Silicone copolymers production thereof and use thereof for treatment of fibrous substrates

Patent metadata

Field	Value
Publication number	US-11845914-B2
Application number	US-201716772970-A
Country	US
Kind code	B2
Filing date	Dec 13, 2017
Priority date	Dec 13, 2017
Publication date	Dec 19, 2023
Grant date	Dec 19, 2023

Abstract

Low molecular weight silicone copolymers prepared by reacting an oxamido ester-terminated silicone with a polyetheramine and a primary or secondary amine are useful in treating fabrics to obtain a soft hand and also hydrophilicity, and can be prepared without the use of highly toxic reagents.

First claim

The invention claimed is:

1. A silicone copolymer (A) of the formula (I)

where
Y is identical or different and denotes a divalent hydrocarbon radical which has 1 to 20 carbon atoms, optionally containing one or more heteroatoms,
Z is identical or different and denotes a divalent organic radical which contains a polyoxyalkylene group,
R 1 is identical or different and is a radical of the formula
—N(R 4 )—R 5   (IV′),

R 2 is identical or different and denotes a monovalent hydrocarbon radical which has 1 to 18 carbon atoms, optionally containing halogen or oxygen atoms,
R 3 is identical or different and is a hydrogen atom or a monovalent hydrocarbon radical having 1 to 20 carbon atoms,
R 4 denotes a hydrogen atom, a C 1-18 alkyl radical, or a hydrocarbon radical which has 4 to 18 carbon atoms and contains one or more oxygen or nitrogen atoms, and
R 5 denotes a C 1-18 alkyl radical, or a hydrocarbon radical which has 4 to 18 carbon atoms and contains one or more oxygen or nitrogen atoms,
or R 4 and R 5 in formula (IV′) together denote a divalent hydrocarbon radical which optionally contains one or more oxygen or nitrogen atoms,
R 6 is identical or different and denotes a C 1 -C 10 alkylene radical, and
R 7 denotes a C 1 -C 10 alkylene radical,
n is an integer from 10 to 2000,
p is an integer from 1 to 5, and
w is on average 2.5 to 80.

2. The silicone copolymer of claim 1 , wherein
Y is identical or different and denotes a divalent hydrocarbon radical which has 1 to 20 carbon atoms, optionally containing oxygen or nitrogen atoms,
Z is identical or different and denotes a divalent organic radical which contains a radical of the formula —(R 6 O) w —R 7 —,
R 1 is identical or different and is a radical of the formula
—N(R 4 )—R 5   (IV′),

R 2 is identical or different and denotes a monovalent hydrocarbon radical which has 1 to 18 carbon atoms, optionally containing halogen or oxygen atoms,
R 3 is identical or different and is a hydrogen atom or a monovalent hydrocarbon radical having 1 to 20 carbon atoms,
R 4 denotes a hydrogen atom, a C 1-18 alkyl radical, or a hydrocarbon radical which has 4 to 18 carbon atoms and contains one or more oxygen or nitrogen atoms, and
R 5 denotes a C 1-18 alkyl radical, or a hydrocarbon radical which has 4 to 18 carbon atoms and contains one or more oxygen or nitrogen atoms,
or R 4 and R 5 in formula (IV′) together denote a divalent hydrocarbon radical which optionally contains one or more oxygen or nitrogen atoms,
R 6 is identical or different and denotes a C 2 -C 3 alkylene radical, and
R 7 denotes a C 2 -C 3 alkylene radical,
n is an integer from 10 to 300,
p is an integer from 1 to 2, and
w is on average 10 to 30.

3. The silicone copolymer of claim 1 , wherein Y is a 1,3-propylene radical.

4. A process for preparing a silicone copolymer of claim 1 , comprising:
reacting
(1) organopolysiloxanes terminated with oxamidoester groups, of the formula (II)

wherein R* is a monovalent hydrocarbon radical having 1 to 18 carbon atoms, or is a radical R 5 ,
with
(2) polyetheramines of the formula
R 3 HN—Z—NHR 3   (III),

and with
(3) primary or secondary amines of the formula
H—N(R 4 )—R 5   (IV).

5. The process of claim 4 , wherein polyetheramines (2) are used in amounts of 0.3 to 0.8 mol of amino groups in (2) per mole of oxamidoester groups in organopolysiloxane (1).

6. The process of claim 4 , wherein primary or secondary amines (3) are used in amounts of 0.2 to 0.7 mol of amino groups in (3) per mole of oxamidoester groups in organopolysiloxane (1).

7. An aqueous emulsion comprising:
at least one silicone copolymers (A) as claimed in claim 1 , at least one emulsifier (B) and/or coemulsifier (B′), and
water (C).

Assignees

• Wacker Chemie Ag

Inventors

• Lehotkay Thomas
• Eichberger Walter
• Schaefer Oliver
• Seeger-Feichtinger Inge

Classifications

• C11D3/3742 Primary

  Nitrogen containing silicones · CPC title

• C08G77/455

  containing polyamide, polyesteramide or polyimide sequences · CPC title

• C11D3/0015

  liquid · CPC title

• D06M15/6436

  containing amino groups · CPC title

• D06M2101/06

  cellulosic · CPC title