Aromatic enol ether paint additives

Patent metadata

Field	Value
Publication number	US-11518899-B2
Application number	US-201916559859-A
Country	US
Kind code	B2
Filing date	Sep 4, 2019
Priority date	Sep 4, 2019
Publication date	Dec 6, 2022
Grant date	Dec 6, 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

wherein ** indicates the point of attachment; and
R 1a is

R 2 is a (C 5-10 ) aryl;
R 3 is a (C 1-10 )alkyl or a (C 5-10 ) aryl;
R 4 is hydrogen, a (C 1-12 ) alkyl, a (C 2-12 ) alkenyl, or —C(O)R 5 ;
R 5 is a (C 1-12 ) alkyl unsubstituted or substituted by R 6 , a (C 2-12 ) alkenyl unsubstituted or substituted by R 6 , a (C 3-8 ) cycloalkyl, or a 5- to 9-membered aryl;
R 6 is a (C 1-4 ) alkoxy, or an oxo; and
n is an integer from 1 to 15.

2. The aromatic enol ether of claim 1 wherein R 2 is phenyl, substituted phenyl, naphthyl, substituted napththyl, furanyl, or substituted furanyl.

3. The aromatic enol ether of claim 1 wherein R 3 is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, phenyl, substituted phenyl, naphthyl, substituted napththyl, furanyl, or substituted furanyl.

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 R 2 is phenyl or substituted phenyl; R 3 is methyl, ethyl, phenyl, or substituted phenyl and n is an integer from 1 to 4.

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

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

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

9. The coating composition of claim 1 wherein said 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.

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

wherein: each A is, independently,

and
wherein ** indicates the point of attachment;
R 1c is

each R 2 is, independently, a (C 5-10 ) aryl;
each R 3 is, independently a (C 1-10 ) alkyl or a (C 5-10 ) aryl; and
n is an integer from 1 to 15;
or mixtures thereof.

11. The aromatic enol ether of claim 7 wherein R 2 is phenyl, substituted phenyl, naphthyl, substituted napththyl, furanyl, or substituted furanyl.

12. The aromatic enol ether of claim 7 wherein R 3 is methyl, ethyl, propyl, butyl, pentyl, heptyl, hexyl, heptyl, octyl, nonyl, decyl, phenyl, substituted phenyl, naphthyl, substituted napththyl, furanyl, or substituted furanyl.

13. The aromatic enol ether of claim 7 wherein R 2 is phenyl or substituted phenyl, R 3 is methyl, ethyl, phenyl, or substituted phenyl and n is an integer from 1 to 3.

14. The aromatic enol ether of claim 7 wherein said composition has a volatile organic content of less than 50 wt % according to ASTM D6886.

15. The coating composition of claim 7 wherein said latex compound is an acrylic polymer, a vinyl acrylic polymer, a styrene butadiene polymer or a styrene acrylic latex polymer, or a mixture thereof.

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

17. The coating composition of claim 7 wherein said 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, ethyl acrylamide, or 2-hydroxyethyl methacrylate phosphate polymer or mixture thereof.

18. A coating composition comprising:
a. at least one latex compound; and
b. at least one aromatic enol ether selected from the group consisting of:

and isomers thereof.

19. 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

wherein ** indicates the point of attachment; and
R 1a is

R 2 is a (C 5-10 ) aryl;
R 3 is a (C 1-10 ) alkyl or a (C 5-10 ) aryl;
R 4 is hydrogen, a (C 1-12 ) alkyl, a (C 2-12 ) alkenyl, or —C(O)R 5 ;
R 5 is a (C 1-12 ) alkyl unsubstituted or substituted by R 6 , a (C 2-12 ) alkenyl unsubstituted or substituted by R 6 , a (C 3-8 ) cycloalkyl, or a 5- to 9-membered aryl;
R 6 is a (C 1-4 ) alkoxy, or an oxo; and
n is an integer from 1 to 15.

20. 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 II:

Assignees

• Eastman Chem Co

Inventors

• Boone Matthew Allen
• Czirr Dustin John

Classifications

• C09D7/63

  organic · CPC title

• C09D5/024 Primary

  characterised by the additives · CPC title

• C09D7/20

  Diluents or solvents · CPC title

• C09D7/65

  macromolecular (C09D7/41-C09D7/48 take precedence) · CPC title

• C09D113/02 Primary

  Latex · CPC title