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  • 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
  • C08G77/48—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
  • C08G77/50—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages
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  • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
  • A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
  • A01N25/10—Macromolecular compounds
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  • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
  • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
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  • 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
  • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
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  • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
  • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
• • A—HUMAN NECESSITIES
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  • 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
  • A61K8/895—Polysiloxanes containing silicon bound to unsaturated aliphatic groups, e.g. vinyl dimethicone
• • A—HUMAN NECESSITIES
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  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P17/00—Drugs for dermatological disorders
• • A—HUMAN NECESSITIES
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  • A61Q19/00—Preparations for care of the skin
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  • C05G3/00—Mixtures of one or more fertilisers with additives not having a specially fertilising activity
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  • C05G3/00—Mixtures of one or more fertilisers with additives not having a specially fertilising activity
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  • C05G3/00—Mixtures of one or more fertilisers with additives not having a specially fertilising activity
  • C05G3/70—Mixtures of one or more fertilisers with additives not having a specially fertilising activity for affecting wettability, e.g. drying agents
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  • C05G5/00—Fertilisers characterised by their form
  • C05G5/20—Liquid fertilisers
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  • C05G5/00—Fertilisers characterised by their form
  • C05G5/30—Layered or coated, e.g. dust-preventing coatings
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  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/02—Silicon compounds
  • C07F7/08—Compounds having one or more C—Si linkages
  • C07F7/0834—Compounds having one or more O-Si linkage
  • C07F7/0838—Compounds with one or more Si-O-Si sequences
• • C—CHEMISTRY; METALLURGY
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  • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
  • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
  • C08F220/10—Esters
  • C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
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  • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
  • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
  • C08F220/10—Esters
  • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
  • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
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  • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
  • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
  • C08F220/52—Amides or imides
  • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
  • C08F220/56—Acrylamide; Methacrylamide
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  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
  • C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
  • C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
• • 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
  • C08G77/48—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
  • C08G77/485—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms containing less than 25 silicon atoms
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  • 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
  • C08G77/60—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 in which all the silicon atoms are connected by linkages other than oxygen atoms
• • C—CHEMISTRY; METALLURGY
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  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
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  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
  • C09D133/04—Homopolymers or copolymers of esters
  • C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
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  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/10—General cosmetic use

Definitions

• the present invention relates to a composition comprising novel mono-acrylate functionalized organo modified carbosiloxane monomer that exhibits improved hydrolytic stability under acidic, basic and neutral pH conditions in comparison to the corresponding conventional siloxane monomer. More particularly the present invention relates to improved compositions comprising hydrolytic stability at the pH of 6.5, 7.0 and 7.5.
• Siloxane based hydrogels are used for variety of applications in the area of health care, personal care, agriculture, coatings, home care etc, because of their water absorbing and high oxygen permeable nature.
• these silicone hydrogels show poor hydrolytic stability under acidic or basic pH conditions. This effect is predominant when the siloxane chain length is too small.
• the trisiloxane-based compounds are well known to undergo rapid hydrolytic cleavage under acidic or basic pH conditions.
• the instant invention discloses siloxane compositions that are hydrolytically more stable and can be used to form hydrolytically stable silicone hydrogel copolymer that can be potentially used for various applications, including those cited above.
• Carbomer is a generic name for synthetic high molecular weight polymers of acrylic acid used as thickening, dispersing, suspending and emulsifying agents in pharmaceuticals and cosmetics. They may be homopolymers of acrylic acid, as well as copolymers with methacrylic acid and other acrylates.
• An object of the present invention is to provide a mono-acrylate functional organo-modified carbosiloxane composition
• R 1 R 2 R 3 Si -Y 1 - [Si(R 4 R 5 )(Y 2 )] a - Si(R 6 R 7 ) - Z (I) wherein a is 0 to about 100; Y is a substituted or unsubstituted divalent alkyl linking group of 1 to about 10 carbon atoms; Y 2 is a substituted or unsubstituted divalent alkyl linking group of 1 to about 10 carbon atoms or a hetero atom such as nitrogen, oxygen or sulfur; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are independently selected from the group consisting of monovalent aliphatic, cycloaliphatic or aromatic hydrocarbon groups of 1 to about 10 carbons and halogenated hydrocarbon groups of 1 to about 10 carbons, -Y 2 -Si(R 8 R 9 R 10 ) and A, wherein R 8 R 9 R 10 are independently selected from the group consisting of monovalent alipha
• R 1 is a linear or branched, divalent alkyl linking group having 0 to about 20 carbon atoms
• B is a divalent hydrophilic or hydrophobic moiety selected from the group consisting of substituted or unsubstituted, saturated and unsaturated aliphatic, cycloaliphatic or aromatic hydrocarbons and substituted or unsubstituted, saturated and unsaturated aliphatic, cycloaliphatic or aromatic hydrocarbons containing hetero atoms
• X is acrylamide or a polymerizable group having the following general formula (III)
• R 12 , R 13 , and R 4 is hydrogen or a substituted or unsubstituted saturated monovalent hydrocarbon group of 1 to about 20 carbons.
• Another object of the present invention is to provide a silicone composition comprising homo and copolymers derived from the monomers described herein.
• Another object of the present invention is to provide a carbomer- containing composition exhibiting a high level of dispersion of its carbomer component, useful in the preparation of various personal care products, cosmetics and the like.
• the inventive composition and formulations made there from are efficiently and effectively realized employing conventional equipment and standard manufacturing practices.
• Another embodiment of the present invention is directed to a process for producing the described silicone monomers comprising chemically reacting a silicone-containing compound having the general formula shown below
• R 1 R 2 R 3 Si -Y 1 - [Si(R 4 R 5 )(Y 2 )] a - Si(R 6 R 7 ) - H (IV) wherein a is 0 to 100; Y 1 is a substituted or unsubstituted divalent alkyl linking group of 1 to 10 carbon atoms, and Y 2 can be the same as Y 1 or a hetero atom such as nitrogen, oxygen or sulfur.
• R 1 to R 7 is independently selected from the group consisting of monovalent aliphatic, cycloaliphatic or aromatic hydrocarbon groups of 1 to about 10 carbons and halogenated hydrocarbon groups of 1 to about 10 carbons.
• R -R 7 can be -Y 2 -Si(R 8 R 9 R 10 ) and A, wherein R 8 to R 10 is independently selected from the group consisting of monovalent aliphatic, cycloaliphatic or aromatic hydrocarbon groups of 1 to about 10 carbons and halogenated hydrocarbon groups of 1 to about 10 carbons.
• A can be a monovalent hydrophilic or hydrophobic moiety selected from the group consisting of, substituted or unsubstituted, saturated and unsaturated aliphatic, cycloaliphatic or aromatic hydrocarbons and optionally contains hetero atoms.
• R 15 is a linear or branched unsaturated alkyl group having about 0 to about 20 carbon atoms
• B is divalent moiety selected from the group consisting of substituted or unsubstituted, saturated and unsaturated aliphatic, cycloaliphatic or aromatic hydrocarbons and substituted or unsubstituted, saturated and unsaturated aliphatic, cycloaliphatic or aromatic hydrocarbons containing hetero atoms;
• B comprises functionalities such as alcohols, ethers, esters, amides, amines, acids and its salts, cyano, thio, urethane, urea, sulfonates, sulphonamides, phosphates and their combinations.
• M can be hydroxyl or halogen or epoxy or carboxylic acid group.
• G can be a halogen or hydroxyl or alkyloxy having 1 to 10 carbon atoms.
• R 12 to R 14 can be selected from hydrogen or a substituted or unsubstituted saturated monovalent hydrocarbon group of 1 to about 20 carbons to produce said silicone monomer.
• the reaction of the functionalized carbosiloxane with alkylacryloyl compound having the general formula (VI) can be carried out in the presence of a tertiary amine base or basic ion-exchange resin (IER) or azeotrope-forming solvent or reactant.
• the azeotrope-forming solvent can be selected from hexane, heptane, toluene etc. and the reactant such as methylmethacrylate under the inert reaction conditions.
• Figure 1 is a graphical representation of hydrolytic stability data obtained for monomers produced in Ex.1 and CEx.2 at 85°C under different pH conditions; (A) pH 6.5, (B) pH 7.0 and (C) pH 7.5.
• compositions comprising mono- acrylate and methacrylate functionalized carbosiloxane monomers that are non-bulky and show improved hydrolysis resistance are provided.
• Carbosiloxane monomers of the present invention showed improved hydrolysis resistance under acidic and basic pH conditions in comparison to the corresponding conventional siloxane monomers. Cured compositions produced from these monomers showed better oxygen permeability, and surface wettability and lower modulus in comparison to compositions/films of the corresponding conventional siloxane monomers.
• homopolymers are polymers made from the same repeating monomer and 'copolymers" are polymers wherein the polymer contains at least two structurally different monomers.
• Notations such as (meth)acrylate denote monomer with either acrylate or methacrylate functionality.
• compositions comprising (meth)acrylate functionalized silicone monomers/polymers of the present invention, products made from these compositions as well as their preparation are further described in the sections below.
• the monomers disclosed have a carbosilane linkage, -Si-(CH 2 ) n -Si-, which makes it possible to produce compositions having hydrolytically stable (hydrolysis resistance) monomers and polymers.
• the present invention is directed to compositions comprising linear mono-acrylate functional organo-modified carbosiloxane compounds useful as a hydrolytically stable silicone monomer.
• the mono- acrylate functional carbosiloxane monomers of the present invention have the general structure shown in formula (I): (R 1 R 2 R 3 )Si -Y 1 - [Si(R 4 R 5 )(Y 2 )] a - Si(R 6 R 7 ) - Z (I).
• One of the preferred variants of the formula (I) of the present invention is the mono acrylate functional monomer having the general formula as shown below.
• R 1 to R 7 is independently selected from the group consisting of monovalent aliphatic, cycloaliphatic or aromatic hydrocarbon groups of 1 to about 10 carbons and halogenated hydrocarbon groups of 1 to about 10 carbons.
• R 1 -R 7 can also be independently selected from -Y 2 - Si(R 8 R 9 R 10 ) and A, where R 8 to R 10 is independently selected from the group consisting of monovalent aliphatic, cycloaliphatic or aromatic hydrocarbon groups of 1 to about 10 carbons and halogenated hydrocarbon groups of 1 to about 10 carbons.
• A can be a monovalent hydrophilic or hydrophobic moiety selected from the group consisting of, substituted or unsubstituted, saturated and unsaturated aliphatic, cycloaliphatic or aromatic hydrocarbons and optionally contains hetero atoms.
• A comprises functionalities such as alkyl, alcohol, ether, ester, amide, amine, acid and its salts, cyano, thio, urethane, urea, sulfonate, sulphonamide, phosphate and their combinations.
• R 11 is a linear or branched, divalent alkyl linking group having about 0 to about 20 carbon atoms.
• B in general formula (II) is a divalent moiety selected from the group consisting of, substituted or unsubstituted, saturated and unsaturated aliphatic, cycloaliphatic or aromatic hydrocarbons and substituted or unsubstituted, saturated and unsaturated aliphatic, cycloaliphatic or aromatic hydrocarbons containing hetero atoms;
• B comprises functionalities such as alcohols, ethers, esters, amides, amines, acids and its salts, cyano, thio, urethane, urea, sulfonates, sulphonamides, phosphates and their combinations.
• p and q are independently 0 to about 100; r is 0 to about 50 and (p +q + r) is greater than 0.
• X is a polymerizable group having the general formula (III)
• R 12 to R 14 can be selected from hydrogen or a substituted or unsubstituted saturated monovalent hydrocarbon group of 1 to about 20 carbons or X is acrylamide.
• the present invention is also directed to compositions comprising polymers formed by the reaction products of the carbosiloxane monomers provided herein.
• These polymers may be homopolymers of one of the monomers of the present invention or copolymers of two structurally different silicone monomers of the present invention, and/or copolymers of one or more silicone monomers of the present invention and at least one other hydrophilic unsaturated organic monomers suitable for use in silicone hydrogels, with preferred non-limiting examples of such being ⁇ , ⁇ -dimethylacrylamide, 2- hydroxy-ethylmethacrylate (HEMA), 2-hydroxy ethylacrylate (HEA), N- vinylpyrrolidone, and methacrylic acid.
• HEMA 2- hydroxy-ethylmethacrylate
• HAA 2-hydroxy ethylacrylate
• N- vinylpyrrolidone and methacrylic acid.
• the ratio of the silicone monomers of the present invention to the other hydrophilic unsaturated organic monomers is from about 1 :100 to about 100:1 and preferably from about 20:80 to about 90:10 and more preferably from about 30:70 to about 80:20.
• the unsaturated organic monomers and the carbosiloxane monomers of this invention are mutually miscible and form homogeneous mixtures.
• the use of compatibilizing solvents is not necessary.
• the carbosiloxane monomers of this invention are also either water-soluble or water- dispersible. Water-soluble carbosiloxane monomers are miscible with water in all proportions to yield homogeneous solutions. Water-dispersible carbosiloxane monomers do not dissolve completely in water. Cloudiness, haze, colloid formation and similar visible signs of heterogeneity in the aqueous mixture are indicative of dispersion rather than solution.
• Both water solubility and water dispersibility are desirable features of the carbosiloxane monomers of the instant invention.
• the carbosiloxane monomers contain a methacrylated ethoxylated polyether segment, water dispersibility is observed when the polyether content is less than about 60 weight percent of the total molecular weight, and water solubility when the polyether segment is greater than about 60 weight percent.
• compositions comprising polymers
• the polymers Prior to forming compositions comprising polymers, the polymers are formed by mixing the desired monomers and the resulting mixture is polymerized and cured to form transparent thin films by known thermal techniques using free radical or cationic or anionic initiators and UV cure techniques using photoinitiators in the presence of crosslinking agents.
• the monomers added to the reaction mixture to form the polymers may be monomers or prepolymers.
• a "prepolymer” is a reaction intermediate polymer of medium molecular weight having polymerizable groups.
• silicone-containing monomers “carbosiloxane monomers” and “hydrophilic monomers” include prepolymers.
• One preferred variant of carbosiloxane monomer from structure (I) of the present invention has the following formula
• B is a divalent polyether as shown in the representative example with p being 0 to about 100, preferably 2 to about 15, more preferably about 8, and q and r equal to 0;
• Y 1 is a divalent alkyl-linking group of about 1 to 10 carbons, preferably 1 to about 5 carbons, more preferably about 2 carbons.
• Y 2 is a combination of divalent heteroatom and divalent alkyl group and X is polymerizable methacrylate group, a is 0 to about 100, more preferably 0 to 20 inclusive, and even more preferably 1.
• Each of the R groups in the general monomer structure (I) is a monovalent alkyl-linking group, preferably a methyl group.
• R to R 7 can also be selected from -Y 2 -Si(R 8 R 9 R 10 ) and A.
• B is a divalent hydroxyl containing cycloaliphatic ring
• X is polymerizable methacrylate group
• a is 0 to about 100, more preferably 0 to about 20 inclusive, and even more preferably 1.
• Y 1 is a divalent alkyl-linking group of about 1 to 10 carbons, preferably 1 to about 5 carbons, more preferably about 2 carbons.
• Y 2 is a combination of divalent heteroatom and divalent alkyl group.
• Each of the R groups in the general monomer structure (I) is a monovalent alkyl-linking group, preferably a methyl group.
• R 1 to R 7 can also be selected from -Y 2 -Si(R e R 9 R 10 ) and A.
• B is a divalent alkyl group
• X is polymerizable methacrylate group
• a is 0 to about 100, more preferably 0 to about 20 inclusive, and even more preferably 1.
• Y 1 is a divalent alkyl-linking group of about 1 to 10 carbons, preferably 1 to about 5 carbons, more preferably about 2 carbons.
• Y 2 is a combination of divalent heteroatom and divalent alkyl group.
• Each of the R groups in the general monomer structure (I) is a monovalent alkyl-linking group, preferably a methyl group.
• R 1 to R 7 can also be selected from -Y 2 -Si(R 8 R 9 R 10 ) and A.
• Another embodiment of the present invention is directed to a process for producing the described carbosiloxane monomers comprising chemically reacting a carbosiloxane compound with SiH functionality having the general formula shown below
• R 1 R 2 R 3 Si -Y 1 - [Si(R 4 R 5 )(Y 2 )] a - Si(R 6 R 7 ) - H (IV) wherein a is 0 to 100; Y 1 is a substituted or unsubstituted divalent alkyl linking group of 1 to 10 carbon atoms, and Y 2 can be Y 1 or a divalent hetero atom.
• R to R 7 is independently selected from the group consisting of monovalent aliphatic, cycloaliphatic or aromatic hydrocarbon groups of 1 to about 10 carbons and halogenated hydrocarbon groups of 1 to about 10 carbons.
• R 1 -R 7 can be - Y -Si(R 8 R 9 R 10 ) and A, wherein R 8 to R 10 is independently selected from the group consisting of monovalent aliphatic, cycloaliphatic or aromatic hydrocarbon groups of 1 to about 10 carbons and halogenated hydrocarbon groups of 1 to about 10 carbons.
• A can be a monovalent hydrophilic or hydrophobic moiety selected from the group consisting of, substituted or unsubstituted, saturated and unsaturated aliphatic, cycloaliphatic or aromatic hydrocarbons and optionally contains hetero atoms.
• R 15 is a linear or branched unsaturated alkyl group having about 0 to about 20 carbon atoms
• B is divalent moiety selected from the group consisting of substituted or unsubstituted, saturated and unsaturated aliphatic, cycloaliphatic or aromatic hydrocarbons and substituted or unsubstituted, saturated and unsaturated aliphatic, cycloaliphatic or aromatic hydrocarbons containing hetero atoms;
• B comprises functionalities such as alcohols, ethers, esters, amides, amines, acids and its salts, cyano, thio, urethane, urea, sulfonates, sulphonamides, phosphates and their combinations.
• M can be hydroxyl or halogen or epoxy or carboxylic acid group.
• G can be a halogen or hydroxyl or alkyloxy having 1 to 10 carbon atoms.
• R 12 to R can be selected from hydrogen or a substituted or unsubstituted saturated monovalent hydrocarbon group of 1 to about 20 carbons to produce said silicone monomer.
• the reaction of the functionalized carbosiloxane with alkylacryloyi compound having the general formula (VI) can be carried out in the presence of a tertiary amine base or basic ion-exchange resin (IER) or azeotrope forming solvent or reactant.
• the azeotrope forming solvent can be selected from hexane, heptane, toluene etc. and the reactant such as methylmethacrylate under the inert reaction conditions.
• compositions of the present invention can be mixed with other monomers or polymers that are the same or different to produce the compositions of the present invention. These compositions have been found to have properties that are favorable for use in the cosmetic and medical industries. Some examples and discussions of the different uses for the compositions are provided herein below.
• the silicone hydrogel copolymers are gaining importance in the health care industry for various applications such as contact lens, wound management and drug delivery applications because of their improved oxygen permeability compared to conventional hydrogels.
• One of the key challenges in health care is that the material used for these applications should be dimensionally and chemically stable and should not undergo hydrolytic degradation and leach out degradation products under the conditions of use, such as sterilization, storage in aqueous media containing buffers, etc.
• the carbosiloxane monomer of the instant invention shows improved hydrolytic stability over the conventional siloxane monomer, which enables it to produce silicone hydrogel copolymers with improved hydrolytic stability for health-care related applications, further details of which are shown in the following paragraphs. Also, its mono-functional polymerizable group (mono-acrylate or mono-methacrylate functionality)affords better control to produce silicone hydrogel copolymers with desired modulus depending upon the end applications.
• A. Contact lens A. A. Contact lens:
• the advantages of using the mono-functional carbosiloxane monomer of the instant invention for contact lens application are numerous.
• (1 ) the presence of carbosiloxane linkage, -Si-(CH 2 ) n -Si-, in the siloxane monomer composition of the present invention can help to produce soft hydrogel contact lens materials with improved hydrolytic stability. That means the silicone hydrogel contact lenses produced are hydrolytically stable and will not change in their chemical composition and physical dimensions when they are subjected to usage conditions, for e.g., in the eye or in the disinfecting solution or during sterilization.
• the contact lens material of the instant invention is also resilient.
• the monomers of the instant invention are compatible with hydrogel co-monomers in the entire range of compositions without employing any solvent or compatibilizing agents.
• the copolymer films obtained with various hydrogel comonomers and the mixtures thereof are transparent, water absorbing with inherently wettable surface.
• the human cornea requires about 2 ⁇ 10 '6 cm 3 /(sec. cm 2 atm.) of oxygen through the contact lens for better eye health as reported by Hill and Fatt (American Journal of Optometry and Archives of the American Academy of Optometry, Vol. 47, p. 50, 1970).
• the silicone-hydrogel contact lens materials made from the monomer of the instant invention allows better transmission of oxygen through itself to supply the necessary oxygen requirements of the human cornea.
• the monomer of the instant invention can be used to produce hydrogel copolymer with the desired lower modulus to improve the comfort of the lens wearers.
• the contact lens material can be produced with the monomer of the present instant invention employing the cure techniques (for eg. thermal and actinic radiation cure methods) known in the art with out employing solvent or compatibilizing agents.
• Hydrogels with high water content and oxygen permeability are needed to produce the wound-management devices (for eg. transdermal patches, wound healing patches, wound dressing patches etc).
• the water present in the wound-dressing material helps to provide a moist environment for better comfort and painless wound management.
• Oxygen also plays an important role in wound healing and the lack of oxygen transport in the wound dressing material has been identified as one of the most common issues affecting the wound healing process (Bok Y. Lee "The Wound Management Manual", McGraw-Hill, New York,2005, p.44). Oxygen transport to the wound through hemoglobin is an important process for wound healing. However, the damaged tissue in the wound can act as a barrier to hemoglobin leading to localized hypoxia at the wound site.
• Damaged tissue is generally hypoxic due to the large consumption of oxygen by cells.
• Leukocytes consume oxygen to produce infection-fighting oxidants.
• fibroblasts and endothelial cells also require oxygen for wound healing. Therefore, the only way of oxygen transport to the exterior part of the wound is from the atmosphere and this requires the wound dressing to have good oxygen permeability for better healing of the wounds.
• the monomer of the instant invention having hydrophilic moieties such as polyethers or other hydrophilic moieties can provide silicone hydrogels that are not only hydrolytically stable, but also water absorbing and highly oxygen permeable making them a suitable wound dressing material for various wound management applications. Hydrophilic silicone compositions of the present invention can also provide an excellent moist environment for better comfort and painless wound management.
• the silicone composition of current invention can be used as a potential carrier or device for various active ingredients and controlled release of those actives under different conditions (for example, pH, pressure, temperature, chemical reaction etc).
• biocompatible hydrogels are used as colon-specific drug delivery systems for the treatment of helicobacter pylori infection in peptic ulcer disease. These biocompatible hydrogels are designed to be highly swollen and to degrade in the presence of colonic enzymes or micro flora, providing colon-specific drug delivery. Additionally, biocompatible hydrogels protect insulin in the harsh, acidic environment of the stomach before releasing the drug in the small intestine.
• the hydrophilic silicone compositions of the present invention can be used to produce biocompatible silicone hydrogel-based drug delivery devices to release the drug locally to specific sites in the Gl tract.
• the hydrophilic silicone compositions of this invention can also be used for other biocompatible drug delivery applications such as puncta plugs, ophtha coils, retinal implants, transdermal patches, wound healing patches, transdermal iontophoresis etc.
• the silicone compositions of the present invention can be used for the transdermal drug delivery applications.
• Drug delivery to the skin has been generally used to treat skin diseases or for disinfections of the skin.
• transdermal route for the delivery of drugs has been investigated. Swollen soft hydrogels are explored to deliver the drugs for long period of duration and these hydrogels can be easily removed from the skin without pain and improves comfort for the patients.
• Current research in this field is now focused on iontophoresis and electroporation.
• Hydrogel-based formulations are being explored for electrically assisted delivery using transdermal iontophoresis for enhanced permeation of products such as, hormones and nicotine.
• the silicone compositions of the present invention can be used for the subcutaneous drug delivery applications also.
• the various possible therapeutic applications of hydrogels the most substantial application is implantable therapeutic devices.
• hydrogels can be used for delivery of proteins and peptides.
• implantable hydrogels are leading towards the development of biodegradable systems, which do not require surgical removal of the drug-loaded implants.
• Other health care applications include scaffolds for tissue engineering, anti-microbial devices, anti-bacterial devices, antifouling coatings, and anti-fungal devices.
• Pesticides Agriculture. Horticulture. Turf. Ornamental and Forestry:
• the silicone compositions of the present invention and its polymer can be used as a hydrolytically stable surfactant in pesticidal compositions at an amount sufficient to deliver between 0.005% and 2% to the final use concentration, either as a concentrate or diluted in a tank mix.
• the pesticidal composition may include excipients, cosurfactants, solvents, foam control agents, deposition aids, drift retardants, biologicals, micronutrients, fertilizers and the like.
• pesticide means any compound used to destroy pests, e.g., rodenticides, insecticides, miticides, fungicides, and herbicides.
• pesticides that can be employed include, but are not limited to, growth regulators, photosynthesis inhibitors, pigment inhibitors, mitotic disrupters, lipid biosynthesis inhibitors, cell wall inhibitors, and cell membrane disrupters.
• the amount of pesticide employed in compositions of the invention varies with the type of pesticide employed.
• Fungicide compositions that can be used with the present invention include, but are not limited to, aldimorph, tridemorph, dodemorph, dimethomorph; flusilazol, azaconazole, cyproconazole, epoxiconazole, furconazole, propiconazole, tebuconazole ' and the like; imazalil, thiophanate, benomyl carbendazim, chlorothialonil, dicloran, trifloxystrobin, fluoxystrobin, dimoxystrobin, azoxystrobin, furcaranil, prochloraz, flusulfamide, famoxadone, captan, maneb, mancozeb, dodicin, dodine, and metalaxyl.
• Insecticide, larvacide, miticide and ovacide compounds that can be used with the composition of the present invention, but not limited to, Bacillus thuringiensis, spinosad, abamectin, doramectin, lepimectin, pyrethrins, carbaryl, primicarb, aldicarb, methomyl, amitraz, boric acid, chlordimeform, novaluron, bistrifluron, triflumuron, diflubenzuron, imidacloprid, diazinon, acephate, endosulfan, kelevan, dimethoate, azinphos-ethyl, azinphos-methyl, izoxathion, chlorpyrifos, clofentezine, lambda-cyhalothrin, permethrin, bifenthrin, cypermethrin and the like.
• Fertilizers and micronutrients include, but not limited to, zinc sulfate, ferrous sulfate, ammonium sulfate, urea, urea ammonium nitrogen, ammonium thiosulfate, potassium sulfate, monoammonium phosphate, urea phosphate, calcium nitrate, boric acid, potassium and sodium salts of boric acid, phosphoric acid, magnesium hydroxide, manganese carbonate, calcium polysulfide, copper sulfate, manganese sulfate, iron sulfate, calcium sulfate, sodium molybdate, calcium chloride,
• the pesticide or fertilizer may be a liquid or a solid. If a solid, it is preferable that it is soluble in a solvent, or the organomodified siloxanes of the present invention, prior to application, and the silicone may act as a solvent, or surfactant for such solubility or additional surfactants may perform this function.
• coatings formulations will require a wetting agent or surfactant for the purpose of emulsification, compatibilization of components, leveling, flow and reduction of surface defects. Additionally, these additives may provide improvements in the cured or dry film, such as improved abrasion resistance, antiblocking, hydrophilic, and hydrophobic properties. Coatings formulations may exist as, foul-resistant coatings, biological coatings, seed coatings, solvent-borne coatings, water-borne coatings and powder coatings.
• the coatings components may be employed as: architecture coatings; OEM product coatings such as automotive coatings and coil coatings; Special Purpose coatings such as industrial maintenance coatings and marine coatings;
• Typical resin types include: Polyesters, alkyds, acrylics, epoxies and combinations thereof.
• the organomodified siloxane compositions of the present invention may be utilized in personal care emulsions, such as lotions, and creams.
• emulsions comprise at least two immiscible phases one of which is continuous and the other is discontinuous.
• emulsions may be liquids with varying viscosities or solids.
• the particle size of the emulsions may render them microemulsions or miniemulsions and, when the particle sizes are sufficiently small, these emulsions may be transparent. Further, it is also possible to prepare emulsions of emulsions and these are generally known as multiple emulsions.
• emulsions may be: 1 ) Aqueous emulsions, where the discontinuous phase comprises water and the continuous phase comprises the organomodified siloxane composition of the present invention. 2) Aqueous emulsions, where the discontinuous phase comprises the organomodified siloxane composition of the present invention and the continuous phase comprises water. 3) Non-aqueous emulsions, where the discontinuous phase comprises a non-aqueous hydroxylic solvent and the continuous phase comprises the organomodified siloxane composition of the present invention and 4) Non-aqueous emulsions, where the continuous phase comprises a nonaqueous hydroxylic organic solvent and the discontinuous phase comprises the organomodified siloxane composition of the present invention.
• the monomer of the instant invention can be polymerized using emulsion polymerization and the copolymer of these monomer obtained with acrylic comonomers forms excellent films which can be used for various skin care and hair care applications (for eg, mascara, styling gels, sun protection films etc).
• Suitable personal care compositions are made by combining, in a manner known in the art, for example, by mixing one or more of the above components with the organomodified siloxane composition of the present invention.
• Suitable personal care compositions may be in the form of a single phase or in the form of an emulsion, including oil-in-water, water-in-oil and anhydrous emulsions where the silicone phase may be either the discontinuous phase or the continuous phase, as well as multiple emulsions, such as, for example, oil-in water-in-oil emulsions and water-in-oil-in water-emulsions.
• the organomodified siloxane composition of the present invention and its polymers can be used as surfactants in home care applications, such as, laundry detergent and fabric softener, dishwashing liquids, wood and furniture polish, floor polish, tub and tile cleaners, toilet bowl cleaners, hard surface cleaners, window cleaners, antifog agents, drain cleaners, auto-dish washing detergents and sheeting agents, carpet cleaners, prewash spotters, rust cleaners and scale removers.
• home care applications such as, laundry detergent and fabric softener, dishwashing liquids, wood and furniture polish, floor polish, tub and tile cleaners, toilet bowl cleaners, hard surface cleaners, window cleaners, antifog agents, drain cleaners, auto-dish washing detergents and sheeting agents, carpet cleaners, prewash spotters, rust cleaners and scale removers.
• This monomer was prepared using two-step process. In the first step, a hydrosilylation reaction occurs between hydroxyl terminated methallyl polyether and mono-hydride functional carbosiloxane. In the second step, the hydroxyl group is converted into polymerizable methacrylate group through a methacrylation reaction.
• the mono-hydride functional carbosiloxane was prepared using the process disclosed in US 7,259,220 B1 , which is herein incorporated in its entirety by reference.
• the solvent was removed with a rotary vacuum evaporator and the final monomer was obtained as colorless to pale yellow, transparent liquid.
• the low boiling point of the solvent used enables the solvent to be removed completely at a temperature of about 30°C to 40°C under vacuum (i.e. less than about 10 mm Hg).
• the resulting monomer was well characterized by infrared spectroscopy, multinuclear NMR spectroscopy.
• This monomer was prepared was also prepared using two-step process. In the first step, a hydrosilylation reaction occurs between hydride functional carbosiloxane and vinyl functional cyclohexene epoxide. In the second step, the epoxide group is reacted with unsaturated acids to introduce polymerizable group in it.
• epoxy functional carbosiloxane was obtained as colorless, transparent liquid in quantitative yield without any undesired side products.
• the resultant pure product was well characterized by proton NMR spectroscopy.
• the epoxy functional carbosiloxane of the present invention can occur with or without solvent. If solvents are used, preferred ones include toluene, isopropylalcohol or methyl ethyl ketone.
• Example 1 The compound obtained in Example 1 (49 parts by weight), 2- hydroxy ethyl methacrylate (49 parts by weight), ethylene glycol dimethacrylate (EGDMA) (1 part by weight), and benzoyl peroxide (1 part by weight) were mixed and stirred.
• the resulting clear, homogeneous and transparent reaction mixture was purged with nitrogen gas and poured into a stainless steel mould.
• the thin film of the reaction mixture was thermally cured at 85°C for 8 hours using hot air oven.
• the silicone hydrogel film thus produced was transparent and water absorbing.
• Example 2 A silicone-hydrogel film was obtained in the same way as in Example 3 except that the compound obtained in Example 2 was used instead of compound obtained in Example 1.
• the silicone hydrogel film thus produced was transparent and water absorbing. Comparative Example 1 (CEx. 1)
• the monomer was prepared in the same way as in Example 1 except that 1 ,1 ,1 ,3,5,5,5-heptamethyltrisiloxane was used instead of 1-(2- trimethylsilylethyl)-1 ,1 ,3,3-tetramethyldisiloxane.
• the mono-acrylated siloxane monomer produced was well characterized by infrared spectroscopy, multinuclear NMR spectroscopy.
• Example 1 Hydrolytic stability of the monomer of the present invention was measured using HPLC (US Pub. Pat Appl. 20100069279). 0.5wt% of the monomers obtained in Example 1 (Ex.1 ) is introduced into three different vials containing 6.5, 7 and 7.5 pH solutions. The vials were sealed with leak proof seal and heated to 85 deg C. The heat accelerated hydrolytic degradation composition changes were monitored using HPLC as a function of time.
• the monomer of the current invention (Ex.1 ) showed improved hydrolytic stability under acidic, basic and neutral conditions in comparison to the conventional siloxane monomer (CEx.1 ) over the acidic, neutral and basic pH conditions ( Figure 1 ).
• Figure 1 show a hydrolytic stability data obtained for monomers produced in Ex.1 and CEx.2 at 85°C under different pH conditions; (A) pH 6.5, (B) pH 7.0 and (C) pH 7.5.
• the monomer of the current invention (Ex.1 ) showed improved hydrolytic stability under acidic, basic and neutral conditions in comparison to the conventional siloxane monomer (CEx.2) over the acidic, neutral and basic pH conditions ( Figure 1 ).

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