Patents by Inventor Edward Irving

Edward Irving has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 4572890
    Abstract: A layer of a liquid composition containing (A) a compound containing at least one heat-polymerizable, ethylenically-unsaturated group, (B) a photopolymerizable material, and (C) a thermally-activated free radical initiator for polymerization of (A), is heated to solidify the layer, and subsequently it is exposed to actinic radiation in a predetermined pattern and those parts of the layer that have not become photopolymerized are removed by treatment with a suitable solvent.An example of an unsaturated, heat polymerizable compound (A) is butanediol dimethacrylate. An example of a photopolymerizable material (B) is an epoxidized novolak of 2,2-bis(4-hydroxyphenyl)propane with triphenylsulfonium hexafluorophosphate. A typical thermally-activated, free radical initiator (C) is cumene hydroperoxide.The process is suitable for the manufacture of printing plates and printed circuits.
    Type: Grant
    Filed: May 1, 1984
    Date of Patent: February 25, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Jonathan W. Goodin, Edward Irving
  • Patent number: 4548895
    Abstract: A layer of a liquid composition containing (A) a heat-activated polymerizing agent for 1,2-epoxides, (B) a light-sensitive compound having in the same molecule at least one 1,2-epoxide group of formula ##STR1## and at least one unsaturated ester group of formulaCH.sub.2 .dbd.C(R.sup.1)COO-- IIwhere R.sup.1 =H, Cl, Br, or C.sub.1 -C.sub.4 alkyl, a mixture of (C) a compound containing at least one 1,2-epoxide group of formula I together with (D) a compound containing at least one unsaturated ester group of formula II, or a mixture of (B) with (C) and/or (D), is heated to solidify the layer, and subsequently it is exposed to actinic radiation in a predetermined pattern and those parts of the layer that have not become photopolymerized are removed by treatment with a suitable solvent.An example of a suitable polymerizing agent (A) is the complex of boron trifluoride with monoethylamine. An example of a light-sensitive compound (B) is glycidyl methacrylate.
    Type: Grant
    Filed: March 7, 1984
    Date of Patent: October 22, 1985
    Assignee: Ciba Geigy Corporation
    Inventors: Edward Irving, Terence J. Smith
  • Patent number: 4546067
    Abstract: A layer of a liquid composition containing(A) a heat-activated latent polymerizing agent for 1,2-epoxides with(B) a light-sensitive compound having in the same molecule at least one 1,2-epoxide group and at least one chalcone or cinnamate group, or with a mixture of(C) a compound containing at least one 1,2-epoxide group together with(D) a compound containing at least one chalcone or cinnamate group,is heated so that the layer solidifies due to thermal polymerization through the 1,2-epoxide group, remaining, however, photocrosslinkable. The solidified layer is exposed in a predetermined pattern to actinic radiation, the parts so exposed becoming photocrosslinked through the chalcone or cinnamate unit(s) and hence insoluble. An image is produced which can be developed by means of suitable solvents.An example of a suitable latent polymerizing agent (A) is boron trichloride-N-methylpiperidine complex, and a suitable light-sensitive compound (B) is 1-(p-(glycidyloxy)phenyl)-5-phenylpenta-1,4-dien-3-one.
    Type: Grant
    Filed: January 16, 1984
    Date of Patent: October 8, 1985
    Assignee: Ciba Geigy Corporation
    Inventors: Edward Irving, Terence J. Smith
  • Patent number: 4537725
    Abstract: New diaryliodosyl salts have the formula ##STR1## where R.sup.7 and R.sup.8, which may be the same or different, each represent a monovalent aromatic radical of from 6 to 22 carbon atoms,Z.sup.t- denotes a t-valent anion of formula MX.sub.n.sup.- or R.sup.9 SO.sub.3.sup.- or a t-valent anion of a halogen-free inorganic oxy acid,t is 1, 2 or 3,M represents an atom of a metal or metalloid,X denotes a halogen atom, preferably of fluorine or chlorine,n is 4, 5, or 6 and is one more than the valency of M, with the proviso that MX.sub.n.sup.- can represent SbOHF.sub.5.sup.-, andR.sup.9 denotes a monovalent aliphatic or aromatic group of 1 to 20 carbon atoms.These salts have utility as photocuring catalysts for cationically polymerizable materials such as epoxide resins and phenolic resins.
    Type: Grant
    Filed: September 9, 1983
    Date of Patent: August 27, 1985
    Assignee: Ciba-Geigy Corporation
    Inventor: Edward Irving
  • Patent number: 4518676
    Abstract: Photopolymerizable compositions contain a cationically polymerizable material, such as an epoxide resin, a phenoplast, or an aminoplast, and, as photoinitiator, a diaryliodosyl salt of formula ##STR1## where R.sup.9 and R.sup.10 are the same or different and each represents a monovalent aromatic radical,x represents 1, 2, or 3, andZ.sup.x- is an anion of a protic acid.Suitable diaryliodosyl salts of formula V include diphenyliodosyl hexafluorophosphate, hexafluoroantimonate, tetrafluoroborate, toluene-p-sulfonate, and chloride.The compositions may be used as surface coatings and adhesives, and in the preparation of reinforced composites and printed circuits.
    Type: Grant
    Filed: September 9, 1983
    Date of Patent: May 21, 1985
    Assignee: Ciba Geigy Corporation
    Inventor: Edward Irving
  • Patent number: 4500629
    Abstract: Images are prepared by a process in which a layer, supported on a substrate, of a liquid composition comprising(a) an anaerobically polymerizable material and(b) a photopolymerizable material is maintained in a substantially oxygen-free environment such that the composition solidifies. It is then exposed imagewise to actinic radiation and treated with a developer to remove parts of the layer which have not been struck by the radiation.The anaerobically polymerizable and photopolymerizable materials may be a mixture of two or more materials having these different functions, such as an acrylate ester with an azido compound, or the two functions may be combined in a single molecule. The products are suitable for use in producing printing plates and printed circuits.
    Type: Grant
    Filed: July 25, 1983
    Date of Patent: February 19, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Edward Irving, Terence J. Smith
  • Patent number: 4482679
    Abstract: Compositions that cure when heated comprise(A) an epoxide resin and(B) an effective amount of(i) a diaryliodosyl salt of formula ##STR1## where R.sup.1 and R.sup.2, which may be the same or different, each represents a monovalent aromatic radical of from 4 to 25 carbon atoms, such as a substituted or unsubstituted phenyl group,M represents a metal or metalloid atom, such as phosphorus or boron,X represents a halogen atom, particularly chlorine or fluorine, andn is 4, 5, or 6, and is greater by one than the valency of M or MX.sub.n.sup.- represents pentafluorohydroxoantimonate, and(ii) a catalyst for the diaryliodosyl salt which is a salt or complex of a d-block transition metal, a stannous salt, an organic peroxide, or an .alpha.-hydroxy compound.Typically, the epoxide resin (A) is a bisphenol A diglycidyl ether, the salt (i) is diphenyliodosyl tetrafluoroborate or hexafluorophosphate, and the catalyst (ii) is cupric acetylacetonate or benzpinacol.
    Type: Grant
    Filed: September 9, 1983
    Date of Patent: November 13, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Edward Irving
  • Patent number: 4463169
    Abstract: Polymerizable compositions comprise(a) a compound containing(i) at least one acryloyloxy or methacryloyloxy group,(ii) at least one allyl, methallyl, or 1-propenyl group attached, either directly, or through an oxygen atom or an oxycarbonyl group, to a carbon atom which forms part of an aromatic or cycloaliphatic nucleus,(b) a compound containing in the molecule both(iii) at least one acryloyloxy or methacryloyloxy group and(iv) at least one --COOH group, and(c) a compound containing at least two mercaptan groups directly attached to aliphatic carbon atoms.Examples of (a) are 2,2-bis(3-allyl-4-(3-(methacryloyloxy)-2-(2-carboxyethylcarbonyloxy)propox y)phenyl)propane, 1-(allyloxycarbonyl)-2,4-bis(3-(methacryloyloxy)-2-(2-carboxyethylcarbonyl oxy)propoxycarbonyl)benzene, and diallyl bis(3-methacryloyloxy)-2-(2-carboxyethylcarbonyloxy)propyl) esters of benzophenone-3,4,3',4'-tetracarboxylic acid. Examples of (b) are acrylic acid and 2-(methacryloyloxy)ethyl 5-carboxycyclohex-1-ene-4-carboxylate.
    Type: Grant
    Filed: September 13, 1982
    Date of Patent: July 31, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Edward Irving
  • Patent number: 4440802
    Abstract: Heat-curable prepregs are made by impregnating cellulosic fibers with a water-borne composition containing (a) a photopolymerizable resin of specified structure and (b) an epoxide resin, preferably together with a sensitizer for (a) and a heat-hardening agent for (b). Component (a) contains both hydrophobic and hydrophilic units and serves to keep the hydrophobic epoxide resin (b) suspended in the aqueous composition during impregnation, it then solidifying on exposure to actinic radiation. Subsequently the prepregs are heated to cure (b).Component (a) is a di(meth)acrylate containing groups of formula ##STR1## where each R.sup.19 denotes alkyl or each pair of R.sup.19 denotes --CH.sub.2 --.sub.2, --C(R.sup.21 R.sup.22)CO--, --CH.sub.2 CH(CH.sub.3)--, --CH.sub.2 --.sub.3, or --CO--.sub.2,R.sup.4 denotes a (cyclo)aliphatic or araliphatic radical,c and d are each zero or 1,R.sup.20 denotes an aliphatic group or, if each d is 1, it may denote ##STR2## R.sup.21 and R.sup.
    Type: Grant
    Filed: March 28, 1983
    Date of Patent: April 3, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Edward Irving
  • Patent number: 4439291
    Abstract: Polymerizable compositions comprise(a) a compound containing both(i) at least one acryloyloxy or methacryloyloxy group,(ii) at least one allyl, methallyl, or 1-propenyl group attached directly to a carbon atom which forms part of an aromatic nucleus or to an oxygen atom or an oxycarbonyl group which are in turn directly attached to such a carbon atom,the total of the said groups (i) and (ii) being at least three, and(b) a compound containing at least two mercaptan groups directly attached to aliphatic carbon atoms, in a proportion as to supply at least 0.8 such mercaptan group per allyl, methallyl or 1-propenyl group in (a) but less than 1.0 such mercaptan group in (a) per acryloyl, methacryloyl, allyl, methallyl, or 1-propenyl group.
    Type: Grant
    Filed: July 22, 1982
    Date of Patent: March 27, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Edward Irving, George E. Green
  • Patent number: 4439517
    Abstract: A layer of a photoresist composition on a substrate is exposed imagewise to actinic radiation, as through a negative, the photoresist composition comprising an epoxide resin, a benzenoid polyamine, and an aromatic compound which liberates an acid on exposure to actinic radiation. The composition is then heated such that where the radiation has struck the composition local curing of the epoxide resin takes place, the liberated acid acting as accelerator in the curing by the benzenoid polyamine. In parts not struck by radiation the acid accelerator is not liberated and so curing (and insolubilization of the epoxide resin in solvents) takes place much more slowly. By treatment with a suitable solvent unirradiated (and hence uncured) portions of the compositions are dissolved away, an image being formed on the substrate.
    Type: Grant
    Filed: January 10, 1983
    Date of Patent: March 27, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Edward Irving
  • Patent number: 4436880
    Abstract: Compositions containing(a) an epoxide resin containing more than one 2,3-epoxypropyl group per average molecule,(b) a boron trifluoride-amine complex which is a latent hardener for epoxide resins, such as BF.sub.3 -ethylamine, and(c) certain oxidants, such as benzoyl peroxide or 2,3-dichloro-5,6-dicyanobenzoquinone, are stable on storage at ambient temperature but cure rapidly when heated above a certain threshold temperature, the oxidant having a marked accelerating effect on the rate of curing.
    Type: Grant
    Filed: February 1, 1983
    Date of Patent: March 13, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Edward Irving
  • Patent number: 4435497
    Abstract: Polymerizable compositions comprise(a) a compound containing(i) at least one acryloyloxy or methacryloyloxy group,(ii) at least one allyl, methallyl, or 1-propenyl group attached, either directly or through an oxygen atom or an oxycarbonyl group, to a carbon atom which forms part of an aromatic or cycloaliphatic nucleus, and(iii) at least one carboxylic acid group,(b) a compound containing at least two mercaptan groups directly attached to aliphatic carbon atoms, in a proportion as to supply at least 0.8 such --SH group per allyl, methallyl, and 1-propenyl group in (a) but less than 1.0 such --SH group in (a) per acryloyl, methacryloyl, allyl, methallyl, and 1-propenyl group.
    Type: Grant
    Filed: June 7, 1982
    Date of Patent: March 6, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Edward Irving
  • Patent number: 4398014
    Abstract: New aromatic sulfonylsulfoxonium salts are of formula ##STR1## where q is 1 to 4,R denotes an aliphatic, cycloaliphatic, or aromatic group,R.sup.6 denotes H, an alkyl or aralkyl group, or a group --COR.sup.9, --CO--NH--(CO).sub.r --R.sup.10, or --SO.sub.2 --R.sup.11, where r is zero or 1,one, but not both, of R and R.sup.6 denoting an aromatic group,R.sup.7 denotes an alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, or aralkyl group,R.sup.8 has the same meaning as R.sup.7 but may alternatively represent a dialkylamino group or, if R.sup.7 denotes alkyl, it may alternatively represent an arylamino group,R.sup.9, R.sup.10, and R.sup.11 each denote an alkyl, aryl, or aralkyl radical of 1 to 25 carbon atoms,t is 1, 2, or 3, andZ.sup.- denotes a t-valent anion of a protic acid.The salts, e.g., dimethyl-p-toluenesulfonylmethylsufoxonium hexafluorophosphate, are useful as catalysts for the polymerization of cationically polymerizable materials by means of actinic radiation and/or heat.
    Type: Grant
    Filed: October 23, 1981
    Date of Patent: August 9, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: George E. Green, Edward Irving, Bernard P. Stark
  • Patent number: 4392930
    Abstract: Diacrylates or dimethacrylates, which are compatible with water before exposure to actinic radiation but after such exposure form hard, insoluble, coatings which are resistant to organic solvents and to water, are made by reaction with (meth)acrylic acid, or with a dicarboxylic acid and a hydroxy group-containing (meth)acrylate, of epoxide groups in an advanced diepoxide resin containing groups of formula ##STR1## where R.sup.4 denotes a divalent (cyclo)aliphatic or araliphatic radical,each R.sup.15 denotes an alkyl group or each pair of R.sup.15 denotes a group of formula --CH.sub.2).sub.2 --, --C(R.sup.16 R.sup.17)CO--, --CH.sub.2 CH(CH.sub.3)--, --CH.sub.2 --.sub.3, or --CO--.sub.2, wherein R.sup.16 and R.sup.17 each represent a hydrogen atom, an alkyl group, or, conjointly, a cycloaliphatic ring, andc is zero or 1.
    Type: Grant
    Filed: June 30, 1982
    Date of Patent: July 12, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Roderick D. Hathaway, Edward Irving, John S. Waterhouse
  • Patent number: 4387216
    Abstract: Certain classes of aromatic sulfoxonium salts, such as dimethylphenacylsulfoxonium and acetanilinodimethylsulfoxonium hexafluorophosphates, have little or no effect on prolonged heating with O-glycidyl group-containing epoxides. It has now been found that if a quinone, peroxide, or iodoso aromatic compound is also added, the sulfoxonium salts rapidly bring about the polymerization of such epoxides and curing of such polyepoxides.
    Type: Grant
    Filed: April 29, 1982
    Date of Patent: June 7, 1983
    Assignee: Ciba-Geigy Corporation
    Inventor: Edward Irving
  • Patent number: 4383025
    Abstract: Substances (I) capable of being converted into higher-molecular weight materials under the influence of a cationic catalyst, such as 1,2-epoxides, aminoplasts, vinyl monomers and prepolymers, or phenoplasts, are so converted by exposure to actinic radiation in the presence of an aryl- or aroyl- carbamoylsulfoxonium salt (II) of formula ##STR1## where p is zero or 1,q is 1 to 4,Ar denotes an aromatic group,R.sup.6 denotes --H or group --COR.sup.9 or --CONH(CO).sub.r R.sup.10,R.sup.7 denotes an alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aryl, or aralkyl group,R.sup.8 has the same meaning as R.sup.7 but may alternatively represent a dialkylamino group or, if R.sup.7 denotes alkyl, it may alternatively represent an arylamino group,R.sup.9 and R.sup.10 each denote a saturated or ethylenically unsaturated radical,r is zero or 1,t is 1, 2, or 3, andZ.sup.t- denotes a t-valent anion of a protic acid.
    Type: Grant
    Filed: June 29, 1981
    Date of Patent: May 10, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: George E. Green, Edward Irving
  • Patent number: 4339567
    Abstract: Substances (I) capable of being converted into higher-molecular weight materials under the influence of a cationic catalyst, such as 1,2-epoxides, aminoplasts, vinyl monomers or prepolymers, or phenoplasts, are so converted by exposure to actinic radiation in the presence of a sulphoxonium salt (II) of formula ##STR1## where P denotes zero or 1,R.sup.6 denotes an arylene or aralkylene group,R.sup.7 denotes --H or a group of formula ##STR2## R.sup.8 denotes an alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aryl, or aralkyl group,R.sup.9 has the same meaning as R.sup.8 but may alternatively represent a dialkylamino group or, if R.sup.8 represents an alkyl group, R.sup.9 may represent an arylamino group,R.sup.10 and R.sup.11 each independently have the same meaning as R.sup.8 but may also each denote --H,r represents 1, 2, or 3,Z.sup.r- denotes an r-valent anion of a protic acid, and q denotes zero when p denotes zero, or zero or 1 when p denotes 1.
    Type: Grant
    Filed: February 23, 1981
    Date of Patent: July 13, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: George E. Green, Edward Irving
  • Patent number: 4299938
    Abstract: Substances (I) capable of being converted into higher-molecular weight materials under the influence of a cationic catalyst, such as 1,2-epoxides, aminoplasts, vinyl monomers or prepolymers, or phenoplasts, are so converted by exposure to actinic irradiation or by heating in the presence of an aryloxysulfoxonium salt of formula ##STR1## where either R.sup.6 and R.sup.7 separately denote lower alkyl (optionally substituted by halogen and interrupted in the chain by --O-- or --SO.sub.2 --), or an aryl or aryloxy group, or R.sup.6 and R.sup.7 together denote a divalent group forming with the S atom a heterocyclic radical; R.sup.8 denotes an aryl group; M denotes an atom of a metal or metalloid; X denotes a halogen atom; and n is 4, 5, or 6, for instance,p-chlorophenoxy-p-tolyl-p-phenoxysulfoxonium hexafluorophosphate and 1-phenoxy-1-oxidotetrahydrothiophenium tetrafluorborate.
    Type: Grant
    Filed: June 9, 1980
    Date of Patent: November 10, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: George E. Green, Edward Irving
  • Patent number: 3963280
    Abstract: A pushrod guide and locator comprising a plate having first and second planar portions; one planar portion has an aperture for mounting the plate to an internal combustion engine and the other has a slot in which a bush having a peripheral groove is received for reciprocal movement along the length of the slot; the bush has a bore for a pushrod to pass through and reciprocate in; the arrangement is such that the reciprocal movement of the bush that is permitted is in one and an opposite direction of the pushrod through the bush.The plate is particularly intended for mounting to a stud on a cylinder head and the two planar portions have an angular and plane relation to one another appropriate to the position of mounting to the engine and the reciprocating movement of the pushrod.The guide and locator is particularly applicable to performance engines.
    Type: Grant
    Filed: February 5, 1975
    Date of Patent: June 15, 1976
    Assignee: Jeffrey Robert Hughes
    Inventor: Philip Edward Irving