WO2014123959A1 - Lentille de contact hydratée perméable à l'oxygène et composition associée - Google Patents

Lentille de contact hydratée perméable à l'oxygène et composition associée Download PDF

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Publication number
WO2014123959A1
WO2014123959A1 PCT/US2014/014800 US2014014800W WO2014123959A1 WO 2014123959 A1 WO2014123959 A1 WO 2014123959A1 US 2014014800 W US2014014800 W US 2014014800W WO 2014123959 A1 WO2014123959 A1 WO 2014123959A1
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Prior art keywords
group
monomer
meth
acrylate
silicon
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PCT/US2014/014800
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English (en)
Inventor
Kunio JONIN
Takeshi Arakawa
Takao Sato
Vikram Kumar
John Nicholson
Ping Jiang
Eric Pohl
Kendall GUYER
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Seed Co., Ltd.
Momentive Performance Materials Inc.
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Application filed by Seed Co., Ltd., Momentive Performance Materials Inc. filed Critical Seed Co., Ltd.
Publication of WO2014123959A1 publication Critical patent/WO2014123959A1/fr

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    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses
    • G02B1/043—Contact lenses
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F226/00—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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F226/06—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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
    • C08F226/08—N-Vinyl-pyrrolidine
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/068—Polysiloxanes

Definitions

  • the present invention relates to a composition and an oxygen permeable hydrous contact lens made therefrom. More particularly, the present invention relates to a composition for an oxygen permeable hydrous contact lens comprising a monomer intramolecularly having silicon-containing moieties, at least one hydrophilic group, a cyclic hydrocarbon group, and an acryloyloxy or methacryloyloxy group; a hydrophilic monomer; and a second silicon-containing monomer, as well as to an oxygen permeable hydrous contact lens obtained from the composition .
  • HCL hard contact lens
  • SCL soft contact lens
  • the SCL has high flexibility and is superior in wear comfort, but has the problem that the oxygen permeability is low, which results in oxygen deficiency of the cornea when worn for a long time .
  • SHGCL (hereinafter, referred to as "SHGCL") comprising as a
  • the SHGCL is obtained by mixing a hydrophilic monomer with a hydrophobic silicone-containing monomer followed by copolymerizing them. Since the monomers are low in compatibility, however, it was difficult to prepare a homogeneous solution and to give transparency to the SHGCL formed .
  • Japanese Unexamined Patent Application Publication KOKAI Hll-228644 disclosed a method for enhancing the compatibility of the hydrophilic monomer with the
  • silicone-containing monomer by using an organic solvent, such as alcohols and ketones, as an amphiphatic substance.
  • organic solvent such as alcohols and ketones
  • Publication KOHYO 2005-518826 disclosed a method for improving the compatibility of the hydrophilic monomer with the
  • Japanese Unexamined Patent Application Publication KOKAI 2009-14977 disclosed a method for using a vinyl monomer as a compatibilizing agent for the polymerizable silicone compound and the hydrophilic.
  • Reference 1 Japanese Unexamined Patent Application Publication KOKAI Hll-228644 is hereinafter, referred to as "Reference 1".
  • Patent Reference 2 by incorporating as the constituent component the polymerizable silicone compound intramolecularly having a hydroxyl group, the compatibility between the silicone-containing monomer and the hydrophilic monomer has been improved and thus a transparent mixed solution and polymer are obtained.
  • silicone moieties are oriented on the surface of the polymer and the wettability of the polymer surface decreases .
  • the polymer obtained has a high degree of polymerization and strength, because the copolymerizable compounds are used as the compatibilizing agent.
  • the glass transition temperature of the polymer there are problems in that the glass transition temperature of the polymer
  • the polymers obtained by employing the methods disclosed in Patent References 2 and 3 are not suitable for contact lenses because these polymers have problems that the repellency of the polymer surface is strong and lipids in tear fluids adhere easily to them due to a hydrophobic interaction.
  • an operation for modifying the surface of the polymer is complicated and has a problem that the polymer itself can degrade .
  • one embodiment of the present invention to provide a composition capable of producing a polymer, which is suitable for the oxygen permeable hydrous contact lens . More particularly, the embodiment of the present invention is to provide a composition for producing a polymer suitable for the oxygen permeable hydrous contact lens by subjecting the composition to a copolymerization reaction, the composition being capable of avoiding in the copolymerization reaction the use of organic solvents that may decrease the strength of the polymer obtained and being capable of avoiding modification of the polymer surface after the copolymerization reaction.
  • Another embodiment of the present invention to provide an oxygen permeable hydrous contact lens obtained by using such composition.
  • the present invention provides for a polymer suitable for the oxygen permeable hydrous contact lens and constituent components of the polymer.
  • the composition of the present invention which comprises a monomer intramolecularly having a silicon-containing moiety, at least one hydrophilic group, a cyclic hydrocarbon group that has a more bulky structure than the silicon-containing moiety and an acryloyloxy or
  • the present inventors have found that by using a composition comprising (i) a monomer intramolecularly having silicon-containing moiety, at least one hydrophilic group, a cyclic hydrocarbon group, and an acryloyloxy or methacryloyloxy group, (ii) a hydrophilic monomer, and (iii) a second silicon-containing monomer, a polymer suitable for the oxygen permeable hydrous contact lens can be obtained, while avoiding the use of the organic solvents in the copolymerization reaction, and avoiding the modification of the surface of the polymer obtained.
  • the present invention has been completed based on such findings .
  • composition for the oxygen permeable hydrous contact lens which comprises:
  • Ri represents an acryloyloxy or methacryloyloxy group
  • R 2 represents a cyclic hydrocarbon group having a 4- to 8-membered ring
  • R 3 represents a hydrophilic group, or a straight or branched Ci_ 4 alkyl group substituted by one or more
  • R 4 represents a silicon-containing group
  • e 1 or 2;
  • the Ri is an acryloyloxy group.
  • the R 4 is a silicon-containing group
  • each R 5 , R 6 and R 7 is independently selected from the group consisting of -CH 3 , -C 2 H 5 , -OSiR 8 RgRi o and
  • f is an integer of from 0 to 3, and preferably
  • n is an integer of from 1 to 10, preferably of from 2 to 5.
  • the mixing ratio of the monomer represented by the general Formula (I) is 5% by weight to 70% by weight, based upon the total weight of radical-polymerizable monomer components .
  • an oxygen permeable hydrous contact lens obtained by copolymerizing the composition of the present invention and a process of manufacturing the contact lens .
  • composition of the present invention a polymer having the strength and surface wettability suitable for the oxygen permeable hydrous contact lens can be obtained because the use of the organic solvents in the
  • composition of the present invention comprises (i) a monomer intramolecularly having a silicon-containing
  • the polymer obtained by subjecting the composition of the present invention to the copolymerization reaction has transparency suitable for the contact lens .
  • the monomer intramolecularly having a silicon- containing moiety, at least one hydrophilic group, a cyclic hydrocarbon group and an acryloyloxy or methacryloyloxy group, which is a component contained in the composition of the present invention is exhibited more dominantly on the polymer surface after copolymerization than the silicon-containing monomer because the hydrophilic groups are introduced onto a bulky ring structure.
  • the hydrophilic groups are introduced onto a bulky ring structure.
  • the polymer obtained from the composition of the present invention is available as the oxygen permeable hydrous contact lens.
  • the oxygen permeable hydrous contact lens of the present invention obtained from the composition of the present invention has superior transparency, strength and surface wettability to those of the prior contact lenses.
  • the curable composition of the present invention comprises (i) a monomer intramolecularly having a silicon- containing moiety, at least one hydrophilic group, a cyclic hydrocarbon group and an acryloyloxy or methacryloyloxy group; (ii) a hydrophilic monomer; and(iii) a second silicon- containing monomer .
  • the monomer intramolecularly having a silicon-containing moiety, a hydrophilic group, a cyclic hydrocarbon group and an acryloyloxy or methacryloyloxy group is a monomer represented by the following general Formula (I),
  • Ri represents an acryloyloxy or methacryloyloxy group
  • R 2 represents a cyclic hydrocarbon group having a 4- to 8-membered ring
  • R 3 represents a hydrophilic group, or a straight or branched Ci_ 4 alkyl group substituted by one or more
  • R 4 represents a silicon-containing group
  • e 1 or 2.
  • Ri is an acryloyloxy group or a methacryloyloxy group, and is
  • the acryloyloxy group has the synonym names acryloxy and acrylate .
  • Methacryloyloxy group has the synonym names methacryloxy and methacrylate.
  • R 2 and R 3 together form a hydrophilic and cyclic hydrocarbon group, whereby the monomer represented by the general Formula (I) is the monomer having the hydrophilic and cyclic hydrocarbon group in which the R 3 is chemically bonded to the R 2 in the molecule.
  • R 2 is a cyclic hydrocarbon moiety
  • R 3 is a hydrophilic moiety.
  • R 2 which is the cyclic hydrocarbon moiety, has a more bulky structure than R , which is the silicon-containing group.
  • bulky structure means an organic group, when bonded to an acrylate to form an ester, occupies a molar volume equal to or greater than the molar volume of cyclobutyl acrylate at 25°C and 1.03 kilogram force/centimetre 2 (one atmosphere) of pressure.
  • the hydrophilic group which is R 3
  • R 2 is positioned on the surface of the polymer, thereby contributing to the wettability of the surface and making the polymer suitable for use in contact lens.
  • R 2 may be a group having a bulky structure such as a cyclic hydrocarbon group, wherein the ring is not less than a 4-membered ring.
  • R 2 is preferably not more than an 8-membered ring.
  • R 2 is preferably a 6- membered saturated cyclic hydrocarbon or a 6-membered
  • the wettability on the surface of the lens is affected by the number and structure of the hydrophilic group, which is R3 in the general Formula (I) .
  • the number of the hydrophilic groups is not particularly limited as long as it is 1 or more. When the number is 3 or more, however, the compatibility of the monomer of the general Formula (I) with the hydrophilic monomer may increase but the compatibility with the second silicon-containing monomer may decrease.
  • preferable number of the hydrophilic groups is 1 or 2.
  • the structure of R 3 which is a hydrophilic moiety is either the structure consisting of the hydrophilic group, or a straight or branched alkyl group having 1 to 4 carbons and substituted by one or more
  • R 3 is a straight or branched Ci ⁇ 4 alkyl group substituted by one or more hydrophilic groups, the hydrophilicity decreases with an increase in the number of carbons, and both the compatibility thereof with the
  • the preferable carbon number is 1 or 2, and as more preferable embodiments -CH 2 OH and
  • the hydrophilic group in R 3 is not particularly limited, but includes, for example, a hydroxyl group, a carboxyl group, an amino group and the like, and is preferably a hydroxyl group or an amino group having the structure, -NH 2 .
  • R in the general Formula (I) is not particularly limited as long as it is a silicon-containing group, but has
  • R 4 includes a silicon-containing group represented by the following general Formula (II),
  • R 8 , Rg and Ri o are each an independent group and represent -CH 3 or -C 2 H 5 , f is an integer of from 0 3, and preferably 2, and n is an integer of from 1 to 10, preferably 2 to 5.
  • a preferable embodiment of the monomer represented by the general Formula (I) is not particularly limited, but includes compounds of the following Formulae (III) and (IV)
  • ( trimethylsiloxy) methylsilanyl-ethyl group is trans-1,3- substitution of the cyclohexyl group.
  • the trans-1 , 3-substitution of the cyclohexyl group is believed to introduce more randomness (entropy) into the polymer containing the monomer of the present invention, thereby introducing a large free volume and better oxygen permeability.
  • ( hydroxycyclohexyl ) ethyl group include acrylic acid 2-hydroxy- 5- [ 2-bis- ( trimethylsiloxy ) methylsilanyl-ethyl ] -cyclohexyl ester, methacrylic acid 2-hydroxy-5- [ 2-bis- ( trimethylsiloxy) methylsilanyl-ethyl] -cyclohexyl ester, acrylic acid 2-hydroxy-3- [ 2-bis-
  • the representative and non-limiting examples of the trisiloxanes containing a 3- (meth) acryloxy-substituted ( hydroxycyclohexyl ) ethyl group include acrylic acid trans-2- hydroxy-trans-5- [2-bis- (trimethylsiloxy) methylsilanyl-ethyl ] - cyclohexyl ester, methacrylic acid trans-2-hydroxy-trans-5- [ 2- bis- (trimethylsiloxy) methylsilanyl-ethyl] -cyclohexyl ester, acrylic acid trans-2-hydroxy-trans-3- [2-bis- (trimethylsiloxy) - methylsilanyl-ethyl ] -cyclohexyl ester, and methacrylic acid trans-2-hydroxy-trans-3- [2-bis- (trimethylsiloxy) methylsilanyl- ethyl ] -cyclohexyl ester, and mixtures thereof. More
  • ( hydroxycyclohexyl ) ethyl group include acrylic acid trans-2- hydroxy-trans-5- [2-bis- (trimethylsiloxy) methylsilanyl-ethyl ] - cyclohexyl ester and methacrylic acid trans-2-hydroxy-trans-5- [2-bis- (trimethylsiloxy) -methylsilanyl-ethyl] -cyclohexyl ester with the structure with the stereochemistry of Formula (V) :
  • the carbon atom on the ring to which the (meth) acryloxy group is bonded is assigned the 1-position (C-l) on the ring.
  • the (meth) acryloxy group is bonded to the C-l carbon in an axial position of the cyclohexane ring.
  • the hydroxyl group occupies the axial position on C-2 carbon atom of the cyclohexane ring.
  • the stereochemistry of the hydroxyl group is trans relative to the (meth) acryloxy group.
  • composition is a mixture of isomers.
  • the composition of acrylic acid trans-2-hydroxy-trans-5- [2- bis- (trimethylsiloxy) methylsilanyl-ethyl] -cyclohexyl ester is preferably greater than 85 weight percent, more preferably greater than 95 weight percent, based upon the total weight of the acrylic acid trans-2-hydroxy-trans-5- [ 2-bis- ( trimethylsiloxy) methylsilanyl-ethyl] -cyclohexyl ester and the acrylic acid trans-2-hydroxy-cis-4- [2-bis-
  • the composition of methacrylic acid trans-2-hydroxy-trans-5- [2- bis- (trimethylsiloxy) methylsilanyl-ethyl] -cyclohexyl ester is preferably greater than 85 weight percent, more preferably greater than 95 weight percent, based upon the total weight of the methacrylic acid trans-2-hydroxy-trans-5- [ 2-bis- ( trimethylsiloxy) methylsilanyl-ethyl] -cyclohexyl ester and the methacrylic acid trans-2-hydroxy-cis-4- [2-bis- ( trimethylsiloxy) methylsilanyl-ethyl] -cyclohexyl ester . [0035]
  • the trisiloxanes containing a 3- (meth) acryloxy-substituted (hydroxycyclohexyl ) ethyl group composition comprises from 40 to 99 weight percent acrylic acid trans-2-hydroxy-trans-5- [2-bis-
  • the process for preparing trisiloxanes containing a 3- (meth) acryloxy-substituted (hydroxycyclohexyl ) ethyl group having the general Formulae (III) or (IV) comprises:
  • step (b) reacting the product of step (a) with (meth) acrylic acid to open the oxirane ring and provide for the trisiloxane containing a 3- (meth) acryloxy-substituted
  • a particularly preferred stereochemistry of the 3- ethenyl-7-oxa-bicyclo [ 4.1.0 ] heptane has the oxygen atom of the oxirane ring bonded to the 1- and 6-carbon atoms of the cyclohexyl group in the C-l eguatorial and C-6 axial
  • stereoisomers promote the axial attack of the (meth) acrylate nucleophile on the epoxy ring and thereby promote the 1 , 3-substitution of the cyclohexyl ring with the (meth) acryloxy group relative to the bis- ( trimethylsiloxy) methylsilanyl-ethyl group .
  • 3-ethenyl-7-oxa- bicyclo [ 4.1.0 ] heptane is made from the epoxidation of 4-vinyl- cyclohexene and 2-vinyl-cyclohexene, respectively.
  • the epoxidation of the more highly substituted carbon-carbon double bond can be achieved by treating alkene with peroxide- containing reagents, which donate a single oxygen atom.
  • Typical peroxide-containing reagents include hydrogen
  • the epoxidation agent is selected from the group consisting of perbenzoic acid, m-chloroperbenzoic acid, monoperphthalic acid and peracetic acid. These epoxdation agents allow for the isolation of the formed epoxide.
  • the reaction may be carried out in an organic solvent, such as chlorinated hydrocarbons, ethers or esters. Representative and non-limiting examples of the solvents include methylene chloride, chloroform, diethyl ether, tetrahydrofuran, and ethyl acetate .
  • the epoxidation reaction generates two stereoisomers of 3-ethenyl -7-oxa-bicyclo [ 4.1.0 ] heptane . It is preferred that the stereoisomers of 3-ethenyl-7-oxa-bicyclo [ 4.1.0 ] heptane be separated from each other prior to the reaction with the 1, 1, 1, 2, 3, 3, 3-heptamethyl-trisiloxane .
  • the stereoisomers can be separated by fraction distillation, preparative gas chromatography, preparative liguid chromatography or other methods commonly used in separating stereoisomers .
  • the stereoisomers are separated using fractional distillation of the mixture of stereoisomers at elevated temperatures and at subatmospheric, atmospheric or
  • stereoisomers are separated by fractional distillation using a rectification column having greater than 20 theoretical plates at atmospheric pressure and temperature ranging from 165° to 170°C .
  • the 3-ethenyl-7-oxa-bicyclo [ 4.1.0 ] heptane which has the oxygen atom of the oxirane ring bonded to the 1 and 6-carbon atoms of the cyclohexyl group in the C-l eguatorial and C-6 axial positions and has the vinyl group bonded to the 3-carbon atom of the cyclohexyl ring in the eguatorial position, is preferably greater than 85 weight percent, and more preferably greater than 95 weight percent, based upon the total weight of the two stereoisomers .
  • the 1 , 1 , 1 , 2 , 3 , 3 , 3-heptamethyl-trisiloxane may be prepared by a variety of methods, including hydrolysis and condensation of trimethylchlorosilane and methyldichlorosilane followed by separation of the product or eguilibration of
  • distillation Further purification, such as redistillation, is often used to prepare high purity 1,1,1,2,3,3,3- heptamethyl-trisiloxane (normal boiling point 142°C), free of higher molecular weight oligomers and hexamethyldisiloxane.
  • hydrosilylation reaction between 1,1,1,2,3,3,3- heptamethyl-trisiloxane and the ethenyl-oxa-bicyclo [ 4.1.0 ] heptane is conducted in the presence of a hydrosilylation catalyst, especially noble metal hydrosilylation catalysts.
  • the catalysts include platinum, palladium, ruthenium, iridium and rhodium as well as compounds containing these metals.
  • catalysts may be supported on activated carbon, aluminum oxide, ceramic materials and the like or in a colloidal suspension often formed in situ by the reduction of metal salts .
  • Homogeneous catalysts are preferred, including
  • chloroplatinic acid dissolved in ethanol, isopropanol or octanol and the platinum ( 0 ) -1 , 3-divinyl-l , 1, 3 , 3- tetramethyldisiloxane complex, known as Karstedt catalyst, dissolved in xylene or polydimethylsiloxane oils.
  • the catalyst is employed in a catalytic amount sufficient to induce and complete the hydrosilylation reaction.
  • the amount of catalyst is from 1 to 100 ppm metal catalysts based on the weight of the metal and the total weight of 1, 1, 1, 2, 3, 3, 3-heptamethyl-trisiloxane and the ethenyl-oxa-bicyclo [ 4.1.0 ] heptane.
  • the hydrosilylation reaction may be conducted in a continuous process or a batch process wherein the reactants are introduced into a reactor and the temperature of the mixture adjusted to within the range of from 0°C to 180° C, and more specifically from 20°C to 120° C. Upon addition of the catalyst, the reaction is usually exothermic, peaking at a temperature of from 75°C to 200°C.
  • the reaction can be conducted in an inert atmosphere such as nitrogen .
  • the mixing ratio of the monomer represented by the general Formula (I) is not particularly limited and may suitably vary according to types of the hydrophilic monomer and the silicon-containing monomer used concurrently.
  • the mixing ratio is preferably 5% by weight to 70% by weight, more preferably 10% by weight to 50% by weight, based upon the total weight of radical-polymerizable monomer
  • the radical-polymerizable monomer components are organic compounds having a group capable of reacting with a free-radical and at least one other radical- polymerizable monomer component to form an oligomeric or polymeric compound.
  • the group that is capable of reacting with a free-radical and at least one other radical- polymerizable monomer component is a carbon-carbon double bond, such as a vinyl group, an acryloyl group or a
  • the mixing ratio is less than 5% by weight, the hydrophilic monomer and the second silicon- containing monomer are not compatible and therefore there is a high possibility that the homogeneous solution is not obtained. Further, when the mixing ratio is beyond 70% by weight, the mixing ratio of the hydrophilic monomer decreases, the contact lens obtained does not have sufficient
  • composition of the present invention the composition of the present invention.
  • hydrophilic monomer is mixed as a constituent component in order to impart a desired water content ratio to the contact lens obtained.
  • the hydrophilic monomer is not particularly limited as long as it intramolecularly has at least one or more radical-polymerizable groups and hydrophilic groups respectively .
  • the hydrophilic monomer is an organic compound having the general Formula (VI) :
  • Ri i is a radical polymerizable group having the general
  • each R i is independently hydrogen, methyl or ethyl, A is a chemical bond, -0- or -NR 14 - and h is 0 or 1;
  • R 12 is a chemical bond or an organic group having from 1 to 30 carbon atoms and optionally an oxygen atom or a nitrogen atom;
  • g 1 or 2.
  • hydrophilic monomer examples include N, -dimethyl-acrylamide (DMAA), 2- hydroxyethyl methacrylate (HEMA), (meth) acrylic acid,
  • N-vinylpyrrolidone N-vinyl-N-methylacetamide, N-vinyl- N-ethylacetamide, N-vinyl-N-ethylformamide, N-vinylformamide and the like. These can be used alone or in combination with two or more thereof.
  • the mixing ratio of the hydrophilic monomer is the mixing ratio of the hydrophilic monomer.
  • the mixing ratio is less than 20% by weight, there is a possibility that sufficient flexibility and hydrous property cannot be imparted to the contact lens obtained.
  • the mixing ratio is beyond 70% by weight, the mixing ratio of the second silicon-containing monomer decreases and therefore there is a possibility that sufficient oxygen permeability cannot be imparted to the contact lens obtained.
  • the second silicon-containing monomer is mixed as a constituent component in order to impart preferred oxygen permeability to the contact lens obtained.
  • the silicon-containing monomer is not particularly limited as long as it intramolecularly has at least one or more radical-polymerizable groups and at least one or more silicon-containing group having at least one silicon-oxygen-silicon bond.
  • the second silicon-containing monomer is a radical-polymerizable compound having the general Formula (VIII) : 7
  • Ri5 is a hydrogen or methyl
  • Ai is a chemical bond, -0- or -NR 15 -;
  • Ri6 is a chemical bond or a divalent branched or straight chain alkylene group of from 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms;
  • Ri7 is hydrogen, an alkyl group of from 1 to 10 carbon atoms or a radical polymerizable group having the Formula
  • Ri 8 is hydrogen or methyl
  • a 2 is a chemical bond
  • Ri9 is a chemical bond or a divalent branched or straight chain alkylene group of from 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms and g is 0 or 1, with the proviso that if g is 1, then Ri 9 is not a chemical bond; i is 0 or 1, with the proviso that if i is 1, then R i6 is not a chemical bond; and
  • p is an integer from 2 to 150, preferably from 5 to 75 and more preferably form 10 to 40.
  • the second silicon-containing monomer include
  • the mixing ratio of the silicon-containing monomer is preferably 10% by weight to 60% by weight, more preferably 20% by weight to 50% by weight, based upon the total weight of radical-polymerizable monomer components.
  • the mixing ratio is less than 10% by weight, there is a possibility that sufficient oxygen permeability cannot be imparted to the contact lens obtained.
  • the mixing ratio is beyond 60% by weight, the mixing ratio of the hydrophilic monomer decreases and therefore there is a possibility that preferred flexibility cannot be imparted to the contact lens obtained .
  • Table 1 shows representative and non-limiting examples of the combination of (i) a monomer; (ii) a hydrophilic monomer; and (iii) a second silicon-containing monomer in accordance with the purpose of the present invention :
  • HEMA methacrylate
  • NDP N-(NVP) pyl ) polydimethy trans-2-hydroxy- lsiloxane
  • a cross-linker monomer having two or more radical-polymerizable functional groups can be mixed in order to control the mechanical strength and
  • the cross-linker monomer includes a (meth) acrylate-based cross- linker monomer.
  • Representative and non-limiting examples of cross-linker monomers include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, dipropylene glycol
  • tetra (meth) acrylate and dipentaerythritol hexa (meth) acrylate as well as a vinyl-based cross-linkable monomer such as allyl methacrylate, diallyl maleate, diallyl fumarate, diallyl succinate, diallyl phthalate, triallyl cyanurate, triallyl isocyanurate, diethylene glycol bisallylcarbonate , triallyl phosphate, triallyl trimellitate, diallyl ether, N,N- diallylmelamine and divinylbenzene ; and the like.
  • allyl methacrylate diallyl maleate, diallyl fumarate, diallyl succinate, diallyl phthalate, triallyl cyanurate, triallyl isocyanurate, diethylene glycol bisallylcarbonate , triallyl phosphate, triallyl trimellitate, diallyl ether, N,N- diallylmelamine and divinylbenzene ; and
  • the mixing ratio of the cross-linker monomer is the mixing ratio of the cross-linker monomer
  • 0.10% by weight to 5.0% by weight more preferably 0.20% by weight to 3.0% by weight, based upon the total weight of radical-polymerizable monomer components.
  • the mixing ratio is less than 0.10% by weight, there is a possibility that sufficient mechanical strength cannot be imparted to the contact lens obtained.
  • the mixing ratio is beyond 5.0% by weight, flexibility of the contact lens obtained can be impaired and therefore there is a possibility that wear comfort thereof can degrade .
  • composition of the present invention a
  • hydrophobic radical-polymerizable non-silicon-containing monomer for controlling physical properties can be mixed in order to control the physical properties including the mechanical strength, shape stability and flexibility that the obtained contact lens has .
  • the hydrophobic radical-polymerizable non-silicon-containing monomer includes a straight, branched or cyclic alkyl (meth) acrylate and fluorine-containing alkyl (meth) acrylate .
  • hydrophobic radical-polymerizable non-silicon-containing monomer examples include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, i-propyl (meth) acrylate, N-butyl (meth) acrylate, i-butyl (meth) acrylate, t-butyl
  • (meth) acrylate include trifluoroethyl (meth) acrylate, tetrafluoropropyl (meth) acrylate, tetrafluoropentyl
  • hydrophobic radical-polymerizable non- silicon-containing monomers can be used alone or in
  • trifluoroethyl (meth) acrylate, tetrafluoropropyl (meth) acrylate, tetrafluoropentyl (meth) acrylate are preferably used.
  • the mixing ratio of the hydrophobic radical- polymerizable non-silicon-containing monomer for controlling physical properties is preferably less than 20% by weight, based upon the total weight of the radical-polymerizable monomer components but is more preferably less than 15% by weight.
  • the mixing ratio is 20% or more by weight, the mixing ratios of the second silicon-containing monomer and the hydrophilic monomer are insufficient, and therefore there is a possibility that good oxygen permeability and hydrous property cannot be imparted to the contact lens obtained.
  • composition of the present invention When the composition of the present invention is subjected to the copolymerization reaction, a polymerization initiator is added to the composition of the present
  • the polymerization initiator includes an azo based-polymerization initiator.
  • polymerization initiators include 2,2'- azobis-isobutyronitrile, 1,1' -azobis ( cyclohexane-1- carbonitrile ) , 2 , 2 ' -azobis ( 2 , 4-dimetylvaleronitrile ) , 2,2'- azobis ( 2-methyl butyronitrile ) , 2 , 2 ' -azobis ( 4-methoxy-2 , 4- dimethyl-valeronitrile ) , 2, 2 ' -azobisisobutyric acid dimethyl ester and 2 , 2 ' -azobis ( 2 , 4 , 4-trimethylpentane ) as well as an organic peroxide based-polymerization initiator such as diisobutyrylperoxide, di ( 3 , 5 , 5-trimethylhexanoyl ) peroxide, dil
  • neodecanoate tertiary-butylperoxy-neodecanoate, tertiary hexyl peroxy pivarate and tertiarybutyl peroxy pivarate .
  • the polymerizable initiator is preferably an azo-based
  • the polymerization initiator 2,2'- azobis ( isobutylonitrile ) .
  • the mixing ratio of the polymerization initiator is preferably 0.001 parts by weight to 1.0 part by weight, more preferably 0.01 parts by weight to 1.0 part by weight relative to 100 parts by weight, wherein the 100 parts by weight is the total weight of radical- polymerizable monomer components.
  • an ultraviolet absorber can be added. Specifically, the
  • ultraviolet absorber includes 2-hydroxy-4-
  • the composition comprises:
  • Ri represents an acryloyloxy or methacryloyloxy group
  • R 2 represents a cyclic hydrocarbon group having a 4- to 8-membered ring
  • R 3 represents a hydrophilic group, or a straight or branched Ci_ 4 alkyl group substituted by one or more hydrophilic groups,
  • R 4 represents a silicon-containing group, and e is 1 or 2, wherein component (i) in the amount of from 5% by weight to 70% by weight, based upon the total weight of radical- polymerizable monomer components;
  • cross-linker monomer in the amount of from 0.1% by weight to 5% by weight, based upon the total weight of
  • composition comprises:
  • Ri represents an acryloyloxy or methacryloyloxy group
  • R 2 represents a cyclic hydrocarbon group having a 4- to
  • R 3 represents a hydrophilic group, or a straight or branched Ci_ 4 alkyl group substituted by one or more
  • R 4 represents a silicon-containing group, and e is 1 or
  • component (i) is in the amount of from 10% by weight to 50% by weight, based upon the total weight of radical-polymerizable monomer components;
  • cross-linker monomer in the amount of from 0.2% by weight to 3% by weight, based upon the total weight of radical-polymerizable monomer components.
  • radical-polymerizable monomer components preferably is the sum of the components (i), (ii), (iii) and, if present, cross-linker monomer and hydrophobic radical- polymerizable non-silicon-containing monomer.
  • composition of the present invention is suitable for the oxygen permeable hydrous contact lens.
  • reaction conditions such as the time and the temperature when copolymerizing the monomer components can be suitably determined by those skilled in the art depending on the type of polymerization initiator and others as index.
  • composition of the present invention is a
  • composition suitable for an oxygen permeable hydrous contact lens for example, including the following Embodiments (1) to (4) .
  • Embodiment ( 1 ) is a diagrammatic representation of Embodiment ( 1 ) of Embodiment ( 1 ) of Embodiment ( 1 ) :
  • a curable composition for an oxygen permeable hydrous contact lens which comprises:
  • Ri represents an acryloyloxy or methacryloyloxy group
  • R 2 represents a cyclic hydrocarbon group having a 4- to 8-membered ring
  • R 3 represents a hydrophilic group, or a straight or branched Ci_ 4 alkyl group substituted by one or more
  • R 4 represents a silicon-containing group
  • e 1 or 2;
  • Embodiment ( 2 ) is a diagrammatic representation of Embodiment ( 2 ) of Embodiment ( 2 ) of Embodiment ( 2 ) :
  • a cured composition obtained from a curable composition comprising
  • Ri represents an acryloyloxy or methacryloyloxy group
  • R 2 represents a cyclic hydrocarbon group having a 4- 8-membered ring
  • R 3 represents a hydrophilic group, or a straight or branched C i_ 4 alkyl group substituted by one or more
  • R 4 represents a silicon-containing group having the following general Formula (II),
  • each R 5 , R 6 and R 7 is independently selected from the group consisting of -CH 3 , -C 2 H 5 , -OSiR 8 RgRi o and
  • each R 8 , Rg and Ri o is independently -CH 3 or -C 2 H 5 , f is an integer of from 0 to 3 and n is an integer of from 1 to 10, and
  • e 1 or 2;
  • a second silicon-containing monomer optionally at least one additional component selected from the group consisting of a crosslinker monomer, a hydrophobic radical-polymerizable non-silicon-containing monomer, and a polymerization initiator, wherein said composition is
  • Embodiment ( 3 ) is a diagrammatic representation of Embodiment ( 3 ) of Embodiment ( 3 ) of Embodiment ( 3 ) :
  • a composition comprising the reaction product of a curable composition comprising
  • Ri represents an acryloyloxy or methacryloyloxy group
  • R 2 represents a cyclic hydrocarbon group having a 4- 8-membered ring
  • R 3 represents a hydrophilic group, or a straight or branched Ci_ 4 alkyl group substituted by one or more
  • R 4 represents a silicon-containing group having the following general Formula (II),
  • each R 5 , R 6 and R 7 is independently selected from the group consisting of -CH 3 , -C 2 H 5 , -OSiR 8 RgRi o and
  • f is an integer of from 0 to 3 and n is an integer of from 1 to 10, and
  • e 1 or 2;
  • a second silicon-containing monomer (iii) a second silicon-containing monomer; and optionally at least one additional component selected from the group consisting of a crosslinker monomer, a hydrophobic radical-polymerizable non-silicon-containing monomer, and a polymerization initiator.
  • Embodiment ( 4 )
  • a composition comprising the reaction product of a curable composition comprising
  • Ri represents an acryloyloxy or methacryloyloxy group
  • R 2 represents a cyclic hydrocarbon group having a 4- to 8-membered ring
  • R 3 represents a hydrop ilic group, or a straight or branched Ci_ 4 alkyl group substituted by one or more
  • R 4 represents a silicon-containing group having the following general Formula (II),
  • each R 5 , R 6 and R 7 is independently selected from the group consisting of -CH 3 , -C 2 H 5 , -OSiR 8 RgRio and
  • each R 8 , Rg and Rio is independently -CH 3 or -C 2 H 5
  • f is an integer of from 0 to 3
  • n is an integer of from 1 to 10
  • e 1 or 2;
  • a second silicon-containing monomer optionally at least one additional component selected from the group consisting of a crosslinker monomer, a hydrophobic radical-polymerizable non-silicon-containing monomer, and a polymerization initiator, wherein said reaction product is permeable to oxygen.
  • the oxygen permeable hydrous contact lens of the present invention is obtained by copolymerizing the composition of the present invention.
  • the process for producing the contact lens of the present invention there can be used known methods such as a method of executing the polymerization with a molding tool for the forming of the lens, and a method of executing the polymerization in a tubular vessel followed by cutting and polishing into the form of the lens.
  • the mixed solutions of monomers for producing contact lenses of Examples and Comparative Examples of the present invention were prepared at the mixing ratio shown in Table2. Each component was mixed in a test tube and after mixed homogeneously, was dispensed into a resin mold made of polypropylene, and heated at 80°C for 6 hours to obtain a contact lens. With ethanol, the obtained contact lens was washed to remove residual raw materials and was swelled, and then was replaced with phosphate buffer (pH 8.0).
  • phosphate buffer pH 8.0
  • Each raw monomer was sequentially weighed into a beaker, stirred at a room temperature for 30 minutes and left to stand. After confirmed by visual observation whether the mixed solution was homogeneous or not, light transmittance was measured with a spectrophotometer .
  • the light transmittance is not less than 90%.
  • the mixed solution is not homogeneous. Alternatively, the light transmittance is less than 90%.
  • the resulting contact lens was immersed in phosphate buffer (pH 8.0) at 37°C ⁇ 2°C for 24 hours and evaluated by visual observation for surface wettability thereof when removed from the phosphate buffer .
  • phosphate buffer pH 8.0
  • the transparency of the resulting contact lens was evaluated by measuring the light transmittance with a
  • the light transmittance is not less than 90% .
  • the light transmittance is less than 90% .
  • the oxygen permeability coefficient of the resulting contact lens was measured according to "Working Procedures for Measurement of Dk value by Improved Electrode Method"
  • an oxygen permeability coefficient is greater than 70 X 10 -11 (cm 2 /sec) ⁇ (ml 0 2 /ml X mmHg) , more preferably greater than 80 X 10 -11 (cm 2 /sec) ⁇ (ml 0 2 /ml X mmHg), and most preferably, greater than 90 X 10 -11 (cm 2 /sec) ⁇ (ml 0 2 /ml X mmHg).
  • the strength of the resulting contact lens was evaluated by breaking strength according to "Test Method for Tensile Properties of Plastics (JIS K7113)".
  • the hydrous property of the resulting contact lens was measured according to "Determination of Water Content of Hydrogel Lenses (ISO 10339:1997)”.
  • copolymerizing the solutions had good transparency, strength and surface wettability. Furthermore, oxygen permeability and hydrous property also were sufficient .
  • Comparative Example 1 the compatibilizing agent was not added. As a result, the homogeneous solution was not obtained and the contact lens was not produced.
  • the contact lens which is transparent and sufficient in strength, was obtained.
  • the surface wettability of the contact lens was low due to influence of the vinyl compound added.
  • FM-0711 monomethacryloxypoly (dimethylsiloxane ) (manufactured by CHISSO CORPORATION)
  • Tris [tris (trimethylsiloxy) silyl] propyl methacrylate
  • Tris-OH [tris (trimethylsiloxy) silyl] -1-hydroxypropyl methacrylate

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Abstract

Cette invention concerne une composition et une lentille de contact hydratée fabriquée à partir de celle-ci. Plus particulièrement, cette invention concerne une composition pour lentille de contact hydratée perméable à l'oxygène comprenant un monomère contenant dans sa molécule des fragments contenant du silicium, au moins un groupe hydrophile, un groupe hydrocarboné cyclique et un groupe acryloyloxy ou méthacryloyloxy ; un monomère hydrophile ; et un second monomère contenant du silicium, ainsi qu'une lentille de contact hydratée perméable à l'oxygène obtenue à partir de ladite composition.
PCT/US2014/014800 2013-02-06 2014-02-05 Lentille de contact hydratée perméable à l'oxygène et composition associée WO2014123959A1 (fr)

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WO2018009309A1 (fr) 2016-07-06 2018-01-11 Johnson & Johnson Vision Care, Inc. Optique centrale à rigidité augmenté dans des lentilles de contact souples pour correction d'astigmatisme
WO2018009312A1 (fr) 2016-07-06 2018-01-11 Johnson & Johnson Vision Care, Inc. Hydrogels de silicone comprenant des n-alkyl-méthacrylamides et lentilles de contact fabriquées à partir de ceux-ci
WO2018067284A1 (fr) 2016-10-06 2018-04-12 Johnson & Johnson Vision Care, Inc. Prépolymères triblocs et leur utilisation dans des hydrogels de silicone
US10209534B2 (en) 2012-03-27 2019-02-19 Johnson & Johnson Vision Care, Inc. Increased stiffness center optic in soft contact lenses for astigmatism correction
US10996491B2 (en) 2018-03-23 2021-05-04 Johnson & Johnson Vision Care, Inc. Ink composition for cosmetic contact lenses
CN113248719A (zh) * 2021-04-19 2021-08-13 江苏海伦隐形眼镜有限公司 单封端有机硅氧烷齐聚物、硅水凝胶、角膜接触镜及制备方法
WO2022079630A1 (fr) 2020-10-13 2022-04-21 Johnson & Johnson Vision Care, Inc. Commande de position et de rotation de lentille de contact à l'aide de la pression du bord de la paupière
US11891526B2 (en) 2019-09-12 2024-02-06 Johnson & Johnson Vision Care, Inc. Ink composition for cosmetic contact lenses

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US11187920B2 (en) 2012-03-27 2021-11-30 Johnson & Johnson Vision Care, Inc. Increased stiffness center optic in soft contact lenses for astigmatism correction
US10620456B2 (en) 2012-03-27 2020-04-14 Johnson & Johnson Vision Care, Inc. Increased stiffness center optic in soft contact lenses for astigmatism correction
US11829008B2 (en) 2012-03-27 2023-11-28 Johnson & Johnson Vision Care, Inc. Increased stiffness center optic in soft contact lenses for astigmatism correction
US10209534B2 (en) 2012-03-27 2019-02-19 Johnson & Johnson Vision Care, Inc. Increased stiffness center optic in soft contact lenses for astigmatism correction
US11125916B2 (en) 2016-07-06 2021-09-21 Johnson & Johnson Vision Care, Inc. Silicone hydrogels comprising N-alkyl methacrylamides and contact lenses made thereof
WO2018009312A1 (fr) 2016-07-06 2018-01-11 Johnson & Johnson Vision Care, Inc. Hydrogels de silicone comprenant des n-alkyl-méthacrylamides et lentilles de contact fabriquées à partir de ceux-ci
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EP4043508A1 (fr) 2016-07-06 2022-08-17 Johnson & Johnson Vision Care, Inc. Hydrogels de silicone comprenant des n-alkyl-méthacrylamides et lentilles de contact fabriquées à partir de ceux-ci
US11754754B2 (en) 2016-07-06 2023-09-12 Johnson & Johnson Vision Care, Inc. Silicone hydrogels comprising N-alkyl methacrylamides and contact lenses made thereof
US10676575B2 (en) 2016-10-06 2020-06-09 Johnson & Johnson Vision Care, Inc. Tri-block prepolymers and their use in silicone hydrogels
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US10996491B2 (en) 2018-03-23 2021-05-04 Johnson & Johnson Vision Care, Inc. Ink composition for cosmetic contact lenses
US11891526B2 (en) 2019-09-12 2024-02-06 Johnson & Johnson Vision Care, Inc. Ink composition for cosmetic contact lenses
WO2022079630A1 (fr) 2020-10-13 2022-04-21 Johnson & Johnson Vision Care, Inc. Commande de position et de rotation de lentille de contact à l'aide de la pression du bord de la paupière
CN113248719A (zh) * 2021-04-19 2021-08-13 江苏海伦隐形眼镜有限公司 单封端有机硅氧烷齐聚物、硅水凝胶、角膜接触镜及制备方法

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