Polymeric Mixture Patents (Class 430/176)
  • Patent number: 4937170
    Abstract: A photographic element formed from a substrate and light sensitive coating on the substrate wherein the coating comprises a mixture of a diazo compound and an aromatic carboxylic coupling agent having phenolic hydroxy groups, in an acidic medium.
    Type: Grant
    Filed: March 1, 1988
    Date of Patent: June 26, 1990
    Assignee: Hoechst Celanese Corporation
    Inventor: Dieter Mohr
  • Patent number: 4931379
    Abstract: The present invention relates to increasing the autodecomposition temperature of particular resists. The resists are comprised of structures having recurrent acid labile groups which are typically pendant to the polymeric backbone. The autodecomposition temperature of a resist is increased by selecting substituent sidechains on the acid labile group which exhibit increased stability. Sidechain structures which provide increased autodecomposition stability include secondary structures capable of forming secondary carbonium ion intermediates and having an available proton adjacent to the carbonium ion formed during cleavage. Moieties which can be used as the secondary sidechain structures include secondary alkyl, including both cyclic and alicyclic alkyl, substituted deactivated secondary benzyl, and 1-(deactivated heterocyclic) secondary alkyl.
    Type: Grant
    Filed: November 3, 1988
    Date of Patent: June 5, 1990
    Assignee: International Business Machines Corporation
    Inventors: William R. Brunsvold, Willard E. Conley, Dale M. Crockatt, Nancy E. Iwamoto
  • Patent number: 4927736
    Abstract: This invention relates to novel hydroxy polyimides and radiation sensitive compositions prepared therefrom. More particularly the invention relates to positive photoresists useful in the preparation of a thermally stable relief pattern on a substrate e.g. a silicon wafer or aluminum plate. The novel hydroxy polyimides of the invention may also be used to provide thermally stable organic protective films and layers e.g. an insulating and/or a passivating layer in a semi-conductor component.The novel hydroxy polyimides of in this invention can be synthesized by the condensation of a hydroxy-substituted aminophenol and a dianhydride. Radiation sensitive compositions prepared from the novel hydroxy polyimides of the invention can be developed in aqueous base developer or organic solvent developer; preferably aqueous base developer. Also, the base developer dissolution properties of the polyimides can be controlled by incorporating a non-hydroxyl diamine into the polyimide.
    Type: Grant
    Filed: July 21, 1987
    Date of Patent: May 22, 1990
    Assignee: Hoechst Celanese Corporation
    Inventors: Werner H. Mueller, Dinesh N. Khanna
  • Patent number: 4914000
    Abstract: A light-sensitive compound having the formula: ##STR1## wherein R.sub.3 is selected from the group consisting of phenyl and C.sub.1 to C.sub.4 alklyl substituted phenyl.--K-- is selected from the group consisting of ##STR2## --S--, --O--, and --CH.sub.2 --, or is absent; R.sub.1 and R.sub.2 are independently selected from the group consisting of C.sub.1 to C.sub.4 alkyl, methoxy, ethoxy, butoxy, and H;X-- is an anion; andR denotes a hydrogen atom or a C.sub.1 to C.sub.4 alkyl group.
    Type: Grant
    Filed: February 3, 1988
    Date of Patent: April 3, 1990
    Assignee: Hoechst Celanese Corporation
    Inventor: Major S. Dhillon
  • Patent number: 4914039
    Abstract: This invention relates to water developable, negative working photosensitized sheet constructions which, upon exposure to an actinic radiation source through a screened image, can accurately reproduce said image. The construction is useful as a color proofing film which can be employed to predict the image quality from a lithographic printing process. The invention provides both overlay and transfer type proofing sheets which have good fingerprint resistance.
    Type: Grant
    Filed: April 20, 1988
    Date of Patent: April 3, 1990
    Assignee: Hoechst Celanese Corporation
    Inventor: Stanley F. Wanat
  • Patent number: 4912018
    Abstract: Photoresist compositions suitable for deep UV and excimer laser lithography are disclosed that are mixtures of a photoacid and a polymer having imide residues to which acid labile groups are attached.The imide group ##STR1## can be blocked with certain groups, X, to form compounds containing the structure ##STR2## which have solubility properties different from the unblocked imide. These groups, X, can be cleaved by acid under the proper conditions to regenerate the unblocked imide. Where the imide group is incorporated in a polymer, the polymer with blocked imide groups can be made to function as a resist when compounded with a substance capable of forming an acid upon exposure to radiation.Preferred polymers are those in which at least 80% of the imide groups are blocked. When less than 50% of the imide groups are blocked, performance in a photoresist becomes unacceptable.
    Type: Grant
    Filed: June 22, 1987
    Date of Patent: March 27, 1990
    Assignee: Hoechst Celanese Corporation
    Inventors: Christopher E. Osuch, Michael J. McFarland
  • Patent number: 4902602
    Abstract: Light-sensitive compositions comprise a light-sensitive diazo resin, a binder and a compound having a pivaloyl group. Lithographic printing plates prepared by using the light-sensitive compositions of the invention are excellent in ink receptivity.
    Type: Grant
    Filed: April 15, 1988
    Date of Patent: February 20, 1990
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Hiroshi Misu, Koichiro Aono, Yoshimasa Aotani
  • Patent number: 4877711
    Abstract: A light-sensitive composition which contains a polyurethane resin having a carbon-carbon unsaturated bond and a carboxyl group. A presensitized plate using the above light-sensitive composition can be developed with an aqueous alkaline developing solution and provides a lithographic printing plate having excellent printing durability.
    Type: Grant
    Filed: May 12, 1987
    Date of Patent: October 31, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshiaki Aoai, Kazuo Maemoto, Akihiko Kamiya, Hiroshi Misu
  • Patent number: 4859562
    Abstract: A photosensitive mixture that contains a photosensitive compound, for example, a photoinitiator or a diazo compound, and a reaction product of a polymer containing active hydrogen with an olefinically unsaturated compound represented by the formula ##STR1## wherein X and Y are the same or different and denote oxygen or sulfur,R.sub.1 is an olefinically unsaturated aliphatic radical containing 2 to 8 carbon atoms andR.sub.2 is a saturated aliphatic radical containing 1 to 8 carbon atoms or an aryl radical containing 6 to 10 carbon atoms,is suitable for producing photoresists and printing plates.
    Type: Grant
    Filed: May 8, 1987
    Date of Patent: August 22, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Georg Pawlowski, Hans-Jerg Kleiner, Thomas Gerdau
  • Patent number: 4851319
    Abstract: This invention relates to a radiation polymerizable composition for use in a photographic element such as a lithographic printing plate comprising in admixturea) a polymeric binder;b) a photoinitiator;c) a diazonium salt; andd) a photopolymerizable mixture ofi) a polyfunctional acrylic monomer having from 3 to 6 unsaturated groups; andii) a monofunctional acrylic monomer having 1 unsaturated group.
    Type: Grant
    Filed: April 19, 1988
    Date of Patent: July 25, 1989
    Assignee: Hoechst Celanese Corporation
    Inventors: John E. Walls, Carlos Tellechea
  • Patent number: 4845009
    Abstract: The present invention relates to a photosensitive composition suitable for the use in the preparation of a photosensitive lithographic plate. The photosensitive composition comprises (1) a polymer having a maleimido group in its side chain and being capable of being photocrosslinked, such as a copolymer of methyl methacrylate/N-[2-(methacryloyloxy)-ethyl]-2,3-dimethylmaleimide/methacryl ic acid=15/65/20 (weight ratio) and (2) a diazo resin such as dodecylbenzenesulfonate of condensate of p-diazodiphenylamine and formaldehyde.
    Type: Grant
    Filed: September 17, 1986
    Date of Patent: July 4, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Nobuyuki Kita, Masanori Imai
  • Patent number: 4842983
    Abstract: A light-sensitive composition comprising a phenolic resol wherein the ratio of the number of dibenzylic ether linkages to the total number of dibenzylic ether, methylene and methylol linkages linked to phenolic nucleus is 15 mol. % or more and which is obtained by a reaction between a phenol of the formul (I): ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 may be the same or different and represent hydrogen, halogen, hydroxyl, nitro, alkyl, alkoxy, phenyl, or substituted phenyl, and an aldehyde or ketone.A light-sensitive composition comprising a condensate of the phenolic resol and an o-quinone diazido sulfonylhalide.A light-sensitive material comprising the above-mentioned composition.A method for making a planographic printing plate from the light-sensitive material, characterized in that burning-in process is carried out at a lower temperature or a shortened time.
    Type: Grant
    Filed: October 14, 1987
    Date of Patent: June 27, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Akira Hasegawa
  • Patent number: 4840868
    Abstract: A photosensitive composition is described, which contains a diazonium salt polycondensation product and a polymeric binder which is soluble or at least swellable in aqueous-alkaline solutions and comprises a reaction product of a trimellitic anhydride, the free carboxyl group of which is esterified with an alcohol containing a urethane group, with a polymer containing hydroxyl groups and having no further functional groups capable of reaction with acid anhydrides. The composition yields an increased print run and has, at the same time, good storability and developability.
    Type: Grant
    Filed: December 21, 1987
    Date of Patent: June 20, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Georg Pawlowski, Guenter Hultsch, Gerhard Mack
  • Patent number: 4839254
    Abstract: A photosensitive mixture contains a photosensitive compound and a polymeric binder which s a reaction product of a compound represented by the formula ##STR1## wherein X and Y are the same or different, and each denotes oxygen or sulfur,R.sub.1 and R.sub.2 are the same or different, and each denotes an unsubstituted or substituted alkyl, cycloalkyl or alkoxy radical containing from 1 to 6 carbon atoms; an unsubstituted or substituted aryl or aryloxy radical containing from 6 to 10 carbon atoms; or, together with the phosphorus atom, a 5- or 6-membered heterocyclic ring which is unsubstituted or substituted or which carries a fused benzene ring,with a polymer containing active hydrogen. The novel binders used in the mixture can be easily prepared and yield photosensitive layers of good developability and developer resistance.
    Type: Grant
    Filed: May 8, 1987
    Date of Patent: June 13, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Georg Pawlowski, Hans-Jerg Kleiner
  • Patent number: 4833061
    Abstract: Photosensitive compositions having surfactant vesicles therein are described. A method is also shown in which the photosensitive vesicle containing an enclosed substance is exposed to light to control the release of the substance.
    Type: Grant
    Filed: April 6, 1987
    Date of Patent: May 23, 1989
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: David A. Tirrell
  • Patent number: 4828958
    Abstract: The photosensitive composite of the present invention is obtained by including a nonsubstitutional or substitutional benzyl radical in the phenol side chain of polyvinylphenol. The photosensitive composites have not only excellent heat resistivity, RIE resistivity, and resolving power but also have a wide tolerance for the variations in the development temperature and developer concentration at the time of development. Therefore, it is possible to obtain resist patterns with fine structure.
    Type: Grant
    Filed: March 9, 1987
    Date of Patent: May 9, 1989
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Shuzi Hayase, Yasunobu Onishi, Rumiko Horiguchi
  • Patent number: 4828947
    Abstract: A method for making a relief pattern of a cured resin on a transparent colored layer which comprises applying a coating of a photocurable resin composition whose spectral sensitivity varies depending on the pH of the composition, on a transparent colored layer, adjusting the pH of the composition to a predetermined level, and exposing the coating to visible light irradiation through the transparent colored layer. The irradiated layer is developed to obtain a relief pattern corresponding to visible spectra transmitted through the transparent colored layer.
    Type: Grant
    Filed: September 21, 1987
    Date of Patent: May 9, 1989
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Shigehiro Sato, Tokihiko Shimizu
  • Patent number: 4828959
    Abstract: A light-sensitive mixture that contains a diazonium salt polycondensation product, a polymeric binder and an organic peroxide which has a scorch temperature of at least 100.degree. C. and, above this temperaure, is capable of forming free radicals is especially useful for the preparation of planographic printing plates, the print run of which can be extended by burning-in the exposed and developed plate. The light-sensitive mixture has a long storage life in the dark.
    Type: Grant
    Filed: May 22, 1987
    Date of Patent: May 9, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Georg Pawlowski, Dieter Mohr, Guenter Jung
  • Patent number: 4822716
    Abstract: The polysilanes and polysiloxanes of the present invention are polymers that contain silicon in the principal chain, and contain in the side chains alkaline soluble groups such as phenol-based hydroxy group and carboxyl group.One silicone resist material of the present invention comprises the polysilane or the polysiloxane in the above.Another silicone resist material of the present invention contains the above polysilane or polysiloxane, and an appropriate photosensitive agent.Still another silicone resist material of the present invention does not contain the above photosensitive agent, and in its stead, it contains a group that possesses photosensitive to ultraviolet rays or the like, via a siloxane bonding in the principal chain. As a substance with such photosensitivity, one may mention, for example, o-nitrobenzylsilyl groups that presents alkaline solubility when it is irradiated by ultraviolet rays.
    Type: Grant
    Filed: December 8, 1986
    Date of Patent: April 18, 1989
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Yasunobu Onishi, Shuji Hayase, Rumiko Horiguchi, Akiko Hirao
  • Patent number: 4806448
    Abstract: Compounds of formula I ##STR1## in conjunction with compounds that donate acid when exposed to actinic radiation, are suitable for use as positive photoresists. In formula I, R.sup.1 and R.sup.2 are hydrogen, alkyl, aryl, cycloalkyl, aralkyl or alkaryl, R.sup.3 to R.sup.8 are hydrogen or lower alkyl, X is --O-- or --NR.sup.9 --, where R.sup.9 is hydrogen or C.sub.1 -C.sub.4 alkyl n is 0 or 1, m is 2, 3 or 4 and Q is an organic radical of valency m.The photoresists are suitable for making printing formes, printed circuits, integrated circuits or silver-free photographic films.
    Type: Grant
    Filed: November 27, 1987
    Date of Patent: February 21, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Martin Roth
  • Patent number: 4792515
    Abstract: Erasable diazotype second originals on a translucent base have become very popular because they permit correcting, deletions and additions of new information to drawings without the need to redo an entire drawing. A new barrier film composition that acts simultaneously as matrix for the diazotype coating components and controls the ease of mechanical erasure is disclosed. The second originals exhibit almost film like reprographic continuity.
    Type: Grant
    Filed: January 8, 1987
    Date of Patent: December 20, 1988
    Assignee: Andrews Paper & Chemical Co., Inc.
    Inventors: Peter Muller, Henry Mustacchi, George Schmitz
  • Patent number: 4789619
    Abstract: A positive-working radiation-sensitive mixture is described that contains (a) a radiation-sensitive compound which forms a strong acid under the action of actinic radiation, (b) a compound with at least one C--O--C bond cleavable by acid, (c) a binder which is insoluble in water but soluble in aqueous-alkaline solutions, and (d) a polymethine dye. The polymethine dyes used are hemioxonol dyes or symmetrical cyanine dyes. In the light-sensitive mixture, these dyes effect high sensitization and high image sharpness contrast which, in addition, is substantially irreversible.
    Type: Grant
    Filed: November 24, 1986
    Date of Patent: December 6, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans Ruckert, Joachim Knaul
  • Patent number: 4783390
    Abstract: A multi-color image forming material which is in the form of multiple layers on a support, and having, at least two photosensitive layers, the farthest layer from the support being the uppermost photosensitive layer, the photosensitive layers being formed from a water-soluble resin having photocrosslinking ability with diazo resin, a photosensitive water-soluble, organic solvent insoluble diazo resin, and a water dispersible coloring agent which can produce a color tone, each photosensitive layer having a coloring agent which can produce a different color tone; and at least one intermediate layer, each intermediate layer being positioned between each photosensitive layer and the next adjacent photosensitive layer, the intermediate layer being formed from a hydrophobic, water-resistant, organic solvent softenable resin.
    Type: Grant
    Filed: April 1, 1987
    Date of Patent: November 8, 1988
    Assignee: Sanyo-Kokusaku Pulp Co., Ltd.
    Inventors: Hisashi Mino, Norio Yabe, Takeshi Iijima
  • Patent number: 4777111
    Abstract: This invention relates to a composition and method for enhancing the contrast of images of an underlying photolithographic layer. A photographic element, including a photoresist layer, is applied to a substrate. The photoresist layer contains a contrast-enhancing layer including at least one light-sensitive compound capable of producing acidic photoproducts upon exposure to actinic radiation, at least one indicator dye that changes color on exposure to acidic conditions and at least one polymeric binder soluble in water or weakly alkaline aqueous solutions. The photographic element is exposed to active radiation sufficient to cause photobleaching of the contrast enhancement layer and exposure of the photoresist layer. The photographic element is exposed to actinic radiation sufficient to cause photobleaching of the contrast enhancement layer and exposure of the photoresist layer.
    Type: Grant
    Filed: March 23, 1987
    Date of Patent: October 11, 1988
    Assignee: Fairmount Chemical Company, Inc.
    Inventors: David B. Blumel, Albert S. Deutsch
  • Patent number: 4774161
    Abstract: The present invention relates to a light-sensitive composition comprising a modified polyvinyl acetal resin having a substituent possessing an acid hydrogen atom introduced into remaining hydroxy groups of a polyvinyl acetal resin in an amount of from 0.1 to 6 milliequivalents as acid content per 1 gram resin, and a diazo resin represented by the formula (I) ##STR1## wherein R.sub.1 represents a hydrogen atom, or a substituted or unsubstituted alkyl, alkoxy, hydroxy, carboxyester or carboxy group; R.sub.2 represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a phenyl group; R.sub.3 represents a hydrogen atom or an alkoxy group having 1 to 3 carbon atoms; R.sub.4 represents an alkyl group having 6 to 18 carbon atoms; n represents an integer not smaller than 2.The presensitized lithographic printing plate using the light-sensitive composition of the present invention can be developed with an alkali developer and the highlight image thereof is tough.
    Type: Grant
    Filed: January 14, 1987
    Date of Patent: September 27, 1988
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshiyuki Sekiya, Roahiaki Aoai, Kazuo Maemoto, Akihiko Kamiya
  • Patent number: 4772534
    Abstract: A light-sensitive composition containing a novel light-sensitive s-triazine compound represented by the formula (I) as a free radical-generating agent is disclosed. The s-triazine compound responds radiation in the range of the near ultraviolet to visible light, shows high sensitivity for photolysis and, therefore, the compositon has high light-sensitivity.
    Type: Grant
    Filed: September 5, 1986
    Date of Patent: September 20, 1988
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kouichi Kawamura, Hirokazu Kondo, Yoshimasa Aotani
  • Patent number: 4751166
    Abstract: This invention relates to negative photosensitized sheet contructions which, upon exposure to an actinic radiation source through a screened image, can accurately reproduce said image. The construction is useful as a color proofing film which can be employed to predict the image quality from a lithographic printing process.
    Type: Grant
    Filed: September 12, 1986
    Date of Patent: June 14, 1988
    Assignee: Hoechst Celanese Corp.
    Inventors: Stephan J. Platzer, Gabor I. Koletar
  • Patent number: 4749639
    Abstract: A photosensitive composition comprising a polymeric diazonium salt, preferably a diazonium salt polycondensation product, and a polymeric binder possessing lateral crosslinking groups represented by the formula --CH.sub.2 --OR, wherein R denotes a hydrogen atom, a lower alkyl group, a lower acyl group or a lower hydroxyalkyl group, can be used to produce printing plates which yield considerably increased print runs after being baked at temperatures of 150.degree. C. to 250.degree. C.
    Type: Grant
    Filed: February 7, 1986
    Date of Patent: June 7, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Hans-Dieter Frommeld
  • Patent number: 4741985
    Abstract: A light-sensitive composition comprising a diazonium compound and a polymer having the recurring units represented by the following general formula (I): ##STR1## wherein R.sub.1 represents a hydrogen atom or a substituted or unsubstituted alkyl group; R.sub.2 represents an unsubstituted alkyl group; R.sub.3 represents an aliphatic or aromatic hydrocarbon group having a carboxyl group; R.sub.4 represents an aliphatic or aromatic hydrocarbon group which has at least one hydroxyl or nitrile group and which may be further substituted; n.sub.1, n.sub.2, n.sub.3, n.sub.4 and n.sub.5 represent the molar percents of the respective recurring units, provided that n.sub.1 is from about 5 to about 85 mol %, n.sub.2 is from 0 to about 60 mol %, n.sub.3 is from 0 to about 20 mol %, n.sub.4 is from about 3 to about 60 mol % and n.sub.5 is from greater than 0 to about 60 mol %.
    Type: Grant
    Filed: June 6, 1986
    Date of Patent: May 3, 1988
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshiaki Aoai, Kazuo Maemoto, Akihiko Kamiya, Toshiyuki Sekiya
  • Patent number: 4737484
    Abstract: A heat-sensitive recording material is described, comprising a support having provided thereon a recording layer comprising a diazo compound and a coupling component, wherein the improvement comprises including said diazo compound and at least one compound selected from a polymerizable compound containing an ethylenically unsaturated bond therein or at least one compound capable of releasing a free radical upon exposure to light together in microcapsules.
    Type: Grant
    Filed: April 19, 1985
    Date of Patent: April 12, 1988
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Masayuki Iwasaki, Hiroshi Kamikawa, Toshimasa Usami
  • Patent number: 4737426
    Abstract: Compounds of formula I ##STR1## in conjunction with compounds that donate acid when exposed to actinic radiation, are suitable for use as positive photoresists. In formula I, R.sup.1 and R.sup.2 are hydrogen, alkyl, aryl, cycloalkyl, aralkyl or alkaryl, R.sup.3 to R.sup.8 are hydrogen or lower alkyl, X is --O-- or --NR.sup.9 --, where R.sup.9 is hydrogen or C.sub.1 -C.sub.4 alkyl, n is 0 or 1, m is 2, 3 or 4 and Q is an organic radical of valency m.The photoresists are suitable for making printing forms, printed circuits, integrated circuits or silver-free photographic films.
    Type: Grant
    Filed: May 5, 1986
    Date of Patent: April 12, 1988
    Assignee: Ciba-Geigy Corporation
    Inventor: Martin Roth
  • Patent number: 4731316
    Abstract: A photosensitive composition of this invention comprises:(a) a photosensitive diazo resin represented by the following general formula (I): ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 each represents a hydrogen atom, an alkyl or alkoxy group, R represents a hydrogen atom, an alkyl or phenyl group, X represents PF.sub.6 or BF.sub.4 and n represents a number of 1 to 200, in which a resin with the number n in the above formula being 5 or more is contained by more than 20 mol %,(b) an oleophilic high molecular weight compound with hydroxyl group and(c) a high molecular weight organic acid without hydroxyl group, and in which the content of the ingredient (c) is from 1.5 to 30% by weight based on the solid matter in said composition.The photosensitive composition of this invention can provide a photosensitive layer having high sensitivity and being excellent in storage stability and developability as well as excellent in the film strength.
    Type: Grant
    Filed: October 1, 1985
    Date of Patent: March 15, 1988
    Assignees: Mitsubishi Chemical Industries Limited, Konishiroku Photo Industry Co., Ltd.
    Inventors: Hiroshi Tomiyasu, Yoshihiro Maeda, Kiyoshi Goto, Norihito Suzuki
  • Patent number: 4729935
    Abstract: A process for the production of photographic images utilizing a photographic element comprising a transparent support and a coating on the support comprising a diazonium composition having a light absorbency of about 45% or less, and a colorant composition, said coating having a light transmission of not more than about 0.1%.
    Type: Grant
    Filed: October 18, 1985
    Date of Patent: March 8, 1988
    Assignee: Hoechst Celanese Corporation
    Inventors: John E. Walls, Major S. Dhillon
  • Patent number: 4721665
    Abstract: The invention features a lithographic composition fabricated from a process wherein an acidic novolak resin is neutralized in solution. The solution comprises a common compatible solvent with the other ingredients of the coating composition, such as a positive sensitizer, a color changing dye, and a light activated, acid-releasing compound.
    Type: Grant
    Filed: September 29, 1986
    Date of Patent: January 26, 1988
    Assignee: Polychrome Corporation
    Inventors: Thomas Dooley, James Shelnut
  • Patent number: 4705736
    Abstract: A diazotype sheet is developable solely by heat, the sheet comprising in at least one layer a heat-softenable, organic solvent-soluble resin, an acid-stabilized diazonium salt, at least one azo-coupler compound capable of reacting to form a dye, and an acid neutralizing component immobilized either by encapsulation or by coating as a separate layer with or without a binder. The sheet has incorporated therein at least one plasticizer which is either liquid at room temperature (i.e., 20.degree. to 25.degree. C.) or fusible at a temperature between room temperature and the development temperature.
    Type: Grant
    Filed: December 5, 1985
    Date of Patent: November 10, 1987
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Norman T. Notley
  • Patent number: 4687726
    Abstract: Disclosed are a novel photosensitive recording material and a method for using the recording material in the production of planographic printing plates. The recording material comprises a support and a negative-working photosensitive layer that contains a diazonium salt polycondensation product as the photosensitive compound and, in addition, a colorless inorganic pigment which is insoluble in water and organic solvents and which has an average particle diameter from 1 to 20 .mu.m. The pigment is present in a quantity from 0.01 to 2% by weight, relative to the non-volatile constituents of the layer, and is evenly distributed in the layer. Due to the pigment content, a rough layer surface is formed, which has the effect of reducing the time required for creating a vacuum in a vacuum frame into which the recording material is mounted. The presence of the pigment in the layer also produces an improved tonal rendering in the print obtained.
    Type: Grant
    Filed: May 8, 1985
    Date of Patent: August 18, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunter Schlogl, Gerhard Mack, Manfred Michel
  • Patent number: 4681833
    Abstract: A light-sensitive composition is described, containing: (A) a light-sensitive diazo compound, (B) a combination of Polymer (B-1) and Polymer (B-2), and (C) an epoxy resin. Polymer (B-1) is a polymer having the structural units of the general formulae (i), (ii) and (iii). Polymer (B-2) is a polymer having the structural units of the general formulae (iv), (v) and (vi). ##STR1## wherein R.sup.1 is a hydrogen atom or a methyl group, R.sup.2 is an unsubstituted or substituted benzyl group, a lower alkyl group, or a halogen-substituted lower alkyl group, R.sup.3 is a hydrogen atom, a lower alkyl group, or a halogen-substituted lower alkyl group, R.sup.4 is a tert- or iso-butyl group, and R.sup.5 is a lower alkyl group. This composition is a negative-type light-sensitive composition and is used to prepare a lithographic printing plate, for example. This printing plate is superior in lipophilic nature and also in mechanical properties such as abrasion resistance.
    Type: Grant
    Filed: March 7, 1985
    Date of Patent: July 21, 1987
    Assignee: Somar Corporation
    Inventors: Kohtaro Nagasawa, Kunio Morikubo
  • Patent number: 4665006
    Abstract: A photoresist composition comprised of a radiation scissionable polymeric system having organopolysiloxane segments sensitized by an onium salt is disclosed. Useful organopolysiloxane containing polymers include polysiloxane-polycarbonate block copolymers, and polyorganosiloxane polyaryl esters. The resist films produced from the photoresist compositions exhibit high sensitivity, high thermal stability and resistance to oxygen reactive ion etching which makes them desirable for dry etching processes to enable submicron resolution.
    Type: Grant
    Filed: December 9, 1985
    Date of Patent: May 12, 1987
    Assignee: International Business Machines Corporation
    Inventors: Krishna G. Sachdev, Ranee W. Kwong, Mahmoud M. Khojasteh, Harbans S. Sachdev
  • Patent number: 4661432
    Abstract: A light-sensitive, diazonium group-containing polycondensation product is described which comprises(a) an optionally substituted diphenylamine-dianzonium salt I.(b) a compound corresponding to the formula IIR.sup.4 --O--CH.sub.2 --R.sup.5 (II)whereinR.sup.4 is H, alkyl or acyl, andR.sup.5 is an optionally substituted aromatic radical, and(c) a compound corresponding to the formula IIIR.sup.6 --O--CH.sub.2 --R.sup.8 --CH.sub.2 --O--R.sup.7 (III)whereinR.sup.6 and R.sup.7 are H, alkyl, or acyl andR.sup.8 is the radical of a compound selected from the group consisting of aromatic hydrocarbons, phenols, phenolethers, aromatic thioethers, aromatic heterocyclic compounds, and organic acid amides,with the radicals resulting from compound II being directing linked to the units of the diazonium salt I.In the production of the polycondensation product, I is first condensed with II and then with III.
    Type: Grant
    Filed: January 23, 1986
    Date of Patent: April 28, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Walter Lutz, Hartmut Steppan
  • Patent number: 4659645
    Abstract: A photosensitive mixture comprised of(a) a diazonium salt polycondensation product comprising recurring units of the formulas A--N.sub.2 X and B, which units are linked by bivalent intermediate members derived from a carbonyl compound which is capable of condensation, wherein the A--N.sub.2 X units are derived from aromatic diazonium compounds that are capable of condensation with formaldehyde, and the B units are derived from compounds which are free from diazonium groups and are also capable of condensation with formaldehyde in a strongly acidic medium;(b) a compound which can be polymerized by a free-radical process;(c) a photopolymerization initiator; and(d) a polymeric binder that is insoluble in water, but soluble in organic solventscan be used in the production of photosensitive printing plates and photoresists.
    Type: Grant
    Filed: July 9, 1985
    Date of Patent: April 21, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans-Dieter Frommeld, Walter Lutz, Hartmut Steppan
  • Patent number: 4659644
    Abstract: A diazo-type thermosensitive recording material is disclosed, which comprises a support material and a thermosensitive coloring layer formed on the support material, which thermosensitive coloring layer comprises a diazonium compound, a coupler and a thermo-fusible or thermo-softening material, the coupler being a combination of a hydrazone-type coupler of the formula of R.sup.1 --NH--N.dbd.CH--R.sup.2 (wherein R.sup.1 and R.sup.2 are defined in detail in the specification) and a two-valence metal compound capable of chelating with the coupled product produced by the coupling of the diazonium compound and the hydrazone-type coupler.
    Type: Grant
    Filed: December 19, 1984
    Date of Patent: April 21, 1987
    Assignee: Ricoh Company, Ltd.
    Inventors: Takayuki Hoshina, Michihisa Takahashi, Masanori Rimoto, Masanaka Nagamoto
  • Patent number: 4656115
    Abstract: An improved vesicular matrix prepared by the emulsion polymerization of methacrylonitrile, either alone or with a small amount of comonomer, in the presence of a cationic emulsifier. The resulting polymer or copolymer can be used alone, or the polymer or copolymer may be blended with a small amount of a highly incompatible polymer or copolymer, to provide an improved vesicular matrix.
    Type: Grant
    Filed: November 22, 1985
    Date of Patent: April 7, 1987
    Assignee: James River Graphics, Inc.
    Inventors: Ahmad Arfaei, Everett W. Bennett
  • Patent number: 4654291
    Abstract: An improved vesicular matrix prepared by employing regulated inner incompatibility to produce enhanced nucleation. The inner incompatibility is produced by copolymerizing a first monomer with a small amount of a second monomer wherein a homopolymer of the second monomer would be incompatible with a polymer of the first monomer, or by blending a first polymer or copolymer with a small amount of a highly incompatible second polymer or copolymer.
    Type: Grant
    Filed: November 22, 1985
    Date of Patent: March 31, 1987
    Assignee: James River Graphics
    Inventor: Jan B. Suchy
  • Patent number: 4652512
    Abstract: This invention provides a heat-sensitive recording material comprising a substrate and a heat-sensitive recording layer which is formed over the substrate and which contains a diazonium salt, a coupler and at least one of specific heat-fusible basic amidine and diamidine compounds in which the nitrogen atom(s) of ##STR1## moiety(moieties) has(have) a substituent and the nitrogen atom(s) or ##STR2## moiety(moieties) has(have) at least one substituent, the substituent being independently selected from the group consisting of phenyl, naphthyl, phenyl-C.sub.1 -C.sub.4 alkyl and naphthyl-C.sub.1 -C.sub.4 alkyl, each optionally substituted with C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, phenyloxy, nitro or halogen, and in which amidine compounds are other than formamidines. The heat-sensitive recording material is especially excellent in storage stability.
    Type: Grant
    Filed: January 29, 1986
    Date of Patent: March 24, 1987
    Assignee: Kanzaki Paper Manufacturing Company, Limited
    Inventors: Katsuhiko Ishida, Masaharu Nojima, Tosaku Okamoto
  • Patent number: 4650740
    Abstract: A heat-sensitive recording material is described, comprising a support having provided thereon a recording layer comprising a binder containing a diazonium compound and a coupling component, said diazonium compound being a diazonium salt represented by formula (I)ArN.sub.2.sup.+ X.sup.- (I)wherein Ar represents a substituted or unsubstituted aromatic moiety; and X.sup.- represents an acid anion containing an alkyl group having three or more fluorine atoms.
    Type: Grant
    Filed: September 13, 1984
    Date of Patent: March 17, 1987
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshimasa Usami, Toshiharu Tanaka, Fumiaki Shinozaki
  • Patent number: 4650738
    Abstract: This invention relates to negative photosensitized sheet constructions which, upon exposure to an actinic radiation source through a screened image, can accurately reproduce said image. The construction is useful as a color proofing film which can be employed to predict the image quality from a lithographic printing process.
    Type: Grant
    Filed: October 22, 1984
    Date of Patent: March 17, 1987
    Assignee: American Hoechst Corporation
    Inventors: Stephan J. W. Platzer, Gabor I. Koletar
  • Patent number: 4645730
    Abstract: The lithographic printing plate of the invention comprises a substrate having a hydrophilic surface, a coating on said surface of a light sensitive material (e.g., a water soluble diazo) and a top coating of discrete, oleophilic resin particles (e.g., an emulsion polymer), the resin particle coating being:(a) transparent to actinic light;(b) sufficiently permeable to allow a developer for the light sensitive material to penetrate through to the underlying light sensitive coating;(c) insoluble in said developer;(d) capable of being coalesced in situ after the plate is imaged and developed.
    Type: Grant
    Filed: September 17, 1984
    Date of Patent: February 24, 1987
    Assignee: Howard A. Fromson
    Inventors: Howard A. Fromson, Robert F. Cracia
  • Patent number: 4631245
    Abstract: Disclosed is a photosensitive composition which comprises a diazonium salt polycondensation product and, as the binder, a reaction product of an intramolecular anhydride of an organic polycarboxylic acid with a polymer containing hydroxyl groups, which does not contain any further functional groups which are capable of reaction with acid anhydrides. The composition is suitable for use in the production of printing plates and photoresists. It can be developed with neutral or alkaline aqueous solutions and yields printing plates having a good ink receptivity and producing large print runs.
    Type: Grant
    Filed: February 4, 1985
    Date of Patent: December 23, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Georg Pawlowski
  • Patent number: 4617250
    Abstract: A light-sensitive composition for use with lithographic printing plates is described which comprises (1) a light-sensitive, organic solvent soluble and substantially water-insoluble diazo resin which is the reaction product of a water-soluble, light-sensitive condensate of an aromatic diazonium compound and an organic condensing agent with a halogenated Lewis acid or a salt thereof, (2) a substantially water-insoluble, film forming organic high-molecular weight compound having an acid value of from 10 to 200, (3) a polynuclear aromatic sulfonic acid or a salt thereof, and (4) a salt-forming organic dye compound.
    Type: Grant
    Filed: June 1, 1984
    Date of Patent: October 14, 1986
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Eiji Nakakita, Akinobu Koike, Toshiyuki Sekiya, Hiroshi Misu, Nobuyuki Kita
  • Patent number: 4614701
    Abstract: A photocurable resin composition comprising(A) a copolymer composed of, as structural units,(a) 20 to 70% by weight of a hydroxyl group-containing acrylic monomer unit represented by the following formula ##STR1## wherein R.sub.1 and R.sub.2, independently from each other, represent a hydrogen atom, a methyl group or an ethyl group and n is 1, 2 or 3, and(b) 5 to 80% by weight of a nitrogen-containing acrylic monomer unit represented by the following formula ##STR2## wherein R.sub.3 represents a hydrogen atom or a methyl group, X represents 0 or NH, R.sub.4 represents a linear or branched alkylene group having 2 or 3 carbon atoms, R.sub.5, R.sub.6 and R.sub.7, independently from each other, represent a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms and Y.sup..crclbar. represents an anion of an acid, and(B) a diazo compound or an azide compound.
    Type: Grant
    Filed: September 28, 1984
    Date of Patent: September 30, 1986
    Assignee: Sekisui Fine Chemical Co., Ltd.
    Inventors: Hirofumi Mori, Hitoshi Hori