Silicone-based hydrophilic copolymer and hydrogel compositions comprising the same

Patent metadata

Field	Value
Publication number	US-9851472-B2
Application number	US-201514670557-A
Country	US
Kind code	B2
Filing date	Mar 27, 2015
Priority date	Mar 27, 2015
Publication date	Dec 26, 2017
Grant date	Dec 26, 2017

Abstract

A hydrophilic siloxane copolymer of siloxane and hydrophilic organic monomer/s The copolymers can be functionalized to make them capable of undergoing further polymerization by thermal or actinic radiations. The hydrophilicity of these polymers can be varied by varying the siloxane versus organic monomer ratio thereby going from water dispersible to soluble states. The siloxane content can be tuned accordingly in order to provide moderate to high oxygen permeability. These copolymers can be used as a single component curable composition which results in hydrogels to minimize the presence of leachable components thus by reducing the processing cost. The polymers may also find applications in personal care formulations as copolymers, film-formers, hydrogels, coating, emulsions/latex etc.

First claim

What is claimed is:

1. A hydrophilic siloxane copolymer of the formula (1):
[W l A m B n C] p   (1)

wherein A and B are different, l is 1, m and n of formula (1) are independently 1-200, and 2<l+p<200;
W is a moiety having the general formula (2):
D-E-----  (2)

wherein E is a divalent moiety chosen from a substituted, un-substituted, aliphatic, aromatic, cyclic, or acyclic hydrocarbon radical having 1-20 carbon atoms, optionally containing sulfur or oxygen; D is a monovalent hydrocarbon radical with 1-10 carbon atoms with a functional group independently selected from a hydroxy, an ether, an ester, an amine, an amide, a carboxylic acid, or a combination of two or more thereof;
A is an organosilicone group-containing unit having the general formula (15):

wherein R 19 , R 20 , and R 21 are selected from hydrogen or a monovalent hydrocarbon radical with 1 to 10 carbon atoms optionally containing a heteroatom; and F is expressed as having the general structure of formula (16):

wherein R 22 , R 24 , and R 25 are independently chosen from hydrogen or a monovalent hydrocarbon radical with 1 to 5 carbon atoms optionally containing heteroatom; R 23 is chosen from a hydroxyl or an alkali metal salt thereof, an alkoxy, or a halogen; G is a divalent moiety independently chosen from a substituted or un-substituted, aliphatic or aromatic, cyclic or acyclic hydrocarbon radical having 1-20 carbon atoms optionally containing a heteroatom; H in formula (16) is defined by the general formula (17),

wherein I in formula (17) is an alkylene group with 1-16 carbon atoms; and
(i) when m in formula (17) is zero, M in formula (17) is not present and K is independently selected from:
a) CH 3 , —O—[Si(CH 3 ) 2 O] n —Si(CH 3 ) 3 , —OSi(CH 3 ) 3 ;
b)

c)

 and
d)

wherein R 26 and R 28 are a divalent hydrocarbon radicals with 1 to 5 carbon atoms, and R 27 is chosen from hydrogen or a monovalent hydrocarbon radical with 1 to 10 carbon atoms; wherein n in any in formulae (19) and (20) is an integer selected from 1-50;
and J and L are independently selected from CH 3 , —OSi(CH 3 ) 3 , or —O—[Si(CH 3 ) 2 O]n-Si(CH 3 ) 3 ; or

(ii) when m in formula (17) is greater than 0, J is CH 3 , K is +O—Si(CH 3 ) 2 —, L is —OSi(CH 3 ) 2 O, and M is —[OSi(CH 3 ) 2 ] n —, where n is an integer selected from 1-50;

B is a hydrophilic group-containing unit having the general formula (13)

wherein P in formula (13) is selected from O or NR 14 wherein R 14 is a hydrogen or monovalent hydrocarbon radical with 1 to 5 carbon atoms optionally containing a heteroatom; R 11 , R 12 and R 13 are independently selected from a hydrogen or monovalent hydrocarbon radical with 1 to 10 carbon atoms optionally containing a heteroatom; Q is a substituted or un-substituted, aliphatic, aromatic, cyclic, or acyclic hydrocarbon radical comprising of 1-50 carbon atoms, optionally containing a heteroatom, with a functional group independently selected from a hydroxyl, an ether, an ester, an amino, or a carboxylic acids; and
C in formula (1) is an organic group-containing unit having the general formula (14):

wherein R 15 , R 16 and R 17 are independently selected from a hydrogen or monovalent hydrocarbon radical with 1-10 carbon atoms; R in formula (14) is selected from O or NR 18 wherein R 18 is hydrogen or a monovalent hydrocarbon radical with 1 to 5 carbon atoms optionally containing a heteroatom; S is a divalent hydrocarbon radical with 1-20 carbon atoms chosen from a substituted or un-substituted aliphatic, cyclic, or aromatic hydrocarbon, optionally containing a heteroatom; and T is a monovalent hydrocarbon radical with 1-10 carbon atoms with a functional moiety chosen from a hydroxyl, an epoxy, an ether, an ester, an amine, an amide, or a carboxylic acid.

2. The copolymer of claim 1 wherein H in formula (16) has a formula (17a):

wherein R 39 is a methyl group or —O—Si(CH 3 ) 3 .

3. The copolymer of claim 1 wherein H in formula (16) has a formula (8a):

wherein R 40 is a linear or branched monovalent hydrocarbon radical with 1-50 carbon atoms.

4. The copolymer of claim 1 , wherein the ratio of m:n:p is from about 5-60:20-80:5-60, with the proviso that the total of the ratio adds up to 100.

5. A composition comprising a hydrophilic siloxane copolymer of the formula (1):
[W l A m B n C] p   (1)

wherein A and B are different, l is 1, m and n in formula (1) are independently 1-200, and 2<l+p<200;
W is a moiety having the general formula (2):
D-E------  (2)

wherein E is a divalent moiety chosen from substituted, un-substituted, aliphatic, aromatic, cyclic, or acyclic hydrocarbon radical having 1-20 carbon atoms, optionally containing sulfur or oxygen; D is a monovalent hydrocarbon radical with 1-10 carbon atoms with a functional group independently selected from a hydroxy, an ether, an ester, an amine, an amide, a carboxylic acid, or a combination of two or more thereof;
A is an organosilicone group-containing unit having the general formula (15):

wherein R 19 , R 20 , and R 21 are selected from hydrogen or a monovalent hydrocarbon radical with 1 to 10 carbon atoms optionally containing a heteroatom; and F is expressed as having the general structure of formula (16):

wherein R 22 , R 24 , and R 25 are independently chosen from hydrogen or a monovalent hydrocarbon radical with 1 to 5 carbon atoms optionally containing heteroatom; R 23 is chosen from a hydroxyl or an alkali metal salt thereof, an alkoxy, or a halogen; G is a divalent moiety independently chosen from a substituted or un-substituted, aliphatic or aromatic cyclic or acyclic hydrocarbon radical having 1-20 carbon atoms optionally containing a heteroatom; H in formula (16) is defined by the general formula (17),

wherein I in formula (17) is an alkylene group with 1-16 carbon atoms; and
(i) when m in formula (17) is zero, M in formula (17) is not present and K is independently selected from:
a) CH 3 , —O—[Si(CH 3 ) 2 O] n —Si(CH 3 ) 3 , —OSi(CH 3 ) 3 ;
b)

Assignees

• Naik Sandeep
• Bhat Shreedhar
• Shah Chetan
• Saxena Anubhav
• Mathad Raveendra
• Momentive Performance Mat Inc

Inventors

• Naik Sandeep
• Bhat Shreedhar
• Shah Chetan
• Saxena Anubhav
• Mathad Raveendra

Classifications

• C08F275/00

  Macromolecular compounds obtained by polymerising monomers on to polymers of monomers containing phosphorus, selenium, tellurium or a metal as defined in group C08F30/00 · CPC title

• C08F261/02

  on to polymers of unsaturated alcohols · CPC title

• C08L43/04

  Homopolymers or copolymers of monomers containing silicon · CPC title

• A61K8/90

  Block copolymers (A61K8/89 takes precedence) · CPC title

• G02B1/043 Primary

  Contact lenses · CPC title