DE2061239A1 - Diazo-Aufzeichnungsverfahren - Google Patents
Diazo-AufzeichnungsverfahrenInfo
- Publication number
- DE2061239A1 DE2061239A1 DE19702061239 DE2061239A DE2061239A1 DE 2061239 A1 DE2061239 A1 DE 2061239A1 DE 19702061239 DE19702061239 DE 19702061239 DE 2061239 A DE2061239 A DE 2061239A DE 2061239 A1 DE2061239 A1 DE 2061239A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- diazo
- compound
- recording material
- diazonium
- 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.)
- Pending
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 20
- 150000001989 diazonium salts Chemical class 0.000 claims description 23
- -1 benzothiazolium compound Chemical class 0.000 claims description 22
- 239000000463 material Substances 0.000 claims description 17
- 150000008049 diazo compounds Chemical class 0.000 claims description 13
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 239000012954 diazonium Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 238000006193 diazotization reaction Methods 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 150000003142 primary aromatic amines Chemical class 0.000 claims description 3
- 238000005956 quaternization reaction Methods 0.000 claims description 3
- 125000001302 tertiary amino group Chemical group 0.000 claims description 3
- 235000005074 zinc chloride Nutrition 0.000 claims description 3
- 239000011592 zinc chloride Substances 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 238000003384 imaging method Methods 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000000975 dye Substances 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZJMSXVSGTCVBQK-UHFFFAOYSA-N I.I.I.I.I.I.I Chemical compound I.I.I.I.I.I.I ZJMSXVSGTCVBQK-UHFFFAOYSA-N 0.000 description 3
- RCZNYTXJVULKCR-UHFFFAOYSA-N I.I.I.I.I.I.I.I Chemical compound I.I.I.I.I.I.I.I RCZNYTXJVULKCR-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- DXYYSGDWQCSKKO-UHFFFAOYSA-N methylbenzothiazole Chemical class C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical class C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- ZZLZXZFVVOXVRG-UHFFFAOYSA-N 2,5,6-trimethyl-1,3-benzothiazole Chemical class CC1=C(C)C=C2SC(C)=NC2=C1 ZZLZXZFVVOXVRG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VZWOXDYRBDIHMA-UHFFFAOYSA-N 2-methyl-1,3-thiazole Chemical class CC1=NC=CS1 VZWOXDYRBDIHMA-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- HLHNOIAOWQFNGW-UHFFFAOYSA-N 3-bromo-4-hydroxybenzonitrile Chemical compound OC1=CC=C(C#N)C=C1Br HLHNOIAOWQFNGW-UHFFFAOYSA-N 0.000 description 1
- DEAHHKWRGZEJBW-UHFFFAOYSA-N 3-methyl-2-methylidene-1,3-benzothiazole Chemical class C1=CC=C2N(C)C(=C)SC2=C1 DEAHHKWRGZEJBW-UHFFFAOYSA-N 0.000 description 1
- HYXQCNIDWFATGE-UHFFFAOYSA-N 3-phenylmorpholin-4-amine Chemical compound NN1C(COCC1)C1=CC=CC=C1 HYXQCNIDWFATGE-UHFFFAOYSA-N 0.000 description 1
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 description 1
- NDFBOKSIVYNZSI-UHFFFAOYSA-N 4-n-benzyl-4-n-ethylbenzene-1,4-diamine Chemical compound C=1C=C(N)C=CC=1N(CC)CC1=CC=CC=C1 NDFBOKSIVYNZSI-UHFFFAOYSA-N 0.000 description 1
- SAQMNBWVOKYKPZ-UHFFFAOYSA-N 5-methoxy-2-methyl-1,3-benzothiazole Chemical class COC1=CC=C2SC(C)=NC2=C1 SAQMNBWVOKYKPZ-UHFFFAOYSA-N 0.000 description 1
- BGSRFMFTXMPTSC-UHFFFAOYSA-N 6-fluoro-1,3-benzothiazole Chemical class FC1=CC=C2N=CSC2=C1 BGSRFMFTXMPTSC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920000742 Cotton Polymers 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
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ADLSWZDEMJETGK-UHFFFAOYSA-N I.I.I.I.I.I.I.I.I.I.I Chemical compound I.I.I.I.I.I.I.I.I.I.I ADLSWZDEMJETGK-UHFFFAOYSA-N 0.000 description 1
- SWRBSUXHONHMHY-UHFFFAOYSA-M S(=O)(=O)(OC)[O-].CC=1SC2=C([N+]1C)C=C(C(=C2)C)C Chemical compound S(=O)(=O)(OC)[O-].CC=1SC2=C([N+]1C)C=C(C(=C2)C)C SWRBSUXHONHMHY-UHFFFAOYSA-M 0.000 description 1
- 206010070834 Sensitisation Diseases 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
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- JLSJUVBUAOGHRO-UHFFFAOYSA-L [Na+].C1(=C(C(=CC2=CC=CC=C12)S(=O)(=O)O)S(=O)(=O)[O-])S(=O)(=O)[O-].[Na+] Chemical compound [Na+].C1(=C(C(=CC2=CC=CC=C12)S(=O)(=O)O)S(=O)(=O)[O-])S(=O)(=O)[O-].[Na+] JLSJUVBUAOGHRO-UHFFFAOYSA-L 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 235000016720 allyl isothiocyanate Nutrition 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 125000006278 bromobenzyl group Chemical group 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- JCVWJTABEYRYND-UHFFFAOYSA-L disodium 4-sulfonaphthalene-2,7-disulfonate Chemical compound [Na+].C1(=CC(=CC2=CC(=CC=C12)S(=O)(=O)O)S(=O)(=O)[O-])S(=O)(=O)[O-].[Na+] JCVWJTABEYRYND-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- JJZAZDAEVNRFGT-MHLYXQECSA-N furaquinocin I Natural products COC1=C(C)C(=O)c2c3O[C@H](C)[C@](C)([C@H](O)CC=C(/C)C(=O)O)c3c(O)cc2C1=O JJZAZDAEVNRFGT-MHLYXQECSA-N 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
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical group C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- MSNFOUCVUZMALD-UHFFFAOYSA-N methyl 2-methyl-1,3-benzothiazole-5-carboxylate Chemical class COC(=O)C1=CC=C2SC(C)=NC2=C1 MSNFOUCVUZMALD-UHFFFAOYSA-N 0.000 description 1
- XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical compound COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- CNXZLZNEIYFZGU-UHFFFAOYSA-N n-(4-amino-2,5-diethoxyphenyl)benzamide Chemical compound C1=C(N)C(OCC)=CC(NC(=O)C=2C=CC=CC=2)=C1OCC CNXZLZNEIYFZGU-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000010944 pre-mature reactiony Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- TYRGSDXYMNTMML-UHFFFAOYSA-N propyl hydrogen sulfate Chemical compound CCCOS(O)(=O)=O TYRGSDXYMNTMML-UHFFFAOYSA-N 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 125000004964 sulfoalkyl group Chemical group 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- RHZZVWTVJHZKAH-UHFFFAOYSA-K trisodium;naphthalene-1,2,3-trisulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(S([O-])(=O)=O)=C(S([O-])(=O)=O)C(S(=O)(=O)[O-])=CC2=C1 RHZZVWTVJHZKAH-UHFFFAOYSA-K 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood 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
- G03C1/00—Photosensitive materials
- G03C1/52—Compositions containing diazo compounds as photosensitive substances
- G03C1/58—Coupling substances therefor
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB6270869 | 1969-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2061239A1 true DE2061239A1 (de) | 1971-07-01 |
Family
ID=10488407
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702061239 Pending DE2061239A1 (de) | 1969-12-23 | 1970-12-12 | Diazo-Aufzeichnungsverfahren |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3676140A (enrdf_load_stackoverflow) |
| JP (1) | JPS4834765B1 (enrdf_load_stackoverflow) |
| BE (1) | BE759935A (enrdf_load_stackoverflow) |
| CA (1) | CA920580A (enrdf_load_stackoverflow) |
| DE (1) | DE2061239A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2073027A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1332459A (enrdf_load_stackoverflow) |
| NL (1) | NL7018257A (enrdf_load_stackoverflow) |
| SU (1) | SU363264A3 (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3985562A (en) * | 1973-05-18 | 1976-10-12 | Agfa-Gevaert N.V. | Diazo recording process and material |
| JPS50137721A (enrdf_load_stackoverflow) * | 1974-04-22 | 1975-11-01 |
-
0
- BE BE759935D patent/BE759935A/xx unknown
-
1969
- 1969-12-23 GB GB6270869A patent/GB1332459A/en not_active Expired
-
1970
- 1970-11-17 CA CA098351A patent/CA920580A/en not_active Expired
- 1970-12-02 US US94575A patent/US3676140A/en not_active Expired - Lifetime
- 1970-12-04 JP JP45107503A patent/JPS4834765B1/ja active Pending
- 1970-12-07 FR FR7044002A patent/FR2073027A5/fr not_active Expired
- 1970-12-12 DE DE19702061239 patent/DE2061239A1/de active Pending
- 1970-12-14 SU SU1602203A patent/SU363264A3/ru active
- 1970-12-15 NL NL7018257A patent/NL7018257A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1332459A (en) | 1973-10-03 |
| BE759935A (fr) | 1971-06-07 |
| US3676140A (en) | 1972-07-11 |
| NL7018257A (enrdf_load_stackoverflow) | 1971-06-25 |
| FR2073027A5 (enrdf_load_stackoverflow) | 1971-09-24 |
| CA920580A (en) | 1973-02-06 |
| JPS4834765B1 (enrdf_load_stackoverflow) | 1973-10-23 |
| SU363264A3 (enrdf_load_stackoverflow) | 1972-12-30 |
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