Silicone polyether block copolymers having organofunctional endblocking groups

• US 8,013,097 B2
• Filed: 03/05/2008
• Issued: 09/06/2011
• Est. Priority Date: 04/11/2007
• Status: Expired due to Fees

• Current Assignee: Dow, Inc.
• Original Assignee: Dow, Inc.
• Inventors: Kennan, John, Vazquez, Fernando, Lewis, Kevin
• Primary Examiner(s): Loewe; Robert
• Application Number:
  US12/594,649
• Publication Number:
  US 20100048795A1
• Time in Patent Office: 1,280 Days
• Field of Search: None
• US Class Current: 528/25
• CPC Class Codes: C08G 77/388 containing nitrogen
• CPC Class Codes: C08G 77/46 containing polyether sequences
• CPC Class Codes: D06M 15/6436 containing amino groups
• CPC Class Codes: D06M 15/647 containing polyether sequences
• CPC Class Codes: D06M 2200/50 Modified hand or grip properties; Softening compositions

Abstract

Silicone polyether copolymers are disclosed having the average formula E-B-[AB]_n-E where E is an organofunctional endblocking group, B is a diorganopolysiloxane, A is a divalent organic group comprising at least one polyether group, and n is ≧1. The silicone polyether copolymers having an amine functional endblocking group are useful in the treatment of textiles and fibers.

Claims

1. A silicone polyether copolymer having the average formula;

E-B-[AB]_n-E

where E is an organofunctional endblocking group having the formula R^ACH₂CH(OH)CH₂OR², or

2. The silicone polyether copolymer of claim 1 wherein the silicone polyether copolymer has the average formula;

E-R₂SiO(R₂SiO)_xSiR₂—

[[R¹(C_mH_2mO)_yR<sup>−

1</sup>][R₂SiO(R₂SiO)_x]R₂Si]_n-E

x is ≧

0, m is from 2 to 4 inclusive, y is ≧

4, n is ≧

1,

R is independently a monovalent hydrocarbon group containing 1 to 30 carbons,

R¹ is a divalent hydrocarbon containing 2 to 30 carbons.

3. The silicone polyether copolymer of claim 1 wherein R^A has the formula (R³)₂N—

, H(R³)N—

, or (R³)₃N—

, wherein R³ is independently a monovalent organic containing 1 to 30 carbon atoms.

4. The silicone polyether copolymer of claim 3 wherein R^A is (CH₃CH₂)₂N—

.

5. The silicone polyether copolymer of claim 1 where the R^A amine functional group is a cyclic amine.

6. The silicone polyether copolymer of claim 5 where the cyclic amine is 1-(2-hydroxyethyl)piperazine.

7. The silicone polyether copolymer of claim 1 wherein the organofunctional endblocking group E has the formula R^QCH₂CH(OH)CH₂OR²—

where

R^Q is a monovalent quaternary ammonium functional group,

R² is a divalent hydrocarbon linking group containing 2 to 6 carbon atoms.

8. An emulsion comprising the silicone polyether block copolymer of claim 1.

9. A method comprising treating a textile or fibers with the emulsion of claim 8.

10. A method comprising treating a textile or fibers with the silicone block copolymer of claim 1.

11. A process to prepare a silicone polyether block copolymer comprising:

I) reacting;

A) a polyoxyalkylene having an unsaturated hydrocarbon group at each molecular terminal

B) a SiH terminated organopolysiloxane,

C) a hydrosilylation catalyst,

D) an optional solvent,

where the molar ratio of B/A is greater than one,

II) further reacting the product of step I with;

E) an epoxide having at least one aliphatic unsaturated hydrocarbon group

to form an epoxide terminal silicone polyether block copolymer,

III) reacting the epoxide terminal silicone polyether block copolymer with

F) an amine compound

to form an amine terminal silicone polyether block copolymer.

12. The process of claim 11 wherein A) the polyoxyalkylene has the average formula

H₂C═

C(R⁴)CH₂O(EO)_y′

(PO)_y″

CH₂C(R⁴)═

CH₂

wherein y′

is ≧

1, alternatively y′

is 0 to 60,

y″

is ≧

0, alternatively y″

is 0 to 60,

with the proviso that y′

+y″

≧

4

R⁴ is hydrogen or an alkyl group containing 1 to 20 carbon atoms,

EO is —

CH₂CH₂O—

,

PO is —

CH₂CH(Me)O—

or —

CH₂CH₂CH₂O—

.

13. The process of claim 11 wherein B) the SiH terminated organopolysiloxane has the average formula Me₂HSiO(Me₂SiO)_xSiHMe₂ where x is ≧

1.

14. The process of claim 13 wherein x ranges from 2 to 100.

15. The process of claim 11 wherein the epoxide is allyl glycidyl ether or vinylcyclohexene oxide.

16. The process of claim 11 wherein the amine compound is selected from diethylamine, N-methylethanolamine, or 1-(2-hydroxyethyl)piperazine.

17. The process of claim 11 further comprising;

IV) quaternizing the amine terminal silicone polyether block copolymer to form a quaternary ammonium salt terminal silicone polyether block copolymer.

18. The silicone polyether block copolymer prepared by the method according to claim 11.