycloalkenyl; C7-d2aralkyl; Ci-C^heteroalkyl; C2-Cnheteroaralkyl; drdoaryl; o-C6-doaryl; ord-C9heteroaryI;
R9 is a (d-C6)alkylidene radical; or
RT and R2, Ri and Q, RT and R4, Ri and R6, R2 and R3, R3 and G, R6 and Q, T and Q, each independently, are linked together, so that 1, 2, 3 or 4 carbocyclic or N, O and/or S-heterocyclic rings are formed, wherein each of them, independently from each other, may be condensed with an aromatic or heteroaromatic ring, and/or more N-, O- and/or S-heterocycic rings, and each N atom in a N-heterocyclic ring may be substituted by d-C22alkyl; and
n is 1.
3. Use according to claim 1 or 2, wherein
Q is -OH; -OR6; or -NR7R8;
T is -COR5 -CN; or-S02-(C6-C12)aryl;
Ri is hydrogen; -OR7, -SR7; -NR7R8; d-C22alkyl; C2-d2alkenyl; C2-C12alkinyl; C3-
Ci2cycloalkyl; C3-d2cycloalkenyl; CrC12aralkyl; or C6-C10aryl; R2 and R3 independently from each other are d-Q^alkyl; C2-d2alkenyl; C2-Ci2alkinyl; C3-
Ci2cycloalkyl; C3-C12cycloalkenyl; C7«Ci2aralkyl; orC6-doaryl; R4 is cyano; -COR5, -COOR7; -CONR7R8; -S02(C6-C12)aryl; -d-C22alkylcarbonylamino-C6-
Ci0aryl; or C6-C10aryl;

R5 is -COR7; -COOR7; -CONR7R6, -OR?, -SR7, -NR7R8) Ci-C22alkyl; C2-C12alkenyl; C2-Ci2alkinyl; C3-C12cycloalkyl; C3-Ci2cycloalkenyl; CrC12aralkyl; C6-C10aryl; or Cr C12alkoxy-C6-Ci0aryl;
Re, R7 and R8 independently from each other are hydrogen; CrC22alkyl; C3-C12cycloalkyl; C3-C12cycioalkenyl; C7-Ci2aralkyl; or C6-C10aryl; or
RT and R2, Ri and Q, Ri and R4t Ri and R6» R2 and R3) R3 and Q, R6 and Q, T and Q are linked together pairwise, so that 1, 2, 3 or 4 carbocyclic or N-, O- and/or S-heterocyclic rings are formed, wherein each of them, independently from each other may be con¬densed with an aromatic or heteroaromatic ring, and/or more N, O and/or S-heterocycic rings, and each N atom in a N-heterocyclic ring may be substituted by C1-C22alkyl.
4. Use according to any of claims 1 to 3, wherein in formula (1)
Ri is hydrogen; -S-d-C22alkyl; or Ri and R2, or R-, and R4 together with the linking nitrogen atom form an alkylene radical which my be interrupted by one or more -O- and/or -NR7-or may be condensed with an aromatic ring; and
R7 is Ci-C22alkyl; C3-Ci2cycloalkyl; C3-Ci2cycloalkenyl; C7-C12aralkyl; or C6-Ci0aryl.
5. Use according to claim 4, wherein in formula (1) Ri is hydrogen.
6. Use according to any of claims 1 to 5, wherein in formula (1)
R2 and R3 independently from each other are d-C5aIkyl; phenyl-Ci-C3alkyl; hydroxy-Ci-Ci2alkyl; or R2 and R3, or R2 and R4, or R2 and Q together with the linking nitrogen atom form an alkylene radical which my be interrupted by one or more -O- and/or -NR7- or may be condensed with an aromatic ring; and
R7 is C1-C22alkyl; C3-Ci2cycloalkyl; C3-Ci2cycloalkenyl; C7-Ci2aralkyl; orC6-Ci0aryl.
7. Use according to claim 6, wherein
R2 and R3 independently from each other are CrC5alkyl; or R2 and R3 together with the linking nitrogen atom form a C2-C4alkylene radical which may be interrupted by -O- or -NR7; and
R7 is hydrogen; or CrC5alkyl.
8. Use according to any of claims 1 to 7, wherein in formula (1)








2, 3 or 4 carbocyclic or N, 0 and/or S-heterocyclic rings are formed, wherein each of them, independently from each other, may be condensed with an aromatic or heteroaromatic ring, and/or more IM-, O- and/or S-heterocycic rings, and each N atom in a N-heterocyclic ring may be substituted by CrC22alkyl;
n is anumber from 1 to 4; and
m is a number for 0 to 4; wherein at least one of the radicals R1f R6 or Q is different from hydrogen;
23. Use according to claim 22, wherein
R1f R6 and Q, independently from each other are hydrogen; or C1-C22alkyl, wherein at least one of Ri, R6 and Q is different from hydrogen.
24. Use according to claim 22 or 23, wherein
Ri, R6 and Q, independently from each other are hydrogen; or Ci-C5alkyl, wherein at least one of R1( R6 and Q is different from hydrogen.
25. Use according to any of claims 21 to 24, wherein
T and R4 independently from each other are -COR5; -CN; or -S02-(C6-Ci2)aryl; and
R5 is -OR7; -NR7R8; CrC^alkyl; C7-C12aralkyl;
R7 and R8 independently from each other are hydrogen; Ci-C22alkyl; -(CH2)m-Si-Ri0RiiRi2;
and Rio. R11. and Ri2 independently from each other are CrC&alkyl.
26. Use according to any of claims 25, wherein
0-R7
T and R4 independently from each other are -CN; S02C6H5; -C—^ ; or a radical of
O
R8
formula /N—R7; wherein
o
R7 and R8, independently from each other are Ci-C^alkyl; or a radical of formula
-S1R10R11R12; and
R10, R11 and R12 are CrCsalkyl.
27. Monomeric and polymeric compounds having the structural element of formula

Documents:

4773-CHENP-2006 AMENDED PAGES OF SPECIFICATION 11-06-2013.pdf

4773-CHENP-2006 AMENDED CLAIMS 11-06-2013.pdf

4773-CHENP-2006 CORRESPONDENCE OTHERS 05-07-2013.pdf

4773-CHENP-2006 EXAMINATION REPORT REPLY RECEIVED 17-09-2013.pdf

4773-CHENP-2006 EXAMINATION REPORT REPLY RECEIVED 11-06-2013.pdf

4773-CHENP-2006 FORM-1 17-09-2013.pdf

4773-CHENP-2006 FORM-1 11-06-2013.pdf

4773-CHENP-2006 FORM-3 19-04-2013.pdf

4773-CHENP-2006 FORM-3 11-06-2013.pdf

4773-CHENP-2006 OTHER PATENT DOCUMENT 11-06-2013.pdf

4773-CHENP-2006 POWER OF ATTORNEY 11-06-2013.pdf

4773-CHENP-2006 PRIORITY DOCUMENT 11-06-2013.pdf

4773-CHENP-2006 AMENDED CLAIMS 17-09-2013.pdf

4773-CHENP-2006 AMENDED PAGES OF SPECIFICATION 17-09-2013.pdf

4773-CHENP-2006 CORRESPONDENCE OTHERS 19-04-2013.pdf

4773-CHENP-2006 CORRESPONDENCE OTHERS 20-07-2012.pdf

4773-CHENP-2006 FORM-13.pdf

4773-CHENP-2006 FORM-18 23-05-2008.pdf

4773-CHENP-2006 FORM-18.pdf

4773-CHENP-2006 FORM-3 15-06-2007.pdf

4773-CHENP-2006 FORM-3.pdf

4773-CHENP-2006 CORRESPONDENCE OTHERS.pdf

4773-CHENP-2006 FORM 5.pdf

4773-chenp-2006-abstract.pdf

4773-chenp-2006-claims.pdf

4773-chenp-2006-correspondnece-others.pdf

4773-chenp-2006-description(complete).pdf

4773-chenp-2006-form 1.pdf

4773-chenp-2006-form 26.pdf

4773-chenp-2006-form 3.pdf

4773-chenp-2006-form 5.pdf

4773-chenp-2006-pct.pdf

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Patent Number 257356
Indian Patent Application Number 4773/CHENP/2006
PG Journal Number 39/2013
Publication Date 27-Sep-2013
Grant Date 26-Sep-2013
Date of Filing 28-Dec-2006
Name of Patentee CIBA HOLDING INC.
Applicant Address KLYBECKSTRASSE 141, CH-4057 BASEL.
Inventors:
# Inventor's Name Inventor's Address
1 WAGNER BARBARA IM VOGELSANG 10 79539 LORRACH GERMANY
2 BIENEWALD FRANK 63 RUE DE HAGENTHAL F-68220 HEGENHEIM FRANCE
3 WALLQUIST OLOF SPECHSTRASSE 34 CH-4106 THERWIL SWITZERLAND
4 HERZOG BERND HORNRAIN 21 D-79639 GRENZACH-WYHLEN GERMANY
5 WOLLEB HEINZ STEINENBUHLSTRASSE 173 CHE-4232 FEHREN SWITZERLAND
6 EHLIS THOMAS HARRIET-STRAUB-STRASSE 23 79100 FREIBURG GERMANY
7 HAASE JURG HABERMARKWEG 45 CH-4126 BETTINGEN SWITZERLAND
PCT International Classification Number A61K7/42
PCT International Application Number PCT/EP05/52850
PCT International Filing date 2005-06-20
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 04103018.0 2004-06-29 EUROPEAN UNION