# US 10,865,172 B1 · Aromatic enol ethers

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- Number: US 10,865,172 B1
- Document ID: US10865172B1
- Status: Granted
- Kind: B1
- Application number: 16/559,871
- Filed: 2019-09-04
- Granted: 2020-12-15
- Earliest claimed: 2019-09-04
- Assignees: Eastman Chemical Company
- Applicants: Eastman Chemical Company
- Inventors: Matthew Allen Boone
- Web page: https://patentgrep.com/patent/US10865172B1

## CPC

- C07C 43/166: having unsaturation outside the aromatic rings
- C09D 7/63: organic
- C09D 7/65: macromolecular (C09D7/41-C09D7/48 take precedence)
- C08K 5/06: Ethers; Acetals; Ketals; Ortho-esters
- C08L 9/04: Latex
- C08L 9/08: Latex
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## 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.

## Claims

### Claim 1

A compound according to Formula I:
wherein:
A is (C8-20) alkylaryl;
R1a and R1b are independently
each R4 is independently hydrogen, (C1-12)alkyl, or —C(O)R5;
each R5 is (C1-12)alkyl unsubstituted or substituted by R6, (C2-12)alkenyl unsubstituted or substituted by R6, (C3-8)cycloalkyl, or 5- to 9-membered aryl;
each R6 is (C1-4)alkoxy, or oxo; and
each n is independently an integer from 1 to 15.

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 1)

The compound of claim 1 wherein R4 is hydrogen or ethyl.

### Claim 4 (depends on 1)

The compound of claim 1 wherein, n is an integer from 1 to 4.

### Claim 5 (depends on 1)

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

### Claim 6

A compound according to Formula II:
wherein:
A is (C8-20) aryl;
R1a and R1b are independently
each R4 is independently (C1-12)alkyl, or —C(O)R5;
each R5 is (C1-12)alkyl unsubstituted or substituted by R6, (C2-12)alkenyl unsubstituted or substituted by R6, (C3-8)cycloalkyl, or 5- to 9-membered aryl;
each R6 is (C1-4)alkoxy, or oxo; and
each n is independently an integer from 1 to 15.

### Claim 7 (depends on 6)

The compound of claim 6 wherein A is 1,2-, 1,3-, or 1,4-disubstituted phenyl.

### Claim 8 (depends on 6)

The compound of claim 6 wherein R4 is hydrogen or ethyl.

### Claim 9 (depends on 6)

The compound of claim 6 wherein, n is an integer from 1 to 4.

### Claim 10 (depends on 6)

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

### Claim 11

A compound according to Formula III:
wherein:
A is (C8-20) alkylaryl;
R1a and R1b are independently
each R4 is independently (C1-12)alkyl, or —C(O)R5;
each R5 is (C1-12)alkyl unsubstituted or substituted by R6, (C2-12)alkenyl unsubstituted or substituted by R6, (C3-8)cycloalkyl, or 5- to 9-membered aryl;
each R6 is (C1-4)alkoxy, or oxo; and
each n is independently an integer from 1 to 15.

### Claim 12 (depends on 11)

The compound of claim 11 wherein A is 1,2-, 1,3-, or 1,4-disubstituted phenyl.

### Claim 13 (depends on 11)

The compound of claim 11 wherein R4 is hydrogen or ethyl.

### Claim 14 (depends on 11)

The compound of claim 11 wherein, n is an integer from 1 to 4.

### Claim 15 (depends on 11)

The compound of claim 11 wherein the composition has a volatile organic content of less than 50 wt % according to ASTM D6886.

### Claim 16

An enol ether compound selected from the group consisting of compositions having Formulas 5-19:
and isomers thereof.