IP Library Granted Patent US 7,713,628
Granted Patent B2
US 7,713,628 · App. 11/139,508 · Granted May 11, 2010

Actinic radiation curable coating compositions

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Quick Facts
Patent No.
US 7,713,628
App. No.
11/139,508
Granted
May 11, 2010
Kind
B2
Abstract

A cured coating or molded article prepared from a composition comprising an actinic-radiation curing polymer, wherein the composition is cured with actinic radiation at a temperature of at most 150° C. to form the cured coating or molded article; wherein the cured coating or molded article has a thickness of at least about 0.5 mm and a hardness of about Shore A 90 to about Shore D 90.

Claims (23)

1. An article comprising a substrate and a clear, colorless, transparent cured coating; wherein the coating is prepared from a composition comprising an actinic-radiation curing polymer and an ultraviolet radiation stabilizer, wherein the composition is cured with actinic radiation at a temperature of at most 150° C. to form the cured coating; wherein the cured coating has a thickness of at least about 0.5 mm and a hardness of about Shore A 90 to about Shore D 90; wherein the composition further comprises at least one photoinitiator selected from the group consisting of alpha-amino ketone; bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide; bis-(2,6-dimethoxybenzoyl)-(2,4,4-trimethylpentyl)phosphine oxide; benzyldimethyl-ketal; 1-hydroxy-cyclohexylphenyl-ketone; 2-hydroxy-2-methyl-1-phenyl-1-propanone; 50:50 blend of 2-hydroxy-2-methyl-1-phenylpropan-1-one and 2,4,6-trimethylbenzoyldiphenylphosphine oxide, and 25:75 blend of bis(2,6-dimethoxybenzoyl)-2,4,4-trimethyl phenylphosphine oxide and 2-hydroxy-2-methyl-1-phenyl-propan-1-one.

2. The article of claim 1 wherein the actinic-radiation curing polymer is an acrylate polymer or a mixture of acrylate polymers.

3. The article of claim 2 wherein the acrylate polymer is selected from the group consisting of epoxy acrylates, urethane acrylates, polyester acrylates, polyether acrylates, amine-modified polyether acrylates, acrylic acrylates, and mixtures thereof.

4. The article of claim 2 wherein the acrylate polymer is a urethane acrylate.

5. The article of claim 1 wherein the actinic-radiation curing polymer is a UV cationic curing polymer.

6. The article of claim 1 wherein the UV cationic curing polymer is selected from the group consisting of cycloaliphatic epoxy resins, caprolactone polyols, diglycidal ether of bisphenol A, monoepoxides and vinyl ethers.

7. The article of claim 1 wherein the composition has a viscosity of 50 to 20,000 cps.

8. The article of claim 1 wherein the composition further comprises a two-component epoxy or polyurethane polymer.

9. The article of claim 8 wherein the composition further comprises an aliphatic isocyanate polyurethane.

10. The article of claim 1 wherein the composition further comprises a moisture-curable silylated resin composition.

11. The article of claim 1 wherein the composition further comprises at least one selected from the group consisting of flow agents, viscosity modifiers, foam control agents, plasticizing agents, moisture scavengers, adhesion promoters, temperature stabilizers, and colorizing additives.

12. The article of claim 1 comprising a substrate having a coating in the form of scripting, letters, or other shapes.

13. The article of claim 1 wherein the UV radiation stabilizer is selected from the group consisting of hydroxyphenyl-s-triazines, hydroxyphenyl-benzotriazoles, hydroxyl-benzophenones, and oxalic anilides.

14. The article of claim 1 wherein the linear shrinkage during cure is less than 2%.

15. A clear, colorless, transparent molded article prepared from a composition comprising an actinic-radiation curing polymer and a ultraviolet radiation stabilizer, wherein the composition is cured with actinic radiation while maintaining a temperature of at most 150° C. to form the cured molded article; wherein the molded article has a thickness of at least about 0.5 mm and a hardness of about Shore A 90 to about Shore D 90; wherein the composition further comprises at least one photoinitiator selected from the group consisting of alpha-amino ketone; bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide; bis-(2,6-dimethoxybenzoyl)-(2,4,4-trimethylpentyl)phosphine oxide; benzyldimethyl-ketal; 1-hydroxy-cyclohexylphenyl-ketone; 2-hydroxy-2-methyl-1-phenyl-1-propanone; 50:50 blend of 2-hydroxy-2-methyl-1-phenylpropan-1-one and 2,4,6-trimethylbenzoyldiphenylphosphine oxide, and 25:75 blend of bis(2,6-dimethoxybenzoyl)-2,4,4-trimethyl phenylphosphine oxide and 2-hydroxy-2-methyl-1-phenyl-propan-1-one.

16. The article of claim 15 wherein the UV radiation stabilizer is selected from the group consisting of hydroxyphenyl-s-triazines, hydroxyphenyl-benzotriazoles, hydroxyl-benzophenones, and oxalic anilides.

17. The article of claim 15 wherein the linear shrinkage during cure is less than 2%.

18. An article comprising a substrate and a clear, colorless, transparent cured coating; wherein the coating is prepared from a composition comprising an actinic-radiation curing polymer and a two-component epoxy or polyurethane polymer, wherein the composition is cured with actinic radiation at a temperature of at most 150° C. to form the cured coating; wherein the cured coating has a thickness of at least about 0.5 mm and a hardness of about Shore A 90 to about Shore D 90; wherein the composition further comprises a photoinitiator selected from the group consisting of bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-(2,4,4-trimethylpentyl)phosphine oxide, and 2,4,4-trimethylbenzoyl diphenylphosphine oxide.

19. The article of claim 18 wherein the composition further comprises a UV radiation stabilizer.

20. The article of claim 19 wherein the UV radiation stabilizer is selected from the group consisting of hydroxyphenyl-s-triazines, hydroxyphenyl-benzotriazoles, hydroxyl-benzophenones, and oxalic anilides.

21. The article of claim 18 wherein the linear shrinkage during cure is less than 2%.

22. A clear, colorless, transparent molded article prepared from a composition comprising an actinic-radiation curing polymer and a two-component epoxy or polyurethane polymer, wherein the composition is cured with actinic radiation at a temperature of at most 150° C. to form the cured coating; wherein the cured coating has a thickness of at least about 0.5 mm and a hardness of about Shore A 90 to about Shore D 90; wherein the composition further comprises a photoinitiator selected from the group consisting of bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-(2,4,4-trimethylpentyl)phosphine oxide, and 2,4,4-trimethylbenzoyl diphenylphosphine oxide.

23. The article of claim 22 wherein the linear shrinkage during cure is less than 2%.

Assignments (5)
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS (TERM LOAN) Recorded Feb 15, 2023
From: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
To: H.B. FULLER COMPANY; H.B. FULLER CONSTRUCTION PRODUCTS INC.; ROYAL ADHESIVES AND SEALANTS, LLC; ADCO PRODUCTS, LLC
Reel/Frame 062761/0884 →
TERM LOAN SECURITY AGREEMENT Recorded Oct 25, 2017
From: H.B. FULLER COMPANY; H.B. FULLER CONSTRUCTION PRODUCTS INC.; ROYAL ADHESIVES AND SEALANTS, LLC; ADCO PRODUCTS, LLC
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 044616/0671 →
RCF SECURITY AGREEMENT Recorded Oct 25, 2017
From: H.B. FULLER COMPANY; H.B. FULLER CONSTRUCTION PRODUCTS INC.; ROYAL ADHESIVES AND SEALANTS, LLC; ADCO PRODUCTS, LLC
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 044616/0700 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 19, 2014
From: CHEMQUE, INC.
To: ROYAL ADHESIVES & SEALANTS CANADA LTD.
Reel/Frame 033773/0192 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 8, 2006
From: BOTRIE, ALEX; DENG, YUAN; FOUCHER, DANIEL; NGUYEN, TUAN
To: CHEMQUE, INC.
Reel/Frame 017585/0870 →