Composition of epoxy, urethane polyacrylate and polyamine

• US 6,437,059 B1
• Filed: 02/11/1999
• Issued: 08/20/2002
• Est. Priority Date: 02/11/1999
• Status: Expired due to Term

• Current Assignee: Reichhold LLC 2 (DIC Corporation)
• Original Assignee: Reichhold Incorporated
• Inventors: Naderhoff, Bryan A., Tan, Ling, Danneman, Jeffrey H.
• Primary Examiner(s): SELLERS, ROBERT E
• Application Number:
  US09/248,890
• Time in Patent Office: 1,286 Days
• Field of Search: 525/528, 525/452, 525/454, 525/455, 427/386
• US Class Current: 525/528
• CPC Class Codes: C08G 18/673 containing two or more acrylate or alkylacrylate ester groups
• CPC Class Codes: C08G 59/50 Amines
• CPC Class Codes: C08L 63/00 Compositions of epoxy resins; Compositions of derivatives of epoxy resins
• CPC Class Codes: C08L 75/04 Polyurethanes
• CPC Class Codes: C09D 175/16 having terminal carbon-to-carbon unsaturated bonds

Abstract

A composition suitable for forming a paint marking on a roadway comprises a polyfunctional urethane acrylate having at least two acrylate groups, an epoxy component and a polyfunctional amine. The polyfunctional urethane acrylate reacts with the polyfunctional amine to form an adduct with secondary amine groups. The secondary amine reacts with the epoxy component to yield a chemically crosslinked material having a no track time of less than about ten minutes.

Claims

1. A polymeric composition exhibiting a fast cure rate, said composition consisting essentially of:

a polyfunctional urethane acrylate component having more than four acrylate functionalities per molecule;

an epoxy component; and

from about 20 to about 40 percent by weight of a polyfunctional amine component;

wherein said polyfunctional urethane acrylate component and said polyfunctional amine component have sufficient functionalities such that said polyfunctional urethane acrylate component reacts with said polyfunctional amine component to form a secondary amine component, and wherein said secondary amine reacts with said epoxy component such that a chemically crosslinked polymeric material is formed, and wherein said polymeric composition has a no track time of less than about 10 minutes.

2. The composition according to claim 1, wherein the polyfunctional urethane acrylate component is a reaction product of a hydroxyl functional acrylate and an aliphatic isocyanate.

3. The composition according to claim 2, wherein the hydroxy functional acrylate is selected from the group consisting of pentaerythritol triacrylate, ethoxylated pentaerythritol triacrylate, propoxylated pentaerythritol triacrylate, and mixtures thereof.

4. The composition according to claim 2, wherein the hydroxy functional acrylate is pentaerythritol triacrylate.

5. The composition according to claim 1, wherein the aliphatic polyamine contains at least two amine groups per molecule.

6. The composition according to claim 1, wherein the aliphatic polyamine is selected from the group consisting of diethylene triamine, ethylene diamine, hexamethylene diamine, triethylene tetramine, tetraethylene pentamine, aminoethylpiperazine, and mixtures thereof.

7. The composition according to claim 1, wherein the epoxy component is selected from an epoxide resin, an epoxy diluent, an epoxy flexiblizer, and mixtures thereof.

8. The composition according to claim 1, wherein the epoxy component contains more than one 1,2-epoxy groups per molecule.

9. The composition according to claim 1, wherein said composition comprises an accelerator.

10. A traffic paint composition comprising the polymeric composition defined in claim 1 and at least one pigment.

11. The composition according to claim 10, wherein the polyfunctional urethane acrylate component is a reaction product of a hydroxy functional acrylate and an aliphatic isocyanate.

12. The composition according to claim 11, wherein the hydroxy functional acrylate is selected from the group consisting of pentaerythritol triacrylate, ethoxylated pentaerythritol triacrylate, propoxylated pentaerythritol triacrylate, and mixtures thereof.

13. The composition according to claim 12, wherein the hydroxy functional acrylate is pentaerythritol triacrylate.

14. The polymeric composition according to claim 1, wherein the epoxy component is selected from the group consisting of resins based on diglycidyl ether of bisphenol-A, resins based on diglycidyl ether of bisphenol-F, diglycidyl ether of tetrabromobisphenol A, epoxy novolacs based on phenol-formaldehyde condensates, epoxy novolacs based on phenol-cresol condensates, epoxy novolacs based on phenol-dicyclopentadiene condensates, diglycidyl ether of hydrogenated bisphenol A, digylcidyl ether of resorcinol, tetraglycidyl ether of sorbitol, tetra glycidyl ether of methylene dianiline, and mixtures thereof.

15. The polymeric composition according to claim 1, wherein the epoxy diluent is selected from the group consisting of glycidyl ethers of 2-ethylhexanol, glycidyl ethers of C₈-C₁₀ alcohol, glycidyl ethers of C₁₂-C₁₄ alcohol, glycidyl ethers of cresol, glycidyl ethers of p-tertiary butyl phenol, glycidyl ethers of nonyl phenol, glycidyl ethers of phenol, glycidyl ethers of neopentyl glycol, glycidyl ethers of 1,4-butanediol, glycidyl ethers of cyclohexane dimethanol, glycidyl ethers of propylene glycol, glycidyl ethers of dibromo neopentyl glycol, glycidyl ethers of timethylol propane, glycidyl ethers of trimethylol ethane, glycidyl ethers of n-butanol, and mixtures thereof.

16. The polymeric composition according to claim 1, wherein the epoxy flexibilizer is selected from the group consisting of rubber-modified bisphenol A epoxies, epoxidized castor oil based epoxies, epoxies which are modified with dimerized fatty acids, and mixtures thereof.

17. A polymeric composition exhibiting a fast cure rate, said composition consisting essentially of:

a hexafunctional urethane acrylate component formed from pentaerythritol triacrylate;

an epoxy component; and

from about 20 to about 40 percent by weight of a polyfunctional amine component;

wherein said hexafunctional urethane acrylate component and said polyfunctional amine component have sufficient functionalities such that said hexafunctional urethane acrylate component reacts with said polyfunctional amine component to form a secondary amine component, and wherein said secondary amine reacts with said epoxy component such that a chemically crosslinked polymeric material is formed, and wherein said polymeric composition has a no track time of less than about 10 minutes.