Polycaprolactone-epoxide adducts and coating compositions thereof

Claim 2

A water insoluble polycaprolactone-epoxide adduct comprising the reaction product mixture of a polycaprolactone polyol, a diepoxide and an anhydride of a polycarboxylic acid, said water insoluble polycaprolactone-epoxide adduct reaction product mixture produced by a process selected from the group consisting of Route 1 or Route 2, wherein Route 1 comprises the steps of (i) reacting a polycaprolactone polyol having at least two hydroxyl groups in the molecule, a hydroxyl number of from about 15 to about 600 and an average molecular weight of from 290 to about 6000 with a diepoxide to produce a water insoluble polycaprolactone-epoxide intermediate, and then (ii) reacting the intermediate of (i) with an intramolecular anhydride of a polycarboxylic acid to produce said water insoluble polycaprolactone-epoxide adduct reaction product mixture, and wherein Route 2 comprises the steps of (i) reacting a polycaprolactone polyol having at least two hydroxyl groups in the molecule, a hydroxyl number of from about 15 to about 600 and an average molecular weight of from 290 to about 6000 with an intra-molecular anhydride of a polycarboxylic acid to produce a water insoluble polycaprolactone adduct intermediate, and then (ii) reacting the intermediate of (i) with a diepoxide to produce said water insoluble polycaprolactone-epoxide adduct reaction product mixture and wherein there is used from 0.1 to about 0.5 anhydride equivalent for each unreacted hydroxyl equivalent or group initially present in the polycaprolactone polyol or formed in the polycaprolactone-epoxide adduct.

Claim 3

A water insoluble polycaprolactone-epoxide adduct as claimed in claim 1, wherein said polycaprolactone polyol has from 2 to 6 hydroxyl groups.

Claim 4

A water insoluble polycaprolactone-epoxide adduct as claimed in claim 1, wherein said polycaprolactone polyol has from 2 to 4 hydroxyl groups.

Claim 5

A water insoluble polycaprolactone-epoxide adduct as claimed in claim 1, wherein said polycaprolactone polyol has an average molecular weight of from 290 to about 3,000.

Claim 6

A water insoluble polycaprolactone-epoxide adduct as claimed in claim 1, wherein said polycaprolactone polyol is a diol having an average molecular weight of from 290 to about 500.

Claim 7

A water insoluble polycaprolactone-epoxide adduct as claimed in claim 1, wherein said polycaprolactone polyol is a triol having an average molecular weight of from about 300 to about 1,000.

Claim 8

A water insoluble polycaprolactone-epoxide adduct as claimed in claim 1, wherein said polycaprolactone polyol is a mixture of polycaprolactone polyols.

Claim 9

A water insoluble polycaprolactone-epoxide adduct as claimed in claim 1, wherein said anhydride is phthalic anhydride.

Claim 10

A water insoluble polycaprolactone-epoxide adduct as claimed in claim 1, wherein said anhydride is maleic anhydride.

Claim 11

A water insoluble polycaprolactone-epoxide adduct as claimed in claim 1, wherein said diepoxide is 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate.

Claim 12

A water insoluble polycaprolactone-epoxide adduct as claimed in claim 1, wherein from 0.2 to 1 mole of diepoxide is charged per mole of polycaprolactone polyol initially charged and reacted.

Claim 13

A water insoluble polycaprolactone-epoxide adduct as claimed in claim 1, wherein from 0.3 to 0.6 mole of diepoxide is charged per mole of polycaprolactone polyol initially charged and reacted.

Claim 14

A water insoluble polycaprolactone-epoxide adduct as claimed in claim 1, wherein said polycaprolactone polyol is a polycaprolactone triol having an average molecular weight of 300 and an average hydroxyl number of 560, said diepoxide is 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate and said anhydride is phthalic anhydride.

Claim 15

A water insoluble polycaprolactone-epoxide adduct as claimed in claim 1, wherein said polycaprolactone polyol is a polycaprolactone triol having an average molecular weight of 300 and an average hydroxyl number of 560, said diepoxide is 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate and said anhydride is maleic anhydride.

Claim 16

A water insoluble polycaprolactone-epoxide adduct as claimed in claim 1, wherein said polycaprolactone polyol is a polycaprolactone triol having an average molecular weight of 540 and an average hydroxyl number of 310, said diepoxide is 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate and said anhydride is phthalic anhydride.

Claim 17

A water insoluble polycaprolactone-epoxide adduct as claimed in claim 1, wherein said polycaprolactone polyol is a mixture of a polycaprolactone triol having an average molecular weight of 540 and an average hydroxyl number of 310 and a polycaprolactone triol having an average molecular weight of 300 and an average hydroxyl number of 560, said diepoxide is 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate and said anhydride is succinic anhydride.

Claim 18

A water soluble polycaprolactone-epoxide adduct comprising the adduct reaction product mixture of a polycaprolactone polyol, a diepoxide and an anhydride of a polycarboxylic acid, said water soluble polycaprolactone-epoxide adduct reaction product mixture produced by a process selected from the group consisting of Route 1 or Route 2, wherein Route 1 comprises the steps of (i) reacting a polycaprolactone polyol having at least two hydroxyl groups in the molecule, a hydroxyl number of from about 15 to about 600 and an average molecular weight of from 290 to about 6000 with a diepoxide to produce a water insoluble polycaprolactone-epoxide intermediate, then (ii) reacting the intermediate of (i) with an intramolecular anhydride of polycarboxylic acid to produce a second water insoluble polycaprolactone-epoxide adduct intermediate and then (iii) reacting the second intermediate of (ii) with an inorganic or organic base in an amount sufficient to neutralize the free carboxyl groups of the intermediate of (ii) to produce said water soluble polycaprolactone-epoxide adduct reaction product mixture, and wherein Route 2 comprises the steps of (i) reacting a polycaprolactone polyol having at least two hydroxyl groups in the molecule, a hydroxyl number of from about 15 to about 600 and an average molecular weight of from 290 to about 6000 with an intra-molecular anhydride of a polycarboxylic acid to produce a water insoluble polycaprolactone adduct intermediate, then (ii) reacting the intermediate of (i) with a diepoxide to produce a second water insoluble polycaprolactone-epoxide adduct intermediate, and then (iii) reacting the second intermediate of (ii) with an inorganic or organic base in an amount sufficient to neutralize the free carboxyl groups of the intermediate of (ii) to produce said water soluble polycaprolactone-epoxide adduct reaction product mixture and wherein there is used from 0.1 to about 0.5 anhydride equivalent for each unreacted hydroxyl equivalent or group initially present in the polycaprolactone polyol or formed in the polycaprolactone-epoxide adduct.

Claim 19

A water soluble polycaprolactone-epoxide adduct comprising the adduct reaction product mixture of a polycaprolactone polyol, a diepoxide and an anhydride of a polycarboxylic acid, said water soluble polycaprolactone-epoxide adduct reaction product mixture produced by a process selected from the group consisting of Route 1 or Route 2, wherein Route 1 comprises the steps of (i) reacting a polycaprolactone polyol having at least two hydroxyl groups in the molecule, a hydroxyl number of from about 15 to about 600 and an average molecular weight of from 290 to about 6000 with a diepoxide to produce a water insoluble polycaprolactone-epoxide intermediate, then (ii) reacting the intermediate of (i) with an intramolecular anhydride of polycarboxylic acid to produce a second water insoluble polycaprolactone-epoxide adduct intermediate and then (iii) reacting the second intermediate of (ii) with an inorganic or organic base in an amount sufficient to neutralize the free carboxyl groups of the intermediate of (ii) to produce said water soluble polycaprolactone-epoxide adduct reaction product mixture, and wherein Route 2 comprises the steps of (i) reacting a polycaprolactone polyol having at least two hydroxyl groups in the molecule, a hydroxyl number of from about 15 to about 600 and an average molecular weight of from 290 to about 6000 with an intra-molecular anhydride of a polycarboxylic acid to produce a water insoluble polycaprolactone adduct intermediate, then (ii) reacting the intermediate of (i) with a diepoxide to produce a second water insoluble polycaprolactone-epoxide adduct intermediate, and then (iii) reacting the second intermediate of (ii) with an inorganic or organic base in an amount sufficient to neutralize the free carboxyl groups of the intermediate of (ii) to produce said water soluble polycaprolactone-epoxide adduct reaction product mixture and wherein there is used from 0.1 to about 0.5 anhydride equivalent for each unreacted hydroxyl equivalent or group initially present in the polycaprolactone polyol or formed in the polycaprolactone-epoxide adduct.

Claim 20

A water soluble polycaprolactone-epoxide adduct as claimed in claim 17, wherein said polycaprolactone polyol has from 2 to 6 hydroxyl groups, and said base is an organic base.

Claim 21

A water soluble polycaprolactone-epoxide adduct as claimed in claim 17, wherein said polycaprolactone polyol has from 6 to 4 hydroxyl groups, and said base is an organic base.

Claim 22

A water soluble polycaprolactone-epoxide adduct as claimed in claim 17, wherein said polycaprolactone polyol has an average molecular weight of from 290 to about 3,000, and said base is an organic base.

Claim 23

A water soluble polycaprolactone-epoxide adduct as claimed in claim 17, wherein said polycaprolactone polyol is a diol having an average molecular weight of from 290 to about 500, and said base is an organic base.

Claim 24

A water soluble polycaprolactone-epoxide adduct as claimed in claim 17, wherein said polycaprolactone polyol is a triol having an average molecular weight of from about 300 to about 1,000, and said base is an organic base.

Claim 25

A water soluble polycaprolactone-epoxide adduct as claimed in claim 17, wherein said polycaprolactone polyol is a mixture of polycaprolactone polyols, and said base is an organic base.

Claim 26

A water soluble polycaprolactone-epoxide as claimed in claim 17, wherein said anhydride is phthalic anhydride, and said base is an organic base.

Claim 27

A water soluble polycaprolactone-epoxide as claimed in claim 17, wherein said anhydride is maleic anhydride, and said base is an organic base.

Claim 28

A water soluble polycaprolactone-epoxide as claimed in claim 17, wherein said diepoxide is 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate, and said base is an organic base.

Claim 29

A water soluble polycaprolactone-epoxide as claimed in claim 17, wherein in said adduct reaction product from 0.2 to 1 mole of diepoxide is reacted per mole of polycaprolactone polyol initially charged, and said base is an organic base.

Claim 30

A water soluble polycaprolactone-epoxide as claimed in claim 17, wherein in said adduct reaction product from 0.3 to 0.6 mole of diepoxide is reacted per mole of polycaprolactone polyol initially charged, and said base is an organic base.

Claim 31

A water soluble polycaprolactone-epoxide as claimed in claim 17, wherein in said adduct reaction product from 0.2 to 1 mole of diepoxide is reacted per mole of polycaprolactone initially charged and from 0.1 to 0.5 carboxylic anhydride equivalent per unreacted hydroxyl equivalent in said polycaprolactone polyol are reacted and said base is an organic base.

Claim 32

A water soluble polycaprolactone-epoxide as claimed in claim 17, wherein in said adduct reaction product from 0.3 to 0.6 mole of diepoxide is reacted per mole of polycaprolactone initially charged and from 0.1 to 0.5 carboxylic anhydride equivalent per unreacted hydroxyl equivalent in said polycaprolactone polyol are reacted and said base is an organic base.

Claim 33

A water soluble polycaprolactone-epoxide as claimed in claim 17, wherein in said adduct reaction product said polycaprolactone polyol is a polycaprolactone triol having an average molecular weight of 300 and an average hydroxyl number of 560, said diepoxide is 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate and said anhydride is phthalic anhydride, and said base is N,N-dimethyl ethanolamine.

Claim 34

A water soluble polycaprolactone-epoxide as claimed in claim 17, wherein in said adduct reaction product said polycaprolactone polyol is a polycaprolactone triol having an average molecular weight of 300 and an average hydroxyl number of 560, and diepoxide is 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate and said anhydride is maleic anhydride, and said base is N,N-dimethyl ethanolamine.

Claim 35

A water soluble polycaprolactone-epoxide as claimed in claim 17, wherein in said adduct reaction product said polycaprolactone polyol is a polycaprolactone triol having an average molecular weight of 540 and an average hydroxyl number of 310, and said base is N,N-dimethyl ethanolamine.

Claim 36

A water soluble polycaprolactone-epoxide as claimed in claim 17, wherein in said adduct reaction product said polycaprolactone polyol is a mixture of a polycaprolactone triol having an average molecular weight of 540 and an average hydroxyl number of 310 and a polycaprolactone triol having an average molecular weight of 300 and an average hydroxyl number of 560, said diepoxide is 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate and said anhydride is succinic anhydride, and said base is N,N-dimethyl ethanolamine.

Claim 37

A coating composition comprising a water soluble polycaprolactone-epoxide adduct as claimed in claim 17 and additionally containing from 25 to 200 weight percent of an amine crosslinking agent based on the weight of said water soluble adduct.

Claim 38

A coating composition comprising a water soluble polycaprolactone-epoxide adduct as claimed in claim 18 and additionally containing from 25 to 200 weight percent of an amine crosslinking agent based on the weight of said water soluble adduct.

Claim 39

A coating composition comprising a water soluble polycaprolactone-epoxide adduct as claimed in claim 19 and additionally containing from 25 to 200 weight percent of an amine crosslinking agent based on the weight of said water soluble adduct.

Claim 40

A coating composition comprising a water soluble polycaprolactone-epoxide adduct as claimed in claim 20 and additionally containing from 25 to 200 weight percent of an amine crosslinking agent based on the weight of said water soluble adduct.

Claim 41

A coating composition comprising a water soluble polycaprolactone-epoxide adduct as claimed in claim 21 and additionally containing from 25 to 200 weight percent of an amine crosslinking agent based on the weight of said water soluble adduct.

Claim 42

A coating composition comprising a water soluble polycaprolactone-epoxide adduct as claimed in claim 22 and additionally containing from 25 to 200 weight percent of an amine crosslinking agent based on the weight of said water soluble adduct.

Claim 43

A coating composition comprising a water soluble polycaprolactone-epoxide adduct as claimed in claim 23 and additionally containing from 25 to 200 weight percent of an amine crosslinking agent based on the weight of said water soluble adduct.

Claim 44

A coating composition comprising a water soluble polycaprolactone-epoxide adduct as claimed in claim 24 and additionally containing from 25 to 200 weight percent of an amine crosslinking agent based on the weight of said water soluble adduct.

Claim 45

A coating composition comprising a water soluble polycaprolactone-epoxide adduct as claimed in claim 25 and additionally containing from 25 to 200 weight percent of an amine crosslinking agent based on the weight of said water soluble adduct.

Claim 46

A coating composition comprising a water soluble polycaprolactone-epoxide adduct as claimed in claim 26 and additionally containing from 25 to 200 weight percent of an amine crosslinking agent based on the weight of said water soluble adduct.

Claim 47

A coating composition comprising a water soluble polycaprolactone-epoxide adduct as claimed in claim 27 and additionally containing from 25 to 200 weight percent of an amine crosslinking agent based on the weight of said water soluble adduct.

Claim 48

A coating composition comprising a water soluble polycaprolactone-epoxide adduct as claimed in claim 28 and additionally containing from 25 to 200 weight percent of an amine crosslinking agent based on the weight of said water soluble adduct.

Claim 49

A coating composition comprising a water soluble polycaprolactone-epoxide adduct as claimed in claim 29 and additionally containing from 25 to 200 weight percent of an amine crosslinking agent based on the weight of said water soluble adduct.

Claim 50

A coating composition comprising a water soluble polycaprolactone-epoxide adduct as claimed in claim 30 and additionally containing from 25 to 200 weight percent of an amine crosslinking agent based on the weight of said water soluble adduct.

Claim 51

A coating composition comprising a water soluble polycaprolactone-epoxide adduct as claimed in claim 31 and additionally containing from 25 to 200 weight percent of an amine crosslinking agent based on the weight of said water soluble adduct.

Claim 52

A coating composition comprising a water soluble polycaprolactone-epoxide adduct as claimed in claim 32 and additionally containing from 25 to 200 weight percent of an amine crosslinking agent based on the weight of said water soluble adduct.

Claim 53

A coating composition comprising a water soluble polycaprolactone-epoxide adduct as claimed in claim 33 and additionally containing from 25 to 200 weight percent of an amine crosslinking agent based on the weight of said water soluble adduct.

Claim 54

A coating composition comprising a water soluble polycaprolactone-epoxide adduct as claimed in claim 34 and additionally containing from 25 to 200 weight percent of an amine crosslinking agent based on the weight of said water soluble adduct.

Claim 55

A process for producing a water insoluble polycaprolactone-epoxide adduct reaction product mixture comprising the steps of (i) reacting a polycaprolactone polyol having at least two hydroxyl groups in the molecule, a hydroxyl number of from about 15 to about 600 and an average molecular weight of from 290 to about 6000 with an intramolecular anhydride of a polycarboxylic acid to produce a water insoluble polycaprolactone adduct intermediate, and (ii) reacting the intermediate of (i) with a diepoxide to produce said water insoluble polycaprolactone-epoxide adduct reaction product mixture.

Claim 56

A process for producing a water insoluble polycaprolactone-epoxide adduct reaction product mixture comprising the steps of (i) reacting a polycaprolactone polyol having at least two hydroxyl groups in the molecule, a hydroxyl number of from about 15 to about 600 and an average molecular weight of from 290 to about 6000 with an intramolecular anhydride of a polycarboxylic acid to produce a water insoluble polycaprolactone adduct intermediate, and (ii) reacting the intermediate of (i) with a diepoxide to produce said water insoluble polycaprolactone-epoxide adduct reaction product mixture.

Claim 57

A process as claimed in claim 53, wherein said water insoluble polycaprolactone-epoxide adduct reaction product mixture is reacted with an inorganic or organic base in an amount sufficient to neutralize the free carboxyl groups of said adduct reaction product mixture to produce a water soluble polycaprolactone-epoxide adduct reaction product mixture.

Claim 58

A process for producing a water insoluble polycaprolactone-epoxide adduct reaction product mixture comprising the steps of (i) reacting a polycaprolactone polyol having at least two hydroxyl groups in the molecule, a hydroxyl number of from about 15 to about 600 and an average molecular weight of from 290 to about 600 with a diepoxide to produce a water insoluble polycaprolactone-epoxide intermediate, and (ii) reacting the intermediate of (i) with an intramolecular anhydride of of polycarboxylic acid to produce a water insoluble polycaprolactone-epoxide adduct reaction product mixture.

Claim 59

A process for producing a water insoluble polycaprolactone-epoxide adduct reaction product mixture comprising the steps of (i) reacting a polycaprolactone polyol having at least two hydroxyl groups in the molecule, a hydroxyl number of from about 15 to about 600 and an average molecular weight of from 290 to about 600 with a diepoxide to produce a water insoluble polycaprolactone-epoxide intermediate, and (ii) reacting the intermediate of (i) with an intramolecular anhydride of of polycarboxylic acid to produce a water insoluble polycaprolactone-epoxide adduct reaction product mixture.

Claim 60

A process as claimed in claim 55, wherein said water insoluble polycaprolactone-epoxide adduct reaction product mixture is reacted with an inorganic or organic base in an amount sufficient to neutralize the free carboxyl groups of said adduct reaction product mixture to produce a water soluble polycaprolactone-epoxide reaction product mixture.