Partially hydrocarbon group-blocked (poly)glycerol-modified polysiloxane, method for producing the same, and cosmetic composition containing the same
View Patent ↗The present invention provides a novel modified-polysiloxane, method for producing the same, and a cosmetic containing the same. The aforementioned modified-polysiloxane exhibits a reduced viscosity and superior operationability as compared with conventional polyoxyalkylene-modified polysiloxanes and polyglycerol-modified polysiloxanes. In addition, since the modified-polysiloxane is hardly oxidized in air, hardly produce allergenic compounds such as formates, and aldehydes such as formaldehyde, during storage over time, an increased environmental compatibility can be exhibited. In addition, the modified-polysiloxane of the present invention exhibits a reduced hydrolysis property and is stable. In the modified-polysiloxane of the present invention, the terminal hydroxyl groups of a polyglycerol-modified polysiloxane are partially blocked with hydrocarbon groups.
1. A partially hydrocarbon group-blocked (poly)glycerol-modified polysiloxane in which at least one terminal group is represented by formula (1), (2), or (3):
in each of the formulae, X represents a hydrogen atom or independently represents a substituted or non-substituted monovalent hydrocarbon group containing no aliphatic unsaturated bond, with not more than 20 carbon atoms;
wherein at least 15% of the Xs of the terminal groups are the hydrocarbon group, and
wherein the at least one terminal group binds to a silicon atom of an organopolysiloxane via a linking group comprising a poly(glycidol) moiety.
2. The partially hydrocarbon group-blocked (poly) glycerol-modified polysiloxane according to claim 1 , wherein the linking group contains a divalent group represented by general formula (4):
—R 1 —O-(AO) p — (4)
wherein
R 1 represents a substituted or non-substituted, linear or branched alkylene group having 1 to 22 carbon atoms, or a substituted or non-substituted alkylenearylene group having 6 to 22 carbon atoms;
AO independently represents an alkyleneoxy group having 1 to 4 carbon atoms, or an aryleneoxy group having 6 to 10 carbon atoms; and
p represents a number ranging from 0 to 30; with the proviso that R 1 binds to a silicon atom,
or a divalent group represented by general formula (5):
—R 1 —COO-(AO) p — (5)
wherein
R 1 , AO and p are the same as described above.
3. The partially hydrocarbon group-blocked (poly) glycerol-modified polysiloxane according to claim 2 , wherein the linking group further contains at least one moiety represented by formula (6), (7), (8) or (9):
wherein X is the same as described above.
4. The partially hydrocarbon group-blocked (poly)glycerol-modified polysiloxane according to claim 3 , wherein the moiety is present in an amount ranging from 1 to 500 moieties in the linking group.
5. The partially hydrocarbon group-blocked (poly)glycerol-modified polysiloxane according to claim 1 , wherein the partially hydrocarbon group-blocked (poly)glycerol-modified polysiloxane is represented by average unit formula (10):
R 2 a (R 3 ) b SiO (4-a-b)/2 (10)
wherein
R 2 represents a substituted or non-substituted monovalent hydrocarbon group containing no aliphatic unsaturated bond;
R 3 represents a partially hydrocarbon group-blocked (poly)glycerol-modified group represented by —R 4 —R 5 , wherein R 4 represents the linking group; and R 5 represents the terminal group; and
1.0≦a≦2.5, and 0.001≦b≦1.5.
6. A method for producing a partially hydrocarbon group-blocked (poly)glycerol-modified polysiloxane of claim 1 , the method comprising
reacting an organohydrogenpolysiloxane and a partially hydrocarbon group-blocked (poly)glycerol in which at least one terminal group represented by formula (1), (2) or (3):
in each of the formulae, X represents a hydrogen atom or independently represents a substituted or non-substituted monovalent hydrocarbon group containing no aliphatic unsaturated bond, with not more than 20 carbon atoms; and at least 15% of the Xs of the terminal groups are the hydrocarbon group, and
wherein the at least one terminal group binds to an aliphatic unsaturated hydrocarbon group via a linking group comprising a poly(glycidol) moiety,
in the presence of an addition reaction catalyst.
7. The method for producing a partially hydrocarbon group-blocked (poly)glycerol-modified polysiloxane according to claim 6 , wherein the linking group contains a divalent group represented by general formula (4′):
—R 6 —O-(AO) p — (4′)
wherein
R 6 represents a substituted or non-substituted, linear or branched alkylene group having 1 to 20 carbon atoms, or a substituted or non-substituted alkylenearylene group having 6 to 20 carbon atoms;
AO independently represents an alkyleneoxy group having 1 to 4 carbon atoms, or an aryleneoxy group having 6 to 10 carbon atoms; and
p represents a number ranging from 0 to 30; with the proviso that R 6 binds to the aliphatic unsaturated hydrocarbon group,
or a divalent group represented by general formula (5′):
—R 6 —COO-(AO) p — (5′)
wherein
R 6 , AO, and p are the same as described above.
8. The method for producing a partially hydrocarbon group-blocked (poly)glycerol-modified polysiloxane according to claim 7 , wherein the linking group further contains at least one moiety represented by formula (6), (7), (8) or (9):
wherein X is the same as described above.
9. The method for producing a partially hydrocarbon group-blocked (poly) glycerol-modified polysiloxane according to claim 6 , wherein the organohydrogenpolysiloxane is represented by average unit formula (II):
R 2 a H b SiO (4-a-b )/ 2 (11)
wherein
R 2 represents a substituted or non-substituted monovalent hydrocarbon group containing no aliphatic unsaturated bond; and
1.0≦a≦2.5, and 0.001≦b≦1.5.
10. The method for producing a partially hydrocarbon group-blocked (poly)glycerol-modified polysiloxane according to claim 6 , wherein the aliphatic unsaturated hydrocarbon group is a vinyl group or an allyl group.
11. A cosmetic comprising the partially hydrocarbon group-blocked (poly)glycerol-modified polysiloxane as recited in claim 1 .