US 9,068,080 B2Granted

Merocyanine derivatives

AssigneeBASF SE

InventorBarbara Wagner

Life of this patent

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Abstract

Disclosed are merocyanine derivatives which correspond to the formula (I), wherein L1, L2 and L3 independently of each other are hydrogen; or L1 and L3 may be linked together to form a carbocyclic ring; R3 and R4 independently of each other are CN; —COR5; —COOR5; —CONR5R6; C1-C22alkyl; C2-C22alkenyl; C2-C22alkinyl; C3-C12cycloalkyl; C3-C12cycloalkenyl; C7-C20aralkyl; C1-C20heteroalkyl; C3-C12cycloheteroalkyl; C3-C18heteroaralkyl; C6-C20 aryl; C1-C12alkylcarbonylamino-C6-C20aryl; C2-C12heteroaryl; or —X2—Sil2; n is a number from 1 to 4; the meaning of R1 and R2 depends on the definition of n. The compounds are useful as UV absorbers for cosmetic applications.

Claims8

Dependent claims

Merocyanine derivatives of formula (1)

wherein
L2 is hydrogen;
and L1 and L3 are linked together to form a carbocyclic ring;
R3 is —X2—Sil2, wherein Sil2 is a polysiloxane of the formula (4a) or (4b)
and
X2 is C1-C18alkylene;
or a bivalent radical of the formula (5a), (5b) or (5c)
wherein the asterix * is linked to Sil2 and the asterix ** is linked to R3 or R4;
and
w is a number from 0 to 30,
wherein
R8, R9, R10 independently form each other are C1-C22alkyl;
C6-C20aryl;
C1-C22alkoxy;
or O—C6-C20aryl;
A is a bond to X1 or X2;
x is a number from 4 to 250;
y is a number from 5 to 250;
and
z is a number from 1 to 50;
and
n is 1, 2, or 4;
R4 is CN;
—COR5;
—COOR5;
—CONR5R6;
C1-C22alkyl;
C2-C22alkenyl;
C2-C22alkinyl;
C3-C12cycloalkyl;
C3-C12cycloalkenyl;
C7-C20aralkyl;
C1-C20heteroalkyl;
C3-C12cyclo-heteroalkyl;
C3-C18heteroaralkyl;
C6-C20aryl;
C1-C12alkylcarbonylamino-C6-C20aryl;
C2-C12heteroaryl;
or —X2—Sil2;
if n=1,
R1 and R2 independently of each other are hydrogen;
C1-C22 alkyl;
hydroxy-C1-C22alkyl;
C2-C22alkenyl;
C2-C22alkinyl;
C3-C12cycloalkyl;
C3-C12cycloalkenyl;
C7-C20aralkyl;
C1-C20heteroalkyl;
C3-C12cycloheteroalkyl;
C6-C20aryl;
C3-C18heteroaralkyl;
C2-C12heteroaryl;
—(CH2)u—SiR8R9R10;
or —X1—Sil1;
if n=2,
R1 and R2 are each C1-C6alkylene;
or one of R1 and R2 is C1-C6alkylene and the other is as defined for n =1;
if n =4,
one of R1 and R2 is a tetravalent radical and the other is as defined as for n =1,
wherein the tetravalent radical is
R5 and R6 independently of each other are hydrogen;
C1-C22alkyl, C2-C22alkenyl, C2-C22alkinyl;
C3-C12cycloalkyl;
C3-C12cycloalkenyl;
C7-C20aralkyl;
COR7;
C1-C20hetero-alkyl;
C3-C12cycloheteroalkyl;
C3-C18heteroaralkyl;
C6-C20 aryl;
C1-C5alkoxy-C6-C20aryl;
—(CH2)t—SO3H;
—(CH2)v—(CO)—OR7;
—(CH2)t—O—C6-C10aryl;
C2-C12heteroaryl;
—(CH2)u—SiR8R9R10;
or a radical —X2—Sil2;
R7 is hydrogen;
C1-C22alkyl;
C2-C22alkenyl;
C2-C22alkinyl;
C3-C12cycloalkyl;
C3-C12cycloalkenyl;
C7-C20 aralkyl;
C1-C20heteroalkyl;
C3-C12cycloheteroalkyl;
C3-C18heteroaralkyl;
C6-C20aryl;
or C2-C12heteroaryl;
R8, R9, R10 independently form each other are C1-C22alkyl;
C6-C20aryl;
C1-C22alkoxy;
or O—C6-C20aryl;
and each alkyl, alkenyl, alkinyl, cycloalkyl or cycloalkylene group is unsubstituted or substituted by one or more R12;
and each aryl, heteroaryl, aralkyl, arylene, heteroarylene or aralkylene is unsubstituted or substituted by one or more R13;
R12 is halogen, OH;
NR16R17;
O—R16;
S—R16;
CO—R16;
O—CO—R16;
oxo;
thiono;
CN;
COOR16;
CONR16R17;
SO2NR16R17;
SO2R16;
SO3R16;
SiR8R9R10;
OSiR8R9R10;
POR8R9;
or a radical —X3—Sil3;
R13 is C1-C12alkylthio;
C3-C12cycloalkylthio;
C1-C12alkenylthio;
C3-C12cycloalkenylthio;
C1-C12alkoxy;
C3-C12cycloalkoxy;
C1-C12alkenyloxy;
or C3-C12cycloalkenyloxy which is unsubstituted or substituted by one or more R12;
halogen;
CN;
SH;
OH;
CHO;
R18;
OR18;
SR18;
C(R18)═CR19R20;
O—CO—R19;
NR18R19;
CONR18R19;
SO2NR18R19;
SO2R18;
COOR18, OCOOR18;
NR19COR20;
NR19COOR20;
SiR8R9R10;
OSiR8R9R10;
P(═O)R8R9;
or a radical —X4—Sil4;
R16, R17, R18, R19 and R20 independently of each other are hydrogen;
C1-C22alkyl;
C3-C12cycloalkyl;
C2-C12alkenyl;
C3-C12cycloalkenyl;
C6-C20aryl;
C2-C12heteroaryl;
C7-C18aralkyl;
or C3-C18heteroaralkyl;
R16 and R17 and/or R18 and R19 may be linked together to form unsubstituted or C1-C4alkyl-substituted pyrrolidine, piperidine, piperazine or morpholine;
X1, X3 and X4 independently from each other are a linker;
wherein the linker is a divalent radical of formula (5)
wherein
R21, R22, R23 and R24 independently form each other are hydrogen;
C1-C22alkyl;
C6-C20aryl;
C1-C22alkoxy;
or O—C6-C20aryl;
b is a number from 0 to 30;
c is a number from 0 to 6;
and
d is a number from 0 to 1;
Sil1, Sil3 and Sil4 independently from each other are a silane-, oligosiloxane or polysiloxane moiety;
t is a number from 0 to 12;
u is a number from 0 to 12;
and
v is a number from 0 to 12.

167 more elements

Dependencies are inferred from the claim text.

Facts

Application: 12/311,502Filed 5 Oct 2007
Priority: EP 0612222213 Oct 2006
Published: US 2010/0035839 A111 Feb 2010
Granted: 30 Jun 2015
Term ends: Not estimatedThe source records don’t support an estimate.

Classification16 codes

C09B 23/0066
Methine or polymethine dyes, e.g. cyanine dyes: the polymethine chain being part of a carbocyclic ring,
A61K 8/49
Containing organic compounds: containing heterocyclic compounds
A61K 8/4926
With one nitrogen as the only hetero atom: having six membered rings
A61K 8/494
Containing heterocyclic compounds: with more than one nitrogen as the only hetero atom

Family

US 2010/0035839 A1Pre-grant publication · published 11 Feb 2010
US 9,068,080 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

Merocyanine derivatives of formula (1)

wherein
L2 is hydrogen;
and L1 and L3 are linked together to form a carbocyclic ring;
R3 is —X2—Sil2, wherein Sil2 is a polysiloxane of the formula (4a) or (4b)
and
X2 is C1-C18alkylene;
or a bivalent radical of the formula (5a), (5b) or (5c)
wherein the asterix * is linked to Sil2 and the asterix ** is linked to R3 or R4;
and
w is a number from 0 to 30,
wherein
R8, R9, R10 independently form each other are C1-C22alkyl;
C6-C20aryl;
C1-C22alkoxy;
or O—C6-C20aryl;
A is a bond to X1 or X2;
x is a number from 4 to 250;
y is a number from 5 to 250;
and
z is a number from 1 to 50;
and
n is 1, 2, or 4;
R4 is CN;
—COR5;
—COOR5;
—CONR5R6;
C1-C22alkyl;
C2-C22alkenyl;
C2-C22alkinyl;
C3-C12cycloalkyl;
C3-C12cycloalkenyl;
C7-C20aralkyl;
C1-C20heteroalkyl;
C3-C12cyclo-heteroalkyl;
C3-C18heteroaralkyl;
C6-C20aryl;
C1-C12alkylcarbonylamino-C6-C20aryl;
C2-C12heteroaryl;
or —X2—Sil2;
if n=1,
R1 and R2 independently of each other are hydrogen;
C1-C22 alkyl;
hydroxy-C1-C22alkyl;
C2-C22alkenyl;
C2-C22alkinyl;
C3-C12cycloalkyl;
C3-C12cycloalkenyl;
C7-C20aralkyl;
C1-C20heteroalkyl;
C3-C12cycloheteroalkyl;
C6-C20aryl;
C3-C18heteroaralkyl;
C2-C12heteroaryl;
—(CH2)u—SiR8R9R10;
or —X1—Sil1;
if n=2,
R1 and R2 are each C1-C6alkylene;
or one of R1 and R2 is C1-C6alkylene and the other is as defined for n =1;
if n =4,
one of R1 and R2 is a tetravalent radical and the other is as defined as for n =1,
wherein the tetravalent radical is
R5 and R6 independently of each other are hydrogen;
C1-C22alkyl, C2-C22alkenyl, C2-C22alkinyl;
C3-C12cycloalkyl;
C3-C12cycloalkenyl;
C7-C20aralkyl;
COR7;
C1-C20hetero-alkyl;
C3-C12cycloheteroalkyl;
C3-C18heteroaralkyl;
C6-C20 aryl;
C1-C5alkoxy-C6-C20aryl;
—(CH2)t—SO3H;
—(CH2)v—(CO)—OR7;
—(CH2)t—O—C6-C10aryl;
C2-C12heteroaryl;
—(CH2)u—SiR8R9R10;
or a radical —X2—Sil2;
R7 is hydrogen;
C1-C22alkyl;
C2-C22alkenyl;
C2-C22alkinyl;
C3-C12cycloalkyl;
C3-C12cycloalkenyl;
C7-C20 aralkyl;
C1-C20heteroalkyl;
C3-C12cycloheteroalkyl;
C3-C18heteroaralkyl;
C6-C20aryl;
or C2-C12heteroaryl;
R8, R9, R10 independently form each other are C1-C22alkyl;
C6-C20aryl;
C1-C22alkoxy;
or O—C6-C20aryl;
and each alkyl, alkenyl, alkinyl, cycloalkyl or cycloalkylene group is unsubstituted or substituted by one or more R12;
and each aryl, heteroaryl, aralkyl, arylene, heteroarylene or aralkylene is unsubstituted or substituted by one or more R13;
R12 is halogen, OH;
NR16R17;
O—R16;
S—R16;
CO—R16;
O—CO—R16;
oxo;
thiono;
CN;
COOR16;
CONR16R17;
SO2NR16R17;
SO2R16;
SO3R16;
SiR8R9R10;
OSiR8R9R10;
POR8R9;
or a radical —X3—Sil3;
R13 is C1-C12alkylthio;
C3-C12cycloalkylthio;
C1-C12alkenylthio;
C3-C12cycloalkenylthio;
C1-C12alkoxy;
C3-C12cycloalkoxy;
C1-C12alkenyloxy;
or C3-C12cycloalkenyloxy which is unsubstituted or substituted by one or more R12;
halogen;
CN;
SH;
OH;
CHO;
R18;
OR18;
SR18;
C(R18)═CR19R20;
O—CO—R19;
NR18R19;
CONR18R19;
SO2NR18R19;
SO2R18;
COOR18, OCOOR18;
NR19COR20;
NR19COOR20;
SiR8R9R10;
OSiR8R9R10;
P(═O)R8R9;
or a radical —X4—Sil4;
R16, R17, R18, R19 and R20 independently of each other are hydrogen;
C1-C22alkyl;
C3-C12cycloalkyl;
C2-C12alkenyl;
C3-C12cycloalkenyl;
C6-C20aryl;
C2-C12heteroaryl;
C7-C18aralkyl;
or C3-C18heteroaralkyl;
R16 and R17 and/or R18 and R19 may be linked together to form unsubstituted or C1-C4alkyl-substituted pyrrolidine, piperidine, piperazine or morpholine;
X1, X3 and X4 independently from each other are a linker;
wherein the linker is a divalent radical of formula (5)
wherein
R21, R22, R23 and R24 independently form each other are hydrogen;
C1-C22alkyl;
C6-C20aryl;
C1-C22alkoxy;
or O—C6-C20aryl;
b is a number from 0 to 30;
c is a number from 0 to 6;
and
d is a number from 0 to 1;
Sil1, Sil3 and Sil4 independently from each other are a silane-, oligosiloxane or polysiloxane moiety;
t is a number from 0 to 12;
u is a number from 0 to 12;
and
v is a number from 0 to 12.

167 more elements

Facts

Application

12/311,502Filed 5 Oct 2007

Priority

EP 0612222213 Oct 2006

Published

US 2010/0035839 A111 Feb 2010

Granted

30 Jun 2015

Term ends

Not estimatedThe source records don’t support an estimate.

Classification16 codes

C09B 23/0066
Methine or polymethine dyes, e.g. cyanine dyes: the polymethine chain being part of a carbocyclic ring,
A61K 8/49
Containing organic compounds: containing heterocyclic compounds
A61K 8/4926
With one nitrogen as the only hetero atom: having six membered rings
A61K 8/494
Containing heterocyclic compounds: with more than one nitrogen as the only hetero atom