NO133035B - - Google Patents
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- NO133035B NO133035B NO1907/70A NO190770A NO133035B NO 133035 B NO133035 B NO 133035B NO 1907/70 A NO1907/70 A NO 1907/70A NO 190770 A NO190770 A NO 190770A NO 133035 B NO133035 B NO 133035B
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- NO
- Norway
- Prior art keywords
- parts
- weight
- diazo
- acid
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- Prior art date
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 202
- 238000009833 condensation Methods 0.000 claims description 148
- 230000005494 condensation Effects 0.000 claims description 147
- 239000007859 condensation product Substances 0.000 claims description 116
- 239000012954 diazonium Substances 0.000 claims description 108
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 101
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 97
- 239000002253 acid Substances 0.000 claims description 74
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 70
- 150000001875 compounds Chemical class 0.000 claims description 63
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 54
- 238000004519 manufacturing process Methods 0.000 claims description 51
- -1 aromatic diazonium compound Chemical class 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 45
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 239000000463 material Substances 0.000 claims description 36
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 35
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 32
- 150000001989 diazonium salts Chemical class 0.000 claims description 23
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 230000002378 acidificating effect Effects 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 6
- 239000000543 intermediate Substances 0.000 claims description 6
- 150000002989 phenols Chemical class 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000008379 phenol ethers Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 150000004950 naphthalene Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 210
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 184
- 239000000203 mixture Substances 0.000 description 169
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 147
- 150000008049 diazo compounds Chemical group 0.000 description 109
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 107
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 107
- 235000011007 phosphoric acid Nutrition 0.000 description 102
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 88
- 238000003756 stirring Methods 0.000 description 84
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
- 235000002639 sodium chloride Nutrition 0.000 description 74
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 70
- 239000000047 product Substances 0.000 description 70
- 239000010410 layer Substances 0.000 description 66
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 59
- 238000004458 analytical method Methods 0.000 description 59
- 229910052757 nitrogen Inorganic materials 0.000 description 58
- 239000002244 precipitate Substances 0.000 description 56
- 150000003839 salts Chemical class 0.000 description 56
- 238000000576 coating method Methods 0.000 description 52
- 239000011248 coating agent Substances 0.000 description 51
- 229920005989 resin Polymers 0.000 description 49
- 239000011347 resin Substances 0.000 description 49
- 238000007639 printing Methods 0.000 description 48
- 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 47
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 46
- 239000011592 zinc chloride Substances 0.000 description 44
- 235000005074 zinc chloride Nutrition 0.000 description 44
- 239000000758 substrate Substances 0.000 description 38
- 229930040373 Paraformaldehyde Natural products 0.000 description 35
- 229920002866 paraformaldehyde Polymers 0.000 description 35
- 229910019142 PO4 Inorganic materials 0.000 description 33
- 235000021317 phosphate Nutrition 0.000 description 33
- 229910052796 boron Inorganic materials 0.000 description 30
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 30
- 239000010452 phosphate Substances 0.000 description 30
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 29
- 238000007792 addition Methods 0.000 description 25
- 125000001424 substituent group Chemical group 0.000 description 25
- 239000007864 aqueous solution Substances 0.000 description 24
- 230000008901 benefit Effects 0.000 description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 23
- 229910052782 aluminium Inorganic materials 0.000 description 23
- 150000007513 acids Chemical class 0.000 description 22
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 22
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 229960000583 acetic acid Drugs 0.000 description 21
- 229910052751 metal Inorganic materials 0.000 description 21
- 239000002184 metal Substances 0.000 description 21
- 230000002829 reductive effect Effects 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 239000011888 foil Substances 0.000 description 19
- 239000011780 sodium chloride Substances 0.000 description 19
- 229910052717 sulfur Inorganic materials 0.000 description 19
- 239000007795 chemical reaction product Substances 0.000 description 18
- 238000001816 cooling Methods 0.000 description 18
- 238000001035 drying Methods 0.000 description 18
- 239000012362 glacial acetic acid Substances 0.000 description 17
- 239000003960 organic solvent Substances 0.000 description 17
- 238000010438 heat treatment Methods 0.000 description 16
- 229910052698 phosphorus Inorganic materials 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 239000007858 starting material Substances 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 14
- 238000011161 development Methods 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 13
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 12
- 238000001556 precipitation Methods 0.000 description 12
- 229910021653 sulphate ion Inorganic materials 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000975 dye Substances 0.000 description 11
- 238000003860 storage Methods 0.000 description 11
- 229920002301 cellulose acetate Polymers 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 239000000725 suspension Substances 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 239000000084 colloidal system Substances 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 8
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 7
- 206010034972 Photosensitivity reaction Diseases 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 7
- 230000036211 photosensitivity Effects 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 230000009257 reactivity Effects 0.000 description 7
- 239000012266 salt solution Substances 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 description 6
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N N-phenyl aniline Natural products C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
- 239000004372 Polyvinyl alcohol Substances 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 230000001680 brushing effect Effects 0.000 description 6
- 150000001805 chlorine compounds Chemical class 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 230000002349 favourable effect Effects 0.000 description 6
- 230000001976 improved effect Effects 0.000 description 6
- 229910001507 metal halide Inorganic materials 0.000 description 6
- 150000005309 metal halides Chemical class 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
- 229920002451 polyvinyl alcohol Polymers 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 6
- 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 5
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 239000000987 azo dye Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000008199 coating composition Substances 0.000 description 5
- 238000006482 condensation reaction Methods 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000008098 formaldehyde solution Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 5
- 229960005323 phenoxyethanol Drugs 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 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 5
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 229920003176 water-insoluble polymer Polymers 0.000 description 5
- YZVWKHVRBDQPMQ-UHFFFAOYSA-N 1-aminopyrene Chemical compound C1=C2C(N)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 YZVWKHVRBDQPMQ-UHFFFAOYSA-N 0.000 description 4
- KUMMBDBTERQYCG-UHFFFAOYSA-N 2,6-bis(hydroxymethyl)-4-methylphenol Chemical compound CC1=CC(CO)=C(O)C(CO)=C1 KUMMBDBTERQYCG-UHFFFAOYSA-N 0.000 description 4
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 4
- XXYMSQQCBUKFHE-UHFFFAOYSA-N 4-nitro-n-phenylaniline Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC1=CC=CC=C1 XXYMSQQCBUKFHE-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 239000004411 aluminium Substances 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 4
- 229920002689 polyvinyl acetate Polymers 0.000 description 4
- 239000011118 polyvinyl acetate Substances 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 150000003460 sulfonic acids Chemical class 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- 229920003169 water-soluble polymer Polymers 0.000 description 4
- 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 3
- BDWINMYKMOTUNB-UHFFFAOYSA-N 2,5-bis(ethoxymethyl)thiophene Chemical compound CCOCC1=CC=C(COCC)S1 BDWINMYKMOTUNB-UHFFFAOYSA-N 0.000 description 3
- VRMKFAFIVOVETG-UHFFFAOYSA-N 2,6-bis(methoxymethyl)-4-methylphenol Chemical compound COCC1=CC(C)=CC(COC)=C1O VRMKFAFIVOVETG-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- MKASXAGBWHIGCF-UHFFFAOYSA-N 3-methoxy-n-phenylaniline Chemical compound COC1=CC=CC(NC=2C=CC=CC=2)=C1 MKASXAGBWHIGCF-UHFFFAOYSA-N 0.000 description 3
- VPRIGCVCJPKVFZ-UHFFFAOYSA-N 4-chloro-n-phenylaniline Chemical compound C1=CC(Cl)=CC=C1NC1=CC=CC=C1 VPRIGCVCJPKVFZ-UHFFFAOYSA-N 0.000 description 3
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 3
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 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 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
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- OEZDYMAFWLGKFC-UHFFFAOYSA-N n-(2,5-diethoxyphenyl)benzamide Chemical compound CCOC1=CC=C(OCC)C(NC(=O)C=2C=CC=CC=2)=C1 OEZDYMAFWLGKFC-UHFFFAOYSA-N 0.000 description 1
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 description 1
- OHPZPBNDOVQJMH-UHFFFAOYSA-N n-ethyl-4-methylbenzenesulfonamide Chemical compound CCNS(=O)(=O)C1=CC=C(C)C=C1 OHPZPBNDOVQJMH-UHFFFAOYSA-N 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 210000002445 nipple Anatomy 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 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
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- KSSNXJHPEFVKHY-UHFFFAOYSA-N phenol;hydrate Chemical compound O.OC1=CC=CC=C1 KSSNXJHPEFVKHY-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-M phthalate(1-) Chemical compound OC(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-M 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000009711 regulatory function Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000005488 sandblasting Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- QYHFIVBSNOWOCQ-UHFFFAOYSA-N selenic acid Chemical compound O[Se](O)(=O)=O QYHFIVBSNOWOCQ-UHFFFAOYSA-N 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 238000010408 sweeping Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 210000004885 white matter Anatomy 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/016—Diazonium salts or compounds
- G03F7/021—Macromolecular diazonium compounds; Macromolecular additives, e.g. binders
-
- 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
- C08G8/28—Chemically modified polycondensates
-
- 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
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/04—Additive processes using colour screens; Materials therefor; Preparing or processing such materials
- G03C7/06—Manufacture of colour screens
- G03C7/08—Manufacture of colour screens from diversely-coloured grains irregularly distributed
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Manufacturing & Machinery (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Indole Compounds (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Holo Graphy (AREA)
- Photoreceptors In Electrophotography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82629769A | 1969-05-20 | 1969-05-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO133035B true NO133035B (hu) | 1975-11-17 |
| NO133035C NO133035C (hu) | 1976-02-25 |
Family
ID=25246172
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1907/70A NO133035C (hu) | 1969-05-20 | 1970-05-19 | |
| NO2024/73A NO138817C (no) | 1969-05-20 | 1973-05-15 | Lysfoelsomt reproduksjonsmateriale |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2024/73A NO138817C (no) | 1969-05-20 | 1973-05-15 | Lysfoelsomt reproduksjonsmateriale |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS4948001B1 (hu) |
| AT (2) | AT314350B (hu) |
| BE (1) | BE750692A (hu) |
| CA (1) | CA973544A (hu) |
| CH (1) | CH607099A5 (hu) |
| DE (2) | DE2065732C2 (hu) |
| DK (1) | DK143818C (hu) |
| ES (1) | ES379776A1 (hu) |
| FI (1) | FI53897C (hu) |
| FR (1) | FR2048538A5 (hu) |
| GB (1) | GB1312925A (hu) |
| HU (1) | HU167985B (hu) |
| IL (1) | IL34547A (hu) |
| NL (1) | NL168631C (hu) |
| NO (2) | NO133035C (hu) |
| PL (2) | PL94400B1 (hu) |
| SE (2) | SE369417B (hu) |
| SU (2) | SU568395A3 (hu) |
| YU (1) | YU34463B (hu) |
| ZA (1) | ZA703395B (hu) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2822887A1 (de) * | 1978-05-26 | 1979-11-29 | Hoechst Ag | Lichtempfindliches aufzeichnungsmaterial und verfahren zur herstellung von reliefaufzeichnungen |
| US4533620A (en) * | 1982-03-18 | 1985-08-06 | American Hoechst Corporation | Light sensitive co-condensates |
| DE3409888A1 (de) * | 1984-03-17 | 1985-09-19 | Hoechst Ag, 6230 Frankfurt | Lichtempfindliches aufzeichnungsmaterial und dessen verwendung in einem verfahren zum herstellen einer druckform oder einer gedruckten schaltung |
| DE3509383A1 (de) * | 1985-03-15 | 1986-09-18 | Hoechst Ag, 6230 Frankfurt | Lichtempfindliches diazoniumsalz-polykondensationsprodukt und damit hergestelltes lichtempfindliches aufzeichnungsmaterial |
| DE3635303A1 (de) | 1986-10-17 | 1988-04-28 | Hoechst Ag | Verfahren zur abtragenden modifizierung von mehrstufig aufgerauhten traegermaterialien aus aluminium oder dessen legierungen und deren verwendung bei der herstellung von offsetdruckplatten |
| 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 |
| GB9326150D0 (en) * | 1993-12-22 | 1994-02-23 | Alcan Int Ltd | Electrochemical roughening method |
| DE4439184A1 (de) | 1994-11-03 | 1996-05-09 | Hoechst Ag | Lichtempfindliches Aufzeichnungsmaterial |
| US8907362B2 (en) | 2012-01-24 | 2014-12-09 | Cooledge Lighting Inc. | Light-emitting dies incorporating wavelength-conversion materials and related methods |
| US8896010B2 (en) | 2012-01-24 | 2014-11-25 | Cooledge Lighting Inc. | Wafer-level flip chip device packages and related methods |
| WO2013112435A1 (en) | 2012-01-24 | 2013-08-01 | Cooledge Lighting Inc. | Light - emitting devices having discrete phosphor chips and fabrication methods |
| RU2513620C1 (ru) * | 2012-10-01 | 2014-04-20 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Национальный исследовательский Томский государственный университет" (ТГУ) | Композиция для фотоактивированного травления пленок диоксида кремния |
| WO2015119858A1 (en) | 2014-02-05 | 2015-08-13 | Cooledge Lighting Inc. | Light-emitting dies incorporating wavelength-conversion materials and related methods |
| EP3548970A1 (en) | 2016-12-01 | 2019-10-09 | Agfa Nv | Method of making a lithographic printing plate precursor containing a diazonium compound |
| EP3495891B1 (en) | 2017-12-08 | 2021-06-16 | Agfa Nv | A method for making a lithographic printing plate |
| US20220066318A1 (en) | 2018-12-10 | 2022-03-03 | Agfa Nv | Lithographic printing plate precursor |
| CN115141330B (zh) * | 2022-08-17 | 2023-11-03 | 江苏麒祥高新材料有限公司 | 一种新型烷基酚醛硫化树脂及其制备方法和组合物 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2155512A (en) * | 1937-09-09 | 1939-04-25 | Western Cartridge Co | Pump-action firearm |
| NL273557A (hu) * | 1961-01-25 |
-
1970
- 1970-05-08 NL NLAANVRAGE7006715,A patent/NL168631C/xx not_active IP Right Cessation
- 1970-05-15 SE SE06693/70A patent/SE369417B/xx unknown
- 1970-05-15 SU SU7001435202A patent/SU568395A3/ru active
- 1970-05-15 SE SE7305098A patent/SE376492B/xx unknown
- 1970-05-18 YU YU1253/70A patent/YU34463B/xx unknown
- 1970-05-18 IL IL34547A patent/IL34547A/xx unknown
- 1970-05-18 PL PL1970174772A patent/PL94400B1/pl unknown
- 1970-05-18 ES ES379776A patent/ES379776A1/es not_active Expired
- 1970-05-18 PL PL1970140706A patent/PL97540B1/pl unknown
- 1970-05-19 CA CA083,035A patent/CA973544A/en not_active Expired
- 1970-05-19 ZA ZA703395A patent/ZA703395B/xx unknown
- 1970-05-19 DE DE2065732A patent/DE2065732C2/de not_active Expired
- 1970-05-19 FI FI1398/70A patent/FI53897C/fi active
- 1970-05-19 CH CH739070A patent/CH607099A5/xx not_active IP Right Cessation
- 1970-05-19 DK DK253370A patent/DK143818C/da not_active IP Right Cessation
- 1970-05-19 GB GB2421770A patent/GB1312925A/en not_active Expired
- 1970-05-19 AT AT446770A patent/AT314350B/de not_active IP Right Cessation
- 1970-05-19 AT AT00553/71A patent/AT314501B/de not_active IP Right Cessation
- 1970-05-19 HU HUAO314A patent/HU167985B/hu unknown
- 1970-05-19 NO NO1907/70A patent/NO133035C/no unknown
- 1970-05-19 DE DE2024244A patent/DE2024244C2/de not_active Expired
- 1970-05-20 BE BE750692D patent/BE750692A/xx not_active IP Right Cessation
- 1970-05-20 JP JP45042823A patent/JPS4948001B1/ja active Pending
- 1970-05-20 FR FR7018228A patent/FR2048538A5/fr not_active Expired
- 1970-10-06 SU SU1482185A patent/SU522824A3/ru active
-
1973
- 1973-05-15 NO NO2024/73A patent/NO138817C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL97540B1 (pl) | 1978-03-30 |
| NL168631C (nl) | 1982-04-16 |
| DE2065732C2 (de) | 1983-05-19 |
| YU34463B (en) | 1979-07-10 |
| DK143818B (da) | 1981-10-12 |
| SE369417B (hu) | 1974-08-26 |
| DE2024244A1 (de) | 1970-11-26 |
| IL34547A0 (en) | 1970-07-19 |
| AT314501B (de) | 1974-03-15 |
| DE2024244C2 (de) | 1984-09-27 |
| GB1312925A (en) | 1973-04-11 |
| SE376492B (hu) | 1975-05-26 |
| FR2048538A5 (hu) | 1971-03-19 |
| PL94400B1 (pl) | 1977-08-31 |
| ZA703395B (en) | 1971-06-30 |
| AT314350B (de) | 1974-03-25 |
| FI53897C (fi) | 1978-08-10 |
| SU522824A3 (ru) | 1976-07-25 |
| IL34547A (en) | 1983-05-15 |
| DK143818C (da) | 1982-03-15 |
| SU568395A3 (ru) | 1977-08-05 |
| NO138817B (no) | 1978-08-07 |
| DE2065732A1 (de) | 1975-08-21 |
| NL7006715A (hu) | 1970-11-24 |
| HU167985B (hu) | 1976-02-28 |
| NO133035C (hu) | 1976-02-25 |
| CA973544A (en) | 1975-08-26 |
| NL168631B (nl) | 1981-11-16 |
| YU125370A (en) | 1978-12-31 |
| JPS4948001B1 (hu) | 1974-12-19 |
| NO138817C (no) | 1978-11-15 |
| CH607099A5 (hu) | 1978-11-30 |
| FI53897B (fi) | 1978-05-02 |
| BE750692A (fr) | 1970-11-20 |
| ES379776A1 (es) | 1974-08-16 |
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