DE2024242C2 - Verfahren zur Herstellung Diazoniumgruppen enthaltender Kondensationsprodukte - Google Patents
Verfahren zur Herstellung Diazoniumgruppen enthaltender KondensationsprodukteInfo
- Publication number
- DE2024242C2 DE2024242C2 DE2024242A DE2024242A DE2024242C2 DE 2024242 C2 DE2024242 C2 DE 2024242C2 DE 2024242 A DE2024242 A DE 2024242A DE 2024242 A DE2024242 A DE 2024242A DE 2024242 C2 DE2024242 C2 DE 2024242C2
- Authority
- DE
- Germany
- Prior art keywords
- condensation
- diazo
- acid
- bis
- component
- 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
Links
- 239000007859 condensation product Substances 0.000 title claims description 95
- 238000000034 method Methods 0.000 title claims description 40
- 238000002360 preparation method Methods 0.000 title claims description 20
- 230000008569 process Effects 0.000 title claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 title claims description 13
- 238000009833 condensation Methods 0.000 claims description 146
- 230000005494 condensation Effects 0.000 claims description 144
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 140
- -1 heterocyclic aromatic radical Chemical class 0.000 claims description 78
- 235000011007 phosphoric acid Nutrition 0.000 claims description 72
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 66
- 239000012954 diazonium Substances 0.000 claims description 64
- 150000001875 compounds Chemical class 0.000 claims description 60
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000001424 substituent group Chemical group 0.000 claims description 34
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 26
- 230000002378 acidificating effect Effects 0.000 claims description 24
- 150000001989 diazonium salts Chemical class 0.000 claims description 23
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 22
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 20
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 11
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000004202 carbamide Substances 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 8
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical group NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 150000003857 carboxamides Chemical class 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 106
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 89
- 239000000203 mixture Substances 0.000 description 83
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 81
- 239000000243 solution Substances 0.000 description 75
- 150000008049 diazo compounds Chemical group 0.000 description 64
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 60
- 235000002639 sodium chloride Nutrition 0.000 description 54
- 229910052757 nitrogen Inorganic materials 0.000 description 53
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 51
- CZKKIYPWLBINSU-UHFFFAOYSA-N 2-[3-[2-[2-[bis(carboxymethyl)amino]-5-methylphenoxy]ethoxy]-N-(carboxymethyl)-4-(2-diazoacetyl)anilino]acetic acid Chemical compound Cc1ccc(N(CC(O)=O)CC(O)=O)c(OCCOc2cc(ccc2C(=O)C=[N+]=[N-])N(CC(O)=O)CC(O)=O)c1 CZKKIYPWLBINSU-UHFFFAOYSA-N 0.000 description 50
- 229910052797 bismuth Inorganic materials 0.000 description 49
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 44
- 238000003756 stirring Methods 0.000 description 39
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 38
- 239000000047 product Substances 0.000 description 38
- 239000002253 acid Substances 0.000 description 36
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 33
- 238000004458 analytical method Methods 0.000 description 33
- 238000004519 manufacturing process Methods 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
- 229920005989 resin Polymers 0.000 description 32
- 239000011347 resin Substances 0.000 description 32
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 27
- 239000000460 chlorine Substances 0.000 description 24
- 239000002244 precipitate Substances 0.000 description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 22
- 235000005074 zinc chloride Nutrition 0.000 description 22
- 239000011592 zinc chloride Substances 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000003795 chemical substances by application Substances 0.000 description 20
- 229910019142 PO4 Inorganic materials 0.000 description 18
- 235000021317 phosphate Nutrition 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 125000003545 alkoxy group Chemical group 0.000 description 16
- 239000010452 phosphate Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 229960000583 acetic acid Drugs 0.000 description 14
- 239000007795 chemical reaction product Substances 0.000 description 14
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- 150000007513 acids Chemical class 0.000 description 12
- 229910052801 chlorine Inorganic materials 0.000 description 12
- 239000011780 sodium chloride Substances 0.000 description 12
- 229910052717 sulfur Inorganic materials 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- 229910052782 aluminium Inorganic materials 0.000 description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 239000000975 dye Substances 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 239000012362 glacial acetic acid Substances 0.000 description 10
- 150000002989 phenols Chemical class 0.000 description 10
- 229910052698 phosphorus Inorganic materials 0.000 description 10
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 9
- 230000008901 benefit Effects 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
- 238000001556 precipitation Methods 0.000 description 9
- 238000007639 printing Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 239000004305 biphenyl Substances 0.000 description 8
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 150000003460 sulfonic acids Chemical class 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- 229930040373 Paraformaldehyde Natural products 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 6
- 229920002866 paraformaldehyde Polymers 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 229910021653 sulphate ion Inorganic materials 0.000 description 6
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
- 150000008379 phenol ethers Chemical class 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 230000003213 activating effect Effects 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 239000000987 azo dye Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 229920002301 cellulose acetate Polymers 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 230000007812 deficiency Effects 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 4
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 4
- 230000002349 favourable effect Effects 0.000 description 4
- 238000010348 incorporation Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 4
- YDGFWBUHUUSSRS-UHFFFAOYSA-N 1-(methoxymethyl)-4-phenoxybenzene Chemical compound C1=CC(COC)=CC=C1OC1=CC=CC=C1 YDGFWBUHUUSSRS-UHFFFAOYSA-N 0.000 description 3
- LXFQSRIDYRFTJW-UHFFFAOYSA-M 2,4,6-trimethylbenzenesulfonate Chemical compound CC1=CC(C)=C(S([O-])(=O)=O)C(C)=C1 LXFQSRIDYRFTJW-UHFFFAOYSA-M 0.000 description 3
- LXFQSRIDYRFTJW-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonic acid Chemical compound CC1=CC(C)=C(S(O)(=O)=O)C(C)=C1 LXFQSRIDYRFTJW-UHFFFAOYSA-N 0.000 description 3
- BDWINMYKMOTUNB-UHFFFAOYSA-N 2,5-bis(ethoxymethyl)thiophene Chemical compound CCOCC1=CC=C(COCC)S1 BDWINMYKMOTUNB-UHFFFAOYSA-N 0.000 description 3
- BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- VFLRGCHXIWFSGO-UHFFFAOYSA-N [4-[4-(hydroxymethyl)phenoxy]phenyl]methanol Chemical compound C1=CC(CO)=CC=C1OC1=CC=C(CO)C=C1 VFLRGCHXIWFSGO-UHFFFAOYSA-N 0.000 description 3
- KDSNMBNNCZRNPP-UHFFFAOYSA-N [5-(hydroxymethyl)-2,4-dimethylphenyl]methanol Chemical compound CC1=CC(C)=C(CO)C=C1CO KDSNMBNNCZRNPP-UHFFFAOYSA-N 0.000 description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 3
- 229940092714 benzenesulfonic acid Drugs 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 239000000084 colloidal system Substances 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 3
- 229920001568 phenolic resin Polymers 0.000 description 3
- 229920002689 polyvinyl acetate Polymers 0.000 description 3
- 239000011118 polyvinyl acetate Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- XRXLTFYZSLXTHI-UHFFFAOYSA-N 1,5-bis(methoxymethyl)-2,4-di(propan-2-yl)benzene Chemical compound COCC1=CC(COC)=C(C(C)C)C=C1C(C)C XRXLTFYZSLXTHI-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- VRMKFAFIVOVETG-UHFFFAOYSA-N 2,6-bis(methoxymethyl)-4-methylphenol Chemical compound COCC1=CC(C)=CC(COC)=C1O VRMKFAFIVOVETG-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
- PLNNBRYFKARCEV-UHFFFAOYSA-N 2-[(2-hydroxyphenyl)methoxymethyl]phenol Chemical compound OC1=CC=CC=C1COCC1=CC=CC=C1O PLNNBRYFKARCEV-UHFFFAOYSA-N 0.000 description 2
- OFRMTRNULBCTHS-UHFFFAOYSA-N 2-[2-[2-[2-[bis(carboxymethyl)amino]-5-(2-diazoacetyl)phenoxy]ethoxy]-N-(carboxymethyl)-4-(2-diazoacetyl)anilino]acetic acid Chemical compound C(=O)(O)CN(C1=C(OCCOC2=C(C=CC(=C2)C(C=[N+]=[N-])=O)N(CC(=O)O)CC(=O)O)C=C(C=C1)C(C=[N+]=[N-])=O)CC(=O)O OFRMTRNULBCTHS-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-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
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
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- 239000011975 tartaric acid Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08G12/06—Amines
- C08G12/08—Amines aromatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08G12/22—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
- C08G16/02—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/10—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with phenol
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/28—Chemically modified polycondensates
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Furnace Details (AREA)
- Indole Compounds (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82629669A | 1969-05-20 | 1969-05-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2024242A1 DE2024242A1 (de) | 1970-12-17 |
| DE2024242C2 true DE2024242C2 (de) | 1984-09-20 |
Family
ID=25246170
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2024242A Expired DE2024242C2 (de) | 1969-05-20 | 1970-05-19 | Verfahren zur Herstellung Diazoniumgruppen enthaltender Kondensationsprodukte |
| DE2065733A Expired DE2065733C2 (de) | 1969-05-20 | 1970-05-19 | Lichtempfindliches Aufzeichnungsmaterial |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2065733A Expired DE2065733C2 (de) | 1969-05-20 | 1970-05-19 | Lichtempfindliches Aufzeichnungsmaterial |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS4945323B1 (en, 2012) |
| AT (1) | AT327171B (en, 2012) |
| BE (1) | BE750693A (en, 2012) |
| BG (1) | BG20629A3 (en, 2012) |
| CA (1) | CA971160A (en, 2012) |
| CH (1) | CH607098A5 (en, 2012) |
| DE (2) | DE2024242C2 (en, 2012) |
| DK (1) | DK143621C (en, 2012) |
| ES (1) | ES379775A1 (en, 2012) |
| FI (1) | FI53896C (en, 2012) |
| FR (1) | FR2048537A5 (en, 2012) |
| GB (1) | GB1312926A (en, 2012) |
| IL (1) | IL34548A (en, 2012) |
| NL (1) | NL174835C (en, 2012) |
| NO (1) | NO133756C (en, 2012) |
| PL (1) | PL92450B1 (en, 2012) |
| SE (1) | SE386435B (en, 2012) |
| SU (1) | SU660590A3 (en, 2012) |
| YU (1) | YU33996B (en, 2012) |
| ZA (1) | ZA703394B (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2058178C2 (de) * | 1970-11-26 | 1982-04-01 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Siebdruckformen |
| US3915707A (en) * | 1972-11-25 | 1975-10-28 | Hoechst Ag | Diazo resin composition with phosphor pigments and process for the manufacture of a screen for cathode ray tubes |
| JPS5128001A (en) * | 1974-08-29 | 1976-03-09 | Polychrome Corp | Kizaijono kankohifuku oyobi sonoseizoho |
| FR2406230A1 (fr) * | 1977-10-11 | 1979-05-11 | Eastman Kodak Co | Composition photosensible et produi |
| DE2822887A1 (de) * | 1978-05-26 | 1979-11-29 | Hoechst Ag | Lichtempfindliches aufzeichnungsmaterial und verfahren zur herstellung von reliefaufzeichnungen |
| US4436804A (en) | 1981-03-20 | 1984-03-13 | American Hoechst Corporation | Light-sensitive polymeric diazonium condensates and reproduction compositions and materials therewith |
| EP0061150B1 (de) * | 1981-03-20 | 1986-10-15 | American Hoechst Corporation | Lichtempfindliches Polykondensationsprodukt, Verfahren zu seiner Herstellung und dieses enthaltendes lichtempfindliches Aufzeichnungsmaterial |
| US4469772A (en) * | 1982-06-03 | 1984-09-04 | American Hoechst Corporation | Water developable dye coating on substrate with two diazo polycondensation products and water soluble polymeric binder |
| DE3364925D1 (en) * | 1982-06-03 | 1986-09-04 | Hoechst Co American | Photosensitive composition developable with water, and photosensitive copying material produced therefrom |
| JP2944296B2 (ja) | 1992-04-06 | 1999-08-30 | 富士写真フイルム株式会社 | 感光性平版印刷版の製造方法 |
| CN110317130B (zh) * | 2018-03-29 | 2021-12-21 | 深圳翰宇药业股份有限公司 | 化合物及其制备方法和应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE630564A (en, 2012) | 1961-01-25 |
-
1970
- 1970-05-08 NL NLAANVRAGE7006716,A patent/NL174835C/xx not_active IP Right Cessation
- 1970-05-15 SE SE7006692A patent/SE386435B/xx unknown
- 1970-05-15 SU SU701435301A patent/SU660590A3/ru active
- 1970-05-18 PL PL1970140707A patent/PL92450B1/pl unknown
- 1970-05-18 YU YU1254/70A patent/YU33996B/xx unknown
- 1970-05-18 ES ES379775A patent/ES379775A1/es not_active Expired
- 1970-05-18 IL IL34548A patent/IL34548A/xx unknown
- 1970-05-18 BG BG14700A patent/BG20629A3/xx unknown
- 1970-05-19 DE DE2024242A patent/DE2024242C2/de not_active Expired
- 1970-05-19 AT AT763971*7A patent/AT327171B/de not_active IP Right Cessation
- 1970-05-19 CH CH738970A patent/CH607098A5/xx not_active IP Right Cessation
- 1970-05-19 FI FI1393/70A patent/FI53896C/fi active
- 1970-05-19 NO NO1905/70A patent/NO133756C/no unknown
- 1970-05-19 ZA ZA703394A patent/ZA703394B/xx unknown
- 1970-05-19 CA CA083,040A patent/CA971160A/en not_active Expired
- 1970-05-19 DK DK253570A patent/DK143621C/da not_active IP Right Cessation
- 1970-05-19 DE DE2065733A patent/DE2065733C2/de not_active Expired
- 1970-05-19 GB GB2421970A patent/GB1312926A/en not_active Expired
- 1970-05-20 BE BE750693D patent/BE750693A/xx not_active IP Right Cessation
- 1970-05-20 FR FR7018227A patent/FR2048537A5/fr not_active Expired
- 1970-05-20 JP JP45042826A patent/JPS4945323B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| YU33996B (en) | 1978-09-08 |
| ZA703394B (en) | 1971-06-30 |
| IL34548A (en) | 1985-04-30 |
| ATA763971A (de) | 1975-04-15 |
| FI53896B (fi) | 1978-05-02 |
| BG20629A3 (en, 2012) | 1975-12-05 |
| YU125470A (en) | 1978-02-28 |
| JPS4945323B1 (en, 2012) | 1974-12-03 |
| NL174835C (nl) | 1984-08-16 |
| DK143621C (da) | 1982-02-15 |
| FI53896C (fi) | 1978-08-10 |
| NL7006716A (en, 2012) | 1970-11-24 |
| CH607098A5 (en, 2012) | 1978-11-30 |
| IL34548A0 (en) | 1970-07-19 |
| GB1312926A (en) | 1973-04-11 |
| NO133756C (en, 2012) | 1976-06-23 |
| SE386435B (sv) | 1976-08-09 |
| PL92450B1 (en, 2012) | 1977-04-30 |
| ES379775A1 (es) | 1973-02-01 |
| BE750693A (fr) | 1970-11-20 |
| NL174835B (nl) | 1984-03-16 |
| DE2024242A1 (de) | 1970-12-17 |
| CA971160A (en) | 1975-07-15 |
| FR2048537A5 (en, 2012) | 1971-03-19 |
| AT327171B (de) | 1976-01-26 |
| DE2065733C2 (de) | 1982-10-07 |
| DK143621B (da) | 1981-09-14 |
| NO133756B (en, 2012) | 1976-03-15 |
| SU660590A3 (ru) | 1979-04-30 |
| DE2065733A1 (de) | 1975-09-04 |
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