Polyepoxide-caprolactone polyols and coatings based thereon

• US 3,896,303 A
• Filed: 11/14/1973
• Issued: 07/22/1975
• Est. Priority Date: 11/14/1973
• Status: Expired due to Term

• Current Assignee: Lowell Ray Comstock, Richard Michael Gerkin
• Original Assignee: Lowell Ray Comstock, Richard Michael Gerkin
• Inventors: Gerkin, Richard Michael, Comstock, Lowell Ray
• Primary Examiner(s): Welsh, M. J.
• Application Number:
  US05/415,791
• Time in Patent Office: 615 Days
• Field of Search: 260/78.3R,47EP
• US Class Current: 528/361
• CPC Class Codes: C08G 18/4244 containing oxygen in the form of ether groups
• CPC Class Codes: C08G 18/4277 Caprolactone and/or substituted caprolactone
• CPC Class Codes: C08L 2666/18 Polyesters or polycarbonates according to C08L67/00 - C08L69/00; Derivatives thereof
• CPC Class Codes: C09D 163/00 Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins

Abstract

Compositions useful for the formation of high performance coatings are provided as the reaction products of a caprolactone polyol having an average hydroxyl functionality of at least three and a polyepoxide. The products formed by reaction of a caprolactone triol and a cycloaliphatic diepoxide are used with particular advantage as the active hydrogen-containing component of polyurethane formulations to be applied as coatings on external surfaces of aircraft.

Claims

1. A POLYOL COMPOSITION PREPARED BY THE REACTION OF (A) A CAPROLACTONE POLYOL HAVING AN AVERAGE OF AT LEAST THREE HYDROXY GROUPS PER MOLECULE AND (B) A POLYEPOXIDE HAVING AT LEAST TWO VICINAL EPOLXY GROUPS PER MOLICULE, SAID REACTANT (A) BEING EMPLOYED IN AN AMOUNT AT LEAST SUFFICENT TO EFFECT SUBSTANTIALLY COMPLETE REACTION OF THE EPOXY GROUPS OF (B).

2. A polyol composition as defined in claim 1 in which said caprolactone polyol (a) is a caprolactone triol and said polyepoxide (b) is a cycloaliphatic diepoxide, and (a) is employed in an amount from about 1.8 to about 2.5 moles per mole of (b).

3. A polyol composition as defined in claim 2 in which said caprolactone triol (a) is used in an amount of about two moles per mole of (b).

4. A polyol composition formed by reaction at a temperature from about 100*C. to about 190*C. of:

a. a caprolactone polyol having an average of from three to six hydroxyl groups per molecule; and

b. a cycloaliphatic diepoxide having the formula,

5. A polyol composition as defined in claim 4 in which (b) has the said formula wherein a has a value of one and six of the nine R groups bonded to each cyclic nucleus are hydrogen and the remaining R groups are hydrogen or methyl.

6. A polyol composition as defined in claim 4 in which (b) has the said formula wherein a is zero and six of the nine R groups bonded to each cyclic nucleus are hydrogen and the remaining R groups are hydrogen or methyl.

7. A polyol composition prepared by the reaction at a temperature between about 100*C. and about 190*C. of:

(a) a caprolactone triol having an average molecular weight no higher than about 1300, and (b) a 3,4-epoxycyclohexylmethyl 3,4-(epoxycyclohexane)carboxylate, the mole ratio of (a) to (b) being from about 1.8;

1 to about 2.5;

1.

8. A polyol composition prepared by the reaction of:

(a) a caprolactone triol having an average hydroxyl number from about 185 to about 560 prepared by the reaction of trimethylolpropane and epsilon-caprolactone, and (b) 3,4-epoxycyclohexylmethyl (3,4-epoxycyclohexane)carboxylate, the said reaction being effected at a temperature between about 100*C. and about 190*C. in the presence of a tin carboxylate as catalyst, employing about two moles of (a) per mole of (b).

9. A polyol composition as defined in claim 8 in which (a) has an average hydroxyl number of about 560.

10. A polyol composition as defined in claim 8 in which (a) has an average hydroxyl number of about 310.

11. A polyol composition as defined in claim 8 in which the reaction of (a) and (b) is effected at a temperature from about 130*C. to about 175*C. in the presence of stannous ocotate catalyst and for a sufficient period of time to reduce the epoxy content of the reaction system to less than about 0.5 weight percent.

12. A polyol composition as defined in claim 1 in which (a) is a caprolactone triol having an average hydroxyl number from about 130 to about 560, and (b) is 3,4-epoxycyclohexylmethyl (3,4-epoxycyclohexane)carboxylate.