USRE38116E1 - Method of making siloxane-based polymides - Google Patents

Method of making siloxane-based polymides Download PDF

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USRE38116E1
USRE38116E1 US10/035,497 US3549701A USRE38116E US RE38116 E1 USRE38116 E1 US RE38116E1 US 3549701 A US3549701 A US 3549701A US RE38116 E USRE38116 E US RE38116E
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siloxane
branched
linear
based polyamide
ethyl
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Lenin James Petroff
Jay Brian Rose
Michael Ward Skinner
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Dow Silicones Corp
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Dow Corning Corp
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/42—Polyamides containing atoms other than carbon, hydrogen, oxygen, and nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/452—Block-or graft-polymers containing polysiloxane sequences containing nitrogen-containing sequences
    • C08G77/455—Block-or graft-polymers containing polysiloxane sequences containing nitrogen-containing sequences containing polyamide, polyesteramide or polyimide sequences
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair

Definitions

  • This invention is directed to an improvement in the method of making siloxane-based polyamides described in a prior copending application, U.S. Ser. No. 08/904,709, filed Aug. 1, 1997, and entitled “Cosmetic Composition Containing Siloxane-Based Polyamides as Thickening Agents”, hereafter referred to as the '709 application.
  • the present invention relates to a novel method of making siloxane-based polyamides.
  • the '709 application is directed to one type of a process for preparing siloxane-based polyamides.
  • the process according to the '709 application involves many steps, and this results in cost prohibitive products which are difficult to produce in commercial quantity.
  • a dimethyl hydride endblocked polydimethylsiloxane is first prepared containing the appropriate number of siloxane units to achieve a desired value of DP.
  • the carboxylic acid group of undecylenic acid is then protected through reaction with hexamethyldisilazane.
  • the dimethyl hydride endblocked polydimethylsiloxane and the protected undecylenic acid are reacted to produce a siloxane diacid, i.e., a carboxydecyl terminated polydimethylsiloxane.
  • This reaction is accomplished in the presence of a platinum catalyst, and the product is washed with methanol to remove the trimethylsilyl protecting group from the protected siloxane diacid.
  • the siloxane diacid is then reacted with an organic diamine to produce a siloxane-based polyamide.
  • the new process basically involves the addition of an olefinic acid with an organic diamine to produce an organic diamide.
  • an ⁇ SiH endblocked polysiloxane is added in the presence of a platinum catalyst, to produce a siloxane-based polyamide via hydrosilylation.
  • the resulting polymeric product is in the form of a high molecular weight thermoplastic polymer.
  • This invention relates to a method of forming a siloxane-based polyamides which are useful as thickening agents to formulate a wide variety of cosmetic compositions.
  • the polyamides of this invention are multiples of a unit represented by the following Formula A:
  • the degree of polymerization (DP) is 1-700, preferably 10-500, and more preferably 15-45.
  • DP represents an average value for degree of polymerization of the siloxane units in the polymer with greater or lesser DP values centered around the indicated DP value.
  • n is 1-500, particularly 1-100, and more particularly 4-25.
  • X is a linear or branched chain alkylene having 1-30 carbons, particularly 3-10 carbons, and more particularly 10 carbons.
  • Y is a linear or branched chain alkylene having 1-40 carbons, particularly 1-20 carbons, more particularly 2-6 carbons, and especially 6 carbons wherein
  • the alkylene group may optionally and additionally contain in the alkylene portion at least one of (i) 1-3 amide linkages; (ii) a C5 or C6 cycloalkane; or (iii) phenylene, optionally substituted by 1-3 members which are independently C1-C3 alkyls; and
  • the alkylene group itself may optionally be substituted by at least one of (i) hydroxy; (ii) a C3-C8 cycloalkane; (iii) 1-3 members which are independently C1-C3 alkyls; phenyl, optionally substituted by 1-3 members which are independently C1-C3 alkyls; (iv) a C1-C3 alkyl hydroxy; or (v) a C1-C6 alkyl amine; and
  • Y can be Z where Z is T(R 20 )(R 21 )(R 22 ) where R 20 , R 21 and R 22 are each independently linear or branched C1-C 10 alkylenes; and T is CR in which R is hydrogen, the group defined for R 1 -R 4 , or a trivalent atom such as N, P and Al.
  • R 1 -R 4 is independently methyl, ethyl, propyl, isopropyl, a siloxane chain, or phenyl, wherein the phenyl may optionally be substituted by 1-3 members which are methyl or ethyl. More particularly, R 1 -R 4 are methyl or ethyl, especially methyl.
  • X, Y, DP, and R 1 -R 4 may be the same or different for each polyamide unit.
  • siloxane chain is meant a group of units such as:
  • R 30 and R 31 are each independently organic moieties; and each R 30 and R 31 are connected to silicon by a carbon-silicon bond.
  • the carbon numbers in the alkylene chain do not include the carbons in the extra segments or substitutions.
  • the polyamides must have a siloxane portion in the backbone and optionally may have a siloxane portion in a pendant or branched portion.
  • Formula A is representative of a linear homopolymer.
  • Variations of the invention include: (1) polyamides in which multiple values of DP, and of units X, Y, and R 1 -R 4 occur in one polymeric molecule, and wherein the sequencing of these units may be alternating, random or block; (2) polyamides in which an organic triamine or higher amine such as tris(2-aminoethyl)amine replaces the organic diamine in part, to produce a branched or crosslinked molecule; and (3) physical blends of any of (1) and (2) and/or linear homopolymers.
  • This invention is directed to a new and novel process for making siloxane-based polyamides.
  • the process eliminates costly steps and produces a polymer with higher molecular weights than achieved with the previous process in the '709 application.
  • average molecular weights as measured by gel permeation chromatography (GPC), using the process according to the '709 application were determined to be approximately 50,000.
  • the new process according to the present invention produces average molecular weights of approximately 65,000.
  • the process according to this invention is much faster than the particular process of the '709 application as well as other traditional processes for making siloxane-based polyamides.
  • the '709 application process takes approximately four days to make a finished siloxane-based polyamide polymer, while the new route according to the present invention takes approximately one day.
  • the thermoplastic polymer produced as a result of the instant process is ideal for the thickening of dimethylcyclosiloxanes, which renders it of benefit in a large number of personal care product applications.
  • the new, process involves the addition of an olefinic acid such as undecylenic acid H 2 C ⁇ CH(CH 2 ) 8 COOH to an organic diamine such as hexamethylene diamine H 2 N(CH 2 ) 6 NH 2 , to produce an organic diamide.
  • an organic diamide product is then reacted with an ⁇ SiH endblocked polysiloxane in the presence of a platinum catalyst to produce the siloxane-based polyamide.
  • Analysis using GPC confirm and indicate the achievement of high molecular weight growth using the process according to the present invention.
  • Some examples of compounds of Formula A include:
  • a particular subgroup of Formula I are compounds where R 1 , R 2 , R 3 and R 4 are each methyl.
  • Preferred polyamides of Formula I are:
  • DP is 10-500, particularly 15-45, and more particularly 29.
  • Another particular group contains polyamides of Formula I where X, Y, DP and R 1 -R 4 are the same in each unit of the polymer.
  • X, Y, n, and R 1 -R 4 have the meanings described above for Formula A; m is the same as the value defined for n; and n and m denote the total number of units enclosed within the brackets; with the individual units arranged with regular, alternating, block, or random sequencing.
  • R 5 -R 8 is the same group as defined for R 1 -R 4 ; DP1 and DP2 may be the same or different, and each can be independently the same as defined for DP.
  • the units denominated by n and m may be structured to form either block (regularly sequenced) or random copolymers.
  • a particular subgroup for compounds of Formula II may have methyl for all R groups. Another particular subgroup of compounds of Formula II may have DP1 equal to DP2. A third particular subgroup may have methyl for all R groups, and DP1 equal to DP2.
  • X, Y, m, n, R 1 -R 8 , DP1, DP2 have the same meanings as described above for Formula A and Formula II;
  • Y 1 is independently selected from the same group as defined for Y; and the units denominated by n and m may be structured to form either block (regularly sequenced) or random copolymers.
  • a particular subgroup of compounds of Formula III may have DP1 equal to DP2.
  • Another particular subgroup of compounds of Formula III may have methyl for all R groups.
  • a third particular subgroup may have methyl for all R groups, and DP1 equal to DP2.
  • X, Y, Y 1 , R 1 -R 8 , m, n, DP1, and DP2, are the same as defined above;
  • R 9 -R 12 are the same as defined for R 1 -R 8 ;
  • DP3 is the same as defined for DP;
  • p is the same as defined for m and n;
  • Z is T(R 20 )(R 21 )(R 22 ) where R 20 , R 21 and R 22 are each independently linear or branched C1-C10 alkylenes; and T is CR where R is hydrogen, the same as defined for R 1 -R 4 , or a trivalent atom such as N, P and Al.
  • Preferred values for p are 1-25, with more preferred values being 1-7.
  • Preferred units for R 1 -R 12 are methyl.
  • T is preferably N.
  • Particular values for DP1 to DP3 are 10-500, and more particularly 15-45.
  • R 20 , R 21 , and R 22 are preferably ethylene.
  • a preferred group representative of Z is (—CH 2 CH 2 ) 3 N.
  • X is —(CH 2 ) 10 —
  • Y is —(CH 2 )—
  • DP is 15-45
  • m is 5-20% of n+p
  • Z is (—CH 2 CH 2 ) 3 N.
  • Siloxane-based polyamides according to this invention (1) contain both siloxane groups and amide groups which facilitate the thickening of compositions containing volatile silicone fluids and non-volatile silicone fluids; (2) are non-flowable solids at room temperature; and (3) dissolve in a fluid which contains silicone at a temperature of 25-160° C., to form translucent or clear solutions at a temperature in this range.
  • the siloxane units in the siloxane-based polyamides must be in the main or backbone chain but can also optionally be present in branched or pendent chains.
  • the siloxane units occur in segments as described above.
  • the siloxane units can occur individually or in segments.
  • siloxane-based polyamides include:
  • polyamides of Formula A synthesized with at least a portion of an activated diacid, such as a diacid chloride, dianhydride, or diester, instead of the diacid;
  • a reaction scheme for making polyamides of Formula I according to the '709 application involves the condensation of a siloxane diacid with an organic diamine as shown below.
  • a dimethyl hydride endblocked polydimethylsiloxane such as one of the type shown below, is prepared containing the appropriate number of siloxane units “n” to achieve the desired value of DP.
  • siloxane diacid (product of Step (3)) is reacted with an organic diamine to produce a siloxane-based polyamide.
  • the siloxane diacid is shown below. This reaction may involve the use of a reaction solvent such as toluene or xylene.
  • siloxane-based polyamide which includes at least one repeating unit represented by the formula
  • X is a linear or branched C 1 -C 30 alkylene chain
  • Y is a linear or branched C 1 -C 20 alkylene chain
  • DP is an integer having a value of 10-500
  • n is an integer having a value of 1-500.
  • Suitable olefinic acids which can be used include undecylenic acid H 2 C ⁇ CH(CH 2 ) 8 COOH, acrylic acid H 2 C ⁇ CHCOOH, 3-butenoic acid (vinylacetic acid) H 2 C ⁇ CHCH 2 COOH, 4-pentenoic acid H 2 C ⁇ CHCH 2 COOH, and other olefinic acids with carbon chains of varying length.
  • Organic amines which can be used herein preferably include linear alkyl diamines such as hexamethylene diamine, ethylene diamine, and mixtures of linear alkyl diamines, as well as other amines such as decamethylene diamine.
  • hydrosilylation involves the reaction between a polysiloxane containing ⁇ Si—H groups, and a material containing unsaturation, e.g., vinyl groups.
  • a material containing unsaturation e.g., vinyl groups.
  • the process requires a catalyst to effect the reaction between the ⁇ SiH containing polysiloxane and the material containing unsaturation, i.e., the organic diamide in the case of the present invention.
  • Suitable catalysts are Group VIII transition metals, i.e., the noble metals. Such noble metal catalysts are described in U.S. Pat. No. 3,923,705, incorporated herein by reference to show platinum catalysts.
  • One preferred platinum catalyst is Karstedt's catalyst, which is described in Karstedt's U.S. Pat. Nos. 3,715,334 and 3,814,730, incorporated herein by reference.
  • Karstedt's catalyst is a platinum divinyl tetramethyl disiloxane complex typically containing about one weight percent of platinum in a solvent such as toluene.
  • Another preferred platinum catalyst is a reaction product of chloroplatinic acid and an organosilicon compound containing terminal aliphatic unsaturation. It is described in U.S. Pat. No. 3,419,593, incorporated herein by reference.
  • Most preferred as the catalyst is a neutralized complex of platinous chloride and divinyl tetramethyl disiloxane, for example as described in U.S. Pat. No. 5,175,325.
  • the noble metal catalyst can be used in an amount of from 0.00001-0.5 parts per 100 weight parts of the ⁇ SiH containing polysiloxane. Preferably, the catalyst should be used in an amount sufficient to provide 5-15 parts per million (ppm) Pt metal per total composition.
  • Carrying out of the process is simply a matter of combining the ⁇ SiH containing polysiloxane(s), the material containing unsaturation, i.e., the organic diamide, and the catalyst; and mixing these ingredients.
  • the reaction temperature can vary over a wide range, and the optimum temperature is dependent upon the concentration of the catalyst and the nature of the reactants. Ordinarily, it is best to keep the reaction temperature below about 300° C. Best results with most reactants can be obtained by initiating the reaction at about 80° C. to 180° C., and maintaining the reaction within reasonable limits of this range.
  • the process is carried out using approximately a 1:1 molar ratio of ⁇ Si—H containing polysiloxane and the material containing unsaturation. It is expected that useful materials may also be prepared by carrying out the process with an excess of either the ⁇ Si—H containing polysiloxane or the material containing unsaturation, but this would be considered a less efficient use of the materials.
  • the process can also be used to make other types of siloxane-based polyamides in which the repeating unit of the siloxane-based polyamide is represented by the formula
  • X is a linear or branched C 1 -C 30 alkylene chain
  • Y, Y 1 , and Y 2 are linear or branched C 1 -C 20 alkylene chains
  • DP1, DP2, and DP3 are integers each having values of 10-500
  • n, m, and p are integers each having values of 1-500
  • Z is represented by
  • R′, R′′, and R′′′ are linear or branched C 1 -C 10 alkylene groups; and T is CR in which R is hydrogen, methyl, ethyl, propyl, isopropyl, a siloxane chain, or phenyl, wherein the phenyl may optionally be substituted by 1-3 members which are methyl or ethyl, or T is a trivalent atom such as N, P and Al; provided n is not the same as m, or Y is not the same as Y 1 , or DP1 is not the same as DP2.
  • siloxane-based polyamides Following are specific synthesis examples for forming siloxane-based polyamides according to the method of this invention. Unless otherwise indicated, the vacuums described in Examples 1-4 are in the range of 5-20 millimeters of mercury. While particular siloxane-based polyamides are disclosed or used in the following Examples, it is to be understood that other siloxane-based polyamides, for example, those made with a purified siloxane diacid, dianhydride, diester, or diacid chloride, may also be used.
  • the temperature was increased to 185 degrees C., and 279.2 g of a 30 DP dimethylhydrogen endblocked polydimethylsiloxane was added to the flask over a 30 minute period. After complete addition, a dean stark trap was used to replace the addition funnel on the flask, and the toluene was removed from the flask. After removal of the toluene, the materials were allowed to react for an additional period of one hour. Vacuum stripping was applied to the flask for 1 hour to ensure complete removal of any residual solvent. The temperature of the final siloxane-based polyamide was cooled to 150° C. and poured off while still in the melt form.
  • the temperature controller was increased to 120 degrees C., and 65 g of toluene, and 0.5 g of a solution containing platinum in the form of a complex of platinous chloride and divinyl tetramethyl disiloxane, were added to the flask.
  • the temperature was then increased to 185 degrees C., and 222.0 g of a 20 DP dimethylhydrogen endblocked polydimethylsiloxane was added to the flask over a 30 minute period.
  • a dean stark trap was used to replace the addition funnel on the flask, and the toluene was removed from the flask. After removal of the toluene, the materials were allowed to react for an additional period of one hour. Vacuum stripping was applied to the flask for 1 hour to ensure complete removal of any residual solvent.
  • the temperature of the final siloxane-based polyamide was cooled to 150° C. and poured off while still in the melt form.
  • the temperature was increased to 120 degrees C., and 65 g of toluene, and 0.5 g of a solution containing platinum in the form of a complex of platinous chloride and divinyl tetramethyl disiloxane were added to the flask.
  • the temperature was then increased to 185 degrees C., and 168.72 g of a 15 DP dimethylhydrogen endblocked polydimethylsiloxane was added to the flask over a 30 minute period.
  • a dean stark trap was used to replace the addition funnel on the flask, and the toluene was removed from the flask. After removal of the toluene, the materials were allowed to react for an additional period of one hour. Vacuum stripping was applied to the flask for 1 hour to ensure complete removal of any residual solvent.
  • the temperature of the final siloxane-based polyamide was cooled to 150° C. and poured off while still in the melt form.
  • the temperature was increased to 120 degrees C., and 65 g of toluene, and 0.5 g of a solution containing platinum in the form of a complex of platinous chloride and divinyl tetramethyl disiloxane, were added to the flask.
  • the temperature was then increased to 185 degrees C., and 150.97 g of a 10 DP dimethylhydrogen endblocked polydimethylsiloxane was added to the flask over a 30 minute period.
  • a dean stark trap was used to replace the addition funnel on the flask, and the toluene was removed from the flask. After removal of the toluene, the materials were allowed to react for an additional period of one hour. Vacuum stripping was applied to the flask for 1 hour to ensure complete removal of any residual solvent.
  • the temperature of the final siloxane-based polyamide was cooled to 150° C. and poured off while still in the melt form.
  • undecylenic acid acrylic acid, 3-butenoic acid (vinylacetic acid), and 4-pentenoic acid
  • olefinic acids it should be understood that other branched or straight-chain alkenoic acids C n H 2n-2 )O 2 O 2 can be employed in accordance with the method of the present invention.
  • the siloxane-based polyamides according to this present invention can be used as thickening agents in hair, skin, underarm, and cosmetic, product applications.
  • the siloxane units provide compatibility with silicone fluids such as cyclomethicones, while the amide linkages and the spacing and selection of the locations of the amide linkages, facilitate thickening and formation of such products.

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Abstract

A method of making siloxane-based polyamides which includes at least one repeating unit represented by the formula
Figure USRE038116-20030506-C00001
wherein X is a linear or branched C1-C30 alkylene chain; Y is a linear or branched C1-C20 alkylene chain; DP is an integer having a value of 10-500; n is an integer having a value 1-500. The method involves heating an intimate reaction mixture containing an olefinic acid and an organic diamine at a temperature greater than 100° C. and forming an organic diamide; and thereafter reacting the organic diamide with a hydride-terminated polydimethylsiloxane in the presence of a hydrosilylation catalyst to form the siloxane-based polyamide.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS
Not applicable.
STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT
Not applicable.
REFERENCE TO A MICROFICHE APPENDIX
Not applicable.
FIELD OF THE INVENTION
This invention is directed to an improvement in the method of making siloxane-based polyamides described in a prior copending application, U.S. Ser. No. 08/904,709, filed Aug. 1, 1997, and entitled “Cosmetic Composition Containing Siloxane-Based Polyamides as Thickening Agents”, hereafter referred to as the '709 application.
BACKGROUND OF THE INVENTION
The present invention relates to a novel method of making siloxane-based polyamides.
There is a growing demand in the personal care arena for polymeric materials capable of thickening dimethylcyclosiloxanes in order to modify product viscosity in various market niche hair, skin, cosmetic, and underarm, applications.
The '709 application is directed to one type of a process for preparing siloxane-based polyamides. The process according to the '709 application involves many steps, and this results in cost prohibitive products which are difficult to produce in commercial quantity.
For example, in the '709 application process, a dimethyl hydride endblocked polydimethylsiloxane is first prepared containing the appropriate number of siloxane units to achieve a desired value of DP. The carboxylic acid group of undecylenic acid is then protected through reaction with hexamethyldisilazane. The dimethyl hydride endblocked polydimethylsiloxane and the protected undecylenic acid are reacted to produce a siloxane diacid, i.e., a carboxydecyl terminated polydimethylsiloxane. This reaction is accomplished in the presence of a platinum catalyst, and the product is washed with methanol to remove the trimethylsilyl protecting group from the protected siloxane diacid. The siloxane diacid is then reacted with an organic diamine to produce a siloxane-based polyamide.
Accordingly, a new process has been discovered herein that eliminates many of the otherwise costly steps involved in the process according to the '709 application.
The new process basically involves the addition of an olefinic acid with an organic diamine to produce an organic diamide. One the olefinic acid and the organic diamine are fully reacted, an ≡SiH endblocked polysiloxane is added in the presence of a platinum catalyst, to produce a siloxane-based polyamide via hydrosilylation. The resulting polymeric product is in the form of a high molecular weight thermoplastic polymer. The benefits of this process is that it allows for the production of a cost effective manufactured product in commercial quantity.
BRIEF SUMMARY OF THE INVENTION
This invention relates to a method of forming a siloxane-based polyamides which are useful as thickening agents to formulate a wide variety of cosmetic compositions. The polyamides of this invention are multiples of a unit represented by the following Formula A:
Figure USRE038116-20030506-C00002
where:
(1) The degree of polymerization (DP) is 1-700, preferably 10-500, and more preferably 15-45. DP represents an average value for degree of polymerization of the siloxane units in the polymer with greater or lesser DP values centered around the indicated DP value.
(2) n is 1-500, particularly 1-100, and more particularly 4-25.
(3) X is a linear or branched chain alkylene having 1-30 carbons, particularly 3-10 carbons, and more particularly 10 carbons.
(4) Y is a linear or branched chain alkylene having 1-40 carbons, particularly 1-20 carbons, more particularly 2-6 carbons, and especially 6 carbons wherein
(a) The alkylene group may optionally and additionally contain in the alkylene portion at least one of (i) 1-3 amide linkages; (ii) a C5 or C6 cycloalkane; or (iii) phenylene, optionally substituted by 1-3 members which are independently C1-C3 alkyls; and
(b) the alkylene group itself may optionally be substituted by at least one of (i) hydroxy; (ii) a C3-C8 cycloalkane; (iii) 1-3 members which are independently C1-C3 alkyls; phenyl, optionally substituted by 1-3 members which are independently C1-C3 alkyls; (iv) a C1-C3 alkyl hydroxy; or (v) a C1-C6 alkyl amine; and
(c) Y can be Z where Z is T(R20)(R21)(R22) where R20, R21 and R22 are each independently linear or branched C1-C 10 alkylenes; and T is CR in which R is hydrogen, the group defined for R1-R4, or a trivalent atom such as N, P and Al.
(5) Each of R1-R4 (collectively “R”) is independently methyl, ethyl, propyl, isopropyl, a siloxane chain, or phenyl, wherein the phenyl may optionally be substituted by 1-3 members which are methyl or ethyl. More particularly, R1-R4 are methyl or ethyl, especially methyl.
(6) X, Y, DP, and R1-R4 may be the same or different for each polyamide unit.
By “siloxane chain” is meant a group of units such as:
Figure USRE038116-20030506-C00003
where R30 and R31 are each independently organic moieties; and each R30 and R31 are connected to silicon by a carbon-silicon bond.
The carbon numbers in the alkylene chain do not include the carbons in the extra segments or substitutions. Also, the polyamides must have a siloxane portion in the backbone and optionally may have a siloxane portion in a pendant or branched portion.
If repeated with no variations in the defined variables, Formula A is representative of a linear homopolymer. Variations of the invention include: (1) polyamides in which multiple values of DP, and of units X, Y, and R1-R4 occur in one polymeric molecule, and wherein the sequencing of these units may be alternating, random or block; (2) polyamides in which an organic triamine or higher amine such as tris(2-aminoethyl)amine replaces the organic diamine in part, to produce a branched or crosslinked molecule; and (3) physical blends of any of (1) and (2) and/or linear homopolymers.
These and other features of the invention will become apparent from a consideration of the detailed description.
BRIEF DESCRIPTION OF THE SEVERAL VIEWS OF THE DRAWING
Not applicable.
DETAILED DESCRIPTION OF THE INVENTION
This invention is directed to a new and novel process for making siloxane-based polyamides. As it relates to the '709 application, the process eliminates costly steps and produces a polymer with higher molecular weights than achieved with the previous process in the '709 application. For example, average molecular weights as measured by gel permeation chromatography (GPC), using the process according to the '709 application were determined to be approximately 50,000. The new process according to the present invention produces average molecular weights of approximately 65,000.
In addition, the process according to this invention is much faster than the particular process of the '709 application as well as other traditional processes for making siloxane-based polyamides. The '709 application process takes approximately four days to make a finished siloxane-based polyamide polymer, while the new route according to the present invention takes approximately one day. The thermoplastic polymer produced as a result of the instant process is ideal for the thickening of dimethylcyclosiloxanes, which renders it of benefit in a large number of personal care product applications.
Basically the new, process involves the addition of an olefinic acid such as undecylenic acid H2C═CH(CH2)8COOH to an organic diamine such as hexamethylene diamine H2N(CH2)6NH2, to produce an organic diamide. This organic diamide product is then reacted with an ≡SiH endblocked polysiloxane in the presence of a platinum catalyst to produce the siloxane-based polyamide. Analysis using GPC confirm and indicate the achievement of high molecular weight growth using the process according to the present invention.
Some examples of compounds of Formula A include:
1) Polyamides of Formula I:
Figure USRE038116-20030506-C00004
 where X, Y, n, R1-R4, and DP are as defined for Formula A, A particular subgroup of Formula I are compounds where R1, R2, R3 and R4 are each methyl.
Preferred polyamides of Formula I are:
Figure USRE038116-20030506-C00005
where DP is 10-500, particularly 15-45, and more particularly 29. Another particular group contains polyamides of Formula I where X, Y, DP and R1-R4 are the same in each unit of the polymer.
2) Polyamides containing multiple siloxane block lengths as shown in Formula II:
Figure USRE038116-20030506-C00006
 where X, Y, n, and R1-R4 have the meanings described above for Formula A; m is the same as the value defined for n; and n and m denote the total number of units enclosed within the brackets; with the individual units arranged with regular, alternating, block, or random sequencing.
R5-R8 is the same group as defined for R1-R4; DP1 and DP2 may be the same or different, and each can be independently the same as defined for DP. The units denominated by n and m may be structured to form either block (regularly sequenced) or random copolymers.
A particular subgroup for compounds of Formula II may have methyl for all R groups. Another particular subgroup of compounds of Formula II may have DP1 equal to DP2. A third particular subgroup may have methyl for all R groups, and DP1 equal to DP2.
3) Polyamides synthesized from multiple diamines as shown in Formula III:
Figure USRE038116-20030506-C00007
 where X, Y, m, n, R1-R8, DP1, DP2 have the same meanings as described above for Formula A and Formula II; Y1 is independently selected from the same group as defined for Y; and the units denominated by n and m may be structured to form either block (regularly sequenced) or random copolymers.
A particular subgroup of compounds of Formula III may have DP1 equal to DP2. Another particular subgroup of compounds of Formula III may have methyl for all R groups. A third particular subgroup may have methyl for all R groups, and DP1 equal to DP2.
4) Polyamides synthesized with a trifunctional amine as shown in Formula IV:
Figure USRE038116-20030506-C00008
 where X, Y, Y1, R1-R8, m, n, DP1, and DP2, are the same as defined above; R9-R12 are the same as defined for R1-R8; DP3 is the same as defined for DP; p is the same as defined for m and n; Z is T(R20)(R21)(R22) where R20, R21 and R22 are each independently linear or branched C1-C10 alkylenes; and T is CR where R is hydrogen, the same as defined for R1-R4, or a trivalent atom such as N, P and Al.
Preferred values for p are 1-25, with more preferred values being 1-7. Preferred units for R1-R12 are methyl. T is preferably N. Particular values for DP1 to DP3 are 10-500, and more particularly 15-45. R20, R21, and R22 are preferably ethylene. A preferred group representative of Z is (—CH2CH2)3N.
One particular group of compounds of Formula IV is represented by the formula
Figure USRE038116-20030506-C00009
where X is —(CH2)10—, Y is —(CH2)—; DP is 15-45; m is 5-20% of n+p; and Z is (—CH2CH2)3N.
Siloxane-based polyamides according to this invention (1) contain both siloxane groups and amide groups which facilitate the thickening of compositions containing volatile silicone fluids and non-volatile silicone fluids; (2) are non-flowable solids at room temperature; and (3) dissolve in a fluid which contains silicone at a temperature of 25-160° C., to form translucent or clear solutions at a temperature in this range.
With regard to the siloxane units in the siloxane-based polyamides, the siloxane units must be in the main or backbone chain but can also optionally be present in branched or pendent chains. In the main chain the siloxane units occur in segments as described above. In the branched or pendent chains the siloxane units can occur individually or in segments.
Particular groups of siloxane-based polyamides include:
(a) polyamides of Formula I where the DP is 15-50;
(b) physical blends of two or more polyamides wherein at least one polyamide has a value for DP in the range of 15-50, and at least one polyamide has a value for DP in the range of 30-500;
(c) compounds of Formula II where (1) the value for DP1 is 15-50, and the value for DP2 is 30-500; and (2) the portion of the polyamide having DP1 is about 1-99 weight % based on the weight of the total polyamide content, and the portion of the polyamide having DP2 is about 1-99 weight %;
(d) physical blends of polyamides of Formula I made by combining (1) 80-99 weight % of a polyamide where n is 2-10, and especially where n is 3-6; and (2) 1-20 weight % of a polyamide where n is 5-500, especially where n is 6-100;
(e) polyamides of Formula III where at least one Y or Y1 contains at least one hydroxyl substitution;
(f) polyamides of Formula A synthesized with at least a portion of an activated diacid, such as a diacid chloride, dianhydride, or diester, instead of the diacid;
(g) polyamides of Formula A where X is —(CH2)3—; and
(h) polyamides of Formula A where X is —(CH2)10—.
THE PROCESS ACCORDING TO THE '709 APPLICATION
A reaction scheme for making polyamides of Formula I according to the '709 application involves the condensation of a siloxane diacid with an organic diamine as shown below.
(1) A dimethyl hydride endblocked polydimethylsiloxane, such as one of the type shown below, is prepared containing the appropriate number of siloxane units “n” to achieve the desired value of DP.
Figure USRE038116-20030506-C00010
(2) The carboxylic acid group of undecylenic acid is protected through reaction with hexamethyldisilazane (CH3)3—Si—NH—Si—(CH3)3. This step is shown below.
Figure USRE038116-20030506-C00011
(3) The dimethyl hydride endblocked polydimethylsiloxane and the protected undecylenic acid (the products of Steps (1) and (2)) are reacted to produce a siloxane diacid )carboxydecyl terminated polydimethylsiloxane). This reaction is accomplished in the presence of a platinum catalyst such as chloroplatinic acid, and the product is washed with methanol to remove the trimethylsilyl protecting group from the protected siloxane diacid shown below.
Figure USRE038116-20030506-C00012
where Q is
Figure USRE038116-20030506-C00013
(4) The siloxane diacid (product of Step (3)) is reacted with an organic diamine to produce a siloxane-based polyamide. The siloxane diacid is shown below. This reaction may involve the use of a reaction solvent such as toluene or xylene.
Figure USRE038116-20030506-C00014
Figure USRE038116-20030506-C00015
THE PROCESS ACCORDING TO THE PRESENT INVENTION
The simplified process of the present invention can be illustrated schematically with reference to the following reaction scenario in which an olefinic acid is reacted with an organic diamine to produce an organic diamide.
Figure USRE038116-20030506-C00016
The organic diamide is then in turn reacted with a hydride-terminated polydimethylsiloxane of the structure such as the one depicted below:
Figure USRE038116-20030506-C00017
in the presence of a hydrosilylation catalyst to form a siloxane-based polyamide which includes at least one repeating unit represented by the formula
Figure USRE038116-20030506-C00018
wherein X is a linear or branched C1-C30 alkylene chain; Y is a linear or branched C1-C20 alkylene chain; DP is an integer having a value of 10-500; n is an integer having a value of 1-500.
Suitable olefinic acids which can be used include undecylenic acid H2C═CH(CH2)8COOH, acrylic acid H2C═CHCOOH, 3-butenoic acid (vinylacetic acid) H2C═CHCH2COOH, 4-pentenoic acid H2C═CHCH2COOH, and other olefinic acids with carbon chains of varying length.
Organic amines which can be used herein preferably include linear alkyl diamines such as hexamethylene diamine, ethylene diamine, and mixtures of linear alkyl diamines, as well as other amines such as decamethylene diamine.
A platinum catalyzed hydrosilylation reaction is employed according to this invention. Generally, hydrosilylation involves the reaction between a polysiloxane containing ≡Si—H groups, and a material containing unsaturation, e.g., vinyl groups. Some attractive features of this mechanism are that no by-products are formed, and hydrosilylation will proceed even at room temperature. In the mechanism, crosslinking involves addition of ≡SiH across double bonds, i.e.,
≡SiH+CH2═R→≡SiCH2CH2—R.
The process requires a catalyst to effect the reaction between the ≡SiH containing polysiloxane and the material containing unsaturation, i.e., the organic diamide in the case of the present invention. Suitable catalysts are Group VIII transition metals, i.e., the noble metals. Such noble metal catalysts are described in U.S. Pat. No. 3,923,705, incorporated herein by reference to show platinum catalysts. One preferred platinum catalyst is Karstedt's catalyst, which is described in Karstedt's U.S. Pat. Nos. 3,715,334 and 3,814,730, incorporated herein by reference. Karstedt's catalyst is a platinum divinyl tetramethyl disiloxane complex typically containing about one weight percent of platinum in a solvent such as toluene. Another preferred platinum catalyst is a reaction product of chloroplatinic acid and an organosilicon compound containing terminal aliphatic unsaturation. It is described in U.S. Pat. No. 3,419,593, incorporated herein by reference. Most preferred as the catalyst is a neutralized complex of platinous chloride and divinyl tetramethyl disiloxane, for example as described in U.S. Pat. No. 5,175,325.
The noble metal catalyst can be used in an amount of from 0.00001-0.5 parts per 100 weight parts of the ≡SiH containing polysiloxane. Preferably, the catalyst should be used in an amount sufficient to provide 5-15 parts per million (ppm) Pt metal per total composition.
Carrying out of the process is simply a matter of combining the ≡SiH containing polysiloxane(s), the material containing unsaturation, i.e., the organic diamide, and the catalyst; and mixing these ingredients. The reaction temperature can vary over a wide range, and the optimum temperature is dependent upon the concentration of the catalyst and the nature of the reactants. Ordinarily, it is best to keep the reaction temperature below about 300° C. Best results with most reactants can be obtained by initiating the reaction at about 80° C. to 180° C., and maintaining the reaction within reasonable limits of this range.
Typically, the process is carried out using approximately a 1:1 molar ratio of ≡Si—H containing polysiloxane and the material containing unsaturation. It is expected that useful materials may also be prepared by carrying out the process with an excess of either the ≡Si—H containing polysiloxane or the material containing unsaturation, but this would be considered a less efficient use of the materials.
The process can also be used to make other types of siloxane-based polyamides in which the repeating unit of the siloxane-based polyamide is represented by the formula
Figure USRE038116-20030506-C00019
or by the formula
Figure USRE038116-20030506-C00020
wherein X is a linear or branched C1-C30 alkylene chain; Y, Y1, and Y2 are linear or branched C1-C20 alkylene chains; DP1, DP2, and DP3 are integers each having values of 10-500; n, m, and p are integers each having values of 1-500; Z is represented by
Figure USRE038116-20030506-C00021
wherein R′, R″, and R″′ are linear or branched C1-C10 alkylene groups; and T is CR in which R is hydrogen, methyl, ethyl, propyl, isopropyl, a siloxane chain, or phenyl, wherein the phenyl may optionally be substituted by 1-3 members which are methyl or ethyl, or T is a trivalent atom such as N, P and Al; provided n is not the same as m, or Y is not the same as Y1, or DP1 is not the same as DP2.
EXAMPLES
Following are specific synthesis examples for forming siloxane-based polyamides according to the method of this invention. Unless otherwise indicated, the vacuums described in Examples 1-4 are in the range of 5-20 millimeters of mercury. While particular siloxane-based polyamides are disclosed or used in the following Examples, it is to be understood that other siloxane-based polyamides, for example, those made with a purified siloxane diacid, dianhydride, diester, or diacid chloride, may also be used.
Example 1
30 DP Polymer
A 500 ml three neck flask equipped with a thermometer, electrical stirrer, nitrogen sweep, and a condenser, was charged with 50.12 g of undecylenic acid, and 22.58 g of a 70% hexamethylene diamine mixture in water. The flask was immediately heated to 225 degrees C. and kept at this temperature for 2 hours. After 2 hours, a vacuum was applied to the system for 2 hours to remove any unreacted materials. Upon completion of vacuum stripping, the flask was reweighed to obtain the product weight. The temperature was increased to 120 degrees C., and 65 g of toluene, complex of platinous chloride and divinyl tetramethyl disiloxane, were added to the flask. The temperature was increased to 185 degrees C., and 279.2 g of a 30 DP dimethylhydrogen endblocked polydimethylsiloxane was added to the flask over a 30 minute period. After complete addition, a dean stark trap was used to replace the addition funnel on the flask, and the toluene was removed from the flask. After removal of the toluene, the materials were allowed to react for an additional period of one hour. Vacuum stripping was applied to the flask for 1 hour to ensure complete removal of any residual solvent. The temperature of the final siloxane-based polyamide was cooled to 150° C. and poured off while still in the melt form.
Example 2
20 DP Polymer
A 500 ml three neck flask equipped with a thermometer, electrical stirrer, nitrogen sweep, and a condenser, was charged with 55.0 g of undecylenic acid, and 24.77 g of a 70% hexamethylene diamine mixture in water. The flask was immediately heated to 225 degrees C., and kept at this temperature for 2 hours. After 2 hours, a vacuum was applied to the system for 2 hour to remove any unreacted materials. Upon completion of vacuum stripping, the flask was reweighed to obtain the product weight. The temperature controller was increased to 120 degrees C., and 65 g of toluene, and 0.5 g of a solution containing platinum in the form of a complex of platinous chloride and divinyl tetramethyl disiloxane, were added to the flask. The temperature was then increased to 185 degrees C., and 222.0 g of a 20 DP dimethylhydrogen endblocked polydimethylsiloxane was added to the flask over a 30 minute period. After complete addition, a dean stark trap was used to replace the addition funnel on the flask, and the toluene was removed from the flask. After removal of the toluene, the materials were allowed to react for an additional period of one hour. Vacuum stripping was applied to the flask for 1 hour to ensure complete removal of any residual solvent. The temperature of the final siloxane-based polyamide was cooled to 150° C. and poured off while still in the melt form.
Example 3
15 DP Polymer
A 500 ml three neck flask equipped with a thermometer, electrical stirrer, nitrogen sweep, and a condenser, was charged with 57.75 g of undecylenic acid, and 24.77 g of a 70% hexamethylene diamine mixture in water. The flask was immediately heated to 225 degrees C., and kept at this temperature for 2 hours. After 2 hours, a vacuum was applied to the system for 2 hours to remove any unreacted materials. Upon completion of vacuum stripping, the flask was reweighed to obtain the product weight. The temperature was increased to 120 degrees C., and 65 g of toluene, and 0.5 g of a solution containing platinum in the form of a complex of platinous chloride and divinyl tetramethyl disiloxane were added to the flask. The temperature was then increased to 185 degrees C., and 168.72 g of a 15 DP dimethylhydrogen endblocked polydimethylsiloxane was added to the flask over a 30 minute period. After complete addition, a dean stark trap was used to replace the addition funnel on the flask, and the toluene was removed from the flask. After removal of the toluene, the materials were allowed to react for an additional period of one hour. Vacuum stripping was applied to the flask for 1 hour to ensure complete removal of any residual solvent. The temperature of the final siloxane-based polyamide was cooled to 150° C. and poured off while still in the melt form.
Example 4
10 DP Polymer
A 500 ml three neck flask equipped with a thermometer, electrical stirrer, nitrogen sweep, and a condenser, was charged with 67.0 g of undecylenic acid, and 29.82 g of a 70% hexamethylene diamine mixture in water. The flask was immediately heated to 225 degrees C., and kept at this temperature for 2 hours. After 2 hours, a vacuum was applied to the system for 2 hours to remove any unreacted materials. Upon completion of vacuum stripping, the flask was reweighed to obtain the product weight. The temperature was increased to 120 degrees C., and 65 g of toluene, and 0.5 g of a solution containing platinum in the form of a complex of platinous chloride and divinyl tetramethyl disiloxane, were added to the flask. The temperature was then increased to 185 degrees C., and 150.97 g of a 10 DP dimethylhydrogen endblocked polydimethylsiloxane was added to the flask over a 30 minute period. After complete addition, a dean stark trap was used to replace the addition funnel on the flask, and the toluene was removed from the flask. After removal of the toluene, the materials were allowed to react for an additional period of one hour. Vacuum stripping was applied to the flask for 1 hour to ensure complete removal of any residual solvent. The temperature of the final siloxane-based polyamide was cooled to 150° C. and poured off while still in the melt form.
Although undecylenic acid, acrylic acid, 3-butenoic acid (vinylacetic acid), and 4-pentenoic acid, have been set forth as being representative examples of some suitable olefinic acids, it should be understood that other branched or straight-chain alkenoic acids CnH2n-2)O2O2 can be employed in accordance with the method of the present invention.
The siloxane-based polyamides according to this present invention can be used as thickening agents in hair, skin, underarm, and cosmetic, product applications. The siloxane units provide compatibility with silicone fluids such as cyclomethicones, while the amide linkages and the spacing and selection of the locations of the amide linkages, facilitate thickening and formation of such products.
Other variations may be made in compounds, compositions, and methods described herein without departing from the essential features of the invention. The embodiments of the invention specifically illustrated herein are exemplary only and not intended as limitations on their scope except as defined in the appended claims.

Claims (20)

I claim:
1. A method of making a siloxane-based polyamide which includes at least one repeating unit represented by the formula
Figure USRE038116-20030506-C00022
wherein X is a linear or branched C3 to C10 alkylene chain; Y is a linear or branched C1-C20 alkylene chain; R1-R4 are independently methyl, ethyl, propyl, isopropyl, a siloxane chain, phenyl, or phenyl substituted by 1-3 members which are methyl or ethyl; DP is an integer having a value of 10-500; and n is an integer having a value of 1-500;
the method comprising heating a reaction mixture containing an olefinic acid and an organic diamine at a temperature greater than 100° C. and forming an organic diamide; and thereafter reacting the organic diamide with a hydride-terminated polydimethylsiloxane in the presence of a hydrosilylation catalyst to form the siloxane-based polyamide.
2. A method according to claim 1 in which the organic diamine is a compound selected from the group consisting of hexamethylene diamine, ethylene diamine, and decamethylene diamine.
3. A method according to claim 1 in which the olefinic acid is a compound selected from the group consisting of undecylenic acid, acrylic acid, 3-butenoic acid, and 4-pentenoic acid.
4. A method according to claim 1 in which the siloxane-based polyamide has a number average molecular weight of from 4,000 to 200,000 daltons, as determined by gel permeation chromatography using polydimethylsiloxane as a standard.
5. A method according to claim 4 in which the siloxane-based polyamide has a number average molecular weight of from 5,000 to 65,000 daltons, as determined by gel permeation chromatography using polydimethylsiloxane as a standard.
6. A method according to claim 1 in which the repeating unit of the siloxane-based polyamide is represented by the formula
Figure USRE038116-20030506-C00023
wherein X is a linear or branched C3 to C10 alkylene chain; Y, Y1, and Y2 are linear or branched C1-C20 alkylene chains; DP1, DP2, and DP3 are integers each having values of 10-500; n, m, and p are integers each having values of 1-500; Z is represented by
Figure USRE038116-20030506-C00024
wherein R′, R″, and R″′ are linear or branched C1-C10 alkylene groups; and T is CR in which R is hydrogen, methyl, ethyl, propyl, isopropyl, a siloxane chain, or phenyl, wherein the phenyl may optionally be substituted by 1-3 members which are methyl or ethyl, or T is a trivalent atom such as N, P and Al; provided n is not the same as m, or Y is not the same as Y1, or DP1 is not the same as DP2.
7. A method of making a siloxane-based polyamide which includes at least one repeating unit represented by the formula
Figure USRE038116-20030506-C00025
wherein X is a linear or branched C3 to C10 alkylene chain; Y is a linear or branched C1-C20 alkylene chain; R1-R4 are independently methyl, ethyl, propyl, isopropyl, a siloxane chain, phenyl, or phenyl substituted by 1-3 members which are methyl or ethyl; DP is an integer having a value of 10-500; and n is an integer having a value of 1-500;
the method comprising reacting an organic diamide with a hydride-terminated polydimethylsiloxane in the presence of a hydrosilylation catalyst to form the siloxane-based polyamide.
8. A method according to claim 7 in which the siloxane-based polyamide has a number average molecular weight of from 4,000 to 200,000 daltons, as determined by gel permeation chromatography using polydimethylsiloxane as a standard.
9. A method according to claim 8 in which the siloxane-based polyamide has a number average molecular weight of from 5,000 to 65,000 daltons, as determined by gel permeation chromatography using polydimethylsiloxane as a standard.
10. A method according to claim 7 in which the repeating unit of the siloxane-based polyamide is represented by the formula
Figure USRE038116-20030506-C00026
Figure USRE038116-20030506-C00027
wherein X is a linear or branched C3 to C10 alkylene chain; Y, Y1, and Y2 are linear or branched C1-C20 alkylene chains; DP1, DP2, and DP3 are integers each having values of 10-500; n, m, and p are integers each having values of 1-500; Z is represented by
Figure USRE038116-20030506-C00028
wherein R′, R″, and R′″ are linear or branched C1-C10 alkylene groups; and T is CR in which R is hydrogen, methyl, ethyl, propyl, isopropyl, a siloxane chain, or phenyl, wherein the phenyl may optionally be substituted by 1-3 members which are methyl or ethyl, or T is a trivalent atom such as N, P and Al; provided n is not the same as m, or Y is not the same as Y1, or DP1 is not the same as DP2.
11. A method of making a siloxane-based polyamide which includes at least one repeating unit represented by the formula
Figure USRE038116-20030506-C00029
wherein X is a linear or branched C 3 -C 10 alkylene chain; Y is a linear or branched C 1 -C 20 alkylene chain; R 1 -R 4 are independently methyl, ethyl, propyl, isopropyl, a siloxane chain, phenyl, or phenyl substituted by 1-3 members which are methyl or ethyl; DP is an integer having a value of 10-500; and n is an integer having a value of 1-500;
the method comprising heating a reaction mixture containing an olefinic acid and an organic diamine at a temperature greater than 100° C. and forming an organic diamide; and thereafter reacting the organic diamide with an ≡SiH containing polysiloxane in the presence of a hydrosilylation catalyst to form the siloxane-based polyamide.
12. A method according to claim 11 in which the organic diamine is a compound selected from the group consisting of hexamethylene diamine, ethylene diamine, and decamethylene diamine.
13. A method according to claim 11 in which the olefinic acid is a compound selected from the group consisting of undecylenic acid, acrylic acid, 3-butenoic acid, and 4 -pentenoic acid.
14. A method according to claim 11 in which the siloxane-based polyamide has a number average molecular weight of from 4,000 to 200,000 daltons, as determined by gel permeation chromatography using polydimethylsiloxane as a standard.
15. A method according to claim 14 in which the siloxane-based polyamide has a number average molecular weight of from 5,000 to 65,000 daltons, as determined by gel permeation chromatography using polydimethylsiloxane as a standard.
16. A method according to claim 11 in which the repeating unit of the siloxane-based polyamide is represented by the formula
Figure USRE038116-20030506-C00030
or the formula
Figure USRE038116-20030506-C00031
wherein X is a linear or branched C 3 -C 10 alkylene chain; Y, Y 1 , and Y 2 are linear or branched C 1 -C 20 alkylene chains; DP1, DP2, and DP3 are integers each having values of 10-500; n, m, and p are integers each having values of 1-500; Z is represented by
Figure USRE038116-20030506-C00032
wherein R′, R″, and R′″ are linear or branched C 1 -C 10 alkylene groups; and T is CR in which R is hydrogen, methyl, ethyl, propyl, isopropyl, a siloxane chain, or phenyl, wherein the phenyl may optionally be substituted by 1-3 members which are methyl or ethyl, or T is a trivalent atom such as N, P and Al; provided n is not the same as m, or Y is not the same as Y 1 , or DP1 is not the same as DP2.
17. A method of making a siloxane-based polyamide which includes at least one repeating unit represented by the formula
Figure USRE038116-20030506-C00033
wherein X is a linear or branched C 3 -C 10 alkylene chain; Y is a linear or branched C 1 -C 20 alkylene chain; R 1 -R 4 are independently methyl, ethyl, propyl, isopropyl, a siloxane chain, phenyl, or phenyl substituted by 1-3 members which are methyl or ethyl; DP is an integer having a value of 10-500; and n is an integer having a value of 1-500;
the method comprising reacting an organic diamide with an ≡SiH containing polysiloxane in the presence of a hydrosilylation catalyst to form the siloxane-based polyamide.
18. A method according to claim 17 in which the siloxane-based polyamide has a number average molecular weight of from 4,000 to 200,000 daltons, as determined by gel permeation chromatography using polydimethylsiloxane as a standard.
19. A method according to claim 18 in which the siloxane-based polyamide has a number average molecular weight of from 5,000 to 65,000 daltons, as determined by gel permeation chromatography using polydimethylsiloxane as a standard.
20. A method according to claim 17 in which the repeating time of the siloxane-based polyamide is represented by the formula
Figure USRE038116-20030506-C00034
or the formula
Figure USRE038116-20030506-C00035
wherein X is a linear or branched C 3 -C 10 alkylene chain; Y, Y 1 , and Y 2 are linear or branched C 1 -C 20 alkylene chains; DP1, DP2, and DP3 are integers each having values of 10-500; n, m, and p are integers each having values of 1-500; Z is represented by
Figure USRE038116-20030506-C00036
wherein R′, R″, and R′″ are linear or branched C 1 -C 10 alkylene groups; and T is CR in which R is hydrogen, methyl, ethyl, propyl, isopropyl, a siloxane chain, or phenyl, wherein the phenyl may optionally be substituted by 1-3 members which are methyl or ethyl, or T is a trivalent atom such as N, P and Al; provided n is not the same as m, or Y is not the same as Y 1 , or DP1 is not the same as DP2.
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Cited By (5)

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Families Citing this family (413)

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US6835399B2 (en) 2000-12-12 2004-12-28 L'ORéAL S.A. Cosmetic composition comprising a polymer blend
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US8333956B2 (en) 2002-06-11 2012-12-18 Color Access, Inc. Stable cosmetic emulsion with polyamide gelling agent
US20040120912A1 (en) * 2002-12-17 2004-06-24 L'oreal Compositions containing at least one oil structured with at least one silicone-polyamide polymer, and at least one crystalline silicone compound and methods of using the same
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US20050008598A1 (en) 2003-07-11 2005-01-13 Shaoxiang Lu Cosmetic compositions comprising a structuring agent, silicone powder and swelling agent
US6743868B2 (en) * 2002-07-18 2004-06-01 Dow Corning Corporation Polyamide based thermoplastic silicone elastomers
US7008629B2 (en) 2002-07-22 2006-03-07 L'ORéAL S.A. Compositions comprising at least one heteropolymer and fibers, and methods of using the same
US8007772B2 (en) 2002-10-02 2011-08-30 L'oreal S.A. Compositions to be applied to the skin and the integuments
US6783692B2 (en) 2002-10-17 2004-08-31 Dow Corning Corporation Heat softening thermally conductive compositions and methods for their preparation
MXPA05004283A (en) * 2002-10-24 2005-08-03 Colgate Palmolive Co Silicon modified polyamide material useful for oral care.
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US20060193801A1 (en) * 2005-01-31 2006-08-31 L'oreal Solid cosmetic composition textured with an organic copolymer
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US20060216257A1 (en) * 2005-03-24 2006-09-28 L'oreal Makeup and/or care kit providing volumizing effect
EP1866397A2 (en) * 2005-03-29 2007-12-19 Arizona Chemical Company Compostions containing fatty acids and/or derivatives thereof and a low temperature stabilizer
US8153724B2 (en) * 2005-04-06 2012-04-10 Dow Corning Corporation Organosiloxane compositions
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WO2006134896A1 (en) * 2005-06-14 2006-12-21 Kokyu Alcohol Kogyo Co., Ltd. Transparent oily solid cosmetic
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US7790148B2 (en) * 2005-09-02 2010-09-07 L'oreal Compositions containing silicone polymer, wax and volatile solvent
US7884158B2 (en) * 2005-09-06 2011-02-08 L'Oré´al Cosmetic compositions containing block copolymers, tackifiers and phenylated silicones
US20070093619A1 (en) * 2005-10-24 2007-04-26 L'oreal Compositions having enhanced cosmetic properties
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US7501184B2 (en) 2005-12-23 2009-03-10 3M Innovative Properties Company Polydiorganosiloxane polyoxamide copolymers
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KR101387294B1 (en) 2006-03-21 2014-04-18 다우 코닝 코포레이션 Silicone polyether elastomer gels
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US8088399B2 (en) * 2007-01-12 2012-01-03 L'oreal Use of active principles which are capable of enhancing the content of ceramides, as protective agent for delicate lips
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US20080171008A1 (en) * 2007-01-17 2008-07-17 L'oreal S.A. Composition containing a polyorganosiloxane polymer, a tackifier, a wax and a block copolymer
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US20080318065A1 (en) 2007-06-22 2008-12-25 Sherman Audrey A Mixtures of polydiorganosiloxane polyamide-containing components and organic polymers
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WO2010047993A2 (en) 2008-10-22 2010-04-29 Dow Corning Corporation Aminofunctional endblocked silicone polyether copolymers in personal care compositions
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KR20120101015A (en) 2009-10-23 2012-09-12 다우 코닝 코포레이션 Hydrophilically-modified silicone compositions
US8784787B2 (en) 2009-10-23 2014-07-22 Dow Corning Toray Co., Ltd. Co-modified organopolysiloxane
US9243113B2 (en) 2009-10-23 2016-01-26 Dow Corning Corporation Silicone compositions comprising a swollen silicone gel
CN102648264B (en) 2009-10-23 2015-08-19 道康宁东丽株式会社 Thickeners or gelling agents for oil-based materials
CN102666663A (en) 2009-10-23 2012-09-12 道康宁东丽株式会社 Novel organopolysiloxane copolymer
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JP5577081B2 (en) 2009-12-03 2014-08-20 東レ・ダウコーニング株式会社 New organopolysiloxane and cosmetics
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FR2954140A1 (en) 2009-12-17 2011-06-24 Oreal COSMETIC OR DERMATOLOGICAL COMPOSITIONS BASED ON BACTERIOCINS AND PREBIOTICS
EP2335677A1 (en) 2009-12-17 2011-06-22 L'Oréal Cosmetic composition with a volume-increasing effect including behenyl alcohol used as a thickener
FR2954138B1 (en) 2009-12-17 2012-03-02 Oreal COSMETIC TREATMENT PROCESS FOR BODY ODORS USING BACTERIOCIN COMPOSITION
FR2954131B1 (en) 2009-12-18 2016-02-19 Oreal COSMETIC COMPOSITION COMPRISING A SUPRAMOLECULAR COMPOUND CAPABLE OF ESTABLISHING HYDROGEN BONDS, AND A PARTICULAR OIL
EP2353582A1 (en) 2009-12-18 2011-08-10 L'Oréal Cosmetic composition for eyelashes
FR2954130B1 (en) 2009-12-18 2012-02-24 Oreal COSMETIC COMPOSITION COMPRISING A SUPRAMOLECULAR COMPOUND CAPABLE OF ESTABLISHING HYDROGEN BONDS, AND A PARTICULAR ADDITIONAL INGREDIENT
JP5841311B2 (en) 2009-12-21 2016-01-13 東レ・ダウコーニング株式会社 Oily raw material thickener or gelling agent, gel composition containing the same, and method for producing cosmetic or external preparation
CN102665668B (en) 2009-12-24 2014-10-22 道康宁东丽株式会社 Copolymer having carbosiloxane dendrimer structure, and composition and cosmetic containing the same
US9260607B2 (en) 2009-12-24 2016-02-16 Dow Corning Toray Co., Ltd. Surface-treatment agent for powder for use in cosmetic and cosmetic containing powder treated with the same
WO2011090644A2 (en) * 2009-12-30 2011-07-28 3M Innovative Properties Company Moisture-curable siloxanes and siloxane polymers
US20110202029A1 (en) * 2010-02-16 2011-08-18 The Procter & Gamble Company Release sheet material
US20110202028A1 (en) 2010-02-16 2011-08-18 Carlo Toro Release sheet material
FR2958158B1 (en) 2010-03-30 2012-06-08 Oreal COSMETIC COMPOSITION BASED ON POLYESTER
JP5827790B2 (en) 2010-04-28 2015-12-02 東レ・ダウコーニング株式会社 Cosmetic and skin external preparation containing higher alcohol-modified silicone
CN102906161B (en) 2010-04-30 2014-10-22 道康宁东丽株式会社 Novel organopolysiloxane, surfactant, emulsion composition, powder treatment agent, thickening agent of oil-based raw material, gelling agent, gel composition, and cosmetic raw material comprising novel organopolysiloxane, as well as, preparation for external use and cosmetic comprising the same
CN102946852B (en) 2010-04-30 2016-03-16 道康宁东丽株式会社 Comprise the powder-processed agent of the organopolysiloxane of sugar alcohol modification
CN102947369B (en) 2010-04-30 2015-01-28 道康宁东丽株式会社 Organopolysiloxane and use thereof as surfactant, powder treatment agent, thickening agent of oil-based raw material or gelling agent. gel and emulsion compositions, as well as, preparations for external use and cosmetics comprising the same
FR2959932A1 (en) 2010-05-17 2011-11-18 Oreal MAKE-UP AND / OR CARE COMPOSITION OF KERATIN FIBERS HAVING IMPROVED HOLDING PROPERTIES
WO2011148325A1 (en) 2010-05-26 2011-12-01 L'oreal Cosmetic composition based on a supramolecular polymer and a silicone filler
FR2960434B1 (en) 2010-05-26 2012-08-17 Oreal COSMETIC COMPOSITION BASED ON A SUPRAMOLECULAR POLYMER AND AN ABSORBENT CHARGE
FR2960433B1 (en) 2010-05-26 2012-08-17 Oreal COSMETIC METHOD FOR MAKE-UP AND / OR CARE OF SKIN AND / OR LIP
WO2011148324A2 (en) 2010-05-26 2011-12-01 L'oreal Cosmetic composition based on a supramolecular polymer and a silicone compound
FR2961093A1 (en) 2010-06-09 2011-12-16 Oreal COSMETIC COMPOSITION COMPRISING A POLYMER AND A 4-CARBOXY 2-PYRROLIDINONE DERIVATIVE, COSMETIC TREATMENT METHOD AND COMPOUND
US8933134B2 (en) 2010-06-09 2015-01-13 L'oreal Compositions containing agar and a softening agent
FR2961396B1 (en) 2010-06-16 2013-03-15 Oreal PROCESS FOR MAKE-UP OR CARE OF KERATIN FIBERS USING RETRACTABLE FIBERS AND USE THEREOF
FR2961508A1 (en) 2010-06-17 2011-12-23 Oreal AMINO ACID DERIVATIVES; COMPOSITIONS CONTAINING THEM; USE AS A TREATMENT AGENT FOR HUMAN PERSPIRATION
FR2961510A1 (en) 2010-06-17 2011-12-23 Oreal USE AS A TREATMENT AGENT FOR HUMAN PERSPIRATION; NOVEL AMINO ACID DERIVATIVES; COMPOSITIONS CONTAINING THEM
FR2961509B1 (en) 2010-06-17 2014-01-31 Oreal AMINO ACID DERIVATIVES; COMPOSITIONS CONTAINING THEM; USE AS A TREATMENT AGENT FOR HUMAN PERSPIRATION
FR2961392A1 (en) 2010-06-17 2011-12-23 Oreal USE OF AMINO ACID DERIVATIVES AS A TREATMENT AGENT FOR HUMAN PERSPIRATION; NEW COMPOUNDS; COMPOSITIONS CONTAINING THEM
FR2962037B1 (en) 2010-07-02 2013-01-11 Oreal COSMETIC COMPOSITION COMPRISING AT LEAST ONE ORGANOPOLYSILOXANE ELASTOMER AND AT LEAST ONE TACKIFYING RESIN
FR2962036B1 (en) 2010-07-02 2012-07-27 Oreal METHOD FOR COMPLEMENTING RELIEF IMPERFECTIONS IN HOLES
US8715626B2 (en) 2010-07-30 2014-05-06 Dow Corning Toray Co., Ltd. Cosmetic for hair containing co-modified organopolysiloxane
WO2012015069A1 (en) 2010-07-30 2012-02-02 Dow Corning Toray Co., Ltd. Cosmetic for hair containing sugar alcohol-modified silicone
JP2013536299A (en) 2010-08-23 2013-09-19 ダウ コーニング コーポレーション Emulsions containing saccharide siloxane copolymer emulsifiers and methods for their preparation and use
EP2609138B1 (en) 2010-08-23 2017-05-17 Dow Corning Corporation Saccharide siloxanes stable in aqueous environments and methods for the preparation and use of such saccharide siloxanes
US9192564B2 (en) 2010-08-23 2015-11-24 Dow Corning Corporation Saccharide siloxane copolymers and methods for their preparation and use
EP2609141A1 (en) 2010-08-23 2013-07-03 Dow Corning Corporation Emulsions containing saccharide siloxane copolymer emulsifiers and methods for their preparation and use
FR2964871B1 (en) * 2010-09-17 2012-10-19 Oreal SOLID COSMETIC COMPOSITION OF MAKE-UP
FR2964870B1 (en) 2010-09-17 2012-10-19 Oreal SOLID COSMETIC COMPOSITION OF MAKE-UP
SG179379A1 (en) 2010-09-21 2012-04-27 Rohm & Haas Elect Mat Improved method of stripping hot melt etch resists from semiconductors
FR2967905B1 (en) 2010-11-25 2013-07-12 Oreal PROCESS FOR TREATING TRANSPIRATION USING A CARBONYL COMPOUND WHICH CAN BE REACTED ACCORDING TO THE MAILLARD REACTION
FR2968957B1 (en) 2010-12-15 2020-06-19 L'oreal COSMETIC COMPOSITION COMPRISING A SUPRAMOLECULAR COMPOUND CAPABLE OF ESTABLISHING HYDROGEN BONES, A SILICONE OIL AND A WAX
FR2968938B1 (en) 2010-12-21 2013-06-21 Oreal ANHYDROUS AND SOLID COSMETIC COMPOSITION
FR2968935B1 (en) 2010-12-21 2012-12-28 Oreal USE OF HYDROPHOBIC AEROGEL PARTICLES AS DEODORANT ACTIVE; METHOD OF TREATING HUMAN BODILY ODORS
US9463151B2 (en) 2010-12-27 2016-10-11 Dow Corning Toray Co., Ltd. Cosmetic containing liquid organopolysiloxane
US10076487B2 (en) 2010-12-30 2018-09-18 L'oreal Comfortable, long-wearing, transfer-resistant colored cosmetic compositions
US8945525B2 (en) 2010-12-30 2015-02-03 L'oreal Comfortable, long-wearing, transfer-resistant colored cosmetic compositions having high gloss and a non-tacky feel
US20120219516A1 (en) 2011-02-25 2012-08-30 L'oreal S.A. Cosmetic compositions having long lasting shine
KR20140035432A (en) 2011-05-30 2014-03-21 다우 코닝 도레이 캄파니 리미티드 Novel organopolysiloxane elastomer and use therefor
BR112013032810B1 (en) 2011-06-20 2018-05-02 L' Oreal Use of a flocculant polymer and cosmic process to treat sweating
FR2976805B1 (en) 2011-06-23 2013-07-12 Oreal COSMETIC COMPOSITION COMPRISING A SUPRAMOLECULAR COMPOUND CAPABLE OF ESTABLISHING HYDROGEN BONDS, AND TWO SEPARATE PARTICULATE SILICONE OILS
WO2013013902A2 (en) 2011-07-22 2013-01-31 L'oreal Method for the treatment of human perspiration using a polyvalent cation salt and an anion salt
FR2978036B1 (en) 2011-07-22 2013-07-19 Oreal PROCESS FOR TREATING TRANSPIRATION USING AN ANHYDROUS COMPOSITION COMPRISING TWO REAGENTS PRODUCING IN-SITU ASSEMBLY ON THE SKIN A TRANSPIRING EFFECT
FR2978035B1 (en) 2011-07-22 2015-03-20 Oreal USE AS ANTITRANSPIRANT OF A MULTIVALENT CATION SALT WITHOUT ANTITRANSPIRANT ALUMINUM HALOGEN OR COMPOUND SUSCEPTIBLE TO REACT WITH THIS SALT TO PRODUCE ANTITRANSPIRANT EFFECT
JP2013095835A (en) 2011-10-31 2013-05-20 Dow Corning Toray Co Ltd Long chain amide-modified silicone/amino-modified silicone copolymer and use of the same
JP2013095834A (en) 2011-10-31 2013-05-20 Dow Corning Toray Co Ltd Long chain hydrocarbon-modified silicone/amino-modified silicone copolymer and use of the same
EP2785908A1 (en) 2011-11-29 2014-10-08 Dow Corning Corporation Aminofunctional silicone emulsions for fiber treatments
FR2983406B1 (en) 2011-12-05 2014-03-28 Oreal COSMETIC COMPOSITION FOR COATING KERATINIC FIBERS
FR2984089B1 (en) 2011-12-20 2014-01-10 Oreal APPLICATION DEVICE COMPRISING A COMPOSITION BASED ON HYDROPHOBIC FILMOGENIC POLYMER AND A VOLATILE SOLVENT, PROCESS FOR TREATING KERATINOUS FIBERS USING THE SAME
FR2984142B1 (en) 2011-12-20 2013-12-20 Oreal COMPOSITION COMPRISING A PARTICULAR ACRYLIC POLYMER AND SILICONE COPOLYMER, PROCESS FOR TREATING KERATINOUS FIBERS USING THE SAME
FR2984140B1 (en) 2011-12-20 2014-06-20 Oreal COMPOSITION COMPRISING A FATTY PHASE, A STRUCTURING AGENT, A COMPOUND AND / OR A HYDROPHILIC ACTIVE INGREDIENT
FR2984143B1 (en) 2011-12-20 2014-07-11 Oreal PROCESS FOR APPLYING A PARTICULAR ACRYLIC POLYMER PIGMENT COLORING COMPOSITION AND SILICONE COPOLYMER, AND APPROPRIATE DEVICE
FR2984132B1 (en) 2011-12-20 2014-08-01 Oreal PIGMENT COMPOSITION BASED ON PARTICULAR ACRYLIC POLYMER AND SILICONE COPOLYMER, COLORING PROCESS
WO2013093802A2 (en) 2011-12-20 2013-06-27 L'oreal Composition comprising a polyamide resin, a gelling system, a polar oil and an apolar oil
FR2984699B1 (en) 2011-12-22 2014-01-24 Oreal LIP MAKE-UP KIT, COSMETIC PRODUCT APPLICATOR, AND MAKE-UP PROCESS USING THE SAME
FR2984698B1 (en) 2011-12-22 2014-01-24 Oreal LIP MAKE-UP KIT, COSMETIC PRODUCT APPLICATOR, AND MAKE-UP PROCESS USING THE SAME
JP6369888B2 (en) 2011-12-27 2018-08-08 東レ・ダウコーニング株式会社 Novel liquid organopolysiloxane and use thereof
FR2989889B1 (en) 2012-04-26 2016-12-30 Oreal COSMETIC COMPOSITION COMPRISING SILANE AND LIPOPHILIC THICKENER
FR2990850B1 (en) 2012-05-25 2014-05-16 Oreal COSMETIC COMPOSITION COMPRISING THE ASSOCIATION OF A LIPOPHILIC DERIVATIVE OF SALICYLIC ACID, AN ANTI-TRANSPIRANT ALUMINUM SALT OR COMPLEX, AND AN ACETIC N, DIACIDAL AMINO ACID SALT
WO2013190469A2 (en) 2012-06-19 2013-12-27 L'oreal Cosmetic process for making up and/or caring for the lips
FR2992196B1 (en) 2012-06-21 2014-10-31 Oreal LIQUID COSMETIC COMPOSITION COMPRISING OIL, HYDROPHOBIC SILICA AEROGEL PARTICLES AND ETHYLENE COPOLYMER SEQUENCE
FR2992193B1 (en) 2012-06-21 2014-11-07 Oreal LIQUID COSMETIC COMPOSITION COMPRISING AN OIL, HYDROPHOBIC SILICA AEROGEL PARTICLES, AND A FUSION TEMPERATURE WAX GREATER THAN 60 ° C
FR2992195B1 (en) 2012-06-21 2014-11-07 Oreal COSMETIC COMPOSITION COMPRISING AN OIL, HYDROPHOBIC SILICA AEROGEL PARTICLES AND A HYDROCARBON SEQUENCE COPOLYMER PREFERABLY OBTAINED FROM AT LEAST ONE STYRENE MONOMER
FR2992215B1 (en) 2012-06-21 2014-10-31 Oreal ANHYDROUS COSMETIC COMPOSITION COMPRISING AN OIL, HYDROPHOBIC SILICA AEROGEL PARTICLES, A HYDROPHILIC ACTIVE INGREDIENT AND AT LEAST ONE SURFACTANT
FR2992207B1 (en) 2012-06-21 2014-10-31 Oreal COSMETIC COMPOSITION COMPRISING OIL, HYDROPHOBIC SILICA AEROGEL PARTICLES, AND SEMI-CRYSTALLINE POLYMER
FR2992206B1 (en) 2012-06-21 2014-07-18 Oreal COSMETIC COMPOSITION COMPRISING AN OIL, HYDROPHOBIC SILICA AEROGEL PARTICLES AND A HYDROCARBON RESIN
FR2992211B1 (en) 2012-06-21 2014-10-31 Oreal LIQUID COSMETIC COMPOSITION COMPRISING OIL, HYDROPHOBIC SILICA AEROGEL PARTICLES, AND NON-POLYMERIC ORGANOGELER
FR2992559B1 (en) 2012-06-29 2014-06-20 Oreal BILOKE PROCESS FOR COLORING KERATIN FIBERS
FR2993453B1 (en) 2012-07-20 2016-05-13 Oreal COSMETIC COMPOSITION FOR COATING KERATINIC FIBERS
JP5797618B2 (en) 2012-08-22 2015-10-21 東レ・ダウコーニング株式会社 Copolymer having carbosiloxane dendrimer structure, and composition and cosmetic containing the same
EP2906194B1 (en) 2012-10-11 2018-06-06 Dow Corning Corporation Aqueous silicone polyether microemulsions
FR2996756B1 (en) 2012-10-15 2020-06-05 L'oreal COSMETIC USE OF A SINGLE-UNSATURATED FATTY ACID OR ONE OF ITS SALTS AND / OR ITS ESTERS AS A DEODORING ACTIVE INGREDIENT
FR2996762B1 (en) 2012-10-15 2014-11-21 Oreal COSMETIC COMPOSITION FOR COATING KERATINIC FIBERS
FR2996759B1 (en) 2012-10-15 2015-01-16 Oreal COSMETIC COMPOSITION FOR COATING KERATINIC FIBERS
FR2996757B1 (en) 2012-10-15 2015-01-02 Oreal COSMETIC COMPOSITION FOR COATING KERATINIC FIBERS
FR2998782B1 (en) 2012-11-30 2015-04-17 Oreal WATER-IN-OIL COSMETIC EMULSION, PARTICULARLY CONDITIONED IN THE FORM OF AEROSOL COMPRISING AT LEAST ONE VINYL POLYMER, AT LEAST ONE OLEFIN COPOLYMER AND AT LEAST ONE ANTI-TRANSPARENT ACTIVE INGREDIENT
EP2928438B1 (en) 2012-12-04 2018-08-15 L'oreal Solid powdery cosmetic composition
US10406092B2 (en) 2012-12-28 2019-09-10 Dow Silicones Corporation Method for producing transparent or semi-transparent liquid glycerin-derivative-modified silicone composition
FR3002448B1 (en) 2013-02-25 2015-04-03 Oreal COSMETIC COMPOSITION OF GEL TYPE
FR3004343B1 (en) 2013-04-12 2015-06-19 Oreal COSMETIC COMPOSITION OF GEL TYPE
FR3004940B1 (en) 2013-04-26 2015-05-22 Oreal COSMETIC USE OF AN ESSENTIAL OIL OF SATUREJA MONTANA RICH IN GERANIOL AS ACTIVE DEODORANT
FR3011740B1 (en) 2013-10-11 2015-10-23 Oreal COSMETIC COMPOSITION FOR COATING KERATINIC FIBERS
FR3011741B1 (en) 2013-10-11 2015-10-23 Oreal COSMETIC COMPOSITION FOR COATING KERATINIC FIBERS
KR101902167B1 (en) 2014-04-28 2018-10-01 다우 실리콘즈 코포레이션 Cross-linked composition and cosmetic composition comprising the same
EP2939655A1 (en) 2014-04-30 2015-11-04 L'Oréal Composition comprising microcapsules containing reflective particles
EP2939653A1 (en) 2014-04-30 2015-11-04 L'Oréal Composition comprising microcapsules containing particles with a high wet point
EP2939654A1 (en) 2014-04-30 2015-11-04 L'Oréal Composition comprising microcapsules containing silicone elastomer
FR3021533B1 (en) 2014-05-28 2017-09-15 Oreal COSMETIC COMPOSITION OF GEL TYPE
FR3023475B1 (en) 2014-07-09 2016-07-22 Oreal ANHYDROUS SOLID COSMETIC OR DERMATOLOGICAL COMPOSITION BASED ON BENEFICIAL AGENT RELEASE PARTICLES
FR3023477B1 (en) 2014-07-10 2017-11-24 Oreal COSMETIC USE OF SPICULISPORIC ACID AS DEODORANT ACTIVE
KR101916655B1 (en) 2014-07-23 2018-11-08 다우 실리콘즈 코포레이션 Pituitous silicone fluid
FR3025096B1 (en) 2014-08-28 2016-12-23 Oreal GEL / GEL COMPOSITION CONTAINING ANTI-TRANSPARENT ACTIVE INGREDIENT
FR3025099B1 (en) 2014-08-28 2016-12-16 Oreal GEL-TYPE COSMETIC COMPOSITION IMPROVED AND NOT COLLAPSIBLE
FR3025075A1 (en) 2014-08-28 2016-03-04 Oreal NEW CARE AND / OR MAKE-UP DEVICE COMPRISING A GEL / GEL ARCHITECTURE COMPOSITION
FR3025097B1 (en) 2014-08-28 2016-12-23 Oreal GEL / GEL COMPRISING AT LEAST TWO LOOSE EFFECTS
FR3025100B1 (en) 2014-08-28 2016-12-09 Oreal GEL-TYPE COSMETIC COMPOSITION IMPROVED
FR3028751B1 (en) 2014-11-24 2018-01-05 L'oreal POWDER SYNTHETIC PHYLLOSILICATE AS A MATIFYING AGENT AND / OR HOMOGENIZING APPLICATION
FR3028753B1 (en) 2014-11-24 2018-01-05 L'oreal AQUEOUS OR HYDRO-ALCOHOLIC GEL OF SYNTHETIC PHYLLOSILICATES AS A VISCOSING AGENT, MATIFIING AND / OR HOMOGENIZING APPLICATION
FR3032613B1 (en) 2014-12-12 2017-02-17 Oreal DEODORANT EMULSION CONTAINING A MIXTURE OF ALKYLPOLYGLYCOSIDE AND FATTY ALCOHOL, AN ASSOCIATIVE NON-IONIC POLYURETHANE POLYETHER, A VOLATILE HYDROCARBON OIL
FR3030232A1 (en) 2014-12-18 2016-06-24 Oreal METHOD OF MAKE-UP OF COSMETIC COMPOSITIONS COMPRISING A HIGH CONTENT OF POLYMER IN DISPERSION OR SOLUTION
CN107207740B (en) 2014-12-19 2020-03-17 美国陶氏有机硅公司 Method for preparing functionalized particles
FR3031297A1 (en) 2015-01-07 2016-07-08 Oreal MASCARA SOLVENTS VOLATILE HYDROCARBONS AND SILICONES
FR3031299A1 (en) 2015-01-07 2016-07-08 Oreal MICROCAR MASK OF CARNAUBA
FR3031298A1 (en) 2015-01-07 2016-07-08 Oreal MASCARA SUNFLOWER WAX AND VOLATILE HYDROCARBON OIL
CN107667147A (en) 2015-04-08 2018-02-06 美国道康宁公司 Mucilaginous substance silicone fluid composition
EP3280771A1 (en) 2015-04-08 2018-02-14 Dow Corning Corporation Pituitous silicone emulsions
KR20170133490A (en) 2015-04-08 2017-12-05 다우 코닝 코포레이션 Fluid compositions and personal care
FR3041252B1 (en) 2015-09-18 2019-01-25 Capsum STABLE DISPERSIONS OF DROPS COMPRISING A GELIFYING AGENT
US10793673B2 (en) 2015-11-10 2020-10-06 Iowa State University Research Foundation, Inc. Bioadvantaged nylon: polycondensation of 3-hexenedioic acid with hexamethylenediamine
ES2892498T3 (en) 2015-12-17 2022-02-04 Oreal Gel/gel-like composition based on hydrophobic coated pigments and a glycol compound
JP6652513B2 (en) 2016-03-03 2020-02-26 信越化学工業株式会社 Bioelectrode manufacturing method
CN109069368A (en) 2016-04-27 2018-12-21 美国陶氏有机硅公司 Hydrophilic silane
JP6549517B2 (en) 2016-05-09 2019-07-24 信越化学工業株式会社 Bioelectrode and method of manufacturing the same
US10982052B2 (en) 2016-05-10 2021-04-20 Dow Silicones Corporation Silicone block copolymer having an aminofunctional endblocking group and method for its preparation and use
US10865330B2 (en) 2016-07-28 2020-12-15 3M Innovative Properties Company Segmented silicone polyamide block copolymers and articles containing the same
CN109476815B (en) 2016-07-28 2021-05-04 3M创新有限公司 Segmented silicone polyamide block copolymers and articles comprising the same
US10688034B2 (en) 2016-07-29 2020-06-23 L'oreal Long-wearing, transfer-resistant cosmetic composition having improved tackiness
US10687601B2 (en) 2016-07-29 2020-06-23 L'oreal Cosmetic care system
JP6744848B2 (en) 2016-09-13 2020-08-19 信越化学工業株式会社 Adhesive composition, bioelectrode, and method for producing bioelectrode
KR102298821B1 (en) 2016-09-19 2021-09-09 다우 실리콘즈 코포레이션 Personal Care Composition Comprising Polyurethane-Polyorganosiloxane Copolymer
EP3515961A1 (en) 2016-09-19 2019-07-31 Dow Silicones Corporation Polyurethane-polyorganosiloxane copolymer and method for its preparation
WO2018052648A1 (en) 2016-09-19 2018-03-22 Dow Corning Corporation Copolymer composition for personal care
JP6761386B2 (en) 2016-09-29 2020-09-23 信越化学工業株式会社 Adhesive composition, bioelectrode, method for producing bioelectrode, and salt
JP6761384B2 (en) * 2016-09-29 2020-09-23 信越化学工業株式会社 Adhesive composition, bioelectrode, and method for manufacturing bioelectrode
FR3057768B1 (en) 2016-10-26 2018-12-07 Capsum DOUBLE EMULSIONS COMPRISING A GELIFIED FAT PHASE
FR3057767B1 (en) 2016-10-26 2018-12-07 Capsum DOUBLE EMULSIONS WITH DOUBLE COACERVAT
FR3061006B1 (en) 2016-12-22 2020-10-02 Oreal SOLID COSMETIC COMPOSITION CONSISTING OF A SILICONE POLYAMIDE, A SILICONE RESIN AND A DISPERSE AQUEOUS PHASE
FR3061002B1 (en) 2016-12-23 2019-05-24 L'oreal COMPOSITION COMPRISING HYDROXYETHYLPIPERAZINE ETHANE SULFONIC ACID AND AT LEAST ONE ALKYLPOLYGLUCOSIDE
FR3061429B1 (en) 2016-12-29 2020-11-27 Oreal ANHYDROUS COMPOSITION INCLUDING A MAGNESIUM SALT
JP6919993B2 (en) 2017-01-06 2021-08-18 信越化学工業株式会社 Bioelectrode composition, bioelectrode and method for producing bioelectrode
US20180214370A1 (en) 2017-01-31 2018-08-02 L'oreal Topcoat for long-wear lip compositions
JP6966310B2 (en) 2017-02-06 2021-11-10 信越化学工業株式会社 Bioelectrode composition, bioelectrode, method for producing bioelectrode, and polymer compound
JP6836520B2 (en) 2017-02-14 2021-03-03 信越化学工業株式会社 Bioelectrode composition, bioelectrode, and method for producing bioelectrode
JP6892376B2 (en) 2017-02-14 2021-06-23 信越化学工業株式会社 Bioelectrode composition, bioelectrode, method for producing bioelectrode, and polymer compound
US20210177726A1 (en) 2017-02-15 2021-06-17 Dow Silicones Corporation Personal care compositions including a polyurethane - polyorganosiloxane copolymer
FR3063899B1 (en) 2017-03-17 2019-04-19 Capsum COMPOSITIONS COMPRISING A FATTY PHASE AND AQUEOUS PHASE IN THE FORM OF SOLID SPHERES
FR3067930B1 (en) 2017-06-27 2020-01-10 Capsum DISPERSIONS COMPRISING AT LEAST ONE HYDROCARBON VOLATILE OIL
JP7153016B2 (en) 2017-06-28 2022-10-13 ダウ・東レ株式会社 Cosmetic film-forming agent and cosmetics containing the same
FR3070858B1 (en) 2017-09-14 2020-02-21 Capsum DISPERSION WITH HIGH FAT PIGMENT DISPERSE PHASE
FR3072029A1 (en) 2017-10-09 2019-04-12 L'oreal METHOD FOR TREATING HUMAN TRANSPIRATION USING A CATION AND ANION IN THE PRESENCE OF A MODULATOR
WO2019099180A1 (en) 2017-11-20 2019-05-23 Dow Silicones Corporation Crosslinked aminosilicone polymer and methods for its preparation and use
FR3075053B1 (en) 2017-12-15 2020-07-10 L'oreal PIGMENT-BASED GEL / GEL-LIKE COMPOSITION OF AT LEAST ONE C3-C8 SATURATED LINEAR DIHYDROXYALKANE, OF SALICYLIC ACID IN FREE FORM
FR3076218B1 (en) 2017-12-28 2019-12-27 L'oreal GEL COMPOSITION COMPRISING AN AQUEOUS WAX (S) MICRODISPERSION
US20190262257A1 (en) 2018-02-28 2019-08-29 L'oreal Matte lip compositions
JP6839125B2 (en) 2018-04-02 2021-03-03 信越化学工業株式会社 Bioelectrode composition, bioelectrode, and method for producing bioelectrode
WO2019243613A1 (en) 2018-06-22 2019-12-26 L' Oreal Emulsion comprising an alkylpolyglycoside and nacres, and makeup and/or care process using same
JP7158335B2 (en) 2018-06-25 2022-10-21 信越化学工業株式会社 Bioelectrode composition, bioelectrode, and method for producing bioelectrode
JP7111653B2 (en) 2018-06-25 2022-08-02 信越化学工業株式会社 Bioelectrode composition, bioelectrode, and method for producing bioelectrode
JP7099990B2 (en) 2018-06-26 2022-07-12 信越化学工業株式会社 Bioelectrode composition, bioelectrode, and method for manufacturing bioelectrode
US11234606B2 (en) 2018-07-05 2022-02-01 Shin-Etsu Chemical Co., Ltd. Bio-electrode composition, bio-electrode, and method for manufacturing a bio-electrode
JP6966389B2 (en) 2018-07-12 2021-11-17 信越化学工業株式会社 Bioelectrode composition, bioelectrode, and method for manufacturing bioelectrode
JP6966396B2 (en) 2018-08-23 2021-11-17 信越化学工業株式会社 Bioelectrode composition, bioelectrode, and method for manufacturing bioelectrode
JP6966397B2 (en) 2018-08-27 2021-11-17 信越化学工業株式会社 Bioelectrode composition, bioelectrode, and method for manufacturing bioelectrode
WO2020061000A1 (en) * 2018-09-17 2020-03-26 Elevance Renewable Sciences, Inc Segmented silicone polymers and methods of making and using the same
US11306184B2 (en) 2018-09-17 2022-04-19 Wilmar Trading Pte. Functionalized silicone polymers and methods of making and using the same
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Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3218344A (en) 1959-06-29 1965-11-16 Union Carbide Corp Alkoxy substituted organosilicon compounds
US3313773A (en) 1965-12-03 1967-04-11 Gen Electric Platinum addition catalyst system
US3392143A (en) 1967-05-15 1968-07-09 Gen Electric Polyamide compositions
US3746738A (en) 1972-03-28 1973-07-17 Union Carbide Corp Silicon containing polyazimides
US3892643A (en) 1973-05-02 1975-07-01 Hitachi Ltd Thermally curable compositions and process for curing said compositions
US4145508A (en) 1976-08-17 1979-03-20 Rhone-Poulenc Industries Polysiloxane thermoplastic elastomers
US5874069A (en) 1997-01-24 1999-02-23 Colgate-Palmolive Company Cosmetic composition containing silicon-modified amides as thickening agents and method of forming same
US5919441A (en) 1996-04-01 1999-07-06 Colgate-Palmolive Company Cosmetic composition containing thickening agent of siloxane polymer with hydrogen-bonding groups
US6051216A (en) 1997-08-01 2000-04-18 Colgate-Palmolive Company Cosmetic composition containing siloxane based polyamides as thickening agents

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2249325A1 (en) * 1996-04-01 1997-10-09 Colgate-Palmolive Company Cosmetic composition containing amides and silicon-modified waxes

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3218344A (en) 1959-06-29 1965-11-16 Union Carbide Corp Alkoxy substituted organosilicon compounds
US3313773A (en) 1965-12-03 1967-04-11 Gen Electric Platinum addition catalyst system
US3392143A (en) 1967-05-15 1968-07-09 Gen Electric Polyamide compositions
US3746738A (en) 1972-03-28 1973-07-17 Union Carbide Corp Silicon containing polyazimides
US3892643A (en) 1973-05-02 1975-07-01 Hitachi Ltd Thermally curable compositions and process for curing said compositions
US4145508A (en) 1976-08-17 1979-03-20 Rhone-Poulenc Industries Polysiloxane thermoplastic elastomers
US5919441A (en) 1996-04-01 1999-07-06 Colgate-Palmolive Company Cosmetic composition containing thickening agent of siloxane polymer with hydrogen-bonding groups
US5874069A (en) 1997-01-24 1999-02-23 Colgate-Palmolive Company Cosmetic composition containing silicon-modified amides as thickening agents and method of forming same
US6051216A (en) 1997-08-01 2000-04-18 Colgate-Palmolive Company Cosmetic composition containing siloxane based polyamides as thickening agents

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030105260A1 (en) * 2001-07-12 2003-06-05 Cook Leon Neal Methods for making silicone-organic copolymers
US6800713B2 (en) * 2001-07-12 2004-10-05 Dow Corning Corporation Methods for making silicone-organic copolymers
US20100210491A1 (en) * 2009-02-13 2010-08-19 Charles Piskoti Silicone Wax Emulsion and Method of Manufacture
US9006157B2 (en) 2009-02-13 2015-04-14 Genesee Polymers Corp. Silicone wax emulsion and method of manufacture
US9872828B2 (en) 2014-05-21 2018-01-23 Dow Corning Corporation Emulsion of cross-linked aminosiloxane polymer
US9890253B2 (en) 2014-05-21 2018-02-13 Dow Corning Corporation Cross-linked aminosiloxane polymer and method of forming
US10059806B2 (en) 2014-05-21 2018-08-28 Dow Silicones Corporation Aminosiloxane polymer and method of forming
WO2018165434A1 (en) 2017-03-08 2018-09-13 Dow Silicones Corporation Long lasting cosmetic composition comprising silicone elastomer
US10918587B2 (en) 2017-03-08 2021-02-16 Dow Silicones Corporation Long lasting cosmetic composition comprising silicone elastomer

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