Norbornenyl azlactones

• US 5,837,751 A
• Filed: 11/28/1990
• Issued: 11/17/1998
• Est. Priority Date: 11/28/1990
• Status: Expired due to Fees

• Current Assignee: Loctite Corporation (Henkel AG & Co KGaA)
• Original Assignee: Loctite Corporation (Henkel AG & Co KGaA)
• Inventors: Jacobine, Anthony F., Nakos, Steven T.
• Primary Examiner(s): Berman, Susan W.
• Application Number:
  US07/619,068
• Time in Patent Office: 2,911 Days
• Field of Search: 522/99, 522/167, 522/180, 522/904, 522/146, 548/228
• US Class Current: 522/167
• CPC Class Codes: C07D 263/42 attached in position 5
• CPC Class Codes: C08G 73/024 Polyamines containing oxygen in the form of ether bonds in the main chain
• CPC Class Codes: C08G 73/028 Polyamidoamines
• CPC Class Codes: C08G 75/045 from mercapto compounds and unsaturated compounds
• CPC Class Codes: C08G 75/12 Polythioether-ethers C08G75/0245 takes precedence

Abstract

Norbornenyl functional azlactone compounds of the formula: ##STR1## wherein R¹ and R² are independently monovalent hydrocarbon groups or R¹ and R², together with the carbon atom to which they are attached comprise a cyclic hydrocarbon group, are prepared by Diels-Alder addition of cyclopentadiene to vinyl azlactones. The norbornenyl azlactones are useful for preparing norbornenyl functional resins by azlactone ring opening reactions. The resulting resins may be employed as polyene components of curable thiol-ene formulations.

Claims

1. A curable thiol-ene composition comprising a polyene, a polythiol and an initiator of thiol-ene addition reactions wherein the polyene component comprises a compound having a plurality of groups of the formula:

##STR10## wherein R¹ and R² are independently monovalent hydrocarbon groups or R¹ and R², together with the carbon atom to which they are attached comprise a cyclic hydrocarbon group R³ is --NR⁴ --, --S--, or --O-- and R⁴ is H or alkyl.

2. A curable thiol-ene composition as in claim 1 wherein R¹ and R² are selected from the group consisting of alkyl and cycloalkyl groups having 1 to 12 carbon atoms, and aryl and aralkyl groups having 6 to 12 carbon atoms or R¹ and R² taken together with the carbon atom to which they are attached form a 5 to 12 carbon atom cyclic hydrocarbon group.

3. A curable thiol-ene composition as in claim 2 wherein R¹ and R² are both methyl groups.

4. A curable thiol-ene composition as in claim 3 wherein R³ is --NH-- or --O--.

5. A curable thiol-ene composition as in claim 1 wherein the ratio of thiol to ene groups in the composition is between 0.7:

1 and 1;

1.3.

6. A curable thiol-ene composition as in claim 1 wherein the total functionality of the composition is greater than 4.