US2657140A - Developer for diazotype materials - Google Patents
Developer for diazotype materials Download PDFInfo
- Publication number
- US2657140A US2657140A US290563A US29056352A US2657140A US 2657140 A US2657140 A US 2657140A US 290563 A US290563 A US 290563A US 29056352 A US29056352 A US 29056352A US 2657140 A US2657140 A US 2657140A
- Authority
- US
- United States
- Prior art keywords
- diazotype
- developer
- acid
- copy
- optical bleaching
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- 239000000463 material Substances 0.000 title claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 10
- 230000008878 coupling Effects 0.000 claims description 9
- 238000010168 coupling process Methods 0.000 claims description 9
- 238000005859 coupling reaction Methods 0.000 claims description 9
- -1 AMINO GROUPS Chemical group 0.000 claims description 7
- 239000000975 dye Substances 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical group C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 description 16
- 238000009994 optical bleaching Methods 0.000 description 16
- 239000007844 bleaching agent Substances 0.000 description 15
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 150000008049 diazo compounds Chemical class 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 230000001808 coupling effect Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 2
- 229960001553 phloroglucinol Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- FZQSLXQPHPOTHG-UHFFFAOYSA-N [K+].[K+].O1B([O-])OB2OB([O-])OB1O2 Chemical compound [K+].[K+].O1B([O-])OB2OB([O-])OB1O2 FZQSLXQPHPOTHG-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 235000011126 aluminium potassium sulphate Nutrition 0.000 description 1
- VBIXEXWLHSRNKB-UHFFFAOYSA-N ammonium oxalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C([O-])=O VBIXEXWLHSRNKB-UHFFFAOYSA-N 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 235000010338 boric acid Nutrition 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 239000000337 buffer salt Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- VDUIPQNXOQMTBF-UHFFFAOYSA-N n-ethylhydroxylamine Chemical compound CCNO VDUIPQNXOQMTBF-UHFFFAOYSA-N 0.000 description 1
- ZPBSAMLXSQCSOX-UHFFFAOYSA-N naphthalene-1,3,6-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 ZPBSAMLXSQCSOX-UHFFFAOYSA-N 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- DGSDBJMBHCQYGN-UHFFFAOYSA-M sodium;2-ethylhexyl sulfate Chemical compound [Na+].CCCCC(CC)COS([O-])(=O)=O DGSDBJMBHCQYGN-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
- G03C5/29—Development processes or agents therefor
- G03C5/305—Additives other than developers
-
- 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
- Y10S430/134—Brightener containing
Definitions
- the invention relates to a developer for diazotype printing materials referred to hereinafter as a "diazotype developer.
- a diazotype developer a mixture (either a dry mixture to be dissolved, or a solution) containing as essential constituents one or more azo dyestuff coupling components and one or more potassium and/ or sodium salts of weak acids, such as carbonic acid, boric acid, formic acid, acetic acid, benzoic acid, tartaric acid and citric acid.
- Azo dyestuii components of good coupling activity are used and the alkali salts are so chosen that, in the slight excess used, they ensure sufficient azo dyestuff coupling between the azo dyestufi coupling components and the diazo compound used in the diazotype image the unexposed areas of which containa para-amino-diazo-benzene compound, with the usual quantities of acid con stituents.
- Azo dyestuff components of good coupling activity are, for example S-naphthol, the [i hydroxy-ethyl amide of Z-hydroxy-B-naphthoic acid, phloroglucinol, and resorcinol; an azo dyestuff component of insufficient coupling activity In the Netherlands June 16,
- Diazotype developers are applied practically exclusively in such a manner that their aqueous solution is applied on the diazotype copy in-a layer of, for example, 8 to 12 g./so metre.
- diaaotype develop ers generally also contain substances such as thiourea, alkali thiosulphate, wetting agents, aliphatic polyhydroxy compounds and the like.
- Diazotype developers with borates are to be preferred to those withcarbonates.
- Diazotype developers that have to serve for the development of diazotype copies in which the diazo compound is a para-alkylamino-diazobenzene usually have a pH above .7; those used for diazotype copies containing para-acylamino-diazo-benzene compounds may have a pH alittle below 7,.while their concentration of buffer salts, such as formates, benzoates, and the'like is generally higher.
- diazotype' developers contain optical bleaching agents known per se (of. for example Netherlandspatent specification No. 55,370).
- the diazotype developers according to the in vention contain as optical bleaching agent a blue-fluorescent salt of a p.p-diaminostilbeneo.o-disulphonic acid with one or more 1.3.5- triazine rings attached to the amino groups.
- This type of optical bleaching agent'with at least one triazine ring was found to be more suitable for the above-mentioned application in diazotype developers and to have a greater or more lasting effect than optical bleaching agents without a triazine ring derived from p.p-diaminostilbene-o.o'-disulphonic acid (of. for example French patent specification No. 878,155).
- optical bleaching agents used according to the invention are:
- R1, R2, R3 and R4 stand for amino or aliphatically or aromatically substituted amino groups. Particularly good results are obtained with compounds in which the substituents R1, R2, R3 and R4 are amino groups at least one of which is aromatically substituted, and even better results when one or more of these aromatical ly substituted amino groups have a sulphonic acid or a carboxyl group attached to the arc matic radicle. Many of these can be dissolved in aqueous diazotype developers without any previous treatment. Less soluble optical bleaching agents of the type preferred for the invention may be finely distributed or emulsified in the aqueous developer.
- diazotype copies such as the azo. component B-hydroxy-ethyl amide of 2-hydroxy-naphthalene3-carboxylic acid, the photochemical decomposition product of a diam-compound, a stabiliser such as, for example, naphthalene-1.3.6-trisulphonic acid, and also when the diazotype copies begin to show the familiar discolouration uponageingi It has .3 also bee'n'found thattheeopticalbleaching agents, appliedto the diazotype copy via the diazotype developer, reduce the discolouration of the copy in daylight, a result which is particularly valu+ able when the diazotype copy-ie-ex-posedto light that is relatively rich in rays of short" wave lengths.
- a developer suitable for the development of diazotype paper B is composed as follows:
- Diazotypei paper 8 Base papie'r of"80 gi/s'q metre-' is coated with about 12 g./sq. metre of the following solution Acopy on the diazotype materiaLBisdeveloped by the applicationof. aboutlOg/sq. metre. of the above developer. Adark brownicopy-is'obta-ined in which. the darlebrown-z dyestuff. is in J high con! trastwith the. clear white. ground. If the optical bleaching agent had been omitted iromlthe: composition of the developer, a copy would haveibeen obtained with: a somewhat dingy: background, with whichthe imageiwould contrast considerably 7 less.
- A- copy on diazoty-pe material A. is developed by the application of. about? 1-01" g./'sq. metre of the above developer.
- a developer suitable for the development of diazotype paper A is composed as follows:
- a developer suitable for the development 01 diazotype paper C is composed as follows:
- a brownish-black copy is oh- I l 5o tained in which the brownish-black dyestufi is in g of lsopropyl naphthalene Sm 3 strong contrast with the clearwhite ground. If 2 ac "i "f" the optical bleaching agent had been omitted Tr mm D 05p a e from the composition of the developer copy sodaFsh anhydrous 20 would have been obtained with a somewhat dingy Caffeme 5; ground, with which the image would contr considerably less.
- H0 C H4NH-G I N ⁇ O/ OgNa dome NH NH SOIH 0311 Water g- 1000' What I claim is:
- a copy on diazotype material A is developed by the application of about 10 g./sq. metre of the above developer. A brown copy is obtained, in
- a developer for diazotype printing materials comprising at least one azo dyestuffco'upling component, at least one alkaline metal salt 'of a weak acid and a small amount of a salt of a blueenemas) :sulphonic acid compound containing one 1:315- triazine ring attached to each amino group and having the formula l N.
- R1, R2, R3 and R4 is an aromatically substituted amino group, at least one member of R1, R2 R3 and is analiphat;
- V oaNa AOiNa fin which R1, R2, R3 and R4 are amino groups 3.
- a developer for diazotype printingmaterials ⁇ comprising at least one azo dyestufii coupling cpmponent, at least one alkaline metal salt or" a weak acid and a pp-diaminostilbene-o.o'-disulphonic. acid compound containing one 1 :3 5- t'riazine ring attached to each amino group and having the formula:
- a developer for diazotype printing materials comprising at least one azo dyestufi coupling 30 component, at least one alkaline metal salt of a weak acidand a p.pediaminostilbene-omedisulphonic acid compoundcontaining one 1:-3:5'-tri- C l R:
- v 4 a 4..- A developer f or diazot-ype printing materials comprising at least: one azo dyestu-ff coupling component, at: least one alkalinemetal salt of a weak acid: and a pipadiaminostilbeneaoo ditriazine ring attached to each amino-4 group. and having the formula:
- R1, R2, and R4 is an aromatically substituted amino group and any em inine m m sof R1, Rafts and 34am ,5 Qg oun a A d vel per for diazo ype-pr ingma er al sulphonic acid compound containing one 123:5
- a developer for diazotype printing mate fals comprising at least one azo dyestufi coupling component, at least one alkaline metal salt of a Weak acidand a p;p-diaminostilbene-o.o" cli sulphonic acid compound containing one 123:5-
- R1 and R3 arephenylamino groups and R2 and R4 are phenylamino groups. which are substituted by a sulphoni a d rou icallysulostituted amino group and any remaining 7 in which R1, R2, R3 and R4 are di(hydroxyethyl) amino groups.
- a developer as claimed in claim 4 in which at least one of the aromatic substitutents carries a sulphonic acid group as a substituent.
- a developer as claimed in claim 4 in which at least one of the aromatic substituents carries a oarboxylic acid group as a substituent.
- a process for developing light sensitive sheet material which, at least in the unexposed condition, contains a diazo compound as the light sensitive material comprising applying to the said 110 sheet material a thin film layer of a developer as claimed in claim 1.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Luminescent Compositions (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL162031 | 1951-06-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
US2657140A true US2657140A (en) | 1953-10-27 |
Family
ID=19750527
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US290563A Expired - Lifetime US2657140A (en) | 1951-06-16 | 1952-05-28 | Developer for diazotype materials |
Country Status (6)
Country | Link |
---|---|
US (1) | US2657140A (en, 2012) |
BE (1) | BE511670A (en, 2012) |
CH (1) | CH308288A (en, 2012) |
ES (1) | ES204018A1 (en, 2012) |
FR (1) | FR1058321A (en, 2012) |
NL (2) | NL74109C (en, 2012) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3078162A (en) * | 1960-08-12 | 1963-02-19 | Gen Aniline & Film Corp | Dye brightening agent in diazotype process |
US3110596A (en) * | 1958-08-08 | 1963-11-12 | Azoplate Corp | Process for simultaneously developing and fixing printing plates |
US3493374A (en) * | 1965-07-01 | 1970-02-03 | Grinten Chem L V D | Heat-developable diazotype material |
US3628954A (en) * | 1970-03-24 | 1971-12-21 | Keuffel And Esser Co | Diazo material and visible light development process therefore |
US4147545A (en) * | 1972-11-02 | 1979-04-03 | Polychrome Corporation | Photolithographic developing composition with organic lithium compound |
US4297428A (en) * | 1979-11-05 | 1981-10-27 | Kaneo Yamamoto | Process for making diazo photosensitive paper |
US4410386A (en) * | 1981-04-30 | 1983-10-18 | Free David F | Photographic mounting process and composition |
US4528233A (en) * | 1981-07-27 | 1985-07-09 | Free David F | Photographic mounting process and composition |
US5043253A (en) * | 1987-12-11 | 1991-08-27 | Fuji Photo Film Co., Ltd. | Method for commonly processing two different silver halide color photographic light-sensitive materials |
US5238793A (en) * | 1988-06-06 | 1993-08-24 | Eastman Kodak Company | Photographic process |
US5380626A (en) * | 1992-04-06 | 1995-01-10 | Fuji Photo Film Co., Ltd. | Method for processing a silver halide photographic material using a processing solution having a bleaching ability containing one of an amidine or a bisguanidine compound |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR878823A (fr) * | 1941-02-18 | 1943-02-04 | Ig Farbenindustrie Ag | Procédé permettant d'accentuer les blancs et le pouvoir lumineux de la couleur de la surface des images photographiques |
GB624052A (en) * | 1947-05-19 | 1949-05-26 | Dennis Arthur William Adams | Stilbene derivatives for use in whitening textile materials |
FR993648A (fr) * | 1948-08-24 | 1951-11-05 | Gen Aniline & Film Corp | Acides bis- [2-morpholino-4-amino-1, 3, 5-triazyl-(6)-]-4, 4'-diaminostilbène sulfoniques et carboxyliques |
US2589519A (en) * | 1951-01-15 | 1952-03-18 | Gen Aniline & Film Corp | Fluorescent agents |
US2612501A (en) * | 1947-10-14 | 1952-09-30 | Ici Ltd | Triazine substances for textile treatment |
-
0
- NL NL7308848.A patent/NL162031B/xx unknown
- BE BE511670D patent/BE511670A/xx unknown
- NL NL74109D patent/NL74109C/xx active
-
1952
- 1952-05-28 US US290563A patent/US2657140A/en not_active Expired - Lifetime
- 1952-06-13 CH CH308288D patent/CH308288A/de unknown
- 1952-06-13 FR FR1058321D patent/FR1058321A/fr not_active Expired
- 1952-06-14 ES ES0204018A patent/ES204018A1/es not_active Expired
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR878823A (fr) * | 1941-02-18 | 1943-02-04 | Ig Farbenindustrie Ag | Procédé permettant d'accentuer les blancs et le pouvoir lumineux de la couleur de la surface des images photographiques |
GB624052A (en) * | 1947-05-19 | 1949-05-26 | Dennis Arthur William Adams | Stilbene derivatives for use in whitening textile materials |
US2612501A (en) * | 1947-10-14 | 1952-09-30 | Ici Ltd | Triazine substances for textile treatment |
FR993648A (fr) * | 1948-08-24 | 1951-11-05 | Gen Aniline & Film Corp | Acides bis- [2-morpholino-4-amino-1, 3, 5-triazyl-(6)-]-4, 4'-diaminostilbène sulfoniques et carboxyliques |
US2589519A (en) * | 1951-01-15 | 1952-03-18 | Gen Aniline & Film Corp | Fluorescent agents |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3110596A (en) * | 1958-08-08 | 1963-11-12 | Azoplate Corp | Process for simultaneously developing and fixing printing plates |
US3078162A (en) * | 1960-08-12 | 1963-02-19 | Gen Aniline & Film Corp | Dye brightening agent in diazotype process |
US3493374A (en) * | 1965-07-01 | 1970-02-03 | Grinten Chem L V D | Heat-developable diazotype material |
US3628954A (en) * | 1970-03-24 | 1971-12-21 | Keuffel And Esser Co | Diazo material and visible light development process therefore |
US4147545A (en) * | 1972-11-02 | 1979-04-03 | Polychrome Corporation | Photolithographic developing composition with organic lithium compound |
US4297428A (en) * | 1979-11-05 | 1981-10-27 | Kaneo Yamamoto | Process for making diazo photosensitive paper |
US4410386A (en) * | 1981-04-30 | 1983-10-18 | Free David F | Photographic mounting process and composition |
US4528233A (en) * | 1981-07-27 | 1985-07-09 | Free David F | Photographic mounting process and composition |
US5043253A (en) * | 1987-12-11 | 1991-08-27 | Fuji Photo Film Co., Ltd. | Method for commonly processing two different silver halide color photographic light-sensitive materials |
US5238793A (en) * | 1988-06-06 | 1993-08-24 | Eastman Kodak Company | Photographic process |
US5380626A (en) * | 1992-04-06 | 1995-01-10 | Fuji Photo Film Co., Ltd. | Method for processing a silver halide photographic material using a processing solution having a bleaching ability containing one of an amidine or a bisguanidine compound |
Also Published As
Publication number | Publication date |
---|---|
NL162031B (nl) | |
CH308288A (de) | 1955-07-15 |
BE511670A (en, 2012) | |
ES204018A1 (es) | 1953-01-16 |
NL74109C (en, 2012) | |
FR1058321A (fr) | 1954-03-16 |
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