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EP0294976A2 Expired / Lapsed EP ⏱️ 0.0 years remaining

Non-hydrous soft contact lens and process for producing the same

Assignee: Novartis AG
•
Filing: 1988-05-27
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Granted: —
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Expires: 2008-05-27
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Abstract

Abstract A non-hydrous soft contact lens comprising a copolymer comprising, as monomer units,: (a) from 33.9 to 89 mol % of an acrylate represented by the general formula (I) shown below; (b) from 4.9 to 65 mol % of a methacrylate represented by the general formula (II) shown below; (c) from 1 to 20 mol % of at least one selected from an unsaturated carboxylic acid and its particular esters; (d) from 0 to 20 mol % of a particular acrylic acid ester having a straight chain alkyl or fluoroalkyl group; (e) from 0 to 20 mol % of a methacrylic acid ester having a straight-chain alkyl group; (f) from 0.1 to 10 mol % of a crosslinking monomer. General formula (I): wherein R₁ is a particular straight-chain alkyl or fluoroalkyl group. General formula (II): wherein R₂ is a particular straight-chain fluoroalkyl group; and a process for preparing the same. This contact lens has good oxygen permeability, mechanical strength, etc.

Inventors

  • 👤 Tetsuo Itoh
  • 👤 Noboru& Room 101&Appartement No1-2-29 Satoh
  • 👤 Kazuhiko Takahashi
  • 👤 Taro Suminoe
  • 👤 Takao Shimizu

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-09 04:07
CPC Classifications
G; G02; G02B; G02B1/00; G02B1/04; G02B1/041; G02B1/043; C; C08; C08F; C08F220/00; C08F220/02; C08F220/10; C08F220/22

Claims Analysis

Total Claims: 27
Claim 1
Independent Claim 509 words
A non-hydrous soft contact lens comprising a copolymer comprising, as monomer units,: (a) from 33.9 to 89 mol % of an acrylate represented by the general formula (I) shown below; (b) from 4.9 to 65 mol % of a methacrylate represented by the general formula (II) shown below; (c) from 1 to 20 mol % of at least one monomer selected from the group consisting of an unsaturated carboxylic acid, an unsaturated carboxylic acid anhydride an unsaturated carboxylic acid alkyl ester having a branched or cyclic alkyl group which may have a substituent, and an unsaturated carboxylic acid fluoroalkyl ester having a branched or cyclic fluoroalkyl group which may have a substituent; (d) from 0 to 20 mol % of at least one monomer selected from the group consisting of an acrylic acid lower alkyl ester having a straight-chain alkyl group containing 1 to 3 carbon atoms, and an acrylic acid lower fluoroalkyl ester having a straight-chain fluoroalkyl group containing 1 to 3 carbon atoms; (e) from 0 to 20 mol % of a methacrylic acid alkyl ester having a straight-chain alkyl group containing 4 to 10 carbon atoms; and (f) from 0.1 to 10 mol % of a crosslinking monomer, with the proviso that there is excluded the case where, in the above, said Component (c) is at least one selected from the group consisting of acrylic acid, an acrylic acid alkyl ester having an alkyl group containing 1 to 3 carbon atoms and an acrylic acid fluoroalkyl ester having an fluoroalkvl group containing 1 to 3 carbon atoms; said Component (d) is at least one selected from the group consisting of an acrylic acid alkyl ester having an alkyl group containing 1 to 3 carbon atoms and an acrylic acid fluoroalkyl ester having an fluoroalkyl group containing 1 to 3 carbon atoms; said Component (c) and Component (d) are contained in a total amount of 0 to 10 mole %; and said Component (e) is contained in an amount of 0 mole %. General formula (I): wherein R₁ is at least one selected from the group consisting of a straight-chain fluoroalkyl group represented by the formula: (CH₂)₁-C m F n H p , where 1 is an integer of 1 or 2, m is an integer of 3 to 8, n is an integer of 6 or more, p is an integer of 0 or more, and m, n and p have the relation of n + p = 2m + 1: and a straight-chain alkyl group represented by the formula: C q H 2q+1 , where q is an integer of 4 to 10. General formula (II): wherein R₂ is a straight-chain fluoroalkyl group represented by the formula: (CH₂) w -C x F y H z , where w is an integer of 1 or 2, x is an integer of 1 to 10, y is an integer of 3 or more, z is an integer of 0 or more, and x, y and z have the relation of y + z = 2x + 1.
Claim 2
Dependent Claim 509 words
A non-hydrous soft contact lens comprising a copolymer comprising, as monomer units,: (a) from 33.9 to 89 mol % of an acrylate represented by the general formula (I) shown below; (b) from 4.9 to 65 mol % of a methacrylate represented by the general formula (II) shown below; (c) from 1 to 20 mol % of at least one monomer selected from the group consisting of an unsaturated carboxylic acid, an unsaturated carboxylic acid anhydride an unsaturated carboxylic acid alkyl ester having a branched or cyclic alkyl group which may have a substituent, and an unsaturated carboxylic acid fluoroalkyl ester having a branched or cyclic fluoroalkyl group which may have a substituent; (d) from 0 to 20 mol % of at least one monomer selected from the group consisting of an acrylic acid lower alkyl ester having a straight-chain alkyl group containing 1 to 3 carbon atoms, and an acrylic acid lower fluoroalkyl ester having a straight-chain fluoroalkyl group containing 1 to 3 carbon atoms; (e) from 0 to 20 mol % of a methacrylic acid alkyl ester having a straight-chain alkyl group containing 4 to 10 carbon atoms; and (f) from 0.1 to 10 mol % of a crosslinking monomer, with the proviso that there is excluded the case where, in the above, said Component (c) is at least one selected from the group consisting of acrylic acid, an acrylic acid alkyl ester having an alkyl group containing 1 to 3 carbon atoms and an acrylic acid fluoroalkyl ester having an fluoroalkvl group containing 1 to 3 carbon atoms; said Component (d) is at least one selected from the group consisting of an acrylic acid alkyl ester having an alkyl group containing 1 to 3 carbon atoms and an acrylic acid fluoroalkyl ester having an fluoroalkyl group containing 1 to 3 carbon atoms; said Component (c) and Component (d) are contained in a total amount of 0 to 10 mole %; and said Component (e) is contained in an amount of 0 mole %. General formula (I): wherein R₁ is at least one selected from the group consisting of a straight-chain fluoroalkyl group represented by the formula: (CH₂)₁-C m F n H p , where 1 is an integer of 1 or 2, m is an integer of 3 to 8, n is an integer of 6 or more, p is an integer of 0 or more, and m, n and p have the relation of n + p = 2m + 1: and a straight-chain alkyl group represented by the formula: C q H 2q+1 , where q is an integer of 4 to 10. General formula (II): wherein R₂ is a straight-chain fluoroalkyl group represented by the formula: (CH₂) w -C x F y H z , where w is an integer of 1 or 2, x is an integer of 1 to 10, y is an integer of 3 or more, z is an integer of 0 or more, and x, y and z have the relation of y + z = 2x + 1.
Claim 3
Dependent Claim 16 words
The non-hydrous soft contact lens according to Claim 1, wherein said Component (c) comprises methacrylic acid.
Claim 4
Dependent Claim 23 words
The non-hydrous soft contact lens according to Claim 2, wherein the content of said methacrylic acid is from 2 to 10 mol %.
Claim 5
Dependent Claim 19 words
The non-hydrous soft contact lens according to Claim 1, wherein said Component (c) comprises methacrylic acid and acrylic acid.
Claim 6
Dependent Claim 27 words
The non-hydrous soft contact lens according to Claim 4, wherein the total content of said methacrylic acid and acrylic acid is from 2 to 10 mol %.
Claim 7
Dependent Claim 20 words
The non-hydrous soft contact lens according to Claim 4, wherein said Component (c) consists of methacrylic acid and acrylic acid.
Claim 8
Dependent Claim 61 words
The non-hydrous soft contact lens according to Claim 1, wherein said Component (c) comprises acrylic acid and at least one monomer selected from the group consisting of methacrylic acid alkyl ester having a branched or cyclic alkyl group which may have a substituent and a methacrylic acid fluoroalkyl ester having a branched or cyclic fluoroalkyl group which may have a substituent.
Claim 9
Dependent Claim 22 words
The non-hydrous soft contact lens according to Claim 7, wherein the content of acrylic acid is from 2 to 10 mol %.
Claim 10
Dependent Claim 37 words
The non-hydrous soft contact lens according to Claim 7, wherein Component (c) comprises acrylic acid and at least one monomer selected from the group consisting of t-butyl methacrylate, cyclohexyl methacrylate, benzyl methacrylate, 2,2,2-trifluoro-1-trifluoromethylethyl methacrylate and 2,2,3,4,4,4-hexafluoro-t-hexyl methacrylate.
Claim 11
Dependent Claim 38 words
The non-hydrous soft contact lens according to Claim 1, wherein said Component (a) is at least one selected from the group consisting of 2,2,3,3,4,4,4-­heptafluorobutyl acrylate, 2,2,3,4,4,4-hexafluorobutyl acrylate, 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl acrylate, 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-­heptadecafluorodecyl acrylate, n-butyl acrylate, n-hexyl acrylate, and n-octyl acrylate.
Claim 12
Dependent Claim 34 words
The non-hydrous soft contact lens according to Claim 1, wherein said Component (b) is at least one selected from the group consisting of 2,2,3,4,4,4-­hexafluorobutyl methacrylate, 2,2,3,3,4,4,4-­heptafluorobutyl methacrylate, 3,3,4,4,5,5,6,6,7,7,8,8-­dodecafluorooctyl methacrylate, 3,3,4,4,5,5,6,6,7,7,8,8,8-­tridecafluorooctyl methacrylate and 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl methacrylate.
Claim 13
Dependent Claim 36 words
The non-hydrous soft contact lens according to Claim 1, wherein said Component (c) is at least one selected from the group consisting of methyl acrylate, ethyl acrylate, n-propyl acrylate, 2,2,2-trifluoroethyl acrylate, 2,2,3,3-tetrafluoropropyl acrylate, and 2,2,3,3,3-pentafluoropropyl acrylate.
Claim 14
Dependent Claim 27 words
The non-hydrous soft contact lens according to Claim 1, wherein said Component (e) is selected from the group consisting of n-butyl methacrylate, n-pentyl methacrylate and n-hexyl methacrylate.
Claim 15
Dependent Claim 33 words
The non-hydrous soft contact lens according to Claim 1, wherein said Component (c) is the dimethacrylate of an diol selected from the group consisting of ethylene glycol, diethylene glycol, 1,3-butanediol, 1,4-butanediol and 1,6-hexanediol.
Claim 16
Dependent Claim 20 words
The non-hydrous soft contact lens according to Claim 1 which contains from 5 to 50 % by weight of fluorine.
Claim 17
Dependent Claim 20 words
The non-hydrous soft contact lens accordinging to Claim 1 which has an glass transition temperature of not higher than 20°C.
Claim 18
Dependent Claim 345 words
A process for producing a non-hydrous soft contact lens, comprising: forming a rigid lens substrate in the shape of a contact lens which comprises a rigid copolymer obtained by polymerizing a monomer mixture comprising: (i) from 33.9 to 95 mol % of at least one monomer selected from the group consisting of an unsaturated carboxylic acid, an unsaturated carboxylic acid anhydride, an unsaturated carboxylic acid alkyl ester having a branched or cyclic alkyl group which may have a substituent, and an unsaturated carboxylic acid fluoroalkyl ester having a branched or cyclic fluoroalkyl group which may have a substituent; (ii) from 0 to 46 mol % of at least one monomer selected from the group consisting of an acrylic acid lower alkyl ester having a straight-chain alkyl group containing 1 to 3 carbon atoms, an acrylic acid lower fluoroalkyl ester having a straight-chain fluoroalkyl group containing 1 to 3 carbon atoms, and an acrylate represented by the general formula (I) set out in Claim 1; (iii) from 4.9 to 65 mol % of a methacrylate represented by the general formula (II) set out in Claim 1; and (iv) from 0.1 to 10 mol % of a crosslinking monomer, with the proviso that there is excluded the case where, in the above, said Component (i) is at least one selected from the group consisting of acrylic acid, an acrylic acid alkyl ester having an alkyl group containing 1 to 3 carbon atoms and an acrylic acid fluoroalkyl ester having an fluoroalkyl group containing 1 to 3 carbon atoms; said Component (ii) is at least one selected from the group consisting of an acrylic acid alkyl ester having an alkyl group containing 1 to 3 carbon atoms and an acrylic acid fluoroalkyl ester having an fluoroalkyl group containing 1 to 3 carbon atoms; and said Component (i) and Component (ii) are contained in a total amount of 49.9 to 95 mole %; and subsequently bringing said rigid lens substrate into contact with a straight-chain alcohol having 4 to 10 carbon atoms to effect esterification treatment and/or transesterification treatment.
Claim 19
Dependent Claim 13 words
The process according to Claim 17, wherein said Component (i) comprises methacrylic acid.
Claim 20
Dependent Claim 16 words
The process according to Claim 17, wherein said Component (i) comprises methacrylic acid and acrylic acid.
Claim 21
Dependent Claim 17 words
The process according to Claim 17, wherein said Component (i) consists of methacrylic acid and acrylic acid.
Claim 22
Dependent Claim 58 words
The process according to Claim 17, wherein said Component (i) comprises acrylic acid and at least one monomer selected from the group consisting of methacrylic acid alkyl ester having a branched or cyclic alkyl group which may have a substituent and a methacrylic acid fluoroalkyl ester having a branched or cyclic fluoroalkyl group which may have a substituent.
Claim 23
Dependent Claim 20 words
The process according to Claim 17, wherein said rigid copolymer has a glass transition temperature of not lower than 50°C.
Claim 24
Dependent Claim 35 words
The process according to Claim 17, wherein said straight-chain alcohol having from 4 to 10 carbon atoms is at least one selected from the group consisting of n-­butanol, n-pentanol, n-hexanol, n-heptanol, n-octanol, n-­nonanol and n-decanol.
Claim 25
Dependent Claim 20 words
The process according to Claim 18, wherein said monomer mixture contains from 7 to 40 mol % of methacrylic acid.
Claim 26
Dependent Claim 20 words
The process according to Claim 21, wherein said monomer mixture contains from 7 to 40 mol % of acrylic acid.
Claim 27
Dependent Claim 28 words
The process according to Claim 20, wherein said monomer mixture contains from 50 to 80 mol % of methacrylic acid and acrylic acid in the total amount thereof.

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