Block-modified polysiloxanes and compositions formed thereof

Patent metadata

Field	Value
Publication number	US-11746193-B2
Application number	US-201817292168-A
Country	US
Kind code	B2
Filing date	Nov 20, 2018
Priority date	Nov 20, 2018
Publication date	Sep 5, 2023
Grant date	Sep 5, 2023

Abstract

Block-modified polysiloxanes and compositions comprising the block-modified polysiloxanes are useful in the field of textile finishing. Emulsions comprising the compositions have a very small and narrowly distributed particle size which increases penetration, and provide good softening properties coupled with good hydrophilicity.

First claim

What is claimed is:

1. A block-modified polysiloxane, which is a linear or cyclic polysiloxane copolymer and comprises repeating structural units having the following structural formula (1):

where X is a divalent hydrocarbon radical having at least 3 carbon atoms, which contains at least one hydroxyl group and is interrupted by an oxygen atom, and the X groups in the repeating units are the same or different;
M is a divalent hydrocarbon radical of the formula C a H 2a , where a is a positive integer between 1 and 10, and the M groups in the repeating units are the same or different;
N is a nitrogen atom;
m is a positive integer between 10 and 200;
n is a positive integer, between 50 and 350;
Me denotes methyl;
R 1 , R 2 , R 3 and R 4 are the same or different, and are each independently an alkyl group having from 1 to 4 carbon atoms or a benzyl group or H;
R 5 and R 6 are the same or different, and are each independently H, or an alkyl group having from 1 to 20 carbon atoms, which are optionally substituted by oxygen atoms;
A − is an inorganic or organic anion.

2. The block modified polysiloxane of claim 1 , wherein
M is a divalent hydrocarbon radical, or C a H 2a , where a is a positive integer between 2 and 4, and the M groups in the repeating units are the same or different;
m is a positive integer between 20 and 150, and
n is a positive integer between 70 and 300.

3. A block-modified linear or cyclic polysiloxane copolymer, which contains repeating structural units having the following structural formulae (3) and/or (4):

where Y is the structure —B-[EO] v [PO] w —,
where EO is ethylene oxide and PO is propylene oxide;
B is a linear or branched C1-C6 alkylene group;
v is a positive integer of ≥200;
w is a positive integer of 200;
v+w≥1;
v/w is between 1.1 and 5;
where X is a divalent hydrocarbon radical having at least 3 carbon atoms, which contains at least one hydroxyl group and is interrupted by an oxygen atom, and the X groups in the repeating units are the same or different;
M is a divalent hydrocarbon radical of the formula C 2 H 2a , where a is a positive integer between 1 and 10, and the M groups in the repeating units are the same or different;
N is a nitrogen atom;
m is a positive integer between 10 and 200;
n is a positive integer, between 50 and 350;
Me denotes methyl;
R 1 , R 2 , R 3 and R 4 are the same or different, and are each independently an alkyl group having from 1 to 4 carbon atoms or a benzyl group or H;
R 5 are the same or different, and are each independently H, or an alkyl group having from 1 to 20 carbon atoms, which are optionally substituted by oxygen atoms;
R 6 and R 7 are the same or different, and are each independently H, or an alkyl group having from 1 to 20 carbon atoms;
A − is an inorganic or organic anion.

4. The block-modified polysiloxane of claim 3 , wherein X is a ring opened epoxide selected from the group consisting of
(C a H 2a O) b —CH(CH 2 OH) (CH 2 ) f CH(CH 2 OH)—
(C a H 2a O) b —CH 2 CH(OH) (CH 2 ) f CH(CH 2 OH)—,
(C a H 2a O) b —(CH 2 ) f OCH 2 CH(OH)CH 2 —,
(C a H 2a O) b —(CH 2 ) f OCH 2 CH(CH 2 (OH))—,
and mixtures thereof,
where a are the same or different, and are integers between 2 and 4; b is the same or different, and is an integer between 0 and 100; f is an integer between 2 and 6.

5. The block-modified linear or cyclic polysiloxane copolymer of claim 3 prepared by a reaction of a mixture of raw materials comprising:
(A) an epoxy-functional silicone oil;
(B) a polyetheramine; and
(C) an aminoalkylsilicone oil.

6. The composition of claim 5 , wherein the epoxy-functional silicone oil (A) is a polydimethylsiloxane terminated at both ends with an epoxy-functional group.

7. The composition of claim 5 , wherein the epoxyalkyl silicone oil (A) is a polydimethylsiloxane terminated at both ends with an epoxy-functional group having the following structural formula (5):

where
n is a positive integer, between 50 and 350;
Me denotes methyl; and
Epoxy is selected from the group consisting of
(C a H 2a O) b —(CH 2 ) f OCH 2 CHOCH 2
where a is an integer between 2 and 4; b can be the same or different, and is an integer between 0 and 100; f is an integer between 2 and 6;
ω-(3,4-epoxycyclohexyl)alkylene,
β-(3,4-epoxycyclohexyl)ethylene,
β-(3,4-epoxycyclohexyl)-O-methyl ethylene,
β(3,4-epoxy-4-methylcyclohexyl)-β-methyl ethylene, and mixtures thereof.

8. The composition of claim 5 , wherein the polyetheramine (B) is a substance having the structural formula NR a —B-[EO] v [PO] w —NR a , where
v is a number between 0 and 200,
w is a number between 0 and 200
B is a linear or branched C2-C6 alkylene group;
R are the same or different, and is independently H, or an alkyl group having from 1 to 6 carbon atoms;
each a is the same or different, and is an integer between 1 and 4.

9. The composition of claim 8 , wherein the aminoalkyl silicone oil (C) is a di-aminoalkyl-terminated polydimethylsiloxane.

10. The composition of claim 8 , wherein the aminoalkyl silicone oil (C) is a di-3-aminopropyl-terminated polydimethylsiloxane having the structural formula (6):

M is a divalent hydrocarbon radical, or C a H 2a , where a is a positive integer between 1 and 10, and the M groups in the repeating units can be the same or different;
R 1 , R 2 , R 3 and R 4 are the same or different, and are each independently an alkyl group having from 1 to 4 carbon atoms or a benzyl group or H;
m is a positive integer between 10 and 200; and
Me denotes methyl.

11. The block-modified polysiloxane of claim 3 , wherein a content of unopened epoxide groups is less than 0.05 mmol/g, measured by nuclear magnetic resonance (NMR).

12. The block-modified polysiloxane of claim 3 , which have an amine value of from 0.01 to 0.5 meq/g, measured by nuclear magnetic resonance (NMR).

13. The composition of claim 5 , wherein the molar ratio of the epoxide groups in epoxyalkyl silicone oil (A), to the amino-functional groups in polyetheramine (B), ranges from 1.01 to 2.

14. The composition of claim 5 , wherein the molar ratio of the epoxide groups in epoxyalkyl silicone oil (A), to the amino-functional groups in aminoalkyl silicone oil (C), ranges from 1 to 5.

15. The composition of claim 5 , wherein the weight ratio of Component (B), based on the total weight of epoxyalkyl silicone oil (A), polyetheramine (B), and aminoalkyl silicone oil (C), ranges from 1 to 15 wt %.

16. The composition of claim 5 , wherein the weight ratio of Component (C), based on the total weight of epoxy alkyl silicone oil (A), polyetheramine (B), and aminoalkyl silicone oil (C), ranges from 5 to 30 wt %.

17. The block-modified polysiloxane of claim 5 , prepared by a process comprising:
reacting epoxyalkyl silicone oil (A), with polyetheramine (B), and then aminoalkyl silicone

Assignees

• Wacker Chemie Ag

Inventors

• Yang Heng
• Tian Shuai
• Sun Zhongliang

Classifications

• C08G77/452 Primary

  containing nitrogen-containing sequences · CPC title

• C08G77/44

  containing only polysiloxane sequences · CPC title

• C08G77/46 Primary

  containing polyether sequences · CPC title

• C08L83/08

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen · CPC title

• C08L83/12

  containing polyether sequences · CPC title