Silicone-containing prepolymers and low water materials

• US 5,981,669 A
• Filed: 04/29/1998
• Issued: 11/09/1999
• Est. Priority Date: 12/29/1997
• Status: Expired due to Term

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Lai, Yu-Chin, Valint, Paul L. Jr., Quinn, Edmond T., Ammon, Daniel M. Jr.
• Primary Examiner(s): Smith, Jeffrey T.
• Assistant Examiner(s): LU, C CAIXIA
• Application Number:
  US09/069,785
• Time in Patent Office: 559 Days
• Field of Search: 528/26, 528/28, 528/29, 528/38, 526/279, 525/477
• US Class Current: 525/477
• CPC Class Codes: C08F 283/12 on to polysiloxanes
• CPC Class Codes: C08G 18/61 Polysiloxanes
• CPC Class Codes: C08G 18/6469 having silicon
• CPC Class Codes: C08G 77/442 containing vinyl polymer sequences
• CPC Class Codes: C08L 75/04 Polyurethanes
• CPC Class Codes: C08L 83/10 Block- or graft-copolymers containing polysiloxane sequences obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C08L51/08, C08L53/00
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

Low water silicone-containing elastomers are based on a hydroxy- or amino-terminated prepolymer derived from an ethylenically unsaturated silicon-containing monomer, and at least one monomer reactive with hydroxyl- or amino-functional radicals of the prepolymer. The elastomers are especially useful as contact lens materials.

Claims

1. A thermoplastic elastomer which is the polymerization product of a monomer mixture comprising:

(A) a hydroxy- or amino-terminated prepolymer prepared by reacting the following components;

(a) at least 60 mole % of an ethylenically unsaturated silicon-containing monomer,

(b) 2.5 to 20 mole % of an ethylenically unsaturated monomer containing a hydroxyl or amino radical,

(c) 2.5 to 20 mole % of a chain transfer agent that provides the prepolymer with hydroxyl- or amino-functional radicals, and

(d) 0 to 20 mole % of an ethylenically unsaturated monomer other than monomers (a), (b) or (c),

the mole percent of components (a), (b), (c) and (d) being based on the total molar amount of said components; and

(B) at least one monomer reactive with hydroxyl- or amino-functional radicals of the prepolymer.

2. The thermoplastic elastomer of claim 1, wherein component B of the monomer mixture comprises a silicone containing monomer endcapped with hydroxy or amino radicals.

3. The thermoplastic elastomer of claim 2, wherein component B of the monomer mixture further comprises a diisocyanate.

4. The thermoplastic elastomer of claim 3, wherein component B of the monomer mixture further comprises a diol or glycol having 1 to 40 carbon atoms.

5. The thermoplastic elastomer of claim 4, wherein the monomer mixture includes an alkylene or oxyalkylene diol having 1 to 10 carbon atoms.

6. The thermoplastic elastomer of claim 3, wherein component B of the monomer mixture includes a dihydroxy- or diamine-terminated silicone-containing monomer.

7. The thermoplastic elastomer of claim 6, wherein the silicone-containing monomer has the formula:

##STR4## wherein each R is independently selected from an alkylene group having 1 to 10 carbon atoms wherein the carbon atoms may include ether, urethane or ureido linkages therebetween;

each R'"'"' is independently selected from monovalent hydrocarbon radicals or halogen substituted monovalent hydrocarbon radicals having 1 to 18 carbon atoms which may include ether linkages therebetween, and

a is an integer equal to or greater than 1.

8. The thermoplastic elastomer of claim 7, wherein the monomer mixture further comprises a diol or glycol having 1 to 40 carbon atoms.

9. The thermoplastic elastomer of claim 8, wherein the diol is neopentyl glycol.

10. The thermoplastic elastomer of claim 1, which is the polymerization product of a mixture that includes a hydroxy- or amino-terminated prepolymer (A), a dihydroxy-terminated silicone-containing monomer, a diisocyanate, and an alkylene or oxyalkylene diol having 1 to 10 carbon atoms.

11. The thermoplastic elastomer of claim 1, wherein component (a) of the prepolymer is a compound of Formula (II):

##STR5## wherein;

X denotes --COO--, --CONR⁴ --, --OCOO--, or --OCONR⁴ -- where each where R⁴ is H or lower alkyl;

R³ denotes hydrogen or methyl;

h is 1 to 10; and

each R² independently denotes a lower alkyl radical, a phenyl radical or a radical of the formula

space="preserve" listing-type="equation">--Si(R.sup.5).sub.3

wherein each R⁵ is independently a lower alkyl radical or a phenyl radical.

12. The thermoplastic elastomer of claim 1, wherein component (b) of the prepolymer is selected from the group consisting of hydroxyl-sub stituted (meth)acrylates, hydroxyl-substituted (meth)acrylamides, amino-substituted (meth)acrylates and amino-substituted (meth)acrylamides.

13. The thermoplastic elastomer of claim 12, wherein component (b) of the prepolymer is at least one hydroxyl-substituted (meth)acrylate selected from the group consisting of 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, glycidyl methacrylate, glycidyl acrylate, polyethylene glycol methacrylate, and polyethylene glycol acrylate.

14. The thermoplastic elastomer of claim 11, wherein chain transfer agent (c) of the prepolymer is 2-mercaptoethanol.

15. The thermoplastic elastomer of claim 1, wherein the prepolymer is based on a copolymer of tris(trimethylsiloxy) methacryloxy propylsilane, 2-hydroxyethyl methacrylate and mercaptoethanol.

16. A contact lens formed of a thermoplastic elastomer according to claim 1.

17. A contact lens formed of a thermoplastic elastomer according to claim 6.

18. A contact lens formed of a thermoplastic elastomer according to claim 10.

19. A contact lens formed of a thermoplastic elastomer according to claim 15.

20. The contact lens of claim 16, having a water content less than 5 weight percent and a modulus of elasticity of about 20 g/mm² to about 150 g/mm².

21. The thermoplastic elastomer of claim 9, wherein the diisocyante is isophorone diisocyanate.