IP Library Granted Patent US 8,748,542
Granted Patent B2
US 8,748,542 · App. 12/487,297 · Granted Jun 10, 2014

Colorant compatible hydrophobically modified polyurethane thickener for paint

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Quick Facts
Patent No.
US 8,748,542
App. No.
12/487,297
Granted
Jun 10, 2014
Kind
B2
Abstract

A synthetic polymer has a water-soluble or water-swellable polyurethane backbone and terminal groups and/or intermediate groups of blocks of hydrophobes of alkyl- or aryl compounds containing a polymerizable cyclic monomer or a polymerizable double bond (or alkene) group or derivatives thereof. The blocks of hydrophobes are composed of two or more units of the same or different hydrophobes. These synthetic polymers are used as rheology modifiers, especially in latex paints.

Claims (35)

1. A polymer composition comprising a water soluble or water swellable polyurethane having covalently connected ends of oligomeric hydrophobe blocks of the following formula:

where:

a) n is an integer from 1-100

b) R is an alkyl or aryl group having from 2 to 100 carbons,

c) A is a connecting diradical selected from the group consisting of —O—CH 2 —,

d) B is a connecting group selected from the group consisting of —OCH 2 —,

e) C is a connecting end equal to: —OH or —C 6 H 13 ; and

wherein the water soluble or water swellable polyurethane is free of internal pendant hydrophobes.

2. The composition of claim 1 , wherein n has a lower limit of 3.

3. The composition of claim 1 , wherein n has an upper limit of 75.

4. The composition of claim 1 , wherein R is an alkyl group that is selected from the group consisting of saturated, unsaturated, non cyclic, linear, branched, and halogenated alkyl groups.

5. The composition of claim 1 , wherein when the alkyl is a halogenated alkyl, it is selected from the group consisting of fluorinated, chlorinated, and brominated alkyls.

6. The composition of claim 1 , wherein the alkyl and aryl groups are substituted and are selected from the group consisting of alkylsiloxane, alkylether, arylalkylether, alkylarylene ether, alkylene ether, alkyl thioether, alkylene thioether, alkyl amine, dialkyl amine, dialkyl amine oxide, triakyl ammonium, diaryl amine, dialkyl phosphine, diaryl phosphine, dialkyl phosphine oxide, diaryl phosphine oxide, and dialkyl phosphate.

7. The composition of claim 1 , wherein A —OCH 2 —, B=—O—CH 2 —, R=—CH 2 O—C 8 H 18 and, C=—OH.

8. The composition of claim 1 , wherein A=—OCH 2 —, B=—OCH 2 —, C=—C 6 H 13 , and R=—OC 6 H 5 .

9. A process for preparing the water soluble or water swellable polyurethane of claim 1 comprising the steps of:

a) reacting a water soluble or water swellable polymer backbone with a catalyzing agent thereby activating the polymer backbone and providing a reaction mass;

b) adding at least one oligomerizing hydrophobic monomer to the reaction mass; and

c) polymerizing the reaction mass at sufficient temperature and for a sufficient time in order to add at least one oligomerizing hydrophobic monomer to the polymer backbone as end groups,

wherein the water soluble or water swellable polyurethane is free of internal pendant hydrophobes.

10. The process of claim 9 , wherein the oligomerizing hydrophobic monomers are selected from the group consisting of alkyl and aryl moieties containing a polymerizable cyclic monomer wherein the blocks are two or more units of the same or different hydrophobic monomers.

11. The process of claim 10 , wherein the oligomerizing hydrophobic monomer is selected from alkyl moieties containing a polymerizable cyclic monomer where the alkyl group has 1 to 40 carbons.

12. The process of claim 10 , wherein the hydrophobic group is selected from aryl moieties containing a polymerizable cyclic monomer where the aryl has 6 to 40 carbons.

13. The process of claim 9 , wherein the polymer prepared by the process has a weight average molecular weight with an upper limit of about 10,000,000.

14. The process of claim 9 , wherein the polymer prepared by the process has a weight average molecular weight with a lower limit of about 400.

15. The process of claim 10 , wherein the oligomeric hydrophobe blocks are oligomers of a polymerizable cyclic monomer or a mixture thereof bearing alkyl or aryl groups with the total number of carbons being from 1 to 100.

16. The process of claim 10 , wherein the polymerizable cyclic monomers are selected from the group consisting of alkyl glycidyl ethers, aryl glycidyl ethers, alkyl epoxide, aryl alkyl epoxide, alkyl oxazoline, aryl oxazoline, and mixture thereof.

17. An aqueous protective coating composition comprising (a) the composition of claim 1 , (b) a colorant, and (c) a film forming latex, wherein the viscosity of the coating composition remains unchanged or has an insignificant loss as compared to when using conventional rheology modifiers upon adding a colorant.

18. The aqueous protective coating composition of claim 17 , wherein the composition is a latex paint.

19. The aqueous protective coating composition of claim 17 , wherein the latex is selected from the group consisting of acrylics, vinyl acrylics, and styrene.

20. The aqueous protective coating composition of claim 19 , wherein the latex paint has a pigment volume concentration of from about 15 to about 80.

21. An aqueous protective coating composition comprising a) the polymer composition of claim 1 , b) at least one thickener selected from the group consisting of HEUR, HASE, cellulose derivative, and polyacetalpolyether, c) a colorant, and d) a film forming latex.

22. The aqueous protective coating composition of claim 21 , wherein the cellulose derivative is selected from the group consisting of hydroxyethylcellulose (HEC), hydroxypropyl cellulose (HPC), methylcellulose (MC), carboxymethylcellulose (CMC), methylhydroxy ethylcellulose (MHEC), ethylhydroxyethylcellulose (EHEC), and hydrophobically modified hydroxyethylcellulose (HMHEC).

23. The composition of claim 1 , wherein the upper limit of the weight average molecular weight of the polymer is about 10,000,000.

24. The composition of claim 1 , wherein the lower limit of the weight average molecular weight of the polymer is about 400.

Assignments (9)
RELEASE OF SECURITY INTEREST Recorded Jan 10, 2020
From: THE BANK OF NOVA SCOTIA
To: AVOCA LLC; HERCULES LLC; ISP INVESTMENTS LLC; PHARMACHEM LABORATORIES LLC
Reel/Frame 051557/0504 →
SECURITY AGREEMENT Recorded Jul 3, 2017
From: AVOCA, INC.; HERCULES LLC; ISP INVESTMENTS LLC; PHARMACHEM LABORATORIES, INC.
To: THE BANK OF NOVA SCOTIA, AS ADMINISTRATIVE AGENT
Reel/Frame 043084/0753 →
CHANGE OF NAME Recorded May 18, 2017
From: HERCULES INCORPORATED
To: HERCULES LLC
Reel/Frame 042497/0331 →
RELEASE OF PATENT SECURITY AGREEMENT Recorded Mar 18, 2013
From: THE BANK OF NOVA SCOTIA
To: ASHLAND LICENSING AND INTELLECTUAL PROPERTY LLC; AQUALON COMPANY; ISP INVESTMENTS INC.; HERCULES INCORPORATED
Reel/Frame 030025/0320 →
SECURITY AGREEMENT Recorded Sep 16, 2011
From: ASHLAND LICENSING AND INTELLECTUAL PROPERTY LLC; HERCULES INCORPORATED; AQUALON COMPANY; ISP INVESTMENT INC.
To: THE BANK OF NOVA SCOTIA, AS ADMINISTRATIVE AGENT
Reel/Frame 026918/0052 →
RELEASE OF PATENT SECURITY AGREEMENT Recorded Sep 15, 2011
From: BANK OF AMERICA, N.A.
To: ASHLAND, INC.; ASHLAND LICENSING AND INTELLECTUAL PROPERTY LLC; AQUALON COMPANY; HERCULES INCORPORATED
Reel/Frame 026927/0247 →
SECURITY AGREEMENT Recorded Apr 14, 2010
From: ASHLAND LICENSING AND INTELLECTUAL PROPERTY LLC; AQUALON COMPANY; HERCULES INCORPORATED
To: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 024225/0289 →
RELEASE OF SECURITY INTEREST Recorded Apr 13, 2010
From: BANK OF AMERICA, N.A., AS COLLATERAL AGENT
To: ASHLAND LICENSING AND INTELLECTUAL PROPERTY LLC; AQUALON COMPANY; HERCULES INCORPORATED
Reel/Frame 024218/0928 →
SUPPLEMENTAL PATENT SECURITY AGREEMENT Recorded Nov 23, 2009
From: HERCULES INCORPORATED
To: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 023559/0122 →