US4096125A
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US
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Polycaprolactone derivatives and coating compositions thereof
Assignee: Union Carbide Corp
•
Filing: 1976-05-26
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Granted: 1978-06-20
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Expires: 1996-05-26
Abstract
Abstract Water insoluble adducts are produced comprising the reaction product of a polycaprolactone polyol and an anhydride of a polycarboxylic acid. The polycaprolactone polyol reacted with the anhydride of the polycarboxylic acid has an average of at least two hydroxyl groups in the molecule, a hydroxyl number of from about 15 to 600 and an average molecular weight of from about 290 to about 6,000. The carboxylic acid anhydride has at least one intramolecular carboxylic anhydride group. These water insoluble adducts on reaction with an inorganic or organic base produce water soluble, carboxyl modified oligomer addition reaction products which are eminently suitable for the production of aqueous coatings compositions. Exceptionally good coatings compositions are obtained when a crosslinker is present in the coating composition.
Inventors
- 👤 Oliver Wendell Smith
- 👤 Joseph Victor Koleske
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 09:12
CPC Classifications
C; C08; C08G; C08G63/00; C08G63/02; C08G63/06; C08G63/08; C09; C09D; C09D167/00; C09D167/04
Claims Analysis
Total Claims: 77
Claim 1
Independent Claim
64 words
A water insoluble adduct comprising the reaction product of a polycaprolactone polyol and an intramolecular anhydride of a polycarboxylic acid, wherein said polycaprolactone polyol has at least two hydroxyl groups in the molecule, a hydroxyl number of from 15 to 600 and an average molecular weight of from 290 to about 6,000, and wherein said anhydride has at least one intramolecular carboxylic anhydride group.
Claim 2
Dependent Claim
64 words
A water insoluble adduct comprising the reaction product of a polycaprolactone polyol and an intramolecular anhydride of a polycarboxylic acid, wherein said polycaprolactone polyol has at least two hydroxyl groups in the molecule, a hydroxyl number of from 15 to 600 and an average molecular weight of from 290 to about 6,000, and wherein said anhydride has at least one intramolecular carboxylic anhydride group.
Claim 3
Dependent Claim
20 words
A water insoluble adduct as claimed in claim 1, wherein said polycaprolactone polyol has from 2 to 6 hydroxyl groups.
Claim 4
Dependent Claim
20 words
A water insoluble adduct as claimed in claim 1, wherein said polycaprolactone polyol has from 2 to 4 hydroxyl groups.
Claim 5
Dependent Claim
23 words
A water insoluble adduct as claimed in claim 1, wherein said polycaprolactone polyol has an average molecular weight of from 290 to 3,000.
Claim 6
Dependent Claim
27 words
A water insoluble 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
Dependent Claim
28 words
A water insoluble 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
Dependent Claim
19 words
A water insoluble adduct as claimed in claim 1, wherein said polycaprolactone polyol is a mixture of polycaprolactone polyols.
Claim 9
Dependent Claim
15 words
A water insoluble adduct as claimed in claim 1, wherein said anhydride is phthalic anhydride.
Claim 10
Dependent Claim
15 words
A water insoluble adduct as claimed in claim 1, wherein said anhydride is hexahydrophthalic anhydride.
Claim 11
Dependent Claim
15 words
A water insoluble adduct as claimed in claim 1, wherein said anhydride is maleic anhydride.
Claim 12
Dependent Claim
15 words
A water insoluble adduct as claimed in claim 1, wherein said anhydride is trimellitic anhydride.
Claim 13
Dependent Claim
15 words
A water insoluble adduct as claimed in claim 1, wherein said anhydride is succinic anhydride.
Claim 14
Dependent Claim
15 words
A water insoluble adduct as claimed in claim 1, wherein said anhydride is isatoic anhydride.
Claim 15
Dependent Claim
24 words
A water insoluble adduct as claimed in claim 1, wherein from 0.1 to 1 anhydride equivalent per hydroxyl equivalent is initially charged and reacted.
Claim 16
Dependent Claim
24 words
A water insoluble adduct as claimed in claim 1, wherein from 0.1 to 0.4 anhydride equivalent per hydroxyl equivalent is initially charged and reacted.
Claim 17
Dependent Claim
38 words
A water insoluble adduct as claimed in claim 1, wherein said polycaprolactone polyol is a triol having an average molecular weight of about 540 and an average hydroxyl number of about 310 and said anhydride is phthalic anhydride.
Claim 18
Dependent Claim
38 words
A water insoluble adduct as claimed in claim 1, wherein said polycaprolactone polyol is a triol having an average molecular weight of about 540 and an average hydroxyl number of about 310 and said anhydride is hexahydrophthalic anhydride.
Claim 19
Dependent Claim
38 words
A water insoluble adduct as claimed in claim 1, wherein said polycaprolactone polyol is a triol having an average molecular weight of about 540 and an average hydroxyl number of about 310 and said anhydride is maleic anhydride.
Claim 20
Dependent Claim
38 words
A water insoluble adduct as claimed in claim 1, wherein said polycaprolactone polyol is a triol having an average molecular weight of about 300 and an average hydroxyl number of about 560 and said anhydride is maleic anhydride.
Claim 21
Dependent Claim
38 words
A water insoluble adduct as claimed in claim 1, wherein said polycaprolactone polyol is a diol having an average molecular weight of about 530 and an average hydroxyl number of about 212 and said anhydride is succinic anhydride.
Claim 22
Dependent Claim
38 words
A water insoluble adduct as claimed in claim 1, wherein said polycaprolactone polyol is a triol having an average molecular weight of about 900 and an average hydroxyl number of about 187 and said anhydride is succinic anhydride.
Claim 23
Dependent Claim
38 words
A water insoluble adduct as claimed in claim 1, wherein said polycaprolactone polyol is a triol having an average molecular weight of about 300 and an average hydroxyl number of about 560 and said anhydride is succinic anhydride.
Claim 24
Dependent Claim
60 words
A water insoluble adduct as claimed in claim 1, wherein said polycaprolactone polyol is a mixture of a triol having an average molecular weight of about 540 and an average hydroxyl number of about 310 with a triol having an average molecular weight of about 300 and an average hydroxyl number of about 560 and said anhydride is phthalic anhydride.
Claim 25
Dependent Claim
60 words
A water insoluble adduct as claimed in claim 1, wherein said polycaprolactone polyol is a mixture of a triol having an average molecular weight of about 540 and an average hydroxyl number of about 310 with a triol having an average molecular weight of about 300 and an average hydroxyl number of about 560 and said anhydride is succinic anhydride.
Claim 26
Dependent Claim
36 words
A water insoluble adduct as claimed in claim 1, wherein said polycaprolactone polyol is an octaol having an average molecular weight of 3,160 and an average hydroxyl number of 395 and said anhydride is phthalic anhydride.
Claim 27
Dependent Claim
84 words
A water soluble composition comprising the adduct reaction product of a polycaprolactone polyol and an intramolecular anhydride of a polycarboxylic acid, wherein said polycaprolactone polyol has at least two hydroxyl groups in the molecule, a hydroxyl number of from 15 to 600 and an average molecular weight of from 290 to about 6,000, and wherein said anhydride has at least one intramolecular carboxylic anhydride group and an inorganic or organic base in an amount sufficient to neutralize the free carboxyl groups of said adduct.
Claim 28
Dependent Claim
84 words
A water soluble composition comprising the adduct reaction product of a polycaprolactone polyol and an intramolecular anhydride of a polycarboxylic acid, wherein said polycaprolactone polyol has at least two hydroxyl groups in the molecule, a hydroxyl number of from 15 to 600 and an average molecular weight of from 290 to about 6,000, and wherein said anhydride has at least one intramolecular carboxylic anhydride group and an inorganic or organic base in an amount sufficient to neutralize the free carboxyl groups of said adduct.
Claim 29
Dependent Claim
29 words
A water soluble composition as claimed in claim 26 wherein said polycaprolactone in said adduct has from 2 to 6 hydroxyl groups and said base is an organic amine.
Claim 30
Dependent Claim
29 words
A water soluble composition as claimed in claim 26 wherein said polycaprolactone in said adduct has from 2 to 4 hydroxyl groups and said base is an organic amine.
Claim 31
Dependent Claim
31 words
A water soluble composition as claimed in claim 26 wherein said polycaprolactone in said adduct has a molecular weight of from 290 to 3,000 and said base is an organic amine.
Claim 32
Dependent Claim
37 words
A water soluble composition as claimed in claim 26 wherein said polycaprolactone in said adduct is a diol having an average molecular weight of from about 290 to about 500 and said base is an organic amine.
Claim 33
Dependent Claim
37 words
A water soluble composition as claimed in claim 26 wherein said polycaprolactone in said adduct is a triol having an average molecular weight of from about 300 to about 1,000 and said base is an organic amine.
Claim 34
Dependent Claim
28 words
A water soluble composition as claimed in claim 26 wherein said polycaprolactone in said adduct is a mixture of polycaprolactone polyols and said base is an organic amine.
Claim 35
Dependent Claim
25 words
A water soluble composition as claimed in claim 26, wherein said anhydride in said adduct is phthalic anhydride and said base is an organic amine.
Claim 36
Dependent Claim
25 words
A water soluble composition as claimed in claim 26, wherein said anhydride in said adduct is hexahydrophthalic anhydride and said base is an organic amine.
Claim 37
Dependent Claim
25 words
A water soluble composition as claimed in claim 26, wherein said anhydride in said adduct is maleic anhydride and said base is an organic amine.
Claim 38
Dependent Claim
25 words
A water soluble composition as claimed in claim 26, wherein said anhydride in said adduct is trimellitic anhydride and said base is an organic amine.
Claim 39
Dependent Claim
25 words
A water soluble composition as claimed in claim 26, wherein said anhydride in said adduct is succinic anhydride and said base is an organic amine.
Claim 40
Dependent Claim
25 words
A water soluble compositions as claimed in claim 26, wherein said anhydride in said adduct is isatoic anhydride and said base is an organic amine.
Claim 41
Dependent Claim
34 words
A water soluble composition as claimed in claim 26, wherein in said adduct from 0.1 to 1 anhydride equivalent per hydroxyl equivalent is initially charged and reacted, and said base is an organic base.
Claim 42
Dependent Claim
34 words
A water soluble composition as claimed in claim 26, wherein in said adduct from 0.1 to 0.4 anhydride equivalent per hydroxyl equivalent is initially charged and reacted, and said base is an organic base.
Claim 43
Dependent Claim
36 words
A water soluble composition as claimed in claim 26, wherein said polycaprolactone in said adduct is a triol having an average hydroxyl number of 310, said anhydride is phthalic anhydride, and said base is N,N-dimethyl diethanolamine.
Claim 44
Dependent Claim
43 words
A water soluble composition as claimed in claim 26, wherein said polycaprolactone in said adduct is a triol having an average molecular weight of 540 and an average hydroxyl number of 310, said anhydride is hexahydrophthalic anhydride, and said base is N,N-dimethyl diethanolamine.
Claim 45
Dependent Claim
43 words
A water soluble composition as claimed in claim 26, wherein said polycaprolactone in said adduct is a triol having an average molecular weight of 540 and an average hydroxyl number of 310, said anhydride is maleic anhydride, and said base is N,N-dimethyl diethanolamine.
Claim 46
Dependent Claim
45 words
A water soluble composition as claimed in claim 26, wherein said polycaprolactone in said adduct is a triol having an average molecular weight of about 300 and an average hydroxyl number of about 560, said anhydride is maleic anhydride, and said base is N,N-dimethyl ethanolamine.
Claim 47
Dependent Claim
45 words
A water soluble composition as claimed in claim 26, wherein said polycaprolactone in said adduct is a diol having an average molecular weight of about 530 and an average hydroxyl number of about 212, said anhydride is succinic anhydride, and said base is N,N-dimethyl ethanolamine.
Claim 48
Dependent Claim
45 words
A water soluble composition as claimed in claim 26, wherein said polycaprolactone in said adduct is a triol having an average molecular weight of about 900 and an average hydroxyl number of about 187, said anhydride is succinic anhydride, and said base is N,N-dimethyl ethanolamine.
Claim 49
Dependent Claim
45 words
A water soluble composition as claimed in claim 26, wherein said polycaprolactone in said adduct is a triol having an average molecular weight of about 300 and an average hydroxyl number of about 560, said anhydride is succinic anhydride, and said base is N,N-dimethyl ethanolamine.
Claim 50
Dependent Claim
67 words
A water soluble composition as claimed in claim 26, wherein said polycaprolactone in said adduct is a mixture of a triol having an average molecular weight of about 540 and an average hydroxyl number of about 310 with a triol having an average molecular weight of about 300 and an average hydroxyl number of about 560, said anhydride is phthalic anhydride, and said base is N,N-dimethyl ethanolamine.
Claim 51
Dependent Claim
67 words
A water soluble composition as claimed in claim 26, wherein said polycaprolactone in said adduct is a mixture of a triol having an average molecular weight of about 540 and an average hydroxyl number of about 310 with a triol having an average molecular weight of about 300 and an average hydroxyl number of about 560, said anhydride is succinic anhydride and said base is N,N-dimethyl ethanolamine.
Claim 52
Dependent Claim
45 words
A water soluble composition as claimed in claim 26, wherein said polycaprolactone in said adduct is an octaol having an average molecular weight of about 3,160 and an average hydroxyl number of about 395, said anhydride is phthalic anhydride, and said base is N,N-dimethyl diethanolamine.
Claim 53
Dependent Claim
35 words
A coating composition comprising a water soluble composition as claimed in claim 26 and additionally containing from 25 to 200 weight percent of a crosslinking agent based on the weight of water soluble adduct present.
Claim 54
Dependent Claim
35 words
A coating composition comprising a water soluble composition as claimed in claim 27 and additionally containing from 25 to 200 weight percent of a crosslinking agent based on the weight of water soluble adduct present.
Claim 55
Dependent Claim
35 words
A coating composition comprising a water soluble composition as claimed in claim 28 and additionally containing from 25 to 200 weight percent of a crosslinking agent based on the weight of water soluble adduct present.
Claim 56
Dependent Claim
35 words
A coating composition comprising a water soluble composition as claimed in claim 29 and additionally containing from 25 to 200 weight percent of a crosslinking agent based on the weight of water soluble adduct present.
Claim 57
Dependent Claim
35 words
A coating composition comprising a water soluble composition as claimed in claim 30 and additionally containing from 25 to 200 weight percent of a crosslinking agent based on the weight of water soluble adduct present.
Claim 58
Dependent Claim
35 words
A coating composition comprising a water soluble composition as claimed in claim 31 and additionally containing from 25 to 200 weight percent of a crosslinking agent based on the weight of water soluble adduct present.
Claim 59
Dependent Claim
35 words
A coating composition comprising a water soluble composition as claimed in claim 32 and additionally containing from 25 to 200 weight percent of a crosslinking agent based on the weight of water soluble adduct present.
Claim 60
Dependent Claim
35 words
A coating composition comprising a water soluble composition as claimed in claim 33 and additionally containing from 25 to 200 weight percent of a crosslinking agent based on the weight of water soluble adduct present.
Claim 61
Dependent Claim
35 words
A coating composition comprising a water soluble composition as claimed in claim 34 and additionally containing from 25 to 200 weight percent of a crosslinking agent based on the weight of water soluble adduct present.
Claim 62
Dependent Claim
35 words
A coating composition comprising a water soluble composition as claimed in claim 35 and additionally containing from 25 to 200 weight percent of a crosslinking agent based on the weight of water soluble adduct present.
Claim 63
Dependent Claim
35 words
A coating composition comprising a water soluble composition as claimed in claim 36 and additionally containing from 25 to 200 weight percent of a crosslinking agent based on the weight of water soluble adduct present.
Claim 64
Dependent Claim
35 words
A coating composition comprising a water soluble composition as claimed in claim 37 and additionally containing from 25 to 200 weight percent of a crosslinking agent based on the weight of water soluble adduct present.
Claim 65
Dependent Claim
35 words
A coating composition comprising a water soluble composition as claimed in claim 38 and additionally containing from 25 to 200 weight percent of a crosslinking agent based on the weight of water soluble adduct present.
Claim 66
Dependent Claim
35 words
A coating composition comprising a water soluble composition as claimed in claim 39 and additionally containing from 25 to 200 weight percent of a crosslinking agent based on the weight of water soluble adduct present.
Claim 67
Dependent Claim
35 words
A coating composition comprising a water soluble composition as claimed in claim 40 and additionally containing from 25 to 200 weight percent of a crosslinking agent based on the weight of water soluble adduct present.
Claim 68
Dependent Claim
33 words
A coating composition comprising a water soluble composition as claimed in claim 41 and additionally containing from 25 to 200 weight percent of hexamethoxymethylmelamine based on the weight of water soluble adduct present.
Claim 69
Dependent Claim
33 words
A coating composition comprising a water soluble compositions as claimed in claim 42 and additionally containing from 25 to 200 weight percent of hexamethoxymethylmelamine based on the weight of water soluble adduct present.
Claim 70
Dependent Claim
33 words
A coating composition comprising a water soluble composition as claimed in claim 43 and additionally containing from 25 to 200 weight percent of hexamethoxymethylmelamine based on the weight of water soluble adduct present.
Claim 71
Dependent Claim
33 words
A coating composition comprising a water soluble composition as claimed in claim 44 and additionally containing from 25 to 200 weight percent of hexamethoxymethylmelamine based on the weight of water soluble adduct present.
Claim 72
Dependent Claim
33 words
A coating composition comprising a water soluble composition as claimed in claim 45 and additionally containing from 25 to 200 weight percent of hexamethoxymethylmelamine based on the weight of water soluble adduct present.
Claim 73
Dependent Claim
33 words
A coating composition comprising a water soluble composition as claimed in claim 46 and additionally containing from 25 to 200 weight percent of hexamethoxymethylmelamine based on the weight of water soluble adduct present.
Claim 74
Dependent Claim
33 words
A coating composition comprising a water soluble composition as claimed in claim 47 and additionally containing from 25 to 200 weight percent of hexamethoxymethylmelamine based on the weight of water soluble adduct present.
Claim 75
Dependent Claim
33 words
A coating composition comprising a water soluble composition as claimed in claim 48 and additionally containing from 25 to 200 weight percent of hexamethoxymethylmelamine based on the weight of water soluble adduct present.
Claim 76
Dependent Claim
33 words
A coating composition comprising a water soluble composition as claimed in claim 49 and additionally containing from 25 to 200 weight percent of hexamethoxymethylmelamine based on the weight of water soluble adduct present.
Claim 77
Dependent Claim
33 words
A coating composition comprising a water soluble composition as claimed in claim 50 and additionally containing from 25 to 200 weight percent of hexamethoxymethylmelamine based on the weight of water soluble adduct present.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-06-19 | 1981-12-19 | 1982-06-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-19 | 1985-12-19 | 1986-06-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-19 | 1989-12-19 | 1990-06-20 | $7700.00 | Window Closed / Lapsed |