UV absorbing chromophores covalently bonded to hyperbranched polymers
AssigneeDsm IP Assets B.V.
InventorsAlexander Poschalko, Ulrich Huber, Volker Schehlmann
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Abstract
The invention provides a conjugate comprising a hyperbranched polymer covalently bonded to at least three UV absorbing chromophores having an UV absorption maximum λmax≧270 nm. The conjugate is an effective and safe sunscreen which can advantageously be used in cosmetic compositions.
Claims11
A cosmetic composition comprising a conjugate comprising a hyperbranched polymer covalently bonded to at least three UV absorbing chromophores having an UV absorption maximum λmax≧270 nm selected from the group consisting of the moieties represented by general formulae:
- wherein
- Y is O or NR3 wherein R3 is H, C1-C6-alkyl or C2-C6-alkenyl;
- R4 and R5 are independently H, C1-C6-alkyl, C2-C6-alkenyl, CO2H, CO2—C1-C6-alkyl, or R4 and R5 together with the carbon atom to which they are attached form a 6-camphenyl ring;
- R9 and R10 are independently H or C1-C6-alkyl;
- R11 and R12 are independently H, C1-C6-alkyl, NO2, CO2—C1-C6-alkyl or CN;
- Z is C1-C6-alkylene, optionally interrupted by 1 to 3 oxygen atoms;
- R13 and R14 are independently H, OR15, NR16R17 or C1-C6-alkyl;
- and
- R15, R16 and R17 are independently selected from H and C1-C6-alkyl;
- and
- wherein R′ is H, OH, straight or branched chain C1-C20-alkyl, C1-C20-alkoxy or C2-C20-alkenyl;
- and wherein in the above definition the symbol “┤” denotes the linkage to the hyperbranched polymer;
- or a moiety of benzophenone-3, benzophenone-4, 2,2′,4,4′-tetrahydroxy-benzophenone and 2,2′-dihydroxy-4,4′ dimethoxybenzophenone;
- and a cosmetically acceptable carrier, and wherein
- the hyperbranched polymer is the polycondensation or polyaddition reaction product of building blocks AB2, which building block AB2 is glycidol.
A cosmetic composition comprising a conjugate comprising a hyperbranched polymer covalently bonded to at least three UV absorbing chromophores having an UV absorption maximum λmax≧270 nm selected from the group consisting of the moieties represented by general formulae:
- wherein
- Y is O or NR3 wherein R3 is H, C1-C6-alkyl or C2-C6-alkenyl;
- R4 and R5 are independently H, C1-C6-alkyl, C2-C6-alkenyl, CO2H, CO2-C1-C6-alkyl, or R4 and R5 together with the carbon atom to which they are attached form 6-camphenyl ring;
- R9 and R10 are independently H or C1-C6alkyl;
- R11 and R12 are independently H, C1-C6-alkyl, NO2, CO2-C1-C6-alkyl or CN;
- Z is C1-C6-alkylene, optionally interrupted by 1 to 3 oxygen atoms;
- R13 and R14 are independently H, OR15, NR16R17 or C1-C6-alkyl;
- and
- R15, R16 and R17 are independently selected from H and C1-C6-alkyl;
- and
- wherein R′ is H, OH, straight or branched chain C1-C20-alkyl, C1-C20-alkoxy or C2-C20-alkenyl;
- and wherein in the above definition the sysmbol “┤” denotes the linkage to the hyperbranched polymer;
- or a moiety of benzophenone-3, benzophenone-4, 2,2′,4,4′-tetrahydroxy-benzophenone and 2,2′-dihydroxy-4,4′dimethoxybenzophenone;
- and a cosmetically acceptable carrier, wherein the hyperbrqanched polymer comprises a structure represented by general formula (II)
- {[(Bk)l (AB2)n](Y1)g}(LX)p(Y2)h (II),
- wherein
- Y1 and Y2 independently represent UV absorbing chromophores;
- (LX)p represents p linker units LX, wherein independently the distal end of each linker unit LX bears a functional group X either being covalently bonded to an UV absorbing chromophore Y2, or covalently bonded to a capping group, or in its free reactive form,
- and wherein the proximal end of each linker unit LX is covalently bonded to the hyperbranched polymer;
- and
- Bk represents a starter unit bearing k functional groups B, wherein independently each functional group B is
- covalently bonded to a functional group A of a building block AB2;
- or
- covalently bonded to the proximal end of a linker unit LX, or
- covalently bonded to an UV absorbing chromophore Y1, or
- covalently bonded to a capping group, or
- in its free reactive form;
- (AB2)n represents n building blocks AB2, which building block is glycidol, each bearing a functional group A which is the electrophillic carbon atom of the oxirane and 2 independent functional groups B which are represented by the alcoholate of deprotonated glycidol as well as the alcoholate deliberated upon ring opening, wherein independently each functional group A is
- covalently bonded to a functional group B
- of a further building block AB2, which building block is glycidol, or
- of the starter unit Bk, or
- covalently bonded to a capping group, or
- in its free reactive form,
- and wherein independently each functional group B is
- covalently bonded to a functional group A of a further building block AB2, which building block is glycidol, or
- covalently bonded to the proximal end of a linker unit LX, or
- covalently bonded to an UV absorbing chromophore Y1, or
- covalently bonded to a capping group, or
- in its free reactive form;
- wherein
- index g is an integer, wherein 0≦g≦100;
- index h is an integer, wherein 0≦h≦p, with the proviso that g+h≦3;
- index k is an integer of from 1 to 6;
- index l is 0 or 1;
- index n is an integer of from 3 to 100;
- and
- index p is an integer wherein 0≦p≦100.
Dependencies are inferred from the claim text.