Silicone-based hydrophilic copolymer and hydrogel compositions comprising the same

Patent metadata

Field	Value
Publication number	US-10795058-B2
Application number	US-201715851824-A
Country	US
Kind code	B2
Filing date	Dec 22, 2017
Priority date	Mar 27, 2015
Publication date	Oct 6, 2020
Grant date	Oct 6, 2020

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 formula (1):

wherein A and B are different, 1 of formula (1) is 1, m and n of formula (1) are independently 1-200, and 2<(1+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 (3):

wherein R 1 , R 2 , and R 3 are independently selected from a hydrogen or monovalent hydrocarbon radical with 1 to 10 carbon atoms optionally containing a heteroatom; and
wherein F is a siloxane-containing group chosen from a compound of the formula (4)-(9):

wherein R′ is independently chosen from H or CH 3 ; R″ is independently chosen from a hydrocarbon radical with 1-20 carbon atoms chosen from a substituted or un-substituted aliphatic, cyclic, or aromatic hydrocarbon, which may contain a heteroatom, m in formulas (5)-(9) is an integer from 0-1, and m in formula (4) is 1; X is a functional group independently chosen from an ester or an amide; when m in formulas (5)-(9) is 0, K is independently selected from CH 3 , —O—[Si(CH 3 ) 2 O]n-Si(CH 3 ) 3 , —OSi(CH 3 ) 3 ;

wherein R 8 and R 10 are independently selected from a divalent hydrocarbon radical with 1 to 5 carbon atoms and R 9 is selected from a hydrogen or monovalent hydrocarbon radical with 1 to 10 carbon atoms; n is an integer selected from 1-10; J and L are independently chosen from CH 3 , —OSi(CH 3 ) 3 , —O—[Si(CH 3 ) 2 O]n-Si(CH 3 ) 3 ; and when m 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 —;
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 hydrogen or a 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 amine, or a carboxylic acid; 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 a hydrogen or 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 D and T are independently selected from OR 29 , NR 30 R 31 , or CR 32 R 33 R 34 O—, where R 29 , R 30 , R 31 , R 32 , R 33 , and R 34 can be selected from hydrogen or a monovalent hydrocarbon radical with 1 to 5 carbon atoms.

3. The copolymer of claim 1 wherein D and at least one T is selected as U, and U has the general formula (21)

where V is selected from —O— or NR 38 ; R 35 , R 36 , R 37 , and R 38 is independently selected from a hydrogen or monovalent hydrocarbon radical with 1 to 5 carbon atoms; Y is selected from a divalent, substituted or un-substituted, aliphatic hydrocarbon radical with 1-10 carbon atoms optionally containing a heteroatom.

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):

wherein 1 is 1, m and n are independently 1-200, and 2<1+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 block having the general formula (3):

wherein R 1 , R 2 , and R 3 are independently selected from a hydrogen or monovalent hydrocarbon radical with 1 to 10 carbon atoms optionally containing a heteroatom; and F is a siloxane-containing block chosen from a siloxane-containing compound of the formula:

wherein, R′ is independently chosen from H or CH 3 ; R″ is independently chosen from a hydrocarbon radical with 1-20 carbon atoms chosen from a substituted or un-substituted aliphatic, cyclic, or aromatic hydrocarbon, which may contain a heteroatom, m in formulas (5)-(9) is an integer from 0-1, and m in formula (4) is 1; X is a functional group independently chosen from an ester or an amide; when m in formulas (5)-(9) is 0, K is independently selected from CH 3 , —O—[Si(CH 3 ) 2 O]n-Si(CH 3 ) 3 , —OSi(CH 3 ) 3

wherein R 8 and R 10 are selected from a divalent hydrocarbon radical with 1 to 5 carbon atoms and R 9 is selected from hydrogen or monovalent hydrocarbon radical with 1 to 10 carbon atoms wherein n is an integer selected from 1-10; J and L are independently chosen from CH 3 , —OSi(CH 3 ) 3 , —O—[Si(CH 3 ) 2 O]n-Si(CH 3 ) 3 ; and when m is greater than 1, 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 —;
B is a hydrophilic block having the general formula (13)

wherein P 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 fr

Assignees

• Momentive Performance Mat Inc

Inventors

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

Classifications

• C08F261/02

  on to polymers of unsaturated alcohols · CPC title

• A61Q19/00

  Preparations for care of the skin · CPC title

• G02B1/043 Primary

  Contact lenses · CPC title

• C08L43/04

  Homopolymers or copolymers of monomers containing silicon · CPC title

• 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