Ocular lens material

• US 5,346,946 A
• Filed: 08/25/1993
• Issued: 09/13/1994
• Est. Priority Date: 08/26/1992
• 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: Yamazaki, Toshio, Ando, Ichiro, Ichinohe, Shoji, Ito, Eri, Yokoyama, Yasuhiro, Iwata, Noriko
• Primary Examiner(s): Schofer, Joseph L.
• Assistant Examiner(s): SAROFIM, NABIL F
• Application Number:
  US08/111,452
• Time in Patent Office: 384 Days
• Field of Search: 526/279, 524/547
• US Class Current: 524/547
• CPC Class Codes: A61F 2/14 Eye parts, e.g. lenses, corneal implants; Implanting instruments specially adapted therefor; Artificial eyes
• CPC Class Codes: A61F 2/16 Intraocular lenses
• CPC Class Codes: A61L 2430/16 for reconstruction of eye parts, e.g. intraocular lens, cornea
• CPC Class Codes: A61L 27/16 obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08G 18/61 Polysiloxanes
• CPC Class Codes: C08G 18/672 Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: G02B 1/041 Lenses
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

An ocular lens material made of a copolymer comprising, as main copolymerizable components, (A) a polysiloxane macromonomer having polymerizable groups bonded via 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 is from 5/95 to 90/10.

Claims

1. An ocular lens material made of a copolymer comprising, as main copolymerizable 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 --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 a covalent bond, an oxygen atom or an alkylene glycol group having from 1 to 6 carbon atoms, E²¹ is --CONH-- (provided that in this case, X²¹ is a covalent bond, and E²¹ forms an urethane bond together with X²⁵) or a bivalent group derived from a diisocyanate selected from the group consisting of saturated or unsaturated aliphatic, alicyclic and aromatic diisocyanates (provided in that this case, X²¹ is an oxygen atom or an alkylene glycol group having from 1 to 6 carbon atoms, and E²¹ forms an urethane bond together with X²¹ and X²⁵), X²⁵ is an oxygen atom or 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;

S¹ is 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 6 carbon atoms, a fluoroalkyl group or a phenyl group, K is an integer of from 1 to 50, and L is an integer of from 0 to (50-K);

U² is a group of the formula (VI);

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

wherein R³³ is a linear or branched alkylene group having from 1 to 6 carbon atoms, X²² is a covalent bond, an oxygen atom or an alkylene glycol group having from 1 to 6 carbon atoms, X²⁶ is an oxygen atom or an alkylene glycol group having from 1 to 6 carbon atoms, and E²² is --CONH (provided that in this case, X²² is a covalent bond, and E²² forms an urethane bond together with X²⁶) or a bivalent group derived from a diisocyanate selected from the group consisting of aturated or unsaturated aliphatic, alicyclic and aromatic diisocyanate (provided that in this case, X²² is an oxygen atom or an alkylene glycol group having from 1 to 6 carbon atoms, and E²² forms an urethane bond together with X²² ; and

X²⁶); and

(B) an alkyl (meth)acrylamide, wherein the weight ratio of the polysiloxane macromonomer to the alkyl (meth)acrylamide is from 5/95 to 90/10, having a water content of at least 5% and the total amount of the polysiloxane macromonomer and the alkyl (meth)acrylamide is at least 25% by weight.

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 copolymerizable component, a silicon-containing monomer selected from the group consisting of a silicon-containing alkyl (meth)acrylate and a silicon-containing styrene derivative, in an amount of not more than 75% by weight, based on the total amount of copolymerizable components.

4. The ocular lens material according to claim 3, wherein the silicon-containing monomer is a silicon-containing styrene derivative.

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

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

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