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US4261871A Expired / Lapsed US ⏱️ 0.0 years remaining

Low energy-curable high solids coatings

Assignee: Union Carbide Corp
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Filing: 1979-12-13
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Granted: 1981-04-14
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Expires: 1999-12-13
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Abstract

Abstract High solids, low energy curing compositions of (1) a carboxyl-modified polycaprolactone polyol which is the reaction product of a polycaprolactone polyol and an intramolecular carboxylic acid anhydride, (2) a monocarboxylic acid compound, (3) a stannous salt and (4) a polyepoxide. The compositions are useful as inks or coatings.

Inventors

  • 👤 Oliver W. Smith
  • 👤 Joseph V. Koleske

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 08:48
CPC Classifications
C; C09; C09D; C09D167/00; C09D167/04; B; B01; B01D; B01D71/00; B01D71/06; B01D71/66; B01D71/68; C08; C08G; C08G59/00; C08G59/18; C08G59/40; C08G59/42; C08G59/4292; C08G63/00; C08G63/02; C08G63/06; C08G63/66; C08G63/664; C09D11/00; C09D11/02; C09D11/10; C09D11/102; C09D163/00

Claims Analysis

Total Claims: 31
Claim 1
Independent Claim 318 words
A high solids liquid composition comprising (I) from 20 to 60 weight percent of a polycaprolactone adduct, (II) from 5 to 50 weight percent of monocarboxylic acid compound, (III) from 30 to 90 weight percent of a polyepoxide and (IV) from 0.1 to 10 weight percent of a stannous salt catalyst; said percentages based on the combined weight of (I), (II), (III), and (IV); wherein said component (I) comprises a carboxyl-modified polycaprolactone adduct reaction product mixture produced by the reaction of (i) a polycaprolactone polyol and (ii) from 0.5 to 1 carboxylic acid anhydride equivalent for each hydroxyl equivalent present in said polycaprolactone polyol of an intramolecular anhydride of a polycarboxylic acid; said component (II) is a compound of the general formula: HOOC--R--(COOR'").sub.x wherein x is an integer having a value of from 0 to 2; when x is 0, R can be (i) a phenyl group, or (ii) an alkyl group having from 6 to 24 carbon atoms; when x is 1, R can be a --CH═CH-- group; when x is 1 or 2, R can be (iii) a polyvalent alkylene group having from 1 to 12 carbon atoms, or (iv) a polyvalent phenylene group, or (v) a polyvalent naphthylene group; R'" is (i) an alkyl group having from 1 to 8 carbon atoms, or, (ii) a --C n H 2n (OC n H 2n ) m OC p H 2p+1 group, or (iii) a --C n H 2n OOCCX═CH 2 group; n is an integer having a value of 2 to 4; m is an integer having a value of 0 to 10; p is an integer having a value of 1 to 15; and X is hydrogen or methyl; and wherein component (IV) is a stannous acylate of a mono- or dicarboxylic acid having from 1 to 54 carbon atoms or a stannous alkoxide having from 1 to 18 carbon atoms in the alkoxide group.
Claim 2
Dependent Claim 318 words
A high solids liquid composition comprising (I) from 20 to 60 weight percent of a polycaprolactone adduct, (II) from 5 to 50 weight percent of monocarboxylic acid compound, (III) from 30 to 90 weight percent of a polyepoxide and (IV) from 0.1 to 10 weight percent of a stannous salt catalyst; said percentages based on the combined weight of (I), (II), (III), and (IV); wherein said component (I) comprises a carboxyl-modified polycaprolactone adduct reaction product mixture produced by the reaction of (i) a polycaprolactone polyol and (ii) from 0.5 to 1 carboxylic acid anhydride equivalent for each hydroxyl equivalent present in said polycaprolactone polyol of an intramolecular anhydride of a polycarboxylic acid; said component (II) is a compound of the general formula: HOOC--R--(COOR'").sub.x wherein x is an integer having a value of from 0 to 2; when x is 0, R can be (i) a phenyl group, or (ii) an alkyl group having from 6 to 24 carbon atoms; when x is 1, R can be a --CH═CH-- group; when x is 1 or 2, R can be (iii) a polyvalent alkylene group having from 1 to 12 carbon atoms, or (iv) a polyvalent phenylene group, or (v) a polyvalent naphthylene group; R'" is (i) an alkyl group having from 1 to 8 carbon atoms, or, (ii) a --C n H 2n (OC n H 2n ) m OC p H 2p+1 group, or (iii) a --C n H 2n OOCCX═CH 2 group; n is an integer having a value of 2 to 4; m is an integer having a value of 0 to 10; p is an integer having a value of 1 to 15; and X is hydrogen or methyl; and wherein component (IV) is a stannous acylate of a mono- or dicarboxylic acid having from 1 to 54 carbon atoms or a stannous alkoxide having from 1 to 18 carbon atoms in the alkoxide group.
Claim 3
Dependent Claim 23 words
A high solids composition as claimed in claim 1 wherein said polycaprolactone polyol in component (I) has from 2 to 6 hydroxyl groups.
Claim 4
Dependent Claim 23 words
A high solids composition as claimed in claim 1 wherein said polycaprolactone polyol in component (I) has from 2 to 4 hydroxyl groups.
Claim 5
Dependent Claim 27 words
A high solids compositions as claimed in claim 1 said polycaprolactone polyol in component (I) has an average molecular weight of from about 290 to about 3000.
Claim 6
Dependent Claim 28 words
A high solids composition as claimed in claim 1, wherein said polycaprolactone polyol in component (I) has an average molecular weight of from about 300 to about 1000.
Claim 7
Dependent Claim 28 words
A high solids composition as claimed in claim 1, wherein said polycaprolactone polyol in component (I) has an average molecular weight of from about 375 to about 500.
Claim 8
Dependent Claim 22 words
A high solids composition as claimed in claim 1, wherein said polycaprolactone polyol in component (I) is a mixture of polycaprolactone polyols.
Claim 9
Dependent Claim 16 words
A high solids composition as claimed in claim 1 wherein said intramolecular anhydride is phthalic anhydride.
Claim 10
Dependent Claim 24 words
A high solids composition as claimed in claim 1, wherein component (I) is present at a concentration of from 25 to 40 weight percent.
Claim 11
Dependent Claim 24 words
A high solids composition as claimed in claim 1, wherein component (II) is present at a concentration of from 10 to 30 weight percent.
Claim 12
Dependent Claim 24 words
A high solids composition as claimed in claim 1, wherein component (III) is present at a concentration of from 40 to 70 weight percent.
Claim 13
Dependent Claim 24 words
A high solids composition as claimed in claim 1, wherein component (IV) is present at a concentration of from 0.5 to 2 weight percent.
Claim 14
Dependent Claim 26 words
A high solids composition as claimed in claim 1, wherein in component (I) from 0.85 to 0.95 carboxylic acid anhydride equivalent is reacted per hydroxyl equivalent.
Claim 15
Dependent Claim 20 words
A high solids composition as claimed in claim 1, wherein component (II) has a pKa value of less than 4.
Claim 16
Dependent Claim 20 words
A high solids composition as claimed in claim 1, wherein component (II) is a monocarboxylic acid and x is 0.
Claim 17
Dependent Claim 27 words
A high solids composition as claimed in claim 1 wherein component (II) is a monocarboxyl partial ester of a polycarboxylic acid and x is 1 or 2.
Claim 18
Dependent Claim 17 words
A high solids composition as claimed in claim 1, wherein component (III) is a mixture of epoxides.
Claim 19
Dependent Claim 15 words
A high solids composition as claimed in claim 1, wherein a colorant is additionally present.
Claim 20
Dependent Claim 15 words
A high solids composition as claimed in claim 1, wherein component (IV) is stannous octanoate.
Claim 21
Dependent Claim 19 words
A high solids composition as claimed in claim 1, wherein component (II) is the butoxyethyl monoester of phthalic anhydride.
Claim 22
Dependent Claim 16 words
A high solids composition as claimed in claim 1, wherein component (II) is butyl acid maleate.
Claim 23
Dependent Claim 16 words
A high solids composition as claimed in claim 1, wherein component (II) is ethyl acid phthalate.
Claim 24
Dependent Claim 15 words
A high solids composition as claimed in claim 1, wherein component (II) is linoleic acid.
Claim 25
Dependent Claim 34 words
A high solids composition as claimed in claim 1, wherein in component (I) the compound (i) is a polycaprolactone triol having an average molecular weight of 300 and an average hydroxyl number of 560.
Claim 26
Dependent Claim 34 words
A high solids composition as claimed in claim 1, wherein in component (I) the compound (i) is a polycaprolactone triol having an average molecular weight of 540 and an average hydroxyl number of 310.
Claim 27
Dependent Claim 34 words
A high solids composition as claimed in claim 1, wherein in component (I) the compound (i) is a polycaprolactone triol having an average molecular weight of 900 and an average hydroxyl number of 187.
Claim 28
Dependent Claim 21 words
A high solids composition as claimed in claim 1, wherein in component (I) the compound (i) is a chlorinated polycarboxylic acid.
Claim 29
Dependent Claim 15 words
A high solids composition as claimed in claim 1, wherein component (III) is 3,4-epoxycyclohexyl-methyl-3,4-epoxycyclohexane carboxylate.
Claim 30
Dependent Claim 14 words
A high solids composition as claimed in claim 1, wherein component (III) is bis(3,4-epoxy-5-methyl-cyclohexylmethyl)adipate.
Claim 31
Dependent Claim 15 words
A composition as claimed in claim 1 in the form of a cured, dry film.

References Cited (Backward Citations)

US3896303A Cited
US4086294A Cited
US4086293A Cited
US4119593A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-04-13 1984-10-13 1985-04-14 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-04-13 1988-10-13 1989-04-14 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-04-13 1992-10-13 1993-04-14 $7700.00 Window Closed / Lapsed

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