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Patent · US4559398A · A · US

Curable epoxy resins

(11) Publication number
US4559398A
(21) Application number
06/636,236
(22) Filing date
1984-07-31
(30) Priority date
1983-08-02
(43) Publication date
1985-12-17
(45) Date of grant
1985-12-17
(51) IPC
C07D 233/60; C07D 521/00; C08G 59/68; C08K 5/3445; C08L 63/00
(52) CPC
  • C07D Heterocyclic compounds: 231/12, 233/56, 249/08
  • C08G Macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds: 59/686
  • C08K Use of inorganic or non-macromolecular organic substances as compounding ingredients: 5/3445
(73) Assignee
BASF SE
(72) Inventors
Helmut Tesch; Andreas Henne; Manfred Heym; Herbert Stutz
(54) Title
Curable epoxy resins
(57) Abstract

A curable composition consisting of A. 100 parts by weight of an epoxy resin, B. from 4 to 100 parts by weight of a conventional curing agent for epoxy resins, and C. from 0.1 to 5 parts by weight of an N-acylimidazole which possesses an aromatic acyl component which is substituted at the two positions ortho to the carbonyl group can be used to produce moldings, coatings, finishes, adhesives and composite fiber materials.

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Claims (7)

  1. A curable resin composition containing A. 100 parts by weight of an epoxy resin, B. from 4 to 100 parts by weight of a conventional curing agent for epoxy resins, and C. from 0.1 to 5 parts by weight of a N-acylimidazole as an accelerator, wherein component C is an N-acylimidazole of the formula ##STR1## where R 1, R 2 and R 3 can be identical or different and are each hydrogen, branched or straight-chain alkyl of 1 to 17 carbon atoms, chlorine, or phenyl which is unsubstituted or substituted by alkyl, alkoxy or chlorine, or are each haloalkyl, hydroxyalkyl, a carboxylic ester group or a carboxamide group, R 4 and R 5 can be identical or different and are each a branched or straight-chain alkyl, alkoxy or alkylthio group of 1 to 4 carbon atoms, R 6 is hydrogen, an alkoxy or alkylthio group of 1 to 6 carbon atoms, dialkylamino where alkyl is of 1 to 6 carbon atoms or branched or straight-chain alkyl of 1 to 12 carbon atoms, n is 1, 2 or 3 and R 7 is alkyl of 1 to 4 carbon atoms.
  2. A curable composition as claimed in claim 1, which contains A. 100 parts by weight of bisphenol A diglycidyl ether as an epoxy resin B. from 4 to 10 parts by weight of dicyanodiamide as a curing agent for the epoxy resin, and C. from 0.2 to 2 parts by weight of an N-acylimidazole.
  3. A process for the production of a molding by introducing a curable composition as claimed in claim 1 into a mold, and carrying out curing at from 50° to 300° C.
  4. A process for the production of a finish, a coating or an adhesive by applying a curable composition as claimed in claim 1 onto a substrate, and carrying out curing at from 50° to 300° C.
  5. A process for the production of a composite fiber material by impregnating from 30 to 70 vol. % of reinforcing fibers with from 70 to 30 vol. % of a curable composition as claimed in claim 1, and carrying out curing at from 50° to 300° C.
  6. A curable resin composition as set forth in claim 1, wherein R 4 and R 5 are each alkyl of 1 to 4 carbon atoms.
  7. A curable resin composition as set forth in claim 1, wherein R 4 and R 5 are each methyl.

Description

The present invention relates to epoxy resins which contain a substituted N-acylimidazole as an accelerator, in combination with a conventional curing agent.

It has been disclosed, for example in GB-A-1,050,679, that imidazoles react very rapidly with epoxy resins at elevated temperatures to give moldings possessing good physical properties. The imidazoles initiate anionic polymerization of the epoxy resins, with the result that a three-dimensional network comprising polyether structures is formed.

It has also been disclosed, for example in U.S. Pat. No. 3,329,652, that small amounts of imidazoles can act as curing agents and accelerate the reaction of epoxy resins with polycarboxylic anhydrides.

In both cases, the mixtures have the disadvantage that they have only a short shelf life at room temperature and at moderately elevated temperatures.

It is an object of the present invention to provide a curable resin composition based on epoxy resins, which has a relatively long shelf life at room temperature and moderately elevated temperatures, and undergoes rapid curing, giving moldings with good mechanical properties, only when the temperature is increased greatly.

We have found that this object is achieved if an N-acylimidazole which possesses an aromatic acyl component which is substituted at the two positions ortho to the carbonyl group is used as an accelerator for epoxy resins containing conventional curing agents.

U.S. Pat. No.

Citations (3)

  • GB1050679A
  • US3329652A
  • US4436892A
Record as JSON
{
  "publication_number": "US4559398A",
  "country": "US",
  "kind": "A",
  "title": "Curable epoxy resins",
  "abstract": "A curable composition consisting of A. 100 parts by weight of an epoxy resin, B. from 4 to 100 parts by weight of a conventional curing agent for epoxy resins, and C. from 0.1 to 5 parts by weight of an N-acylimidazole which possesses an aromatic acyl component which is substituted at the two positions ortho to the carbonyl group can be used to produce moldings, coatings, finishes, adhesives and composite fiber materials.",
  "claims": [
    "1. A curable resin composition containing A. 100 parts by weight of an epoxy resin, B. from 4 to 100 parts by weight of a conventional curing agent for epoxy resins, and C. from 0.1 to 5 parts by weight of a N-acylimidazole as an accelerator, wherein component C is an N-acylimidazole of the formula ##STR1## where R 1, R 2 and R 3 can be identical or different and are each hydrogen, branched or straight-chain alkyl of 1 to 17 carbon atoms, chlorine, or phenyl which is unsubstituted or substituted by alkyl, alkoxy or chlorine, or are each haloalkyl, hydroxyalkyl, a carboxylic ester group or a carboxamide group, R 4 and R 5 can be identical or different and are each a branched or straight-chain alkyl, alkoxy or alkylthio group of 1 to 4 carbon atoms, R 6 is hydrogen, an alkoxy or alkylthio group of 1 to 6 carbon atoms, dialkylamino where alkyl is of 1 to 6 carbon atoms or branched or straight-chain alkyl of 1 to 12 carbon atoms, n is 1, 2 or 3 and R 7 is alkyl of 1 to 4 carbon atoms.",
    "2. A curable composition as claimed in claim 1, which contains A. 100 parts by weight of bisphenol A diglycidyl ether as an epoxy resin B. from 4 to 10 parts by weight of dicyanodiamide as a curing agent for the epoxy resin, and C. from 0.2 to 2 parts by weight of an N-acylimidazole.",
    "3. A process for the production of a molding by introducing a curable composition as claimed in claim 1 into a mold, and carrying out curing at from 50° to 300° C.",
    "4. A process for the production of a finish, a coating or an adhesive by applying a curable composition as claimed in claim 1 onto a substrate, and carrying out curing at from 50° to 300° C.",
    "5. A process for the production of a composite fiber material by impregnating from 30 to 70 vol. % of reinforcing fibers with from 70 to 30 vol. % of a curable composition as claimed in claim 1, and carrying out curing at from 50° to 300° C.",
    "6. A curable resin composition as set forth in claim 1, wherein R 4 and R 5 are each alkyl of 1 to 4 carbon atoms.",
    "7. A curable resin composition as set forth in claim 1, wherein R 4 and R 5 are each methyl."
  ],
  "description_excerpt": "The present invention relates to epoxy resins which contain a substituted N-acylimidazole as an accelerator, in combination with a conventional curing agent.\n\nIt has been disclosed, for example in GB-A-1,050,679, that imidazoles react very rapidly with epoxy resins at elevated temperatures to give moldings possessing good physical properties. The imidazoles initiate anionic polymerization of the epoxy resins, with the result that a three-dimensional network comprising polyether structures is formed.\n\nIt has also been disclosed, for example in U.S. Pat. No. 3,329,652, that small amounts of imidazoles can act as curing agents and accelerate the reaction of epoxy resins with polycarboxylic anhydrides.\n\nIn both cases, the mixtures have the disadvantage that they have only a short shelf life at room temperature and at moderately elevated temperatures.\n\nIt is an object of the present invention to provide a curable resin composition based on epoxy resins, which has a relatively long shelf life at room temperature and moderately elevated temperatures, and undergoes rapid curing, giving moldings with good mechanical properties, only when the temperature is increased greatly.\n\nWe have found that this object is achieved if an N-acylimidazole which possesses an aromatic acyl component which is substituted at the two positions ortho to the carbonyl group is used as an accelerator for epoxy resins containing conventional curing agents.\n\nU.S. Pat. No.",
  "cpc": [
    "C07D 231/12",
    "C07D 233/56",
    "C07D 249/08",
    "C08G 59/686",
    "C08K 5/3445"
  ],
  "ipc": [
    "C07D 233/60",
    "C07D 521/00",
    "C08G 59/68",
    "C08K 5/3445",
    "C08L 63/00"
  ],
  "assignees": [
    "BASF SE"
  ],
  "inventors": [
    "Helmut Tesch",
    "Andreas Henne",
    "Manfred Heym",
    "Herbert Stutz"
  ],
  "filing_date": "1984-07-31",
  "publication_date": "1985-12-17",
  "grant_date": "1985-12-17",
  "priority_date": "1983-08-02",
  "application_number": "US-63623684-A",
  "family_id": "6205542",
  "cited_by_count": 11,
  "citations": [
    "GB1050679A",
    "US3329652A",
    "US4436892A"
  ]
}

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