Organopolysiloxane elastomer modified with mono-/diglycerin derivative, and use therefor

• US 9,585,832 B2
• Filed: 05/22/2012
• Issued: 03/07/2017
• Est. Priority Date: 05/30/2011
• Status: Expired due to Fees

• Current Assignee: Dow Toray Co., Ltd. (Dow, Inc.)
• Original Assignee: Dow Corning Toray Company Limited (Dow, Inc.)
• Inventors: Tamura, Seiki, Souda, Tatsuo, Hasegawa, Chiichiro, Kojima, Kazuhiko, Hori, Seiji
• Primary Examiner(s): GULLEDGE, BRIAN M
• Application Number:
  US14/122,692
• Publication Number:
  US 20140194532A1
• Time in Patent Office: 1,750 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: A61K 2800/10 General cosmetic use
• CPC Class Codes: A61K 47/34 Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers A61K47/10 takes precedence
• CPC Class Codes: A61K 8/0241 Containing particulates characterized by their shape and/or structure see also A61K8/04, A61K8/11, and A61K8/14, further aspects are classified in A61K2800/40 and subcodes
• CPC Class Codes: A61K 8/892 modified by a hydroxy group, e.g. dimethiconol
• CPC Class Codes: A61K 8/893 modified by an alkoxy or aryloxy group, e.g. behenoxy dimethicone or stearoxy dimethicone
• CPC Class Codes: A61K 8/895 containing silicon bound to unsaturated aliphatic groups, e.g. vinyl dimethicone
• CPC Class Codes: A61K 9/0014 Skin, i.e. galenical aspects of topical compositions non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00
• CPC Class Codes: A61K 9/107 Emulsions ; Emulsion preconcentrates; Micelles composition of emulsions A61K47/00
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: A61Q 19/007 Preparations for dry skin
• CPC Class Codes: A61Q 19/08 Anti-ageing preparations
• CPC Class Codes: A61Q 5/00 Preparations for care of the hair
• CPC Class Codes: C08G 77/12 containing silicon bound to hydrogen C08G77/045 takes precedence
• CPC Class Codes: C08G 77/46 containing polyether sequences
• CPC Class Codes: C08G 77/50 by carbon linkages C08G77/485 takes precedence
• CPC Class Codes: C08L 83/12 containing polyether sequences
• CPC Class Codes: C08L 83/14 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms C08L83/10 takes precedence
• CPC Class Codes: Y10T 428/2982 Particulate matter [e.g., sphere, flake, etc.]

Abstract

The present invention relates to a glycerin derivative-modified organopolysiloxane elastomer comprising:

• as a hydrophilic group, a glycerin derivative group in which an average number of repetitions of glycerin units is in a range of 1.0 to 2.4, being free of an oxyalkylene structure having an average number of repetitions of an oxyalkylene unit of 2 or higher; and
• a crosslinked three-dimensional net-like structure having a carbon-silicon bond in a crosslinking part.

Claims

1. A glycerin derivative-modified organopolysiloxane elastomer wherein:

the glycerin derivative-modified organopolysiloxane elastomer is obtained by reaction of;

(A) an organohydrogenpolysiloxane, wherein the organohydrogenpolysiloxane is selected from the group consisting of;

(i) R¹₃SiO(R¹₂SiO)_v(R¹SiHO)_wSiR¹₃,

(ii) HR¹₂SiO(R¹₂SiO)_v(R¹SiHO)_zSiR¹₃, and

(iii) HR¹₂SiO(R¹₂SiO)_v(R¹SiHO)_zSiR¹₂H,

wherein R¹ is each independently a monovalent organic group;

v is 0 or a positive integer;

w is a positive integer; and

z is 0 or a positive integer;

(B) a glycerin derivative group-containing organic compound having a reactive unsaturated group, wherein the glycerin derivative group-containing organic compound has a diglycerin derivative group represented by following general formula (5-1);

2. The glycerin derivative-modified organopolysiloxane elastomer according to claim 1, wherein the diglycerin derivative group is bonded to a silicon atom through a divalent linking group;

the glycerin derivative-modified organopolysiloxane elastomer further comprising;

another glycerin derivative group-containing organic group having an average number of repetitions of glycerin units in a range of 1.0 to 2.4, wherein the glycerin unit is at least one selected from the group consisting of glycerin units represented by the following structural formulae (4-1) to (4-3);

3. The glycerin derivative-modified organopolysiloxane elastomer according to claim 1, wherein:

average value of the number of silicon-bonded hydrogen atoms per single molecule of the component (A) reactive with the reactive unsaturated group of the component (C) constituting the crosslinking part is greater than or equal to 1.5.

4. The glycerin derivative-modified organopolysiloxane elastomer according to claim 1, wherein:

the monovalent organic group R¹ is selected from the group consisting of (D1) to (D9);

(D1) substituted or unsubstituted, straight or branched monovalent hydrocarbon groups having from 1 to 60 carbons;

(D2) a polyoxyalkylene group represented by —

R⁸O(AO)_zR⁹, wherein, AO represents an oxyalkylene group having from 3 to 4 carbons;

R⁸ represents a substituted or unsubstituted, straight or branched divalent hydrocarbon group having from 3 to 5 carbons;

R⁹ represents a substituted or unsubstituted, straight or branched monovalent hydrocarbon group having from 1 to 24 carbons, or a substituted or unsubstituted, straight or branched acyl group having from 2 to 24 carbons; and

z=1 to 100;

(D3) a substituted or unsubstituted, straight or branched alkoxy group having from 1 to 30 carbons;

(D4) a hydroxyl group;

(D5) an ester group represented by —

R¹⁰—

COOR¹¹, wherein, R¹⁰ represents a substituted or unsubstituted, straight or branched divalent hydrocarbon group having from 2 to 20 carbons; and

R¹¹ represents a substituted or unsubstituted, straight or branched monovalent hydrocarbon group having from 1 to 30 carbons;

(D6) an ester group represented by —

R¹²—

OCOR¹³, wherein, R¹² represents a substituted or unsubstituted, straight or branched divalent hydrocarbon group having from 2 to 20 carbons; and

R¹³ represents a substituted or unsubstituted, straight or branched monovalent hydrocarbon group having from 1 to 30 carbons;

(D7) an alkyl group substituted by a straight polysiloxane structure and represented by the following general formula (4);

5. The glycerin derivative-modified organopolysiloxane elastomer according to claim 1, wherein

the glycerin derivative-modified organopolysiloxane elastomer is in the form of particles.

6. The glycerin derivative-modified organopolysiloxane elastomer according to claim 5, wherein

volume average particle diameter of the particles is in a range of 20 to 1,000 μ

m.

7. The glycerin derivative-modified organopolysiloxane elastomer according to claim 1, wherein:

the glycerin derivative-modified organopolysiloxane elastomer is capable of swelling as a result of including a weight amount of an oil agent that is at least the weight of the glycerin derivative-modified organopolysiloxane elastomer itself.

8. A composition comprising:

the glycerin derivative-modified organopolysiloxane elastomer according to claim 1; and

at least one oil agent.

9. The composition according to claim 8, wherein the form of the composition is a paste.

10. The composition according to claim 8, wherein:

the composition is obtained by intermixing at least one oil agent after crushing the glycerin derivative-modified organopolysiloxane elastomer by use of mechanical force, or

by crushing a mixture of at least one oil agent and the glycerin derivative-modified organopolysiloxane elastomer, by use of mechanical force.

11. The composition according to claim 8, wherein the composition is an emulsion composition.

12. An external use preparation raw material comprising:

the glycerin derivative-modified organopolysiloxane elastomer according to claim 1.

13. The external use preparation raw material according to claim 12, wherein

the raw material is an agent selected from the group consisting of gelling agents, structuring agents, thickeners, texture modifiers, humectants, masking agents, surfactants, emulsifiers, coating agents, and powder dispersion stabilizers.

14. An external use preparation comprising the glycerin derivative-modified organopolysiloxane elastomer according to claim 1.

15. A method for producing the glycerin derivative-modified organopolysiloxane elastomer according to claim 1, the method comprising at least a step of reacting:

(A) an organohydrogenpolysiloxane, wherein the organohydrogenpolysiloxane is selected from the group consisting of;

(i) R¹₃SiO(R¹₂SiO)_v(R¹SiHO)_wSiR¹₃,

(ii) HR¹₂SiO(R¹₂SiO)_v(R¹SiHO)_zSiR¹₃, and

(iii) HR¹₂SiO(R¹₂SiO)_v(R¹SiHO)_zSiR¹₂H,

wherein R¹ is each independently a monovalent organic group;

v is 0 or a positive integer;

w is a positive integer; and

z is 0 or a positive integer;

(B) a glycerin derivative group-containing organic compound having a reactive unsaturated group, wherein the glycerin derivative group-containing organic compound has a diglycerin derivative group represented by following general formula (5-1);

16. The method for producing the glycerin derivative-modified organopolysiloxane elastomer according to claim 15, wherein

a part or the entire reaction having the component (A), the component (B), and the component (C) is performed in the presence of at least one solvent selected from the group consisting of (P-1) and (P-2):

(P-1);

an organic compound; and

(P-2);

a compound having a silicon atom.

17. The method for producing the glycerin derivative-modified organopolysiloxane elastomer according to claim 15, wherein

the component (A) and the component (B) are reacted beforehand, and thereafter the component (C) is added to perform a crosslinking reaction;

the method further comprising a step selected from the group consisting of;

reacting a component (Q) with the component (A) prior to a reaction between the component (A) and the component (B);

after reaction of the component (A) and the component (B), further reacting the (Q) component; and

after crosslinking by the component (C), further reacting the component (Q),

wherein

(Q) is a compound having one reactive unsaturated group in a single molecule, with the exception of the organic compounds that have at least one reactive unsaturated group and at least one epoxy group per single molecule.

18. The method for producing the glycerin derivative-modified organopolysiloxane elastomer according to claim 15, wherein

the component (A) and the component (C) are reacted beforehand for introducing a crosslinking part, and thereafter the component (B) is added and reacted;

the method further comprising a step selected from the group consisting of;

reacting a component (Q) with the component (A) prior to reaction between the component (A) and the component (C);

after reaction of the component (A) and the component (C), further reacting the component (Q); and

after reaction with the component (B), further reacting the component (Q),

wherein

(Q) is a compound having one reactive unsaturated group in a single molecule, with the exception of the organic compounds that have at least one reactive unsaturated group and at least one epoxy group per single molecule.

19. A method for producing a glycerin derivative-modified organopolysiloxane elastomer including the step of:

treating the glycerin derivative-modified organopolysiloxane elastomer obtained by the method according to claim 15, using at least one acidic inorganic salt having the following properties;

being a solid at 25°

C.,

being water soluble, and having a

pH at 25°

C. of an aqueous solution upon dissolving of 50 g in 1 L of ion exchanged water being less than or equal to 4.

20. The method for producing a glycerin derivative-modified organopolysiloxane elastomer according to claim 19,

wherein the acidic inorganic salt is at least one acidic inorganic salt comprising a hydrogen sulfate ion (HSO₄⁻

) and a monovalent cation (M+).

21. The method for producing a glycerin derivative-modified organopolysiloxane elastomer according to claim 19, wherein

the acidic inorganic salt is at least one selected from the group consisting of sodium hydrogen sulfate, potassium hydrogen sulfate, and ammonium hydrogen sulfate.

22. The method for producing a glycerin derivative-modified organopolysiloxane elastomer according to claim 19, wherein a

utilized amount of the acidic inorganic salt relative to the glycerin derivative-modified organopolysiloxane elastomer is in a range of 100 ppm to 10,000 ppm.

23. The method for producing a glycerin derivative-modified organopolysiloxane elastomer according to claim 19, wherein

the treatment step using the acidic inorganic salt is performed in the presence of water and/or a hydrophilic medium.

24. The method for producing a glycerin derivative-modified organopolysiloxane elastomer according to claim 19, the method further comprising a step of removing low-boiling components by heating or reducing pressure after the treatment step using the acidic inorganic salt.

25. The method for producing a glycerin derivative-modified organopolysiloxane elastomer according to claim 19, the method further comprising a step of neutralizing by addition of at least one basic substance after the treatment step using the acidic inorganic salt.