Granted Patent B2

US 12,378,435 · App. 17/775,918 · Granted Aug 5, 2025

Inventors: Steven Swier (Midland, MI); Gary M. Wieber (Midland, MI); Erin B. Vogel (Midland, MI); John B. Horstman (Midland, MI); Susan M. Machelski (Midland, MI)

Assignees: Dow Global Technologies LLC; Dow Silicones Corporation

C09D183/08C09D133/08

Abstract

Claims (39)

1. A curable coating composition comprising:

(1) an amino-functional silicone resin comprising in polymerized form, structural units of:

(i) (R 3 SiO 1/2 ) a ;

(ii) (R 2 Si(OR′) x O (2-x)/2 ) b ;

(iii) (RSi(OR′) y ,O (3-y)/2 ) c ; and

(iv) (Si(OR′) z O (4-z)/2 ) d

wherein each R′ is hydrogen, an alkyl group or a functionalized alkyl group, provided that at least 5 mole percent of all R′ groups are amine containing groups of the formula: —R a —NHR b ;

wherein R a is an alkyl group or an aryl-containing group derived from an amino alcohol and R b is hydrogen, an alkyl group, or an aryl group;

wherein a+b+c+d=1.00 (100 mole percent); x is either 0 or 1; y is either 0, 1 or 2; and z is either 0, 1, 2, or 3;

wherein each R is independently hydrogen, an alkyl group, or an aryl group; and

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 to epoxy functionality in the range of from 0.5 to 1.3;

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.

2. The coating composition of claim 1 having a molar ratio of amine NH functionality to epoxy functionality in the range of from 0.8 to 1.

3. The coating composition of claim 1 wherein at least 20 mole percent of all R′ groups of the amino-functional silicone resin are amine containing groups of the formula: —R a —NHR b .

4. The coating composition of claim 1 wherein from 5 to 42 mole percent of all R′ groups of the amino-functional silicone resin are amine containing groups of the formula: —R a —NHR b .

5. The coating composition of claim 1 wherein the amino alcohol is selected from the group which (a) has steric hindrance around the COH moiety; (b) is a secondary or tertiary alcohol; or (c) mixtures thereof.

6. The coating composition of claim 1 wherein the amino alcohol is 1-amino-2-propanol or 1-amino-2-methylpropan-2-ol.

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 .

11. A curable coating composition comprising:

(1) an amino-functional silicone resin comprising in polymerized form, structural units of:

(i) (R 3 SiO 1/2 ) a ;

(ii) (R 2 Si(OR′) x O (2-x)/2 ) b ;

(iii) (RSi(OR′) y ,O (3-y)/2 ) c ; and

(iv) (Si(OR′) z O (4-z)/2 ) d

wherein each R′ is hydrogen, an alkyl group or a functionalized alkyl group, provided that at least 5 mole percent of all R′ groups are amine containing groups of the formula: —R a —NHR b ;

wherein R a is an alkyl group or an aryl-containing group derived from an amino alcohol and R b is hydrogen, an alkyl group, or an aryl group;

wherein a+b+c+d=1.00 (100 mole percent); x is either 0 or 1; y is either 0, 1 or 2; and z is either 0, 1, 2, or 3;

wherein each R is independently hydrogen, an alkyl group, or an aryl group; and

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;

wherein the coating composition has a molar ratio of amine NH functionality to epoxy functionality in the range of from 0.5 to 1.3;

wherein from 5 to 42 mole percent of all R′ groups of the amino-functional silicone resin are amine containing groups of the formula: —R a —NHR b ; and

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.

Assignments (2)

Continuity (2)

References Cited (15)