IP Library Granted Patent US 6,958,410
Granted Patent B2
US 6,958,410 · App. 10/475,110 · Granted Oct 25, 2005

Amido-functional aminopolydiorganosiloxanes

Assignee: CHT R. Beitlich GmbH
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Quick Facts
Patent No.
US 6,958,410
App. No.
10/475,110
Granted
Oct 25, 2005
Kind
B2
Abstract

The invention relates to amido-functional aminopolydiorganosiloxanes, a method for the preparation thereof, formulations containing such amido-functional aminopolydiorganosiloxanes, and the use thereof.

Claims (63)

1. Amido-functional aminopolydiorganosiloxanes of general formula (I)

wherein R 1 represents the same or different monovalent C 1 to C 18 hydrocarbon residues optionally substituted with fluoro, chloro or bromo, hydrogen atoms, C 1 to C 12 alkoxy or hydroxy residues or alkylglycol residues;

R 2 represents R 1 and/or one of the groups X and/or Y;

X represents a group of general formula (II) and/or (III)

—R 3 NZR 4   (II)

—R 3 NR 5 (CH 2 ) p NZR 4   (III)

wherein R 3 represents a divalent C 1 to C 18 hydrocarbon residue;

R 4 represents a hydrogen atom or a C 1 to C 10 alkyl residue optionally substituted with fluoro, chloro or bromo;

Z is derived from hydroxycarboxylic acids and oxidized mono- and disaccharides, each having at least 2 hydroxy groups;

R 5 represents a hydrogen atom and/or Z;

Y represents a group of general formula (IV) and/or (V)

—R 3 NHR 4   (IV)

—R 3 NH(CH 2 ) p NHR 4   (V)

wherein R 3 and R 4 have the above mentioned properties;

m has an average value of from 0.5 to 50;

n has an average value of from 10 to 1500;

o has an average value of from 0 to 50; and

p represents the values 2, 3 or 4;

with the proviso that the ratio of m to o is within a range of from 10:1 to 0.1:1.

2. The amido-functional aminopolydiorganosiloxanes according to claim 1 , characterized in that Z is derived from uronic, aldaric and aldonic acids of general formulas (VI), (VII) and (VIII), respectively:

O═CH—[CH(OH)] s —CO—  (VI)

HOOC—[CH(OH)] s —CO—  (VII)

HOCH 2 —[CH(OH)] s —CO—  (VIII),

with 2≦s≦10.

3. The amido-functional aminopolydiorganosiloxanes according to claim 1 , characterized in that Z is derived from gluconic acid.

4. The amido-functional aminopolydiorganosiloxanes according to claim 1 , characterized in that the ratio of m to o is within a range of from 5:1 to 1:1.

5. A process for the preparation of amido-functional aminopolydiorganosiloxanes according to claim 1 , wherein an amino-functional polydiorganosiloxane of general formula (IX)

wherein R 1 represents the same or different monovalent C 1 to C 18 hydrocarbon residues optionally substituted with fluoro, chloro or bromo, hydrogen atoms, C 1 to C 12 alkoxy or hydroxy residues or alkylglycol residues;

R 6 represents R 1 and/or a group Y;

Y represents a group of general formula (IV) and/or (V)

—R 3 NHR 4   (IV)

—R 3 NH(CH 2 ) p NHR 4   (V)

wherein R 3 represents a divalent C 1 to C 18 hydrocarbon residue;

R 4 represents a hydrogen atom or a C 1 to C 10 alkyl residue optionally substituted with fluoro, chloro or bromo;

m has an average value of from 0.5 to 50;

n has an average value of from 10 to 1500;

o has an average value of from 0 to 50; and

p represents the values 2, 3 or 4;

with the proviso that the ratio of m to o is within a range of from 10:1 to 0.1:1;

is reacted, optionally in the presence of a solvent, with a lactone of a hydroxycarboxylic acid with at least 2 hydroxy groups at temperatures within a range of from 10 to 150° C.

6. The process according to claim 5 , characterized in that a molar excess of said hydroxycarboxylic acid and/or lactone of said hydroxycarboxylic acid of at least 10% by weight, especially from 10 to 500% by weight, preferably from 20 to 200% by weight, is employed, based on said amino-functional polydiorganosiloxane.

7. Formulations containing, based on the total composition:

A) from 2 to 80% by weight of one or more amido-functional aminopolydiorganosiloxanes of general formula I according to claim 1 ;

B) from 2 to 40% by weight of an emulsifier;

C) from 0 to 20% by weight of a hydrotropic agent; and

D) from 0 to 96% by weight of water.

8. The formulation according to claim 7 , further containing, based on the total composition:

E) from 0 to 5% by weight of inorganic or organic acid and/or its anhydride.

9. A method for the preparation of a formulation containing amido-functional aminopolydiorganosiloxanes claim 1 , according to claim 7 , characterized in that an amino-functional polyorganosiloxane of general formula (IX)

wherein R 1 represents the same or different monovalent C 1 to C 18 hydrocarbon residues optionally substituted with fluoro, chloro or bromo, hydrogen atoms, C 1 to C 12 alkoxy or hydroxy residues or alkylglycol residues;

R 6 represents R 1 and/or a group Y;

Y represents a group of general formula (IV) and/or (V)

—R 3 NHR 4   (IV)

—R 3 NH(CH 2 ) p NHR 4   (V)

wherein R 3 represents a divalent C 1 to C 18 hydrocarbon residue;

R 4 represents a hydrogen atom or a C 1 to C 10 alkyl residue optionally substituted with fluoro, chloro or bromo;

m has an average value of from 0.5 to 50;

n has an average value of from 10 to 1500;

o has an average value of from 0 to 50; and

p represents the values 2, 3 or 4;

is combined with a hydroxycarboxylic acid capable of lactone formation and having at least 2 hydroxy groups and/or a lactone of a hydroxycarboxylic acid with at least 2 hydroxy groups, and components B) and optionally C), D) and/or E) at temperatures within a range of from 10 to 90° C., and the milky to water-clear emulsion produced is optionally adjusted with component E) to pH values of <7.

10. In a process for finishing inorganic fibers and textiles in aqueous baths and application liquors wherein the improvement comprises the amido-functional aminopolydiorganosiloxanes of general formula I according to claim 1 .

11. The process according to claim 10 for the finishing of inorganic fibers and textiles wherein the improvement further comprises the optional inclusion of amino-functionally modified polydiorganosiloxanes, as a forced application by padding when employed on the padding machine, or in an exhausting, spraying or foam application on fast-running textile finishing machine.

Assignments (2)
CHANGE OF NAME Recorded Sep 23, 2019
From: CHT R. BEITLICH GMBH
To: CHT GERMANY GMBH
Reel/Frame 050456/0763 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 22, 2004
From: KOCH, MATTHIAS; NICKEL, FRIEDHELM; NOSTADT, KONRAD
To: CHT R. BEITLICH GMBH
Reel/Frame 015383/0215 →
Priority Claims (1)
DE 101 20 754 · Apr 27, 2001 · national
Continuity (1)
Related Publication 20040186308A1 · Sep 23, 2004