IP Library Granted Patent US 8,916,511
Granted Patent B2
US 8,916,511 · App. 13/389,854 · Granted Dec 23, 2014

Polysiloxanes having quaternary ammonium groups and use thereof

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Quick Facts
Patent No.
US 8,916,511
App. No.
13/389,854
Granted
Dec 23, 2014
Kind
B2
Abstract

The invention relates to a novel branched polysiloxanes having quaternary ammonium groups of the general formula (I) as a softening agent for textile sheet materials and fibers, and to a method for the production and use thereof M a M Q b M R c D d D Q e D R f T g Q h Formula (I).

Claims (54)

1. A branched organomodified polysiloxane comprising more than three quaternary ammonium groups and having formula I:

M a M Q b D d D Q e T g Q h   (I),

wherein

M is R 1 3 SiO 1/2 , and a is 0 to 40,

M Q is R 2 R 1 2 SiO 1/2 , and b is 0 to 44,

D is R 1 2 SiO 2/2 , and d is 20 to 1000,

D Q is R 2 R 1 SiO 2/2 , and e is 0 to 50,

T is R 1 SiO 3/2 , and g is 0 to 20,

Q is SiO 4/2 , and h is 0 to 20,

each R 1 is independently a linear or branched alkyl, aryl, or alkaryl moiety comprising 1 to 30 carbon atoms,

each R 2 is independently an organic moiety comprising an ammonium function,

wherein a sum of g and h is greater than 1, a sum of b and e is not less than 3, and a sum of a and b is greater than 3.

2. The polysiloxane of claim 1 , wherein a sum of g and h is greater than 2.

3. The polysiloxane of claim 1 , wherein R 2 is a moiety of formula II:

—R 4 —R 5   (II),

wherein

each R 4 is independently a divalent organic moiety,

each R 5 is independently a moiety selected from the group consisting of:

wherein

each A − is independently a counter-ion to the positive charge on the quaternary nitrogen group,

each R 6 is independently an alkyl moiety comprising 1 to 30 carbon atoms,

m is 2 to 12,

each R 7 is independently a saturated or unsaturated, branched or unbranched alkyl moiety comprising 1 to 30 carbon atoms,

each R 8 is independently O, NH, or NR 6 ,

each R 9 is independently at least one selected from the group consisting of a branched divalent hydrocarbon moiety and an unbranched divalent hydrocarbon moiety,

each R 10 is independently a polyether moiety, and

each R 11 is independently —COR 1 , R 1 , or H.

4. The polysiloxane of claim 3 , wherein each R 4 is independently a moiety selected from the group consisting of:

5. The polysiloxane of claim 3 , wherein R 10 is a polyether moiety of formula III:

—[CH 2 CH 2 O] n [CH 2 CH(CH 3 )O] 0 [CH(CH 3 )CH 2 O] p R 11   (III),

wherein

n, o, p are each independently from 0 to 100, provided n+o>1.

6. The polysiloxane of claim 1 , wherein a sum of g and h is not less than 2 and h is not less than 1.

7. The polysiloxane of claim 1 , wherein a sum of a and b is not less than 4.

8. A process for preparing the branched polysiloxane of claim 1 , the process comprising:

a) equilibrating a tri-alkoxysilane or tetraalkoxysilane with a cyclic siloxane and an α, ω-SiH siloxane, and hydrolyzing the alkoxy groups in the presence of water, to obtain a first branched SiH-functional siloxane;

b) subsequently, condensating the first branched SiH-functional siloxane, to obtain a second SiH-functional silioxane;

c) hydrosilylating the second branched SiH functional siloxane with an epoxide comprising a double bond, to obtain an epoxy-functional siloxane;

d) reacting the epoxy-functional siloxane with a tertiary amine, to form the branched polysiloxane.

9. A process for softening at least one material selected from the group consisting of a sheet material and a fiber, the process comprising:

contacting the compound of claim 1 with the at least one material.

10. A process for softening at least one material selected from the group consisting of a sheet material and a fiber, the process comprising:

contacting the polysiloxane of claim 1 , wherein d is 20 to 1000, with the material,

wherein the sheet material is at least one textile sheet material selected from the group consisting of a woven, a knit, and a nonwoven, and

the fiber is at least one selected from the group consisting of tissue (paper fiber), a fiber formed from at least one selected from the group consisting of a natural material, and a synthetic raw material, and leather.

11. A concentrate, comprising:

about 90% to 100% by weight of the polysiloxane of claim 1 .

12. An emulsion concentrate comprising:

50% to 90% by weight of the polysiloxane of claim 1 .

13. A formulation, comprising:

5% to 20% by weight of the polysiloxane of claim 1 .

14. An aqueous emulsion, comprising:

5 to 20% by weight of the polysiloxane of claim 1 .

15. The polysiloxane of claim 2 , wherein a sum of g and h is not less than 2 and h is not less than 1.

Assignments (2)
MERGER Recorded May 15, 2014
From: EVONIK GOLDSCHMIDT GMBH
To: EVONIK DEGUSSA GMBH
Reel/Frame 032900/0372 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 16, 2012
From: MAURER, TOBIAS; FERENZ, MICHAEL
To: EVONIK GOLDSCHMIDT GMBH
Reel/Frame 027716/0033 →