IP Library Granted Patent US 8,673,985
Granted Patent B2
US 8,673,985 · App. 12/921,446 · Granted Mar 18, 2014

Polycarbonate-polyorganosiloxane- and/or polyurethane-polyorganosiloxane compounds

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,673,985
App. No.
12/921,446
Granted
Mar 18, 2014
Kind
B2
Abstract

The present invention relates to novel polycarbonate-polyorganosiloxane and/or polyurethane-polyorganosiloxane compounds, methods for their production, their use, functional formulations containing them, precursors for their production, as well as reactive compositions containing the aforementioned precursors.

Claims (68)

1. A polyorganosiloxane compound including at least one of a polycarbonate group and a polyurethane group, containing at least one structural element of the formula (1):

wherein

R is respectively selected from hydrogen, alkyl, or a bond to the residue ST 1 , with cyclic structures forming if R represents a bond to the residue ST 1 ,

R 1 is respectively selected from hydrogen, alkyl, or a bond to the residue ST 1 , with cyclic structures forming if R 1 represents a bond to the residue ST 1 ,

R 2 is respectively selected from hydrogen, alkyl, or a bond to the residue ST 1 , with cyclic structures forming if R 1 represents a bond to the residue ST 1 ,

ST 1 is a di- or polyvalent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic, substituted or unsubstituted hydrocarbon residue with up to 1000 carbon atoms, which may contain one or more groups selected from:

—O—,

—C(O)—, and

a polyorganosiloxane unit with 2 to 1000 silicon atoms,

wherein

ST 1 contains no groups of the formula —O—C(O)—O— and no groups of the formula —O—C(O)—NH—,

wherein, if a plurality of residues ST 1 is present, they may be the same or different,

Y is selected independently from one another from: —O—, —S— and —NR 6 —, wherein

R 6 is hydrogen or a straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residue with up to 40 carbon atoms, which may contain one or more groups selected from —O—, —C(O)—, —NH— and —NR 3 —,

wherein R 3 is R 3 is a straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residue with up to 40 carbon atoms, which may contain one or more groups selected from —O—, —C(O)— and —NH—, and may optionally be substituted by a silyl group or

R 6 represents a bond to the residue ST 2 while forming cyclic structures,

ST 2 is a di- or polyvalent, straight-chained, cyclic or branched, saturated, unsaturated or aromatic, substituted or unsubstituted hydrocarbon residue with up to 1000 carbon atoms, which may contain one or more groups selected from:

a polyorganosiloxane unit with 2 to 1000 silicon atoms,

wherein

R 5 is a straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residue with up to 100 carbon atoms, which may contain one or more groups selected from —O—, —C(O)— and —NH—, and may optionally be substituted by a silyl group, or two residues R 5 form, with the nitrogen atom to which they are bonded, a 5 to 7-membered ring, which may optionally contain one or two further hetero atoms, or R 5 , together with R 6 , forms a divalent alkylene residue which leads to the formation of a cyclic structure including Y and ST 2 ,

wherein, if a plurality of residues ST 2 is present, they may be the same or different,

provided that at least one of the residues ST 1 and/or ST 2 comprises a polyorganosiloxane residue,

or acid addition compounds and/or salts thereof, wherein

at least one of ST 1 and ST 2 contain a polyalkyleneoxy group.

2. The polyorganosiloxane compound including at least one of a polycarbonate group and a polyurethane group according to claim 1 , wherein at least one of the residues R, R 1 and R 2 is hydrogen.

3. The polyorganosiloxane compound including at least one of a polycarbonate group and a polyurethane group according to claim 2 , wherein the residues R, R 1 and R 2 are hydrogen.

4. The polyorganosiloxane compound including at least one of a polycarbonate group and a polyurethane group according to claim 1 , wherein the compound is linear.

5. The polyorganosiloxane compound including at least one of a polycarbonate group and a polyurethane group according to claim 1 , wherein ST 1 and ST 2 are each divalent residues.

6. The polyorganosiloxane compound including at least one of a polycarbonate group and a polyurethane group according to claim 1 , wherein the compound is branched.

7. The branched polyorganosiloxane compound including at least one of a polycarbonate group and a polyurethane group according to claim 6 , wherein the branching of the polymer chain takes place via at least one of the residues ST 1 or ST 2 .

8. The polyorganosiloxane compound including at least one of a polycarbonate group and a polyurethane group according to claim 1 , containing at least one polyorganosiloxane residue of the formula (2):

wherein

R 4 is a straight-chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon residue with up to 20 carbon atoms, and/or R 4 is an alkoxy residue, the alkyl part of which is a straight-chained, cyclic or branched, saturated alkyl residue with up to 20 carbon atoms, which may contain one or more oxygen atoms, and

s=1 to 999.

9. The polyorganosiloxane compound including at least one of a polycarbonate group and a polyurethane group according to claim 1 , containing at least two structural elements of the formula (1).

10. The polyorganosiloxane compound including at least one of a polycarbonate group and a polyurethane group according to claim 1 , containing at least two polyorganosiloxane residues of the formula (2).

11. The polyorganosiloxane compound including at least one of a polycarbonate group and a polyurethane group according to claim 1 , wherein Y=—NR 6 .

12. The polyorganosiloxane compound including at least one of a polycarbonate group and a polyurethane group according to according to claim 1 , wherein Y=—NH—.

13. The polyorganosiloxane compound including at least one of a polycarbonate group and a polyurethane group according to claim 1 , characterized in that it contains amino groups, protonated amino groups, quaternary ammonium groups and/or polyether groups.

14. The polyorganosiloxane compound including at least one of a polycarbonate group and a polyurethane group according to according to claim 1 , wherein ST 1 ≠ST 2 .

15. The polyorganosiloxane compound including at least one of a polycarbonate group and a polyurethane group according to according to claim 1 , wherein ST 1 contains a structural element of the following formula:

wherein s=1 to 999, and

r=1 to 12.

16. The polyorganosiloxane compound including at least one of a polycarbonate group and a polyurethane group according to claim 1 , wherein ST 2 represents a residue of the formula (5)

—ST 3 -N + (R 5 ) 2 —ST 4 -N + (R 5 ) 2 —ST 3 -+2A −   (5)

wherein

ST 3 is a di- or polyvalent, straight-chained or cyclic or branched, saturated or unsaturated or aromatic, substituted or unsubstituted hydrocarbon residue with 2 to 100 carbon atoms, which may contain —O—, —C(O)—, —NH— and/or —NR 3 —, and

ST 4 is a di- or polyvalent, straight-chained or cyclic or branched, saturated or unsaturated or aromatic, substituted or unsubstituted hydrocarbon residue with 2 to 100 carbon atoms, which may contain —O—, —C(O)—, —NH— and/or —NR 3 —, and/or a polyorganosiloxane unit with 2 to 500, and

A − is an organic or inorganic anion.

17. The polyorganosiloxane compound including at least one of a polycarbonate group and a polyurethane group according to claim 1 , having the following formula (3)

wherein

ST 4 is a di- or polyvalent, straight-chained or cyclic or branched, saturated or unsaturated or aromatic, substituted or unsubstituted hydrocarbon residue with 2 to 100 carbon atoms, which may contain —O—, —C(O)—, —NH—and/or —NR 3 —, and/or a polyorganosiloxane unit with 2 to 500,

A − is an organic or inorganic anion,

provided that at least one of the residues ST 1 , ST 3 and ST 4 contains a polyorganosiloxane residue.

18. The polyorganosiloxane compound including at least one of a polycarbonate group and a polyurethane group according to claim 1 , wherein at least one of ST 1 and ST 2 is selected from the group consisting of polyorganosiloxane-containing residues, polyether-containing residues, polyorganosiloxane- and polyether-containing residues, monocyclic or polycyclic hydrocarbon residues, acyclic, optionally oxygen-containing hydrocarbon residues and optionally oxygen-containing hydrocarbon residues comprising aromatic groups.

19. A composition comprising the polyorganosiloxane compound including at least one of a polycarbonate group and a polyurethane group according to claim 1 , wherein the composition is selected from the group consisting of coatings, agents for surface modification, elastomers, duromers, adhesives, primers for metal or plastic surfaces, polymer additives, laundry detergent additives, rheological agents, cosmetic agents, fiber modification agents.

20. The composition of claim 19 , wherein the composition is a modification agent for thermoplastic synthetic materials.

21. The composition of claim 20 , wherein the modification agents are low-temperature impact-resistance modifiers.

22. The composition of claim 20 , wherein the modification agent is selected from the group consisting of

viscosity regulators;

anti-static agents;

anti-fogging agents;

mixture components for silicone rubbers that can be cross-linked peroxidically or by hydrosilylation using platinum catalysis to form elastomers;

softeners for textile fibers for the treatment of textile fibers prior to, during and after washing,

agents for modifying fibers and fabrics selected from the group consisting of natural and synthetic fibers, hair, cotton fibers, synthetic fibers, polyester fibers, polyamide fibers, union fabric;

textile finishing agents;

softeners for detergent-containing formulations, and

laundry detergents and cleaning products.

Assignments (7)
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded May 4, 2023
From: JPMORGAN CHASE BANK, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063548/0281 →
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 →
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 →
SECURITY AGREEMENT Recorded Apr 29, 2011
From: MOMENTIVE PERFORMANCE MATERIALS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH; MOMENTIVE PERFORMANCE MATERIALS JAPAN LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 026204/0952 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 28, 2010
From: LANGE, HORST; WAGNER, ROLAND; HOFFMULLER, GUNNAR; SOCKEL, KARL-HEINZ; SIMON, WALTER
To: MOMENTIVE PERFORMACE MATERIALS GMBH
Reel/Frame 025208/0186 →