US2465760A - Diazotype materials derived from aryl diazo sulfones - Google Patents
Diazotype materials derived from aryl diazo sulfones Download PDFInfo
- Publication number
- US2465760A US2465760A US758702A US75870247A US2465760A US 2465760 A US2465760 A US 2465760A US 758702 A US758702 A US 758702A US 75870247 A US75870247 A US 75870247A US 2465760 A US2465760 A US 2465760A
- Authority
- US
- United States
- Prior art keywords
- diazo
- sulfone
- diazotype
- light sensitive
- solution
- 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
- -1 aryl diazo sulfones Chemical class 0.000 title description 51
- 239000000463 material Substances 0.000 title description 18
- 239000000243 solution Substances 0.000 description 39
- 238000005859 coupling reaction Methods 0.000 description 37
- 230000008878 coupling Effects 0.000 description 32
- 238000010168 coupling process Methods 0.000 description 32
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 29
- 239000000987 azo dye Substances 0.000 description 28
- 238000000034 method Methods 0.000 description 23
- 239000011248 coating agent Substances 0.000 description 20
- 238000000576 coating method Methods 0.000 description 20
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 150000008049 diazo compounds Chemical class 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
- 229910021529 ammonia Inorganic materials 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- JRNGUTKWMSBIBF-UHFFFAOYSA-N naphthalene-2,3-diol Chemical compound C1=CC=C2C=C(O)C(O)=CC2=C1 JRNGUTKWMSBIBF-UHFFFAOYSA-N 0.000 description 7
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 206010034960 Photophobia Diseases 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000012954 diazonium Substances 0.000 description 5
- 150000001989 diazonium salts Chemical class 0.000 description 5
- 208000013469 light sensitivity Diseases 0.000 description 5
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 4
- 230000002028 premature Effects 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 150000003254 radicals Chemical group 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- AMTPYFGPPVFBBI-UHFFFAOYSA-N acedapsone Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)C1=CC=C(NC(C)=O)C=C1 AMTPYFGPPVFBBI-UHFFFAOYSA-N 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- GAMPNQJDUFQVQO-UHFFFAOYSA-N acetic acid;phthalic acid Chemical compound CC(O)=O.OC(=O)C1=CC=CC=C1C(O)=O GAMPNQJDUFQVQO-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- MPYXTIHPALVENR-UHFFFAOYSA-N benzene-1,3,5-triol;dihydrate Chemical compound O.O.OC1=CC(O)=CC(O)=C1 MPYXTIHPALVENR-UHFFFAOYSA-N 0.000 description 2
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 229920003086 cellulose ether Polymers 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- MQRJBSHKWOFOGF-UHFFFAOYSA-L disodium;carbonate;hydrate Chemical compound O.[Na+].[Na+].[O-]C([O-])=O MQRJBSHKWOFOGF-UHFFFAOYSA-L 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000003517 fume Substances 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
- OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000001047 purple dye Substances 0.000 description 2
- 239000004627 regenerated cellulose Substances 0.000 description 2
- 229940076133 sodium carbonate monohydrate Drugs 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 230000003381 solubilizing effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- GOHHBFSPKLRUNF-UHFFFAOYSA-N 1-[(dimethylamino)methyl]naphthalen-2-ol Chemical compound C1=CC=C2C(CN(C)C)=C(O)C=CC2=C1 GOHHBFSPKLRUNF-UHFFFAOYSA-N 0.000 description 1
- KRKPRSDJPYNGLE-UHFFFAOYSA-N 2,4-dihydroxybenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(O)C=C1O KRKPRSDJPYNGLE-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
- NJXWZWXCHBNOOG-UHFFFAOYSA-N 3,3-diphenylpropyl(1-phenylethyl)azanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1C(C)[NH2+]CCC(C=1C=CC=CC=1)C1=CC=CC=C1 NJXWZWXCHBNOOG-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
- YDQNDKBOOVXRTL-UHFFFAOYSA-N 4-acetamidobenzenesulfinic acid Chemical compound CC(=O)NC1=CC=C(S(O)=O)C=C1 YDQNDKBOOVXRTL-UHFFFAOYSA-N 0.000 description 1
- XTBFKMDOQMQYPP-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine;hydron;chloride Chemical compound Cl.CCN(CC)C1=CC=C(N)C=C1 XTBFKMDOQMQYPP-UHFFFAOYSA-N 0.000 description 1
- 241000282979 Alces alces Species 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 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
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 1
- ZZXDRXVIRVJQBT-UHFFFAOYSA-M Xylenesulfonate Chemical compound CC1=CC=CC(S([O-])(=O)=O)=C1C ZZXDRXVIRVJQBT-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 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
- 239000011521 glass Substances 0.000 description 1
- 230000003165 hydrotropic effect Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229960004025 sodium salicylate Drugs 0.000 description 1
- 229940048842 sodium xylenesulfonate Drugs 0.000 description 1
- QUCDWLYKDRVKMI-UHFFFAOYSA-M sodium;3,4-dimethylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1C QUCDWLYKDRVKMI-UHFFFAOYSA-M 0.000 description 1
- KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 description 1
- UHJBUYLXLTVQRO-UHFFFAOYSA-M sodium;acetate;dihydrate Chemical compound O.O.[Na+].CC([O-])=O UHJBUYLXLTVQRO-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229940071104 xylenesulfonate Drugs 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
- G03C1/56—Diazo sulfonates
Definitions
- the aromatic diazo compound is incorporated into the light sensitive layer of thecar rier, which may be opaque or transparentized paper, films such as cellulose ester or cellulose ether film, regenerated cellulose bodies, ceram c surfaces, glass, metallic or wood surfaces, and after exposure under the orig nal pa tern. to be copied the undecomposed aromat c diazo compound is developed by contacting the exposed layer with a solut on of the coupling component necessary to produce the ultimately desired image.
- the developing solution containing the coupling component should be alkaline.
- diazo compounds which are 8 Claims. (Cl. 95-7) developable in acid solution and in such cases the solution of the coupler will be acid.
- the aromatic diazo compound and the coupling component necessary to 1 produce the dye image are both incorporated in the light sensitive layer on the carrier. In this case, development of the dye image is eifected after exposure by contacting the exposed light sensitive layer with ammonia fumes.
- diazo compounds For optimum results in the two-component process, it is necessary to limit the selection of diazo compounds to those which will be inert to reaction with the coupling component while in the coating solution and the light sensitive layer prior to development.
- the most satisfactory diazo compounds for this purpose have been found to be those which are derived from aromatic p-diamines and o-aminonaphthols; A few others have been found suitable, particularly when addition agents are employed which tend to retard the coupling function. For the most part, however, premature coupling of the dye components takes place when other types of diazo compounds are used.
- This class of compounds may be designated as the diazo sulfones. They are incapable of coupling with azo dye coupling components in the absence of the alkaline coupling medium and hence, like the N-nitroso-N-arylamides of Patent 2,411,811, two-component light sensitive layers produced from these diazo sultones can be stored indefinitely without danger oi precoupling of the dye components taking place under ordinary conditions of storage.
- the diazo sulfones of this invention will couple readily with azo dye coupling components in the presence of an alkaline medium, such as ammonia iumes, to produce an azo dye image in any desired color.
- R represents a radical derived from a compound having an aromatic character such as benzene, naphthalene, anthracene, quinoline, carbazole, indole and the like
- R represents a radical derived from a compound having an aromatic character as above or from a compound having an aliphatic character such as methane, ethane, butane, pentane, hexane, cyclohexane, methylcyclohexane, octane, decane, dodecane, hexadecane, octadecane and the like.
- the diazo sulfones may have certain substituents on the aromatic nuclei, R.
- benzylamino such as benzylamino; heterocyclic amino, such as and Z-pyridylamino; alkyl, such as methyl, ethyl, butyl, lauryl and octadecyl; alkoxy, such as methoxy and butoxy;
- aryioxy such as phenoxy
- aliphatic acylamino such as acetamido
- aromatic acylamino such as benzamido
- the diazo sulfones may be represented by the general formula wherein R and R represent radicals derived irmn compounds of an aromatic character as defined above, x has the same meaning as above and Y represents a member of the class consisting of allwlamino, such as methylamino, diethylamino, p,p'-dihydroxyethylamino and N-methyl- N-fl-hydroxyethylamino groups; arylamino, such as phenylamino; aralkylamino, such as benzylamino; heterocyclic amino, such as 2-benzothiazolylamino and 2-pyridylamino; alkyl, such as methyl, ethyl, butyl, lauryl and octadecyl; alkoxy, such as methoxy and butoxy; aryloxy, such as phenoxy; aliphatic acylamino, such as acetamido;
- X and Y may contain solubilizing groups such as sulfo, carboxy and polyoxyethylene groups.
- the diazo sulfones in general, are prepared by the reaction of a diazo compound with a sulilnic acid, oxidation of a fl-aryl sulfonhydrazide, condensation of a diazonium salt with a sulfonamide or decomposition of a diazo thiosulfate.
- Schematic reactions for these processes of preparing the diazo sulfones are as follows:
- RN N-SOzR'+HX 4.
- Decomposition of a diazothiosulionate RN N+X-+KSSO:R'
- Suitable aryldlazosulfones include diphenylamine 4 diazo (p-aminophenyl) -sulione, 4--(N-ethyl-N-benzylamino) -benzenedlazo- (p-aminophenyl) -sulfone, 4-morpholinobenzenediazo- (p-aminophenyl) -sulfone, p- (N-methyl-N- fl-hydroxyethylamino) -benzenediazo (p-aminophenyl) -sulfone, 2,5-dimethoxy 4 benzamidobenzenediazo- (p-acetaminophenyl) -sulfone, 2,5- dimethoxy 4 benzamidobenzenediazo- (p-methtile amines or solutions of mild alkalis,
- Examples of coupling components which may be utilized with the diazo suliones in this process are 2,3-dihydroxynaphthalene, resorcinol, phloroglucinol, p-naphthol, a-naphthol, 3,5-dimethylphenol, 2,4-dihydroxybenzenesulfonamide, 1 phenyl-3-methylpyrazolone-5, acetoacetanilide, 5-methyl resorcinol, 1-dimethylaminomethyl-2- naphthol, 3-(fl-dimethylaminoethoxy) -naphthol- 2, esters of phloroglueinol monocarboxylic acid, and the couplers disclosed in United States Patents 1,822,065, 1,989,065, 2,150,565, 2,196,950, 2,212,959, 2,333,038, 2,245,628, 2,246,425 and 2,286,656.
- the process of this invention is carried out by coating a suitable base, such as paper, a cellulose ester, cellulose ether or regenerated cellulose film, a ceramic material, a textile material, a gelatinized surface or a metallic surface with a coating preparation containing the diazo sulfone compound.
- a suitable base such as paper, a cellulose ester, cellulose ether or regenerated cellulose film, a ceramic material, a textile material, a gelatinized surface or a metallic surface
- an azo dye coupling component such as one of the coupling components mentioned above, a mild acid such as citric, tartaric, acetic, oxalic, maleic acid or a strong acid such as sulfosalicylic acid and a solvent.
- the diazosulione unlike the corresponding diazonium salts, are soluble in water-miscible organic solvents such as acetone, methyl ethyl ketone, methanol, ethanol, isopropanol and the coating mixture can, therefore, be applied in the form of solutions in such solvents or aqueous mixtures thereof.
- the coating mixtures can also be applied to the base in the form of their water solutions if the diazo sulfone contains water solubilizing groups or if the coating mixture contains a hydrotropic reagent, such as sodium toluenesulfonate, potassium xylenesulfonate, sodium cymenesulfonate, sodium salicylate and the like.
- the coating of the selected support is efiected in the usual manner by applying the coating solution to the surface of the carrier with a trough and doctor blade or by spraying.
- the coated material is then dried and exposed under original positive or negative picture or drawing and developed by treatment with ammonia vapor or other suitable alkaline materials, such as v0 1 e coating medium or vehicle for the application of the light sensitive layer, in addition to water and organic solvents, may be an aqueous gelatin or a resinous material such as cellulose acetate hydrogen phthalate suitably liquefied by organic solvents or otherwise for coating purposes.
- the coupling reaction in the case of the diazo suli'ones is a direct action which takes place readily in the presence of proper alkaline coupling medium. The exact mechanism of the coupling reaction is not definitely known.
- Example 1 A diazotype paper stock was coated with a coating solution of the following composition 1.0 gram 2,5-diethoxy-4-benzamidobenzenediazo (p-acetamidophenyl) -sulfone O CzHe I c-mc ONHQNm-S OQNHC 0 on,
- the 2,5-diethoxy 4 benzamidobenzsnediazo- (p-acetamidophenyl) -sulfone may be obtained by diazotizing a suspension of 8.4 grams (0.025 mol) of 2,5-diethoxyi-benzamidoaniline hydrochloride in 2.0 cc. concentrated hydrochloric acid, 8.0 cc. formic acid and cc. water with a solution of 1.8 grams (0.026 mol) sodium nitrite in 10 cc. water.
- Example 2 A diazotype paper stock was coated with a resinous coating solution of the following composition:
- Example 3 A coating solution for a diazotype was made up as follows:
- the combined solution was coated on a diazotype paper stock and allowed to dry.
- the thus diazotype sensitized paper consisting of a resinous layer of the cellulose acetate butyrate carrying the diazosulfone and the coupling component on the paper support was exposed under a positive original pattern and the image developed after exposure by contacting the exposed surface with ammonia vapors. The image of the original was developed to a purple azo dye.
- the 4 -diethylaminobenzenediazo (p-amlnophenyl) -sulfone of this example may be obtained as follows. A solution of 20.0 grams (0.1 mol) p-diethylaminoaniline hydrochloride in 75.0 00. water and 20.0 cc. concentrated hydrochloric acid is diazotized with a solution of 6.9 grams (0.1 mol) sodium nitrite in 75.0 cc. water. This solution is then poured into a solution of 15.7 grams (0.1 mol) 4-aminobenzene sulflnic acid, 6.2 grams (0.05 mol) sodium carbonate monohydrate, 41.0 grams (0.3 mol) sodium acetate dihydrate and 250.0 cc. water. The resulting mixture is allowed to remain overnight in a refrigerator and the following day the orange color precipitate is removed by filtration,
- a diazotype coating solution was prepared in the following manner:
- the combined solution was coated on a sheet of diazotype paper stock and dried.
- the image of the original was reproduced in a brown azo dye.
- Example 6 A diazotype coating solution was prepared as follows:
- the combined solution was coated on a sheet of diazotype paper stock and dried.
- the thus sensitized diazotype was exposed under a positive original design and processed in the same manner as in the case of Example 4.
- a redorange azo dye image was produced.
- Example 7 A diazotype coating solution was prepared as follows:
- the combined solution was coated on a sheet of diazotype paper stock and dried.
- the thus sensitized diazotype was exposed under a positive original design and processed in the same manner as in Example 4.
- a yellow azo dye image was produced.
- Example 8 A diazotype coating solution was made up in the following manner:
- the combined solution was coated on a sheet of diazotype paper stock and dried. It was then exposed under a positive original design to ultraviolet radiations and developed by passing the exposed surface through a chamber containing ammonia fumes with which the exposed surface was brought into contact. The image of the original was reproduced in a reddish-purple azo dye.
- Dlaaotype photoprinting materials compris- 10 ing as the light sensitive element a light sensitive diazo sulfone of the following formula wherein R is an aromatic radical and R is a member of the group consisting of aromatic and aliphatic radicals.
- Diazotype photoprinting materials comprising as the light sensitive element a light sensitive diazo sulfone of the following formula wherein R and R are aromatic radicals.
- Diazotype photoprinting materials comprising as the light sensitive element a light sensitive diazo sulfone of the following formula wherein R and R are aromatic radicals and an azo dye coupling component.
- Diazotype photoprinting materials comprising a light sensitive layer on a suitable carrier, said light sensitive layer containing as the light sensitive element a diazo sulfone of the following formula wherein R and R are aromatic radicals and an azo dye coupling component.
- Diazotype photoprinting materials comprising a resinous layer on a paper carrier, said resinous layer containing as a light sensitive element a diazo sulfone of the following formula wherein R and R are aromatic radicals together with an azo dye coupling component.
- Diazotype photoprinting materials comprising a light sensitive layer on a. suitable carrier, said light sensitive layer containing 2,5- diethoxy- 4-benzamidodiazo-(p-acetamidophenyl) sulfone as the light sensitive element and an azo dye coupling component.
- Diazotype photoprinting materials comprising a light sensitive layer on a suitable carrier. said light sensitive layer containing 4-diethylaminobenzenediazo-(p-aminophenyl)-sulfone as the light sensitive element and an azo dye coupling component.
- Dlaaotype photoprinting materials comprising a light sensitive layer on a suitable carrier, said light sensitive layer containing d-morpholinobenzenediaso-(p-aminophenyll-sulfone as the light sensitive element and an azo dye coupling component.
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- 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)
- Thiazole And Isothizaole Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE483794D BE483794A (en(2012)) | 1947-07-02 | ||
| NL686816496A NL141017B (nl) | 1947-07-02 | Flexibele elektrische contactkabel. | |
| NL66139D NL66139C (en(2012)) | 1947-07-02 | ||
| US758702A US2465760A (en) | 1947-07-02 | 1947-07-02 | Diazotype materials derived from aryl diazo sulfones |
| GB15165/48A GB649604A (en) | 1947-07-02 | 1948-06-04 | Diazotype photoprinting materials sensitized with aryl diazo sulfones |
| FR988484D FR988484A (fr) | 1947-07-02 | 1948-06-28 | Matériel d'impression photographique diazotype et procédé pour son obtention |
| CH279648D CH279648A (fr) | 1947-07-02 | 1948-07-02 | Procédé pour la préparation d'un matériel diazotype pour photocopie et matériel obtenu par ce procédé. |
| DEP29262D DE815301C (de) | 1947-07-02 | 1949-01-01 | Verfahren zur Herstellung von Kopien auf Diazotypiematerial |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US758702A US2465760A (en) | 1947-07-02 | 1947-07-02 | Diazotype materials derived from aryl diazo sulfones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2465760A true US2465760A (en) | 1949-03-29 |
Family
ID=25052753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US758702A Expired - Lifetime US2465760A (en) | 1947-07-02 | 1947-07-02 | Diazotype materials derived from aryl diazo sulfones |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US2465760A (en(2012)) |
| BE (1) | BE483794A (en(2012)) |
| CH (1) | CH279648A (en(2012)) |
| DE (1) | DE815301C (en(2012)) |
| FR (1) | FR988484A (en(2012)) |
| GB (1) | GB649604A (en(2012)) |
| NL (2) | NL141017B (en(2012)) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2529029A (en) * | 1946-04-24 | 1950-11-07 | Francolor Sa | Diazotypes containing diazosulfonates |
| US2792303A (en) * | 1951-09-19 | 1957-05-14 | Grinten Chem L V D | Process for the production of diazotype copies |
| US3113865A (en) * | 1960-05-05 | 1963-12-10 | Eastman Kodak Co | Heat developable diazo sulfones |
| US3338711A (en) * | 1962-11-15 | 1967-08-29 | Du Pont | Process for forming azo dye photographic images |
| US3340059A (en) * | 1963-02-27 | 1967-09-05 | Du Pont | Diffusion transfer process for producing silver-free azo dye images |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1628279A (en) * | 1924-05-28 | 1927-05-10 | Kalle & Co Ag | Sensitive layer on alpha suitable base and process of making same |
| US2117451A (en) * | 1938-05-17 | robertson |
-
0
- NL NL66139D patent/NL66139C/xx active
- NL NL686816496A patent/NL141017B/xx unknown
- BE BE483794D patent/BE483794A/xx unknown
-
1947
- 1947-07-02 US US758702A patent/US2465760A/en not_active Expired - Lifetime
-
1948
- 1948-06-04 GB GB15165/48A patent/GB649604A/en not_active Expired
- 1948-06-28 FR FR988484D patent/FR988484A/fr not_active Expired
- 1948-07-02 CH CH279648D patent/CH279648A/fr unknown
-
1949
- 1949-01-01 DE DEP29262D patent/DE815301C/de not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2117451A (en) * | 1938-05-17 | robertson | ||
| US1628279A (en) * | 1924-05-28 | 1927-05-10 | Kalle & Co Ag | Sensitive layer on alpha suitable base and process of making same |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2529029A (en) * | 1946-04-24 | 1950-11-07 | Francolor Sa | Diazotypes containing diazosulfonates |
| US2792303A (en) * | 1951-09-19 | 1957-05-14 | Grinten Chem L V D | Process for the production of diazotype copies |
| US3113865A (en) * | 1960-05-05 | 1963-12-10 | Eastman Kodak Co | Heat developable diazo sulfones |
| US3338711A (en) * | 1962-11-15 | 1967-08-29 | Du Pont | Process for forming azo dye photographic images |
| US3340059A (en) * | 1963-02-27 | 1967-09-05 | Du Pont | Diffusion transfer process for producing silver-free azo dye images |
Also Published As
| Publication number | Publication date |
|---|---|
| NL66139C (en(2012)) | |
| DE815301C (de) | 1951-10-01 |
| FR988484A (fr) | 1951-08-28 |
| NL141017B (nl) | |
| GB649604A (en) | 1951-01-31 |
| CH279648A (fr) | 1951-12-15 |
| BE483794A (en(2012)) |
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