Amino acid-modified siloxanes, process for preparing them and application

Patent metadata

Field	Value
Publication number	US-9481695-B2
Application number	US-201414331831-A
Country	US
Kind code	B2
Filing date	Jul 15, 2014
Priority date	Jul 18, 2013
Publication date	Nov 1, 2016
Grant date	Nov 1, 2016

Abstract

A process for preparing amino acid-modified siloxanes that can be carried out under mild conditions is provided as well as organically modified silicones for care formulations for skin, hair and textiles that are toxicologically unobjectionable.

First claim

What is claimed is:

1. A process for preparing an amino acid-modified siloxane, comprising:
reacting a salt of the general formula K+A − with at least one siloxane having at least one epoxy group and/or carbonate group, where
K + is the organic cation cetyltrimethylammonium, and
A − is selected from the group consisting of arginate, lysinate, and histidate.

2. The process according to claim 1 , wherein the at least one siloxane is a compound of general formula IV
M a1 M A a2 M B a3 D b1 D A b2 D B b3 T c1 T A c2 T B c3 Q d1    general formula IV

with
M=[R 16 3 SiO 1/2 ]
M A =[R 17 R 16 2 SiO 1/2 ]
M B =[R 18 R 16 2 SiO 1/2 ]
D=[R 16 2 SiO 2/2 ]
D A =[R 17 1 R 16 1 SiO 2/2 ]
D B =[R 18 1 R 16 1 SiO 2/2 ]
T=[R 16 SiO 3/2 ]
T A =[R 17 SiO 3/2 ]
T B =[R 18 SiO 3/2 ]
Q=[SiO 4/2 ],
where
R 16 independently at each occurrence is identical or different, linear or branched, saturated or unsaturated hydrocarbon radicals having 1 to 30 carbon atoms or aromatic hydrocarbon radicals having 6 to 30 carbon atoms,
R 17 independently at each occurrence is identical or different radicals containing epoxy and/or carbonate groups,
R 18 independently at each occurrence is identical or different, linear or branched, saturated or olefinically unsaturated hydrocarbon radicals having 8 to 30 carbon atoms,
an aromatic hydrocarbon radical with 6 to 40 carbon atoms, an alkylaryl radical with 7 to 40 carbon atoms,
a linear or branched, optionally double bond-containing aliphatic hydrocarbon radical with 2 to 30 carbon atoms interrupted by one or more heteroatoms,
a linear or branched, optionally double bond-containing aliphatic hydrocarbon radical having from 2 to 30 carbon atoms, which is interrupted by one or more functionalities selected from the group of —O—C(O)—, —(O)C—O—, —NH—C(O)—, —(O)C—NH, —(CH 3 )N—C(O)—, —(O)C—N(CH 3 )—, —S(O 2 )—O—, —O—S(O 2 )—, —S(O 2 )—NH—, —NH—S(O 2 )—, —S(O 2 )—N(CH 3 )—, and —N(CH 3 )—S(O 2 )—,
a terminally OH, OR′, NH 2 , N(H)R′, N(R′) 2 functionalized linear or branched optionally double bond-containing aliphatic or cycloaliphatic hydrocarbon radical with 1 to 30 carbon atoms, wherein R′ is an optionally double bond-containing C1 to C30 alkyl radical, or
a blockwise or randomly constructed polyether according to —(R 5 —O) n —R 6 , where R 5 is a linear or branched hydrocarbon radical containing 2 to 4 carbon atoms, n is 1 to 100, and R 6 is hydrogen, a linear or branched optionally double bond-containing aliphatic hydrocarbon radical with 1 to 30 carbon atoms, an optionally double bond-containing cycloaliphatic hydrocarbon radical with 5 to 40 carbon atoms, an aromatic hydrocarbon radical with 6 to 40 carbon atoms, an alkylaryl radical with 7 to 40 carbon atoms,
or a radical —C(O)—R 7 , where R 7 is a linear or branched optionally double bond-containing aliphatic hydrocarbon radical with 1 to 30 carbon atoms, an optionally double bond-containing cycloaliphatic hydrocarbon radical with 5 to 40 carbon atoms, an aromatic hydrocarbon radical with 6 to 40 carbon atoms, an alkylaryl radical with 7 to 40 carbon atoms,
a1=0 to 200,
a2=0 to 30,
a3=0 to 30,
b1=3 to 5000,
b2=0 to 100,
b3=0 to 100,
c1=0 to 30,
c2=0 to 30,
c3=0 to 30,
d1=0 to 30,
with the proviso that at least one of the indices a2, b2 or c2≠0.

3. The process of claim 1 further comprising:
reacting the amino acid-modified siloxane with a further organic component containing epoxy groups.

4. The process of claim 1 further comprising purifying the amino acid-modified siloxane.

Assignees

• Evonik Industries Ag

Inventors

• Knott Wilfried
• Henning Frauke
• Amajjahe Sadik
• Krauskopf Sarah
• Fiedel Michael
• Jazkewitsch Olga
• Hartung Christian

Classifications

• C07C211/63

  having quaternised nitrogen atoms bound to acyclic carbon atoms · CPC title

• C08G77/388

  containing nitrogen · CPC title

• C07F7/1804 Primary

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title

• C07F9/5407

  Acyclic saturated phosphonium compounds · CPC title

• C07C279/14 Primary

  being further substituted by carboxyl groups · CPC title