US2940852A - m, m'-dioxydiphenols as coupling components in diazotype intermediates of high opacity - Google Patents
m, m'-dioxydiphenols as coupling components in diazotype intermediates of high opacity Download PDFInfo
- Publication number
- US2940852A US2940852A US641023A US64102357A US2940852A US 2940852 A US2940852 A US 2940852A US 641023 A US641023 A US 641023A US 64102357 A US64102357 A US 64102357A US 2940852 A US2940852 A US 2940852A
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- United States
- Prior art keywords
- opacity
- diazotype
- compound
- coupling components
- coupling
- 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
- 238000010168 coupling process Methods 0.000 title claims description 20
- 238000005859 coupling reaction Methods 0.000 title claims description 20
- 230000008878 coupling Effects 0.000 title claims description 19
- 239000000543 intermediate Substances 0.000 title description 16
- 239000000463 material Substances 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- 150000001989 diazonium salts Chemical class 0.000 claims description 2
- 239000000306 component Substances 0.000 description 20
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 14
- -1 dimethyl aminomethyl-2,5-xylenol Chemical compound 0.000 description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000011888 foil Substances 0.000 description 11
- 230000000007 visual effect Effects 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 239000000975 dye Substances 0.000 description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000006193 diazotization reaction Methods 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- RTZZCYNQPHTPPL-UHFFFAOYSA-N 3-nitrophenol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1 RTZZCYNQPHTPPL-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 235000005074 zinc chloride Nutrition 0.000 description 4
- 239000011592 zinc chloride Substances 0.000 description 4
- WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- YTVSBURBOWIMMD-UHFFFAOYSA-M 4-morpholin-4-ylbenzenediazonium;chloride Chemical compound [Cl-].C1=CC([N+]#N)=CC=C1N1CCOCC1 YTVSBURBOWIMMD-UHFFFAOYSA-M 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- IPRCBIWIPMJXIK-UHFFFAOYSA-N (3-hydroxyphenyl)urea Chemical compound NC(=O)NC1=CC=CC(O)=C1 IPRCBIWIPMJXIK-UHFFFAOYSA-N 0.000 description 1
- NFGXHKASABOEEW-GYMWBFJFSA-N (S)-methoprene Chemical compound COC(C)(C)CCC[C@H](C)C\C=C\C(\C)=C\C(=O)OC(C)C NFGXHKASABOEEW-GYMWBFJFSA-N 0.000 description 1
- RBZMSGOBSOCYHR-UHFFFAOYSA-N 1,4-bis(bromomethyl)benzene Chemical compound BrCC1=CC=C(CBr)C=C1 RBZMSGOBSOCYHR-UHFFFAOYSA-N 0.000 description 1
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
- VPMZFRCOUNREJJ-UHFFFAOYSA-N 4-(ethylamino)-3-methylbenzenediazonium Chemical compound CCNC1=CC=C([N+]#N)C=C1C VPMZFRCOUNREJJ-UHFFFAOYSA-N 0.000 description 1
- GDIIPKWHAQGCJF-UHFFFAOYSA-N 4-Amino-2-nitrotoluene Chemical compound CC1=CC=C(N)C=C1[N+]([O-])=O GDIIPKWHAQGCJF-UHFFFAOYSA-N 0.000 description 1
- 239000004101 4-Hexylresorcinol Substances 0.000 description 1
- WFJIVOKAWHGMBH-UHFFFAOYSA-N 4-hexylbenzene-1,3-diol Chemical compound CCCCCCC1=CC=C(O)C=C1O WFJIVOKAWHGMBH-UHFFFAOYSA-N 0.000 description 1
- 235000019360 4-hexylresorcinol Nutrition 0.000 description 1
- FHQRDEDZJIFJAL-UHFFFAOYSA-N 4-phenylmorpholine Chemical compound C1COCCN1C1=CC=CC=C1 FHQRDEDZJIFJAL-UHFFFAOYSA-N 0.000 description 1
- 239000004382 Amylase Substances 0.000 description 1
- 102000013142 Amylases Human genes 0.000 description 1
- 108010065511 Amylases Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 235000019418 amylase Nutrition 0.000 description 1
- 238000006149 azo coupling reaction Methods 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960003258 hexylresorcinol Drugs 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N para-hydroxytoluene Natural products CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- G03C1/00—Photosensitive materials
- G03C1/52—Compositions containing diazo compounds as photosensitive substances
- G03C1/58—Coupling substances therefor
Definitions
- the present invention relates to light sensitive diazo type materials containing m,m-dioxydiphenols as coupling components and, particularly to diazotype intermediates of high opacity containing such coupling components.
- a diazotype layer in order to be satisfactory as an intermediate material, a diazotype layer must meet rigid and diverse specifications.
- the intermediate foil should have the fastest possible printing speed consistent with good opacity, and form a dye having both good actinic opacity and good visual opacity, since visual examination of the, intermediate is frequently necessary.
- the layer must exhibit satisfactory stability, both in the packageand in the developed foil. Both the packaged and developed foil must show good stability against yellowing, especially yellowing which occurs on exposure of a developed foil to ultraviolet radiation since such yellowing increases the opacity of the material.
- the dye formed should be free from a tendency to migrate or to ofiset when in contact with other materials. Heretofore, it has not been possible to combine all of these properties to a satisfactory degree in any commercial product.
- resorcinol One of the most widely used azo dye coupling components in diazo intermediate products is resorcinol. When freshly coated in high concentration, resorcinol yields a dye having good actinic opacity. However, as the coated material ages, difiusion and redistribution of thecomponents takes place so that in place of the monoazo coupling originally predominant, bis-coupling becomes important. Resorcinol is thus very sensitive to the diazo/ coupler ratio. Consequently, as the material ages, the visual opacity increases as the result of bis-dye formation while a marked falling oil in actinic opacity occurs at the same time.
- coupling components which provide layers of good stability having good actinic opacity of which m-hydroxyphenylurea and dimethyl aminomethyl-2,5-xylenol are examples. These materials, however, suffer from restricted solubility, are prone to offset under certain circumstances, and yield layers which fail to develop the dye images rapidly and completely on exposure to ammonia. In addition, their visual opacity is poor.
- Light sensitive diazotype materials containing m;m'- dioxydiphenols as coupling components and, more par ticularly, those intermediate materials of high opacitycontaining such couplers constitute the purposes and objects of the present invention.
- polyfunctional resorcinol etherscontemplated herein may be depicted by the following general formula:
- V Isopropyl alcohol ........a ..mls
- A is alkylene such kylenearylenealkylene, i.e., methylenephenylenemethyl ene, ethylenephenyleneethylene and the like; isoalkylidcne such as isopropylidene and the like;
- X and Y are hydro gen, alkyl such as methyl, ethyl, butyl, amyl, hexyl and the like; sulfo, halogen such as chlorine and bromine;
- n 1 when p is 0 and p +1 when p is a whole number, i.e., 2 when p is .l. V
- m,m'-ethylenedioxydiphenol was made by'a modi as ethylene, trimethylene, tetramethylene, pentamethylene, methyltrimethylene; al-
- this composition yielded a yellow ish-brown image with good visual density, opacity to ultraviolet light, dye stability, and developability.
- this composition When coated on cellulose acetate foil base, dried, irradiated withfactinic light'under a positive; original, and exposed to ammonia vapors, this composition yielded a yellowish-brown image, with excellent stability and good visual density. The printingspeed and ultraviolet opacity of this material were outstanding.
- Example V The procedure is the same as in Example I excepting that the coupling component used is m,m-trirnethylenedioxydiphenol of the following formula:
- This compound may be prepared as follows: m-Nitrophenol was reacted with 1,4-dibromobutane to give 3,3- -dinitrotetramethylenedioxydibenzene, M. 7 -7 C., which was reduced in isopropyl alcohol over palladium on carbon to the amine, M. 128-30 C. 'Diazotization and hydrolysis with dilute sulfuric acid were completed as in Example V and the desired compound was obtained as Example,
- This compound may be prepared 'as follows: 1,5-divbromopentane and m-nitrophenol were condensed to 3,3- dinitropentamethylenedioxydibenzene, M. 94-6 C. This was reduced in ethyl alcohol over palladium on carbon to the amine, M. 1'l9-2l C. Diazotization and hydrolysis with-dilute sulfuric acid; gave-the desired compound as colorless ,needles, M.
- Example IX The procedure is the same as in Example HI excepting that the coupling component is 6,6-dimethyl-3,3- trimethylenedioxydiphenol of the formula:
- OH OH CH CHI OCHICBICHIO This compound may be prepared as follows: B-nitro- 4-methylphenol was prepared from 3-nitro-4-methylaniline by diazotization and hydrolysis (Harvey and Roberson, J. Chem. Soc. 1938, 97-401). This was reacted with trimethylene bromide and alkali to yield 4,4'-dimethyl-3,3'-dinitrotrimethylenedioxydibenzene, M. 106- 9 C. Reduction in ethanol over palladium on carbon went smoothly to give the amino derivative, M. 129-30 C. Diazotization and hydrolysis by the usual method gave the desired compound, M. 139-41 C.
- Example X The procedure is the same as in Example III excepting that the coupling component is m,rn'-(p-phenylenedimethylenedioxy) cliphenol of the formula:
- This compound may be prepared as follows: m-Nitrophenol and p-phenylenedimethylene bromide were reacted to give 3,3-dinitro-p-phenylenedimethylenedioxydibenzene, M. 193-6" C.
- the amino compound, prepared by reduction in ethanol over palladium on carbon was diazotized and hydrolyzed to the desired compound, M. 724 C.
- Example XI The procedure is the same as in Example II excepting that the coupling component is 6,6-dihexyl-3,3'-isopropylidenedioxydiphenol of the formula:
- Example XIII The procedure is the same as in Example 11 excepting that the coupling component employed is 4,4',6,6'-tetramethyl-3,3'-trimethylenedioxydiphenol of the formula:
- Light sensitive diazotype materials comprising a base sensitized with a light sensitive diazonium compound, and as the coupling component, the compound of the following formula:
- V zonium salt (amylase) comprising a translucent base sensitized with a light sensir 1 7 r 8 tive diazonitlm compound, and as the eonplingcomlight-sensitive compound'isa p-4-morpholinylbenzene diaponent, a compound of theiollowin'g formula: V zonium salt. V .1 V
- PATENTS 1 Y are selected from the class consisting of hydrogen, 6 6 7 Great fi n r f 9 alkyl, sulfo and halogen; p is selected fi'om'the class con- 7 1 I 'sisting of 0 and a' whole number; and n ris l when p is 7 OTHER 0"and p+1 when p is 'a whole number.. 1 Chem. Abstracts, 47; 4369g ,(1953).
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL97385D NL97385C (en, 2012) | 1957-02-19 | ||
| DENDAT1068556D DE1068556B (en, 2012) | 1957-02-19 | ||
| NL225064D NL225064A (en, 2012) | 1957-02-19 | ||
| BE564689D BE564689A (en, 2012) | 1957-02-19 | ||
| US641023A US2940852A (en) | 1957-02-19 | 1957-02-19 | m, m'-dioxydiphenols as coupling components in diazotype intermediates of high opacity |
| GB2993/58A GB840945A (en) | 1957-02-19 | 1958-01-29 | úÝ, úÝ-dioxydiphenols as coupling components in diazotype materials |
| CH5602558A CH375988A (de) | 1957-02-19 | 1958-02-19 | Lichtempfindliches Diazotypie-Material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US641023A US2940852A (en) | 1957-02-19 | 1957-02-19 | m, m'-dioxydiphenols as coupling components in diazotype intermediates of high opacity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2940852A true US2940852A (en) | 1960-06-14 |
Family
ID=24570626
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US641023A Expired - Lifetime US2940852A (en) | 1957-02-19 | 1957-02-19 | m, m'-dioxydiphenols as coupling components in diazotype intermediates of high opacity |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2940852A (en, 2012) |
| BE (1) | BE564689A (en, 2012) |
| CH (1) | CH375988A (en, 2012) |
| DE (1) | DE1068556B (en, 2012) |
| GB (1) | GB840945A (en, 2012) |
| NL (2) | NL225064A (en, 2012) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3086861A (en) * | 1960-07-01 | 1963-04-23 | Gen Aniline & Film Corp | Printing plates comprising ink receptive azo dye surfaces |
| US3113025A (en) * | 1960-03-02 | 1963-12-03 | Gen Aniline & Film Corp | Diazotype materials for the production of black images |
| US3149972A (en) * | 1960-08-16 | 1964-09-22 | Gen Aniline & Film Corp | Diazo and resinous coupler printing plates for photomechanical reproduction |
| US3183093A (en) * | 1959-12-09 | 1965-05-11 | Keuffel & Esser Co | Light sensitive diazotype material containing dibenzyl alkylamine coupling agents |
| US3186845A (en) * | 1961-11-11 | 1965-06-01 | Keuffel & Esser Co | Two-component diazotype material |
| US3300534A (en) * | 1961-01-04 | 1967-01-24 | Sun Oil Co | Process for preparing phenolic compounds |
| US3499763A (en) * | 1967-05-01 | 1970-03-10 | Ibm | Bis phenols as high opacity diazotype couplers |
| US3716364A (en) * | 1970-09-02 | 1973-02-13 | Addressograph Multigraph | Diazotype materials |
| US3769018A (en) * | 1970-05-13 | 1973-10-30 | Oce Van Der Grinten Nv | Diazotype materials containing resorcinol mono(aryloxy or arylthio)alkyl ethers |
| US4115590A (en) * | 1964-02-26 | 1978-09-19 | Ethyl Corporation | Binuclear phenols for reducing plasma lipid levels |
| US4220805A (en) * | 1978-09-18 | 1980-09-02 | General Electric Company | Linear dimers of bisphenols and method for making |
| US5569568A (en) * | 1994-12-16 | 1996-10-29 | Eastman Kodak Company | Method for using a laser ablative recording element with low red or green absorption as a reprographic photomask |
| US9243007B2 (en) | 2011-03-30 | 2016-01-26 | Asahi Kasei Chemicals Corporation | Organopolysiloxane, method for producing the same, and curable resin composition containing the organopolysiloxane |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61104887A (ja) * | 1984-10-27 | 1986-05-23 | Kanzaki Paper Mfg Co Ltd | 感熱記録体 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB626391A (en) * | 1946-05-08 | 1949-07-14 | Gen Aniline & Film Corp | Photographic diazotype compositions containing n-acylamino phenol couplers |
| US2536989A (en) * | 1948-01-20 | 1951-01-02 | Gen Aniline & Film Corp | Diazotype layers containing resorcinol derivatives |
| US2650925A (en) * | 1948-05-03 | 1953-09-01 | Laaketehdas Orion Oy | N, n'-piperazine dicarbamate of 2, 4-di-hydroxyphenylthiol |
-
0
- BE BE564689D patent/BE564689A/xx unknown
- DE DENDAT1068556D patent/DE1068556B/de active Pending
- NL NL97385D patent/NL97385C/xx active
- NL NL225064D patent/NL225064A/xx unknown
-
1957
- 1957-02-19 US US641023A patent/US2940852A/en not_active Expired - Lifetime
-
1958
- 1958-01-29 GB GB2993/58A patent/GB840945A/en not_active Expired
- 1958-02-19 CH CH5602558A patent/CH375988A/de unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB626391A (en) * | 1946-05-08 | 1949-07-14 | Gen Aniline & Film Corp | Photographic diazotype compositions containing n-acylamino phenol couplers |
| US2536989A (en) * | 1948-01-20 | 1951-01-02 | Gen Aniline & Film Corp | Diazotype layers containing resorcinol derivatives |
| US2650925A (en) * | 1948-05-03 | 1953-09-01 | Laaketehdas Orion Oy | N, n'-piperazine dicarbamate of 2, 4-di-hydroxyphenylthiol |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3183093A (en) * | 1959-12-09 | 1965-05-11 | Keuffel & Esser Co | Light sensitive diazotype material containing dibenzyl alkylamine coupling agents |
| US3113025A (en) * | 1960-03-02 | 1963-12-03 | Gen Aniline & Film Corp | Diazotype materials for the production of black images |
| US3086861A (en) * | 1960-07-01 | 1963-04-23 | Gen Aniline & Film Corp | Printing plates comprising ink receptive azo dye surfaces |
| US3149972A (en) * | 1960-08-16 | 1964-09-22 | Gen Aniline & Film Corp | Diazo and resinous coupler printing plates for photomechanical reproduction |
| US3300534A (en) * | 1961-01-04 | 1967-01-24 | Sun Oil Co | Process for preparing phenolic compounds |
| US3186845A (en) * | 1961-11-11 | 1965-06-01 | Keuffel & Esser Co | Two-component diazotype material |
| US4115590A (en) * | 1964-02-26 | 1978-09-19 | Ethyl Corporation | Binuclear phenols for reducing plasma lipid levels |
| US3499763A (en) * | 1967-05-01 | 1970-03-10 | Ibm | Bis phenols as high opacity diazotype couplers |
| US3769018A (en) * | 1970-05-13 | 1973-10-30 | Oce Van Der Grinten Nv | Diazotype materials containing resorcinol mono(aryloxy or arylthio)alkyl ethers |
| US3716364A (en) * | 1970-09-02 | 1973-02-13 | Addressograph Multigraph | Diazotype materials |
| US4220805A (en) * | 1978-09-18 | 1980-09-02 | General Electric Company | Linear dimers of bisphenols and method for making |
| US5569568A (en) * | 1994-12-16 | 1996-10-29 | Eastman Kodak Company | Method for using a laser ablative recording element with low red or green absorption as a reprographic photomask |
| US9243007B2 (en) | 2011-03-30 | 2016-01-26 | Asahi Kasei Chemicals Corporation | Organopolysiloxane, method for producing the same, and curable resin composition containing the organopolysiloxane |
Also Published As
| Publication number | Publication date |
|---|---|
| BE564689A (en, 2012) | |
| DE1068556B (en, 2012) | 1959-11-05 |
| GB840945A (en) | 1960-07-13 |
| NL97385C (en, 2012) | |
| CH375988A (de) | 1964-03-15 |
| NL225064A (en, 2012) |
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