# US 2014/0194532 A1 · Organopolysiloxane Elastomer Modified With Mono-/Diglycerin Derivative, And Use Therefor > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2014/0194532 A1 - Document ID: US20140194532A1 - Status: Published application - Kind: A1 - Application number: 14/122,692 - Filed: 2012-05-22 - Published: 2014-07-10 - Earliest claimed: 2011-05-30 - Assignees: Dow Corning Toray Co., Ltd. - Inventors: Seiki Tamura; Tatsuo Souda; Chiichiro Hasegawa; Kazuhiko Kojima; Seiji Hori - Web page: https://patentgrep.com/patent/US20140194532A1 ## CPC - A61K 8/892: modified by a hydroxy group, e.g. dimethiconol - 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)} - A61K 8/893: modified by an alkoxy or aryloxy group, e.g. behenoxy dimethicone or stearoxy dimethicone - A61K 8/895: containing silicon bound to unsaturated aliphatic groups, e.g. vinyl dimethicone - 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)} - A61K 9/107: Emulsions {; Emulsion preconcentrates; Micelles (composition of emulsions A61K47/00)} - 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) - A61Q 5/00: Preparations for care of the hair - A61Q 19/00: Preparations for care of the skin - A61Q 19/007: {Preparations for dry skin} - A61Q 19/08: Anti-ageing preparations - C08G 77/46: containing polyether sequences - C08G 77/50: by carbon linkages - C08L 83/12: containing polyether sequences - 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) - A61K 2800/10: General cosmetic use - C08G 77/12: containing silicon bound to hydrogen - Y10T 428/2982: Particulate matter [e.g., sphere, flake, etc.] - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION ## 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 ### Claim 1 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 greater; and a crosslinked three-dimensional net-like structure having a carbon-silicon bond in a crosslinking part. ### Claim 2 (depends on 1) The glycerin derivative-modified organopolysiloxane elastomer according to claim 1, wherein the glycerin derivative group is bonded to a silicon atom through a divalent linking group; the glycerin derivative-modified organopolysiloxane elastomer further comprising: a 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 type selected from the group consisting of glycerin units represented by the following structural formulae (4-1) to (4-3): wherein, W is a hydrogen atom or an alkyl group having from 1 to 20 carbons; wherein, W is synonymous with the groups described above; and and, the glycerin derivative group-containing organic group does not have as a hydrophilic group an oxyalkylene structure having an average number of repetitions of an oxyalkylene unit of 2 or greater. ### Claim 3 (depends on 1) The glycerin derivative-modified organopolysiloxane elastomer according to claim 1, wherein: the glycerin derivative group is selected from the group consisting of the following: a diglycerin derivative group represented by following general formula (5-1): wherein, R17 represents a divalent organic group not having an oxyalkylene structure having an average number of repetitions of an oxyalkylene unit of 2 or greater; a diglycerin derivative group represented by following general formula (5-2): wherein, R17 is synonymous with the groups described above; and a mono-glycerin derivative group represented by following general formula (5-3): wherein, R17 is synonymous with the groups described above. ### Claim 4 (depends on 1) The glycerin derivative-modified organopolysiloxane elastomer according to claim 1, wherein: the glycerin derivative-modified organopolysiloxane elastomer is obtained by reaction of: (A) an organohydrogenpolysiloxane; (B) a glycerin derivative group-containing organic compound having a reactive unsaturated group; and (C) at least one type of organic compound selected from the group consisting of: (C1) organic compounds having an average of greater than one reactive unsaturated group per single molecule, and (C2) organic compounds having at least one reactive unsaturated group and at least one epoxy group per single molecule. ### Claim 5 (depends on 4) The glycerin derivative-modified organopolysiloxane elastomer according to claim 4, 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. ### Claim 6 (depends on 4) The glycerin derivative-modified organopolysiloxane elastomer according to claim 4, wherein: the component (A) is represented by the average composition formula (1): R1aHbSiO(4-a-b)/2 (1) wherein, R1 is each independently a monovalent organic group, 1.0≦a≦3.0, and 0.001≦b≦1.5. ### Claim 7 (depends on 4) The glycerin derivative-modified organopolysiloxane elastomer according to claim 4, wherein: the component (C) is at least one type of organic compound selected from the group consisting of (C-1) to (C-4), (C2-1), and (C2-2): (C1-1) an α,ω-diene represented by the general formula (2-1): CH2═CH(CH2)xCH═CH2 (2-1) wherein, 1≦x≦20; (C1-2) an α,ω-diyne represented by the general formula (2-2): CH≡C(CH2)xC≡CH (2-2) wherein, 1≦x≦20; (C1-3) an α,ω-ene-yne represented by the general formula (2-3): CH2═CH(CH2)xC≡CH (2-3) wherein, 1≦x≦20; (C1-4) a bis-alkenyl polyether compound represented by general formula (2-4): CmH2m-1O(CnH2nO)yCmH2m-1 (2-4) wherein, 2≦m≦20, 3≦n≦4, y is the total number of repetition of oxypropylene units or oxybutylene units, and 1≦y≦180; (C1-4) an unsaturated group-containing silicone compound represented by average composition formula (2-5): R2pR3qSiO(4-p-q)/2 (2-5) wherein, R2 may each independently be a monovalent organic group that is different from R3, R3 is each independently a monovalent unsaturated aliphatic hydrocarbon group having from 2 to 30 carbons, 1.0≦p≦2.5, and 0.001≦q≦1.5; (C2-1) an unsaturated epoxy compound represented by general formula (2-6): wherein, R4 has one reactive unsaturated group and represents a substituted or unsubstituted, straight or branched monovalent hydrocarbon group having from 2 to 20 carbons; and (C2-2) an unsaturated group-containing cycloaliphatic epoxy compound represented by general formula (2-7): wherein, R5 has one reactive unsaturated group and represents a substituted or unsubstituted, straight or branched monovalent hydrocarbon group having from 2 to 20 carbons, R6 represents a hydrogen atom or methyl group, and R7 represents a hydrogen atom or methyl group. ### Claim 8 (depends on 6) The glycerin derivative-modified organopolysiloxane elastomer according to claim 6, wherein: the monovalent organic group R1 in the average composition formula (1) 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): wherein, R14 is each independently a substituted or unsubstituted, straight or branched monovalent hydrocarbon group having from 1 to 30 carbons, a hydroxyl group, or hydrogen atom, at least one of the R14 moieties being the monovalent hydrocarbon group; t is a number in a range of 2 to 10; and r is a number in a range of 1 to 100; (D8) an epoxy group represented by the following general formula (5): wherein, R15 represents a substituted or unsubstituted, straight or branched divalent hydrocarbon group having from 2 to 20 carbons; and (D9) an alicyclic epoxy group represented by the following general formula (6): wherein, R16 represents a substituted or unsubstituted, straight or branched divalent hydrocarbon group having from 2 to 20 carbons; and R6 and R7 are synonymous with those described above. ### Claim 9 (depends on 1) The glycerin derivative-modified organopolysiloxane elastomer according to claim 1, wherein the glycerin derivative-modified organopolysiloxane elastomer is in the form of particles. ### Claim 10 (depends on 9) The glycerin derivative-modified organopolysiloxane elastomer according to claim 9, wherein volume average particle diameter of the particles is in a range of 20 to 1,000 μm. ### Claim 11 (depends on 1) 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. ### Claim 12 (depends on 1) A composition comprising: the glycerin derivative-modified organopolysiloxane elastomer described in claim 1; and at least one type of oil agent. ### Claim 13 (depends on 12) The composition according to claim 12, wherein the form of the composition is a paste. ### Claim 14 (depends on 12) The composition according to claim 12, wherein: the composition is obtained by intermixing at least one type of oil agent after crushing the glycerin derivative-modified organopolysiloxane elastomer by use of mechanical force, or by crushing a mixture of at least one type of oil agent and the glycerin derivative-modified organopolysiloxane elastomer, by use of mechanical force. ### Claim 15 (depends on 12) The composition according to claim 12, wherein the composition is an emulsion composition. ### Claim 16 (depends on 1) An external use preparation raw material comprising: the glycerin derivative-modified organopolysiloxane elastomer according to claim 1. ### Claim 17 (depends on 16) The external use preparation raw material according to claim 16, 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. ### Claim 18 (depends on 1) An external use preparation comprising the glycerin derivative-modified organopolysiloxane elastomer according to claim 1. ### Claim 19 (depends on 1) 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; (B) an glycerin derivative group-containing organic compound having a reactive unsaturated group; and (C) at least one type of organic compound selected from the group consisting of: (C1) organic compounds having an average of greater than one reactive unsaturated group per single molecule, and (C2) organic compounds having at least one reactive unsaturated group and at least one epoxy group per single molecule. ### Claim 20 (depends on 19) The method for producing the glycerin derivative-modified organopolysiloxane elastomer according to claim 19, 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. ### Claim 21 (depends on 19) The method for producing the glycerin derivative-modified organopolysiloxane elastomer according to claim 19, 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 an optional 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 optional (Q) component; and after crosslinking by the component (C), further reacting the optional component (Q): (Q): a compound having one reactive unsaturated group in a single molecule, with the exception of the organic compounds of (C2). ### Claim 22 (depends on 19) The method for producing the glycerin derivative-modified organopolysiloxane elastomer according to claim 19, 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 an optional 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 optional component (Q); and after reaction with the component (B), further reacting the optional component (Q): (Q): a compound having one reactive unsaturated group in a single molecule, with the exception of the organic compounds of (C2). ### Claim 23 (depends on 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 19, 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. ### Claim 24 (depends on 23) The method for producing a glycerin derivative-modified organopolysiloxane elastomer according to claim 23, wherein the acidic inorganic salt is at least one type of acidic inorganic salt comprising a hydrogen sulfate ion (HSO4−) and a monovalent cation (M+). ### Claim 25 (depends on 23) The method for producing a glycerin derivative-modified organopolysiloxane elastomer according to claim 23, wherein the acidic inorganic salt is at least one type selected from the group consisting of sodium hydrogen sulfate, potassium hydrogen sulfate, and ammonium hydrogen sulfate. ### Claim 26 (depends on 23) The method for producing a glycerin derivative-modified organopolysiloxane elastomer according to claim 23, 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. ### Claim 27 (depends on 23) The method for producing a glycerin derivative-modified organopolysiloxane elastomer according to claim 23, wherein the treatment step using the acidic inorganic salt is performed in the presence of water and/or a hydrophilic medium. ### Claim 28 (depends on 23) The method for producing a glycerin derivative-modified organopolysiloxane elastomer according to claim 23, 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. ### Claim 29 (depends on 23) The method for producing a glycerin derivative-modified organopolysiloxane elastomer according to claim 23, the method further comprising a step of neutralizing by addition of at least one type of basic substance after the treatment step using the acidic inorganic salt.