Organo-modified silicone polymers

• US 9,944,742 B2
• Filed: 09/22/2014
• Issued: 04/17/2018
• Est. Priority Date: 03/22/2012
• Status: Active Grant

• Current Assignee: Momentive Performance Materials Incorporated
• Original Assignee: Momentive Performance Materials Incorporated
• Inventors: Saxena, Anubhav, Naik, Sandeep Shashikant, Phukan, Monjit, Bhat, Shreedhar
• Primary Examiner(s): Bakshi, Pancham
• Application Number:
  US14/492,378
• Publication Number:
  US 20150011788A1
• Time in Patent Office: 1,303 Days
• Field of Search: 556418, 556437
• CPC Class Codes: C07F 7/1804 Compounds having Si-O-C linkages Si-O-acyl linkages C07F7/1896
• CPC Class Codes: C07F 7/21 Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
• CPC Class Codes: C08F 230/08 containing silicon
• CPC Class Codes: C08F 283/124 on to polysiloxanes having carbon-to-carbon double bonds
• CPC Class Codes: C08G 2210/00 Compositions for preparing hydrogels
• CPC Class Codes: C08G 77/38 Polysiloxanes modified by chemical after-treatment C08G77/045 takes precedence
• CPC Class Codes: C08G 77/48 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms C08G77/42 takes precedence
• CPC Class Codes: C08G 77/50 by carbon linkages C08G77/485 takes precedence
• CPC Class Codes: C08K 3/20 Oxides; Hydroxides graphene oxides C08K3/042
• CPC Class Codes: C08L 101/14 the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
• CPC Class Codes: C08L 71/00 Compositions of polyethers obtained by reactions forming an ether link in the main chain of polyacetals C08L59/00; of epoxy resins C08L63/00; of polythioether-ethers C08L81/02; of polyether-sulfones C08L81/06; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: C08L 83/14 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms C08L83/10 takes precedence
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: G02B 2207/109 Sols, gels, sol-gel materials

Abstract

A linear silicone polymer suitable for use in producing homopolymers, copolymers, polymerized emulsions, latex compositions, and hydrogel polymer films. In one aspect, a hydrophilic silicone monomer is of the Formula 1:
WA_mB_nW  (1)
Where, A is a divalent block comprising a silicone-containing pendant group. In one embodiment, the silicone-containing pendant group comprises polyalkylene oxide groups. The structure of the polymer can be controlled and tuned to provide a material with excellent wettability and oxygen permeability. The polymers are suitable for use in a variety of applications including in providing a film for forming contact lenses.

Claims

1. A linear polymer of the formula:

WA_mB_nW

where m is a positive integer from 2-100, and n is a positive integer from 0-100;

A is a divalent block having a general formula;

2. The polymer of claim 1, wherein L is a polyalkyleneoxide residue.

3. The polymer of claim 1, wherein L is a polyalkyleneoxide which is —

CH₂CH₂O—

, —

CH₂CH(CH₃)O—

, —

CH₂CH₂CH₂O—

, or their analogues with up to 6 carbon atoms.

4. The polymer of claim 1, wherein L is a cyclic hydrocarbon residue with the structure:

5. The polymer of claim 1, wherein R₉, R₁₀, R₁₁, R₁₃, R₁₄, R₁₅, R₁₆, R₁₈, and R₂₀ in the unit G of group E are independently a hydrocarbon radical selected from the group consisting of methyl, ethyl, propyl, iso-propyl, butyl, isobutyl, phenyl, naphthyl, and aralkyl radical with 8 to 20 carbon atoms, trifluoromethylpropyl, and combinations of two or more thereof.

6. The polymer of claim 1, wherein the mono-functional group E has a structure which is of the formula:

7. The polymer of claim 1, where R₂₅ and R₂₆ are hydrogen, R₂₇ is hydrogen or a methyl radical, and R₂₈ is a part of an ethylenically-unsaturated hydrophilic monomer or a hydrophobic monomer.

8. The polymer of claim 1 having at least one W which is an X group to yield a pre-polymer.

9. The polymer of claim 1, wherein both the W groups are a Y group as a chain stopper to yield a non-reactive polymer.

10. A homo or co-polymer comprising at least one pre-polymer of claim 8.

11. The copolymer of claim 10, wherein the polymer is a copolymer further comprising a free-radical polymerizable organic monomer chosen from the group consisting of a vinylic monomer, an acrylide monomer, an acrylic monomer, or a combination of two or more thereof.

12. The copolymer of claim 11, wherein the vinylic monomer is selected from the group consisting of N-vinyl-pyrrolidone, N-vinyl-caprolactam, N-vinyl-acetamide, N-vinyl-formamide, N-vinyl-isopropylamide, vinyl benzene, vinyl naphthalene, vinyl pyridine, vinyl alcohol, vinyl containing silicone, or a combination of two or more thereof.

13. The copolymer of claim 11, wherein the acrylic monomers are selected from the group consisting of 2 hydroxy-ethyl-methacrylate (HEMA), 2-hydroxy-ethyl-acrylate (HEA), hydroxyl propyl methacrylate, trimethylammonium 2-hydroxy propyl methacrylate hydrochloride, dimethylaminoethyl methacrylate, glycerol methacrylate, N,N-Dimethylacrylamide, N-isopropylacrylamide, acrylamide, methacrylamide, acrylic acid, methacrylic acid, acrylated hydrophilic or hydrophobic organo-silicones, or combinations of two or more thereof.

14. The polymer according to claim 10 where the polymer is a hydrogel film.

15. A film forming additive comprising the polymer of claim 10 in the form of emulsion or latex.

16. The siloxane of claim 1, wherein the polymer is a film forming additive in a textile, a paper, a leather, a personal care, a health care, a home care, a coating, a painting, or a seed treatment formulation.