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US 2009/0264657 A1Published application
Stabilization of body-care and household products against degradation by uv radiation using merocyanine derivatives
AssigneeBASF SE
InventorsBarbara Wagner, Oliver Reich
Life of this patent
Estimating the term…
Abstract
Described is the use of specific merocyanine derivatives for protecting body-care and household products from photolytic and oxidative degradation. These compounds perform outstanding UV absorber properties.
Claims27
A method for protecting body-care and household products from photolytic and oxidative degradation wherein said method comprises adding to said body-care and household products an effective amount of at least one stabilizer of formula
- wherein
- L1, L2 or L3 independently of each other hydrogen;
- hydroxy;
- C1-C22alkyl;
- C1-C22alkoxy;
- C2-C22alkenyl;
- C2-C22alkynyl;
- C3-C12cycloalkyl;
- C3-C12cycloalkenyl;
- C7-C20aralkyl;
- C1-C20heteroalkyl;
- C3-C12cycloheteroalkyl, C5-C11heteroaralkyl;
- C6-C20aryl;
- C6-C20aryl-C1-C5alkenylene;
- C4-C9heteroaryl;
- CN;
- —(CH2)t—OR9;
- or COOR9;
- R4 is CN;
- —COR7;
- —COOR7;
- —SO2R7;
- —CONR7R8;
- C1-C22alkyl;
- C2-C22alkenyl;
- C2-C22alkynyl;
- C3-C12cycloalkyl;
- C3-C12cycloalkenyl;
- C7-C20aralkyl;
- C1-C20heteroalkyl;
- C3-C12cycloheteroalkyl;
- C5-C11heteroaralkyl;
- C6-C20aryl;
- C1-C1alkylcarbonylamino-C6-C20aryl;
- C4-C9heteroaryl;
- R5, R6, R7 and R8 are independently of each other hydrogen;
- C1-C22alkyl, C2-C22alkenyl, C2-C22alkynyl;
- C3-C12cycloalkyl;
- C3-C12cycloalkenyl;
- C7-C20aralkyl;
- COR9;
- —(CO)—COO—R9;
- C1-C20 heteroalkyl;
- C3-C12cycloheteroalkyl;
- C5-C11heteroaralkyl;
- C6-C20aryl;
- C1-C5alkoxy-C6-C20aryl;
- —(CH2)t—SO3H;
- —(CH2)t—(CO)—OR9;
- —(CH2)t—O—C6-C10aryl;
- —(CH2)vCOO—R9;
- C4-C9heteroaryl;
- —(CH2)n—SiR15R16R17;
- or a radical —X-Sil;
- R9 is hydrogen;
- C1-C22alkyl;
- C2-C22alkenyl;
- C2-C22alkynyl;
- C3-C12cycloalkyl;
- C3-C12cycloalkenyl;
- C7-C20 aralkyl;
- C1-C20heteroalkyl;
- C3-C12cycloheteroalkyl;
- C5-C11heteroaralkyl;
- C6-C20aryl;
- or C4-C9heteroaryl;
- or
- L1 and L2, L1 and L3, L2 and L3, L1, and R4, L2 and R4, L1, and R1, L2 and R1, L3 and R1, L3 and R5, R3 and R4, R1 and R2, R7 and R8, R5 and R6 may be linked together to form 1, 2, 3 or 4 carbocyclic or N, O and/or S-heterocyclic rings, which may be further fused with other aromatic rings and each N in a N-heterocyclic ring may be unsubstituted or substituted by R10;
- and each alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylene group may be unsubstituted or substituted by one or more R11;
- and each aryl, heteroaryl, aralkyl, arylene, heteroarylene or aralkylene may be unsubstituted or substituted by one or more R12;
- R10 is R13;
- COR13;
- COOR13;
- or CONR13R14;
- R11 is halogen, OH;
- NR15R16;
- O—R15;
- S—R15;
- O—CO—R15;
- CO—R15;
- oxo;
- thiono;
- CN;
- COOR15;
- CONR15R16;
- SO2NR15R16;
- SO2R15;
- SO3R15;
- SiR15R16R17;
- OSiR15R16R17;
- POR15R16;
- or a radical —X-Sil;
- R12 is C1-C12alkylthio;
- C3-C12cycloalkylthio;
- C1-C12alkenylthio;
- C3-C12cycloalkenylthio;
- C1-C12alkoxy;
- C3-C12cycloalkoxy;
- C1-C12alkenyloxy;
- or C3-C12cycloalkenyloxy which may be unsubstituted or substituted by one or more R11;
- halogen;
- CN;
- SH;
- OH;
- CHO;
- R18;
- OR18;
- SR18;
- C(R18)═CR19R20;
- O—CO—R19;
- NR18R19;
- CONR18R19;
- SO2NR18R19;
- SO2R18;
- COOR18, OCOOR18;
- NR18COR19;
- NR19COOR20;
- SiRi5R16R17;
- OSiR15R16R17;
- P(═O)R19R20;
- or a radical —X-Sil;
- R13, R14, R15, R16, R17, R18, R19 and R20 independently of each other are hydrogen;
- C1-C22alkyl;
- C3-C12cycloalkyl;
- C2-C12alkenyl;
- C3-C12cycloalkenyl;
- C6-C14aryl;
- C4-C12heteroaryl;
- C7-C18aralkyl;
- or C5-C16heteroaralkyl;
- or
- R13 and R14, R15 and R16, R16 and R17 and/or R18 and R19 may be linked together to form unsubstituted or C1-C4alkyl-substituted pyrrolidine, piperidine, piperazine or morpholine;
- X is a linker;
- and
- Sil is a silane-, oligosiloxane or polysiloxane moiety;
- t is a number from 0 to 12;
- u is a number from 1 to 12;
- v is a number from 0 to 12;
- if n=1
- R1 and R2 independently of each other hydrogen;
- C1-C22 alkyl;
- hydroxy-C1-C22alkyl;
- C2-C22alkenyl;
- C2-C22alkynyl;
- C3-C12cycloalkyl;
- C3-C12cycloalkenyl;
- C7-C20aralkyl;
- C1-C20heteroalkyl;
- C3-C12cycloheteroalkyl;
- C6-C20aryl;
- C5-C11heteroaralkyl;
- C4-C9heteroaryl;
- or a radical of formula
- R21, R22, R23 independently from each other are C1-C22alkyl;
- or C1-C22alkoxy;
- a is the bond to the linker X;
- R3 is CN;
- NR5R6;
- —COR5;
- —COOR5;
- —SO2R5;
- —CONR5R6;
- C6-C20aryl;
- or C4-C9heteroaryl;
- p is a number from 0 to 100
- q is a number from 1 to 20;
- s is a number from 0 to 4;
- if n=2
- R1 and R2 are each a bivalent radical selected from C1-C5alkylene which may be interrupted by one or more oxygen atoms;
- or
- R1 and R2 together with the nitrogen atoms form a six-membered heterocyclic ring;
- and simultaneously R3 is defined as for n=1;
- or
- R3 is a bivalent radical of formula —CO—V1—C1-C12alkylene-W1-*, wherein
- the asterix indicates the bond to the second R3
- V1 is —O—;
- or —NR7—;
- or the direct bond;
- W1 is the linkage to the second R3, wherein W1 is the direct bond;
- or selected from C1-C12alkylene;
- or phenylene;
- and
- R1 and R2 simultaneously are defined as for n=1;
- if n=3
- one of R1, R2 or R3 is a trivalent radical;
- if n=4
- R1 or R2 is a radical of formula
- wherein
- the asterices indicate the bond to the second, third and fourth R1/R2;
- W2 is
- R3 is defined as for n=1;
- or
- R3 is a radical of formula
- wherein the asterices indicate the bond to the second (2), third (3) and fourth (4) R3;
- and
- W3 is
- or
- R1 or R2 is a radical of formula
- the asterices indicate the bond to the second, third and fourth R1/R2;
- R24 is C1-C22alkyl;
- or C1-C22alkoxy.
198 more elements
26-27. (canceled)
Compounds of formula
- wherein
- R3 is CN;
- NR5R6;
- —COR5;
- —COOR5;
- —SO2R5;
- —CONR5R6;
- C6-C20aryl;
- or C4-C9heteroaryl;
- R4 is CN;
- —COR7;
- —COOR7;
- —CONR7R8;
- C1-C22alkyl;
- C2-C22alkenyl;
- C2-C22 alkynyl;
- C3-C12cycloalkyl;
- C3-C12cycloalkenyl;
- C7-C20aralkyl;
- C1-C20heteroalkyl;
- C3-C12cycloheteroalkyl;
- C5-C11heteroaralkyl;
- C6-C20aryl;
- C1-C1alkylcarbonylamino-C6-C20aryl;
- or C4-C9heteroaryl;
- R5, R6, R7 and R8 are independently of each other hydrogen;
- C1-C22alkyl, C2-C22alkenyl, C2-C22alkynyl;
- C3-C12cycloalkyl;
- C3-C12cycloalkenyl;
- C7-C20aralkyl;
- COR9;
- —(CO)—COO—R9;
- C1-C20 heteroalkyl;
- C3-C12cycloheteroalkyl;
- C5-C11heteroaralkyl;
- C6-C20aryl;
- C1-C5alkoxy-C6-C20aryl;
- —(CH2)t—SO3H;
- —(CH2)t—(CO)—OR9;
- —(CH2)t—O—C6-C10aryl;
- —(CH2)nCOO—R9;
- C4-C9heteroaryl;
- —(CH2)n—SiR15R16R17;
- or a radical —X-Sil;
- R9 is hydrogen;
- C1-C22alkyl;
- C2-C22alkenyl;
- C2-C22alkynyl;
- C3-C12cycloalkyl;
- C3-C12cycloalkenyl;
- C7-C20 aralkyl;
- C1-C20heteroalkyl;
- C3-C12cycloheteroalkyl;
- C5-C11heteroaralkyl;
- C6-C20aryl;
- or C4-C9heteroaryl;
- or
- L1 and L3, are H or may be linked together to form 1, 2, 3 or 4 carbocyclic or N, O and/or S-heterocyclic rings, which may be further fused with other aromatic rings and each N in a N-heterocyclic ring may be unsubstituted or substituted by R10;
- and each alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylene group may be unsubstituted or substituted by one or more R11;
- and each aryl, heteroaryl, aralkyl, arylene, heteroarylene or aralkylene may be unsubstituted or substituted by one or more R12;
- R10 is R13;
- COR13;
- COOR13;
- or CONR13R14;
- R11 is halogen, OH;
- NR15R16;
- O—R15;
- S—R15;
- CO—R15;
- oxo;
- thiono;
- CN;
- COOR15;
- CONR15R16;
- SO2NR15R16;
- SO2R15;
- SO3R15;
- SiR15R16R17;
- OSiR15R16R17;
- POR15R16;
- or a radical —X-Sil;
- R12 is C1-C12alkylthio;
- C3-C12cycloalkylthio;
- C1-C12alkenylthio;
- C3-C12cycloalkenylthio;
- C1-C12alkoxy;
- C3-C12cycloalkoxy;
- C1-C12alkenyloxy;
- or C3-C12cycloalkenyloxy which may be unsubstituted or substituted by one or more R11;
- halogen;
- CN;
- SH;
- OH;
- CHO;
- R18;
- OR18;
- SR18;
- C(R18)═CR19R20;
- O—CO—R19;
- NR18R19;
- CONR18R19;
- SO2NR18R19;
- SO2R18;
- COOR18, OCOOR18;
- NR18COR19;
- NR19COOR20;
- SiR15R16R17;
- OSiR15R16R17;
- P(═O)R19R20;
- or a radical —X-Sil;
- R13, R14, R15, R16, R17, R18, R19 and R20 independently of each other are hydrogen;
- C1-C22alkyl;
- C3-C12cycloalkyl;
- C2-C12alkenyl;
- C3-C12cycloalkenyl;
- C6-C14aryl;
- C4-C12heteroaryl;
- C7-C18aralkyl;
- or C5-C16heteroaralkyl;
- or
- R13 and R14, R15 and R16, R16 and R17 and/or R18 and R19 may be linked together to form unsubstituted or C1-C4alkyl-substituted pyrrolidine, piperidine, piperazine or morpholine;
- X is a linker;
- and
- Sil is a silane-, oligosiloxane or polysiloxane moiety;
- t is a number from 0 to 12;
- u is a number from 1 to 12;
- v is a number from 0 to 12;
- if n=1
- R1 and R2 independently of each other hydrogen;
- C1-C22 alkyl;
- hydroxy-C1-C22alkyl;
- C2-C22alkenyl;
- C2-C22alkynyl;
- C3-C12cycloalkyl;
- C3-C12cycloalkenyl;
- C7-C20aralkyl;
- C1-C20heteroalkyl;
- C3-C12cycloheteroalkyl;
- C6-C20aryl;
- C5-C11heteroaralkyl;
- C4-C9heteroaryl;
- or a radical of formula
- R21, R22, R23 independently from each other are C1-C22alkyl;
- or C1-C22alkoxy;
- p is a number from 0 to 100
- q is a number from 1 to 20;
- s is a number from 0 to 4;
- R3 is CN;
- NR5R6;
- —COR5;
- —COOR5;
- —SO2R5;
- —CONR5R6;
- C6-C20aryl;
- or C4-C9heteroaryl;
- if n=2
- R1 and R2 are each a bivalent radical selected from C1-C5alkylene which may be interrupted by one or more oxygen atoms;
- or
- R1 and R2 together with the nitrogen atoms form a six-membered heterocyclic ring;
- and simultaneously R3 is defined as for n=1;
- or
- R3 is a bivalent radical of formula —CO—V1—C1-C12alkylene-W1-*, wherein the asterix indicates the bond to the second R3
- V1 is —O—;
- or —NR7—;
- or the direct bond;
- W1 is the linkage to the second R3, wherein W1 is the direct bond;
- or selected from C1-C12alkylene;
- or phenylene;
- and
- R1 and R2 simultaneously are defined as for n=1;
- if n=3
- one of R1, R2 or R3 is a trivalent radical;
- if n=4
- R1 or R2 is a radical of formula
- wherein the asterices indicate the bond to the second, third and fourth R1/R2;
- W2 is
- R3 is defined as for n=1;
- or
- R3 is a radical of formula
- wherein the asterices indicate the bond to the second (2), third (3) and fourth (4) R3;
- and
- W3 is
- or
- R1 or R2 is a radical of formula
- the asterices indicate the bond to the second, third and fourth R1/R2;
- R24 is C1-C22alkyl;
- or C1-C22alkoxy;
- wherein at least one of the radicals R1, R2, R3 or R4 is a silicon organic compound.
185 more elements
Dependencies are inferred from the claim text.