Ocular lens material

• US 5,416,132 A
• Filed: 08/24/1993
• Issued: 05/16/1995
• Est. Priority Date: 08/24/1992
• Status: Expired due to Fees

• Current Assignee: Menicon Company Limited, Shin-Etsu Chemical Company Limited
• Original Assignee: Menicon Company Limited, Shin-Etsu Chemical Company Limited
• Inventors: Ito, Eri, Yamazaki, Toshio, Ando, Ichiro, Ichinohe, Shoji, Yokoyama, Yasuhiro, Iwata, Noriko
• Primary Examiner(s): Michl, Paul R.
• Assistant Examiner(s): MERRIAM, ANDREW EDWIN
• Application Number:
  US08/110,946
• Time in Patent Office: 630 Days
• Field of Search: 351/160 H, 523/107, 526/279, 526/301, 526/307.3, 526/, 528/32, 528/25, 528/28
• US Class Current: 523/107
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

An ocular lens material made of a copolymer consisting essentially of (A) a polysiloxane macromonomer having polymerizable groups bonded by one or more urethane bonds to the siloxane main chain and (B) an alkyl (meth)acrylamide, wherein the weight ratio of the polysiloxane macromonomer to the alkyl (meth)acrylamide ranges from 10:90 to 90:10.

Claims

1. An ocular lens material made of a copolymer comprising, as main copolymer components, (A) a polysiloxane macromonomer having polymerizable groups bonded via one or more urethane bonds to the siloxane main chain, of the formula (I):

space="preserve" listing-type="equation">A.sup.1 -U.sup.1 -(-S.sup.1 -U.sup.2 -).sub.n -S.sup.2 -U.sup.3 -A.sup.2(I)

wherein A¹ is a group of the formula (II);

space="preserve" listing-type="equation">Y.sup.21 -R.sup.31 - (II)

wherein Y²¹ is an acryloyloxy group, a methacryloyloxy group, a vinyl group or an allyl group, and R³¹ is a linear or branched alkylene group having from 2 to 6 carbon atoms;

A² is a group of the formula (III);

space="preserve" listing-type="equation">R.sup.34 -Y.sup.22 (III)

wherein Y²² is an acryloyloxy group, a methacryloyloxy group, a vinyl group or an allyl group, and R³⁴ is a linear or branched alkylene group having from 2 to 6 carbon atoms;

U¹ is a group of the formula (IV);

space="preserve" listing-type="equation">-X.sup.21 -E.sup.21 -X.sup.25 -R.sup.32 - (IV)

wherein X²¹ is an oxygen atom or an alkylene glycol group having from 1 to 6 carbon atoms, E²¹ is a bivalent group derived from a diisocyanate selected from the group consisting of saturated aliphatic, alicyclic and aromatic diisocyanates, X²⁵ is an alkylene glycol group having from 1 to 6 carbon atoms, and R³² is a linear or branched alkylene group having from 1 to 6 carbon atoms;

each of S¹ and S² independently represents a group of the formula (V);

##STR6## wherein 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, K is an integer of from 1 to 50, and L is zero or an integer up to (50-K);

U² is a group of the formula (VI);

space="preserve" listing-type="equation">-R.sup.37 -X.sup.27 -E.sup.24 -X.sup.28 -R.sup.38 - (VI)

wherein each of R³⁷ and R³⁸ independently represents a linear or branched alkylene group having from 1 to 6 carbon atoms, each of X²⁷ and X²⁸ independently represent an alkylene glycol group having from 1 to 6 carbon atoms, and E²⁴ is a bivalent group derived from a diisocyanate selected form the group consisting of saturated aliphatic, alicyclic and aromatic diisocyanates (provided that in this case, E²⁴ forms a urethane bond together with X²⁷ and X²⁸);

U³ is a group of the formula (VII);

space="preserve" listing-type="equation">-R.sup.33 -X.sup.26 -E.sup.22 -X.sup.22 -

wherein R³³ is a linear or branched alkylene group having from 1 to 6 carbon atoms, X²² is an oxygen atom or an alkylene glycol group having from 1 to 6 carbon atoms, X²⁶ is an alkylene glycol group having from 1 to 6 carbon atoms, and E²² is a bivalent group derived from a diisocyanate selected from the group consisting of saturated aliphatic, alicyclic and aromatic diisocyanates; and

n is an integer of at least 1; and

(B) an alkyl(meth)acrylamide, wherein the weight ratio of the polysiloxane macromonomer to the alkyl(meth)acrylamide is from 10;

90 to 90;

10.

2. The ocular lens material according to claim 1, wherein the alkyl (meth)acrylamide is N,N-dimethyl methacrylamide.

3. The ocular lens material according to claim 1 or 2, wherein the copolymer contains, as a further copolymer component, a siloxane monomer selected from the group consisting of an organopolysiloxane-containing alkyl (meth)acrylate and an organopolysiloxane-containing styrene derivative, in an amount of not more than 70% by weight, based on the total amount of copolymer components.

4. The ocular lens material according to claim 3, wherein the siloxane monomer is an organopolysiloxane-containing styrene derivative.

5. The ocular lens material according to claim 3 or 4, wherein the organopolysiloxane-containing styrene derivative is tris(trimethylsiloxy)silylstyrene.

6. The ocular lens material according to claim 3, wherein the siloxane monomer is an organopolysiloxane-containing alkyl (meth)acrylate.

7. The ocular lens material according to claim 3 or 6, wherein the organopolysiloxane-containing alkyl (meth)acrylate is tris(trimethylsiloxy)silylpropyl (meth)acrylate.

8. The ocular lens material according to claim 1, wherein the total amount of (A) polysiloxane macromonomer and (B) alkyl (meth)acrylamide is at least 30% by weight of the material.