IP Library Granted Patent US 8,044,058
Granted Patent B2
US 8,044,058 · App. 12/715,839 · Granted Oct 25, 2011

Merocyanine derivatives

Assignee: BASF SE
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Quick Facts
Patent No.
US 8,044,058
App. No.
12/715,839
Granted
Oct 25, 2011
Kind
B2
Abstract

Disclosed is the use of merocyanine derivatives of formula Q is hydrogen; C 1 -C 22 alkyl; —OH; —OR 7 ; —NR 7 R 8 ; or —N═R 9 ; R 1 is hydrogen; C 1 -C 22 alkyl; —OR 7 , —SR 7 ; —NR 7 R 8 ; C 1 -C 22 alkyl; C 2 -C 12 alkenyl; C 2 -C 12 alkinyl; C 3 -C 12 cycloalkyl; C 3 -C 12 cycloalkenyl; C 7 -C 12 aralkyl; C 1 -C 12 heteroalkyl, C 2 -C 11 heteroaralkyl; C 6 -C 10 aryl; or C 1 -C 9 heteroaryl; R 4 is cyano; COR 7 , COOR 7 ; CONR 7 R 8 ; SO 2 (C 6 -C 12 )aryl; C 2 -C 12 alk-1-enyl; C 3 -C 12 cycloalk-1-enyl; C 2 -C 12 alk-1-inyl; C 2 -C 12 heteroalkyl; C 3 -C 5 heterocycloalkyl; C 6 -C 10 aryl; or C 1 -C 9 heteroaryl; R 5 is —COR 7 ; —COOR 7 ; —OR 7 ; —SR 7 , —NHR 7 , —NR 7 R 8 ; C 1 -C 22 alkyl; C 2 -C 12 alkenyl; C 2 -C 12 alkinyl; C 3 -C 12 cycloalkyl; C 3 -C 12 cycloalkenyl; C 7 -C 12 aralkyl; C 1 -C 12 alkylphenyl; C 1 -C 12 alkoxy-C 6 -C 10 aryl; C 1 -C 12 heteroalkyl; C 2 -C 11 heteroaralkyl; C 3 -C 12 cycloheteroalkyl; C 6 -C 10 aryl; C 1 -C 12 alkoxy-C 6 -C 10 aryl; or C 1 -C 9 heteroaryl; R 6 is hydrogen; C 1 -C 22 alkyl; C 1 -C 22 alkoxy; or COR 7 ; R 7 and R 8 independently from each other are hydrogen; C 1 -C 22 alkyl; C 2 -C 12 alkenyl; C 2 -C 12 alkinyl; C 3 -C 12 cycloalkyl; C 3 -C 12 cycloalkenyl; —(CH 2 ) t COOH; C 7 -C 12 aralkyl; C 1 -C 12 heteroalkyl; C 2 -C 11 heteroaralkyl; C 6 -C 10 aryl; C 1 -C 9 heteroaryl; Si—R 10 R 11 R 12 ; Si(OR 10 )(OR 11 )(OR 12 ); SiR 10 (OR 11 )(OR 12 ); SiR 10 R 11 (OR 12 ); —(CH 2 ) u —O—(CH 2 ) v —SiR 10 R 11 R 12 ; or a radical X-Sil; t, u and v, independently from each other are a number from 1 to 5; R 9 is a (C 1 -C 6 )alkylidene radical; R 10 , R 11 , R 12 independently form each other are C 1 -C 22 alkyl; X is a linker; for protecting of human hair and skin against the damaging effect of UV radiation.

Claims (36)

1. A cosmetic or pharmaceutical preparation comprising at least one compound of formula (1) together with cosmetically tolerable carriers or adjuvants

Q is hydrogen; C 1 -C 22 alkyl; —OH; —OR 7 ; —NR 7 R 8 ; or —N═R 9 ;

R 1 is hydrogen; C 1 -C 22 alkyl; —OR 7 , —SR 7 ; —NR 7 R 8 ; C 1 -C 22 alkyl; C 2 -C 12 alkenyl; C 2 -C 12 alkinyl; C 3 -C 12 cycloalkyl; C 3 -C 12 cycloalkenyl; C 7 -C 12 aralkyl; C 1 -C 12 heteroalkyl, C 2 -C 11 heteroaralkyl; C 6 -C 10 aryl; or C 1 -C 9 heteroaryl;

R 4 is cyano; COR 7 , COOR 7 ; CONR 7 R 8 ; SO 2 (C 6 -C 12 )aryl; C 2 -C 12 alk-1-enyl; C 3 -C 12 cycloalk-1-enyl; C 2 -C 12 alk-1-inyl; C 2 -C 12 heteroalkyl; C 3 -C 5 heterocycloalkyl; C 6 -C 10 aryl; or C 1 -C 9 heteroaryl;

R 5 is —COR 7 ; —COOR 7 ; —OR 7 ; —SR 7 , —NHR 7 , —NR 7 R 8 ; C 1 -C 22 alkyl; C 2 -C 12 alkenyl; C 2 -C 12 alkinyl; C 3 -C 12 cycloalkyl; C 3 -C 12 cycloalkenyl; C 7 -C 12 aralkyl; C 1 -C 12 alkylphenyl; C 1 -C 12 alkoxy-C 6 -C 10 aryl; C 1 -C 12 heteroalkyl; C 2 -C 11 heteroaralkyl; C 3 -C 12 cycloheteroalkyl; C 6 -C 10 aryl; C 1 -C 12 alkoxy-C 6 -C 10 aryl; or C 1 -C 9 heteroaryl;

R 6 is hydrogen; C 1 -C 22 alkyl; C 1 -C 22 alkoxy; or COR 7 ,

R 7 and R 8 independently from each other are hydrogen; C 1 -C 22 alkyl; C 2 -C 12 alkenyl; C 2 -C 12 alkinyl; C 3 -C 12 cycloalkyl; C 3 -C 12 cycloalkenyl; —(CH 2 ) t COOH; C 7 -C 12 aralkyl; C 1 -C 12 heteroalkyl; C 2 -C 11 heteroaralkyl; C 6 -C 10 aryl; C 1 -C 9 heteroaryl; Si—R 10 R 11 R 12 ; Si(OR 10 )(OR 11 )(OR 12 ); SiR 10 (OR 11 )(OR 12 ); SiR 10 R 11 (OR 12 ); —(CH 2 ) u —O—(CH 2 ) v —SiR 10 R 11 R 12 ; or a radical X-Sil;

t, u and v, independently from each other are a number from 1 to 5;

R 9 is a (C 1 -C 6 )alkylidene radical;

R 10 , R 11 , R 12 independently form each other are C 1 -C 22 alkyl;

X is a linker;

Sil is a silane-, oligosiloxane- or polysiloxane radical;

R 1 and R 2 , R 1 and Q, R 1 and R 6 , R 1 and T, R 2 and R 3 , R 2 and R 4 , R 2 and R 6 , R 2 and Q, R 4 and R 6 , R 4 and T, R 6 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-heterocyclic rings, and each N atom in a N-heterocyclic ring may be substituted by C 1 -C 22 alkyl;

n is a number from 1 to 4; wherein at least one of the radicals R 1 , R 6 or Q is different from hydrogen;

if n=1

T is —COR 5 ; —CN; C 6 -C 10 aryl; —NHR 5 ; or —SO 2 —(C 6 -C 12 )aryl;

R 2 and R 3 independently from each other are C 1 -C 22 alkyl; hydroxy-C 1 -C 22 alkyl; C 2 -C 12 alkenyl; C 2 -C 12 alkinyl; C 3 -C 12 cycloalkyl, C 3 -C 12 cycloalkenyl; C 7 -C 12 aralkyl; C 1 -C 12 heteroalkyl; C 3 -C 12 cycloheteroalkyl; C 6 -C 10 aryl; C 1 -C 9 heteroaryl; or a radical of formula

p is a number from 5 to 100

q is a number from 1 to 5;

s is a number from 0 to 4;

if n=2

R 2 and R 3 are each C 1 -C 5 alkylene; and simultaneously T is defined as for n=1; or

T is a bivalent radical of formula —NR 7 —V—NR 7 —, wherein

V is phenylene; or C 1 -C 5 alkylene;

R 7 is hydrogen; or C 1 -C 5 alkyl; and R 2 and R 3 simultaneously are defined as for n=1;

if n=3

one of R 2 , R 3 or T is a trivalent radical;

if n=4

one of R 2 , R 3 or T is a tetravalent radical;

for protecting of human hair and skin against the damaging effect of UV radiation.

2. The cosmetic or pharmaceutical preparation according to claim 1 wherein the compound of formula (1) is present in the preparation in the micronized state.

3. The cosmetic or pharmaceutical preparation according to claim 2 wherein the compound of formula (1) is present in a 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.

4. The cosmetic or pharmaceutical preparation according to claim 1 wherein said preparation is selected from the group consisting of anti-wrinkle perception modifiers, skincare preparations, bath preparations, cosmetic personal care preparations, eye-care preparations, lip-care preparations, nail-care preparations, foot-care preparations, light-protective preparations, skin-tanning preparations, depigmenting preparations, insect repellents, deodorants, antipersirants, hair removal preparations, shaving preparations, fragrance preparations, and cosmetic hair-treatment preparation.

5. The cosmetic or pharmaceutical preparation according to claim 1 wherein said preparation is selected from the group consisting of creams, gels, lotions, alcoholic and aqueous solutions, alcoholic solutions, emulsions, wax/fat compositions, stick preparations, powders and ointments.

Assignments (2)
CHANGE OF NAME Recorded Apr 11, 2011
From: CIBA SPECIALTY CHEMICALS CORPORATION
To: CIBA CORPORATION
Reel/Frame 026102/0395 →
ASSET TRANSFER AGREEMENT Recorded Apr 11, 2011
From: CIBA CORPORATION
To: BASF SE
Reel/Frame 026102/0446 →
Priority Claims (1)
EP 04103018 · Jun 29, 2004 · regional
Continuity (2)
Continuation 11630489
Related Publication 20100209466A1 · Aug 19, 2010