Patent US4374181A successfully refreshed from Google Patents.
US4374181A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Vapor permeation curable coatings for reaction injection molded parts
Assignee: Sherwin Williams Co
•
Filing: 1981-09-14
•
Granted: 1983-02-15
•
Expires: 2001-09-14
Abstract
Abstract Disclosed is a coating composition rapidly curable at room temperature in the presence of a vaporous tertiary amine catalyst which coating composition is ideally suited for coating reaction injection molded (RIM) urethane parts, upholstery vinyl, and sheet molding compound (SMC). The flexible coating composition of the present invention preferably comprises an aromatic hydroxyl-functional condensation product, a multi-isocyanate curing agent, and a volatile organic solvent therefor. The aromatic hydroxyl functional condensation product is made from (a) a linear aliphatic dibasic acid, (b) a linear aliphatic glycol, (c) a combination of a linear aliphatic glycol and aromatic dicarboxylic acid, and (d) a phenol capping agent. The sum of the methylene groups of the linear aliphatic dibasic acid (a) and linear aliphatic glycol (b) range from between about 10 and 13. For thicker coat ings of the coating composition of the present invention, a desirable post-conditioning thermal treatment is provided to enhance adhesion of the coating composition.
Inventors
- 👤 James R. Blegen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 22:57
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/16; C08G18/18; C08G18/1891; C08J; C08J7/00; C08J7/12; C08J7/16; C08G18/28; C08G18/40; C08G18/42; C08G18/4205; C08G18/4266; C08G18/4286; C08J7/04; C08J7/0427; C08J7/043; C08J7/046; C08L; C08L67/00; C08L67/06; C08J2375/00; C08J2375/04; C08J2475/00; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31551; Y10T428/31554; Y10T428/31573; Y10T428/31591
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
202 words
A coating composition rapidly curable at room temperature in the presence of vaporous tertiary amine catalyst and possessing a pot life of at least about 4 hours in an open pot, comprising: (1) an aromatic hydroxyl-functional condensation product made by condensing the following ingredients: (a) a linear aliphatic dibasic acid; (b) a linear aliphatic glycol, where the sum of the methylene groups of (a) and (b) is between 10 and 13 and where up to about one-half of (a) or (b) can be replaced with a C 6 -C 8 cycloaliphatic dibasic acid or diol; (c) the combination of a linear aliphatic glycol and aromatic dicarboxylic acid, or a bis(hydroxyalkyl) adduct of an aromatic diol and a linear aliphatic dicarboxylic acid, (d) a phenol capping agent, where said condensation product (1) has a molecular weight of between about 1,000 and 4,000 an equivalent (solids) weight of between about 250 and 1,000, and substantially no aliphatic hydroxyl groups; (2) a multi-isocyanate curing agent; (3) a volatile organic solvent for said aromatic hydroxyl-functional condensation product and for said multi-isocyanate curing agent, the ratio of aromatic hydroxyl equivalents of said condensation product to the isocyanate equivalents of said multi-isocyanate being between about 1:1 and 1:2.
Claim 2
Dependent Claim
202 words
A coating composition rapidly curable at room temperature in the presence of vaporous tertiary amine catalyst and possessing a pot life of at least about 4 hours in an open pot, comprising: (1) an aromatic hydroxyl-functional condensation product made by condensing the following ingredients: (a) a linear aliphatic dibasic acid; (b) a linear aliphatic glycol, where the sum of the methylene groups of (a) and (b) is between 10 and 13 and where up to about one-half of (a) or (b) can be replaced with a C 6 -C 8 cycloaliphatic dibasic acid or diol; (c) the combination of a linear aliphatic glycol and aromatic dicarboxylic acid, or a bis(hydroxyalkyl) adduct of an aromatic diol and a linear aliphatic dicarboxylic acid, (d) a phenol capping agent, where said condensation product (1) has a molecular weight of between about 1,000 and 4,000 an equivalent (solids) weight of between about 250 and 1,000, and substantially no aliphatic hydroxyl groups; (2) a multi-isocyanate curing agent; (3) a volatile organic solvent for said aromatic hydroxyl-functional condensation product and for said multi-isocyanate curing agent, the ratio of aromatic hydroxyl equivalents of said condensation product to the isocyanate equivalents of said multi-isocyanate being between about 1:1 and 1:2.
Claim 3
Dependent Claim
36 words
The coating composition of claim 1 wherein said linear aliphatic dibasic acid (1)(a) is a C 6 -C 10 linear aliphatic dibasic acid and said linear aliphatic glycol (1)(b) is a C 4 -C 8 glycol.
Claim 4
Dependent Claim
33 words
The coating composition of claim 2 wherein the number of methylene groups of said linear aliphatic dibasic acid (1)(a) does not equal the number of methylene groups in said linear aliphatic glycol (1)(b).
Claim 5
Dependent Claim
44 words
The coating composition of claim 1 wherein said combination (1)(c) is of a linear aliphatic glycol and an aromatic dicarboxylic acid wherein said aromatic dicarboxylic acid is isophthalic acid or terephthalic acid, and said linear aliphatic glycol is a C 4 -C 6 glycol.
Claim 6
Dependent Claim
27 words
The coating composition of claim 4 wherein said linear aliphatic dibasic acid (1)(a) is azelaic acid and said linear aliphatic glycol (1)(b) is a C 4 glycol.
Claim 7
Dependent Claim
42 words
The coating composition of claim 1 wherein said phenol capping agent (1)(d) is represented by: ##STR3## where: R 1 is an H, C 1 -C 8 alkyl group, R 3 is a sigma bond or a C 1 -C 8 polymethylene group.
Claim 8
Dependent Claim
25 words
The coating composition of claim 6 wherein for said diphenolic acid, R 2 equals CH 3 and R 3 is --CH 2 --CH 2 --.
Claim 9
Dependent Claim
20 words
The coating composition of claim 6 wherein said phenol capping agent is selected from diphenolic acid or bisphenol acetic acid.
Claim 10
Dependent Claim
32 words
The coating composition of claim 1 wherein said condensation product (1) has a molecular weight of between about 2,000 and 3,000 and an equivalent (solids) weight of between about 500 and 750.
Claim 11
Dependent Claim
27 words
The coating composition of claim 1 wherein said aromatic hydroxylfunctional condensation product has an aromatic content of at least about 30% by weight of said condensation product.
Claim 12
Dependent Claim
40 words
The coating composition of claim 1 wherein said aromatic hydroxylfunctional condensation product is made by condensing the following ingredients: 1 mole of isophthalic acid, 6 moles of azelaic acid, 8 moles of 1,4 butanediol, and 2 moles of diphenolic acid.
Claim 13
Dependent Claim
46 words
The coating composition of claim 1 wherein said aromatic hydroxyl functional condensation product is made by condensing the following ingredients: 1 mole of isophthalic acid, 6 moles of azelaic acid, 4 moles of 1,4 butanediol, 4 moles of cyclohexane dimethanol, and 2 moles of diphenolic acid.
Claim 14
Dependent Claim
41 words
The coating composition of claim 1 wherein said aromatic hydroxyl functional condensation product is made by condensing the following ingredients: 6 moles of azelaic acid, 8 moles of 1,4 butanediol, 1 mole of terephthalic acid, and 2 moles of diphenolic acid.
Claim 15
Dependent Claim
41 words
The coating composition of claim 1 wherein said aromatic hydroxyl functional condensation product is made by condensing the following ingredients: 1 mole of isophthalic acid, 6 moles of azelaic acid, 9 moles of 1,6-hexane diol, and 2 moles of diphenolic acid.
Claim 16
Dependent Claim
35 words
The coating composition of claim 1 wherein said multi-isocyanate curing agent comprises between about 10 and 80% by weight of an aromatic multi-isocyanate and between about 90 and 20% by weight of an aliphatic multi-isocyanate.
Claim 17
Dependent Claim
30 words
The coating composition of claim 1 wherein said ratio of aromatic hydroxyl equivalents of said condensation product of the isocyanate equivalents of said multi-isocyanate is between about 1:1.1 and 1:1.7.
Claim 18
Dependent Claim
24 words
The coating composition of claim 1 wherein said volatile organic solvent comprises a ketone, a carboxylic acid ester, an aromatic solvent, or mixtures thereof.
Claim 19
Independent Claim
245 words
A method for coating a substrate with a film of a coating composition rapidly curable at room temperature in the presence of a vaporous tertiary amine catalyst and possessing a pot life of at least about 4 hours in an open pot, which comprises: (A) applying a film of said coating composition to said substrate, said coating composition comprising: (1) an aromatic hydroxyl-functional condensation product made by condensing the following ingredients: (a) a linear aliphatic dibasic acid; (b) a linear aliphatic glycol, where the sum of the methylene groups of (a) and (b) is between 10 and 13 and where up to about one-half of (a) or (b) can be replaced with a C 6 -C 8 cycloaliphatic dibasic acid or diol; (c) the combination of a linear aliphatic glycol and aromatic dicarboxylic acid, or an aromatic diol and a linear aliphatic dicarboxylic acid, (d) a phenol capping agent, where said condensation product (1) has a molecular weight of between about 1,000 and 4,000, an equivalent (solids) weight of between about 250 and 1,000, and substantially no aliphatic hydroxyl groups; (2) a multi-isocyanate curing agent; (3) a volatile organic solvent for said aromatic hydroxyl-functional condensation product and for said multi-isocyanate curing agent, the ratio of aromatic hydroxyl equivalents of said condensation product to the isocyanate equivalents of said multi-isocyanate being between about 1:1 and 1:2, (B) exposing said coated substrate to a vaporous tertiary amine catalyst to rapidly cure said coating at about room temperature.
Claim 20
Independent Claim
245 words
A method for coating a substrate with a film of a coating composition rapidly curable at room temperature in the presence of a vaporous tertiary amine catalyst and possessing a pot life of at least about 4 hours in an open pot, which comprises: (A) applying a film of said coating composition to said substrate, said coating composition comprising: (1) an aromatic hydroxyl-functional condensation product made by condensing the following ingredients: (a) a linear aliphatic dibasic acid; (b) a linear aliphatic glycol, where the sum of the methylene groups of (a) and (b) is between 10 and 13 and where up to about one-half of (a) or (b) can be replaced with a C 6 -C 8 cycloaliphatic dibasic acid or diol; (c) the combination of a linear aliphatic glycol and aromatic dicarboxylic acid, or an aromatic diol and a linear aliphatic dicarboxylic acid, (d) a phenol capping agent, where said condensation product (1) has a molecular weight of between about 1,000 and 4,000, an equivalent (solids) weight of between about 250 and 1,000, and substantially no aliphatic hydroxyl groups; (2) a multi-isocyanate curing agent; (3) a volatile organic solvent for said aromatic hydroxyl-functional condensation product and for said multi-isocyanate curing agent, the ratio of aromatic hydroxyl equivalents of said condensation product to the isocyanate equivalents of said multi-isocyanate being between about 1:1 and 1:2, (B) exposing said coated substrate to a vaporous tertiary amine catalyst to rapidly cure said coating at about room temperature.
Claim 21
Dependent Claim
21 words
The method of claim 18 wherein said substrate is selected from sheet molding compound, reaction injection molding urethane, and upholstery vinyl.
Claim 22
Dependent Claim
18 words
The method of claim 19 wherein said substrate is selected from reaction injection molding urethane and upholstery vinyl.
Claim 23
Dependent Claim
82 words
The method of claim 18 or 20 wherein said coating thickness of said film of said coating composition or multiple films of said coating composition range in thickness from between about 1 and 4 mils, and said vaporous tertiary amine-cured film of said coating composition on said substrate is subjected thereafter to a thermal conditioning step comprising maintaining said cured film at a temperature of between about 50° and 150° C. for a time ranging from between about 1 and 3 minutes.
Claim 24
Dependent Claim
19 words
The method of claim 21 wherein said thermal conditioning is practiced at about 120° C. for about 1 minute.
Claim 25
Dependent Claim
35 words
The method of claim 18 wherein said linear aliphatic dibasic acid (1)(a) is a C 6 -C 10 linear aliphatic dibasic acid and said linear aliphatic glycol (1)(b) is a C 4 -C 8 glycol.
Claim 26
Dependent Claim
43 words
The method of claim 18 wherein said combination (1)(c) is of a linear aliphatic glycol and an aromatic dicarboxylic acid wherein said aromatic dicarboxylic acid is isophthalic acid or terephthalic acid, and said linear aliphatic glycol is a C 4 -C 6 glycol.
Claim 27
Dependent Claim
26 words
The method of claim 24 wherein said linear aliphatic dibasic acid (1)(a) is azelaic acid and said linear aliphatic glycol (1)(c) is a C 4 glycol.
Claim 28
Dependent Claim
23 words
The method of claim 18 wherein said catalyst is selected from triethyl amine, dimethyl ethyl amine, cyclohexyl dimethyl amine, and methyl diethyl amine.
Claim 29
Dependent Claim
230 words
A composite article comprising a substrate selected from reaction injection molding urethane and upholstery vinyl having an adherent cured film of a curable coating composition thereon, said film at a thickness of between about 1 and 4 mils, said film being the cured residue of said coating composition after exposure to a vaporous tertiary amine catalyst, said coating composition comprising: (1) an aromatic hydroxyl-functional condensation product made by condensing the following ingredients: (a) a linear aliphatic dibasic acid; (b) a linear aliphatic glycol, where the sum of the methylene groups of (a) and (b) is between 10 and 13 and where up to about one-half of (a) or (b) can be replaced with a C 6 -C 8 cycloaliphatic dibasic acid or diol; (c) the combination of a linear aliphatic glycol and aromatic dicarboxylic acid, or a bis(hydroxyalkyl) adduct of an aromatic diol and a linear aliphatic dicarboxylic acid, (d) a phenol capping agent, where said condensation product (1) has a molecular weight of between about 1,000 and 4,000 an equivalent (solids) weight of between about 250 and 1,000, and substantially no aliphatic hydroxyl groups; (2) a multi-isocyanate curing agent; (3) a volatile organic solvent for said aromatic hydroxyl-functional condensation product and for said multi-isocyanate curing agent, the ratio of aromatic hydroxyl equivalents of said condensation product to the isocyanate equivalents of said multi-isocyanate being between about 1:1 and 1:2.
Claim 30
Dependent Claim
230 words
A composite article comprising a substrate selected from reaction injection molding urethane and upholstery vinyl having an adherent cured film of a curable coating composition thereon, said film at a thickness of between about 1 and 4 mils, said film being the cured residue of said coating composition after exposure to a vaporous tertiary amine catalyst, said coating composition comprising: (1) an aromatic hydroxyl-functional condensation product made by condensing the following ingredients: (a) a linear aliphatic dibasic acid; (b) a linear aliphatic glycol, where the sum of the methylene groups of (a) and (b) is between 10 and 13 and where up to about one-half of (a) or (b) can be replaced with a C 6 -C 8 cycloaliphatic dibasic acid or diol; (c) the combination of a linear aliphatic glycol and aromatic dicarboxylic acid, or a bis(hydroxyalkyl) adduct of an aromatic diol and a linear aliphatic dicarboxylic acid, (d) a phenol capping agent, where said condensation product (1) has a molecular weight of between about 1,000 and 4,000 an equivalent (solids) weight of between about 250 and 1,000, and substantially no aliphatic hydroxyl groups; (2) a multi-isocyanate curing agent; (3) a volatile organic solvent for said aromatic hydroxyl-functional condensation product and for said multi-isocyanate curing agent, the ratio of aromatic hydroxyl equivalents of said condensation product to the isocyanate equivalents of said multi-isocyanate being between about 1:1 and 1:2.
Claim 31
Dependent Claim
14 words
The composite article of claim 27 wherein said substrate comprises reaction injection molding urethane.
Claim 32
Dependent Claim
36 words
The composite article of claim 27 wherein said linear aliphatic dibasic acid (1)(a) is a C 6 -C 10 linear aliphatic dibasic acid and said linear aliphatic glycol (1)(b) is a C 4 -C 8 glycol.
Claim 33
Dependent Claim
44 words
The composite article of claim 27 wherein said combination (1)(c) is of a linear aliphatic glycol and an aromatic dicarboxylic acid wherein said aromatic dicarboxylic acid is isophthalic acid or terephthalic acid, and said linear aliphatic glycol is a C 4 -C 6 glycol.
Claim 34
Dependent Claim
27 words
The composite article of claim 30 wherein said linear aliphatic dibasic acid (1)(a) is azelaic acid and said linear aliphatic glycol (1)(b) is a C 4 glycol.
Claim 35
Dependent Claim
40 words
The composite article of claim 28 wherein said aromatic hydroxylfunctional condensation product is made by condensing the following ingredients: 1 mole of isophthalic acid, 6 moles of azelaic acid, 8 moles of 1,4 butanediol, and 2 moles of diphenolic acid.
References Cited (Backward Citations)
US2967117A
Cited
US2657151A
Cited
US3409579A
Cited
US3429848A
Cited
GB1351881A
Cited
US3789044A
Cited
US3676392A
Cited
US3836491A
Cited
GB1369351A
Cited
US3822226A
Cited
US3874898A
Cited
US3933727A
Cited
US4179427A
Cited
US4267239A
Cited
US4298658A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-02-14 | 1986-08-16 | 1987-02-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-02-14 | 1990-08-16 | 1991-02-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-02-14 | 1994-08-16 | 1995-02-15 | $7700.00 | Window Closed / Lapsed |