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1. WO2021046037 - AROMATIC ENOL ETHER PAINT ADDITIVES

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[ EN ]

CLAIMS

We claim:

1 . A coating composition comprising:

a. at least one latex compound; and

b. at least one aromatic enol ether having Formula I:


I

wherein:

A is (Ce-2o) alkylaryl;

R1 a and R1b are independently


each R4 is independently (Ci-i2)alkyl, or -C(0)R5;

each R5 is (Ci-i2)alkyl unsubstituted or substituted by R6, (C2-i2)alkenyl unsubstituted or substituted by R6, (C3-8)cycloalkyl, or 5- to 9- membered aryl;

each R6 is (Ci-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 R4 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 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.

6. The coating composition of claim 5 wherein said latex compound has a Tg in the range of from about -20°C to about 100°C.

7. 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.

8. A coating composition comprising:

a. at least one latex compound; and

b. at least one aromatic enol ether having Formula II:


II

wherein A is (C8-2o)alkylaryl;

R1 a and R1b are independently


each R4 is independently hydrogen, (Ci-i2)alkyl, (C2-i2)alkenyl or - C(0)R5; each R5 is (Ci-i2)alkyl unsubstituted or substituted by R6, (C2- i2)alkenyl unsubstituted or substituted by R6, (C3-8)cycloalkyl, or 5- to 9- membered aryl; R6 is (Ci-4)alkoxy, or oxo; and each n is independently an integer from 1 to 15.

9. The aromatic enol ether of claim 8 wherein A is 1 ,2-, 1 ,3-, or 1 ,4-disubstituted phenyl.

10. The aromatic enol ether of claim 8 wherein R4 is hydrogen or an ethyl group.

11 . The coating composition of claim 8 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.

12. The coating composition of claim 8 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.

13. A coating composition comprising:

a. at least one latex compound; and

b. at least one aromatic enol ether having Formula III:


III

wherein: A is (C8-20) alkylaryl;

R1 a and R1b are independently


each R4 is independently (Ci-i2)alkyl, or -C(0)R5;

each R5 is (Ci-i2)alkyl unsubstituted or substituted by R6, (C2-i2)alkenyl unsubstituted or substituted by R6, (C3-8)cycloalkyl, or 5- to 9-membered aryl;

each R6 is (Ci-4)alkoxy, or oxo; and

each n is independently an integer from 1 to 15.

14. The aromatic enol ether of claim 8 wherein A is 1 ,2-, 1 ,3-, or 1 ,4-disubstituted phenyl.

15. The aromatic enol ether of claim 8 wherein R4 is hydrogen or an ethyl group.

16. The coating composition of claim 8 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.

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

18. The coating composition of claim 8 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.

19. A coating composition comprising:

a. at least one latex compound; and

b. at least one aromatic enol ether selected from the group consisting of compositions 5-19:


10


5


and isomers thereof.

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 I,


I

wherein: A is (Ce-2o) alkylaryl;

R1 a and R1b are independently


each R4 is independently (Ci-i2)alkyl, or -C(0)R5;

each R5 is (Ci-i2)alkyl unsubstituted or substituted by R6, (C2-i2)alkenyl unsubstituted or substituted by R6, (C3-8)cycloalkyl, or 5- to 9- membered aryl;

each R6 is (Ci-4)alkoxy, or oxo; and

each n is independently an integer from 1 to 1 ; or

wherein said aromatic enol ether has a Formula II,


II

wherein: A is (C8-20) aryl;

R1 a and R1b are independently


each R4 is independently (Ci-i2)alkyl, or -C(0)R5;

each R5 is (Ci-i2)alkyl unsubstituted or substituted by R6, (C2-i2)alkenyl unsubstituted or substituted by R6, (C3-8)cycloalkyl, or 5- to 9- membered aryl;

each R6 is (Ci-4)alkoxy, or oxo; and

each n is independently an integer from 1 to 15; or.

wherein said aromatic enol ether has a Formula III:


III

wherein: A is (C8-20) alkylaryl;

R1 a and R1b are independently


each R4 is independently (Ci-i2)alkyl, or -C(0)R5;

each R5 is (Ci-i2)alkyl unsubstituted or substituted by R6, (C2-i2)alkenyl unsubstituted or substituted by R6, (C3-8)cycloalkyl, or 5- to 9-membered aryl; each R6 is (Ci-4)alkoxy, or oxo; and

each n is independently an integer from 1 to 15; or

mixtures thereof.