US4629779A — Low viscosity adducts of a polycaprolactone polyo…

Claim 1

Independent Claim 70 words

An adduct of a polycaprolactone polyol and a polyepoxide comprising the reaction product of at least one polycaprolactone polyol and a polyepoxide containing two or more epoxy groups per molecule in a molar ratio of polycaprolactone polyol to polyepoxide of from about 2:1 to about 3:1, said adduct having an extreme content of less than about 0.10 percent and a viscosity of less than about 3700 centistokes at 54.5° C.

Claim 2

Dependent Claim 70 words

An adduct of a polycaprolactone polyol and a polyepoxide comprising the reaction product of at least one polycaprolactone polyol and a polyepoxide containing two or more epoxy groups per molecule in a molar ratio of polycaprolactone polyol to polyepoxide of from about 2:1 to about 3:1, said adduct having an extreme content of less than about 0.10 percent and a viscosity of less than about 3700 centistokes at 54.5° C.

Claim 3

Dependent Claim 15 words

An adduct as defined in claim 1 wherein the polycaprolactone polyol is a polycaprolactone triol.

Claim 4

Dependent Claim 15 words

An adduct as defined in claim 1 wherein the polycaprolactone polyol is a polycaprolactone diol.

Claim 5

Dependent Claim 22 words

An adduct as defined in claim 1 wherein the polycaprolactone polyol is a mixture of a polycaprolactone triol and a polycaprolactone diol.

Claim 6

Dependent Claim 22 words

An adduct as claimed in claim 1 wherein the polyepoxide containing two or more epoxy groups per molecule is a cycloaliphatic epoxide.

Claim 7

Dependent Claim 60 words

An adduct as defined in claim 5 wherein the cycloaliphatic epoxide has the formula: ##STR26## wherein R 1 through R 18 , which can be the same or different, are hydrogen or alkyl radicals generally containing one to nine carbon atoms inclusive; R is a valence bond or a divalent hydrocarbon radical generally containing one to twenty carbon atoms inclusive.

Claim 8

Dependent Claim 42 words

An adduct as defined in claim 5 wherein the cycloaliphatic epoxide has the formula: ##STR27## wherein R 1 through R 18 , which can be the same or different are hydrogen or alkyl radicals generally containing one to nine carbon atoms inclusive.

Claim 9

Dependent Claim 15 words

An adduct as defined in claim 5 wherein the cycloaliphatic epoxide has the formula: ##STR28##

Claim 10

Dependent Claim 14 words

An adduct as defined in claim 5 wherein the cycloaliphatic epoxide is 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate.

Claim 11

Dependent Claim 13 words

An adduct as defined in claim 5 wherein the cycloaliphatic epoxide is bis(3,4-epoxycyclohexylmethyl)adipate.

Claim 12

Dependent Claim 14 words

An adduct as defined in claim 5 wherein the cycloaliphatic epoxide is vinylcyclohexene diepoxide.

Claim 13

Dependent Claim 22 words

An adduct as defined in claim 1 wherein the polyepoxide containing two or more epoxy groups per molecule is a polyglycidyl epoxide.

Claim 14

Dependent Claim 18 words

An adduct as defined in claim 12 wherein the polyglycidyl epoxide is a diglycidyl ether of Bisphenol A.

Claim 15

Dependent Claim 29 words

An adduct as defined in claim 1 wherein the polyepoxide containing two or more epoxy groups per molecule is a mixture of a cycloaliphatic epoxide and a polyglycidyl epoxide.

Claim 16

Dependent Claim 29 words

An adduct as defined in claim 1 having an oxirane content of less than about 0.05 percent and a viscosity of less than about 3500 centistokes at 54.5° C.

Claim 17

Dependent Claim 29 words

An adduct as defined in claim 1 having an oxirane content of less than about 0.025 percent and a viscosity of less than about 3000 centistokes at 54.5° C.

Claim 18

Dependent Claim 29 words

An adduct as defined in claim 1 having an oxirane content of less than about 0.025 percent and a viscosity of less than about 1000 centistokes at 54.5° C.

Claim 19

Dependent Claim 19 words

An adduct as defined in claim 1 wherein the molar ratio of polycaprolactone polyol to polyepoxide is about 2.5:1.

Claim 20

Dependent Claim 66 words

An adduct of a polycaprolactone polyol and a polyepoxide comprising the reaction product of at least one polycaprolactone polyol and a polyglycidyl epoxide containing two or more epoxy groups per molecule in a molar ratio of from about 2:1 to about 3:1, said adduct having an oxirane content of less than about 1.0 percent and a viscosity of less than about 25,000 centistokes at 54.5° C.

Claim 21

Dependent Claim 66 words

An adduct of a polycaprolactone polyol and a polyepoxide comprising the reaction product of at least one polycaprolactone polyol and a polyglycidyl epoxide containing two or more epoxy groups per molecule in a molar ratio of from about 2:1 to about 3:1, said adduct having an oxirane content of less than about 1.0 percent and a viscosity of less than about 25,000 centistokes at 54.5° C.

Claim 22

Dependent Claim 68 words

An adduct of a polycaprolactone polyol and a polyepoxide comprising the reaction product of one polycaprolactone polyol and a polyepoxide containing two or more epoxy groups per molecule in a molar ratio of polycaprolactone polyol to polyepoxide of from about 2:1 to about 3:1, said adduct having an oxirane content of less than about 0.50 percent and a viscosity of less than about 20,000 centistokes at 54.5° C.

Claim 23

Dependent Claim 68 words

An adduct of a polycaprolactone polyol and a polyepoxide comprising the reaction product of one polycaprolactone polyol and a polyepoxide containing two or more epoxy groups per molecule in a molar ratio of polycaprolactone polyol to polyepoxide of from about 2:1 to about 3:1, said adduct having an oxirane content of less than about 0.50 percent and a viscosity of less than about 20,000 centistokes at 54.5° C.

Claim 24

Dependent Claim 124 words

A process for preparing a low viscosity adduct of a polycaprolactone polyol and a polyepoxide which process comprises reacting at least one polycaprolactone polyol and a polyepoxide containing two or more epoxy groups per molecule in the presence of a sulfonic acid catalyst or derivative thereof at a temperature of from about 80° C. to about 225° C., said polycaprolactone polyol, polyepoxide and sulfonic acid catalyst or derivative thereof being employed in an amount at least sufficient to effect substantially complete reaction of the epoxy groups of the polyepoxide to give an oxirane content of less than about 0.10 percent and in a sufficiently short period of time of less than about 6 hours whereby to minimize the formation of a high viscosity product.

Claim 25

Dependent Claim 124 words

A process for preparing a low viscosity adduct of a polycaprolactone polyol and a polyepoxide which process comprises reacting at least one polycaprolactone polyol and a polyepoxide containing two or more epoxy groups per molecule in the presence of a sulfonic acid catalyst or derivative thereof at a temperature of from about 80° C. to about 225° C., said polycaprolactone polyol, polyepoxide and sulfonic acid catalyst or derivative thereof being employed in an amount at least sufficient to effect substantially complete reaction of the epoxy groups of the polyepoxide to give an oxirane content of less than about 0.10 percent and in a sufficiently short period of time of less than about 6 hours whereby to minimize the formation of a high viscosity product.

Claim 26

Dependent Claim 15 words

A process as defined in claim 21 wherein the polycaprolactone polyol is a polycaprolactone triol.

Claim 27

Dependent Claim 15 words

A process as defined in claim 21 wherein the polycaprolactone polyol is a polycaprolactone diol.

Claim 28

Dependent Claim 22 words

A process as defined in claim 21 wherein the polycaprolactone polyol is a mixture of a polycaprolactone triol and a polycaprolactone diol.

Claim 29

Dependent Claim 22 words

A process as defined in claim 21 wherein the polyepoxide containing two or more epoxy groups per molecule is a cycloaliphatic epoxide.

Claim 30

Dependent Claim 60 words

A process as defined in claim 25 wherein the cycloaliphatic epoxide has the formula: ##STR29## wherein R 1 through R 18 , which can be the same or different, are hydrogen or alkyl radicals generally containing one to nine carbon atoms inclusive; R is a valence bond or a divalent hydrocarbon radical generally containing one to twenty carbon atoms inclusive.

Claim 31

Dependent Claim 42 words

A process as defined in claim 25 wherein the cycloaliphatic epoxide has the formula: ##STR30## wherein R 1 through R 18 , which can be the same or different are hydrogen or alkyl radicals generally containing one to nine carbon atoms inclusive.

Claim 32

Dependent Claim 36 words

A process as defined in claim 25 wherein the cycloaliphatic epoxide has the formula: ##STR31## wherein the R prime and double prime groups are the same or different and are monovalent substituents or monovalent hydrocarbon radicals.

Claim 33

Dependent Claim 14 words

A process as defined in claim 25 wherein the cycloaliphatic epoxide is 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate.

Claim 34

Dependent Claim 13 words

A process as defined in claim 25 wherein the cycloaliphatic epoxide is bis(3,4-epoxycyclohexylmethyl)adipate.

Claim 35

Dependent Claim 14 words

A process as defined in claim 25 wherein the cycloaliphatic epoxide is vinylcyclohexene diepoxide.

Claim 36

Dependent Claim 22 words

A process as defined in claim 21 wherein the polyepoxide containing two or more epoxy groups per molecule is a polyglycidyl epoxide.

Claim 37

Dependent Claim 18 words

A process as defined in claim 32 wherein the polyglycidyl epoxide is a diglycidyl ether of Bisphenol A.

Claim 38

Dependent Claim 29 words

A process as defined in claim 21 wherein the polyepoxide containing two or more epoxy groups per molecule is a mixture of a cycloaliphatic epoxide and a polyglycidyl epoxide.

Claim 39

Dependent Claim 39 words

A process as defined in claim 21 where the polycaprolactone polyol and polyepoxide containing two or more epoxy groups per molecule are present in a molar ratio of polycaprolactone polyol to polyepoxide of from about 2:1 to about 3:1.

Claim 40

Dependent Claim 81 words

A process as defined in claim 21 wherein the sulfonic acid catalyst or derivative thereof has the formula: (R.sub.f SO.sub.3).sub.n M wherein R f is fluoroalkyl having from 1 to 18 carbon atoms, M is ammonium cation, quaternary ammonium cation, cation of amine or cation or metal selected from Groups I to V and VIII, subgroups VI-B and VII-B, and lanthanide and actinide series of metals of the Periodic Table, and n is an integer equal to the valence of M.

Claim 41

Dependent Claim 18 words

A process as defined in claim 36 wherein the sulfonic acid catalyst or derivative thereof is trifluoromethanesulfonic acid.

Claim 42

Dependent Claim 18 words

A process as defined in claim 36 where the sulfonic acid catalyst or derivative thereof is diethylammonium triflate.

Claim 43

Dependent Claim 38 words

A process as defined in claim 21 wherein the sulfonic acid catalyst or derivative thereof is present in an amount of from about 0.0001 weight percent to about 1.0 weight percent based on the total charge of ingredients.

Claim 44

Dependent Claim 127 words

A process for preparing a low viscosity adduct of a polycaprolactone polyol and a polyepoxide which process comprises reacting at least one polycaprolactone polyol and a polyglycidyl epoxide containing two or more epoxy groups per molecule in the presence of a sulfonic acid catalyst or derivative thereof at a temperature of from about 80° C. to about 225° C., said polycaprolactone polyol, polyglycidyl epoxide and sulfonic acid catalyst or derivative thereof being employed in an amount at least sufficient to effect substantially complete reaction of the epoxy groups of the polyglycidyl epoxide to give an oxirane content of less than about 1.0 percent and in a sufficiently short period of time of less than about 6 hours whereby to minimize the formation of a high viscosity product.

Claim 45

Dependent Claim 127 words

A process for preparing a low viscosity adduct of a polycaprolactone polyol and a polyepoxide which process comprises reacting at least one polycaprolactone polyol and a polyglycidyl epoxide containing two or more epoxy groups per molecule in the presence of a sulfonic acid catalyst or derivative thereof at a temperature of from about 80° C. to about 225° C., said polycaprolactone polyol, polyglycidyl epoxide and sulfonic acid catalyst or derivative thereof being employed in an amount at least sufficient to effect substantially complete reaction of the epoxy groups of the polyglycidyl epoxide to give an oxirane content of less than about 1.0 percent and in a sufficiently short period of time of less than about 6 hours whereby to minimize the formation of a high viscosity product.

Claim 46

Dependent Claim 121 words

A process for preparing a low viscosity adduct of a polycaprolactone polyol and a polyepoxide which process comprises reacting one polycaprolactone polyol and a polyepoxide containing two or more epoxy groups per molecule in the presence of a sulfonic acid catalyst or derivative thereof at a temperature of from about 80° C. to about 225° C., said polycaprolactone polyol, polyepoxide and sulfonic acid catalyst or derivative thereof being employed in an amount at least sufficient to effect substantially complete reaction of the epoxy groups of the polyepoxide to give an oxirane content of less than about 0.50 percent and in a sufficiently short period of time of less than about 6 hours whereby to minimize the formation of high viscosity product.

Claim 47

Dependent Claim 121 words

A process for preparing a low viscosity adduct of a polycaprolactone polyol and a polyepoxide which process comprises reacting one polycaprolactone polyol and a polyepoxide containing two or more epoxy groups per molecule in the presence of a sulfonic acid catalyst or derivative thereof at a temperature of from about 80° C. to about 225° C., said polycaprolactone polyol, polyepoxide and sulfonic acid catalyst or derivative thereof being employed in an amount at least sufficient to effect substantially complete reaction of the epoxy groups of the polyepoxide to give an oxirane content of less than about 0.50 percent and in a sufficiently short period of time of less than about 6 hours whereby to minimize the formation of high viscosity product.

Claim 48

Dependent Claim 16 words

An adduct of a polycaprolactone polyol and a polyepoxide prepared by the process of claim 21.

Claim 49

Dependent Claim 16 words

An adduct of a polycaprolactone polyol and a polyepoxide prepared by the process of claim 40.

Claim 50

Dependent Claim 16 words

An adduct of a polycaprolactone polyol and a polyepoxide prepared by the process of claim 41.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1989-12-15	1990-06-16	1990-12-16	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1993-12-15	1994-06-16	1994-12-16	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	1997-12-15	1998-06-16	1998-12-16	$7700.00	Window Closed / Lapsed

Low viscosity adducts of a polycaprolactone polyol and a polyepoxide

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