α,ω-functionalized polyoxyalkylene-siloxane polymers and copolymers made therefrom

Patent metadata

Field	Value
Publication number	US-9428617-B2
Application number	US-201514858169-A
Country	US
Kind code	B2
Filing date	Sep 18, 2015
Priority date	Sep 18, 2014
Publication date	Aug 30, 2016
Grant date	Aug 30, 2016

Abstract

An α,ω-functionalized polyoxyalkylene-siloxane polymer having the general structural Formula (I):

provides improved hydrophilicity and hemocompatibility. The α,ω-functionalized polyoxyalkylene-siloxane polymer may be used to make various polycarbonate/α,ω-functionalized polyoxyalkylene-siloxane copolymers and polymer blends, as well as articles including such copolymers and blends.

First claim

What is claimed is:

1. An α,ω-functionalized polyoxyalkylene-siloxane polymers having the structural Formula (I):

wherein each R 1 , R 2 and R 3 is independently a linear or branched aliphatic group containing from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group containing 6 to 16 carbon atoms, an alicyclic group containing 3 to 16 carbon atoms, a heteronuclear aromatic group containing 3 to 16 carbon atoms, a hydrocarbyl group having from 3 to 16 carbon atoms and containing at least one heteroatom of oxygen, nitrogen or sulfur and/or containing at least one ester, nitrile or halo group, wherein at least one R 2 is different from at least one R 3 ;
R 12 is independently hydrogen or methyl;
A is

wherein R 4 is independently a divalent linear or branched alkylene group having from 2 to 10 carbon atoms, an aralkylene group having from 8 to 12 carbon atoms, an unsubstituted or substituted arylene group having from 8 to 18 carbon atoms, or a hydrocarbylene group having from 2 to 10 carbon atoms and containing at least one oxygen heteroatom, R 5 is independently a hydrogen, a halogen, an aliphatic group containing from 1 to 12 carbon atoms, an aromatic group containing from 6 to 12 carbon atoms, an alkoxy group containing form 1 to 12 carbon atoms or an aryloxy group containing from 6 to 12 carbon atoms, R 6 is independently a hydroxyl group, an amine group, a carboxylic acid chloride group or a sulfonyl halide group, and p is 1;
wherein m, n, n′, x and y are integers, and wherein m is from 0 to 120, n is from 1 to 120, n′ is from 1 to 10, x is from 1 to 300, and y is from 0 to 100, with the proviso that the sum of n+m is greater than or equal to 2.

2. The α,ω-functionalized polyoxyalkylene-siloxane polymer of claim 1 , wherein R 1 is independently an alkyl group of from 1 to 4 carbon atoms or phenyl; R 2 is independently an alkyl group of from 1 to 4 carbon atoms or phenyl; R 3 is independently an alkyl group of from 1 to 16 carbon atoms, phenyl, 2-phenylethyl, 2,2-diphenylethyl, 2-phenyl-2-methylethyl, 3-phenylpropyl, 3-phenyl-2-methylpropyl, or phenyl-4-oxabutyl; R 4 is independently an alkylene group of 2 to 6 carbon atoms; R 5 is independently hydrogen, chloro, methoxy, ethoxy; R 6 is independently —OH, —NH 2 or —C(═O)Cl; R 12 is methyl; wherein m, n, n′, p, x and y are integers, and wherein m is from 0 to 100; n is from 1 to 100; n′ is from 1 to 6; p is 1; x is from 1 to 275; and y is from 0 to 80.

3. The α,ω-functionalized polyoxyalkylene-siloxane polymer of claim 2 , wherein R 1 is methyl; R 2 is methyl, R 3 is independently methyl or phenyl; R 4 is —CH 2 CH 2 —, —CH(CH 3 )CH 2 —, —CH 2 CH 2 CH 2 — or —CH 2 CH(CH 3 )CH 2 —; R 5 is independently hydrogen or methoxy; R 6 is —OH; wherein m, n, n′, p, x and y are integers, and wherein m is from 0 to 100; n is from 1 to 100; n′ is from 1 to 3; p is 1; x is from 1 to 275; and y is from 0 to 80.

4. A composition comprising an α,ω-functionalized polyoxyalkylene-siloxane polymer of claim 1 and at least one polymer selected from the group consisting of polycarbonate homopolymers, polycarbonate copolymers, polycarbonate-polyesters, polyesters, polysulfones, polyethersulfones, polyetheretherketones, polyimides and polyetherimides and combinations thereof.

5. An article comprising the composition of claim 4 , wherein the article is one or more of a medical article, a medical tube, a medical bag, a mobile phone housing, a frozen food service equipment article, a helmet, an automotive windshield, a motorcycle windshield, an automotive sunroof, a dashboard, a headlamp, or an electric screen.

6. A method of making an article comprising molding, shaping, or forming the composition of claim 4 into the article.

7. A method preparing an α,ω-functionalized polyoxyalkylene-siloxane polymers having the structural Formula (I):

wherein each R 1 , R 2 and R 3 is independently a linear or branched aliphatic group containing from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group containing 6 to 16 carbon atoms, an alicyclic group containing 3 to 16 carbon atoms, a heteronuclear aromatic group containing 3 to 16 carbon atoms, a hydrocarbyl group having from 3 to 16 carbon atoms and containing at least one heteroatom of oxygen, nitrogen or sulfur and/or containing at least one ester, nitrile or halo group, wherein at least one R 2 is different from at least one R 3 ;
R 12 is independently hydrogen or methyl;
A is

wherein R 4 is independently a divalent linear or branched alkylene group having from 2 to 10 carbon atoms, an aralkylene group having from 8 to 12 carbon atoms, an unsubstituted or substituted arylene group having from 8 to 18 carbon atoms, or a hydrocarbylene group having from 2 to 10 carbon atoms and containing at least one oxygen heteroatom, R 5 is independently a hydrogen, a halogen, an aliphatic group containing from 1 to 12 carbon atoms, an aromatic group containing from 6 to 12 carbon atoms, an alkoxy group containing form 1 to 12 carbon atoms or an aryloxy group containing from 6 to 12 carbon atoms, R 6 is independently a hydroxyl group, an amine group, a carboxylic acid chloride group or a sulfonyl halide group, and p 1;
wherein m, n, n′, x and y are integers, and wherein m is from 0 to 120, n is from 1 to 120, n′ is from 1 to 10, x is from 1 to 300, and y is from 0 to 100, with the proviso that the sum of n+m is greater than or equal to 2, comprising:
(a) reacting a hydride terminated siloxane represented by the structural Formula (IV):

wherein each R 1 , R 2 and R 3 is independently a linear or branched aliphatic group containing from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group containing 6 to 16 carbon atoms, an alicyclic group containing 3 to 16 carbon atoms, a heteronuclear aromatic group containing 3 to 16 carbon atoms, a hydrocarbyl group having from 3 to 16 carbon atoms and containing at least one heteroatom of oxygen, nitrogen or sulfur and/or containing at least one ester, nitrile or halo group, wherein at least one R 2 is different from at least one R 3 ; and x is an integer from 1 to 300 and y is an integer from 0 to 100 with bis-unsaturated polyalkylene containing terminal carbon-carbon double bonds in the presence of a hydrosilylation catalyst to obtain hydride terminated polyoxyalkylene siloxane represented by the structural Formula (V):

wherein each R 1 , R 2 and R 3 is independently a linear or branched aliphatic group containing from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group containing 6 to 16 carbon atoms, an alicyclic group containing 3 to 16 carbon atoms, a heteronuclear aromatic group containing 3 to 16 carbon atoms, a hydrocarbyl group having from 3 to 16 carbon atoms and containing at least one heteroatom of oxygen, nitrogen or sulfur and/or containing at least one ester, nitrile or halo group, wherein R 2 and R 3 are not the same;
R 12 is independently hydrogen or methyl;
wherein m, n, n′, x and y are integers, and wherein m is from 0 to 120, n is from 1 to 120, n′ is from 1 to 10, x is from 1 to 300, and y is from 0 to 100, with the proviso that the sum of n+

Assignees

• Momentive Performance Mat Inc
• Momentive Performance Mat Inc

Inventors

• Mittal Anuj
• Samantara Laxmi
• Alam Samim
• Saxena Anubhav
• Ramakrishnan Indumathi
• Rojas-Wahl Roy U

Classifications

• C08L83/12

  containing polyether sequences · CPC title

• C08G77/448

  containing polycarbonate sequences · CPC title

• C08L69/00

  Compositions of polycarbonates; Compositions of derivatives of polycarbonates · CPC title

• C08G77/70

  Siloxanes defined by use of the MDTQ nomenclature · CPC title

• C08L83/10

  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 title