Aromatic enol ether paint additives

Patent metadata

Field	Value
Publication number	US-11312873-B2
Application number	US-201916559880-A
Country	US
Kind code	B2
Filing date	Sep 4, 2019
Priority date	Sep 4, 2019
Publication date	Apr 26, 2022
Grant date	Apr 26, 2022

Abstract

Disclosed are aromatic enol ethers that have utility as film-hardening additives for coating formulations. The aromatic enol ethers have particular utility as film-hardening additives for water-based coating formulations. The aromatic enol ethers provide improvements in hardness and hardness related properties such as block resistance without contributing to the volatile organic content of the composition.

First claim

We claim:

1. A coating composition comprising:
a. at least one latex compound; and
b. at least one aromatic enol ether having Formula I:

wherein:
A is (C 8-20 ) alkylaryl;
R 1a and R 1b are independently

each R 4 is independently, hydrogen, (C 1-12 )alkyl, (C 2-12 )alkenyl or —C(O)R 5 ;
each R 5 is (C 1-12 )alkyl unsubstituted or substituted by R 6 , (C 2-12 )alkenyl unsubstituted or substituted by R 6 , (C 3-8 )cycloalkyl, or 5- to 9-membered aryl;
each R 6 is (C 1-4 )alkoxy, or oxo; and
each n is independently an integer from 1 to 15.

2. The aromatic enol ether of claim 1 wherein A is 1,2-, 1,3-, or 1,4-disubstituted phenyl.

3. The aromatic enol ether of claim 1 wherein R 4 is hydrogen or an ethyl group.

4. The aromatic enol ether of claim 1 wherein, n is an integer from 1 to 4.

5. The aromatic enol ether of claim 1 wherein the composition has a volatile organic content of less than 50 wt % according to ASTM D6886.

6. The coating composition of claim 1 wherein said at least one latex compound is an acrylic polymer, a vinyl acrylic polymer, a styrene butadiene polymer or a styrene acrylic latex polymer, or a mixture thereof.

7. The coating composition of claim 6 wherein said at least one latex compound has a Tg in the range of from about −20° C. to about 100° C.

8. The coating composition of claim 1 wherein said at least one latex compound is a styrene, methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, butyl acrylate, butyl methacrylate, isobutyl acrylate, isobutyl methacrylate, ethylhexyl acrylate, 2-ethylhexyl methacrylate, 2-ethylhexyl acrylate, isoprene, octyl acrylate, octyl methacrylate, iso-octyl acrylate, iso-octyl methacrylate, acrylic acid, methacrylic acid, itaconic acid, crotonic acid, O-methyl styrene, vinyl naphthalene, vinyl toluene, chloromethyl styrene, hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, acrylonitrile, glycidyl methacrylate, acetoacetoxyethyl methacrylate, acetoacetoxy ethyl acrylate, vinyl chloride, vinylidene chloride, vinyl acetate, butyl acrylamide, or ethyl acrylamide polymer or mixture thereof.

9. A method of improving the performance properties of a cured paint without contributing to the volatile organic content of the paint formula comprising adding an aromatic enol ether to said paint, wherein said aromatic enol ether has a Formula I,

wherein: A is (C 8-20 ) alkylaryl;
R 1a and R 1b are independently

each R 4 is independently (C 1-12 )alkyl, or —C(O)R 5 ;
each R 5 is (C 1-12 )alkyl unsubstituted or substituted by R 6 , (C 2-12 )alkenyl unsubstituted or substituted by R 6 , (C 3-8 )cycloalkyl, or 5- to 9-membered aryl;
each R 6 is (C 1-4 )alkoxy, or oxo; and
each n is independently an integer from 1 to 1.

Assignees

• Eastman Chem Co

Inventors

• Boone Matthew Allen
• Czirr Dustin John

Classifications

• C09D7/63 Primary

  organic · CPC title

• C08L9/04

  Latex · CPC title

• C08K5/06

  Ethers; Acetals; Ketals; Ortho-esters · CPC title

• C08L33/14

  of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen · CPC title

• C07C43/166

  having unsaturation outside the aromatic rings · CPC title