US5510431A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Cure controlled catalyzed mixtures of epoxy resins and curing agents containing mesogenic moieties
Assignee: Dow Chemical Co
•
Filing: 1995-06-01
•
Granted: 1996-04-23
•
Expires: 2015-06-01
Abstract
Abstract Curable compositions containing (A) one or more epoxy resins, one (B) or more curing agents and (C) one or more cure controlling catalysts wherein at least one of components (A) or (B) or both components (A) and (B) contain a mesogenic moiety are prepared. These curable compositions permit processing at higher temperatures and improved properties. They are useful in the preparation of coatings, castings, electrical or laminates or composites and the like.
Inventors
- 👤 Jimmy D. Earls
- 👤 Robert E. Hefner, Jr.
- 👤 James L. Bertram
- 👤 Louis L. Walker
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 23:18
CPC Classifications
C; C09; C09K; C09K19/00; C09K19/04; C09K19/38; C09K19/3804; C09K19/3814; C08; C08G; C08G59/00; C08G59/18; C08G59/20; C08G59/22; C08G59/32; C08G59/68; G; G02; G02F; G02F1/00; G02F1/35; C09K2323/00; C09K2323/05; C09K2323/055; Y; Y10; Y10T; Y10T442/00; Y10T442/30; Y10T442/3472; Y10T442/3528; Y10T442/3569; Y10T442/3585; Y10T442/60; Y10T442/659; Y10T442/67
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
686 words
A curable composition comprising; (A) at least one epoxy resin having an average of more than one vicinal epoxide group per molecule; (B) at least one curing agent for said epoxy resin in an amount which provides from about 0.8 to about 1.5 equivalents of curing agent per epoxide group; and (C) about 0.00005 to about 0.1 mole per epoxide equivalent of a cure controlling catalyst represented by any of the following formulas: ##STR8## wherein each L is independently a hydrocarbyl group or inertly substituted hydrocarbyl group having from 1 to about 18 carbon atoms, which group also can contain one or more oxygen, sulfur or nitrogen atoms or two of such L groups can combine to form a heterocyclic ring containing one or more atoms other than carbon atoms; each L 1 is independently hydrogen or L; Z is nitrogen, phosphorus, sulfur or arsenic; W is a weak nucleophilic anion selected from the group consisting of BF 4 - , BCI 4 - , NO 3 - , F - , Cl--CH 2 --CH 2 --CO 2 --, HO--CH 2 --CH 2 --CO 2 - , SbF 5 - , SbCl 5 - ,AsF 4 - , AsCl 4 - , FP(O) 2 (OH) - , (F) 2 PO(O) 2 - , F 3 B(OH) - , F 2 B(OH) 2 - and C1P(O) 2 (OH) - ; and z has a value of zero or 1 depending on the valence of Z; wherein at least one epoxy resin of component (A) is an epoxy resin which contains at least one mesogenic moiety represented by any one or more of the following formulas: ##STR9## wherein: each R is independently hydrogen or a monovalent hydrocarbyl or hydrocarbyloxy group having from one to about carbon atoms, a halogen atom, a nitro group, a nitrile group or a --CO--R 2 group; R 2 is hydrogen or a monovalent hydrocarbyl group having from one to about 10; n has a value of zero or one; each A is independently a direct single bond, a divalent hydrocarbyl group having from one to about carbon atoms, --O--, --CO--, --SO--, --SO 2 --, --S--, --S--S--, --CR 1 =CR 1 --, --C≡C--, --N═N--, --CR 1 =N--, --N=CR 1 -, --O--CO--, --CO--O--, --S--CO--, --CO--S--, --NR 1 --CO--, --CO--NR 1 --, --CR 1 =N--N=CR 1 --, --CO--CR 1 =CR 1 --, --CR 1 =CR 1 --CO--, --CR 1 =N--O--OC--, --CO--O--N=CR 1 --, --CO--NR 1 --NR 1 --OC--, --CR 1 =CR 1 --O--OC--, --CO--O--CR 1 =CR 1 --, --O--CO--CR 1 =CR 1 --, --CR 1 =CR 1 --CO--O--, --(CHR 1 ) n' --O--CO--CR 1 =CR 1 --, --CR 1 =CR 1 --CO--O--(CHR 1 ) n' --, --(CHR 1 ) n' --CO--O--CR 1 =CR 1 --, --CH 1 =CH 1 --O--CO--(CHR 1 ) n' --, --CH 2 --CH 2 CO--O--, --O--OC--CH 2 --CH 2 --, --C≡C--C≡C--, --CR 1 =CR 1 --CR 1 =CR 1 --, --CR 1 =CR 1 --C≡C--, --C≡C--CR 1 =CR 1 --, --CR 1 =CR 1 --CH 2 --O--OC--, --CO--O--CH 2 --CR 1 =CR 1 , --O--CO--C≡C--CO--O--, --O--CO--CR 1 =CR 1 --CO--O--, --O--CO--CH 2 --CH 2 --CO--O--, --S--CO--CR 1 =CR 1 --CO--S--, --CO--CH 2 --NH--CO--, --CO--NH--CH 2 --CO--, --NH--C(--CH 3 )=CH--CO--, --CO--CH=C(--CH 3 )--NH--, --CR 1 =C(--Cl)--, --C(--Cl)=CR 1 --, --CR 1 =C(--CN)--, --C(--CN)=CR 1 --, --N=C(--CN)--, --C(--CN)=N--, --CR 1 =C(--CN)--CO--O--, --O--CO--C(--CN)=CR 1 --, ##STR10## each A" is a divalent hydrocarbyl group having from one to about 6 carbon atoms; each A 1 is independently a --CO--, --O--CO--, --CO--O--, --CO--S--, --S--CO--, --CO--NR 1 -- or --NR1--CO--; each R 1 is independently hydrogen or a monovalent hydrocarbyl group having from one to about 6 carbon atoms; each R 4 is independently hydrogen or a monovalent hydrocarbyl group having from one to about 3 carbon atoms; n' has a value of one or two; p has a value from zero to about 30; and p 1 has a value of from one to about 30, which, optionally, has been subjected to either (a) the application of an electric field, (b) the application of a magnetic field, (c) drawing or shear forces, or (d) any combination thereof.
Claim 2
Dependent Claim
686 words
A curable composition comprising; (A) at least one epoxy resin having an average of more than one vicinal epoxide group per molecule; (B) at least one curing agent for said epoxy resin in an amount which provides from about 0.8 to about 1.5 equivalents of curing agent per epoxide group; and (C) about 0.00005 to about 0.1 mole per epoxide equivalent of a cure controlling catalyst represented by any of the following formulas: ##STR8## wherein each L is independently a hydrocarbyl group or inertly substituted hydrocarbyl group having from 1 to about 18 carbon atoms, which group also can contain one or more oxygen, sulfur or nitrogen atoms or two of such L groups can combine to form a heterocyclic ring containing one or more atoms other than carbon atoms; each L 1 is independently hydrogen or L; Z is nitrogen, phosphorus, sulfur or arsenic; W is a weak nucleophilic anion selected from the group consisting of BF 4 - , BCI 4 - , NO 3 - , F - , Cl--CH 2 --CH 2 --CO 2 --, HO--CH 2 --CH 2 --CO 2 - , SbF 5 - , SbCl 5 - ,AsF 4 - , AsCl 4 - , FP(O) 2 (OH) - , (F) 2 PO(O) 2 - , F 3 B(OH) - , F 2 B(OH) 2 - and C1P(O) 2 (OH) - ; and z has a value of zero or 1 depending on the valence of Z; wherein at least one epoxy resin of component (A) is an epoxy resin which contains at least one mesogenic moiety represented by any one or more of the following formulas: ##STR9## wherein: each R is independently hydrogen or a monovalent hydrocarbyl or hydrocarbyloxy group having from one to about carbon atoms, a halogen atom, a nitro group, a nitrile group or a --CO--R 2 group; R 2 is hydrogen or a monovalent hydrocarbyl group having from one to about 10; n has a value of zero or one; each A is independently a direct single bond, a divalent hydrocarbyl group having from one to about carbon atoms, --O--, --CO--, --SO--, --SO 2 --, --S--, --S--S--, --CR 1 =CR 1 --, --C≡C--, --N═N--, --CR 1 =N--, --N=CR 1 -, --O--CO--, --CO--O--, --S--CO--, --CO--S--, --NR 1 --CO--, --CO--NR 1 --, --CR 1 =N--N=CR 1 --, --CO--CR 1 =CR 1 --, --CR 1 =CR 1 --CO--, --CR 1 =N--O--OC--, --CO--O--N=CR 1 --, --CO--NR 1 --NR 1 --OC--, --CR 1 =CR 1 --O--OC--, --CO--O--CR 1 =CR 1 --, --O--CO--CR 1 =CR 1 --, --CR 1 =CR 1 --CO--O--, --(CHR 1 ) n' --O--CO--CR 1 =CR 1 --, --CR 1 =CR 1 --CO--O--(CHR 1 ) n' --, --(CHR 1 ) n' --CO--O--CR 1 =CR 1 --, --CH 1 =CH 1 --O--CO--(CHR 1 ) n' --, --CH 2 --CH 2 CO--O--, --O--OC--CH 2 --CH 2 --, --C≡C--C≡C--, --CR 1 =CR 1 --CR 1 =CR 1 --, --CR 1 =CR 1 --C≡C--, --C≡C--CR 1 =CR 1 --, --CR 1 =CR 1 --CH 2 --O--OC--, --CO--O--CH 2 --CR 1 =CR 1 , --O--CO--C≡C--CO--O--, --O--CO--CR 1 =CR 1 --CO--O--, --O--CO--CH 2 --CH 2 --CO--O--, --S--CO--CR 1 =CR 1 --CO--S--, --CO--CH 2 --NH--CO--, --CO--NH--CH 2 --CO--, --NH--C(--CH 3 )=CH--CO--, --CO--CH=C(--CH 3 )--NH--, --CR 1 =C(--Cl)--, --C(--Cl)=CR 1 --, --CR 1 =C(--CN)--, --C(--CN)=CR 1 --, --N=C(--CN)--, --C(--CN)=N--, --CR 1 =C(--CN)--CO--O--, --O--CO--C(--CN)=CR 1 --, ##STR10## each A" is a divalent hydrocarbyl group having from one to about 6 carbon atoms; each A 1 is independently a --CO--, --O--CO--, --CO--O--, --CO--S--, --S--CO--, --CO--NR 1 -- or --NR1--CO--; each R 1 is independently hydrogen or a monovalent hydrocarbyl group having from one to about 6 carbon atoms; each R 4 is independently hydrogen or a monovalent hydrocarbyl group having from one to about 3 carbon atoms; n' has a value of one or two; p has a value from zero to about 30; and p 1 has a value of from one to about 30, which, optionally, has been subjected to either (a) the application of an electric field, (b) the application of a magnetic field, (c) drawing or shear forces, or (d) any combination thereof.
Claim 3
Dependent Claim
34 words
A curable composition of claim 1 wherein component (C) is ethyl(tritolyl)phosphonium tetrahaloborate, ethyl(tritolyl)ammonium tetrahaloborate, tetrabutyl phosphonium tetrahaloborate, benzyltrimethylammonium tetrahaloborate, tetrabutylammonium tetrahaloborate, triethylamine.tetrahaloboric acid complex, tributylamine.tetrahaloboric acid complex, N,N'-dimethyl-1,2-diamingethane.tetrahaloboric acid complex or any combination thereof.
Claim 4
Dependent Claim
36 words
A curable composition of claim 1 which has been subjected to either (a) the application of an electric field, (b) the application of a magnetic field, (c) drawing or shear forces, or (d) any combination thereof.
Claim 5
Dependent Claim
36 words
A curable composition of claim 2 which has been subjected to either (a) the application of an electric field, (b) the application of a magnetic field, (c) drawing or shear forces, or (d) any combination thereof.
Claim 6
Dependent Claim
37 words
A curable composition of claim 1 which has not been subjected to either (a) the application of an electric field, (b) the application of a magnetic field, (c) drawing or shear forces, or (d) any combination thereof.
Claim 7
Dependent Claim
37 words
A curable composition of claim 2 which has not been subjected to either (a) the application of an electric field, (b) the application of a magnetic field, (c) drawing or shear forces, or (d) any combination thereof.
References Cited (Backward Citations)
US3725341A
Cited
US3738862A
Cited
US4946817A
Cited
US4594291A
Cited
US4725652A
Cited
US5134239A
Cited
US4717674A
Cited
EP0328020A2
Cited
US4925901A
Cited
US5266661A
Cited
US5266660A
Cited
US5270406A
Cited
US5270405A
Cited
US5270404A
Cited
EP0430143A2
Cited
US5140079A
Cited
US5169473A
Cited
US5266405A
Cited
EP0473935A2
Cited
US5281675A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1999-04-23 | 1999-10-23 | 2000-04-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-04-23 | 2003-10-23 | 2004-04-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-04-23 | 2007-10-23 | 2008-04-23 | $7700.00 | Window Closed / Lapsed |