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

Patent metadata

Field	Value
Publication number	US-10160834-B2
Application number	US-201615209121-A
Country	US
Kind code	B2
Filing date	Jul 13, 2016
Priority date	Jul 13, 2016
Publication date	Dec 25, 2018
Grant date	Dec 25, 2018

Abstract

The present invention provides a polyorganosiloxane compound having a low viscosity, a process for the manufacture of such polyorganosiloxane compounds, polyorganosiloxane compositions comprising said polyorganosiloxane compound and another polyorganosiloxane compound which is different from the polyorganosiloxane compound, aqueous emulsions comprising the polyorganosiloxane compound, and a method of surface treatment using the polyorganosiloxane compound.

First claim

The invention claimed is:

1. A polyorganosiloxane compound comprising:
at least one polyorganosiloxane group (a),
at least one quaternary ammonium group (b),
at least one terminal ester group (c),
at least one functional organic group (d), comprising one or more hydroxyl groups and at least one functional group selected from an ester group, an ether group and an amino group, and
wherein the molar ratio of the quaternary ammonium groups (b) and the terminal ester groups (c) is less than 100:15 and
wherein the polyorganosiloxane compound comprises at least one unit of the formula (I):
[—CH 2 —X—CH 2 -D-]  (I)

wherein
D is selected from the group consisting of:
—N + R 2 —,

—N + R 2 —Y—N + R 2 —,

a saturated or unsaturated mono or diquaternary heterocycle of the formulae

and an aromatic ammonium heterocycle of the formula

wherein
X is at least one group X 1 and at least one group X 2 , wherein
X 1 is a difunctional organic group, comprising three or more hydroxyl groups and at least one functional group selected from the group consisting of an ester group, an ether group and an amino group, and wherein said group X 1 does not comprise a polydiorganosiloxane group,
X 2 is a difunctional organic group, comprising at least one polydiorganosiloxane group,
R can be the same or different is selected from monovalent organic groups having up to 22 carbon atoms and optionally one or more heteroatoms, and
Y is a difunctional organic group optionally comprising one or more heteroatoms.

2. A polyorganosiloxane compound according to claim 1 , wherein the terminal ester group (c) is selected from the group consisting of carboxylic acid ester groups, sulfonic acid ester groups, sulfuric acid ester groups, and phosphoric acid mono- or diester groups.

3. A polyorganosiloxane compound according to claim 1 ,
wherein the units of the formula (I) are selected from formula (Ia):
[—CH 2 —X—CH 2 —N + R 2 —Y—N + R 2 —]  (Ia)

wherein X, R and Y are as defined.

4. A polyorganosiloxane compound according to claim 3 , wherein the units of the formula (Ia) are selected from the group consisting of:
[—CH 2 —C(O)—O—X 3 —O—C(O)—CH 2 —N + R 2 —Y—N + R 2 —]  (II), and

[—CH 2 —CH(OH)—X 4 —CH(OH)—CH 2 —N + R 2 —Y—N + R 2 —]  (III),

wherein R and Y are as defined above,
X 3 is both X 31 and X 32 ,
wherein
X 31 is selected from a difunctional organic group, comprising three or more hydroxyl groups and at least one functional group selected from the group consisting of an ester group, an ether group and an amino group, and wherein said group X 31 does not comprise a polydiorganosiloxane group,
X 32 is a difunctional organic group, comprising at least one polydiorganosiloxane group,
and
X 4 is both X 41 and X 42 ,
wherein
X 41 is selected from a difunctional organic group, comprising three or more hydroxyl groups and at least one functional group selected from the group consisting of an ester group, an ether group and an amino group, and wherein said group X 41 does not comprise a polydiorganosiloxane group,
X 42 is a difunctional organic group, comprising at least one polydiorganosiloxane group.

5. A polyorganosiloxane compound according to claim 4 , comprising units of the formula (II) and of the formula (III).

6. A polyorganosiloxane compound according to claim 4 , wherein
X 41 is selected from the group consisting of
a group of formula (IV):
—(X 43 —CH(OH)—CH 2 —O—C(O)—X 44 —C(O)—O—CH 2 —CH(OH)—) x1 —X 43 —  (IV)

wherein X 43 is a difunctional organic group, comprising three or more hydroxyl groups and at least one functional group selected from the group consisting of an ester group, an ether group and an amino group, X 44 is an optionally substituted difunctional organic group, optionally comprising one or more heteroatoms, and x1 is ≥1,
and a group of formula (V):
—(X 43 —CH(OH)—CH 2 —N(R 1 )—X 45 —N(R 1 )—CH 2 —CH(OH)—) x2 —X 43 —  (V)

wherein X 43 is as defined above, X 45 is a difunctional organic group, optionally comprising one or more heteroatoms, R 1 is selected from the group consisting of hydrogen and a C1-C6 alkyl group, and x2 is ≥1,
X 31 is selected from the group consisting of
a group of formula (VI):
—CH 2 —CH(OH)—(X 33 —CH(OH)—CH 2 —O—C(O)—X 34 —C(O)—O—CH 2 —CH(OH)—) x3 —X 33 —CH(OH)—CH 2 —  (VI)

wherein X 33 is a difunctional organic group, comprising three or more hydroxyl groups and at least one functional group selected from the group consisting of an ester group, an ether group and an amino group, X 34 is a difunctional organic group, optionally comprising one or more heteroatoms, and x3 is ≥1,
and a group of formula (VII):
—CH 2 —CH(OH)—(X 33 —CH(OH)—CH 2 —N(R 1 )—X 45 —N(R 1 )—CH 2 —CH(OH)—) x4 —X 33 —CH(OH)—CH 2 —  (VII)

wherein X 33 , X 45 and R 1 are as defined above, and x4 is ≥1.

7. A polyorganosiloxane compound according to claim 1 ,
wherein formula (I) is selected from the group consisting of:
[—CH 2 —C(O)—O—(CH 2 CH(OH)CH 2 O) 3 —C(O)—CH 2 —N + R 2 —Y—N + R 2 —]  (I-a),

[—CH 2 —CH(OH)—CH 2 —O—CH 2 —CH(OH)—CH 2 —O—CH 2 —CH(OH)—CH 2 —N + R 2 —Y—N + R 2 —]  (III-a), and

[—CH 2 —C(O)—O—CH 2 —CH(OH)—(X 33 —CH(OH)—CH 2 —O—C(O)—X 34 —C(O)—O—CH 2 —CH(OH)—) x3 —X 33 —CH(OH)—CH 2 —O—C(O)—CH 2 —N + R 2 —Y—N + R 2 —]   (II-b)

wherein X 33 is a moiety of the following formula:
—CH 2 —O—CH 2 —CH(OH)—CH 2 —O—CH 2 —

and wherein X 34 is a moiety of the following formula:
—CH(OH)—CH(OH)—

and wherein R and Y are each as defined and x3≥1.

8. A polyorganosiloxane compound according to claim 1 , comprising more than one unit of the formula (I).

9. A polyorganosiloxane compound according to claim 1 , wherein the group X 1 is of the formula (VIII):
-A-E-A′-  (VIII)

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 one or more hetero atoms, and E is selected from the group consisting of the formulas

wherein q is independently from each other ≥1, and denotes a single bond,

wherein denotes a single bond, R 2 is an optionally substituted, divalent straight chain, cyclic aliphatic and/or branched and/or aromatic hydrocarbon residue with up to 40 carbon atoms, which optionally contains one or more heteroatoms selected from O or N, and wherein each q is independently ≥1, and

wherein denotes a single bond, R 2 is as defined above, each q independently is ≥1, and p is >1,
with the proviso that A and E or A′ and E are not bonded via two hetero atoms and provided that E contains three or more hydroxy groups.

10. A polyorganosiloxane compound according to claim 1 , wherein group X 1 is of the formula (VIII) -A-E-A 1 (VIII) 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 one or more hetero atoms, and E is a group E 4 of formula:

Assignees

• Momentive Performance Mat Gmbh
• Momentive Performance Mat Inc

Inventors

• Wagner Roland
• Stachulla Karl-Heinz
• Streicher Katharina
• Wenske Christian

Classifications

• A61Q5/02

  Preparations for cleaning the hair · CPC title

• A61Q3/00

  Manicure or pedicure preparations · CPC title

• A61K8/891

  saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone · CPC title

• A61Q5/06

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

• C08G77/06

  Preparatory processes · CPC title