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US4074008A Expired / Lapsed US ⏱️ 0.0 years remaining

Epoxide resins

Assignee: Novartis Corp
•
Filing: 1976-08-03
•
Granted: 1978-02-14
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Expires: 1996-08-03
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Abstract

Abstract Epoxide resins, which polymerize on exposure to actinic radiation, have, per average molecule, at least two photopolymerizable groups and also at least two 1,2-epoxide groups, one or more such epoxide groups being contained in units of formula ##STR1## Photopolymerizable epoxide resins are commonly prepared by introduction of photopolymerizable groups into a molecule of an epoxide resin by reaction with some of the epoxide groups: the modified resin, having a low epoxide group content, usually exhibits poorer adhesion and lower glass transition temperature than would otherwise be the case. In the new resins, secondary hydroxyl groups generated on introduction of the photopolymerizable groups have been converted into glycidyl ether groups, thus they have a higher epoxide content.

Inventors

  • 👤 George E. Green

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-24 15:55
CPC Classifications
H; H05; H05K; H05K3/00; H05K3/46; H05K3/4611; H05K3/4626; C; C08; C08G; C08G59/00; C08G59/02; C08G59/04; H05K2201/00; H05K2201/01; H05K2201/0183; H05K2201/0195; H05K2203/00; H05K2203/07; H05K2203/0779; H05K2203/0783; H05K3/02; H05K3/06; H05K3/061; H05K3/064; Y; Y10; Y10S; Y10S522/00; Y10S522/904; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31511; Y10T428/31529

Claims Analysis

Total Claims: 36
Claim 1
Independent Claim 38 words
Epoxide resins which polymerise on exposure to actinic radiation, having, per average molecule, at least two photopolymerisable groups and also at least two 1,2-epoxide groups, one or more such epoxide groups being contained in units of formula ##STR21##
Claim 2
Dependent Claim 38 words
Epoxide resins which polymerise on exposure to actinic radiation, having, per average molecule, at least two photopolymerisable groups and also at least two 1,2-epoxide groups, one or more such epoxide groups being contained in units of formula ##STR21##
Claim 3
Dependent Claim 16 words
Epoxide resins according to claim 1, having an average molecular weight of from 500 to 10,000.
Claim 4
Dependent Claim 30 words
Epoxide resins according to claim 1, in which the units of formula I are linked to carbon atoms in the remainder of the molecule through oxygen, nitrogen, or sulfur atoms.
Claim 5
Dependent Claim 59 words
Epoxide resins according to claim 1, in which the photopolymerisable groups are of the formula ##STR22## where R represents a hydrogen atom or an aliphatic, aromatic, araliphatic, or heterocyclic group of 1 to 12 carbon atoms, and R 1 represents a hydrogen, chlorine, or bromine atom, an alkyl group of 1 to 4 carbon atoms, or a cyano group.
Claim 6
Dependent Claim 24 words
Epoxide resins according to claim 4, in which the group R contains ethylenic unsaturation or aromaticity in conjugation with the indicated ethylenic double bond.
Claim 7
Dependent Claim 22 words
Epoxide resins according to claim 4, in which the group of formula II are directly attached to oxygen atoms or nitrogen atoms.
Claim 8
Dependent Claim 121 words
Epoxide resins according to claim 6, which are of the formula ##STR23## where R represents a hydrogen atom or an aliphatic, aromatic, araliphatic or heterocyclic group of 1 to 13 carbon atoms, R 1 represents a hydrogen, chlorine, or bromine atom, an alkyl group of 1 to 4 carbon atoms, or a cyano group, R 2 represents the residue of a polyglycidyl compound after removal of glycidyl groups directly attached to oxygen, nitrogen, or sulfur atoms, the said residue being linked through oxygen, nitrogen, or sulfur atoms thereof to the indicated groups, a represents an integer of at least 2, and X represents a hydrogen atom or a glycidyl group, such that at least one group X is a glycidyl group.
Claim 9
Dependent Claim 23 words
Epoxide resins according to claim 7, in which the group R 2 is linked to the other indicated groups through ether oxygen atoms.
Claim 10
Dependent Claim 23 words
Epoxide resins according to claim 7, in which the group R 2 is linked to the other indicated groups through amidic nitrogen atoms.
Claim 11
Dependent Claim 18 words
Epoxide resins according to claim 9, in which the amidic nitrogen atoms are those of a cyclic urea.
Claim 12
Dependent Claim 233 words
Epoxide resins according to claim 1, in which the photopolymerisable groups are of the formula ##STR24## the units of formulae XII to XV being linked by one indicated free valence through an oxygen atom to a carbon atom and by the other free valence either through another oxygen atom to another carbon atom or direct to a hydrogen atom, where each R 3 is a halogen atom or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkoxy, cycloalkoxy, alkenoxy, cycloalkenoxy, carbalkoxy, carbocycloalkoxy, carbalkenoxy, or carbocycloalkenoxy group, such organic groups containing up to 9 carbon atoms, a nitro group, or a carboxyl, sulfonic, or phosphoric acid group in the form of a salt, b represents zero or an integer of 1 to 4, c represents zero or an integer of 1 to 5, d represents zero or an integer of 1 to 3, Y represents a chain of carbon atoms containing in that chain a grouping of formula ##STR25## R 4 and R 5 are each individually a hydrogen atom, an alkyl group, or an aryl group, or R 4 and R 5 conjointly denote a polymethylene chain of 2 to 4 methylene groups, R 6 and R 7 are each a hydrogen atom, an alkyl group, or an aryl group, e and f are each zero, 1, or 2, with the proviso that they are not both zero, and Z is an oxygen or sulfur atom.
Claim 13
Dependent Claim 74 words
Epoxide resins according to claim 11, which are of the formula ##STR26## where A denotes a group of any of formula XII to XV in claim 11, X represents a hydrogen atom or a glycidyl group such that at least one group X is a glycidyl group, and g is a positive integer of average value such that the average molecular weight of the epoxide resin is at least 500 and at most 10,000.
Claim 14
Dependent Claim 124 words
Epoxide resins according to claim 11, which are of the formula ##STR27## where R 2 represents the residue of a polyglycidyl compound after removal of glycidyl groups directly attached to oxygen, nitrogen, or sulfur atoms, the said residue being linked through oxygen, nitrogen, or sulfur atoms thereof to the indicated groups, A denotes a group of any of formulae XII to XV in claim 11, X represents a hydrogen atom or a glycidyl group such that at least one group X is a glycidyl group, h is zero or a positive integer, and j and k are each an integer of one or more, h, j, and k being such that the average molecular weight of the epoxide resin is from 5000 to 10,000.
Claim 15
Dependent Claim 131 words
Epoxide resins according to claim 11, which are of the formula ##STR28## where R represents a hydrogen atom or an aliphatic, aromatic, araliphatic, or heterocyclic group of 1 to 13 carbon atoms, R 1 represents a hydrogen, chlorine, or bromine atom, an alkyl group of 1 to 4 carbon atoms, or a cyano group, A denotes any group of formulae XII to XV in claim 11, g is a positive integer of average value such that the average molecular weight of the epoxide resin is at least 500 and at most 10,000 h is zero or a positive integer, and j and k are each an integer of one or more, h, j and k being such that the average molecular weight of the epoxide resin is from 500 to 10,000.
Claim 16
Dependent Claim 16 words
Epoxide resins according to claim 1, in which the photopolymerisable groups are of the formula ##STR29##
Claim 17
Dependent Claim 80 words
Epoxide resins according to claim 15, which are of the formula ##STR30## where X represents a hydrogen atom or a glycidyl group, such that at least one group X is a glycidyl group, a represents an integer of at least 2, and R 2 represents the residue of a polyglycidyl compound after removal of glycidyl groups directly attached to oxygen, nitrogen, or sulfur atoms, the said residue being linked through oxygen, nitrogen or sulfur atoms thereof to the indicated groups.
Claim 18
Dependent Claim 22 words
A plate, sensitive to actinic radiation, comprising a support coated with a layer of an epoxide resin as claimed in claim 1.
Claim 19
Dependent Claim 20 words
A plate as claimed in claim 17, in which a sensitiser is present in the layer of the epoxide resin.
Claim 20
Dependent Claim 27 words
A plate as claimed in claim 18, in which the photosensitiser is a bis(dialkylamino)benzophenone, a benzoyl phenyl carbinol, or an alkyl ether of a benzoyl phenyl carbinol.
Claim 21
Dependent Claim 25 words
A plate as claimed in claim 17, in which a heat-curing agent for the epoxide resin is present in the layer of the epoxide resin.
Claim 22
Dependent Claim 40 words
A plate as claimed in claim 20, in which the curing agent is an aromatic polyamine, an acid anhydride, a polythiol, dicyandiamide, a complex of a tertiary amine with boron trifluoride or boron trichloride or is a boron difluoride chelate.
Claim 23
Dependent Claim 19 words
A process of photopolymerising an epoxide resin as claimed in claim 1 which comprises subjecting it to actinic radiation.
Claim 24
Dependent Claim 17 words
The process of claim 22, in which the radiation has a wavelength of 200 to 600 nm.
Claim 25
Dependent Claim 41 words
The process of claim 22, in which a plate coated with a layer of epoxide resin is subjected to actinic radiation, optionally imagewise as through a negative, and any unpolymerised portions of the resin are removed by means of a solvent.
Claim 26
Dependent Claim 21 words
The process of claim 22, in which the epoxide resin is subjected to actinic radiation in the presence of a photosensitiser.
Claim 27
Dependent Claim 25 words
The process of claim 25, in which the photosensitiser is a bis(dialkylamino)benzophenone, a benzoyl phenyl carbinol, or an alkyl ether of a benzoyl phenyl carbinol.
Claim 28
Dependent Claim 24 words
The process of claim 22, in which the epoxide resin is, after photopolymerisation, crosslinked through reaction of its epoxide groups with a curing agent.
Claim 29
Dependent Claim 25 words
The process of claim 27, in which crosslinking of the photopolymerised resin is carried out at a temperature in the range 100° to 200° C.
Claim 30
Dependent Claim 38 words
The process of claim 27, in which the curing agent is an aromatic amine, an acid anhydride, a polythiol, dicyandiamide, a complex of a tertiary amine with boron trifluoride or boron trichloride, or is a boron difluoride chelate.
Claim 31
Dependent Claim 94 words
A process for preparation of multilayer printed circuits which comprises coating a layer of metal with a layer of photopolymerisable epoxide resin as claimed in claim 1, exposing the resin to actinic radiation imagewise through a negative, removing the unpolymerised portions of the resin by means of a solvent, etching the exposed metal, stacking the plates alternately with insulating layers, an effective amount of a heat-curing agent for epoxide resins being contained either in the layer of the said photopolymerisable epoxide resin or in the said insulating layers, and crosslinking the resin by heat.
Claim 32
Dependent Claim 22 words
The process of claim 30, in which the photopolymerisable epoxide resin is exposed to actinic radiation in the presence of a photosensitiser.
Claim 33
Dependent Claim 25 words
The process of claim 31 in which the photosensitiser is a bis(dialkylamino)benzophenone, a benzoyl phenyl carbinol, or an alkyl ether of a benzoyl phenyl carbinol.
Claim 34
Dependent Claim 22 words
The process of claim 30, in which the photopolymerised resin is crosslinked at a temperature in the range 100° to 200° C.
Claim 35
Dependent Claim 41 words
The process of claim 30, in which the photopolymerised resin is crosslinked by means of an aromatic polyamine, an acid anhydride, a polythiol, dicyandiamide, a complex of a tertiary amine with boron trifluoride or boron trichloride or a boron difluoride chelate.
Claim 36
Dependent Claim 9 words
Printed circuits made by the process of claim 30.

References Cited (Backward Citations)

US3885060A Cited
US3956043A Cited
US3996121A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-02-13 1981-08-15 1982-02-14 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-02-13 1985-08-15 1986-02-14 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-02-13 1989-08-15 1990-02-14 $7700.00 Window Closed / Lapsed

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