IP Library Granted Patent US 8,557,944
Granted Patent B2
US 8,557,944 · App. 13/279,676 · Granted Oct 15, 2013

Polysiloxanes with nitrogen-containing groups

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Quick Facts
Patent No.
US 8,557,944
App. No.
13/279,676
Granted
Oct 15, 2013
Kind
B2
Abstract

Endblocked polysiloxanes with lateral amino functions and at least one further lateral and/or terminal functional group.

Claims (78)

1. Polysiloxanes of formula 1:

M a D b D A c D B d D C e T f Q g   (formula 1)

where:

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

D=[R 1 2 SiO 2/2 ]

D A =[R 1 Si(R 7 NHR 3 )O 2/2 ]

D B =[R 1 SiR 4 O 2/2 ]

D C =[R 1 SiR 5 O 2/2 ]

T=[R 1 SiO 3/2 ]

Q=[SiO 4/2 ]

in which:

R 1 in each occurrence independently represents 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 in each occurrence independently represents R 1 , an alkoxy radical or a hydroxyl group;

R 3 in each occurrence independently represents hydrogen or a hydrocarbon radical substituted with nitrogen atoms;

R 4 in each occurrence independently represents identical or different linear or branched, saturated or olefinically unsaturated hydrocarbon radicals having 8 to 30 carbon atoms;

R 5 in each occurrence is independently selected from the group consisting of:

identical or different linear or branched, saturated or unsaturated polar hydroxyl-substituted amide radicals having 1 to 30 carbon atoms;

hydroxyl-substituted carbamate radicals having 1 to 30 carbon atoms;

ethoxylated amine radicals having 1 to 30 carbon atoms; and

guanidine radicals or alkylenylguanidine radicals having 1 to 30 carbon atoms;

R 7 in each occurrence independently represents identical or different linear or branched, saturated or unsaturated, divalent hydrocarbon groups having 1 to 20 carbon atoms;

a is 2 to 20;

b is 10 to 5000;

c is 1 to 500;

d is 0 to 500;

e is >0 to 500;

f is 0 to 20;

g is 0 to 20; and

c is >0.5*e;

or their ionic adducts with protic reactants H + A − ;

with the proviso that:

at least 50% of the R 2 radicals are =R 1 ; and

at least one occurrence of R 5 is a guanidine radical or an alkylenylguanidine radical having 1 to 30 carbon atoms.

2. The polysiloxanes according to claim 1 ; wherein R 5 is a substituent selected from the group of substituents of formulae 1a to 1h:

where R 6 is hydrogen, a hydrocarbon radical, an acyl radical, a carboxylate radical, or a carbamate or carbonate radical.

3. The polysiloxanes according to claim 1 ;

wherein anions A − are identical or different counter-ions to the positive charges on the protonated nitrogen-containing groups, selected from organic or inorganic anions of the acids H + A − and also derivatives thereof.

4. The polysiloxanes according to claim 2 ;

wherein anions A − are identical or different counter-ions to the positive charges on the protonated nitrogen-containing groups, selected from organic or inorganic anions of the acids H + A − and also derivatives thereof.

5. A composition comprising:

polysiloxanes according to claim 1 .

6. A composition comprising:

polysiloxanes according to claim 5 ; and

further formulation and processing auxiliaries.

7. A method of cleaning or reconditioning textiles and fabrics comprising:

applying an effective amount of the composition of claim 5 .

8. A process for preparing siloxanes according to claim 1 , comprising;

reacting different functional silanes in a condensation process with terminally hydroxyl-functional polydimethylsiloxanes to form multifunctional endblocked polysiloxanes;

wherein:

aminoalkyldialkoxysilanes are functionalized at the amino group in a first step; and

unfunctionalized aminoalkyldialkoxysilanes and the functionalized aminoalkyldialkoxysilanes are cocondensed in a second step with hydroxyl-functional polydimethylsiloxanes in the presence of reagents releasing trimethylsilyl groups.

9. The process according to claim 8 ;

characterized in that trimethylsilyl groups endblock the silicone chain selectively without silating the amino groups or hydroxyl groups of the lateral organic modifications.

10. The process according to claim 8 wherein:

a) terminally hydroxyl-functional linear or branched polysiloxanes and their mixtures with dimethyldialkoxysilanes or methyltrialkoxysilanes or tetraethoxysilane;

b) hexamethyldisilazane;

c) 3-aminopropylmethyldialkoxysilanes, N-(2-aminoethyl)-3-aminopropylmethyldialkoxysilanes; and

d) further functional dialkoxysilane comprising linear or branched, saturated or unsaturated hydrocarbon radicals, where the dialkoxysilanes utilized are:

(i) substituted with:

hydroxyl-substituted amides; and/or hydroxyl-substituted carbamate structures; and/or ethoxylated amines; and/or guanidine or alkylenylguanidine structures; or

(ii) selected from the group of substances of formulae 2a-2i

where R 1 and R 4 are each as defined for formula 1, R 8 is a hydrogen atom, a methyl group or a carboxyl group and R 9 is an alkyl or acyl radical;

with the proviso that at least one dialkoxysilane utilized is substituted with a guanidine or alkylenylguanidine structure;

are reacted with one another.

11. The process according to claim 9 wherein:

a) terminally hydroxyl-functional linear or branched polysiloxanes and their mixtures with dimethyldialkoxysilanes or methyltrialkoxysilanes or tetraethoxysilane;

b) hexamethyldisilazane;

c) 3-aminopropylmethyldialkoxysilanes, N-(2-aminoethyl)-3-aminopropylmethyldialkoxysilanes; and

d) further functional dialkoxysilanes comprising linear or branched, saturated or unsaturated hydrocarbon radicals, where the dialkoxysilanes utilized are:

(i) substituted with:

hydroxyl-substituted amides; and/or

hydroxyl-substituted carbamate structures; and/or

ethoxylated amines; and/or

guanidine or alkylenylguanidine structures; or

(ii) selected from the group of substances of formulae 2a-2i:

where R 1 and R 4 are each as defined for formula 1, R 8 is a hydrogen atom, a methyl group or a carboxyl group and R 9 is an alkyl or acyl radical;

with the proviso that at least one dialkoxysilane utilized is substituted with a guanidine or alkylenylguanidine structure;

are reacted with one another.

Assignments (2)
MERGER Recorded Feb 26, 2014
From: EVONIK GOLDSCHMIDT GMBH
To: EVONIK DEGUSSA GMBH
Reel/Frame 032335/0326 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 12, 2011
From: HENNING, FRAUKE, DR.; FERENZ, MICHAEL, DR.; KNOTT, WILFRIED, DR.; SILBER, STEFAN, DR.; WENK, HANS HENNING, DR.; KUPPERT, DIRK, DR.; KOENIG, FRANK
To: EVONIK GOLDSCHMIDT GMBH
Reel/Frame 027363/0754 →