(meth)acrylic silicone graft copolymer and a method for preparing the same

A method for preparing a (meth)acrylic silicone graft copolymer having a unit represented by the following formula (I), a unit represented by the following formula (II), a structure represented by the following formula (III) at one terminal and a structure represented by the following formula (IV) at the other terminal,

• wherein R1 and R6 are, independently of each other, a hydrogen atom or a methyl group, R7 is an alkyl group having 1 to 4 carbon atoms, R8 and R9 are, independently of each other, a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R10 is a hydrogen atom or a methyl group, B is an alkoxy group which has 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an amino group, a siloxy group, a halogen atom, a hydroxyl group or a substituted or unsubstituted, monovalent hydrocarbon group which has 1 to 20 carbon atoms and may have at least one selected from —O—, —S— and —NR—, wherein R is a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms, provided that the oxygen atom, the sulfur atom and the nitrogen atom are not adjacent to each other, and
• A is a group having a linear organopolysiloxane structure represented by the following formula (1) or a group having a dendritic organopolysiloxane structure represented by the following formula (2-1) or (2-2), X is a group as defined for A or B, an order of the units (I) and (II) is not limited, p is an integer of 1 or larger, q is an integer of 1 or larger, and p+q is the number such that the copolymer has a number average molecular weight of 1,000 to 1,000,000 g/mol,
• wherein Z is a divalent organic group, R2 is a saturated hydrocarbon group having 1 to 10 carbon atoms or a phenyl group, R3 is a saturated hydrocarbon group having 1 to 10 carbon atoms, and m is an integer of from 0 to 100,
• wherein Z is a divalent organic group, a is a number of 0 to 3, Q is a group represented by the following formula (2), D is a (3c+1)-valent organopolysiloxanyl group which has a hierachial order of c, 3c means 3 raised to the power of c, c is an integer of from 1 to 8,
• wherein R4 is a saturated hydrocarbon group having 1 to 10 carbon atoms or a phenyl group, R5 is a saturated hydrocarbon group having 1 to 6 carbon atoms or a phenyl group, R14 is a hydrogen atom, a saturated hydrocarbon group having 1 to 10 carbon atoms or a phenyl group, a2 is the number of 0 to 2, and n is an integer of from 2 to 12,
• wherein the method comprises a step of group transfer polymerization of a compound represented by the following general formula (4)
• and a compound represented by the following general formula (5),
• wherein R1, R6, A and B are as defined above,
• in the presence of a compound represented by the following general formula (6) as an initiator
• wherein R7, R8 and R9 are as defined above, R11, R12 and R13 are, independently of each other, an alkyl group having 1 to 4 carbon atoms,
• and further comprises a step of distilling off the monomers represented by the aforesaid formula (4) or (5) under a reduced pressure at a temperature of 100 degrees C. or higher after the group transfer polymerization.

A cosmetic comprising a (meth)acrylic silicone graft (co)polymer having a unit represented by the following formula (I), a structure represented by the following formula (III) at one terminal, and a structure represented by the following formula (IV) at the other terminal,

• wherein R1 is, independently of each other, a hydrogen atom or a methyl group, R7 is an alkyl group having 1 to 4 carbon atoms, R8 and R9 are, independently of each other, a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R10 is a hydrogen atom or a methyl group, A is a group having a linear organopolysiloxane structure represented by the following formula (1) or a group having a dendritic organopolysiloxane structure represented by the following formula (2-1) or (2-2), X′ is a group as defined for A, and p is an integer such that the (co)polymer has a number average molecular weight of 1,000 to 1,000,000 g/mol,
• wherein Z is a divalent organic group, R2 is a saturated hydrocarbon group having 1 to 10 carbon atoms or a phenyl group, R3 is a saturated hydrocarbon group having 1 to 10 carbon atoms, and m is an integer of from 0 to 100,
• wherein Z is a divalent organic group, a is a number of 0 to 3, Q is a group represented by the following formula (2), D is a (3c+1)-valent organopolysiloxanyl group which has a hierachial order of c, 3c means 3 raised to the power of c, c is an integer of from 1 to 8,
• wherein R4 is a saturated hydrocarbon group having 1 to 10 carbon atoms or a phenyl group, R5 is a saturated hydrocarbon group having 1 to 6 carbon atoms or a phenyl group, R14 is a hydrogen atom, a saturated hydrocarbon group having 1 to 10 carbon atoms or a phenyl group, a2 is the number of 0 to 2, and n is an integer of from 2 to 12.

A cosmetic comprising a (meth)acrylic silicone graft copolymer having a unit represented by the following formula (I), a unit represented by the following formula (II), a structure represented by the following formula (III) at one terminal and a structure represented by the following formula (IV) at the other terminal,

• wherein R1 and R6 are, independently of each other, a hydrogen atom or a methyl group, R7 is an alkyl group having 1 to 4 carbon atoms, R8 and R9 are, independently of each other, a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R10 is a hydrogen atom or a methyl group, B is an alkoxy group which has 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an amino group, a siloxy group, a halogen atom, a hydroxyl group or a substituted or unsubstituted, monovalent hydrocarbon group which has 1 to 20 carbon atoms and may have at least one selected from —O—, —S— and —NR—, wherein R is a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms, provided that the oxygen atom, the sulfur atom and the nitrogen atom are not adjacent to each other, and
• A is a group having a linear organopolysiloxane structure represented by the following formula (1) or a group having a dendritic organopolysiloxane structure represented by the following formula (2-1) or (2-2), X is a group as defined for A or B, an order of the units (I) and (II) is not limited, p is an integer of 1 or larger, q is an integer of 1 or larger, and p+q is the number such that the copolymer has a number average molecular weight of 1,000 to 1,000,000 g/mol,
• wherein Z is a divalent organic group, R2 is a saturated hydrocarbon group having 1 to 10 carbon atoms or a phenyl group, R3 is a saturated hydrocarbon group having 1 to 10 carbon atoms, and m is an integer of from 0 to 100,
• wherein Z is a divalent organic group, a is a number of 0 to 3, Q is a group represented by the following formula (2), D is a (3c+1)-valent organopolysiloxanyl group which has a hierachial order of c, 3c means 3 raised to the power of c, c is an integer of from 1 to 8,
• wherein R4 is a saturated hydrocarbon group having 1 to 10 carbon atoms or a phenyl group R5 is a saturated hydrocarbon group having 1 to 6 carbon atoms or a phenyl group, R14 is a hydrogen atom, a saturated hydrocarbon group having 1 to 10 carbon atoms or a phenyl group, a2 is the number of 0 to 2, and n is an integer of from 2 to 12.