Hydrophilic polysiloxane compositions

• US 6,013,711 A
• Filed: 06/09/1998
• Issued: 01/11/2000
• Est. Priority Date: 06/18/1997
• Status: Expired due to Term

• Current Assignee: General Electric Company
• Original Assignee: Ck Witco Corporation (Lanxess AG)
• Inventors: Lewis, Kenrick M., Yu, Hua
• Primary Examiner(s): Dawson, Robert
• Assistant Examiner(s): Robertson, Jeffrey B.
• Application Number:
  US09/093,941
• Time in Patent Office: 581 Days
• Field of Search: 528/15, 524/315, 524/265, 524/493, 524/773, 524/731, 524/730, 524/789
• US Class Current: 524/265
• CPC Class Codes: A61K 6/887 Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61K 6/896 Polyorganosilicon compounds
• CPC Class Codes: A61K 6/90 Compositions for taking dental impressions
• CPC Class Codes: C08G 77/12 containing silicon bound to hydrogen C08G77/045 takes precedence
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/46 containing polyether sequences
• CPC Class Codes: C08L 2666/34 Oxygen-containing compounds, including ammonium and metal salts
• CPC Class Codes: C08L 2666/54 Inorganic substances
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: C08L 83/00 Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 83/04 Polysiloxanes

Abstract

The instant invention provides a method for improving the miscibility of the lower molecular weight unsaturated siloxane-polyether copolymers with the α, ω-divinylpolysiloxanes without loss of storage stability, or delay of cure at the vulcanization temperature, or loss of permanent hydrophilicity or other desirable features of the cured polysiloxane. The compositions of the present invention comprise one or more α, ω-divinylpolysiloxanes, unsaturated polysiloxane-polyether copolymers having from 2 to 5 silicon atoms per molecule which are preferably trisiloxanes, and a compatibilizing additive. The permanently hydrophilic, rapidly wettable polysiloxane compositions yield static water contact angles <50° dynamic advancing contact angles of less than about 100.

Claims

1. A composition comprising a first component comprising:

(a) a polydiorganosiloxane that contains at least two hydrosilylatable unsaturated hydrocarbon groups per molecule;

(b) an effective amount of hydrosilylation catalyst;

(c) a hydrophilic, unsaturated polysiloxane-polyether copolymer having from 2 to 5 silicon atoms, at least one aliphatic unsaturation and at least one-polyether functionality; and

(d) a compatibilizing additive.

2. A composition according to claim 1 wherein component (c) is selected from the group consisting of:

(A) R¹ --SiR₂ O(SiR₂ --O)_p --(SiR² Z--O)_m --SiR₂ R¹

(B) R¹ --SiR₂ O(SiR₂ --O)_p --(SiR² Z--O)_m --SiR₃

(C) R₃ SiO(SiR₂ --O)_p --(SiR² Z--O)_m--(SiR² R¹ --O)_q --SiR₃

(D) R¹ --R₂ SiO(SiR₂ --O)_p --(SiR² Z--O)_m --(SiR² R¹ --O)_q --SiR₃

(E) R¹ --R₂ SiO(SiR₂ --O)_p --(SiR² Z--O)_m --(SiR² R¹ --O)_q --SiR₂ R¹

(F) Z--SiR₂ O(SiR₂ --O)_p --(SiR² R¹ --O)_q --SiR₂ R¹

(G) [Z--SiR₂ O(SiR₂ --O)_p ]_r --(SiR₂ --O)--(SiR² R¹ --O)_q --SiR₂ R¹

(H) (R₂ Si--O)_p --(SiR² Z--O)_m --(SiR² R¹ --O)_q

(I) R¹ Si[(O--SiR₂)_p --Z]₃

(J) RSi[(O--SiR² R¹)_q --(O--SiR₂)_p --Z]₃ ; and

(K) [R¹ SiR₂ O(SiR₂ --O)_p ]_v --(SiO₂)[(O--SiR² R¹)_q (O--SiR₂ Z)_m ]_4-v

wherein R is a C₁ -C₂₀, saturated, monovalent organic group;

R¹ is a C₁ -C₂₀, unsaturated monovalent organic group that can be hydrosilylated to yield silicon-carbon bonds;

R² may be the same as R or as R¹ ;

m, p, q, r and v are chosen such that the total number of silicon atoms per molecule is 2 to 5 inclusive with the proviso that there is at least one Z and at least one R¹ per molecule and r and v are values from 0 to 1,3≧

m>

0, and 0≦

q and p≦

3; and

Z is a polyether-containing group that is linked to the polysiloxane block by a silicon-carbon bond.

3. A composition according to claim 2 wherein Z has general formula of the type,

--C_x H_2x O(C_a H_2a O)_b R" and --C_x H_2x OG[(C_a H_2a O)_b R"]_z

wherein x is an integer in the range 1-20, a is an integer having a value greater than or equal to 2, G is a polyhydroxy group capable of being alkoxylated;

z is the valency of G, R" is hydrogen or a polyether capping group, an alkyl group of 1-8 carbon atoms, or an acyl group of 1-8 carbon atoms, or a vinyl ether or an organosilyl group.

4. A composition according to claim 3 wherein component (c) is selected from the group consisting of:

H₂ C═

CHSi(CH₃)₂ --O--Si(CH₃)Z--O--Si(CH₃)₂ CH═

CH₂ ;

H₂ C═

CHSi(CH₃)₂ --O--Si(CH₃)Z--O--Si(CH₃)₃ ;

H₂ C═

CHSi(CH₃)₂ --O--Si(CH₃)Z--O--Si(CH₃)₂ CH═

CH₂ ;

H₂ C═

CHSi(CH₃)₂ --O--[Si(CH₃)₂ O]₂ --[Si(CH₃)Z--O]--Si(CH₃)₂ CH═

CH₂ ; and

H₂ C═

CHSi(CH₃)₂ --O--[Si(CH₃)₂ O]--[Si(CH₃)Z--O]₂ --Si(CH₃)₂ CH═

CH₂ ;

wherein

Z=--(CH₂)₃ O(C₂ H₄ O)₇.5 CH₃ or (CH₂)₃ O(C₂ H₄ O)₅ (C₃ H₆ O)₂ H or --(CH₂)₃ O(C₂ H₄ O)₃ CH₃ or

HO(C₂ H₄ O)(CH₂ C--CHCH₂)(OC₂ H₄)OH.

5. A composition according to claim 1 wherein the first component additionally comprises a rheology modifier.

6. A composition according to claim 1 wherein the compatabilizing additive is selected from the group consisting of:

a hydrocarbon ester with solubility parameter, δ

,=13-17 MPa1/2, or a polysiloxane-polyether copolymer, or a hydrophobic or hydrophilic filler with surface area greater than 100 square meters per gram and median particle size smaller than 20 nanometers.

7. A composition according to claim 1 additionally comprising a separate, second part which comprises:

(a) a polyorganohydridosiloxane crosslinker that contains at least three SiH bonds per molecule, and

(b) a polydiorganosiloxane that contains at least two hydrosilylatable unsaturated hydrocarbon groups per molecule.

8. The reaction product according to claim 7 wherein the first and second components are combined and allowed to react.

9. A composition according to claim 7 wherein the second component additionally comprises a polyorganohydridosiloxane chain extender with terminal SiH groups.

10. The process of combining the first and second components of claim 7.