Monomeric units useful for reducing the modulus of silicone hydrogels

• US 5,908,906 A
• Filed: 10/10/1997
• Issued: 06/01/1999
• Est. Priority Date: 12/07/1995
• Status: Expired due to Term

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Kunzler, Jay F., Ozark, Richard M.
• Primary Examiner(s): Smith, Jeffrey T.
• Assistant Examiner(s): Sarofim, N.
• Application Number:
  US08/947,490
• Time in Patent Office: 599 Days
• Field of Search: 526/279, 523/107, 351/160 R
• US Class Current: 526/279
• CPC Class Codes: C07F 7/0838 Compounds with one or more Si-O-Si sequences compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21
• CPC Class Codes: C08L 43/04 Homopolymers or copolymers of monomers containing silicon
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

Monomeric units useful in reducing the modulus of hydrogels are disclosed. Silicone hydrogels including the subject monomeric units are especially useful in the formation of biomedical articles such as silicone hydrogel contact lenses. ##STR1## wherein: A is an activated unsaturated group;

R and D independently are alkyl, alkylene or haloalkyl groups having 1 to 10 carbon atoms wherein said carbon atoms may include ether linkages therebetween;

R₁, R₂, R₃ and R₄ are independently selected from: alkyl or haloalkyl groups wherein ether linkages may be included between carbon atoms; siloxane groups, and carbocyclic ring groups having from 6 to 18 carbon atoms;

m is an integer from 1 to 500; n is an integer from 1 to 20; x and y are 0 or 1;

z is 1 or 2; and x+y+z=3;

so long as at least one of R₁ or R₂ is an alkyl group having from 1 to 10 carbon atoms.

Claims

1. A hydrogel composition formed by polymerizing a monomer mix comprising monomeric units represented by Formula I:

##STR21## wherein;

A is an activated unsaturated group;

R and D independently are alkyl, alkylene or haloalkyl groups having 1 to 10 carbon atoms wherein said carbon atoms may include ether linkages therebetween;

R₁, R₂, R₃ and R₄ are independently selected from;

alkyl or haloalkyl groups wherein ether linkages may be included between carbon atoms;

siloxane groups; and

carbocyclic ring groups having from 6 to 18 carbon atoms;

m is an integer from 1 to 500;

n is an integer from 1 to 20;

x and y are 0 or 1;

z is 1 or 2;

and x+y+z=3;

so long as at least one of R₁ or R₂ is an alkyl group having from 1 to 10 carbon atoms.

2. The composition of claim 1 wherein z is 1 and R₁, R₂, R₃ and R₄ are independently selected from alkyl groups having from 1 to 10 carbon atoms.

3. The composition of claim 2 wherein at least one of said alkyl groups is fluoro-substituted.

4. The composition of claim 1 wherein A is a group selected from:

an ester or amide of acrylic acid or methacrylic acid.

5. The composition of claim 1 wherein R and D are alkyl groups having from 1 to 6 carbon atoms wherein said carbon atoms may include ether linkages therebetween;

n is from 1 to 6; and

m is from 1 to 10.

6. The composition of claim 1 wherein the monomeric units represented by Formula I include monomeric units represented by Formula II:

##STR22##

7. The composition of claim 1 formed by polymerizing a monomer mix comprising the following:

(a) from about 10 to about 89 weight percent of silicone-containing monomeric units;

(b) from about 10 to about 70 weight percent of hydrophilic monomeric units; and

(c) from about 1 to about 50 weight percent of the monomeric units represented by Formula I.

8. The composition of claim 7 wherein said silicone-containing monomeric units comprise monomeric units represented by Formula III:

##STR23## wherein;

A'"'"' and A" are activated unsaturated groups;

R'"'"' and R" independently are an alkyl or alkylene group having 1 to 10 carbon atoms wherein the carbon atoms may include ether linkages therebetween;

R₈ through R₁₇ are independently selected from the groups described with reference to R₁ though R₄ ;

a is an integer equal to or greater than 1;

b and c are integers equal to or greater than 0, and

a+b+c equals an integer from 1 to 1000.

9. The composition of claim 8 wherein A'"'"' and A" are groups selected from:

an ester or amide of acrylic acid or methacrylic acid;

R'"'"' and R" are selected from are alkyl groups having from 1 to 6 carbon atoms wherein said carbon atoms may include ether linkages therebetween;

R₈ through R₁₇ are independently selected from alkyl groups having from 1 to 10 carbon atoms.

10. A contact lens comprising a hydrogel composition formed by polymerizing a monomer mix comprising monomeric units represented by Formula I:

##STR24## wherein;

A is an activated unsaturated group;

R and D independently are alkyl, alkylene or haloalkyl groups having 1 to 10 carbon atoms wherein said carbon atoms may include ether linkages therebetween;

R₁, R₂, R₃ and R₄ are independently selected from;

alkyl or haloalkyl groups wherein ether linkages may be included between carbon atoms;

siloxane groups; and

carbocyclic ring groups having from 6 to 18 carbon atoms;

m is an integer from 1 to 500;

n is an integer from 1 to 20;

x and y are 0 or 1;

z is 1 or 2; and

x+y+z=3;

so long as at least one of R₁ or R₂ is an alkyl group having from 1 to 10 carbon atoms.

11. The contact lens of claim 10 wherein z is 1;

R₁, R₂, R₃, and R₄ are independently selected from alkyl groups having from 1 to 10 carbon atoms;

A is a group selected from;

an ester or amide of acrylic acid or methacrylic acid;

R and D are alkyl groups having from 1 to 6 carbon atoms wherein said carbon atoms may include ether linkages therebetween, m is from 1 to 10; and

n is from 1 to 6.

13. The contact lens of claim 10 wherein said silicone hydrogel is polymerized from a monomer mix comprising:

(a) from about 10 to about 89 weight percent of silicone-containing monomeric units;

(b) from about 10 to about 70 weight percent of hydrophilic monomeric units; and

(c) from about 1 to about 50 weight percent of the monomeric units represented by Formula I.

14. The contact lens of claim 13 wherein said silicone-containing monomeric units comprise monomeric units represented by Formula III:

##STR26## wherein;

A'"'"' and A" are activated unsaturated groups;

R'"'"' and R" independently are an alkyl or alkylene group having 1 to 10 carbon atoms

wherein the carbon atoms may include ether linkages therebetween;

R₈ through R₁₇ are independently selected from the groups described with reference to R₁ though R₄,

a is an integer equal to or greater than 1;

b and c are integers equal to or greater than 0; and

a+b+c equals an integer from 1 to 1000.

15. The contact lens of claim 14 wherein A'"'"' and A" are groups selected from:

an ester or amide of acrylic acid or methacrylic acid;

R'"'"' and R" are selected from are alkyl groups having from 1 to 6 carbon atoms wherein said carbon atoms may include ether linkages therebetween; and

R₈ through R₁₇ are independently selected from alkyl groups having from 1 to 10 carbon atoms.

16. The contact lens of claim 10 wherein said composition has a Young'"'"'s modulus of elasticity from about 20 g/mm² to about 150 g/mm².

12. The contact lens of claim 19 wherein the monomeric units represented by Formula I include monomeric units represented by Formula II:

##STR25##