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US4252592A Expired / Lapsed US ⏱️ 0.0 years remaining

Method of making epoxide resin-impregnated composites

Assignee: Novartis Corp
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Filing: 1978-06-26
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Granted: 1981-02-24
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Expires: 1998-06-26
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Abstract

Abstract A layer of a liquid composition containing an epoxide resin as the sole photopolymerizable component, a heat-activated curing agent for epoxide resins, and preferably a photopolymerization catalyst, is exposed to actinic radiation until the layer solidifies to form an essentially solid, continuous film due to photopolymerization of the epoxide resin through epoxide groups, the resin remaining, however, still thermosettable by virtue of residual epoxide groups. The film so formed is contacted with fibrous reinforcing material and caused to flow about the fibers, suitably by applying heat and pressure, to form a prepreg. When desired, e.g., after the prepreg has been formed into some desired configuration or layers of prepreg have been stacked, the assembly may be cured by further heating.

Inventors

  • 👤 George E. Green

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 23:43
CPC Classifications
B; B32; B32B; B32B5/00; B32B5/22; B32B5/24; B32B5/26; C; C08; C08G; C08G59/00; C08G59/18; C08G59/68; C08J; C08J3/00; C08J3/28; C08J5/00; C08J5/24; C08J5/248; C08J5/249; C08K; C08K3/00; C08K3/02; C08K3/08; C08K3/18; C08K3/24; C08K3/34; C08K3/38; C08K3/40; C08K7/00; C08K7/02; C08L; C08L63/00; C08L77/00; B32B2262/00; B32B2262/02; B32B2262/0261; B32B2305/00; B32B2305/07; B32B2305/076; C08J2363/00

Claims Analysis

Total Claims: 21
Claim 1
Independent Claim 108 words
A method for the preparation of composite structures which comprises (i) exposing to actinic radiation a layer of a liquid composition containing an epoxide resin as the sole photopolymerisable component and a heat-activated curing agent for epoxide resins until the said composition solidifies to form an essentially solid continuous film due to photopolymerisation of the epoxide resin through epoxide groups thereof but which epoxide resin remains substantially in the thermosettable state, and (ii) bringing together the film so formed and fibrous reinforcing material under conditions such that the said film flows about the fibers and the components of the said film and the fibers form a coherent structure.
Claim 2
Independent Claim 108 words
A method for the preparation of composite structures which comprises (i) exposing to actinic radiation a layer of a liquid composition containing an epoxide resin as the sole photopolymerisable component and a heat-activated curing agent for epoxide resins until the said composition solidifies to form an essentially solid continuous film due to photopolymerisation of the epoxide resin through epoxide groups thereof but which epoxide resin remains substantially in the thermosettable state, and (ii) bringing together the film so formed and fibrous reinforcing material under conditions such that the said film flows about the fibers and the components of the said film and the fibers form a coherent structure.
Claim 3
Dependent Claim 73 words
The method of claim 1, in which the epoxide resin contains at least one group of formula ##STR7## directly attached to an atom of oxygen, nitrogen, or sulfur, where either R and R 2 each represent a hydrogen atom, in which case R 1 denotes a hydrogen atom or a methyl group, or R and R 2 together represent --CH 2 CH 2 --, in which case R 1 denotes a hydrogen atom.
Claim 4
Dependent Claim 43 words
The method of claim 1, in which the epoxide resin is a diglycidyl ether of a dihydric phenol or of a dihydric alcohol, an N,N'-diglycidyl derivative of a hydantoin, an advanced such diglycidyl ether, or an advanced such N,N'-diglycidyl derivative of a hydantoin.
Claim 5
Dependent Claim 38 words
The method of claim 1, in which the said heat-activated curing agent is a polycarboxylic acid anhydride, dicyandiamide, a complex of boron trifluoride or of boron trichloride, a latent boron difluoride chelate, an imidazole, or an aromatic polyamine.
Claim 6
Dependent Claim 29 words
The method of claim 1, in which the said heat-activated curing agent comprises from 0.5 to 20 parts by weight per 100 parts by weight of the epoxide resin.
Claim 7
Dependent Claim 15 words
The method of claim 1, in which the said composition also contains a photopolymerisation catalyst.
Claim 8
Dependent Claim 27 words
The method of claim 6, in which the photopolymerisation catalyst comprises from 0.1 to 20 parts by weight per 100 parts by weight of the epoxide resin.
Claim 9
Dependent Claim 25 words
The method of claim 6, in which the photopolymerisation catalyst is an aromatic 'onium salt which liberates a Lewis acid on exposure to actinic radiation.
Claim 10
Dependent Claim 14 words
The method of claim 6, in which the photopolymerisation catalyst is a diazonium salt.
Claim 11
Dependent Claim 186 words
The method of claim 6, in which the photopolymerisation catalyst is of the formula ##STR8## where R 3 , R 4 , and R 5 independently each represent a hydrogen or halogen atom or an alkyl, alkoxy, aryl, nitro, or sulfonyl group, Q represent an oxygen or sulfur atom or an imino group, R 6 and R 7 individually represent an alkyl group or, together with the nitrogen atom to which they are attached, represent a saturated or unsaturated 5- or 6-membered mononuclear heterocyclic residue, a saturated or unsaturated 5- or 6-membered mononuclear heterocylic residue also containing in the ring an oxygen atom, a saturated or unsaturated 5- or 6-membered mononuclear heterocyclic residue also containing in the ring a sulfur atom, or a saturated or unsaturated mononuclear heterocyclic residue containing in the ring a second nitrogen atom, R 8 represent a halogen atom or a nitro, N-morpholino, alkyl, alkoxy, aryl, amino, arylamino, alkylamino, or arylmercapto group, n is the oxidation state of M, m is the number of diazonium groups in the diazonium salt, and MX n+m represents hexachlorostannate, tetrachloroferrate, hexafluorophosphate, hexafluoroarsenate, hexachloroantimonate, hexafluoroantimonate, or pentachlorobismuthate.
Claim 12
Dependent Claim 22 words
The method of claim 6, in which the photopolymerisation catalyst is an aromatic ammonium, arsonium, phosphonium, sulfonium, or selenonium tetrafluoroborate or hexafluorophosphate.
Claim 13
Dependent Claim 15 words
The method of claim 6, in which the photopolymerisation catalyst is an aromatic halogenonium salt.
Claim 14
Dependent Claim 26 words
The method of claim 6, in which the photopolymerisation catalyst is an aromatic iodonium tetrafluoroborate, hexafluorophosphate, hexafluoroantimonate, hexachlorantimonate, tetrachlorostannate, tetrachloroferrate, pentachlorobismuthate, hydrogen sulfate, nitrate, or hexafluoroarsenate.
Claim 15
Dependent Claim 20 words
The method of claim 6, in which the photopolymerisation catalyst is a sulfonium or iodonium salt of a sulfonic acid.
Claim 16
Dependent Claim 180 words
The method of claim 6, in which the photopolymerisation catalyst is a sulfonium salt of the formula ##STR9## or an iodonium salt of the formula ##STR10## where R 9 is a monovalent aromatic organic group, R 10 is a monovalent alkyl, cycloalkyl, or substituted alkyl group, R 11 is an aliphatic or aromatic residue forming, with the indicated sulfur atom, a heterocyclic structure which may contain a condensed ring, R 12 is a divalent aromatic residue, a is zero or an integer of 1 to 3, b is zero, 1, or 2, c is zero or 1, such that the sum of a+b+c is 3, d is zero or 2, e is zero or 1, such that one, but not both, of d and e is zero, and R 13 is a fluorine atom, an aromatic hydrocarbon residue of 6 to 13 carbon atoms, an aromatic residue consisting of halogen atoms, hydrogen atoms, and from 6 to 13 carbon atoms, an alkyl group of 1 to 8 carbon atoms, or a halogen-substituted alkyl group of 1 to 8 carbon atoms.
Claim 17
Dependent Claim 13 words
The method of claim 6, in which the photopolymerisation catalyst is an o-alkylnitrobenzene.
Claim 18
Dependent Claim 61 words
The method of claim 6, in which the photopolymerisation catalyst is of the formula ##STR11## where R 14 and R 15 each represent a hydrogen atom or an alkyl, aryl, carbalkoxy, pyridyl, carbazolyl, N-oxidopyridyl, nitroalkyl, nitroaryl, alkaryl, aralkyl, haloalkyl, or haloaryl group, and R 16 represents a hydrogen atom or an alkyl, aryl, nitroalkyl, nitroaryl, alkaryl, aralkyl, haloalkyl, or haloaryl group.
Claim 19
Dependent Claim 67 words
The method of claim 5, in which the photopolymerisation catalyst is a mixture of an organohalogen compound containing alkyl, aryl, alkaryl, aralkyl, alkoxy, or aryloxy groups and an organometalloidal compound of formula (R.sup.17).sub.3 E where each R 17 represents a hydrogen atom or hydrocarbon group such that at least one group R 17 is a hydrocarbon group and E represents a phosphorus, antimony, arsenic, or bismuth atom.
Claim 20
Dependent Claim 25 words
The method of claim 6, in which the photopolymerisation catalyst is a chromate or dichromate of an alkali metal, an alkaline earth metal, or ammonium.
Claim 21
Dependent Claim 27 words
The method of claim 6, in which the photopolymerisation catalyst is a polyhalogenated organic compound that yields a halogen-free radical at a relatively low bond dissociation energy.

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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) 1984-02-24 1984-08-25 1985-02-24 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-02-24 1988-08-25 1989-02-24 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-02-24 1992-08-25 1993-02-24 $7700.00 Window Closed / Lapsed

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