IP Library Granted Patent US 9,422,447
Granted Patent B2
US 9,422,447 · App. 13/913,734 · Granted Aug 23, 2016

Azetidinium-containing copolymers and uses thereof

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Quick Facts
Patent No.
US 9,422,447
App. No.
13/913,734
Granted
Aug 23, 2016
Kind
B2
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.

Claims (16)

1. An azetidinium-containing vinylic monomer, being represented by 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 vinylic monomer of claim 1 , wherein the azetidinium-containing vinylic monomer is obtained by reacting epichlorohydrin directly with a vinylic monomer having a secondary amine group.

3. The azetidinium-containing vinylic monomer of claim 2 , wherein the vinylic monomer having a secondary amine group is N-allyl C 1 -C 12 alkanamine.

4. The azetidinium-containing vinylic monomer of claim 3 , wherein the N-allyl C 1 -C 12 alkanamine is N-ethyl-2-methylallylamine, N-ethylallylamine, N-allylmethylamine, N-allyl-1-pentanamine, N-allyl-2-methyl-1-pentanamine, N-Allyl-2,3-dimethyl-1-pentanamine, N-allyl-1-hexanamine, N-allyl-2-methyl-1-hexanamine, N-allyl-1-heptanamine, N-allyl-1-octanamine, N-allyl-1-ecanamine, or N-allyl-1-dodecanamine.

5. The azetidinium-containing vinylic monomer of claim 2 , wherein the vinylic monomer having a secondary amine group is obtained by reacting 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.

6. The azetidinium-containing vinylic monomer of claim 5 , wherein the epoxy compound is 1,2-epoxy C 3 -C 12 alkanes.

7. The azetidinium-containing vinylic monomer of claim 5 , wherein the epoxy compound is a mono-epoxy terminated polyethyleneglycol.

8. The azetidinium-containing vinylic monomer of claim 2 , wherein the vinylic monomer having a secondary amine group is obtained by reacting a C 1 -C 12 alkanamine or amino-C 2 -C 12 alkanol with an epoxy-containing vinylic monomer.

9. The azetidinium-containing vinylic monomer of claim 8 , wherein the epoxy-containing vinylic monomer is glycidyl (meth)acrylate, vinyl glycidyl ether, or allyl glycidyl ether.

Assignments (2)
CONFIRMATORY DEED OF ASSIGNMENT EFFECTIVE APRIL 8, 2019 Recorded Dec 10, 2019
From: NOVARTIS AG
To: ALCON INC.
Reel/Frame 051454/0788 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 15, 2013
From: HOLLAND, TROY VERNON; CHANG, FRANK; QIU, YONGXING; PRUITT, JOHN DALLAS; CHIANG, CHUNG-YUAN; SHANKERNARAYANAN, MANIVAKKAM J.; SCOTT, ROBERT; KAPOOR, YASH
To: NOVARTIS AG
Reel/Frame 030796/0733 →