Azetidinium-containing copolymers and uses thereof

Patent metadata

Field	Value
Publication number	US-10100219-B2
Application number	US-201615216125-A
Country	US
Kind code	B2
Filing date	Jul 21, 2016
Priority date	Jun 14, 2012
Publication date	Oct 16, 2018
Grant date	Oct 16, 2018

Abstract

The invention is related to azetidinium-containing copolymers and vinylic monomers and their uses in formation of non-silicone hydrogel coatings on silicone hydrogel contact lenses.

First claim

What is claimed is:

1. An azetidinium-containing copolymer comprising: reactive monomeric units derived from at least one vinylic monomer selected from the group consisting of a carboxyl-containing vinylic monomer, an amino-containing vinylic monomer, and combination thereof, wherein the carboxyl-containing vinylic monomer is selected from the group consisting of acrylic acid, a C 1 -C 4 -alkyl acrylic acid, N-2-acrylamidoglycolic acid, and combination thereof, wherein the amino-containing vinylic monomer is selected from the group consisting of amino-C 2 -C 4 alkyl (meth)acrylate, allylamine, vinylamine, amino-C 1 -C 4 alkyl (meth)acrylamide, N-allyl C 1 -C 12 alkanamine, a coupling reaction product of an epoxy compound having one sole epoxy group with allylamine, vinylamine, amino-C 2 -C 6 alkyl (meth)acrylate, or amino-C 2 -C 6 alkyl (meth)acrylamide, a coupling reaction product of an C 1 -C 12 alkanamine or C 2 -C 12 aminoalkanol or with an epoxy-containing vinylic monomer, and combinations thereof; and
azetidinium-containing monomeric units derived from at least one azetidinium-containing vinylic monomer of formula (2)

in which:
R″ is hydrogen or methyl;
p1, p2, and p3 independent of one another are zero or 1;
Y 4 is a linkage selected from the group consisting of a direct bond, —O—, —NR′—, —C(O)—NR′—, —NR′—C(O)—, —O—C(O)—NH—, —NH—C(O)—O—, —NR′—C(O)—NH—, —NH—C(O)—NR′—, —C(O)—O—, —O—C(O)—, R′ is hydrogen, a C 1 -C 20 unsubstituted or substituted, linear or branched alkyl group;
Z 4 , is a direct bond, a C 1 -C 20 unsubstituted or substituted, linear or branched alkylene divalent radical optionally containing therein one or more linkages of —O—, —NR′—, and —C(O)—, a C 1 -C 7 alkyleneoxy C 1 -C 7 alkylene divalent radical, or a divalent radical of —(CH(R″)CH 2 O) r1 —CH(R″)CH 2 — in which R″ is as defined above and r1 is an integer of 1 to 20; and
Z 5 is a C 1 -C 20 unsubstituted or substituted, linear or branched alkyl group, —(CH 2 ) r2 —O—(CH 2 CH 2 O) r1 —Z 6 in which r1 is as defined above, r2 is zero or an integer of 1 to 7, and Z 6 is a C 1 -C 5 alkyl.

2. The azetidinium-containing copolymer of claim 1 , further comprising monomeric units derived from a hydrophobic vinylic monomer, wherein the hydrophobic vinylic monomer is selected from the group consisting of methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, sec-butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, cyclohexylacrylate, 2-ethylhexylacrylate, vinyl acetate, vinyl propionate, vinyl butyrate, vinyl valerate, styrene, chloroprene, vinyl chloride, vinylidene chloride, acrylonitrile, 1-butene, butadiene, methacrylonitrile, vinyl toluene, vinyl ethyl ether, perfluorohexylethyl-thio-carbonyl-aminoethyl-methacrylate, isobornyl methacrylate, trifluoroethyl methacrylate, hexafluoro-isopropyl methacrylate, hexafluorobutyl methacrylate, a siloxane-containing vinylic monomer, a polysiloxane-containing vinylic monomer having about 3 to about 40 silicone atoms, and combinations thereof.

3. The azetidinium-containing copolymer of claim 2 , wherein the azetidinium-containing copolymer comprises reactive monomeric units derived from a carboxyl-containing vinylic monomer selected from the group consisting of acrylic acid, methacrylic acid, ethylacrylic acid, propylacrylic acid, and combinations thereof.

4. The azetidinium-containing copolymer of claim 3 , wherein the azetidinium-containing copolymer comprises reactive monomeric units derived from a carboxyl-containing vinylic monomer selected from the group consisting of methacrylic acid, ethylacrylic acid, and combination thereof.

5. The azetidinium-containing copolymer of claim 3 , wherein the azetidinium-containing copolymer comprises monomeric units derived from at least one hydrophobic vinylic monomer selected from the group consisting of at least one siloxane-containing vinylic monomer, at least one polysiloxane-containing vinylic monomer and combinations thereof.

6. The azetidinium-containing copolymer of claim 2 , wherein the azetidinium-containing copolymer comprises monomeric units derived from at least one hydrophobic vinylic monomer selected from the group consisting of at least one siloxane-containing vinylic monomer, at least one polysiloxane-containing vinylic monomer and combinations thereof.

7. The azetidinium-containing copolymer of claim 6 , wherein the azetidinium-containing copolymer comprises reactive monomeric units derived from at least one amino-containing vinylic monomer selected from the group consisting of: amino-C 2 -C 4 alkyl (meth)acrylate; amino-C 1 -C 4 alkyl (meth)acrylamide; and combinations thereof.

8. The azetidinium-containing copolymer of claim 3 , wherein the azetidinium-containing copolymer comprises reactive monomeric units derived from at least one amino-containing vinylic monomer selected from the group consisting of: amino-C 2 -C 4 alkyl (meth)acrylate; amino-C 1 -C 4 alkyl (meth)acrylamide; and combinations thereof.

9. The azetidinium-containing copolymer of claim 2 , wherein the azetidinium-containing copolymer comprises:
reactive monomeric units which are carboxyl-containing monomeric units and/or amino-containing monomeric units; and further comprises
at least about 50% by moles of non-reactive hydrophilic monomeric units derived from at least one hydrophilic vinylic monomer selected from the group consisting of (meth)acrylamide, N,N-dimethyl (meth)acrylamide, N-vinylpyrrolidone, N,N,-dimethylaminoethyl (meth)acrylate, N,N-dimethylaminopropyl (meth)acrylamide, glycerol methacrylate, 3-acryloylamino-1-propanol, N-hydroxyethyl acrylamide, N-[tris(hydroxymethyl)methyl]-acrylamide, N-methyl-3-methylene-2-pyrrolidone, 1-ethyl-3-methylene-2-pyrrolidone, 1-methyl-5-methylene-2-pyrrolidone, 1-ethyl-5-methylene-2-pyrrolidone, 5-methyl-3-methylene-2-pyrrolidone, 5-ethyl-3-methylene-2-pyrrolidone, 2-hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, C 1 -C 4 -alkoxy polyethylene glycol (meth)acrylate having a weight average molecular weight of up to 1500 Daltons, N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide, N-vinyl-N-methyl acetamide, allyl alcohol, vinyl alcohol which is the hydrolyzed form of vinyl acetate in the azetidinium-containing copolymer, a phosphorylcholine-containing vinylic monomer, erythritol (meth)acrylate, arabitol (meth)acrylate, mannitol (meth)acrylate, ducitol (meth)acrylate, fucitol (meth)acrylate, iditol (meth)acrylate, innositol (meth)acrylate, xylitol (meth)acrylate, sorbitol (meth)acrylate, glucose (meth)acrylate, fructose (meth)acrylate, galactose (meth)acrylate, and combinations thereof.

10. The azetidinium-containing copolymer of claim 9 , wherein the reactive monomeric units are derived from at least one carboxyl-containing vinylic monomer selected from the group consisting of acrylic acid, methacrylic acid, ethylacrylic acid, propylacrylic acid, and combinations thereof; and
at least about 70% by moles of non-reactive hydrophilic monomeric units derived from at least one hydrophilic vinylic monomer selected from the group consisting of (meth)acrylamide, N,N-dimethyl (meth)acrylamide, N-vinylpyrrolidone, N,N,-dimethylaminoethyl (meth)acrylate, glycerol methacrylate, 3-acryloylamino-1-propanol, N-hydroxyethyl acrylamide, N-[tris(hydroxymethyl)methyl]-acrylamide, N-methyl-3-methylene-2-pyrrolidone, 1-ethyl-3-methylene-2-pyrrolidone, 1-methyl-5-methylene-2-pyrrolidone, 1-ethyl-5-methylene-2-pyrrolidone, 5-methyl-3-methylene-2-pyrrolidone, 5-ethyl-3-methylene-2-pyrrolidone, 2-hydroxyethyl (meth)acrylate, C 1 -C 4 -alkoxy pol

Assignees

• Novartis Ag

Inventors

• Holland Troy Vernon
• Chang Frank
• Qiu Yongxing
• Pruitt John Dallas
• Chiang Chung-Yuan
• Shankar Venkat
• Scott Robert
• Kapoor Yash

Classifications

• C08F20/00

  Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof · CPC title

• C09D137/00

  Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen (based on polymers of cyclic esters of polyfunctional acids C09D131/00; based on polymers of cyclic anhydrides of unsaturated acids C09D135/00); Coating compositions based on derivatives of such polymers · CPC title

• B29D11/00865 Primary

  Applying coatings; tinting; colouring (printing, marking or copying processes B41M; identification in general G09F3/00; producing decorative effects in general B44C; positioning or marking of lenses B24B13/0055) · CPC title

• C09D139/04 Primary

  Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member · CPC title

• C09D133/26

  Homopolymers or copolymers of acrylamide or methacrylamide · CPC title