IP Library Granted Patent US 10,266,658
Granted Patent B2
US 10,266,658 · App. 15/546,142 · Granted Apr 23, 2019

OEM textile finishing compositions

Inventors: Frauke Henning (Essen, DE); Jörg Peggau (Essen, DE); Andrea Lohse (Bottrop, DE); Ulrike Mahring (Essen, DE); Fuming Chen (Shanghai, CN)
Assignee: EVONIK DEGUSSA GMBH
C08G77/54A61C5/12A61K8/898C08G81/00C08J3/24C08L83/14D06M15/6436D06M15/652D06M2101/32D06M2200/50
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Quick Facts
Patent No.
US 10,266,658
App. No.
15/546,142
Granted
Apr 23, 2019
Kind
B2
Abstract

Crosslinked aminosiloxanes obtainable by reaction of identical or different aminosiloxanes with identical or different epoxide components which are water-soluble hydrocarbons, the hydrocarbons comprising oxygen as well as carbon, and optionally further elements selected from nitrogen, sulphur and phosphorus, the hydrocarbon having on average more than one terminal epoxy group, the epoxy group being a carbooxirane radical, and, further, not more than 50% of all the amino groups having undergone reaction with an epoxide group.

Claims (60)

1. A crosslinked aminosiloxane obtained by reaction of identical or different amine-substituted siloxanes with identical or different epoxide components which are water-soluble hydrocarbons, the hydrocarbons comprising oxygen and carbon, the hydrocarbon having on average more than one terminal epoxy group, the epoxy group being a carbooxirane radical, and, further, not more than 50% of all the amino groups having undergone reaction with an epoxide group

wherein the epoxide components are epoxy-substituted polyethers of formula (II)

R 3 —X-M 1 h -M 2 j -M 3 k -M 4 l -M 5 m -R 3   (II)

h=greater than 0 to 50;

j=0 to 10;

k=0 to 10;

l=greater than 1 to 10;

m=0 to 10;

where the sum of the indices h, j, k, l+m is at least 3,

X=oxygen,

R 3 =independently at each occurrence hydrogen, a hydrocarbon having 1 to 8 carbon atoms, and/or the gycidyl radical

where in M 3 , the radicals X 1 to X 4 independently of one another are hydrogen or linear, cyclic or branched, aliphatic or aromatic, saturated or unsaturated hydrocarbon radicals having 1 up to 50 C atoms, wherein X 1 to X 4 are not selected such that M 3 is the same as M 1 or M 2 ,

where R 4 in M 4 independently at each occurrence is a hydrocarbon radical having 2 to 20 carbons, and may be interrupted by heteroatoms, M 4 is a glycidyl ether=

where R 5 in M 5 independently at each occurrence is not present or is a divalent hydrocarbon having 1 to 10 carbon atoms.

2. The crosslinked aminosiloxane according to claim 1 , wherein the amine-substituted siloxanes conform to the formula (I)

M a M A b D c D A d T e T A f Q g   (I)

where

M=[R 1 3 SiO 1/2 ]

M A =[R 2 R 1 2 SiO 1/2 ]

D=[R 1 2 SiO 2/2 ]

D A =[R 2 R 1 SiO 2/2 ]

T=[R 1 SiO 3/2 ]

T A =[R 2 SiO 3/2 ]

Q=[SiO 4/2 ],

where

R 1 independently at each occurrence is identical or different, linear or branched, saturated or unsaturated hydrocarbon radicals having 1 to 30 carbon atoms or else aromatic hydrocarbon radicals having 6 to 30 carbon atoms,

R 2 independently at each occurrence is a hydrocarbon radical which is substituted by at least one nitrogen atom and has 1 to 30 carbon atoms,

a=0 to 20,

b=0 to 10,

c=10 to 5000,

d=0 to 50,

e=0 to 20,

f=0 to 500,

g=0 to 20.

3. The crosslinked aminosiloxane according to claim 1 , wherein the epoxide components are water-soluble hydrocarbons, the hydrocarbons comprising oxygen as well as carbon, the hydrocarbon having at least one chain which in turn has at least two oxygen atoms separated by at least one carbon atom and the hydrocarbon having on numerical average more than one terminal epoxy group.

4. The crosslinked aminosiloxane according to claim 1 , wherein the epoxy-substituted polyethers of the formula (II) have a molar mass of 200 to 1500 g/mol.

5. The crosslinked aminosiloxane according to claim 1 , wherein the epoxy-substituted polyethers of formula (II) are colorless.

6. The crosslinked aminosiloxane according to claim 1 , wherein the crosslinked aminosiloxanes have less than 10 wt %, but at least 0.01 wt %, polyether fraction.

7. The crosslinked aminosiloxane according to claim 1 , wherein at least 50% of the primary amino groups of the crosslinked siloxanes have not undergone reaction by crosslinking with epoxide groups.

8. The process for preparing the crosslinked aminosiloxane according to claim 1 .

9. A composition comprising the crosslinked aminosiloxane of claim 1 .

10. The composition according to claim 9 , wherein they comprise from 0.1 wt % to 5 wt %, based on the mass of the crosslinked aminosiloxane, of an acid.

11. A formulation comprising the composition according to claim 9 , wherein the formulation is emulsifier-free.

12. A household product including fabric softener and hair conditioner wherein the household product comprised the crosslinked aminosiloxane of claim 1 .

13. The crosslinked aminosiloxane according to claim 1 wherein the hydrocarbons may further consist of elements selected from the group consisting of nitrogen, sulphur and phosphorus.

14. The crosslinked aminosiloxane according to claim 1 wherein the epoxide components the hydrocarbon having at least one chain which in turn has at least two oxygen atoms separated by at least two carbon atoms, and the hydrocarbon having on numerical average more than two terminal epoxy groups.

15. The crosslinked aminosiloxane according to claim 1 , wherein the epoxide components are epoxy-substituted polyethers of formula (II)

(II)

h=from 4 to 15;

j=0 to 5;

k=0;

l=from 2 to 5;

m=0;

where the sum of the indices h, j, k, l+m is at least 5,

X =oxygen,

R 3 =independently at each occurrence hydrogen, a hydrocarbon having 1 to 8 carbon atoms and/or the gycidyl radical

where in M 3 , the radicals X 1 to X 4 independently of one another are hydrogen or linear, cyclic or branched, aliphatic or aromatic, saturated or unsaturated hydrocarbon radicals having 1 up to 50 C atoms, wherein X 1 to X 4 are not selected such that M 3 is the same as M 1 or M 2 ,

where R 4 in M 4 independently at each occurrence is a hydrocarbon radical having 2 to 20 carbons, and may be interrupted by heteroatoms, M 4 is a glycidyl ether=

where R 5 in M 5 independently at each occurrence is not present or is a divalent hydrocarbon having 1 to 10 carbon atoms.

16. The crosslinked aminosiloxane according to claim 2 , wherein the epoxy-substituted polyethers of the formula (II) have a molar mass of 200 to 1500 g/mol.

Assignments (3)
CHANGE OF NAME Recorded Dec 27, 2019
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051428/0710 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ADD BY ADDING THE SECOND ASSIGNEE NAME PREVIOUSLY RECORDED AT REEL: 044050 FRAME: 0552. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT . Recorded Nov 16, 2017
From: HENNING, FRAUKE; PEGGAU, JÖRG; LOHSE, ANDREA; MAHRING, ULRIKE; CHEN, FUMING
To: EVONIK DEGUSSA GMBH; EVONIK SPECIALTY CHEMICALS (SHANGHAI) CO., LTD.
Reel/Frame 044760/0870 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 7, 2017
From: HENNING, FRAUKE; PEGGAU, JÖRG; LOHSE, ANDREA; MAHRING, ULRIKE; CHEN, FUMING
To: EVONIK DEGUSSA GMBH
Reel/Frame 044050/0552 →
Continuity (1)
Related Publication 20180009954A1 · Jan 11, 2018
Cited By (1)
US 12,305,148