US5140079A
Expired / Lapsed
US
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Latent, curable, catalyzed mixtures of epoxy-containing and phenolic-hydroxyl-containing compounds containing compounds or complexes formed from contacting organic phosphines or arsines with weak nucleophilic acids
Assignee: Dow Chemical Co
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Filing: 1991-04-15
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Granted: 1992-08-18
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Expires: 2011-04-15
Abstract
Abstract The products resulting from contacting an organic phosphine or arsine with an inorganic acid having a weak nucleophilic anion provide for relatively stable compositions when admixed with a compound containing an average of more than one vicinal epoxide group per molecule and which optionally contains a compound containing an average of more than one phenolic hydroxyl group per molecule.
Inventors
- 👤 John W. Muskopf
- 👤 Louis L. Walker
- 👤 James L. Bertram
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 14:08
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/68; C08G59/688; B; B01; B01J; B01J31/00; B01J31/02; B01J31/0234; B01J31/0255; B01J31/0267; B01J31/0272; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/50; C07F9/66; C07F9/70; C07F9/74
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
273 words
A composition comprising (A) at least one compound containing an average of more than one epoxide group per molecule; and (B) at least one of ( 1) the product resulting from contacting (a) at least one organic arsine or organic phosphine compound, said organic phosphine compound being represented by the following formula III ##STR5## wherein each R, R 1 and R 2 is independently a hydrocarbyl group having from 1 to about 18 carbon atoms or two of said R, R 1 , or R 2 groups can combine to form a heterocyclic ring, and Z is P, with (b) an inorganic acid having a weak-nucleophilic anion or a combination of said acids; or (2) the product resulting from contacting (a) at least one adduct of an acid having a relatively strong-nucleophilic anion and an organic phosphine or arsine compound with (b) an inorganic acid or metal salt of an inorganic acid, said acid having a weak-nucleophilic anion or a combination of said acids or metal salts; wherein (i) components (a) and (b) are contacted in quantities which permit the composition to satisfy the viscosity requirements of the composition after storage at 50° C. for 14 days; and (ii) the mixture of components (A), and (B), when dissolved in 20 to 40 percent by weight of a suitable solvent or solvent mixture, has a viscosity measured at 25° C. of 75% or less than the viscosity of a like composition except that the catalyst consists only of component (a), said viscosity being determined after storage for 14 days at 50° C.; and wherein component (B1a) is not triphenylphosphine when component (B1b) is tetrafluoroborate.
Claim 2
Dependent Claim
273 words
A composition comprising (A) at least one compound containing an average of more than one epoxide group per molecule; and (B) at least one of ( 1) the product resulting from contacting (a) at least one organic arsine or organic phosphine compound, said organic phosphine compound being represented by the following formula III ##STR5## wherein each R, R 1 and R 2 is independently a hydrocarbyl group having from 1 to about 18 carbon atoms or two of said R, R 1 , or R 2 groups can combine to form a heterocyclic ring, and Z is P, with (b) an inorganic acid having a weak-nucleophilic anion or a combination of said acids; or (2) the product resulting from contacting (a) at least one adduct of an acid having a relatively strong-nucleophilic anion and an organic phosphine or arsine compound with (b) an inorganic acid or metal salt of an inorganic acid, said acid having a weak-nucleophilic anion or a combination of said acids or metal salts; wherein (i) components (a) and (b) are contacted in quantities which permit the composition to satisfy the viscosity requirements of the composition after storage at 50° C. for 14 days; and (ii) the mixture of components (A), and (B), when dissolved in 20 to 40 percent by weight of a suitable solvent or solvent mixture, has a viscosity measured at 25° C. of 75% or less than the viscosity of a like composition except that the catalyst consists only of component (a), said viscosity being determined after storage for 14 days at 50° C.; and wherein component (B1a) is not triphenylphosphine when component (B1b) is tetrafluoroborate.
Claim 3
Dependent Claim
99 words
A composition of claim 1 wherein (i) in component (A), said epoxide groups are glycidyl ether groups; (ii) component (B-2-a) is an adduct of an acid having a relatively strong-nucleophilic anion and an organic phosphine; and (iii) the mixture of components (A), and (B), when dissolved in 20 to 40 percent by weight of a suitable solvent or solvent mixture, has a viscosity measured at 25° C. of 75% or less than the viscosity of a like composition except that the catalyst consists only of component (a), said viscosity being determined after storage for 14 days at 50° C.
Claim 4
Dependent Claim
98 words
A composition of claim 1 wherein component (B) is a product resulting from contacting (a) at least one organic phosphine with (b) an inorganic acid having a weak-nucleophilic anion or a combination of said acids; and the mixture of components (A), and (B), when dissolved in 20 to 40 percent by weight of a suitable solvent or solvent mixture, has a viscosity measured at 25° C. of 10% or less than the viscosity of a like composition except that the catalyst consists only of component (a), said viscosity being determined after storage for 14 days at 50° C.
Claim 5
Dependent Claim
48 words
A composition of claim 3 wherein ##STR6## component (b) is fluoboric acid, fluoarsenic acid, fluoantimonic acid, fluophosphoric acid, chloroboric acid, chloroarsenic acid, chloroantimonic acid, chlorophosphoric acid, perchloric acid, chloric acid, bromic acid, iodic acid, Group I or Group II metal salts of said acids, or any combination thereof.
Claim 6
Dependent Claim
35 words
A composition of claim 4 wherein component (b) is fluoboric acid, fluoantimonic acid, fluophosphoric acid, chloroboric acid, chloroarsenic acid, chloroantimonic acid, chlorophosphoric acid, perchloric acid, chloric acid, bromic acid, iodic acid, or any combination thereof.
Claim 7
Dependent Claim
24 words
A composition of claim 5 wherein said organic phosphine is triethylphosphine, or tributylphosphine, or any combination thereof; and component (b) is HBF 4 .
Claim 8
Dependent Claim
253 words
A composition comprising (A) at least one compound containing an average of more than one epoxide group per molecule; (B) at least one compound containing an average of more than one aromatic hydroxyl group per molecule; and (C) at least one catalyst selected from the group consisting of (1) the product resulting from contacting (a) at least one organic phosphine or arsine with (b) an inorganic acid having a weak-nucleophilic anion or a combination of said acids; and (2) the product resulting from contacting (a) at least one adduct of an acid having a relatively strong-nucleophilic anion and an organic phosphine or arsine compound with (b) an inorganic acid or metal salt of an inorganic acid, said acid having a weak-nucleophilic anion or a combination of such acids or metal salts; wherein (i) components (a) and (b) are contacted in quantities which permit the composition to satisfy the viscosity requirements of the composition after storage at 50° C. for 14 days; (ii) components (A) and (B) are present in quantities which provide a ratio of aromatic hydroxyl groups to epoxide group of from about 0.05:1 to about 20:1; and (iii) a mixture of components (A), (B), and (C), when dissolved in 20 to 40 percent by weight of a suitable solvent or solvent mixture, has a viscosity measured at 25° C. of 75% or less than the viscosity of a like composition except that the catalyst consists only of component (a), said viscosity being determined after storage for 14 days at 50° C.
Claim 9
Dependent Claim
253 words
A composition comprising (A) at least one compound containing an average of more than one epoxide group per molecule; (B) at least one compound containing an average of more than one aromatic hydroxyl group per molecule; and (C) at least one catalyst selected from the group consisting of (1) the product resulting from contacting (a) at least one organic phosphine or arsine with (b) an inorganic acid having a weak-nucleophilic anion or a combination of said acids; and (2) the product resulting from contacting (a) at least one adduct of an acid having a relatively strong-nucleophilic anion and an organic phosphine or arsine compound with (b) an inorganic acid or metal salt of an inorganic acid, said acid having a weak-nucleophilic anion or a combination of such acids or metal salts; wherein (i) components (a) and (b) are contacted in quantities which permit the composition to satisfy the viscosity requirements of the composition after storage at 50° C. for 14 days; (ii) components (A) and (B) are present in quantities which provide a ratio of aromatic hydroxyl groups to epoxide group of from about 0.05:1 to about 20:1; and (iii) a mixture of components (A), (B), and (C), when dissolved in 20 to 40 percent by weight of a suitable solvent or solvent mixture, has a viscosity measured at 25° C. of 75% or less than the viscosity of a like composition except that the catalyst consists only of component (a), said viscosity being determined after storage for 14 days at 50° C.
Claim 10
Dependent Claim
122 words
A composition of claim 7 wherein (i) in component (A), said epoxide groups are glycidyl ether groups; (ii) component (B) is a biphenol, bisphenol or a phenol- or substituted phenol-aldehyde novolac resin; (iii) component (C-1-a) is an organic phosphine; (iv) component (C-2-a) is an adduct of an acid having a relatively strong-nucleophilic anion and an organic phosphine; and (v) the mixture of components (A), (B) and (C), when dissolved in 20 to 40 percent by weight of a suitable solvent or solvent mixture, has a viscosity measured at 25° C. of 10% or less than the viscosity of a like composition except that the catalyst consists only of component (a), said viscosity being determined after storage for 14 days at 50° C.
Claim 11
Dependent Claim
99 words
A composition of claim 8 wherein component (C) is a product resulting from contacting (a) at least one organic phosphine with (b) an inorganic acid having a weak-nucleophilic anion or a combination of said acids; and the mixture of components (A), (B) and (C), when dissolved in 20 to 40 percent by weight of a suitable solvent or solvent mixture, has a viscosity measured at 25° C. of 1% or less than the viscosity of a like composition except that the catalyst consists only of component (a), said viscosity being determined after storage for 14 days at 50° C.
Claim 12
Dependent Claim
146 words
A composition of claim 9 wherein component (a) is an organic phosphine represented by the following formulas III or IV ##STR7## wherein each R, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is independently a hydrocarbyl group having from 1 to about 18 carbon atoms or two of said R, R 1 , or R 2 groups or R 3 and R 4 or R 5 and R 6 groups can combine to form a heterocyclic ring; and Z is P; Z' is a divalent hydrocarbyl group having from 1 to about 10 carbon atoms; and component (b) is fluoboric acid, fluoarsenic acid, fluoantimonic acid, fluophosphoric acid, chloroboric acid, chloroarsenic acid, chloroantimonic acid, chlorophosphoric acid, perchloric acid, chloric acid, bromic acid, iodic acid, Group I or Group II metal salts of said acids, or any combination thereof.
Claim 13
Dependent Claim
68 words
A composition of claim 10 wherein each R, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is independently a hydrocarbyl group having from 1 to about 9 carbon atoms; and component (b) is fluoboric acid, fluoantimonic acid, fluophosphoric acid, chloroboric acid, chloroarsenic acid, chloroantimonic acid, chlorophosphoric acid, perchloric acid, chloric acid, bromic acid, iodic acid, or any combination thereof.
Claim 14
Dependent Claim
25 words
A composition of claim 11 wherein said organic phosphine is triethylphosphine, tributylphosphine, or 1,3-bis(diphenylphosphino)propane, or any combination thereof; and component (b) is HBF 4 .
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-08-18 | 1996-02-17 | 1996-08-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-08-18 | 2000-02-17 | 2000-08-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-08-18 | 2004-02-17 | 2004-08-18 | $7700.00 | Window Closed / Lapsed |