Soft ocular lens material

• US 4,954,586 A
• Filed: 01/03/1990
• Issued: 09/04/1990
• Est. Priority Date: 01/17/1989
• Status: Expired due to Term

• Current Assignee: Menicon Company Limited, Shin-Etsu Chemical Company Limited
• Original Assignee: Menicon Company Limited, Shin-Etsu Chemical Company Limited
• Inventors: Yoshioka, Hiroshi, Yamazaki, Toshio, Itagaki, Akinari, Shibata, Takanori, Ando, Ichiro, Hirashima, Atsushi, Iwata, Noriko, Toyoshima, Nobuyuki
• Primary Examiner(s): Schofer, Joseph L.
• Assistant Examiner(s): Sarofim, N.
• Application Number:
  US07/460,662
• Time in Patent Office: 244 Days
• Field of Search: 526/245, 526/279, 523/107
• US Class Current: 526/245
• CPC Class Codes: C08F 220/22 Esters containing halogen
• CPC Class Codes: C08F 283/124 on to polysiloxanes having carbon-to-carbon double bonds
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08F 290/148 Polysiloxanes
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

A soft ocular lens material is formed of a copolymer consisting essentially of:

(A) from 5 to 70 parts by weight of a fluorine containing (meth)acrylate;

(B) from 5 to 60 parts by weight of an alkyl (meth)acrylate;

(C) from 3 to 45 parts by weight of a polysiloxane macromonomer having pllymerizable groups at both terminals; and

(D) from 3 to 40 parts by weight of a polysiloxane macromonomer having polymerizable groups bonded via one or two urethane bonds to the siloxane main chain.

Claims

1. A soft ocular lens material made of a copolymer consisting essentially of:

(A) from 5 to 70 parts by weight of a fluorine-containing (meth)acrylate of the formula III;

space="preserve" listing-type="equation">CH.sub.2 =CR.sup.7 COOCpH.sub.( 2p-q-r=l)Fq(OH).sub.r (III)

wherein R₇ represents a hydrogen atom or a methyl groups, p is an integer of form 1 to 15, q is an integer of from 1 to (2p+1), and r is an integer of from 0 to 2.

(B) from 5 to 60 parts by weight of an alkyl (meth)acrylate;

(C) from 3 to 45 parts by weight of a polysiloxane macromonomer having polymerizable groups at both terminals, of the formula I;

##STR54## wherein each of Y¹¹ and Y¹² independently represents an acryloyl group, a methacryloyl group, a vinyl group or an allyl group;

each of X¹¹ and X¹² independently represents a covalent bond, an oxygen atom or an alkylene glycol group;

each of R¹¹ and R¹² independently represents a linear or branched alkylene group having from 1 to 6 carbon atoms;

each of R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷ and R¹⁸ independently represents an alkyl group having from 1 to 3 carbon atoms or a phenyl group;

i is an integer of from 1 to 1500; and

j is an integer of from 0 to 1499 (provided that i+j is at most

     1500); and

(D) from 3 to 40 parts by weight of a polysiloxane macromonomer having polymerizable groups bonded via one or two urethane bonds to the siloxane main chain, of the formula II;

##STR55## wherein each of Y²¹ and Y²² independently represents a group selected from the group consisting of an acryloyloxy group, a methacryloyloxy group, a vinyl group and an allyl group;

each of R³¹ and R³⁴ independently represents a linear or branched alkylene group having from 2 to 6 carbon atoms;

each of X²¹ and X²² independently represents a covalent bond, an oxygen atom or an alkylene glycol group;

each of R³² and R³³ independently represents a linear or branched alkylene group having from 1 to 6 carbon atoms;

each of R²³, R²⁴, R²⁵, R²⁶, R²⁷ and R²⁸ independently represents an alkyl group having from 1 to 3 carbon atoms or a phenyl group;

each of E²¹ and E²² independently represents --NHCO-- (provided that in this case, each of X²¹ and X²² is a covalent bond, E²¹ forms a urethane bond together with X²⁵, and E²² forms a urethane bond together with X²⁶) or a bivalent group derived from a diisocyanate selected from the group consisting of saturated aliphatic, alicyclic and aromatic diisocyanates (provided that in this case, X²¹ and X²² independently represents an oxygen atom or an alkylene glycol group, E²¹ forms a urethane bond together with X²¹ and X²⁵, and E²² forms a urethane bond together with X²² and X²⁶);

each of X²⁵ and X²⁶ independently represents an oxygen atom, an alkylene glycol or a group represented by the formula V;

##STR56## wherein R⁴¹ is a trivalent hydrocarbon group having from 1 to 6 carbon atoms;

Y²³ represents a group selected from the group consisting of an acryloyloxy group, a methacryloyloxy group, a vinyl group and a allyl group;

R³⁶ represents a linear or branched alkylene group having from 2 to 6 carbon atoms;

X²³ represents a covalent bond, an oxygen atom or an alkylene glycol group;

E²³ represents --NHCO-- (provided that in this case, X²³ is a covalent bond) or a bivalent group derived from a diisocyanate selected from the group consisting of saturated aliphatic, alicyclic and aromatic diisocyanates (provided that in this case, X²³ is an oxygen atom or an alkylene glycol group), which forms a urethane bond together with X²³ and the adjacent oxygen atom bonded to R⁴¹ ;

a is an integer of from 1 to 1500; and

b is an integer of from 0 to 1499, provided a+b≦

1500;

as essential copolymer components.

2. The soft ocular lens material according to claim 1, wherein the polysiloxane macromonomer (D) is a macromonomer of the formula VII:

##STR57## wherein each of Y¹²¹ and Y¹²² independently represents an acryloyl group, a methacryloyl group, a vinyl group or an allyl group;

each of X¹²¹, X¹²², X¹²³ and X¹²⁴ independently represents an oxygen atom or an alkylene glycol group;

each of R¹²¹ and R¹²² independently represents a linear or branched alkylene group having from 1 to 6 carbon atoms;

each of R¹²³, R¹²⁴, R¹²⁵, R¹²⁶, R¹²⁷ and R¹²⁸ independently represents an alkyl group having from 1 to 3 carbon atoms or a phenyl group;

each of E¹²¹ and E¹²² independently represents a bivalent group derived from a saturated aliphatic, alicyclic or aromatic diisocyanate, and E¹²¹ forms a urethane bond together with X¹²¹ and X¹²², and E¹²² forms a urethane bond together with X¹²³ and X¹²⁴ ;

m is an integer of from 1 to 1500; and

n is an integer of from 0 to 1499 (provided m+n is not more than

     1500).

3. The soft ocular lens material according to claim 1, wherein the polysiloxane macromonomer (D) is a macromonomer of the formula VIII:

##STR58## wherein each of Y²²¹ and Y²²² independently represents an acryloyloxy group, a methacryloyloxy group, a vinyl group or an allyl group, each of R²³¹ and R²³⁴ independently represents a linear or branched alkylene group having from 2 to 6 carbon atoms;

each of X²²¹ and X²²² independently represents an oxygen atom or an alkylene glycol group;

each of R²³² and R²³³ independently represents a linear or branched alkylene group having from 1 to 6 carbon atoms;

each of R²²³, R²²⁴, R²²⁵, R²²⁶, R²²⁷ and R²²⁸ independently represents an alkyl group having from 1 to 3 carbon atoms or a phenyl group;

each of E²²¹ and E²²² independently represents --NHCO--;

c is an integer of from 1 to 1500; and

d is an integer of from 0 to 1499, provided c+d is not more than 1500.

4. The soft ocular lens material according to claim 1, wherein the polysiloxane macromonomer (D) is a macromonomer of the formula IX:

##STR59## wherein each of Y³²¹ and Y³²² independently represents a group selected from the group consisting of an acryloyloxy group, a methacryloyloxy group, a vinyl group and an allyl group;

each of R³³¹ and R³³⁴ independently represents a linear or branched alkylene group having from 2 to 6 carbon atoms;

each of X³²¹ and X³²² independently represents a covalent bond, an oxygen atom or an alkylene glycol group;

each of R³³² and R³³³ independently represents a linear or branched alkylene group having from 1 to 6 carbon atoms;

each of R³²³, R³²⁴, R³²⁵, R³²⁶, R³²⁷ and R³²⁸ independently represents an alkyl group having from 1 to 3 carbon atoms or a phenyl group;

each of E³²¹ and E³²² independently represents --NHCO-- (provided that in this case, each of X³²¹ and X³²² is a covalent bond, and E³²¹ forms a urethane bond together with X³²⁵, and E³²² forms a urethane bond together with X³²⁶) or a bivalent group derived from a diisocyanate selected from the group consisting of saturated aliphatic, alicyclic and aromatic diisocyanates (provided that in this case, each of X³²¹ and X³²² independently represents an oxygen atom or an alkylene glycol group, and E³²¹ forms a urethane bond together with X³²¹ and X³²⁵, and E³²² forms a urethane bond together with X³²² and X³²⁶);

each of X³²⁵ and X³²⁶ independently represents a group of the formula V as defined in claim 1;

e is an integer of from 1 to 1500 and f is an integer of from 0 to 1499, provided e+f≦

1500.

5. The soft ocular lens material according to claim 1, wherein the alkyl (meth)acrylate (B) is at least one member selected from the group consisting of methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, tert-butyl (meth)acrylate, isobutyl (meth)acrylate, pentyl (meth)acrylate, tert-pentyl (meth)acrylate, hexyl (meth)acrylate, heptyl (meth)acrylate, octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate, dodecyl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, and cyclohexyl (meth)acrylate.

6. The soft ocular lens material according to claim 1, wherein the alkyl (meth)acrylate (B) is an alkyl (meth)acrylate, of which the glass transition temperature of a homopolymer with a molecular weight of at least about 10,000, would be not higher than 40°

C.

7. The soft ocular lens material according to claim 1, wherein the alkylene glycol group for each of X¹¹, X¹², X²¹, X²² and X²³ is a group of the formula IV:

space="preserve" listing-type="equation">--O--C.sub.k H.sub.2k --O).sub.l (IV)

wherein k is an integer of from 2 to 4, and l is an integer of from 1 to 5.

8. The soft ocular lens material according to claim 1, wherein R⁴¹ in the formula V is a trivalent hydrocarbon group of the formula VI:

##STR60## wherein s is an integer of from 0 to 5, t is an integer of from 0 to 5, and u is an integer of from 0 to 5, provided s+t+u is an integer of from 0 to 5.

9. The soft ocular lens material according to claim 1, which further contains at least one member selected from the group consisting of from 0.01 to 10 parts by weight of a cross-linking agent, not more than 30 parts by weight of a reinforcing monomer, not more than 30 parts by weight of an oxygen-permeability-imparting monomer, not more than 3 parts by weight of a polymerizable ultraviolet absorber, not more than 3 parts by weight of a polymerizable dyestuff and not more than 3 parts by weight of a polymerizable ultraviolet absorbing dyestuff, per 100 parts by weight of the total amount of the essential components (A), (B), (C) and (D).

10. The soft ocular lens material according to claim 1, which is subjected to alkali treatment.

11. A soft ocular lens obtained by shaping the soft ocular lens material of claim 1 into a desired shape, followed by alkali treatment.