Methyl oxirane dibenzoylresorcinol UV absorbers

• US 5,959,012 A
• Filed: 08/11/1997
• Issued: 09/28/1999
• Est. Priority Date: 08/11/1997
• Status: Expired due to Term

• Current Assignee: General Electric Company
• Original Assignee: General Electric Company
• Inventors: Simonian, Amy Kathleen, Gillette, Gregory Ronald, Pickett, James Edward
• Primary Examiner(s): Hoke, Veronica P.
• Application Number:
  US08/908,026
• Time in Patent Office: 778 Days
• Field of Search: 524/114, 524/111, 524/335, 524/108, 568/333, 549/469, 549/559, 549/453
• US Class Current: 524/335
• CPC Class Codes: C07C 45/673 by change of size of the carbon skeleton
• CPC Class Codes: C07C 45/68 by increase in the number of carbon atoms
• CPC Class Codes: C07C 49/83 polycyclic
• CPC Class Codes: C07C 49/84 containing ether groups, groups, groups, or groups
• CPC Class Codes: C07D 303/32 by aldehydo- or ketonic radicals
• CPC Class Codes: C07D 307/80 Radicals substituted by oxygen atoms
• CPC Class Codes: C07D 317/26 Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom
• CPC Class Codes: C08K 5/132 Phenols containing keto groups , e.g. benzophenones
• CPC Class Codes: C08K 5/15 Heterocyclic compounds having oxygen in the ring

Abstract

An epoxylated DBR, dibenzoylresorcinol and various derivatives thereof have been prepared to show usefulness in coatings due to compatibility and solubility. Such coatings can be acrylics, epoxies, or silicone hardcoats which are thermally or photo cured thermoset, or thermoplastic coating materials in a variety of solvent types. The disclosed UV absorber also has the advantage of a higher molecular weight and lower volatility than DBR alone thus providing processing advantages.

Claims

1. A compound having the formula ##STR3## where Ar₁ and Ar₂ are independently substituted or unsubstituted monocyclic or polycyclic aryl groups, R is hydrogen, or an aliphatic group having from 1 to 8 carbon atoms, and A is ##STR4##

2. A compound according to claim 1 having the formula

3. A compound according to claim 1 having the formula

4. A compound according to claim 1 having the formula

5. A compound according to claim 1 having the formula

6. A compound according to claim 1 having the formula

7. A compound having the formula

8. A UV absorbing coating composition comprising a transparent thermoplastic or thermosetting polymeric matrix material and a UV absorbing compound selected from the group consisting of 2-(methyloxirane)-4,6-dibenzoylrescorcinol, 2-(3-hydroxy-2-methoxypropyl)-4,6-dibenzoylresorcinol, 2-(2-hydroxy-3-methoxypropyl)-4,6-dibenzoylresorcinol, 2-hydroxymethyl-5-hydroxy-6,8-dibenzoyl-2,3-dihydrobenzofuran, 2-(2,3-dihydroxypropyl)-4.6-dibenzoylresorcinol, and 2,2-dimethyl-5- (2,6-dihydroxy-3,5-dibenzoylphenyl)methyl!-1,3-dioxolane.

9. A UV absorbing coating composition according to claim 8 comprising a transparent matrix material and 2-(methyloxirane)-4,6-dibenzoyl rescorcinol.

10. A UV absorbing coating composition according to claim 8 comprising a transparent matrix material and 2-(3-hydroxy-2-methoxypropyl)-4,6-dibenzoylresorcinol.

11. A UV absorbing coating composition according to claim 8 comprising a transparent matrix material and 2-(2-hydroxy-3-methoxypropyl)-4,6-dibenzoylresorcinol.

12. A UV absorbing coating composition according to claim 8 comprising a transparent matrix material and 2-(2,3-dihydroxypropyl)-4,6-dibenzoylresorcinol.

13. A UV absorbing coating composition according to claim 8 comprising a transparent matrix material and 2,2-dimethy-5- (2,6-dihydroxy-3,5-dibenzoylphenyl)methyl!-1,3-dioxolane.

14. A UV absorbing coating composition comprising a transparent thermoplastic or thermosetting polymer matrix material and 2-hydroxymethyl-5-hydroxy-6,8-dibenzoyl-2,3-dihydrobenzofuran.

15. A coated article comprising a solid substrate and coating on the surface thereof comprising a thermoplastic or thermosetting transparent matrix material and a UV absorbing compound selected from the group consisting of 2-(methyloxirane)-4,6-dibenzoylrescorcinol, 2-(3-hydroxy-2-methoxypropyl)-4,6-dibenzoylresorcinol, 2-(2-hydroxy-3-methoxypropyl)-4,6-dibenzoylresorcinol, 2-hydroxymethyl-5-hydroxy-6,8-dibenzoyl-2,3-dihydrobenzofuran, 2-(2,3-dihydroxypropyl)-4,6-dibenzoylresorcinol, and 2,2-dimethyl-5- (2,6-dehydroxy-3,5-dibenzoylphenyl)methyl!-1,3-dioxolane.