DE2314199A1 - Lichtempfindliche diazoniumsalze - Google Patents
Lichtempfindliche diazoniumsalzeInfo
- Publication number
- DE2314199A1 DE2314199A1 DE19732314199 DE2314199A DE2314199A1 DE 2314199 A1 DE2314199 A1 DE 2314199A1 DE 19732314199 DE19732314199 DE 19732314199 DE 2314199 A DE2314199 A DE 2314199A DE 2314199 A1 DE2314199 A1 DE 2314199A1
- Authority
- DE
- Germany
- Prior art keywords
- diazonium
- hexafluoroarsenate
- ecm
- substituted
- group
- 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
- 239000012954 diazonium Substances 0.000 title claims description 33
- 150000001989 diazonium salts Chemical class 0.000 title claims description 15
- -1 4-amino-substituted benzenediazonium part Chemical class 0.000 claims description 105
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 10
- 239000011248 coating agent Substances 0.000 claims description 8
- 238000000576 coating method Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 229910052787 antimony Inorganic materials 0.000 claims description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- DJHGAFSJWGLOIV-UHFFFAOYSA-K Arsenate3- Chemical compound [O-][As]([O-])([O-])=O DJHGAFSJWGLOIV-UHFFFAOYSA-K 0.000 claims description 2
- 229940000489 arsenate Drugs 0.000 claims description 2
- 229910052785 arsenic Inorganic materials 0.000 claims description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002780 morpholines Chemical class 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 150000003053 piperidines Chemical class 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 27
- 239000000203 mixture Substances 0.000 description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 23
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 22
- 235000002639 sodium chloride Nutrition 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 238000009472 formulation Methods 0.000 description 16
- 150000003839 salts Chemical class 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 15
- 150000008049 diazo compounds Chemical class 0.000 description 14
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 229910021529 ammonia Inorganic materials 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 10
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 6
- 229920001747 Cellulose diacetate Polymers 0.000 description 6
- 229920002284 Cellulose triacetate Polymers 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 5
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 5
- 229920002301 cellulose acetate Polymers 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 229920000139 polyethylene terephthalate Polymers 0.000 description 5
- 239000005020 polyethylene terephthalate Substances 0.000 description 5
- 239000001119 stannous chloride Substances 0.000 description 5
- 235000011150 stannous chloride Nutrition 0.000 description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 238000002845 discoloration Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000002966 varnish Substances 0.000 description 4
- 235000005074 zinc chloride Nutrition 0.000 description 4
- 239000011592 zinc chloride Substances 0.000 description 4
- GKXUAYXGWHRFKD-UHFFFAOYSA-N 1-chloro-4-nitro-2-phenoxybenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(OC=2C=CC=CC=2)=C1 GKXUAYXGWHRFKD-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical class O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 206010070834 Sensitisation Diseases 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 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
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000008313 sensitization Effects 0.000 description 3
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 3
- 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 2
- NMFFUUFPJJOWHK-UHFFFAOYSA-N 2-phenoxyaniline Chemical compound NC1=CC=CC=C1OC1=CC=CC=C1 NMFFUUFPJJOWHK-UHFFFAOYSA-N 0.000 description 2
- UYEMGAFJOZZIFP-UHFFFAOYSA-N 3,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(O)=C1 UYEMGAFJOZZIFP-UHFFFAOYSA-N 0.000 description 2
- SKWRCBCRAMCCHZ-UHFFFAOYSA-N 3-methylbenzenediazonium Chemical compound CC1=CC=CC([N+]#N)=C1 SKWRCBCRAMCCHZ-UHFFFAOYSA-N 0.000 description 2
- TYSZFIGXNURICC-UHFFFAOYSA-N 4-(diethylamino)-2-(trifluoromethyl)benzenediazonium Chemical compound CCN(CC)C1=CC=C([N+]#N)C(C(F)(F)F)=C1 TYSZFIGXNURICC-UHFFFAOYSA-N 0.000 description 2
- RGCITEKHKXPDDH-UHFFFAOYSA-N 4-(diethylamino)benzenediazonium Chemical compound CCN(CC)C1=CC=C([N+]#N)C=C1 RGCITEKHKXPDDH-UHFFFAOYSA-N 0.000 description 2
- CGQKBVHAWXBMCL-UHFFFAOYSA-N 4-nitro-2-phenoxyaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1OC1=CC=CC=C1 CGQKBVHAWXBMCL-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- MBAKFIZHTUAVJN-UHFFFAOYSA-I hexafluoroantimony(1-);hydron Chemical compound F.F[Sb](F)(F)(F)F MBAKFIZHTUAVJN-UHFFFAOYSA-I 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- KOHNUEXAOQRRPI-UHFFFAOYSA-N n-benzyl-3-oxobutanamide Chemical compound CC(=O)CC(=O)NCC1=CC=CC=C1 KOHNUEXAOQRRPI-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000001235 sensitizing effect Effects 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- LXYVGWKSTBBYSH-UHFFFAOYSA-N 1-(4-nitro-2-phenoxyphenyl)piperidine Chemical compound C=1C=CC=CC=1OC1=CC([N+](=O)[O-])=CC=C1N1CCCCC1 LXYVGWKSTBBYSH-UHFFFAOYSA-N 0.000 description 1
- VYQOFWHOCURTBK-UHFFFAOYSA-N 1-(4-nitro-2-phenoxyphenyl)pyrrolidine Chemical compound C=1C=CC=CC=1OC1=CC([N+](=O)[O-])=CC=C1N1CCCC1 VYQOFWHOCURTBK-UHFFFAOYSA-N 0.000 description 1
- NJLLALPCADBTIS-UHFFFAOYSA-N 2,5-dibutoxy-4-morpholin-4-ylbenzenediazonium Chemical compound C1=C([N+]#N)C(OCCCC)=CC(N2CCOCC2)=C1OCCCC NJLLALPCADBTIS-UHFFFAOYSA-N 0.000 description 1
- WSXBITZHDGHHQD-UHFFFAOYSA-N 2-(ethylamino)-5-methylbenzenediazonium Chemical compound CCNC1=CC=C(C)C=C1[N+]#N WSXBITZHDGHHQD-UHFFFAOYSA-N 0.000 description 1
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 description 1
- NIPHBNBAJWTWQA-UHFFFAOYSA-N 2-methylbenzenediazonium Chemical compound CC1=CC=CC=C1[N+]#N NIPHBNBAJWTWQA-UHFFFAOYSA-N 0.000 description 1
- TWVXFNXKFRBILS-UHFFFAOYSA-N 2-nitro-1-(2-nitro-3-phenylphenoxy)-3-phenylbenzene Chemical compound C1=CC=C(C=2C=CC=CC=2)C([N+](=O)[O-])=C1OC(C=1[N+]([O-])=O)=CC=CC=1C1=CC=CC=C1 TWVXFNXKFRBILS-UHFFFAOYSA-N 0.000 description 1
- HBICMRZCQLNXRU-UHFFFAOYSA-N 3,5-dihydroxy-n-(2-hydroxyethyl)benzamide Chemical compound OCCNC(=O)C1=CC(O)=CC(O)=C1 HBICMRZCQLNXRU-UHFFFAOYSA-N 0.000 description 1
- AQYMRQUYPFCXDM-UHFFFAOYSA-N 3-hydroxy-n-(2-methoxyphenyl)naphthalene-2-carboxamide Chemical compound COC1=CC=CC=C1NC(=O)C1=CC2=CC=CC=C2C=C1O AQYMRQUYPFCXDM-UHFFFAOYSA-N 0.000 description 1
- GEHZXBFGTXGYLU-UHFFFAOYSA-N 3-phenoxy-4-piperidin-1-ylaniline Chemical compound C=1C=CC=CC=1OC1=CC(N)=CC=C1N1CCCCC1 GEHZXBFGTXGYLU-UHFFFAOYSA-N 0.000 description 1
- LPSOYBMSIFJAQF-UHFFFAOYSA-N 3-phenoxy-4-pyrrolidin-1-ylaniline;hydrochloride Chemical compound Cl.C=1C=CC=CC=1OC1=CC(N)=CC=C1N1CCCC1 LPSOYBMSIFJAQF-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
- YFCXTPKUVYRXFI-UHFFFAOYSA-M 4-(diethylamino)benzenediazonium;chloride Chemical compound [Cl-].CCN(CC)C1=CC=C([N+]#N)C=C1 YFCXTPKUVYRXFI-UHFFFAOYSA-M 0.000 description 1
- MOXBCYIWIODTKI-UHFFFAOYSA-N 4-(dimethylamino)benzenediazonium Chemical compound CN(C)C1=CC=C([N+]#N)C=C1 MOXBCYIWIODTKI-UHFFFAOYSA-N 0.000 description 1
- CYOTVRXTHZXYAN-UHFFFAOYSA-M 4-anilino-2-methoxybenzenediazonium;chloride Chemical compound [Cl-].C1=C([N+]#N)C(OC)=CC(NC=2C=CC=CC=2)=C1 CYOTVRXTHZXYAN-UHFFFAOYSA-M 0.000 description 1
- CFPIGEXZPWTNOR-UHFFFAOYSA-N 4-chloro-1-nitro-2-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1C(F)(F)F CFPIGEXZPWTNOR-UHFFFAOYSA-N 0.000 description 1
- NJYDJNRTEZIUBS-UHFFFAOYSA-N 4-morpholin-4-ylbenzenediazonium Chemical compound C1=CC([N+]#N)=CC=C1N1CCOCC1 NJYDJNRTEZIUBS-UHFFFAOYSA-N 0.000 description 1
- LRJPHOYHNHKIGI-UHFFFAOYSA-M 4-piperidin-1-ylbenzenediazonium;chloride Chemical compound [Cl-].C1=CC([N+]#N)=CC=C1N1CCCCC1 LRJPHOYHNHKIGI-UHFFFAOYSA-M 0.000 description 1
- NNWHYXOGAWBBEZ-UHFFFAOYSA-M 4-pyrrolidin-1-ylbenzenediazonium;chloride Chemical compound [Cl-].C1=CC([N+]#N)=CC=C1N1CCCC1 NNWHYXOGAWBBEZ-UHFFFAOYSA-M 0.000 description 1
- WVFXZZVKIWIJHR-UHFFFAOYSA-N 5-(ethylamino)-2-methylbenzenediazonium Chemical compound CCNC1=CC=C(C)C([N+]#N)=C1 WVFXZZVKIWIJHR-UHFFFAOYSA-N 0.000 description 1
- NETZMTSGBRMNPZ-UHFFFAOYSA-N 5-methyl-2-pyrrolidin-1-ylbenzenediazonium Chemical compound N#[N+]C1=CC(C)=CC=C1N1CCCC1 NETZMTSGBRMNPZ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- AEAMTEXGRVEEIH-UHFFFAOYSA-N C1(=C(C=CC=C1)OOC1=C(C=CC=C1)O)O.C=C Chemical compound C1(=C(C=CC=C1)OOC1=C(C=CC=C1)O)O.C=C AEAMTEXGRVEEIH-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- ZCHPKWUIAASXPV-UHFFFAOYSA-N acetic acid;methanol Chemical compound OC.CC(O)=O ZCHPKWUIAASXPV-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 125000005615 azonium group Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- MKWIUUISIFXUPZ-UHFFFAOYSA-N n-(2-phenoxyphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC=C1OC1=CC=CC=C1 MKWIUUISIFXUPZ-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- DOKHEARVIDLSFF-UHFFFAOYSA-N prop-1-en-1-ol Chemical compound CC=CO DOKHEARVIDLSFF-UHFFFAOYSA-N 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- G03C1/54—Diazonium salts or diazo anhydrides
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/237,890 US3957489A (en) | 1968-09-11 | 1972-03-24 | Solvent soluble diazonium metal salts and diazotype materials therefor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2314199A1 true DE2314199A1 (de) | 1973-10-04 |
Family
ID=22895673
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732314199 Pending DE2314199A1 (de) | 1972-03-24 | 1973-03-22 | Lichtempfindliche diazoniumsalze |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS525846B2 (enrdf_load_stackoverflow) |
| AU (1) | AU465206B2 (enrdf_load_stackoverflow) |
| CA (1) | CA994329A (enrdf_load_stackoverflow) |
| CH (1) | CH549229A (enrdf_load_stackoverflow) |
| DE (1) | DE2314199A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2177852B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1362358A (enrdf_load_stackoverflow) |
| IT (1) | IT994853B (enrdf_load_stackoverflow) |
| NL (1) | NL7303859A (enrdf_load_stackoverflow) |
| ZA (1) | ZA73770B (enrdf_load_stackoverflow) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL233064A (enrdf_load_stackoverflow) * | 1958-11-10 | |||
| US3203803A (en) * | 1964-01-20 | 1965-08-31 | Tecnifax Corp | Light-sensitive diazo hexafluoro-phosphate compositions |
-
1973
- 1973-02-01 CA CA162,584A patent/CA994329A/en not_active Expired
- 1973-02-02 ZA ZA730770A patent/ZA73770B/xx unknown
- 1973-02-07 AU AU51917/73A patent/AU465206B2/en not_active Expired
- 1973-02-08 GB GB633173A patent/GB1362358A/en not_active Expired
- 1973-02-22 IT IT20732/73A patent/IT994853B/it active
- 1973-03-15 JP JP48030446A patent/JPS525846B2/ja not_active Expired
- 1973-03-20 NL NL7303859A patent/NL7303859A/xx unknown
- 1973-03-22 DE DE19732314199 patent/DE2314199A1/de active Pending
- 1973-03-22 FR FR7310251A patent/FR2177852B1/fr not_active Expired
- 1973-03-22 CH CH416073A patent/CH549229A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2177852B1 (enrdf_load_stackoverflow) | 1977-04-29 |
| NL7303859A (enrdf_load_stackoverflow) | 1973-09-26 |
| CH549229A (de) | 1974-05-15 |
| ZA73770B (en) | 1974-09-25 |
| JPS525846B2 (enrdf_load_stackoverflow) | 1977-02-17 |
| IT994853B (it) | 1975-10-20 |
| CA994329A (en) | 1976-08-03 |
| JPS4915424A (enrdf_load_stackoverflow) | 1974-02-09 |
| FR2177852A1 (enrdf_load_stackoverflow) | 1973-11-09 |
| AU465206B2 (en) | 1975-09-18 |
| AU5191773A (en) | 1974-08-08 |
| GB1362358A (en) | 1974-08-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE825204C (de) | Lichtempfindliches Material fuer das Diazotypieverfahren | |
| DE1086123B (de) | Einkomponenten-Diazotypiematerial | |
| DE1236331B (de) | Zweikomponenten-Diazotypiematerial | |
| EP0017699B1 (de) | Derivate des 2-Hydroxy-naphthalins und Diazotypiematerial, das diese als Kupplungskomponente enthält | |
| EP0004574B1 (de) | 2-Hydroxy-3-naphthoesäureamide und deren Verwendung als Kupplungskomponenten in Diazotypiematerialien | |
| DE2314199A1 (de) | Lichtempfindliche diazoniumsalze | |
| DE2609565C2 (de) | Aufzeichnungsverfahren zur Erzeugung eines positiven Bildes | |
| DE1447733B2 (de) | 2-(3,5-dihydroxyphenyl)-benzimidazolderivate | |
| DE1770074C3 (enrdf_load_stackoverflow) | ||
| EP0118846B1 (de) | Zweikomponenten-Diazotypiematerial | |
| DE2553136B2 (de) | Zweikomponenten-Diazotypiematerial | |
| DE1962391C2 (de) | Benzoldiazoniumverbindungen und deren Verwendung | |
| US3957489A (en) | Solvent soluble diazonium metal salts and diazotype materials therefor | |
| DE1944915A1 (de) | Diazoniumhexafluorarsenate und -antimonate und ihre Verwendung in Diazotypiematerial | |
| DE896453C (de) | Azokomponenten fuer die Diazotypie | |
| EP0161655B1 (de) | Lichtempfindliches Gemisch und hiermit hergestelltes Zweikomponenten-Diazotypiematerial | |
| EP0008472B1 (de) | Lichtempfindliche Benzoldiazoniumsalze und Diazotypiematerial unter Verwendung derselben | |
| DE1911491C3 (de) | Lichtempfindliche Diazoniumsalze, Verfahren zu ihrer Herstellung und sie enthaltendes Diazotypie-Kopiermaterial | |
| DE1793342C3 (de) | Fluorhaltige Benzoldiazoniumverbindungen und deren Verwendung in Diazotypiematerial | |
| DE1572098C3 (enrdf_load_stackoverflow) | ||
| DE1900857A1 (de) | Lichtempfindliche Diazoniumverbindungen fuer das Diazotypie-Photoreproduktionsverfahren | |
| DE1572098B2 (de) | Benzoldiazoniumverbindungen | |
| DE1572084C3 (de) | Verfahren zur Herstellung von Diazotypiekopien mit roten Linien | |
| DE1797621C3 (de) | Diazotypiematerial | |
| EP0001617A1 (de) | Diazotypiematerial |