IP Library Granted Patent US 9,957,243
Granted Patent B2
US 9,957,243 · App. 15/233,318 · Granted May 1, 2018

Vinyl-containing compounds and processes for making the same

Inventors: Hildeberto Nava (Cary, NC); Yongning Liu (Apex, NC)
Assignee: Reichhold LLC 2
C07D301/00C07C67/08C07C67/30C08G63/47C08G63/914
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 9,957,243
App. No.
15/233,318
Granted
May 1, 2018
Kind
B2
Abstract

The present invention provides a process for forming vinyl-containing compounds including the steps of: a) reacting in a nitrogen atmosphere a dicarboxylic acid and/or anhydride and a functional mono or polyfunctional alcohol to provide a hydroxyl-containing polyester; b) reacting the hydroxyl-containing polyester with a vinyl-containing organic acid in the presence of an esterification catalyst, a polymerization inhibitor and an azeotropic agent; and c) reacting the vinyl functional esterified intermediate, residual esterification catalyst and residual vinyl-containing organic acid with an epoxy to provide the vinyl-containing compound.

Claims (13)

1. A process for forming vinyl-containing compounds, the process comprising the steps of:

a) reacting in an inert nitrogen atmosphere at least one dicarboxylic acid and/or anhydride and a monofunctional or polyfunctional alcohol to an endpoint of an acid number of 10 or less to provide a hydroxyl-containing polyester;

b) reacting the hydroxyl-containing polyester with a vinyl-containing organic acid in the presence of an esterification catalyst, a polymerization inhibitor and an azeotropic agent while in the inert nitrogen atmosphere to provide a vinyl functional esterified intermediate group; and

c) reacting the vinyl functional esterified intermediate, residual esterification catalyst and residual vinyl-containing organic acid with an epoxy while in the inert nitrogen atmosphere to provide the vinyl-containing compound wherein the nitrogen atmosphere in steps a)-c) is devoid of oxygen and the reactions are under inert conditions.

2. The process according to claim 1 , wherein the at least one dicarboxylic acid is selected from the group consisting of isophthalic acid, terephthalic acid, adipic acid, cyclohexane dicarboxylic acid, succinic anhydride, sebacic acid, azealic acid, malonic acid, and alkenyl succininc acids, and anhydrides thereof.

3. The process according to claim 2 , wherein the anhydride of the dicarboxylic acid is selected from the group consisting of phthalic anhydride, tetrahydrophthalic anhydride, and hexahydrophthalic anhydride.

4. The process according to claim 1 , wherein the alcohol is selected from the group consisting of n-butanol, n-hexanol, octanol, undecanol, dodecanol, cyclohexylmethanol, benzyl alcohol, phenoxy ethanol, ethylene glycol, diethylene glycol, neopentyl glycol, dibromoneopentyldiol, polytetramethylene glycol, 1,5-pentanediol, 1,4-butanediol, 2-methyl propanediol, 2,2,4-trimethyl-1,3pentadiol, 2-butyl-2ethyl-1,3-propanediol, ethoxylated hydrogenated bisphenol “A”, 1,4-cyclohexane dimenthanol, sorbitol, 1,2,3,6-hexatetrol, 1,4-sorbitol, pentaerythritol, dipentaerythritol, tripentaerythritol, sucrose, 1,2,4-butanetriol, 1,2,5-pentanetriol, glycerol, 2-methyl propanetriol, 2-methyl-1,2,4-butanetriol, trimethylol ethane, trimethylol propane, 1,3,5-trihydroxyethyl benzene, polyTHF, polyethyleneoxide, and polypropyleneoxide, catechol, resorcinol, and bisphenol intermediates, and mixtures thereof.

5. The process according to claim 1 , wherein the vinyl-containing organic acid is selected from the group consisting of methacrylic acid or acrylic acid.

6. The process according to claim 1 , wherein the epoxy is selected from the group consisting of Bisphenol A epoxy, Bisphenol F epoxy, butyl glycidyl ether, C12-C14 glycidyl ether, cresyl glycidyl ether, glycidyl neodecanoate, diglycidyl ether of neopentyl glycol, diglycidyl ether of 1,4 butanediol, and diglycidyl ether of resorcinol.

7. The process according to claim 1 , wherein a second esterification catalyst is added with the epoxy in step (c).

8. The process according to claim 1 , wherein the second esterification catalyst is selected from the group consisting of orgenophosphonium salts and quaternary ammonium salts.

9. A gelcoat having light color and comprising the vinyl-containing compound prepared by the process of claim 1 .

10. The gelcoat of claim 9 having at least viscosity stability, molecular weight stability and color stability at 65° C. for at least 60 days.

Assignments (5)
MERGER Recorded Jan 28, 2025
From: REICHHOLD LLC 2
To: POLYNT COMPOSITES USA INC.
Reel/Frame 070029/0209 →
SECURITY INTEREST Recorded Mar 1, 2022
From: REICHHOLD LLC 2
To: BNY MELLON CORPORATE TRUSTEE SERVICES LIMITED, AS SECURITY AGENT
Reel/Frame 059133/0612 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 28, 2017
From: REICHHOLD LIQUIDATION, INC.
To: REICHHOLD LLC 2
Reel/Frame 044498/0770 →
CHANGE OF NAME Recorded Sep 22, 2017
From: REICHHOLD, INC.
To: REICHHOLD LIQUIDATION, INC.
Reel/Frame 043978/0363 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 10, 2016
From: NAVA, HILDEBERTO; LIU, YONGNING
To: REICHHOLD, INC.
Reel/Frame 039396/0163 →
Continuity (3)
Continuation 13024547 · Feb 10, 2011
Provisional Application 61307486 · Feb 24, 2010
Related Publication 20160355490A1 · Dec 8, 2016