IP Library Granted Patent US 8,410,236
Granted Patent B2
US 8,410,236 · App. 12/601,071 · Granted Apr 2, 2013

Polycarbonate and/or polyurethane polyorganosiloxane compounds

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Quick Facts
Patent No.
US 8,410,236
App. No.
12/601,071
Granted
Apr 2, 2013
Kind
B2
Abstract

The invention relates to novel polycarbonate- and/or polyurethane-polyorganosiloxane compounds, processes for their preparation, their use, precursors for their preparation and reactive compositions which contain the precursors.

Claims (66)

1. A polycarbonate- and/or polyurethane-polyorganosiloxane compound containing at least one structural element of the formula (1):

wherein

Y 1 and Y 2 are independently chosen from —O—, —S— and —NR 2 —, wherein

R 2 is hydrogen or a straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radical having up to 40 carbon atoms, which can contain one or more groups chosen from —O—, —C(O)—, —NH— and —NR 3 —, wherein R 3 is a straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radical having up to 40 carbon atoms, which can contain one or more groups chosen from —O—, —C(O)— and —NH—, and

ST 1 and ST 2 are independently chosen from divalent to more than divalent, straight-chain, cyclic or branched, saturated, unsaturated or aromatic, substituted or unsubstituted hydrocarbon radicals having up to 1,000 carbon atoms, which can contain one or more groups chosen from —O—, —C(O)—, —NH—, —NR 3 —,

 and a polyorganosiloxane unit having 2 to 1,000 silicon atoms, wherein

R 5 is a straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radical having up to 100 carbon atoms, which can contain one or more groups chosen from —O—, —C(O)— and —NH—, or R 5 is a divalent radical which forms cyclic structures within the radicals ST 1 and ST 2 ,

or one or both of the radicals Y 1 adjacent to ST 1 , with ST 1 , and/or one or both of the radicals Y 2 adjacent to ST 2 , with ST 2 , can in each case form a nitrogen-containing heterocyclic radical, and

wherein if a plurality of radicals ST 1 is present, these can be identical or different, and if a plurality of radicals ST 2 is present, these can be identical or different,

ST 5 is an optionally substituted, divalent, straight-chain, cyclic or branched, saturated or unsaturated hydrocarbon radical having 1 to 12 carbon atoms,

ST 6 is an optionally substituted, divalent, straight-chain, cyclic or branched, saturated or unsaturated hydrocarbon radical having 1 to 12 carbon atoms,

with the proviso that ST 1 comprises a polyorganosiloxane radical, and wherein

ST 2 represents a radical of the formula

-ST 3 -N + (R 5 ) 2 -ST 4 -N + (R 5 ) 7 -ST 3 -

wherein

ST 3 is a straight-chain or cyclic or branched, saturated or unsaturated or aromatic, substituted or unsubstituted hydrocarbon radical having to 2 to 100 carbon atoms, which can be substituted by —O—, —C(O)—, —NH—, —NR 3 —, wherein R 3 is as defined above, and

ST 4 is a straight-chain or cyclic or branched, saturated or unsaturated or aromatic, substituted or unsubstituted hydrocarbon radical having to 2 to 100 carbon atoms, which can be substituted by —O—, —C(O)—, —NH—, —NR 3 — and by a polyorganosiloxane unit having 2 to 200 silicon atoms, wherein R 3 is as defined above,

or acid addition compounds and/or salts thereof of the compound of formula (1).

2. The compound of claim 1 , wherein ST 5 and ST 6 are each —CH 2 —, so that the formula (1) has the following structure:

wherein

Y 1 , ST 1 and ST 2 are as defined above.

3. The compound of claim 1 , wherein the compound is linear and wherein ST 1 and ST 2 are in each case divalent radicals.

4. The compound of claim 1 , wherein the compound is branched, and wherein at least one of the radicals ST 1 or ST 2 is tri- or tetravalent.

5. The compound of claim 1 , further comprising at least one polyorganosiloxane structural element of the formula (2):

wherein

R 4 is a straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radical having up to 20 C atoms, and

s=1 to 999.

6. The compound of claim 1 , wherein the compound comprises at least two structural elements of the formula (1).

7. The compound of claim 1 , wherein the compound comprises at least two polyorganosiloxane structural elements of the formula (2):

wherein

R 4 is a straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radical having up to 20 C atoms, and

s=1 to 999.

8. The compound of claim 1 , wherein Y 1 =—NR—, and wherein R 2 is as defined above.

9. The compound of claim 1 , wherein Y 1 and Y 2 =—NR 2 —, and wherein R 2 is as defined above.

10. The compound of claim 1 , wherein Y 1 and Y 2 =—NH—.

11. The compound of claim 1 , wherein the compound is linear and wherein ST 1 is the same as ST 2 and these are in each case divalent.

12. The compound of claim 1 , wherein ST 1 is different from ST 2 .

13. The compound of claim 1 , wherein ST 1 is

wherein s is 1 to 199, and

r=1 to 12.

14. The compound of claim 1 , having the following formula:

wherein

A − is an organic or inorganic anion,

with the proviso that at least one of the radicals ST 1 , ST 3 and ST 4 contains a polyorganosiloxane unit.

15. The compound of claim 1 , wherein ST 1 is selected from the group consisting of:

divalent, straight-chain hydrocarbon radicals having up to 15 carbon atoms,

divalent, mono- or polycyclic hydrocarbon radicals having up to 15 carbon atoms,

divalent, aromatic hydrocarbon radicals having up to 15 carbon atoms, and

radicals which are divalent or more than divalent and are derived from primary and secondary amino-functionalized prepolymers.

16. A method of preparing a composition useful as coatings, agents for modification of surfaces, elastomers, thermosets, adhesives, primers for metal and plastics surfaces, polymer additives, detergent additives, rheological agents, cosmetics and agents for modification of fibres, the method including providing the compound of claim 1 .

17. A formulation comprising at least one compound according to claim 1 , the formulation useful as a detergent, cosmetic or fiber treatment.

18. A polycarbonate- and/or polyurethane-polyorganosiloxane compound containing at least one structural element of the formula (1):

wherein

Y 1 and Y 2 are independently chosen from —O—, —S— and —NR 2 —, wherein

R 2 is hydrogen or a straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radical having up to 40 carbon atoms, which can contain one or more groups chosen from —O—, —C(O)—, —NH— and —NR 3 —, wherein R 3 is a straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radical having up to 40 carbon atoms, which can contain one or more groups chosen from —O—, —C(O)— and —NH—, and

ST 1 and ST 2 are independently chosen from divalent to more than divalent, straight-chain, cyclic or branched, saturated, unsaturated or aromatic, substituted or unsubstituted hydrocarbon radicals having up to 1,000 carbon atoms, which can contain one or more groups chosen from —O—, —C(O)—, —NH—, —NR 3 —,

 and a polyorganosiloxane unit having 2 to 1,000 silicon atoms, wherein

R 5 is a straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radical having up to 100 carbon atoms, which can contain one or more groups chosen from —O—, —C(O)— and —NH—, or R 5 is a divalent radical which forms cyclic structures within the radicals ST 1 and ST 2 ,

or one or both of the radicals Y 1 adjacent to ST 1 , with ST 1 , and/or one or both of the radicals Y 2 adjacent to ST 2 , with ST 2 , can in each case form a nitrogen-containing heterocyclic radical, and

wherein if a plurality of radicals ST 1 is present, these can be identical or different, and if a plurality of radicals ST 2 is present, these can be identical or different,

ST 5 is an optionally substituted, divalent, straight-chain, cyclic or branched, saturated or unsaturated hydrocarbon radical having 1 to 12 carbon atoms,

ST 6 is an optionally substituted, divalent, straight-chain, cyclic or branched, saturated or unsaturated hydrocarbon radical having 1 to 12 carbon atoms,

wherein ST 1 represents a radical which contains a polyalkylenoxy group and ST 2 represents a radical which contains a polyorganosiloxane group.

19. The compound of claim 18 , wherein the compound comprises at least one selected from the group consisting of amino groups, protonated amino groups and quaternary ammonium groups.

20. A formulation comprising at least one compound according to claim 18 , the formulation useful as a detergent, cosmetic or fiber treatment.

21. A method of preparing a composition useful as coatings, agents for modification of surfaces, elastomers, thermosets, adhesives, primers for metal and plastics surfaces, polymer additives, detergent additives, rheological agents, cosmetics and agents for modification of fibers, the method including providing the compound of claim 18 .

Assignments (6)
RELEASE OF SECURITY INTEREST Recorded Nov 11, 2020
From: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 054336/0023 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 28, 2016
From: MOMENTIVE PERFORMANCE MATERIALS GMBH
To: HENKEL AG & CO. KGAA
Reel/Frame 039879/0537 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded Nov 20, 2014
From: JPMORGAN CHASE BANK, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 034410/0607 →
SECURITY INTEREST Recorded Apr 22, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 032736/0552 →
SECURITY INTEREST Recorded Apr 22, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 032754/0774 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 28, 2010
From: SIMON, WALTER; SOCKEL, KARL-HEINZ; HUFFMULLER, GUNNAR; WAGNER, ROLAND; LANGE, HORST
To: MOMENTIVE PERFORMANCE MATERIALS GMBH
Reel/Frame 023864/0310 →