WO1982002689A1 - Procede de formation d'images en couleurs sur des materiaux textiles et films photosensibles utilises dans ce procede - Google Patents

Procede de formation d'images en couleurs sur des materiaux textiles et films photosensibles utilises dans ce procede Download PDF

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Publication number
WO1982002689A1
WO1982002689A1 PCT/US1982/000176 US8200176W WO8202689A1 WO 1982002689 A1 WO1982002689 A1 WO 1982002689A1 US 8200176 W US8200176 W US 8200176W WO 8202689 A1 WO8202689 A1 WO 8202689A1
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WIPO (PCT)
Prior art keywords
photosensitive
layer
presensitizing
photosensitive layer
textile material
Prior art date
Application number
PCT/US1982/000176
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English (en)
Inventor
Jean J Robillard
Original Assignee
Jean J Robillard
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Jean J Robillard filed Critical Jean J Robillard
Priority to AU82719/82A priority Critical patent/AU8271982A/en
Publication of WO1982002689A1 publication Critical patent/WO1982002689A1/fr

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    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C5/00Photographic processes or agents therefor; Regeneration of such processing agents
    • G03C5/18Diazo-type processes, e.g. thermal development, or agents therefor
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00Photosensitive materials
    • G03C1/76Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/7642Photosensitive materials characterised by the base or auxiliary layers the base being of textile or leather

Definitions

  • This invention relates to a process for forming photographic prints on textiles by a heat transfer process from a light-sensitive film which has previously been exposed to an original image to be printed, and to a novel light-sensitive film to be used in the process. More particularly, this invention relates to a process for forming monochromatic or polychromatic photographic prints on textile material by presensitizing the textile with at least one diazonium coupler compound and developing the image on the presensitized textile by transferring at least one diazonium compound from a light-sensitive paper which has been imagewise exposed through a positive transparency of the image to be printed by placing the exposed photosensitive film in contact with the presensitized textile and heating the assembly to transfer the color-forming reactants from the film to the presensitized textile under conditions which will allow the diazo coupling reaction to proceed; and to a novel light-sensitive film capable of releasing the color-forming reactants contained therein by a heat transfer process.
  • a still further object of the present invention is to provide a photosensitive paper which can be exposed by conventional photographic techniques and which allows the exposed original to be printed on textiles by a heat transfer method.
  • Still yet another object of the invention is to provide a transfer paper which presensitizes the surface of textile material to receive and develop a photographic image of high quality transferred from a photosensitive paper which has been previously exposed to the original of the image to be reproduced by conventional photographic techniques and equipment.
  • a film substrate having a release layer on one surface thereof, and (2) a photosensitive layer coated on the release layer wherein the photosensitive layer comprises
  • the presensitizing coating layer is applied onto the textile by providing a presensitizing film comprising (1) a film substrate having a release layer on one surface thereof and (2) a presensitizing layer on the release layer wherein the presensitizing layer includes at least one diazonium coupler compound uniformly dispersed in an organic binder; bringing the presensitizing layer of the presensitizing film into contact with the textile material; heating the assembled presensitizing film and textile material to transfer the diazonium coupler compound to the textile material; and removing the presensitizing film from the textile material.
  • a presensitizing film comprising (1) a film substrate having a release layer on one surface thereof and (2) a presensitizing layer on the release layer wherein the presensitizing layer includes at least one diazonium coupler compound uniformly dispersed in an organic binder; bringing the presensitizing layer of the presensitizing film into contact with the textile material; heating the assembled presensitizing film
  • the process is also capable of forming a polychromatic image of the original on the textile material which is based upon the formation of separate images from positive transparencies capable of color separation for each of the primary colors, red, blue, and yellow.
  • the polychromatic image on the textile material is formed by repeating steps (A) through (E) three times, wherein in the first repetition, the presensitizing coating layer includes a first diazonium coupler compound capable of forming one of the three primary colors, such as red, and exposing the photosensitive layer through a positive transparency capable of color separation for the particular color of the diazonium coupler compound, and then repeating the steps by applying a presensitizing coating layer containing a second diazonium coupler compound capable of forming one of the two remaining primary colors, such as blue, and exposing the photosensitive layer through a positive transparency capable of color separation for the second selected primary color and, thereafter, repeating the steps by applying a presensitizing coating layer containing a third diazonium coupler
  • the present invention also provides a novel photosensitive film capable of use in the heat transfer printing process.
  • the film includes (1) a film substrate comprising (a) a paper base, and (b) a coating of a release layer on one surface of the paper base; and (2) a coating of a photosensitive layer on the release layer.
  • the photosensitive layer includes a (a) light-sensitive aryldiazonium compound, and (b) a heat-activatable pH adjusting agent uniformly dispersed in an organic binder which softens at the temperature of the heat transfer step.
  • the photosensitive composition also includes one or more of a stabilizer, an antioxidant, and a non-ionic surfactant.
  • the photosensitive film has the property that when the photosensitive layer is imagewise exposed to actinic radiation and then heated to a temperature higher than the softening temperature of the organic binder, the color-forming reactants of the photosensitive layer can be transferred to another surface for development on the other surface.
  • the present invention also provides a transfer paper for presensitizing the other surface, preferably, a textile fabric material.
  • the presensitizing transfer paper includes a paper base which includes a release layer coated on one surface of the paper base and a heat transferable presensitizing layer coated on the release layer which includes one or more diazonium coupler compounds and a heat softenable organic binder.
  • Figure 1a, 1b, and 1c illustrate the sequence of presensitizing film transfer paper according to the invention with a manually operated heat transfer press
  • Figure 2 schematically illustrates, in side elevation, an exposure box for exposing a photosensitive film transfer paper according to the invention to a photographic positive transparency;
  • Figure 3a, 3b, and 3c illustrate the sequence of steps for contacting the presensitized textile material with the exposed photosensitive film transfer paper using the manually operated heat transfer press;
  • Figure 4 schematically illustrates a continuous process according to the invention for forming a monochromatic colored image on a textile web;
  • Figure 5 schematically illustrates a continuous process, similar to figure 4, for forming a polychromatic colored image on a textile web.
  • the high resolution heat transfer printing process of the invention is made possible by the provision of a photosensitive film which permits the aryldiazonium compound to be accurately transferred from the exposed photosensitive film to the presensitized textile material along with a heat-activatable pH-adjusting agent such that transfer and development of the colored image take place simultaneously to faithfully reproduce the original image.
  • the photosensitive film includes a film substrate and a photosensitive layer.
  • the film substrate includes a release layer on at least one surface thereof.
  • the function of the release layer is to permit transfer of the photosensitive layer upon application of sufficient heat to the photosensitive film.
  • the film substrate is preferably paper such as bleached kraft paper which has been coated with an appropriate releasing agent.
  • Suitable materials for the release agent include, for example, polyethylene, silicone polymers and metal soaps. Polyethylene and the silicone polymers are the preferred materials of the release layer.
  • the mechanism by which the release layer functions is not entirely clear, but it is believed that the release layer softens upon the application of heat and, in that condition, has a lower degree of adhesion to the photosensitive layer coated thereon than between the photosensitive layer and textile material.
  • the release layer is not itself transferred to the textile fabric, but if a small amount of the release layer is transferred, it does not interfere with the subsequent diazo coupling reaction. Furthermore, any release material so transferred will be removed upon laundering of the printed textile material.
  • paper is the preferred film substrate because of its low cost and flexibility, other materials which can withstand the temperatures imposed during the heat transfer, typically in the range of from about 250° to 450oF, and which are chemically resistant to the release layer and photosensitive layer can also be used.
  • Papers with suitable release layers are known and are commercially available, such as the product TRANS-EZE, a trademarked product of Kimberly-Clark Co. Papers with release layers are also used in the sublimation heat transfer processes described above.
  • the photosensitive layer is formed from a composition which includes an intimate mixture of a lightsensitive aryldiazonium compound of the type conventionally incorporated in diazotype materials and a thermally activatable pH-adjusting agent.
  • diazonium salts can be mentioned as representative examples of the wide variety of diazonium salts which decompose when subjected to actinic radiation and which can be used in the novel photosensitive compositions and processes of the present invention:
  • X represents an anion, such as chlorozincate (ZnCl 2 ) and borontetrafluoride (BF 4 );
  • R 1 and R 2 are the same or different and represent H, alkyl, alkoxy, alkylmercapto, aryl, aralkyl, halo, or carboxy;
  • R 3 represents aryl
  • R 4 and R 5 are the same or different and represent hydrogen, alkyl, aryl, aryloxy, hydroxyalkyl, aralkyl, alkylacyl, and aroyl groups or R 4 and R 5 together. can form a 5- or 6-membered heterocyclic group, such as morpholine, pyrrolidine, and piperidine groups; and R 6 represents alkyl, aryl, aralkyl, alkaryl.
  • a preferred group of aryldiazonium compounds includes 1-diazo-4-dimethylaminobenzene; 1-diazo-4-diethylaminobenzene; 4-diazo-N,N-diethylaminobenzene; 1-diazo-4-hydroxyethyl-N-ethylaminobenzene; 4-diazo-N-hydroxyethyl-N-ethylaminobenzene; 1-diazo-2,5-diethoxy-4-methoxybenzoylaminobenzene; 1-diazo-2, 5-diethoxy-4-phenylmorpholine; 1-diazo-2,5-dibutoxy-4-phenylmorpholine; and 4-diazo-2-methyl-N-phenylpyrrolidine; especially the ZnCl 2 and BF 4 salts thereof.
  • the light-sensitive aryldiazonium compound is present in the photosensitive layer in amounts of from about 0.02 to about 0.3 grams per square meter, preferably from about 0.1 to 0.15 g/sq.m.
  • the other essential ingredient of the photosensitive composition from which the photosensitive layer is formed is a heat-activatable pH adjusting agent. This agent functions to shift the .pH of the transferred photosensitive layer to the alkaline range simultaneously with the transfer step. Accordingly, heat transfer and development of the azo dye color reaction product by the diazo coupling reaction occur at the same time.
  • the pH adjusting agent is normally weakly acidic and thus also functions as a stabilizer against premature coupling reaction.
  • Suitable temperature sensitive pH-adjusting agents which can be used in the present invention include saccharine, di ⁇ yandiamide, semicarbazone, succinhydrazide, guanidine-2-benxothiazole, semicarbazide hydrochloride, thiosemicarbazide and isopropylamine and the salts, such as the alkali metal salts of these compounds. Saccharine, especially sodium, saccharine, is particularly preferred.
  • the amount of the pH-adjusting agent is therefore selected to be within the range which will give an alkaline environment during heat transfer.
  • amounts in the range of from about 0.02 to 0.3 g/sq.m., preferably from about 0.1 to about 0.2 g/sq.m. can be used.
  • acidic stabilizers examples include such organic acids as citric acid, salicylic acid, sulfosalicylic acid, benzoic acid, benzene sulfonic acid, ascorbic acid, oxalic acid, succinic acid, tartaric acid, and acetic acid, and weak. inorganic acid, such as boric acid and phosphoric acid.
  • antioxidants mention can be made of, for instance, thiourea, ethylurea, bisphenol A, N-hydroxyethyl-N-alkylthiourea, and the like.
  • suitable metal salts and complexing agents include zinc chloride, stannic and stannous chloride, sodium cobalt nitride, ammonium, thiosulfate and hexamethylenetetraamine.
  • Suitable surfactants and wetting agents can be selected generally from among the several classes of nonionic and anionic surface active agents well known in the art, for example, Saponin, Tergitals (Union Carbide), Armacs (Armour & Co.), Igepals (American Cyanamide), Lissapols (ICI), Pluronics (Wyandotte), and the like.
  • a typical and preferred photosensitive composition will contain. a mixture of the following reactants and adjuvants in the following amounts:
  • metal salt/complexing agent 0.01 - 0.15 g/sq.m., preferably 0.1 g/sq.m.
  • acidic stabilizer 0.02 - 0.3 g/sq.m., preferably 0.2 g/sq.m.
  • antioxidant 0.02 - 0.3 g/sq.m., preferably 0.1 g/sq.m.
  • the photosensitive composition is dispersed in a state of fine dispersion, preferably, in a state of a solid emulsion, or more preferably, a solid solution in an organic binder.
  • the selection of the organic binder is an important feature of the present invention.
  • the organic binder should be moderately hydrophilic, but not hydroscopic such as, for example, as is the case in polyvinyl alcohol or other binders which absorb humidity; it must have a softening point within the temperature range of the heat transfer step; it must be of a nature to allow the ionic diffusion mechanism and the diazo coupling reaction to proceed sufficiently rapidly, and it should adhere to the textile material, ideally, by ionic bonding.
  • ethyl cellulose satisfies all of these requirements and is the preferred organic binder.
  • Methyl cellulose, carboxymethylcellulose, and hydroxyethylcellulose can also be used but are generally too hydrophilic or have too high an hydroxyl group content and are less preferred.
  • Synthetic resin binders and natural binders such as polyvinyl acetate, polyvinylpyrrolidone, and gelatine, can also be used.
  • Mixtures of organic binders are also within the scope of the invention and, for example, up to about 20%, preferably up to about 10% of ethylcellulose can be replaced by another binder compatible therewith.
  • the organic binder and the other ingredients of the photosensitive composition are coated on the release coating layer of the paper film substrate from a solvent solution, in the dark or in a yellow light, using conventional methods, such as Meyer rod or reverse roll.
  • Solvents such as aliphatic alcohols, e g., methanol, ethanol, etc., and ketones, e.g., acetone, methylethyl ketone, etc., can be used. Mixtures of ethanol and acetone at weight ratios of from about 1:4 to about 4:1, preferably, 1:2 to 3:1, are especially preferred.
  • the amounts of the aryldiazonium compound, pH shifting compound, acidic stabilizer and antioxidant in the coating solution will each range from about 20 to 100 g, preferably from about 50 to 80 g/liter, these amounts providing the concentrations in the dry photosensitive layer described above.
  • the amount of the organic binder will be selected to provide a thickness of the photosensitive layer on the order of from about 5 up to about 10 microns.
  • the textile material on which the color image is to be printed is initially activated by a diazonium coupler compound or by a mixture of diazonium coupler compounds. The selection of the coupler compound or mixture of coupler compounds determines the color of the printed image.
  • couplers such as, for example, ph
  • a preferred group of coupler compounds includes, 2,3-dihydroxynaphthalene; ⁇ -resorcylic acid monoethanolamide; ⁇ -oxynaphthoic acid monoethanolamide; 2-hydroxy-3-naphthoic acid diethanolamide; 3-resorcylic acid ethanolamide; sodium-1-hydroxynaphthalene-4-sulfonate; 2-hydroxy-3-naphthoic acid of 2'hydroxy N-ethyl amide; 2-hydroxy napthoic acid 3-morpholino propylamide; 3-hydroxy naphthalene 2-carboxylic acid morpholine propylamide; 2,4,2',4' tetrahydroxy diphenylsulfide.
  • the presensitizing coating layer will most preferably be applied to the textile from a presensitizing film transfer paper.
  • This transfer paper can be formed from the same type of film substrate with release layer as described above for the photosensitive film transfer paper.
  • a bleached Kraft paper with a polyethylene, silicone resin, or metal soap release layer can be used as the film substrate.
  • a presensitizing layer including one or more diazonium coupler compounds uniformly dispersed in an organic binder is deposited on the release layer to form the presensitizing film transfer paper.
  • the coupler or coupler mixture is present in the presensitizing coating layer in a state of fine dispersion, most preferably as a solid emulsion or solid solution with the organic binder.
  • the preferred organic binder is ethylcellulose as the sole organic binder or with up to about 20% by weight, preferably up to about 10% by weight, of another organic binder.
  • the amount of the coupler of mixture of couplers in the presensitizing coating layer should be sufficient to provide from about 0.03 to about 0.4 g/sq.m. of the transfer film surface, preferably from about 0.5 to about 0.8 g/sq.m.
  • the amount of the organic binder should be sufficient to provide a thickness of the presensitizing coating layer in the range of from about 3. up to about 10 microns.
  • the diazo coupler compound or mixture thereof and organic binder are coated on the release layer of the paper substrate by any conventional means, such as, Meyer rod or reverse rolls from a solvent solution.
  • Any conventional means such as, Meyer rod or reverse rolls from a solvent solution.
  • the same solvents described above for the photosensitive coating can be used for this purpose.
  • the amount of the coupler should be from about 30 to about 150 grams, preferably from about 80 to about 120 grams of coupler per liter of solvent.
  • the presensitizing film transfer paper can also be used for a continuous process of printing color images on a continuous web of textile material.
  • One suitable arrangement of a continuous process is illustrated in figure 4.
  • the presensitizing film transfer paper, as well as the photosensitive film transfer paper are formed as continuous wound paper rolls by conventional paper coating techniques.
  • the textile material is presensitized by placing the presensitizing film, presensitizing layer face down, on the textile material, and placing the assembly in a heat transfer press, which is put in the operative position with the temperature adjusted to exceed the softening point of the organic binder, for a time sufficient to transfer the presensitizing layer to the textile. After transfer is completed, the press is opened and the paper is removed from the textile, and will be replaced by the exposed photosensitive film.
  • Heat transfer presses are commercially available and generally operate at a fixed temperature of about 350°F. At this temperature, transfer of the presensitizing layer is completed in about 30 seconds when ethyl cellulose is used as the organic binder. For other binders and for other operating temperatures, the heat transfer time can be easily determined by routine experimentation.
  • the photosensitive layer of the photosensitive film is exposed to actinic radiation, usually light in the ultraviolet wave length range, through a positive transparency of the photograph to be reproduced. Generally, exposure times from about 20 to about 50 seconds are sufficient to decompose the light sensitive aryldiazonium compound. Exposure equipment for this purpose is readily commercially available. Of course the order of steps 1 and 2 can be reversed or these steps can be carried out at the same time.
  • the exposed photosensitive film replaces the removed presensitizing film transfer paper in contact with the presensitized textile material (the exposed photosensitive layer will be facing and in intimate contact with the presensitizing coating transferred to the textile material) and the heat transfer press is again put in the operative position, at the same temperature for a period of time which is sufficient to complete the heat transfer of the photosensitive layer and development of the color image formed by the diazo coupling reaction between the diazonium coupler compound or compounds and the light-sensitive aryl diazonium compound. For most of the aryldiazonium compounds, transfer and development is completed in about 50 to 55 seconds at a temperature of 350oF.
  • the press is opened and the photosensitive film is peeled from the textile material.
  • This process provides a high quality print on substantially any textile fabric.
  • the contrast of the print, its definition and intensity, as well as the washability of the fabric without altering or degrading the print, are highly satisfactory, and substantially better than that obtainable by the sublistatic process.
  • the process of the invention has the further advantage of allowing the reproduction of any photographic subject from a positive transparency.
  • the manual process, according to the invention is particularly adaptable to garment printing with a garment heat transfer press. Such presses are produced by various manufacturers, such as Lawson Co., St. Louis, Missouri, for use in the sublistatic process.
  • the process of the present invention is also adaptable for continuous and automatic operation for printing on continuous running lengths of textile material, including by way of example only, woven, non-woven, and knitted fabrics made from any type of natural or synthetic fibers, such as cotton, polyester, cellulose acetate, nylon, rayon, etc. Naturally, a loosely woven or knitted fabric having a high percentage of open spaces would not be expected to provide a complete reproduction of the original image in view of the many areas not available for printing.
  • the embodiment of the invention process using a manual heating press is schematically shown in figures 1-3. In figure 1(a), the textile material 15 to be printed is placed upon the lower heating element 14 of the heating press 10.
  • the presensitizing film transfer paper 16 including the paper base 161 and presensitizing coating layer 162, is placed on top of the textile 15 such that the textile and presensitizing coating layer are in contact with each other.
  • the heating press is placed in the operative position by closing the upper arm 11 which articulates on a pivot 12 such that the upper heating element 13 presses upon the assembly of the textile material and presensitizing film transfer paper.
  • the heating elements 13 and 14 are activated to a temperature of about 350oF for about 30 seconds or such other time as determined to be necessary to effect complete transfer.
  • the press is opened and the paper 16 is peeled from the textile fabric leaving behind a presensitized coating which contains the diazonium coupler compound or compounds.
  • FIG. 2 shows the exposure of the photosensitive film transfer paper 17 in the exposure box 18.
  • the exposure box includes an ultraviolet light source 19 in housing 22, exposure timer 21, diffusing glass 23, pressure plate 24, and base 25.
  • the photosensitive film transfer paper 17 is placed in the exposure box with the paper base side 171 in contact with the pressure plate and. the photographic positive transparency 26 is placed on top of the photosensitive layer 172 of the photosensitive film transfer paper.
  • the exposed photosensitive film transfer paper is placed on top of the presensitizing coating layer transferred onto textile fabric 15 in the heating press with the photosensitive layer in contact with the transferred presensitizing coating layer [see Fig. 1(a)].
  • the press is again closed into the operative position and maintained for a sufficient period of time to soften the release layer of the paper base and allow the heat transfer of the photosensitive film and development of the color image.
  • the press is again opened and the photosensitive film transfer paper is peeled from the textile to expose the printed color image.
  • Figure 4 illustrates an embodiment of a continuous process for printing images from photographs on textile webs.
  • a textile web 30 is unwound from roll 31 and moving in the direction of the arrows, passes through a presensitizing zone A, and a development zone B, and the printed textile is wound on roll 32.
  • a first set of transfer heating rollers 34 and 35 are located respectively above and below the textile 30.
  • a continuous web of presensitizing film transfer paper 36 is stored on roll 37 and is wound up on roll 38.
  • a second set of transfer heating rollers 39 and 40 are located respectively above and below the textile web 30.
  • the photosensitive film transfer paper 41 is stored on winding roll 42 and rewound on roll 43.
  • the exposure of the photosensitive layer is accomplished with an exposure device which includes an ultraviolet tube 44 centered in a mask 48 located within quartz glass tube or cylinder 45.
  • a positive transparency 46 of the pattern to be printed on the textile web is secured on the glass cylinder 45.
  • Counter roller 47 presses the photosensitive layer of the photosensitive film transfer paper against the positive transparency 46 to insure good optical reproduction when both are rotated by the advance of the transfer paper 41.
  • the continuous printing process using the apparatus illustrated in figure 4 operates as follows: Textile web 30 unrolls from storage roller 31 by the positive drive of wind-up roller 32, and passes between the first set of transfer rollers 34 and 35 in the presensitizing zone A.
  • the presensitizing film transfer paper also passes between roller 34 and 35 and transfers the diazo coupling compound onto the textile web.
  • the photosensitive layer of the photosensitive film transfer paper 41 is photographically exposed through the positive transparency as the photosensitive film transfer paper moves in the direction shown by the arrows passed opening 49 in mask 48.
  • the exposed photosensitive layer passes between heating rollers 39 and 40, the photosensitive layer is transferred onto the presensitized textile web, whereby the final image is formed on the textile web by the diazo coupling reaction.
  • the textile web, having printed thereon the color image corresponding to the positive transparency, is wound up on roll 32.
  • the composition of the presensitizing layer and, particularly, the diazonium coupling compound selected determine the color of the reproduced image whereas the positive transparency determines the pattern of the image.
  • the composition of the presensitizing layer and, particularly, the diazonium coupling compound selected determine the color of the reproduced image whereas the positive transparency determines the pattern of the image.
  • three positive transparencies are formed from the photographic image, each of which is adapted for color separation for the three primary colors, red, blue, and yellow.
  • three presensitizing zones, A', A", and A"' are provided between rolls 31 and 32.
  • the presensitizing layer will include a coupler compound for producing one of the three primary colors, for example, red, and the positive transparency in zone B' will be correspondingly selected to reproduce the red image on the photosensitive layer of the photosensitive film transfer paper.
  • the presensitizing layer will include a diazo coupler compound for the remaining two primary colors, for example, blue and yellow, respectively.
  • the positive transparency will be adapted for color separation of blue and yellow.
  • PAPER A Presensitizing Film Transfer Paper
  • PAPER B Photosensitive Film Transfer Paper
  • a blue image is printed on cotton fabric through the following steps: a) Expose paper B to an ultraviolet light (Philips TKD type 2 fluorescent tube) through a positive transparency for 50 seconds. b) Place paper A face down on the area to be printed on the fabric, and heat both at 320°F for 30 seconds in a heat transfer press. c) Open the press, peel off paper A from the fabric and replace it by the exposed paper B in the exact same position as paper A. d) Close the press again and heat at 320oF for 60 seconds. e) Open the press, peel off paper B and remove the printed cotton textile fabric.
  • PAPER A Presensitizing Film Transfer Paper
  • PAPER B Photosensitive Film Transfer Paper
  • FILM SUBSTRATE On a glazed, bleached Kraft paper 100 g/m 2 , a 20% dispersion of SILASTIC S-2288 (Silicone resin-Dow Corning) in xylene is coated, and subsequently dried to form a film substrate for the presensitizing film and photosensitive film transfer sheets.
  • SILASTIC S-2288 Silicone resin-Dow Corning
  • PAPER A Presensitizing Film Transfer Paper
  • PAPER B Photosensitive Film Transfer Paper
  • FILM SUBSTRATE On a clay coated paper 100 g/m , a 30% solution of Silcolease 425. (Silicone resin-Imperial Chemical Industries) in toluene in which 4% of catalyst 59A (ICI) has been added, is coated and dried to form a film substrate for presensitizing film and photosensitive film transfer papers:
  • PAPER A Presensitizing Film Transfer Paper
  • PAPER B Photosensitive Film Transfer Paper

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)

Abstract

Des images photographiques en couleurs monochromatiques ou polychromatiques sont developpees directement sur des materiaux textiles tels que des chemises ou des bandes textiles continues par un procede de transfert thermique. Le materiau textile (15) est d'abord presensibilise par application sur celui-ci d'un revetement d'un compose d'accouplement au diazonium, de preference par transfert thermique du compose d'accouplement au diazonium depuis une premiere feuille de papier (16). Un film photosensible contenant une couche photosensible (162) comprenant un compose d'aryldiazonium sensible a la lumiere est expose a un film transparent positif puis est amene au contact du materiau textile presensibilise. L'ensemble est chauffe pour provoquer le transfert du compose d'aryldiazonium sensible a la lumiere sur le materiau textile presensibilise dans des conditions qui permettent a la reaction d'accouplement du diazo d'avoir lieu. Des images multicolores sont formees en appliquant trois couches de presensibilisation pour chacune des trois couleurs de base, le rouge, le bleu, et le jaune et en exposant de maniere correspondante le film photosensible au travers des films transparents positifs pouvant effectuer la separation des couleurs. La couche photosensible (162) du film photosensible comprend, en plus du compose d'aryldiazonium sensible a la lumiere, un agent d'ajustement du pH pouvant etre active a la chaleur, et un liant organique. Le procede peut s'effectuer en utilisant un materiel photographique courant et permet d'obtenir des epreuves d'images de qualite superieure a celles obtenues avec le procede de transfert conventionnel.
PCT/US1982/000176 1981-02-13 1982-02-12 Procede de formation d'images en couleurs sur des materiaux textiles et films photosensibles utilises dans ce procede WO1982002689A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU82719/82A AU8271982A (en) 1981-02-13 1982-02-12 Process for forming colored images on textile materials and photosensitive film for use in said process

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US23420781A 1981-02-13 1981-02-13
US234207810213 1981-02-13

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WO1982002689A1 true WO1982002689A1 (fr) 1982-08-19

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2575418A1 (fr) * 1984-12-31 1986-07-04 Sofec Imprimantes iteratives a changement rapide de programme
US10051905B2 (en) 2016-08-19 2018-08-21 Levi Strauss & Co. Laser finishing of apparel
US10712922B2 (en) 2017-10-31 2020-07-14 Levi Strauss & Co. Laser finishing design tool with damage assets
US11000086B2 (en) 2018-02-27 2021-05-11 Levi Strauss & Co. Apparel design system with collection management
US11250312B2 (en) 2017-10-31 2022-02-15 Levi Strauss & Co. Garments with finishing patterns created by laser and neural network
US11313072B2 (en) 2018-02-27 2022-04-26 Levi Strauss & Co. On-demand manufacturing of laser-finished apparel
US11484080B2 (en) 2018-11-30 2022-11-01 Levi Strauss & Co. Shadow neutral 3-D garment rendering
US11530503B2 (en) 2019-07-23 2022-12-20 Levi Strauss & Co. Three-dimensional rendering preview in web-based tool for design of laser-finished garments
US11680366B2 (en) 2018-08-07 2023-06-20 Levi Strauss & Co. Laser finishing design tool

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2409564A (en) * 1941-05-28 1946-10-15 Noc Mfg Company Di Transfer material
US2528395A (en) * 1946-12-31 1950-10-31 Gen Aniline & Film Corp Diazotype dry strip film
US2743191A (en) * 1952-05-13 1956-04-24 Dick Co Ab Method for manufacturing transfer sheets for spirit duplication
US2747999A (en) * 1953-03-16 1956-05-29 Eastman Kodak Co Photographic reproduction process
US2882151A (en) * 1955-10-31 1959-04-14 Eastman Kodak Co Photographic roll film transfer process
US3013917A (en) * 1960-06-09 1961-12-19 Karlan Mac Dry transfer sheet and method
BE645320A (fr) * 1963-03-19 1964-09-17
US3536490A (en) * 1964-04-28 1970-10-27 Pitney Bowes Inc Novel diazotype copying process
US3660581A (en) * 1969-04-23 1972-05-02 Allied Paper Inc Thermally developable diazotype printing paper and composition therefor
US3909328A (en) * 1973-04-10 1975-09-30 Du Pont Decoration of substrates by thermal transfer of photosensitive, thermoplastic, dye-imaged film
US3996056A (en) * 1973-04-10 1976-12-07 Andrews Paper & Chemical Co. Diazotype reproduction layer formed from matrix of spheric particle polystyrene pigment and diazotype components
US4066802A (en) * 1975-12-22 1978-01-03 Xerox Corporation Colored xerographic image transfer process

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2409564A (en) * 1941-05-28 1946-10-15 Noc Mfg Company Di Transfer material
US2528395A (en) * 1946-12-31 1950-10-31 Gen Aniline & Film Corp Diazotype dry strip film
US2743191A (en) * 1952-05-13 1956-04-24 Dick Co Ab Method for manufacturing transfer sheets for spirit duplication
US2747999A (en) * 1953-03-16 1956-05-29 Eastman Kodak Co Photographic reproduction process
US2882151A (en) * 1955-10-31 1959-04-14 Eastman Kodak Co Photographic roll film transfer process
US3013917A (en) * 1960-06-09 1961-12-19 Karlan Mac Dry transfer sheet and method
BE645320A (fr) * 1963-03-19 1964-09-17
US3157503A (en) * 1963-03-19 1964-11-17 Keuffel & Esser Co Diazotype reproduction materials
US3536490A (en) * 1964-04-28 1970-10-27 Pitney Bowes Inc Novel diazotype copying process
US3660581A (en) * 1969-04-23 1972-05-02 Allied Paper Inc Thermally developable diazotype printing paper and composition therefor
US3909328A (en) * 1973-04-10 1975-09-30 Du Pont Decoration of substrates by thermal transfer of photosensitive, thermoplastic, dye-imaged film
US3996056A (en) * 1973-04-10 1976-12-07 Andrews Paper & Chemical Co. Diazotype reproduction layer formed from matrix of spheric particle polystyrene pigment and diazotype components
US4066802A (en) * 1975-12-22 1978-01-03 Xerox Corporation Colored xerographic image transfer process

Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2575418A1 (fr) * 1984-12-31 1986-07-04 Sofec Imprimantes iteratives a changement rapide de programme
US11384463B2 (en) 2016-08-19 2022-07-12 Levi Strauss & Co. Using laser to create finishing pattern on apparel
US10051905B2 (en) 2016-08-19 2018-08-21 Levi Strauss & Co. Laser finishing of apparel
US10327494B2 (en) 2016-08-19 2019-06-25 Levi Strauss & Co. Laser finishing of apparel
US10470511B2 (en) 2016-08-19 2019-11-12 Levi Strauss & Co. Using laser to create finishing pattern on apparel
US11673419B2 (en) 2016-08-19 2023-06-13 Levi Strauss & Co. Creating a finishing pattern on a garment by laser
US11629443B2 (en) 2016-08-19 2023-04-18 Levi Strauss & Co. Using fabric response characteristic function to create laser finishing patterns on apparel
US11479892B2 (en) 2016-08-19 2022-10-25 Levi Strauss & Co. Laser finishing system for apparel
US10980302B2 (en) 2016-08-19 2021-04-20 Levi Strauss & Co. Laser finishing of apparel
US10956010B2 (en) 2017-10-31 2021-03-23 Levi Strauss & Co. Laser finishing design tool with photorealistic preview of damage assets
US10891035B2 (en) 2017-10-31 2021-01-12 Levi Strauss & Co. Laser finishing design tool
US10712922B2 (en) 2017-10-31 2020-07-14 Levi Strauss & Co. Laser finishing design tool with damage assets
US11250312B2 (en) 2017-10-31 2022-02-15 Levi Strauss & Co. Garments with finishing patterns created by laser and neural network
US11681421B2 (en) 2017-10-31 2023-06-20 Levi Strauss & Co. Laser finishing design and preview tool
US10921968B2 (en) 2017-10-31 2021-02-16 Levi Strauss & Co. Laser finishing design tool with image preview
US11952693B2 (en) 2017-10-31 2024-04-09 Levi Strauss & Co. Using neural networks in laser finishing of apparel
US11941236B2 (en) 2017-10-31 2024-03-26 Levi Strauss & Co. Tool with damage assets for laser
US11592974B2 (en) 2017-10-31 2023-02-28 Levi Strauss & Co. Laser finishing design tool with image preview
US11000086B2 (en) 2018-02-27 2021-05-11 Levi Strauss & Co. Apparel design system with collection management
US11618995B2 (en) 2018-02-27 2023-04-04 Levi Strauss & Co. Apparel collection management with image preview
US11702793B2 (en) 2018-02-27 2023-07-18 Levi Strauss & Co. Online ordering and manufacturing of apparel using laser-finished fabric rolls
US11697903B2 (en) 2018-02-27 2023-07-11 Levi Strauss & Co. Online ordering and just-in-time manufacturing of laser-finished garments
US11352738B2 (en) 2018-02-27 2022-06-07 Levi Strauss & Co. On-demand manufacturing of apparel by laser finishing fabric rolls
US11313072B2 (en) 2018-02-27 2022-04-26 Levi Strauss & Co. On-demand manufacturing of laser-finished apparel
US11680366B2 (en) 2018-08-07 2023-06-20 Levi Strauss & Co. Laser finishing design tool
US11632994B2 (en) 2018-11-30 2023-04-25 Levi Strauss & Co. Laser finishing design tool with 3-D garment preview
US11612203B2 (en) 2018-11-30 2023-03-28 Levi Strauss & Co. Laser finishing design tool with shadow neutral 3-D garment rendering
US11925227B2 (en) 2018-11-30 2024-03-12 Levi Strauss & Co. Shadow neutral 3-D visualization of garment
US11484080B2 (en) 2018-11-30 2022-11-01 Levi Strauss & Co. Shadow neutral 3-D garment rendering
US11668036B2 (en) 2019-07-23 2023-06-06 Levi Strauss & Co. Three-dimensional rendering preview of laser-finished garments
US11530503B2 (en) 2019-07-23 2022-12-20 Levi Strauss & Co. Three-dimensional rendering preview in web-based tool for design of laser-finished garments

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