IP Library Patent Application 14427585
Patent Application
App. No. 14/427,585

AQUEOUS POLYURETHANE DISPERSION DERIVED FROM TERTIARY ALKENYL GLYCIDYL ESTERS

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Patent No.
US None
App. No.
14/427,585
Abstract

This invention relates to a Waterborne Polyurethane Dispersions (WPU) derived from the reaction products of tertiary alkyl glycidyl esters based hydroxyl terminal polyester polyols with polyisocyanates and chain extended with poly-functional amines and dispersed in water have shown the surprising inherent ability for self-coalescence. Furthermore the cured films have shown improved hardness and abrasion resistance over these benchmarks with a significant reduction in coalescing solvent needed to accomplish film formation.

Claims (20)

1 . A polyurethane aqueous dispersion composition comprising a hydroxyl terminal oligomer derived from an alkyl glycidyl ester and carboxylic di-acids and anhydride hemi-ester, wherein the di-acid, the anhydride or the hemi-ester are not derived from unsaturated fatty acids, and a poly-isocyanate and a water dispersing component and a chain extender component, wherein the oligomer is characterized in that the molecular weight is between 600 and 5000, and free of meth(acrylic) derivatives.

2 . The composition of claim 1 wherein the alkyl glycidyl ester is a linear or branched alkyl glycidyl ester with an alkyl group containing from 4 to 12 carbon atoms.

3 . The composition of claims 2 wherein the alkyl glycidyl ester is a branched alkyl glycidyl ester having a tertiary alkyl chain with 4 to 12 carbon atoms.

4 . The composition of claim 1 wherein the polyisocyanate may be dicyclohexylmethane diisocyanate, isophorone diisocyanate, hexane diisocyanate, tetramethylxylene diisocyanate, toluene diisocyanate, diphenylmethane diisocyanate, or, combinations thereof.

5 . The composition of claim 1 wherein the polyisocyanate is present in an amount of between 25 to 50 weight % based on total polyurethane solids content.

6 . The composition of claim 1 wherein the polyisocyanate present in an amount of between 27 to 48 weight % based upon total polyurethane solids content.

7 . The composition of claim 1 wherein the water dispersing component may be anionic or cationic or nonionic or combinations thereof.

8 . The composition of claim 1 wherein a polyol component is comprised of a hydroxyl terminal oligomer derived from an alkyl glycidyl ester and carboxylic di-acids and anhydride, wherein the alkyl chain is a tertiary alkyl chain with 4 to 12 carbon atoms.

9 . The composition of claim 8 wherein the polyol may be used as a mixture with general classes of polyols and glycols such as polyesters, polycaprolactones, polycarbonates, polyethers, short chain glycols.

10 . The composition of claim 8 wherein the polyol component is between 25 to 60 weight % based upon total polyurethane solids content.

11 . The composition of claim 1 wherein the chain extender component may be selected from aliphatic polyfunctional amines, aromatic polyfunctional amines, blocked amines, amino alcohols, polyether amines, and water.

12 . The composition of claim 1 wherein a co-solvent is present in an amount lower than 25.5 weight % based on total polyurethane solids content.

13 . The composition of claim 1 wherein the composition is preferably free of n-methylpyrolidone.

14 . The composition of claim 1 wherein the molecular weight is between 800 and 3500.

15 . The composition of claim 8 comprising 25-50 weight % diisocyanate, 25-60 weight % polyol component.

16 . The composition of claim 12 wherein the weight % level of cosolvent required for film formation at 25° C. of the resulting polyurethane polymer is 35 to 60% lower than stochiometrically equivalent polyurethane systems utilizing hexane-neopentyl adipate polyester or BDO initiated polycaprolactone or CHDM initiated polycarbonate as the polyol component.

17 . The composition of claim 1 wherein a Koenig Hardness of the resulting polyurethane polymer is 83 to 124% higher than stochiometrically equivalent polyurethane systems utilizing hexane-neopentyl adipate polyester or BDO initiated polycaprolactone as the polyol component.

18 . The composition of claim 1 17 wherein a Koenig Hardness of the resulting polyurethane polymer is 2 to 3% higher, and, the weight % level of cosolvent required for film formation at 25° C. of the resulting polyurethane polymer is 55 to 60% lower than stochiometrically equivalent polyurethane systems utilizing CHDM initiated polycarbonate as the polyol component.

19 . The composition of claim 16 wherein a Taber Abrasion resistance measured as mg loss/1000 cycles yields between 49 to 84% reduction in mg loss comparative to stochiometrically equivalent polyurethane systems utilizing hexane-neopentyl adipate polyester or BDO initiated polycaprolactone as the polyol component.

20 . The composition of claim 16 wherein a Taber Abrasion resistance measured as mg loss/1000 cycles yields between 10 to 15% reduction in mg loss comparative to stochiometrically equivalent polyurethane systems utilizing CHDM initiated polycarbonate as the polyol component.

Assignments (11)
RELEASE OF SECURITY INTEREST IN PATENTS (ABL) RECORDED AT REEL/FRAME 049740/0770 Recorded Mar 18, 2022
From: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
To: HEXION INC.
Reel/Frame 059435/0490 →
RELEASE OF SECURITY INTEREST IN PATENTS (TERM LOAN) RECORDED AT REEL/FRAME 049741/0425 Recorded Mar 18, 2022
From: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
To: HEXION INC.
Reel/Frame 059435/0473 →
PATENT SECURITY INTEREST (ABL) Recorded Jul 12, 2019
From: HEXION INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 049740/0770 →
PATENT SECURITY INTEREST (TERM LOAN) Recorded Jul 12, 2019
From: HEXION INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 049741/0425 →
PATENT SECURITY INTEREST ASSIGNMENT AGREEMENT Recorded Apr 3, 2019
From: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS THE PRIOR COLLATERAL AGENT
To: WILMINGTON SAVINGS FUND SOCIETY, FSB, AS THE CURRENT COLLATERAL AGENT
Reel/Frame 048788/0617 →
RELEASE OF SECURITY INTEREST Recorded Feb 23, 2017
From: WILMINGTON TRUST, NATIONAL ASSOCIATION
To: HEXION INC.
Reel/Frame 041793/0920 →
SECURITY INTEREST Recorded Feb 13, 2017
From: HEXION INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 041693/0888 →
SECURITY INTEREST Recorded Feb 2, 2016
From: HEXION INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 037639/0795 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 7, 2015
From: STEINBRECHER, CHRISTOPHE; HEYMANS, DENIS; ERDEM, BEDRI; O'SHAUGNESSY, MIKE; BLAISDELL, JEFF
To: HEXION INC.
Reel/Frame 036012/0100 →
SECURITY INTEREST Recorded Jun 8, 2015
From: HEXION INC.
To: WILMINGTON TRUST COMPANY, AS COLLATERAL AGENT
Reel/Frame 035801/0372 →
SECURITY INTEREST Recorded Jun 8, 2015
From: HEXION INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 035848/0705 →