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Patent US4252593A successfully refreshed from Google Patents.
US4252593A
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US
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Method of preparing reinforced composites
Assignee: BASF Corp
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Filing: 1978-05-22
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Granted: 1981-02-24
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Expires: 1998-05-22
Abstract
Abstract A method for the preparation of prepregs comprises (i) exposing to actinic radiation a layer of a liquid composition containing an epoxide resin, a photopolymerizable compound and a heat-activated curing agent for epoxide resins until the said composition solidifies to form an essentially solid continuous film due to photopolymerization of the said photopolymerizable compound while the 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. Preferably the liquid composition also contains a dual-functional substance which has in the same molecule both an epoxide group and a dissimilar group through which the substance can be photopolymerized. The prepreg, optionally after shaping and/or heating, is heated to cure the epoxide resin and, if used, the photopolymerized dual-functional substance.
Inventors
- 👤 George E. Green
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 12:50
CPC Classifications
C; C08; C08F; C08F283/00; C08F283/10; C08J; C08J5/00; C08J5/24; C08J5/241; C08J5/243; C08J5/244; C08J5/248; C08J5/249; C08J2363/00; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31511; Y10T442/00; Y10T442/20; Y10T442/2926; Y10T442/2984; Y10T442/2992
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
115 words
A method for the preparation of prepregs which comprises (i) exposing to actinic radiation a layer of a liquid composition containing (a) an epoxide resin (b) a photopolymerisable compound, the molar ratio of a:b being from 10:1 to 1:10, and (c) 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 said photopolymerisable compound while the 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
115 words
A method for the preparation of prepregs which comprises (i) exposing to actinic radiation a layer of a liquid composition containing (a) an epoxide resin (b) a photopolymerisable compound, the molar ratio of a:b being from 10:1 to 1:10, and (c) 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 said photopolymerisable compound while the 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
29 words
The method of claim 1, in which the epoxide resin, the photopolymerisable compound, and the said curing agent together constitute from 20 to 80% by weight of the prepreg.
Claim 4
Dependent Claim
73 words
The method of claim 1, in which the epoxide resin contains at least one group of formula ##STR23## 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 5
Dependent Claim
17 words
The method of claim 1, in which the photopolymerisable compound is photopolymerised through a free-radical chain reaction.
Claim 6
Dependent Claim
28 words
The method of claim 1, in which the photopolymerisable compound is photopolymerised by reaction of an excited molecule of the monomer with an unexcited molecule of the monomer.
Claim 7
Dependent Claim
22 words
The method of claim 4, in which the photopolymerisable compound has one ethylenic linkage, or, providing they are unconjugated, more than one.
Claim 8
Dependent Claim
50 words
The method of claim 6, in which the photopolymerisable compound is an acrylic ester containing at least one group of formula CH.sub.2 ═C(R.sup.3)COO-- or ##STR24## or CH.sub.2 ═C(R.sup.3)CONHCH(OH)CH.sub.2 COO-- where R 3 is a hydrogen, chlorine, or bromine atom, or an alkyl hydrocarbon group of 1 to 4 carbon atoms.
Claim 9
Dependent Claim
54 words
The method of claim 5, in which the photopolymerisable compound has at least two groups which are azido, coumarin, stilbene, maleimide, pyridinone, chalcone, propenone, pentadienone, or acrylic acid groups which are substituted in their 3- position by groups having ethylenic unsaturation or aromaticity in conjugation with the ethylenic double bond of the acrylic group.
Claim 10
Dependent Claim
37 words
The method of claim 8, in which the photopolymerisable compound contains at least two groups of the formula N.sub.3 Ar-- where Ar denotes a divalent mononuclear or dinuclear aromatic radical containing from 6 to 14 carbon atoms.
Claim 11
Dependent Claim
37 words
The method of claim 8, in which the photopolymerisable compound contains at least two groups of the formula ##STR25## where R 4 is an oxygen atom, a carbonyloxy group (--COO--), a sulfonyl group, or a sulfonyloxy group.
Claim 12
Dependent Claim
72 words
The method of claim 8, in which the photopolymerisable compound contains at least two groups of the formula ##STR26## where R 5 is the residue, containing not more than 8 carbon atoms in all, of a five or six-membered nitrogen-containing heterocyclic ring, fused to a benzene or naphthalene nucleus, and linked through a carbon atom of the said heterocyclic ring adjacent to a nitrogen hetero atom thereof to the indicated benzene nucleus.
Claim 13
Dependent Claim
40 words
The method of claim 8, in which the photopolymerisable compound contains at least two groups of the formula ##STR27## where each R 6 is an alkyl group of 1 to 4 carbon atoms, a chlorine atom, or a phenyl group.
Claim 14
Dependent Claim
45 words
The method of claim 8, in which the photopolymerisable compound contains at least two groups of the formula ##STR28## where R 7 is an aliphatic or cycloaliphatic radical of 1 to 8 carbon atoms, and a is zero or an integer of 1 to 4.
Claim 15
Dependent Claim
197 words
The method of claim 8, in which the photopolymerisable compound contains at least two groups of the formula ##STR29## where each R 8 is a halogen atom, or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkoxy, cycloalkoxy, alkenoxy, cycloalkenoxy, carbalkoxy, carbocycloalkoxy, carbalkenoxy, or carbocycloalkenoxy group, such organic groups containing 1 to 9 carbon atoms, or is a nitro group, or a carboxyl, sulfonic, or phosphoric acid group in the form of a salt, a is zero or an integer of 1 to 4, R 9 represents a valence bond or a hydrogen atom, Y represents a chain of carbon atoms containing in that chain a grouping of formula ##STR30## R 10 and R 11 each each individually a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, or an aryl group, or R 10 and R 11 conjointly denote a polymethylene chain of 2 to 4 methylene groups, R 12 and R 13 are each a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, or an aryl group, b and c are each zero, 1, or 2, with the proviso that they are not both zero, and Z is an oxygen or sulfur atom.
Claim 16
Dependent Claim
68 words
The method of claim 8, in which the photopolymerisable compound contains at least two groups of the formula R.sup.14 CH═C(R.sup.3)COO-- where R 14 is an aliphatic or mononuclear aromatic, araliphatic, or heterocyclyl group which has ethylenic unsaturation or aromaticity in conjugation with the ethylenic double bond shown, and R 3 is a hydrogen, chlorine, or bromine atom, or an alkyl hydrocarbon group of 1 to 4 carbon atoms.
Claim 17
Dependent Claim
39 words
The method of claim 1, in which the heat-activated curing agent is a polycarboxylic acid anhydride, dicyandiamide, a complex of an amine with boron trifluoride or boron trichloride, a latent boron difluoride chelate, an aromatic polyamine, or an imidazole.
Claim 18
Dependent Claim
16 words
The method of claim 1, in which the photopolymerisable compound does not contain a 1,2-epoxide group.
Claim 19
Dependent Claim
46 words
The method of claim 1, in which the fibrous reinforcing material is also impregnated with a dual-functional substance having in the same molecule both at least one 1,2-epoxide group and at least one dissimilar group through which the substance is polymerised by means of actinic radiation.
Claim 20
Dependent Claim
120 words
The method of claim 18, in which the dual-functional substance contains in the same molecule at least one group of formula ##STR31## directly attached to an atom of oxygen, nitrogen, or sulfur, and at least one group of formula ##STR32## directly attached to an atom of oxygen, nitrogen, or sulfur, where L is the monovalent photopolymerisable residue of a substance after removal of a hydrogen atom attached directly to an oxygen, nitrogen, or sulfur atom, and 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 21
Dependent Claim
23 words
The method of claim 1, in which the components of the said film are caused to flow about the fibers by applying heat.
Claim 22
Dependent Claim
23 words
The method of claim 1, in which the components of the said film are caused to flow about the fibers by applying pressure.
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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 |