Nitrogen Compound Containing Patents (Class 430/919)
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Patent number: 4618564Abstract: Positive images are produced by (i) exposing to actinic radiation in a predetermined pattern a composition supported on a substrate, which composition comprises a film-forming organic material and a substance which releases a sulphonic acid on exposure to actinic radiation, thereby rendering the composition more soluble in the developer in the exposed areas than the unexposed areas, and (ii) treating the composition with the aqueous base developer to remove the unexposed areas. The image-forming process may be used in the production of printing plates and electrical circuits.Type: GrantFiled: May 24, 1985Date of Patent: October 21, 1986Assignee: Ciba-Geigy CorporationInventors: Christopher G. Demmer, Edward Irving
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Patent number: 4608333Abstract: A radiation-sensitive composition is described, which is comprised of (1) a polymer containing repeating units of the formula: ##STR1## wherein R.sup.1 is a trivalent or tetravalent aromatic or heteroaromatic residue having 6 to 30 carbon atoms, R.sup.2 is a divalent aromatic or heteroaromatic residue having 6 to 30 carbon atoms, R.sup.3 is hydrogen or an ammonium ion, n is 1 or 2, and COOR.sup.3 is located in an ortho or peri position with respect to the amide linkage, (2) an organic compound having a radiation-dimerizable or radiation-polymerizable olefinic double bond and an amino radical or a quaternary ammonium salt, and (3) an aromatic secondary or tertiary amine compound which is chemically inactive to actinic radiation. This composition has an improved photo-sensitivity or radiation sensitivity and can give highly heat-resistant relief patterns with a good edge sharpness and good mechanical and chemical properties as well as good insulating properties.Type: GrantFiled: February 10, 1984Date of Patent: August 26, 1986Assignee: Toray Industries, Inc.Inventors: Gentaro Ohbayashi, Susumu Umemoto, Hiroo Hiramoto
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Patent number: 4604342Abstract: A photopolymerizable mixture is described which contains the following: a binding agent which is soluble or at least capable of swelling in aqueous-alkaline solutions, a photoinitiator or a photoinitiator system and at least one ethylenically unsaturated monomer, whereby at least one monomer contains an aromatic hydroxyl-, mercapto-, sulfonamide- or a mono-N-substituted sulfonamide group, or combinations thereof.Type: GrantFiled: March 13, 1985Date of Patent: August 5, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventors: Manfred A. J. Sondergeld, Mario Grossa
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Patent number: 4590145Abstract: The initiator composition is effectively used for a photopolymerizable resin composition which comprises a photopolymerizable compound having a double bond for polymerization and a polymer binder and comprises (A) thioxanthone or a substituted thioxanthone and (B) an oxime ester of the formula: ##STR1## wherein R.sub.1 and R.sub.2 may be the same or different and represent each an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted phenyl, naphthyl, anthryl, pyridyl or quinolyl group or R.sub.1 and R.sub.2 may be bonded together to form a ring, and R.sub.3 represents an alkyl group having 1 to 5 carbon atoms or a substituted or unsubstituted aryl group.Type: GrantFiled: June 28, 1985Date of Patent: May 20, 1986Assignee: Daicel Chemical Industries, Ltd.Inventors: Masanori Itoh, Fumio Takenaka, Kouzi Tohya
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Patent number: 4588664Abstract: Novel photopolymerizable compositions are provided which comprise a dye sensitizer, a branched polyethylenimine as a polymerization initiator and a free radical polymerizable ethylenic unsaturated monomer.In the preferred embodiments, the branched polyethylenimine is used in combination with lithium acrylate. This combination provides dry coatings which may be stored for extended periods prior to being activated for imaging, and which produce volume holograms of very high resolution and diffraction efficiency.Type: GrantFiled: August 20, 1984Date of Patent: May 13, 1986Assignee: Polaroid CorporationInventors: Herbert L. Fielding, Richard T. Ingwall
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Patent number: 4587197Abstract: A photosensitive polymer composition comprising (A) a poly(amic acid), (B) a compound or a mixture of compounds which can form a compound having two or more amino groups in the molecule, and (C) at least one compound having a boiling point of 150.degree. C. or higher at atmospheric pressure and selected from the group consisting of ##STR1## wherein R.sup.a, R.sup.b, R.sup.c, m and n are as defined in the specification, has good properties and does not produce cracks on a pattern at the time of development obtained from said composition.Type: GrantFiled: February 8, 1984Date of Patent: May 6, 1986Assignees: Hitachi, Ltd., Hitachi Chemical Co., Ltd.Inventors: Mithumasa Kojima, Fumio Kataoka, Fusaji Shoji, Hitoshi Yokono
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Patent number: 4585726Abstract: Photopolymerizable water-soluble or water-dispersible mixtures essentially consist of a base polymer, at least one polymerizable ethylenically unsaturated compound, at least one photoinitiator and/or photosensitizer and at least one stabilizer, the thermal polymerization inhibitor being a water-soluble salt of nitrous acid.Type: GrantFiled: July 6, 1984Date of Patent: April 29, 1986Assignee: BASF AktiengesellschaftInventors: Gunter Wallbillich, Rudolf Vyvial
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Patent number: 4584260Abstract: A photopolymerizable composition comprising an addition polymerizable unsaturated compound containing at least two ethylenically unsaturated double bonds in the molecule thereof and photopolymerization initiators, wherein a 4,4'-bis(dialkylamino)benzophenone represented by general formula I below, a benzophenone derivative represented by general formula II below and a compound having a group represented by general formula III below are contained as said photopolymerization initiators: ##STR1## wherein R represents an alkyl, cycloalkyl or hydroxyalkyl group having 1 to 6 carbon atoms or is combined with another R substituted on the same nitrogen atom to form tetramethylene, pentamethylene or oxybisethylene; ##STR2## wherein R.sup.1 represents a hydrogen atom ##STR3## X.sub.1 and X.sub.2 each represents an alkyl group, an alkoxy group, a carboxy group, an alkoxycarbonyl group, an aryloxycarbonyl group or a halogen atom; m and n each represents 0, 1 or 2 and when m and n each represents 2, X.sub.1 and X.sub.Type: GrantFiled: June 6, 1985Date of Patent: April 22, 1986Assignee: Fuji Photo Film Co., Ltd.Inventors: Masayuki Iwasaki, Minoru Maeda, Fumiaki Shinozaki
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Patent number: 4576975Abstract: Michler's ketone analogs and salts thereof, which are photosensitizers in water-soluble photoinitiator systems used to induce polymerization in free-radically-curable, ethylenically-unsaturated materials, are disclosed. The Michler's ketone analogs have the formula: ##STR1## wherein each R is an alkyl group of 1 to 8 carbon atoms,R.sup.1 is an alkylene group having 1 to 8 carbon atoms,Z is R.sup.1 COOH or R.sup.1 H, andn is an integer having a value of 1 or 2.The photoinitiator systems are useful in imaging systems, and additionally contain a free radical initiator compound selected from iodonium salts, biimidazoles, trialkylphosphites, alkyl peroxides, benzyl halides, alkyl nitrates, and the benzophenones other than (a).Type: GrantFiled: December 18, 1984Date of Patent: March 18, 1986Assignee: Minnesota Mining and Manufacturing CompanyInventor: Laurence W. Reilly, Jr.
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Patent number: 4565769Abstract: Photopolymerizable composition consisting essentially of (A) at least one ethylenically unsaturated monomeric compound, (B) at least one 2,4,5-triarylimidazolyl dimer, (C) sensitizing amount of at least one polymeric sensitizer, weight average molecular weight 10,000 to 300,000, which is the reaction product of (1) a reactive photosensitizer and (2) a reactive polymer as defined herein, and (D) optionally an organic polymeric binder. The compositions are useful in photoresists, chemical milling, toning films and printing plates.Type: GrantFiled: November 21, 1984Date of Patent: January 21, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventors: Thomas E. Dueber, Bruce M. Monroe
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Patent number: 4565767Abstract: A light-sensitive polymer composition comprising a poly(amic acid), a special bisazide compound and an amine compound can give a film which has high sensitivity and in which portions exposed to light are not easily released by a developing solution at the time of development.Type: GrantFiled: April 24, 1984Date of Patent: January 21, 1986Assignees: Hitachi, Ltd, Hitachi Chemical Company, Ltd.Inventors: Fumio Kataoka, Fusaji Shoji, Isao Obara, Issei Takemoto, Hitoshi Yokono, Tokio Isogai, Mitsumasa Kojima
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Patent number: 4556625Abstract: The present invention discloses a method of photolytically developing a colored image on a cellulosic material. In this method, the material is contacted with a nitrogen containing polymer in solution and a mono-sulfonyl azide compound in solution. The sample is thereafter exposed to a UV-containing light source for an amount of time sufficient to develop a color thereon.Type: GrantFiled: November 25, 1983Date of Patent: December 3, 1985Assignee: Armstrong World Industries, Inc.Inventors: Ronald S. Lenox, Anne L. Schwartz, Charles E. Hoyle
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Patent number: 4548690Abstract: Combinations of a vinyl monomer (or prepolymer), a catenated polysilane and an amine are photopolymerizable in the presence of oxygen.Type: GrantFiled: February 28, 1984Date of Patent: October 22, 1985Assignee: Minnesota Mining and Manufacturing CompanyInventor: Donald G. Peterson
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Patent number: 4548892Abstract: A photopolymerizable composition is described, containing an addition polymerizable, unsaturated compound having two or more ethylenically unsaturated double bonds within the molecule and a photopolymerization initiator, wherein said photopolymerization initiator is an acylhaloacetic acid amide derivative represented by formula (I) ##STR1## wherein Ar represents a substituted or unsubstituted aryl group, X represents a carbonyl or sulfonyl group, Y represents a chlorine atom or a bromine atom, R represents a hydrogen atom, a chlorine atom or a bromine atom, and R.sup.a and R.sup.b each represents a hydrogen atom, a substituted or unsubstituted alkyl group, an aryl group, or an aralkyl group.Type: GrantFiled: January 29, 1985Date of Patent: October 22, 1985Assignee: Fuji Photo Film Co., Ltd.Inventors: Masayuki Iwasaki, Minoru Maeda, Fumiaki Shinozaki, Kouichi Kawamura
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Patent number: 4543318Abstract: A photopolymerizable composition is described, comprising (1) a non-gaseous ethylenically unsaturated compound which has at least two ethylenically unsaturated terminal groups and is capable of forming a polymer, (2) a thermoplastic polymeric binder, (3) a photopolymerization initiator which is activated by actinic radiation, and (4) at least one of certain heterocyclic compounds. The composition is useful as a photoresist for producing printed circuit boards, printing plates, etc., by etching or plating, and the photoresist has superior adhesion with respect to the base.Type: GrantFiled: July 2, 1984Date of Patent: September 24, 1985Assignee: Fuji Photo Film Co., Ltd.Inventors: Minoru Maeda, Masayuki Iwasaki, Fumiaki Shinozaki
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Patent number: 4525256Abstract: There is described a photopolymerizable composition which contains at least one olefinically unsaturated compound and a photosensitive catalyst containing a diketone plus 4-(N,N-dimethylamino)benzoic acid or lower alkyl ester thereof.Type: GrantFiled: July 1, 1983Date of Patent: June 25, 1985Assignee: Johnson & Johnson Dental Products CompanyInventor: Brian Martin
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Patent number: 4518473Abstract: The photopolymerization of ethylenically unsaturated compounds is effected using a combination of an aromatic ketone photosensitizer and a tetrasubstituted urea (e.g. N,N,N',N'-tetramethylurea) or N,N-disubstituted acid amide. Storage stable liquid photoinitiator compositions comprising an aromatic ketone sensitizer (e.g. benzophenone) and a tetrasubstituted urea (e.g. N,N,N',N'-tetramethylurea) are also disclosed. The use of the tetrasubstituted urea or N,N-disubstituted amide possesses advantages (storage stability, lack of discoloration on curing) over photosensitizers such as Michler's ketone which have been used previously in combination with aromatic ketone photosensitizers.Type: GrantFiled: October 11, 1983Date of Patent: May 21, 1985Assignee: The Upjohn CompanyInventor: Anthony F. Jacobine
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Patent number: 4515887Abstract: There is provided a photosensitive modified silicone-aromatic polyamide acid convertible to a patterned silicone-polyimide. A silicone-polyamide acid is modified with an isocyanatoalkylacrylate to produce a silicone-aromatic polyamide acid having acrylate alkylamide groups attached to the silicone-aromatic polyamide acid backbone by nitrogen-nuclear bound carbon linkages.Type: GrantFiled: August 29, 1983Date of Patent: May 7, 1985Assignee: General Electric CompanyInventor: Gary C. Davis
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Patent number: 4515886Abstract: Photosensitive compositions useful as resists for transistors, ICs, etc. comprising a solution of a photosensitive high polymer of a polymer or a copolymer which contains a unit expressed by the following general formula: ##STR1## (where X.sub.1 is an atom of hydrogen or halogen, a halogenated alkyl group of 1 to 4 carbon atoms or an alkyl group having 1 to 4 carbon atoms, X.sub.2 is a halogen atom or a halogenated alkyl group having 1 to 4 carbon atoms and R is an aromatic ring or a heterocyclic ring), and a photosensitizing agent dissolved in organic solvents. The photosensitive compositions show marked improvement in photosensitivity and gamma value.Type: GrantFiled: February 13, 1984Date of Patent: May 7, 1985Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Tsuguo Yamaoka, Mitsutoshi Fukuda
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Patent number: 4499176Abstract: Aqueous compositions useful in making stencils for screen printing by the direct, indirect or direct/indirect method comprise a photopolymerizable monomer, a water-insoluble photoinitiator, a tertiary amine accelerator, a water-soluble colloid, water, and a water-miscible organic solvent.Type: GrantFiled: September 22, 1982Date of Patent: February 12, 1985Assignee: Sericol Group LimitedInventors: John R. Curtis, John D. Renwick
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Patent number: 4499175Abstract: Aqueous compositions useful in making stencils for screen printing comprise a solution of an unsaturated prepolymer dispersed in an aqueous solution of a colloid, and a photo-initiator. Such compositions may be coated on suitable support sheets to produce photosensitive sheets useful for making stencils for screen printing by the direct, indirect, or direct/indirect methods.Type: GrantFiled: September 22, 1982Date of Patent: February 12, 1985Assignee: Sericol Group LimitedInventors: John R. Curtis, John D. Renwick
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Patent number: 4496646Abstract: A photosensitive imaging material utilizing changes in adhesive properties due to light, wherein an alloxazin derivative represented by the general formula: ##STR1## [wherein R's may be the same or different from each other and each represents an alkyl group having 1 to 20 carbon atoms or a phenylalkyl group represented by the formula: ##STR2## (wherein n is an integer of 1 or more)] is used as a photopolymerization initiator, thereby enhancing the photographic speed and photographic sensitivity of the photosensitive material.Further, in order that the photosensitive material can possess image halftone reproducibility per se, the photosensitive material may be made into a composite material in which a photosensitive layer additionally containing a tertiary amine as a sensitizer is laminated on a hardened layer formed by hardening a photosensitive composition.Type: GrantFiled: November 29, 1983Date of Patent: January 29, 1985Assignee: Sony CorporationInventor: Kengo Ito
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Patent number: 4459349Abstract: A photosensitive resin composition which comprises (1) an ethylenically unsaturated compound which can be addition polymerized to form a high molecular compound, said addition polymerizaton being initiated by a free radical and of chain-propagation, (2) a 2-polycyclic aryl-4,5-diphenylimidazolyl dimer wherein the polycyclic aryl group comprises at least two benzene rings condensed each other and (3) at least one compound selected from the group consisting of dimedone, indolacetic acid, N-naphthylglycine, S-lower alkylthioglycollic acid, 4,4'-bis[di(lower)alkylamino]benzyl, p-di(lower)alkylaminobenzoic ester, leucocrystalviolet, indoxylic acid, rhodanine, 7-di(lower)alkylaminocumarine and diarylthiourea and their derivatives, the molar ratio of the component (2) and the component (3) being from 2:1 to 1:5.Type: GrantFiled: March 23, 1982Date of Patent: July 10, 1984Assignee: Toyo Boseki Kabushiki KaishaInventors: Toshikiyo Tanaka, Yoshio Katoh, Satoshi Imahashi, Toshihiko Kajima, Hisashi Uhara
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Patent number: 4454220Abstract: An electrical device coated with a polymerized polyimide structure resulting from a radiation-sensitive polyimide precursor composition which comprises a polymer of the formula ##STR1## wherein n is a positive integer corresponding to the number of units in the polymer and is sufficiently large to provide the polymer with a number average molecular weight of about 1500-15,000 as determined by vapor pressure osmometry, and wherein for any particular unit in the polymer:.fwdarw.denotes isomerism; R.sup.1 is a divalent aromatic, aliphatic or cycloaliphatic radical containing at least 2 carbon atoms; R.sup.2 and R.sup.3 are selected from the group consisting of a hydrogen radical and any organic radical containing a photopolymerizable olefinic double bond; and R.sup.4 and R.sup.5 are selected from the group consisting of perfluoro and perhalofluoro aliphatic hydrocarbons having 1 to 8 carbons.Type: GrantFiled: September 29, 1982Date of Patent: June 12, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventor: David L. Goff
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Patent number: 4451551Abstract: A light- or radiation-sensitive polymer composition comprising (a) a poly(amic acid) having as a major component a repeating unit of the formula: ##STR1## (b) one or more light- or radiation-sensitive compounds having an amino group and an aromatic azide group or aromatic sulfonylazide group in one molecule, and if necessary (c) one or more photosensitizers and/or amine compounds having at least one unsaturated bonding, and/or (d) one or more compounds having at least two unsaturated bonding in one molecule, is highly sensitive to light and radiation and can give a precise relief pattern on a substrate. Further, a finally obtained polyimide film is excellent in heat resistance.Type: GrantFiled: December 17, 1981Date of Patent: May 29, 1984Assignees: Hitachi, Ltd., Hitachi Chemical CompanyInventors: Fumio Kataoka, Fusaji Shoji, Isao Obara, Hitoshi Yokono, Tokio Isogai, Mitumasa Kojima
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Patent number: 4439517Abstract: 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: GrantFiled: January 10, 1983Date of Patent: March 27, 1984Assignee: Ciba-Geigy CorporationInventor: Edward Irving
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Patent number: 4439515Abstract: A light-sensitive composition comprising addition polymerizable ethylenically unsaturated double bond-containing compounds and a photopolymerization initiator comprising (1) at least one compound selected from the group consisting of benzanthrone, substituted benzanthrones (the substituents of which include halogen atoms, alkyl groups having 1 to 5 carbon atoms and alkoxy groups having 1 to 5 carbon atoms), 1,2-benzanthraquinone and substituted benzanthraquinones (substituents of which include halogen atoms, alkyl groups having 1 to 5 carbon atoms and alkoxy groups having 1 to 5 carbon atoms) and (2) at least one compound selected from the group consisting of 4,4'-di-substituted amino-benzophenones represented by the following general formula (a), p-substituted amino-benzaldehyde derivatives represented by the following general formula (b), 2-(p-substituted amino-phenyl)-1,3-dioxolanes represented by the following general formula (c), 4,4'-bis(substituted amino)-N-benzylideneanilines represented by the followType: GrantFiled: April 14, 1983Date of Patent: March 27, 1984Assignee: Fuji Photo Film Co., Ltd.Inventors: Fumiaki Shinozaki, Yasuo Washizawa, Tomoaki Ikeda, Sho Nakao, Syunichi Kondoh
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Patent number: 4438190Abstract: A photosensitive resin composition comprising (a) at least one compound selected from the group consisting of benzotriazole, benzimidazole, benzothiazole, derivatives thereof and salts thereof, (b) a phosphate compound having photopolymeric unsaturated bonds, (c), if necessary, an organic thermoplastic polymer, (d) a photopolymerizable unsaturated compound having at least one terminal ethylene group and (e) a sensitizer and/or a sensitizer system, and a photosensitive element comprising a layer of said photosensitive resin composition and a support film therefor, are provided. The photosensitive resin composition can form a protective coating film with excellent adhesiveness to the substrate surface, and such a protective coating film or, photosensitive element obtained therefrom can be advantageously used as a resist for soldering mask, etc.Type: GrantFiled: February 24, 1982Date of Patent: March 20, 1984Assignee: Hitachi Chemical Company, Ltd.Inventors: Toshiaki Ishimaru, Katsushige Tsukada, Nobuyuki Hayashi
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Patent number: 4437836Abstract: In a photopolymerizable composition comprising(a) at least one ethylenically unsaturated photopolymerizable monomer.(b) at least one photoinitiator selected from organic mono- and/or di-carbonyl compounds and(c) a photoactivator, the improvement which comprises employing as said photoactivator at least one alkylaminoarylsulphonyl compound of the formula ##STR1## in which R.sub.1 and R.sub.2 each independently is a hydrogen atom or an alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl or alkaryl group which has 1 to 11 carbon atoms and is optionally substituted by at least one hydroxyl, amino, epoxy, urethane, urea, ether of ether group, or R.sub.1 and R.sub.2 together form a 3- to 6-membered ring, which optionally contains nitrogen, oxygen or sulphur as a hetero-atom,R.sub.3 independently of R.sub.1, has any of the meanings given for R.sub.1 or is a group of the formula ##STR2## R.sub.4 and R.sub.Type: GrantFiled: September 1, 1982Date of Patent: March 20, 1984Assignee: Bayer AktiengesellschaftInventors: Robert Schmitz-Josten, Carlhans Suling, Wolfgang Podszun, Bruno Bomer, Manfred Borgardt, Michael Walkowiak
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Patent number: 4434035Abstract: Mixtures containing at least one hydroxyalkylphenone of the formula ##STR1## wherein R.sup.1 is H, alkyl of 1-4 C atoms or chlorine, R.sup.2 is H or methyl, R.sup.3 is H or methyl, R.sup.4 is alkyl of 1-6 C atoms and R.sup.5 is alkyl of 1-6 C atoms, and at least one 2-alkylthioxanthone of the formula ##STR2## wherein R.sup.6 is alkyl of 1-8 C atoms, have a considerably increased reactivity in initiating the photopolymerization of ethylenically unsaturated compounds. The polymers fully hardened using these initiator mixtures suffer only little yellowing.Type: GrantFiled: April 4, 1983Date of Patent: February 28, 1984Assignee: Merck Patent Gesellschaft mit beschr/a/ nkter HaftungInventors: J/u/ rgen Eichler, Claus Herz, Karl-Heinz Neisius
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Patent number: 4430418Abstract: A radiation-sensitive polyimide precursor composition, comprising a polymer of the formula ##STR1## wherein n is a positive integer corresponding to the number of units in the polymer and is sufficiently large to provide the polymer with a number average molecular weight of about 1500-15,000 as determined by vapor pressure osmometry, and wherein for any particular unit in the polymer:.fwdarw.denotes isomerism;R.sup.1 is a tetravalent aromatic non-halogen containing organic radical containing at least one ring of six carbon atoms, said ring characterized by benzenoid unsaturation, the four carbonyl groups being attached directly to separate carbon atoms in a ring of the R.sup.1 radical;R.sup.2 and R.sup.3 are selected from the group consisting of a hydrogen radical and any organic radical containing a photopolymerizable olefinic double bond, at least one of R.sup.2 and R.sup.3 being said organic radical;R.sup.4 and R.sup.Type: GrantFiled: September 30, 1982Date of Patent: February 7, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventor: David L. Goff
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Patent number: 4419438Abstract: An image reproducing material comprising a supporting sheet bearing a metal or metallic compound layer having a thickness of 100 to 1000 .ANG. and a photosensitive resin layer, which is characterized in that said photosensitive resin layer contains (1) an ethylenically unsaturated compound which is polymerizable by the action of free radical and chain propagative, (2) a compound showing photochromism by radical mechanism, (3) a free radical producing agent and (4) an acitinic light absorber. There is also provided an image formed (reproduced) material obtained by patterned exposing the above image reproducing material and then processing the same, a method for obtaining such image formed material and also a method for dot-etching such image formed material. By the use of these materials and methods, dot-etching can be effected easily and there are obtained sharp images without the formation of pin holes.Type: GrantFiled: March 9, 1982Date of Patent: December 6, 1983Assignee: Toyo Boseki Kabushiki KaishaInventors: Kuniomi Etoh, Toshikiyo Tanaka, Yoshio Katoh, Takeo Sugiura, Yoshiyasu Itoh, Takeo Kohira
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Patent number: 4416973Abstract: A radiation-sensitive polyimide precursor composition comprises a polymer of the formula ##STR1## wherein n is a positive integer corresponding to the number of units in the polymer and is sufficiently large to provide the polymer with a number average molecular weight of about 1500-15,000 as determined by vapor pressure osmometry, and wherein for any particular unit in the polymer:.fwdarw.denotes isomerism; R.sup.1 is a divalent aromatic, aliphatic or cycloaliphatic radical containing at least 2 carbon atoms; R.sup.2 and R.sup.3 are selected from the group consisting of a hydrogen radical and any organic radical containing a photopolymerizable olefinic double bond; and R.sup.4 and R.sup.5 are selected from the group consisting of perfluoro and perhalofluoro aliphatic hydrocarbons having 1 to 8 carbons.Type: GrantFiled: September 29, 1982Date of Patent: November 22, 1983Assignee: E. I. Du Pont de Nemours & Co.Inventor: David L. Goff
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Patent number: 4401745Abstract: A composition for ultra-fine pattern formation comprising at least one of acrylic and/or vinyl ketone polymers as the major component and an effective amount of an aromatic azide compound and, in another embodiment, further comprising an effective amount of an organic compound having a vinyl group, and a process for ultra-fine pattern formation therewith. In the process, a required area of a film formed from the composition is irradiated with a corpuscular beam or with electromagnetic wave radiation. The aromatic azide compound or a mixture thereof with the aromatic compound having a vinyl group only in the unexposed areas is subjected to a deactivation treatment within the film, and the unexposed areas of the film are removed with a gas plasma to form an ultra-fine pattern. The composition is suitable for use in the ultra-fine pattern formation of a resist for transistors, integrated circuits (IC), large scale integrated circuits (LSI) or the like in the semiconductor industry.Type: GrantFiled: August 26, 1981Date of Patent: August 30, 1983Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hisashi Nakane, Wataru Kanai, Minoru Tsuda
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Patent number: 4386153Abstract: A light-sensitive composition comprising addition polymerizable ethylenically unsaturated double bond-containing compounds and a photopolymerization initiator comprising (1) at least one compound selected from the group consisting of benzanthrone, substituted benzanthrones (the substituents of which include halogen atoms, alkyl groups having 1 to 5 carbon atoms and alkoxy groups having 1 to 5 carbon atoms), 1,2-benzanthraquinone and substituted benzanthraquinones (substituents of which include halogen atoms, alkyl groups having 1 to 5 carbon atoms and alkoxy groups having 1 to 5 carbon atoms) and (2) at least one compound selected from the group consisting of 4,4'-di-substituted amino-benzophenones represented by the following general formula (a), p-substituted amino-benzaldehyde derivatives represented by the following general formula (b), 2-(p-substituted amino-phenyl)-1,3-dioxolanes represented by the following general formula (c), 4,4'-bis(substituted amino)-N-benzylideneanilines represented by the followType: GrantFiled: March 4, 1981Date of Patent: May 31, 1983Assignee: Fuji Photo Film Co., Ltd.Inventors: Fumiaki Shinozaki, Yasuo Washizawa, Tomoaki Ikeda, Sho Nakao, Syunichi Kondoh
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Patent number: 4383903Abstract: A photo-curable resin composition is disclosed comprising (i) a mixture and/or a preliminary reaction product of (a) at least one cyanate compound selected from the group consisting of polyfunctional cyanate esters, prepolymers of the cyanate esters, coprepolymers of the cyanate esters and an amine and mixtures thereof, (b) at least one compound selected from the group consisting of monomers having at least one olefinically double bond prepolymers of the monomers, liquid rubbers having one or more acryloyl or methacryloyl groups and mixtures thereof and optionally (c) at least one maleimide compound selected from the group consisting of polyfunctional maleimides, prepolymers of the maleimides, coprepolymers of the maleimides and an amine and mixtures thereof and (ii) a photo polymerization initiator or a photo sensitizer.Type: GrantFiled: April 3, 1981Date of Patent: May 17, 1983Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Satoshi Ayano, Morio Gaku, Nobuyuki Ikeguchi, Hidenori Kinbara, Yasunari Osaki
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Patent number: 4370403Abstract: A photopolymerizable radiation-sensitive resin composition comprising a styrene-maleic acid copolymeric resin as well as an ethylenically unsaturated compound and a photopolymerization initiator is disclosed. A radiation-sensitive sheet material comprising a support (10) having coated thereon a layer (11) of the photopolymerizable radiation-sensitive resin composition is also disclosed. The composition and sheet material disclosed herein can be conveniently used particularly in the preparation of various cards such as credit cards, banking or cash cards and the like.TECHNICAL FIELDThe present invention relates to a photopolymerizable radiation-sensitive resin composition and a radiation-sensitive sheet material comprising a layer of such composition.Type: GrantFiled: April 24, 1981Date of Patent: January 25, 1983Assignees: Tokuji Arai, Birger TakleInventor: Kiyofumi Takaki
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Patent number: 4367280Abstract: A photopolymerizable composition comprising, as essential components,(1) a polymerizable compound having at least one ethylenically unsaturated double bond and(2) a photopolymerization initiator, the photopolymerization initiator being a combination of (a) an aromatic carbonyl compound and (b) a p-dialkylamino aromatic carbonyl compound.Type: GrantFiled: March 11, 1981Date of Patent: January 4, 1983Assignee: Fuji Photo Film Co., Ltd.Inventors: Syunichi Kondo, Akihiro Matsufuji, Akira Umehara
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Patent number: 4358529Abstract: A nonsilver photosensitive reproduction element which comprises a support bearing a layer of a photosensitive composition which comprises (1) at least one thermoplastic binder, (2) a photosensitive system consisting essentially of (a) a hexaarylbiimidazole compound and (b) a dihydropyridine compound; and optionally (3) a plasticizer, and (4) a thioamide, thiolactam or thiocarbanilic acid ester of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are as defined. The photosensitive element is useful in preparing negative tonable images.Type: GrantFiled: June 17, 1981Date of Patent: November 9, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventor: Werner Abele
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Patent number: 4356247Abstract: A light-sensitive composition particularly suitable for making light-sensitive lithographic printing plates is described composed of a mixture of a sensitizer and a photo-crosslinkable polymer, or a mixture of a sensitizer, a compound including a light-sensitive azido group and a polymer reactive with a decomposate of azido groups to be formed upon exposure to light, and a sensitizer represented by the formula (I) ##STR1## wherein A represents a non-metallic atomic group necessary for forming a heterocyclic ring containing nitrogen; R.sub.1 represents an alkyl group or a substituted alkyl group; R.sub.2 represents hydrogen, an alkyl group, a substituted alkyl group, an aryl group, or a substituted aryl group; and Y and Z each represents an oxygen atom or a sulfur atom.Type: GrantFiled: October 27, 1980Date of Patent: October 26, 1982Assignee: Fuji Photo Film Co., Ltd.Inventors: Yoshimasa Aotani, Teruo Kojima, Eiji Nakakita
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Patent number: 4353787Abstract: A photo-initiator system of a polyester resin is disclosed which consists of an oxime carbonate of a vicinal diketone (I), a photo-reducible dye (II) and an amine (III). This system is capable of polymerizing and curing unsaturated polyester resins by irradiation with visible light to provide coatings, adhesives, castings and fibre reinforced composites.The formulae of the ingredients of the system are ##STR1## where R' and R" are independently alkyl, aryl or aralkyl (R' preferably being CH.sub.3 and R" C.sub.2 H.sub.5) ##STR2## wherein X=Br or I on at least 2 positionsY=H, Br, IZ=H, COOM, COOR wherein R=C.sub.1 -C.sub.5 alyl.M=H, K, Na, Li, NH.sub.4(there preferably being 4X substituents which are Br, and Z preferably being --COOM or --COOR), and wherein also 4Y substituents may be present and preferably be I) and (III) ##STR3## wherein R.sub.1 is H, alkyl, hydroxy-substituted alkyl, aryl or aralkyl. R.sub.2 is independently alkyl, hydroxyl substituted alkyl, aryl or aralkyl.Type: GrantFiled: May 21, 1981Date of Patent: October 12, 1982Assignee: Scott Bader Company LimitedInventors: Ian J. Alexander, Roger J. Scott
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Patent number: 4351893Abstract: Sensitizers for photopolymerizable compositions, the sensitizers being .alpha.,.beta.-unsaturated ketones derived from acetyltetrahydronaphthalene or acetylindane and dialkylaminoaryl aldehyde; and the photopolymerizable compositions comprising said sensitizers.Type: GrantFiled: December 31, 1980Date of Patent: September 28, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventor: Albert G. Anderson
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Patent number: 4346162Abstract: A nonsilver photosensitive reproduction element for preparing negative tonable images which comprises a support bearing a layer of a photosensitive composition which comprises at least one thermoplastic binder, at least one thio compound of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are as defined, and at least one hexaarylbisimidazole compound as defined. Optionally plasticizers, stabilizers, etc. can be present in the photosensitive layer. The photosensitive element is useful in preparing negative tonable images.Type: GrantFiled: June 17, 1981Date of Patent: August 24, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventor: Werner Abele
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Patent number: 4332874Abstract: Disclosed are a photosensitive composition comprising a copolymer comprising acrylamide, diacetone-acrylamide and a sulfonated vinyl monomer, such as sodium p-styrenesulfonate, and a water-soluble aromatic bisazide compound, and a pattern-forming method using this photosensitive composition.This photosensitive composition has a reciprocity law failure, and when this photosensitive composition is used, the development after light exposure is completed in a short time.Type: GrantFiled: October 24, 1980Date of Patent: June 1, 1982Assignee: Hitachi, Ltd.Inventors: Nobuaki Hayashi, Motoo Akagi, Kiyoshi Miura, Yoshiyuki Odaka
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Patent number: 4321118Abstract: Aromatic-aliphatic ketones of the formulae I, II, III or IV ##STR1## wherein n is 1 or 2, Ar is an aryl radical, R.sup.1 and R.sup.2 are monovalent aliphatic, cycloaliphatic or araliphatic radicals, R.sup.3 is a direct bond or a divalent organic radical, X is a hydroxyl or amino group or the monovalent etherification or silylation products thereof, and X' is a divalent amino, ether or silyloxy group, Y is a direct bond or CH.sub.2 and Z is O, S, SO.sub.2, CH.sub.2 or C(CH.sub.3).sub.2, are suitable sensitizers for the photopolymerization of unsaturated compounds and for the photochemical crosslinking of polyolefins. Some of these compounds are novel and can be obtained by methods analogous to those for obtaining the known compounds of this type.Type: GrantFiled: December 19, 1979Date of Patent: March 23, 1982Assignee: Ciba-Geigy CorporationInventors: Louis Felder, Rudolf Kirchmayr, Rinaldo Husler
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Patent number: 4318791Abstract: Aromatic-aliphatic ketones of the formulae I, II, III or IV ##STR1## wherein n is 1 or 2, Ar is an aryl radical, R.sup.1 and R.sup.2 are monovalent aliphatic, cycloaliphatic or araliphatic radicals, R.sup.3 is a direct bond or a divalent organic radical, X is a hydroxyl or amino group or the monovalent etherification or silylation products thereof, and X' is a divalent amino, ether or silyloxy group, Y is a direct bond or CH.sub.2 and Z is O, S, SO.sub.2, CH.sub.2 or C(CH.sub.3).sub.2, are suitable sensitizers for the photopolymerization of unsaturated compounds and for the photochemical crosslinking of polyolefins. Some of these compounds are novel and can be obtained by methods analogous to those for obtaining the known compounds of this type.Type: GrantFiled: December 18, 1978Date of Patent: March 9, 1982Assignee: Ciba-Geigy CorporationInventors: Louis Felder, Rudolf Kirchmayr, Husler
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Patent number: 4315807Abstract: Aromatic-aliphatic ketones of the formulae I, II, III or IV ##STR1## wherein n is 1 or 2, Ar is an aryl radical, R.sup.1 and R.sup.2 are monovalent aliphatic, cycloaliphatic or araliphatic radicals, R.sup.3 is a direct bond or a divalent organic radical, X is a hydroxyl or amino group or the monovalent etherification or silylation products thereof, and X' is a divalent amino, ether or silyloxy group, Y is a direct bond or CH.sub.2 and Z is O, S, SO.sub.2, CH.sub.2 or C(CH.sub.3).sub.2, are suitable sensitizers for the photopolymerization of unsaturated compounds and for the photochemical crosslinking of polyolefins. Some of these compounds are novel and can be obtained by methods analogous to those for obtaining the known compounds of this type.Type: GrantFiled: December 28, 1979Date of Patent: February 16, 1982Assignee: Ciba-Geigy CorporationInventors: Louis Felder, Rudolf Kirchmayr, Rinaldo Husler
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Patent number: 4298679Abstract: A light-sensitive composition comprising addition polymerizable ethylenically unsaturated double bond-containing compounds and a photopolymerization initiator comprising (1) at least one compound selected from the group consisting of benzanthrone, substituted benzanthrones (the substituents of which include halogen atoms, alkyl groups having 1 to 5 carbon atoms and alkoxy groups having 1 to 5 carbon atoms), 1,2-benzanthraquinone and substituted benzanthraquinones (substituents of which include halogen atoms, alkyl groups having 1 to 5 carbon atoms and alkoxy groups having 1 to 5 carbon atoms) and (2) at least one compound selected from the group consisting of 4,4'-di-substituted amino-benzophenones represented by the following general formula (a), p-substituted amino-benzaldehyde derivatives represented by the following general formula (b), 2-(p-substituted amino-phenyl)-1,3-dioxolanes represented by the following general formula (c), 4,4'-bis(substituted amino)-N-benzylideneanilines represented by the followType: GrantFiled: July 12, 1979Date of Patent: November 3, 1981Assignee: Fuji Photo Film Co., Ltd.Inventors: Fumiaki Shinozaki, Yasuo Washigawa, Tomoaki Ikeda, Sho Nakao, Syunichi Kondoh
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Patent number: 4292398Abstract: The invention relates to a method for making more efficient the preparation of relief structures by phototechniques from mixtures containing acrylate- and/or methacrylate-group-containing polymers and photo-initiators. For this purpose, the invention provides the use of aromatic azides free of maleinimide groups as photo-initiators. The method according to the invention is suitable particularly for the structurization by phototechniques of insulating materials as well as of semiconductor and conductor materials.Type: GrantFiled: May 9, 1980Date of Patent: September 29, 1981Assignee: Siemens AktiengesellschaftInventors: Roland Rubner, Eberhard Kuhn, Hellmut Ahne
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Patent number: 4289844Abstract: A photopolymerizable composition, element and method of photopolymerizing the composition or element are disclosed wherein the composition comprises an addition polymerizable compound containing ethylenic unsaturation and a co-initiator including a photopolymerization activator and a photosensitizer.In one aspect of the invention, the photosensitizer is selected to be a coumarin having an absorption maximum between about 250 and about 550 nm, and a ##STR1## substituent in the 3-position wherein R.sup.1 is alkyl or alkenyl having 1-12 carbon atoms, or a carbocyclic or heterocyclic group having 5-20 nuclear carbon and hetero atoms, the coumarin and the activator being present in an amount sufficient to provide, when the composition is coated, dried and exposed to a medium-pressure mercury light source, a speed which is at least about one-fifth that of the same composition coated, dried and exposed identically except with a co-initiator consisting of Michler's ketone and benzophenone.Type: GrantFiled: September 5, 1980Date of Patent: September 15, 1981Assignee: Eastman Kodak CompanyInventors: Donald P. Specht, Conrad G. Houle, Samir Y. Farid