UV curable crosslinking agents useful in copolymerization
AssigneeBausch & Lomb Incorporated
InventorYu-Chin Lai
Life of this patent
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Abstract
A novel class of compounds are disclosed which may be used as novel crosslinking agents for acrylic-containing, vinyl-containing and/or styrene-containing hydrophilic monomers to prepare novel UV-curable hydrophilic copolymers suitable for use as biomedical articles, especially contact lenses.
Claims88
A composition prepared by polymerizing a monomer mix comprising at least one acrylic-containing monomer, at least one vinyl-containing monomer and a crosslinking agent having the schematic representation:
- ##STR15## wherein V denotes a vinyl-containing group having the formula:
- ##STR16## A' denotes an acrylic-containing group having the formula:
- ##STR17## S denotes a styrene-containing group having the formula:
- ##STR18## wherein R.sub.1, is an alkyl radical derived from substituted and unsubstituted hydrocarbons, polyalkylene oxide, poly(perfluoro) alkylene oxide, dialkyl-capped polydimethylsiloxane, dialkyl-capped polydimethylsiloxane modified with fluoroalkyl or fluoroether groups;
- R.sub.2,-R.sub.10, are independently H, or alkyl of 1 to 5 carbon atoms;
- Q is an organic group containing aromatic moieties having 6-30 carbon atoms;
- X, Y, and Z are independently O, NH or S;
- v' is 1, or higher;
- and
- a', s' are independently greater than or equal to 0, and a'+s' is greater than or equal to 1.
A composition prepared by polymerizing a monomer mix comprising at least one acrylic-containing monomer, at least one vinyl-containing monomer, at least one styrene-containing monomer and a crosslinking agent having the schematic representation:
- ##STR19## wherein V denotes a vinyl-containing group having the formula:
- ##STR20## A' denotes an acrylic-containing group having the formula:
- ##STR21## S denotes a styrene-containing group having the formula:
- ##STR22## wherein R.sub.1, is an alkyl radical derived from substituted and unsubstituted hydrocarbons, polyalkylene oxide, poly(perfluoro) alkylene oxide, dialkyl-capped polydimethylsiloxane, dialkyl-capped polydimethylsiloxane modified with fluoroalkyl or fluoroether groups;
- R.sub.2,-R.sub.10, are independently H, or alkyl of 1 to 5 carbon atoms;
- Q is an organic group containing aromatic moieties having 6-30 carbon atoms;
- X, Y, and Z are independently O, NH or S;
- v' is 1, or higher;
- and
- a', s' are independently greater than or equal to 0, and a'+s' is greater than or equal to 1.
A composition prepared by polymerizing a monomer mix comprising at least one styrene-containing monomer, at least one vinyl-containing monomer and a crosslinking agent having schematic representation:
- ##STR23## wherein V denotes a vinyl-containing group having the formula:
- ##STR24## A' denotes an acrylic-containing group having the formula:
- ##STR25## S denotes a styrene-containing group having the formula:
- ##STR26## wherein R.sub.1, is an alkyl radical derived from substituted and unsubstituted hydrocarbons, polyalkylene oxide, poly(perfluoro) alkylene oxide, dialkyl-capped polydimethylsiloxane, dialkyl-capped polydimethylsiloxane modified with fluoroalkyl or fluoroether groups;
- R.sub.2,-R.sub.10, are independently H, or alkyl of 1 to 5 carbon atoms;
- Q is an organic group containing aromatic moieties having 6-30 carbon atoms;
- X, Y, and Z are independently O, NH or S;
- v' is 1, or higher;
- and
- a', s' are independently greater than or equal to 0, and a'+s' is greater than or equal to 1.
A composition prepared by polymerizing the monomer mix comprising at least one (meth)acrylate-capped or (meth)acrylamide-capped polysiloxane-containing monomer, at least one vinyl-containing monomer, and at least one crosslinking agent of the schematic representation:
- ##STR28## wherein V denotes a vinyl-containing group having the formula:
- ##STR29## A' denotes an acrylic-containing group having the formula:
- ##STR30## S denotes a styrene-containing group having the formula:
- ##STR31## wherein R.sub.1, is an alkyl radical derived from substituted and unsubstituted hydrocarbons, polyalkylene oxide, poly(perfluoro) alkylene oxide, dialkyl-capped polydimethylsiloxane, dialkyl-capped polydimethylsiloxane modified with fluoroalkyl or fluoroether groups;
- R.sub.2,-R.sub.10, are independently H, or alkyl of 1 to 5 carbon atoms;
- Q is an organic group containing aromatic moieties having 6-30 carbon atoms;
- X, Y, and Z are independently O, NH or S;
- v' is 1, or higher;
- and
- a', s' are independently greater than or equal to 0, and a'+s' is greater than or equal to 1.
The composition of claim 54 wherein said vinyl-containing polysiloxane prepolymer is a silicone-containing vinyl carbonate or vinyl carbamate monomer selected from the group consisting of 1,3-bis[4-vinyloxycarbonyloxy)but-1-yl]tetramethyl-disiloxane;
- 3-(trimethylsilyl)propyl vinyl carbonate;
- 3-(vinyloxycarbonylthio)propyl -[tris(trimethylsiloxy)silane];
- 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbamate;
- 3-[tris(trimethylsiloxy)silyl]propyl allyl carbamate;
- 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbonate;
- t-butyldimethylsiloxyethyl vinyl carbonate;
- trimethylsilylethyl vinyl carbonate;
- trimethylsilylmethyl vinyl carbonate;
- and "V.sub.2 D.sub.25 ", represented by the following formula:
- ##STR39##
The composition of claim 54 wherein said vinyl-containing polysiloxane-containing prepolymer comprises urethane, urea, ester or carbonate linkages.
The composition of claim 54 wherein said polysiloxane prepolymer comprises at least one fluoroalkyl-containing group.
A hydrogel prepared by polymerizing a monomer mix comprising methacryloxyethyl vinyl carbonate, N-vinyl pyrrolidone, and 2-hydroxyethyl methacrylate.
A hydrogel prepared by polymerizing a monomer mix comprising N-vinyl pyrrolidone, 2-vinyl-4,4-dimethyl-2-oxazoline-5-one, N,N-dimethyl acrylamide, and methacryloxyethyl vinyl carbonate.
A hydrogel prepared by polymerizing a monomer mix comprising a UV curable hydrogel composition further comprising .alpha.,.omega.-Bis(methacryloxyalkyl) polysiloxane, 3-methacryloxypropyl tris(trimethylsiloxy)silane, N-vinyl pyrrolidone, and methacrlyoxyethyl vinyl carbonate.
A method of making a hydrogel comprising the steps of
- a) forming a monomer mix combining at least one acrylic-containing monomer and at least one vinyl-containing monomer and a crosslinking agent having the schematic representation:
- ##STR40## wherein V denotes a vinyl-containing group having the formula:
- ##STR41## A' denotes an acrylic-containing group having the formula:
- ##STR42## S denotes a styrene-containing group having the formula:
- ##STR43## wherein R.sub.1, is an alkyl radical derived from substituted and unsubstituted hydrocarbons, polyalkylene oxide, poly(perfluoro) alkylene oxide, dialkyl-capped polydimethylsiloxane, dialkyl-capped polydimethylsiloxane modified with fluoroalkyl or fluoroether groups;
- R.sub.2,-R.sub.10, are independently H, or alkyl of 1 to 5 carbon atoms;
- Q is an organic group containing aromatic moieties having 6-30 carbon atoms;
- X, Y, and Z are independently O, NH or S;
- v' is 1, or higher;
- and
- a', s' are independently greater than or equal to 0, and a'+s' is greater than or equal to 1;
- b) curing the mix of step a) to form a polymer;
- and
- c)hydrating the polymer produced in b) to form a hydrogel.
A method of making a hydrogel composition comprising the steps of
- a) forming a monomer mix combining at least one acrylic-containing, at least one vinyl-containing, at least one styrene-containing monomer and a crosslinking agent having the schematic representation:
- ##STR44## wherein V denotes a vinyl-containing group having the formula:
- ##STR45## A' denotes an acrylic-containing group having the formula:
- ##STR46## S denotes a styrene-containing group having the formula:
- ##STR47## wherein R.sub.1, is an alkyl radical derived from substituted and unsubstituted hydrocarbons, polyalkylene oxide, poly(perfluoro) alkylene oxide, dialkyl-capped polydimethylsiloxane, dialkyl-capped polydimethylsiloxane modified with fluoroalkyl or fluoroether groups;
- R.sub.2,-R.sub.10, are independently H, or alkyl of 1 to 5 carbon atoms;
- Q is an organic group containing aromatic moieties having 6-30 carbon atoms;
- X, Y, and Z are independently O, NH or S;
- v' is 1, or higher;
- and
- a', s' are independently greater than or equal to 0, and a'+s' is greater than or equal to 1;
- b) curing the mix of step a) to form a polymer;
- and
- c) hydrating the polymer produced in b) to form a hydrogel.
Dependencies are inferred from the claim text.