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US4514556A
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4,4'-Methylene-bis-(2-ethyl-5-methyl imidazole) and methods of producing and using the same
Assignee: Shikoku Chemicals Corp
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Filing: 1984-03-29
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Granted: 1985-04-30
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Expires: 2004-03-29
Abstract
Abstract The disclosure relates to a novel compound 4,4'-methylene-bis-(2-ethyl-5-methyl imidazole) represented by the structural formula ##STR1## A method is provided for producing the novel compound subjecting formaldehyde or a methylenizing agent to thermal reaction with 2-ethyl-4-methyl imidazole in the presence of a catalyst; and a method of curing an epoxy compound and a method of accelerating curing the epoxy compound and a method of inhibiting crystallization of 2-ethyl-4-methyl imidazole, respectively by use of the new compound.
Inventors
- 👤 Natsuo Sawa
- 👤 Toshihiro Suzuki
- 👤 Shinji Okazaki
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 14:36
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/40; C08G59/50; C07; C07D; C07D233/00; C07D233/54; C07D233/56; C08G59/5046; C08G59/5053; C08G59/5073
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
8 words
4,4'-methylene-bis-(2-ethyl-5-methyl imidazole) represented by the structural formula ##STR10##
Claim 2
Dependent Claim
8 words
4,4'-methylene-bis-(2-ethyl-5-methyl imidazole) represented by the structural formula ##STR10##
Claim 3
Independent Claim
32 words
A method of producing 4,4'-methylene-bis-(2-ethyl-5-methyl imidazole), comprising the step of subjecting at least one of formaldehyde and a methylenizing agent to thermal reaction with 2-ethyl-4-methyl imidazole in the presence of a catalyst.
Claim 4
Independent Claim
32 words
A method of producing 4,4'-methylene-bis-(2-ethyl-5-methyl imidazole), comprising the step of subjecting at least one of formaldehyde and a methylenizing agent to thermal reaction with 2-ethyl-4-methyl imidazole in the presence of a catalyst.
Claim 5
Dependent Claim
19 words
The method of claim 2, wherein said methylenizing agent is selected from the group consisting of paraform and 1,3-dioxolane.
Claim 6
Dependent Claim
29 words
The method of claim 2, wherein said thermal reaction is made with the use of a solvent selected from the group consisting of water, methanol, ethanol, n-butanol, and ethylene-glycol.
Claim 7
Dependent Claim
24 words
The method of claim 2, wherein said catalyst is selected from the group consisting of sodium hydroxide, potassium hydroxide, sodium amide and lithium carbonate.
Claim 8
Dependent Claim
16 words
The method of claim 2, wherein said heating temperature is in the range of 20°-150° C.
Claim 9
Dependent Claim
30 words
The method of claim 2 wherein the mole ratio between 2-ethyl-4-methyl imidazole and at least one of formaldehyde and a methylenizing agent is in the range of 2:1 to 0.13:1.
Claim 10
Independent Claim
34 words
A method of curing an epoxy compound, comprising the steps of: 4,4'-methylene-bis-(2-ethyl-5-methyl imidazole) with an epoxy compound having more than one epoxy group on an average in a molecule; and, heating the resulting mixture.
Claim 11
Independent Claim
34 words
A method of curing an epoxy compound, comprising the steps of: 4,4'-methylene-bis-(2-ethyl-5-methyl imidazole) with an epoxy compound having more than one epoxy group on an average in a molecule; and, heating the resulting mixture.
Claim 12
Independent Claim
44 words
A method of accelerating curing of an epoxy compound, comprising the steps of: mixing 4,4'-methylene-bis-methyl imidazole with a curing agent into an epoxy resin to be cured, having more than one epoxy group on an average in a molecule; and, heating the resulting mixture.
Claim 13
Independent Claim
44 words
A method of accelerating curing of an epoxy compound, comprising the steps of: mixing 4,4'-methylene-bis-methyl imidazole with a curing agent into an epoxy resin to be cured, having more than one epoxy group on an average in a molecule; and, heating the resulting mixture.
Claim 14
Independent Claim
18 words
A method of inhibiting crystallization of 2-ethyl-4-methyl imidazole, comprising the step of mixing 4,4'-methylene-bis-(2-ethyl-5-methyl imidazole) with 2-ethyl-4-methyl imidazole.
Claim 15
Independent Claim
18 words
A method of inhibiting crystallization of 2-ethyl-4-methyl imidazole, comprising the step of mixing 4,4'-methylene-bis-(2-ethyl-5-methyl imidazole) with 2-ethyl-4-methyl imidazole.
Claim 16
Dependent Claim
27 words
The method of claim 10, comprising the step of mixing the 4,4'-methylene-bis-(2-ethyl-5-methyl imidazole) and 2-ethyl-4-methyl imidazole by a weight ratio in the range of 0.1:99.9 to 3.0:97.0.
Claim 17
Dependent Claim
16 words
The method of claim 6, wherein said heating temperature is in the range of 70°-130° C.
Claim 18
Dependent Claim
28 words
The method of claim 7, wherein said mole ratio between 2-ethyl-4-methyl imidazole and at least one of formaldehyde and a methylenizing agent is in the range of 0.5:1.
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) | 1988-04-29 | 1988-10-29 | 1989-04-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-04-29 | 1992-10-29 | 1993-04-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-04-29 | 1996-10-29 | 1997-04-30 | $7700.00 | Window Closed / Lapsed |