Low viscosity polyorganosiloxanes comprising quaternary ammonium groups, methods for the production and the use thereof (II)

Patent metadata

Field	Value
Publication number	US-9512275-B2
Application number	US-201314389195-A
Country	US
Kind code	B2
Filing date	Mar 26, 2013
Priority date	Mar 29, 2012
Publication date	Dec 6, 2016
Grant date	Dec 6, 2016

Abstract

Low viscosity polyorganosiloxanes comprising a) at least one polyorganosiloxane group, b) at least one quaternary ammonium group, c) at least one terminal group, selected from the groups consisting of: c1) at least one terminal mono functional polyorganosiloxane group, c2) at least one terminal ester group, and c3) at least one terminal alkyl-terminated poly ether group, compositions thereof, aqueous emulsions thereof, methods of the manufacture thereof and their use for the modification of surfaces of substrates.

First claim

The invention claimed is:

1. A polyorganosiloxane compound comprising:
a) at least one polyorganosiloxane group,
b) at least one quaternary ammonium group, and
c) at least one terminal group, selected from the groups consisting of:
c1) at least one terminal monofunctional polyorganosiloxane group,
c2) at least one terminal ester group, and
c3) at least one terminal alkyl-terminated polyether group;

wherein the polyorganosiloxane compound contains at least one terminal ester group c2); and
wherein the molar ratio of the quaternary ammonium groups b) and the terminal ester groups c2) is less than 100:15.

2. A polyorganosiloxane compound according to claim 1 , further comprising at least one functional group selected from the group consisting of:
d) reactive groups,
e) branching groups, and
f) polyalkylene oxide groups.

3. A polyorganosiloxane compound according to claim 2 , wherein the polyalkylene oxide group is an axial group in the polymer main chain of the general formula:
-A-E-A′-

wherein A and A′ each are independently selected from the group consisting of a single bond and a divalent organic group having up to 10 carbon atoms and optionally having one or more hetero atoms, and
E is a polyalkylene oxide group of the general formula:
—[CH 2 CH 2 O] q —[CH 2 CH(CH 3 )O] r —[CH 2 CH(C 2 H 5 )O] s —

with
q=0 to 200,
r=0 to 200,
s=0 to 200
and q+r+s=1 to 600.

4. A polyorganosiloxane compound according to claim 3 , wherein A and A′ are independently selected from the group consisting of
—CH 2 CH(CH 3 )—
—[CH 2 CH 2 O] q —[CH 2 CH(CH 3 )O] r —[CH 2 CH(C 2 H 5 )O] s —
—CH 2 C(O)O—, —CH 2 CH 2 C(O)O—, —CH 2 CH 2 CH 2 C(O)O—, —OC(O)CH 2 —, —OC(O)CH 2 CH 2 —, —OC(O)CH 2 CH 2 CH 2 —, —CH 2 C(O)—, —CH 2 CH 2 C(O)—, —CH 2 CH 2 CH 2 C(O)—, —C(O)CH 2 —, —C(O)CH 2 CH 2 —, —C(O)CH 2 CH 2 CH 2 —,
—CH 2 CH(OH)CH 2 —, —O—CH 2 CH(OH)CH 2 —, —CH 2 CH(OH)CH 2 —O—,
—[CH 2 CH 2 O] q —[CH 2 CH(CH 3 )O] r —[CH 2 CH(C 2 H 5 )O] s —

5. A polyorganosiloxane compound according to claim 1 , comprising at least one polyorganosiloxane group of the general formula:
—K—S 1 —K—,

with

wherein R 1 ═C 1 -C 22 -alkyl, C 1 -C 22 -fluoralkyl or aryl,
n=0 to 1000, and these can be identical or different if several S 1 Groups are present in the polyorganosiloxane compound,
K=is a bivalent or trivalent straight chain, cyclic and/or branched C 2 -C 40 hydrocarbon residue which is optionally interrupted by —O—, —NH—, trivalent N, —NR 1 —, —C(O)—, —C(S)—, and optionally substituted with —OH, wherein R 1 is defined as above, whereby the residues K can be identical or different from each other.

6. A polyorganosiloxane compound according to claim 1 , comprising at least one repeating unit comprising at least one quaternary ammonium group selected from the group consisting of:
—N + R 2 —,

—N + R 2 -T-N + R 2 —,

a saturated or unsaturated mono or diquaternary heterocycle of the formulae

an aromatic ammonium heterocycle of the formula

wherein R is selected from the group consisting of monovalent organic groups having up to 22 carbon atoms and optionally one or more heteroatoms, and wherein the free valencies at the nitrogen atoms are bound to carbon atoms, and T is a divalent organic group having up to 20 carbon atoms and one or more hetero atoms.

7. A polyorganosiloxane compound according to claim 1 , wherein the terminal monofunctional polyorganosiloxane group is a group of the general formula:
—K—S 2 ,

wherein K is a bivalent or trivalent straight chain, cyclic and/or branched C 2 -C 40 hydrocarbon residue which is optionally interrupted by —O—, —NH—, trivalent N, —NR 1 —, —C(O)—, —C(S)—, and optionally substituted with —OH, wherein R 1 is C 1 -C 22 -alkyl, C 1 -C 22 -fluoralkyl or aryl, whereby the residues K can be identical or different from each other, and S 2 is a monofunctional polyorganosiloxanyl group.

8. A polyorganosiloxane compound according to claim 7 , wherein the monofunctional polyorganosiloxane group is selected from the group consisting of:

wherein R 1 is C 1 -C 22 -alkyl, C 1 -C 22 -fluoralkyl or aryl which are identical or different and n=0 to 1000.

9. A polyorganosiloxane compound according to claim 1 , wherein the terminal alkyl-terminated polyether group c3) is a group of the general formula:
-A-E-R 4
wherein A is selected from a single bond or a divalent organic group having up to 10 carbon atoms and optionally having one or more hetero atoms, and
E is a polyalkylene oxide group of the general formulae:
—[CH 2 CH 2 O] q —[CH 2 CH(CH 3 )O] r —[CH 2 CH(C 2 H 5 )O] s —

with
q=0 to 200,
r=0 to 200,
s=0 to 200
and q+r+s=1 to 600, and
R 4 is an alkyl group with up to 6 carbon atoms.

10. A polyorganosiloxane compound according to claim 1 , wherein the terminal ester groups are selected from the group consisting of:
—OC(O)—Z
—OS(O) 2 —Z
—OS(O 2 )O—Z
—OP(O)(O—Z)OH and
—OP(O)(O—Z) 2
wherein Z is selected from monovalent organic residues having up to 40 carbon atoms, optionally comprising one or more hetero atoms.

11. A polyorganosiloxane compound according to claim of the general formula (I):
M-Y—[—(N + R 2 -T-N + R 2 )—Y-] m -M  (I),

or
M-Y—[—(N + R 2 )—Y-] m -M  (II)

or
M-Y—[—N + R 2 —Y-] m —[—(NR 2 -A-E-A′-NR 2 )—Y-] k -M  (II′)

wherein:
m is >0,
k is 0 or an average value of >0 to 50,
h is 0 to 100,
R is selected from monovalent organic groups having up to 22 carbon atoms and optionally one or more heteroatoms,
M represents a terminal group c), selected from the groups consisting of:
c1) at least one terminal monofunctional polyorganosiloxane group,
c2) at least one terminal ester group, and
c3) at least one terminal alkyl-terminated polyether group,
wherein in the moiety: -A-E-A′-
A and A′ each are independently selected from the group consisting of a single bond and a divalent organic group having up to 10 carbon atoms and optionally having one or more hetero atoms, and
E is a poly-alkylene oxide group of the general formula:
—[CH 2 CH 2 O] q —[CH 2 CH(CH 3 )O] r —[CH 2 CH(C 2 H 5 )O] s —

with
q=0 to 200,
r=0 to 200,
s=0 to 200
and q+r+s=1 to 600,
R 2 is selected from hydrogen or R,
Y is T, a group of the formulae:
—K—S—K— and -A-E-A′- or -A′-E-A-,

each as defined above, with the proviso that at least one Y is a group of the formula
—K—S—K—

with S=

wherein R 1 ═C 1 -C 22 -alkyl, C 1 -C 22 -fluoralkyl or aryl,
n=0 to 1000, and these can be identical or different if several S Groups
are present in the polyorganosiloxane compound,
K=is a bivalent or trivalent straight chain, cyclic and/or branched C 2 -C 40 hydrocarbon residue which is optionally interrupted by —O—, —NH—, trivalent N, —NR 1 —, —C(O)—, —C(S)—, and optionally substituted with —OH, wherein R 1 ═C 1 -C 22 -alkyl, C 1 -C 22 -fluoralkyl or aryl, whereby the residues K can be identical or different from each other and
T is selected from a divalent organic gr

Assignees

• Momentive Performance Mat Gmbh
• Momentive Performance Mat Inc

Inventors

• Wagner Roland
• Stachulla Karl-Heinz
• Sockel Karl-Heinz
• Gonzales Sigfredo
• Dussaud Anne

Classifications

• C08L83/10 Primary

  Block- or graft-copolymers containing polysiloxane sequences (obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C08L51/08, C08L53/00) · CPC title

• D06M15/643

  containing silicon in the main chain · CPC title

• C08G77/06

  Preparatory processes · CPC title

• A61Q5/06

  Preparations for styling the hair, e.g. by temporary shaping or colouring · CPC title

• D06M15/651

  comprising carboxylic groups · CPC title