Poly(ethylenically unsaturated alkoxy) heterocyclic compounds

• US 4,249,011 A
• Filed: 06/25/1979
• Issued: 02/03/1981
• Est. Priority Date: 06/25/1979
• Status: Expired due to Term

• Current Assignee: 3M Company
• Original Assignee: 3M Company
• Inventors: Wendling, Larry A.
• Primary Examiner(s): Jiles, Henry R.
• Assistant Examiner(s): Harkaway, Natalia
• Application Number:
  US06/051,876
• Time in Patent Office: 589 Days
• Field of Search: 548/307, 548/312
• US Class Current: 548/319.5
• CPC Class Codes: C07D 233/72 Two oxygen atoms, e.g. hydantoin
• CPC Class Codes: C08F 16/28 Monomers containing nitrogen
• CPC Class Codes: C08F 20/36 containing oxygen in addition to the carboxy oxygen , e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
• CPC Class Codes: C08F 216/00 Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
• CPC Class Codes: C08F 222/103 of trialcohols, e.g. trimethylolpropane tri(meth)acrylate
• CPC Class Codes: C09D 129/10 Homopolymers or copolymers of unsaturated ethers C09D135/08 takes precedence
• CPC Class Codes: C09D 4/00 Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
• CPC Class Codes: G03F 7/027 Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds G03F7/075 takes precedence

Abstract

Ethylenically unsaturated crosslinking agents and polymerizable monomers are disclosed. These agents contain a heterocyclic nucleus and are capable of forming oxygen insensitive, radiation curable systems.

Claims

1. A compound of the formula:

space="preserve" listing-type="equation">A.sup.1 --Z--A.sup.2

wherein A¹ and A² are independently groups having terminal ethylenic unsaturation said groups having the formula;

##STR19## in which R--O-- is a monovalent residue of an aliphatic terminally unsaturated primary alcohol, ROH, where R is selected from the formulae;

##STR20## wherein E is selected from the formulae ##STR21## a and c are independently integers of from 1 to 6, b is zero or an integer of from 1 to 6,

R¹ and R⁴ are independently hydrogen or methyl,

R⁵ is an aliphatic group having 1 to 15 carbon atoms which may be interrupted with up to two groups selected from the class consisting of ether oxygen groups or ##STR22## R⁵ having a valence of m+1 wherein m is an integer of 1 to 5, R² is selected from the group of hydrogen, ##STR23## wherein R⁶ is selected from alkyl and alkenyl groups having up to 5 carbon atoms,

R⁷ is an aliphatic group of up to 8 carbon atoms or aromatic group of up to 8 carbon atoms,

R³ is an alkylene group having 1 to 6 carbon atoms and up to one catenary oxygen in the group, and

Z is a heterocyclic group of the formula;

##STR24## wherein X is a divalent group required to complete a 5-membered heterocyclic ring and is selected from the group of ##STR25## wherein R⁸ and R⁹ are independently selected from hydrogen, alkyl groups of 1 to 4 carbon atoms, cycloalkyl groups of 3 to 6 carbon atoms, and phenyl groups, and

A³ is a group having terminal ethylenic unsaturation as defined above for A¹ and A².

2. The compound of claim 1 wherein R² is ##STR26## wherein R⁷ is selected from alkyl group, phenyl group, acryloyloxyalkyl group, and methacryloyloxyalkyl group.

3. The compound of claim 1 wherein R² is ##STR27## and R⁷ is selected from alkyl groups of up to eight carbon atoms and phenyl groups.

4. The compound of claim 1 wherein R² is hydrogen and R⁵ is an alkyl group having a valence of 2 to 6 with up to two catenary ether oxygen atoms.

5. The compound of claim 4 wherein X is ##STR28##

6. The compound of claim 5 wherein R⁸ and R⁹ are independently selected from hydrogen and alkyl group of 1 to 4 carbon atoms, and R⁵ is an alkyl group having a valence of 2 to 6 with up to two catenary ether oxygen atoms.

7. The compound of claim 5 wherein E is ##STR29## and m is 2 to 5.

8. The compound of claim 6 wherein E is ##STR30## and m is 2 to 5.

9. The compound of claim 8 wherein X is ##STR31##

10. The compound of claim 7 wherein R² is selected from hydrogen, ##STR32## wherein R⁶ is selected from alkenyl or alkyl radicals of 2 to 5 carbon atoms and R⁷ is selected from the group of alkyl radical of up to eight carbon atoms, phenyl radical, acryloyloxyalkyl radical and methacryloyloxyalkyl radical.

11. The compound of claim 8 wherein R² is selected from hydrogen, ##STR33## wherein R⁶ is selected from alkenyl or alkyl radicals of 2 to 5 carbon atoms and R⁷ is selected from the group of alkyl radical of up to eight carbon atoms, phenyl radical, acryloyloxyalkyl radical or methacryloyloxyalkyl radical.

12. The compound of claim 9 wherein R² is selected from hydrogen, ##STR34## wherein R⁶ is selected from alkenyl or alkyl radicals of 2 to 5 carbon atoms and R⁷ is selected from the group of alkyl radical of up to eight carbon atoms, phenyl radical, acryloyloxyalkyl radical or methacryloyloxyalkyl radical.

13. The compound of claim 1 wherein R⁵ is an alkyl group having a valence of 2 to 6 with up to two catenary ether oxygen atoms.

14. The compound of claim 13 having no catenary oxygen atoms in R⁵.

15. The compound of claim 1 wherein R² is selected from ##STR35## and R⁶ is selected from alkyl and alkenyl having 2 to 5 carbon atoms.