Weatherable and durable coating compositions

Patent metadata

Field	Value
Publication number	US-11932775-B2
Application number	US-201917253343-A
Country	US
Kind code	B2
Filing date	Jul 17, 2019
Priority date	Jul 19, 2018
Publication date	Mar 19, 2024
Grant date	Mar 19, 2024

Abstract

A curable coating composition is provided having multi-functionalized acrylic copolymer and silicone imine resin curing agents. The acrylic copolymer of the curable coating composition has, in polymerized form, epoxy functionalized groups and cure compatibility groups and the silicone imine forms an amino-functional silicone in the presence of water. The coating compositions are useful in the field of superior weatherable and durable coatings and are useful to replace isocyanate-containing polyurethane based coatings. Also provided are coated articles produced from the curable composition.

First claim

The invention claimed is:

1. A curable coating composition comprising:
(1) a silicone imine resin which in the presence of sufficient amounts of water forms an amino-functional silicone resin of the fully condensed formula
R x SiO (4-x)/2 where
(a) x is a number from 1.0 to 2.1;
(b) the amino-functional silicone resin is comprised of the Si units R 3 SiO 1/2 , R 2 SiO 2/2 , RSiO 3/2 , and SiO 4/2 in polymerized form, where at least 5 mole percent of the total amount of Si units of the amino-functional silicone resin comprise (i) RSiO 3/2 groups, (ii) SiO 4/2 groups or (iii) mixtures thereof;
(c) each R is independently an alkyl group, an aryl group, or an amino-functional hydrocarbyl group, provided that the —NH— equivalent mass of the amino-functional silicone resin is from 50 to 750; and

(2) an acrylic copolymer which has, in polymerized form, epoxy functionalized groups and cure compatibility groups; and
wherein the coating composition has a molar ratio of amine NH functionality from hydrolyzed imine functionality on the silicone imine resin, to epoxy functionality, in the range of from 0.5 to 1.3.

2. The coating composition of claim 1 having a molar ratio of amine NH functionality from hydrolyzed imine functionality on the silicone imine resin, to epoxy functionality in the range of from 0.8 to 1.

3. The coating composition of claim 1 wherein the amino-functional silicone resin has less than 30 mole percent of repeat units bearing OR′ groups bound to Si; wherein R′ is hydrogen or a hydrocarbon group.

4. The coating composition of claim 1 wherein the amino-functional silicone resin has at least 10 mole percent of the total amount of Si units of the amino-functional silicone resin comprise (1) RSiO 3/2 groups, (2) SiO 4/2 groups or mixtures thereof.

5. The coating composition of claim 1 wherein the epoxy functionalized groups of the acrylic copolymer are derived from one or more monomers selected from the group of glycidyl methacrylate (GMA), glycidyl acrylate, and mixtures thereof; and wherein the acrylic copolymer has an epoxy equivalent weight (EEW) in the range of 200-600.

6. The coating composition of claim 4 wherein the acrylic copolymer comprises in polymerized form, 30-60% glycidyl (meth)acrylate monomer units by weight based on the weight of the total monomer units of the acrylic copolymer.

7. The coating composition of claim 1 wherein the acrylic copolymer comprises in polymerized form, from 2% to 20% cure compatibility group monomer units by weight based on the weight of the total monomer units of the acrylic copolymer.

8. The coating composition of claim 1 wherein the cure compatibility groups of the acrylic copolymer comprise monomer groups, in polymerized form, that contain one or more of alcohol (OH) functionality, a phenolic group, a tertiary amine or an acid group that is either pendant to the backbone or attached as an end group.

9. The coating composition of claim 1 wherein the cure compatibility group is derived from hydroxyethyl methacrylate (HEMA).

10. A coated article comprising one or more layers of a cured coating composition of claim 1 .

Assignees

• Dow Global Technologies Llc
• Dow Silicones Corp
• Dow Siliicones Corp

Inventors

• Piwowar Alan M
• Drumright Ray E
• Vogel Erin B
• Wieber Gary M
• Fryfogle Patrick J
• Li Yanxiang
• Machelski Susan M
• Popa Paul J
• Tomasik Adam C
• Witucki Gerald Lawrence

Classifications

• C09D183/08 Primary

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen · CPC title

• C08F220/14

  Methyl esters {, e.g. methyl (meth)acrylate} · CPC title

• C08F220/1808

  C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate · CPC title

• C08F220/20

  of polyhydric alcohols or phenols {, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate} · CPC title

• C08F220/325

  containing glycidyl radical, e.g. glycidyl (meth)acrylate · CPC title