US3743505A - Direct-print process utilizing photosensitive polyacetylenic amine salts containing carboxylate moieties - Google Patents

Direct-print process utilizing photosensitive polyacetylenic amine salts containing carboxylate moieties Download PDF

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US3743505A
US3743505A US00153059A US3743505DA US3743505A US 3743505 A US3743505 A US 3743505A US 00153059 A US00153059 A US 00153059A US 3743505D A US3743505D A US 3743505DA US 3743505 A US3743505 A US 3743505A
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polyacetylenic
image
crystals
radiant energy
photosensitive
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M Bloom
S Fico
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Eastman Kodak Co
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Eastman Kodak Co
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/025—Non-macromolecular photopolymerisable compounds having carbon-to-carbon triple bonds, e.g. acetylenic compounds
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/143—Electron beam
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/167—X-ray
    • Y10S430/168—X-ray exposure process

Definitions

  • this application relates to photosensitive crystalline polyacetylenic compositions of matter. More particularly, it relates to certain crystalline radiation-sensitive polyacetylenic compounds containing at least one ammonium carboxylate moiety, and the preparation and use thereof.
  • the photosensitive polyacetylenic compounds taught in the art contain a minimum of two acetylenic linkages as a conjugated system (i.e., -CEC-CEC-) and, with only a few exceptions, carbon atoms in alpha positions to the acetylenic carbon atoms, i.e., those carbon atoms directly connecting to the acetylenic carbon atoms, are bonded directly only to carbon and/or hydrogen atoms.
  • photosensitive polyacetylenic compositions of matter encompass diynes, triynes, tetraynes, higher polyynes and numerous derivatives and related compounds thereof of various chemical classes ranging from hydrocarbon compounds to acids, esters, diols, to still other compounds of other chemical classifications containing numerous and varied organic radicals stemming from the conjugated acetylenic carbon atoms.
  • 9,l1-eicosa diynedioic acid and 10,12-docosadiynedioic acid are reported by Black et al., J. Chem. Soc. (1953), 1787, 1790, 1791, as byproducts of coupling reactions; 9,11-eicosadiynedioic also is taught by Seher in Fette u. Seifen, 55 (1953), and 10,12-docosadiynedioic acid also is taught by Seher in Fette u. Seifen, 55 (1953), 95, and in Annalen, 589, 222.
  • Exemplary of such acids and esters are 7,9-hexadeca diynedioic acid, 8,10-octadecadiynedioic acid, 9,1l-eicosadecadiynedioic acid, 10,12-d0cosadiynedioic acid, 11,13- tetracosadiynedioic acid, 12,14-hexacosadiynedioic acid, 13,15-octacosadiynedioic acid, 14,16 triacontadiynedioic acid, 15,17-dotriacontadiynedioic acid, 15,17-tetratriacontadiynedioic acid, and 16,18-hexatriacontadiynedioic acid; and each of the monomethyl, monoethyl, and monopropyl esters thereof.
  • amine salt derivatives of this invention are those having the general formula wherein n is an integer greater than 1;
  • x and y are each integers from 0 to 10;
  • A is selected from ammonium and substituted ammonium groups, i.e. NH R, NH RR NHRR R NRR R R B is a hydrogen-bonding group selected from the group consisting of CH or substituted methyl group, C00 COOR, CONHR CONHNHR CONHCONHR R' NHCOO, and R OOCNH;
  • R, R R R are the same or different, and may be H, alkyl of from 1 to 15 carbon atoms, substituted alkyl, or aryl;
  • R may be H or lower alkyl
  • R may be an alkyl or substituted alkyl of from 3 to 10 carbon atoms, such as hydroxy, polyhydrody, amino, substituted amino, alkylthio, or methoxy substituted alkyl;
  • R may be alkyl or phenyl
  • R may be alkyl or substituted alkyl of from 1 to 8 carbon atoms, a phenyl group, or a substituted phenyl.
  • Preferred amine salts are those in which B is an amide radical, particularly those containing hydroxy, carboxy,
  • preferred amine salts are those which the ammonium carboxylate moiety contains an alkyl substitution, e.g.
  • R is an alkyl or substituted alkyl of from 3 to 6 carbon atoms.
  • the reaction causes the fluid slurry to be converted to a thick paste which is stirred with ether, and the mixture then filtered to separate unreacted starting material from the insoluble product (28 g.)
  • the hexylammonium compound is recrystallized from 125 ml. of ethanol, chilling in an ice bath to obtain a white solid, M.P. 9294 C.
  • EXAMPLE 2 e oannvno o orrmczozc cnmo 0 0 [Nmcrm] Propylammonium 20- (N-propylcarbamoyl) 9,1 l-eicosadiynel-carboxylate A mixture of 9.4 gr. (0.025 mole, 376.59) of monomethyl ester of 10,12-docosadiynedioic acid and 8.9 g. (0.15 mole, 59.11) of propylamine is kept for two days at room temperature. The pasty slurry is stirred with diethyl ether and the solid product filtered off. Recrystal- 0 lization from an ethanol-ether mixture yields the pure amine.
  • Acid treatment of the amine salt of the amide-substituted carboxylic acid yields the amide-substituted carboxylic acid, the amine salt being destroyed.
  • This carboxylic acid can in turn be treated with a different amine to again form an amine salt of an amidesubstituted carboxylic acid.
  • the amine residue in the amide and in the amine salt are different.
  • Each crystalline polyacetylenic compound for which a specific example of preparation already has been presented herein is photosensitive in that upon exposure to as least one form of radiant energy, particularly ultraviolet radiation, it will undergo a visible color change.
  • a semiquantitive determination and comparison of the photosensitive response of various prepared crystalline polyacetylenic compounds of the specific examples can be made as follows: The polyacetylenic compound in an organic solvent is flowed onto a white surface, such as that of a white filter paper or white filing card, and solvent evaporated to leave an adhered deposit of the crystalline polyacetylenic compound. The deposited crystalline polyyne compound then is exposed to radiant energy in the ultraviolet range, and the density of the colored photoproduct measured.
  • Radiant energy is intended to include numerous variant forms of radiant energy encompassing not only the ultraviolet and visible regions (i.e., actinic radiation) and infrared region of the electromagnetic spectrum, but also electron beam radiation such as is developed by cathode ray guns, also gamma rays, X-rays, beta rays, electrical corona discharge, and other forms of corpuscular and/ or wave-like energy generally deemed to be radiant energy.
  • the various individual crystalline polyacetylenic compositions disclosed generally are not responsive to all forms of radiant energy, but selectively respond to at least one or more of the several variant forms of radiant energy.
  • a photosensitive image-receptive element comprising a carrier means which serves to position fixedly crystals of the photosensitive crystalline polyacetylenic composition of matter.
  • the carrier means functions to hold individual crystals in fixed position in relation to other crystals so that the element whether, unexposed and exposed, can be handled and moved without displacement and or change in positions of crystals with respect to each other.
  • the element can be moved, rotated, turned over, lifted, and subjected to like physical handling, and, because of the carrier means as a component thereof, be of practical utility for many diverse image-recording applications.
  • the carrier means can be in any of several diverse embodiments so long as it functions to hold individual crystals substantially in fixed position in relation to other crystals.
  • the carrier means comprise a binder material, such as a natural or synthetic plastic, resin, colliod or gel and the like wherein the crystals of the photosensitive crystalline polyacetylenic compositions of matter are dispersed therein and held in fixed position thereby.
  • the polyyne composition is mixed as a dope, solution, emulsion, dispersion or the like with the binder material and then processed to provide solid films, sheets, coatings and the like containing dispersed crystals of the photosensitive crystalline polyacetylenic composition of matter.
  • one embodiment of the image-receptive element is a solid sheet, film or the like comprising a binder material as a dispersing medium to position fixedly therein dispersed crystals of the photosensitive crystalline polyacetylenic composition.
  • Another embodiment of the element is a substrate material or body to which adheres a film, coating, or the like of the binder material having the dispersed crystals therein.
  • Useful substrate materials include paper sheet, glass sheet, plastic film, and other conventional and suitable photographic quality substrate materials.
  • Still an additional embodiment of the element can comprise the substrate material having adhered thereto a binder-free coating of crystals of the photosensitive crystalline polyacetylenic composition of matter.
  • element embodiments can include a coating of a suitable quality photographic coating material on one or more surfaces and interfaces of the various element embodiments.
  • element embodiments can comprise the polyyne crystals and a support means of any of various combinations of the several foregoing components and still other components apparent to those in the art, so long as the carrier means fixedly positions the photosensitive crystalline polyacetylenic composition.
  • Exemplary substrate materials of utility as components for the carrier means include: vitreous materials, such as glass, glazed ceramics, porcelain, etc.; fibrous materials,
  • the base or substrate material may be transparent, translucent or opaque to the particular radiant energy to which the employed photosensitive crystalline polyacetylene compound is sensitive. It is selected with due consideration of the intended usage of the imaged element and of the specific radiant energy and technique to be employed in the particular image-recording application. For example, where the imaging technique requires transmission of ultraviolet radiant energy through the substrate material to expose the polyacetylenic crystals, the substrate should possess such a transmission characteristic and may be a cellulose acetate butyrate, cellulose acetate, polyvinyl alcohol, polyvinyl butyral or other suitable transparency.
  • the base or substrate material may be adhered directly to the binder-free or binder-dispersed photosensitive crystals, or indirectly adhered, if desired, by a subbing layer or coating on the substrate material for any of several purposes, e.g., to alter the substrate transmission of the radiant energy, to change the substrates reflectivity of the radiant energy, to modify adherence to the substrate material and for other reasons.
  • a subbing layer or coating on the substrate material for any of several purposes, e.g., to alter the substrate transmission of the radiant energy, to change the substrates reflectivity of the radiant energy, to modify adherence to the substrate material and for other reasons.
  • subbing layer is selected with due regard to the specific radiant energy and technique to be employed in the particular image-recording application. Subbing layers for various photographic purposes and methods of coating substrate materials with the same are well known.
  • the element is a flat film, sheet, plate or the like so as to present a flat surface upon which radiant energy may be directed.
  • curved-surfaced and other than flatsurfaced elements are not excluded.
  • binder materials of utility as components for the carrier means include: natural and synthetic plastics, resins, Waxes, colloids, gel and the like including gelatins, desirably photographic-grade gelatin, various polysaccharides including dextran, dextrin, hydrophyllic cellulose ethers and esters, acetylated starches, natural and synthetic waxes including paraflin, beeswax, polyvinylacetates, polymers of acrylic and methacrylic esters and amides, hydrolyzed interpolymers of vinyl acetate and unsaturated addition polymerizable compounds such as maleic anhydride, acrylic and methacrylic esters and styrene, vinyl acetate polymers and copolymers and their derivatives including completely and partially hydrolyzed products thereof, polyvinyl acetate, polyvinyl alcohol, polyethylene oxide polymers, polyvinylpyrrolidine, polyvinyl acetals including polyvinyl acetaldehyde acetal, polyvin
  • binder material As is well known in the art in the preparation of smooth uniform continuous coatings of binder materials, there may be employed therewith small amounts of such conventional coating aids as viscosity controlling agents, leveling agents, dispersing agents, and the like.
  • the particular binder material employed is selected with due regard to the specific radiant energy and technique to be employed in the particular image-recording application and invariably is a binder material permitting substantial transmission of that specific radiant energy to be employed.
  • the binder material is a nonsolvent, or possesses only limited solvating properties, for the photosensitive polyyne so that the polyyne is capable of existence in its crystalline form therein.
  • Well-known sources, lenses, and optical systems, camera arrangements, focusing and projection systems and the like for the various forms of radiant energy are used in employing the image-receptive element in the varied image-forming applications, such as specimen photography, pattern making, reproduction of written, printed, drawn, typed, and like matter, and the recording of line graphical images by an impinging pointed beam of the radiant energy on the element with either or both the element and pointed beam guided or traveling to trace the image.
  • the resultant images are directly formed print-out images in that they can be seen by the human eye to be a visibly distinctly different color than unirradiated crystals of the element.
  • the photosensitive image-receptive element may be used in image-forming systems based on transmissionexposure techniques and reflex-exposure techniques.
  • stencils of a material substantially nontransmissive of the radiant energy may be laid on the image-forming element with the cutout portion of the stencil allowing the applied radiant energy to strike the element according to the desired image or images. If desired, the stencil need not contact the element with the radiant energy being projected to pass through the cut-out portion of the stencil to strike the element.
  • the element also can be exposed by contact or projection techniques through a two-tone image or process transparency, i.e., a process negative or positive (i.e.
  • an image-bearing transparency consisting of areas transmissive and opaque to the radiant energy such as of a so-called line of halftone negative or positive-type transparency) or a continuous tone negative or positive.
  • an object, Whose image is to be obtained may be placed between the radiant energy source and the element and the radiant energy striking the element will be of an image pattern dependent on the radiant energy absorption and transmission characteristics of the particular object.
  • Reflex-exposure techniques are applicable. For example, by ultraviolet reflecting optic techniques, the ultraviolet sensitive image-receptive elements may be used to make photocopies of printed or typed copy.
  • flex-exposure techniques are particularly useful for making office copies from materials having messages on both sides of a. page, for making images of specimens and objects, and for reproducing messages and the like found on materials not having radiant energy transmissive properties conductive to transmission-exposure techniques.
  • the image elements are to be retained for lengthy periods, they are stored, as in an envelope or opaque container, in a manner excluding any stray irradiation of radiant energy of a form photosensitively effecting the element.
  • This may be effectively accomplished by overcoating the imaged element with a layer of material which absorbs radiation to which the element is photosensitive.
  • an ultraviolet absorbing layer may be coated over the imaged element.
  • the initially imaged element may be fixed or converted to a more stable image state. In fixing the unexposed photosensitive crystalline polyyne is placed in a form whereat it is no longer substantially photosensitive, as by solvating it in the binder, changing it from crystalline to liquid state, or washng it out from the element, and the like. In conversion, the initial irradiation induced color is transformed to another distinctly different color, which is relatively stable as to exposure to the initial form of radiant energy inducing the image formation.
  • a particularly convenient manner to effect a color transformation of the initially induced image is to carefully heat the imaged element to an appropriate elevated temperature, generally between 5-20 C. less than the melting point of the nonirradiated crystalline photosensitive polyyne, whereat the initial radiant-energy induced color-transformer crystals and crystal portions transform to another distinctly diiferent visible color. Temperatures approximating and higher than the melting point of the nonirradiated photosensitive crystalline polyyne will effect a color transformation of the initial radiant-energy induced color polyyne crystals, but in so doing, there may be some loss in sharpness of the image with some blurring and roughing of the image border or periphery.
  • Another manner for effecting color transformation of the blue-colored image is exposure to a solvent for the unexposed polyyne.
  • An exposure for about 10 to 15 seconds at an elevated temperature from about 5 to 10 C. lower than employable for heat fixing generally is satisfactory.
  • Methanol, ethanol, toluene, diethyl ether, butyl acetate, carbon tetrachloride, acetone, 2-butoxyethan0l, and like solvents are useful and water vapor and aqueous solutions, such as aqueous hydrochloric acid with water soluble polyyne derivatives. Other useful solvents also will be apparent.
  • An advantage of the element, having the image thereof in another distinctly different color than the radiationinduced colored image, is that this other color may be more susceptible to providing copies with good contrast when prints, negatives, and the like of this image are made by conventional silver halide photographic techniques.
  • image recording elements utilizing radiation sensitive polyynes are prepared by fixing the crystalline polyyne on a surface. This may be done, for example, by coating a dispersion of the polyyne in a polymer matrix on a suitable support, or by coating a solution of the polyyne in a polymer solution and allowing the polyyne to crystallize upon solvent evaporation, or by applying a solution of a polyyne to a paper surface and allowing the polyyne to crystallize upon the fibers, or by coating a dispersion of a water immiscible polyyne solution in an aqueous binder and allowing evaporation to form polyyne crystals in the binder matrix.
  • the non-crystalline dispersion is then coated with a 0.004" coating blade on a poly (ethylene terephthalate) film containing a vinylidene chloride (80% )-acrylonitrile (14% )-acrylic acid (6%) terpoly mer subbing layer overcoated with a cuprous iodide-cellulose nitrate conductive layer of the type described in Trevoy, U.S. Pat. 3,245,833.
  • the coating is chill-set and allowed to dry at room temperature. Electron micrographic show a crystal size range of from about 0.2 to about 4.0 microns with an average particle size in the coating of about 0.8 micron.
  • n is an integer greater than 1;
  • x and y are each an integer from 0 to 10;
  • A is NRR R R wherein R, R R and R are H, alkyl of from 1 to 15 carbon atoms, aryl or substituted alkyl having substituents chosen from the group consisting of hydroxy, amino, carboxy, and methoxy substitutents;
  • B is selected from the group consisting of C00 COOR CONHR CONHNHR, and R' NI-ICOO radicals, wherein R is H or lower alkyl, R is an alkyl or substituted alkyl of from 3 to 8 R is an alkyl or substituted alkyl of from 3 to 8 carbon atoms in which the substitutents are chosen from the class consisting of hydroxy, amino, alkylthio or methoxy substituents, R is alkyl or phenyl, and R is an alkyl of from 1 to 8 carbon atoms or phenyl.
  • said polyacetylenic compound is an amine salt of a polyacetylenic alkylamide.
  • an imagereceptive element comprised of a carrier means fixedly positioning discrete crystals of a photosensitive crystalline polyacetylenic compound having a minimum of two acetylenic linkages as a conjugated system
  • process comprises: exposing the crystals of said element to radiant energy in a pattern of the image to be created with the employed radiant energy exposure inducing a visual distinct color change in portions of crystals irradiated therecompound is hexylammonium 20-(N-hexylcarbamoyl)- 9,1 l-eicosadiyne-l-carboxylate.
  • polyacetylenic compound is propylammonium 20-(N-propylcarbamoyl)- 9,1 l-eicosadiynel-carboxylate.
  • polyacetylenic compound is 3-hydroxypropylammonium 20- [N-(3- hydroxypropyl)-carbamoyl] 9,11 eicosadiyne l-carboxylate.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
US00153059A 1971-06-14 1971-06-14 Direct-print process utilizing photosensitive polyacetylenic amine salts containing carboxylate moieties Expired - Lifetime US3743505A (en)

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JP (1) JPS555100B1 (cs)
CH (1) CH542461A (cs)
DE (1) DE2228258C3 (cs)
FR (1) FR2141851B1 (cs)
GB (1) GB1391009A (cs)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4389217A (en) * 1979-05-11 1983-06-21 Allied Corporation Integrated time-temperature or radiation-dosage history recording device
US4615962A (en) * 1979-06-25 1986-10-07 University Patents, Inc. Diacetylenes having liquid crystal phases
US4767826A (en) * 1985-07-18 1988-08-30 Polytechnic Institute Of New York Radiation-sensitive polymers
US4788151A (en) * 1986-09-29 1988-11-29 Lifelines Technology, Inc. Metal complexed acetylenic compounds useful as environmental indicating materials
US4789637A (en) * 1986-09-29 1988-12-06 Lifelines Technology, Inc. Acid complexed acetylenic compounds useful as environmental indicating materials
US4933114A (en) * 1980-08-11 1990-06-12 Eastman Kodak Company Polyacetylenic lipids, radiation-sensitive compositions, photographic elements and processes relating to same
US5095134A (en) * 1990-10-23 1992-03-10 Isp Investments Inc. Thermochromic diacetylene ethers containing ester or urethane groups
US5420000A (en) * 1990-04-09 1995-05-30 Jp Laboratories, Inc. Heat fixable high energy radiation imaging film
US5672465A (en) * 1990-04-09 1997-09-30 Jp Laboratories, Inc. Polyethyleneimine binder complex films
US5731112A (en) * 1996-05-23 1998-03-24 Isp Investments Inc. Processless diacetylenic salt films capable of developing a black image
US20090253870A1 (en) * 2001-08-27 2009-10-08 Akikazu Matsumoto Photoresponsive polymer,built-up type diacetylene polymer, crystal of ammonium carboxylate, and method of manufacturing them

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2553531B1 (fr) * 1983-10-14 1995-12-29 Canon Kk Monomere photopolymerisable pour milieu d'enregistrement optique et milieu le contenant
US4705742A (en) * 1985-09-23 1987-11-10 Gaf Corporation Processless multicolor imaging
DE102014223271B4 (de) 2014-11-14 2021-07-29 Bayerische Motoren Werke Aktiengesellschaft Verfahren zur Herstellung eines Faserverbundformteils, Faserverbundformteil und Verwendung fotografischer Gelatine

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4389217A (en) * 1979-05-11 1983-06-21 Allied Corporation Integrated time-temperature or radiation-dosage history recording device
US4615962A (en) * 1979-06-25 1986-10-07 University Patents, Inc. Diacetylenes having liquid crystal phases
US4933114A (en) * 1980-08-11 1990-06-12 Eastman Kodak Company Polyacetylenic lipids, radiation-sensitive compositions, photographic elements and processes relating to same
US4767826A (en) * 1985-07-18 1988-08-30 Polytechnic Institute Of New York Radiation-sensitive polymers
US4788151A (en) * 1986-09-29 1988-11-29 Lifelines Technology, Inc. Metal complexed acetylenic compounds useful as environmental indicating materials
US4789637A (en) * 1986-09-29 1988-12-06 Lifelines Technology, Inc. Acid complexed acetylenic compounds useful as environmental indicating materials
US5672465A (en) * 1990-04-09 1997-09-30 Jp Laboratories, Inc. Polyethyleneimine binder complex films
US5420000A (en) * 1990-04-09 1995-05-30 Jp Laboratories, Inc. Heat fixable high energy radiation imaging film
US5095134A (en) * 1990-10-23 1992-03-10 Isp Investments Inc. Thermochromic diacetylene ethers containing ester or urethane groups
US5731112A (en) * 1996-05-23 1998-03-24 Isp Investments Inc. Processless diacetylenic salt films capable of developing a black image
US6177578B1 (en) 1996-05-23 2001-01-23 Isp Investments Inc. Processless diacetylenic salt films capable of developing a black image
US20090253870A1 (en) * 2001-08-27 2009-10-08 Akikazu Matsumoto Photoresponsive polymer,built-up type diacetylene polymer, crystal of ammonium carboxylate, and method of manufacturing them
US7750084B2 (en) 2001-08-27 2010-07-06 Japan Science And Technology Agency Photoresponsive polymer, built-up type diacetylene polymer, crystal of ammonium carboxylate, and method for manufacturing them
US7981968B2 (en) 2001-08-27 2011-07-19 Japan Science And Technology Agency Photoresponsive polymer, built-up type diacetylene polymer, crystal of ammonium carboxylate, and method of manufacturing them

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FR2141851B1 (cs) 1978-03-03
FR2141851A1 (cs) 1973-01-26
DE2228258B2 (de) 1975-04-24
DE2228258C3 (de) 1975-12-11
DE2228258A1 (de) 1973-01-04
JPS555100B1 (cs) 1980-02-04
GB1391009A (en) 1975-04-16
CH542461A (fr) 1973-09-30

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