Radiation-curable allyl- or vinyl capped polycaprolactone compositions

• US 4,264,757 A
• Filed: 06/26/1979
• Issued: 04/28/1981
• Est. Priority Date: 06/26/1979
• Status: Expired due to Term

• Current Assignee: Union Carbide Corporation (Dow, Inc.)
• Original Assignee: Union Carbide Corporation (Dow, Inc.)
• Inventors: Park, Kisoon
• Primary Examiner(s): Hoke, V. P.
• Application Number:
  US06/052,193
• Time in Patent Office: 672 Days
• Field of Search: 528/75, 204/159.19
• US Class Current: 528/75
• CPC Class Codes: C08G 18/42 Polycondensates having carboxylic or carbonic ester groups in the main chain
• CPC Class Codes: C08G 18/4277 Caprolactone and/or substituted caprolactone
• CPC Class Codes: C08G 18/671 Unsaturated compounds having only one group containing active hydrogen takes precedence on groups C08G18/675 - C08G18/69
• CPC Class Codes: C08G 18/8108 having only one isocyanate or isothiocyanate group

Abstract

Allyl- or vinyl-capped polycaprolactone polyol derivatives are produced by the reaction of a polycaprolactone polyol, an allyl or vinyl monomer and a polyisocyanate. These novel derivatives can be used to produce novel coating compositions that are readily cured to solid protective films.

Claims

1. An allyl- or vinyl-capped polycaprolactone polyol urethane reaction product mixture comprising (I) the reaction product of the group consisting essentially of:

A. a polycaprolactone polyol having from 2 to 6 hydroxyl groups and an average molecular weight of from about 130 to about 20,000;

B. an organic polyisocyanate; and

C. a reactive vinyl or allyl compound of the formula;

space="preserve" listing-type="equation">CH.sub.2 ═

CH(CH.sub.2).sub.x R

wherein x is zero or one and R is hydroxyl, mercapto, or substituted or unsubstituted hydroxyphenol or hydroxybenzyl or hydroxycycloalkyl having 5 or 6 ring carbon atoms;

or (II) the reaction product of;

A. a polycaprolactone polyol as defined above; and

B. vinyl isocyanate or allyl isocyanate or the respective thioisocyanates thereof.

2. A vinyl-capped polycaprolactone polyol urethane reaction product mixture as claimed in claim 1, comprising the reaction product mixture of a polycaprolactone polyol produced by the reaction of diethylene glycol and epsilon-caprolactone, 4,4'"'"'-diphenylmethane diisocyanate and vinylbenzyl alcohol.

3. An allyl-capped polycaprolactone polyol urethane reaction product mixture as claimed in claim 1, comprising the reaction product of a polycaprolactone polyol produced by the reaction of diethyleneglycol and epsilon-caprolactone, tolylene diisocyanate and allyisocyanate.

4. An allyl-capped polycaprolactone polyol urethane reaction product mixture as claimed in claim 1, comprising the reaction product of a polycaprolactone polyol produced by the reaction of diethyleneglycol and epsilon-caprolactone, tolylene diisocyanate and 2-allylphenol.