NO118138B - - Google Patents
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- Publication number
- NO118138B NO118138B NO165387A NO16538766A NO118138B NO 118138 B NO118138 B NO 118138B NO 165387 A NO165387 A NO 165387A NO 16538766 A NO16538766 A NO 16538766A NO 118138 B NO118138 B NO 118138B
- Authority
- NO
- Norway
- Prior art keywords
- parts
- amino
- sulfonic acid
- stilbene
- acid
- Prior art date
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- -1 4-amino-stilbene compound Chemical class 0.000 claims description 46
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 29
- 238000009994 optical bleaching Methods 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000000835 fiber Substances 0.000 claims description 17
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 10
- 239000005977 Ethylene Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004442 acylamino group Chemical group 0.000 claims description 7
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 7
- 229920002678 cellulose Polymers 0.000 claims description 3
- 239000001913 cellulose Substances 0.000 claims description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 239000012467 final product Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical group NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 229920001184 polypeptide Polymers 0.000 claims 1
- 102000004196 processed proteins & peptides Human genes 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 84
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 78
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 60
- 239000000843 powder Substances 0.000 description 55
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 48
- 239000000975 dye Substances 0.000 description 39
- 239000007864 aqueous solution Substances 0.000 description 37
- 239000000047 product Substances 0.000 description 37
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 33
- 239000000243 solution Substances 0.000 description 32
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 30
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 26
- 239000002253 acid Substances 0.000 description 26
- 235000011121 sodium hydroxide Nutrition 0.000 description 26
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 25
- 159000000000 sodium salts Chemical class 0.000 description 25
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 24
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 239000004952 Polyamide Substances 0.000 description 21
- 229920002647 polyamide Polymers 0.000 description 21
- 235000002639 sodium chloride Nutrition 0.000 description 21
- 238000005859 coupling reaction Methods 0.000 description 20
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 20
- SEMRCUIXRUXGJX-UHFFFAOYSA-N 6-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(N)=CC=C21 SEMRCUIXRUXGJX-UHFFFAOYSA-N 0.000 description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 19
- 239000004677 Nylon Substances 0.000 description 19
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 19
- 239000000460 chlorine Substances 0.000 description 19
- 229910052801 chlorine Inorganic materials 0.000 description 19
- 230000008878 coupling Effects 0.000 description 19
- 238000010168 coupling process Methods 0.000 description 19
- 229920001778 nylon Polymers 0.000 description 19
- 239000001632 sodium acetate Substances 0.000 description 19
- 235000017281 sodium acetate Nutrition 0.000 description 19
- 150000008049 diazo compounds Chemical class 0.000 description 18
- 230000003647 oxidation Effects 0.000 description 17
- 238000007254 oxidation reaction Methods 0.000 description 17
- 239000011780 sodium chloride Substances 0.000 description 15
- 229910001018 Cast iron Inorganic materials 0.000 description 14
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 14
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical class C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 13
- 229920003043 Cellulose fiber Polymers 0.000 description 13
- 229910021529 ammonia Inorganic materials 0.000 description 13
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 description 13
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 235000010288 sodium nitrite Nutrition 0.000 description 12
- 239000007844 bleaching agent Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 10
- 229910052500 inorganic mineral Inorganic materials 0.000 description 10
- 235000010755 mineral Nutrition 0.000 description 10
- 239000011707 mineral Substances 0.000 description 10
- 230000003287 optical effect Effects 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- VFPLSXYJYAKZCT-VOTSOKGWSA-N 4-[(e)-2-phenylethenyl]aniline Chemical class C1=CC(N)=CC=C1\C=C\C1=CC=CC=C1 VFPLSXYJYAKZCT-VOTSOKGWSA-N 0.000 description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- QGSPHUSCHLYIBI-UHFFFAOYSA-N 2-[2-(2-phenylethenyl)phenyl]benzo[e]benzotriazole Chemical class C=1C=CC=C(N2N=C3C4=CC=CC=C4C=CC3=N2)C=1C=CC1=CC=CC=C1 QGSPHUSCHLYIBI-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000987 azo dye Substances 0.000 description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
- 239000000344 soap Substances 0.000 description 7
- 239000004552 water soluble powder Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 150000001879 copper Chemical class 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- OSAYFHNJZWWIJI-UHFFFAOYSA-N 2-[2-(4-aminophenyl)ethenyl]-N,N-dimethylbenzenesulfonamide Chemical compound CN(S(=O)(=O)C=1C(C=CC2=CC=C(C=C2)N)=CC=CC1)C OSAYFHNJZWWIJI-UHFFFAOYSA-N 0.000 description 5
- KZCSUEYBKAPKNH-UHFFFAOYSA-N 6-aminonaphthalene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KZCSUEYBKAPKNH-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 239000003610 charcoal Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 5
- 239000000271 synthetic detergent Substances 0.000 description 5
- 239000004753 textile Substances 0.000 description 5
- YBADLXQNJCMBKR-UHFFFAOYSA-N (4-nitrophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C([N+]([O-])=O)C=C1 YBADLXQNJCMBKR-UHFFFAOYSA-N 0.000 description 4
- WMVPJWUGAANMQC-UHFFFAOYSA-N 2-[2-(4-nitrophenyl)ethenyl]benzenesulfonyl chloride Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)C=CC=1C(=CC=CC=1)S(=O)(=O)Cl WMVPJWUGAANMQC-UHFFFAOYSA-N 0.000 description 4
- IROMQOJTKYWOCZ-UHFFFAOYSA-N 3-[2-(4-aminophenyl)ethenyl]-4-chlorobenzenesulfonic acid Chemical compound NC1=CC=C(C=C1)C=CC1=C(C=CC(=C1)S(=O)(=O)O)Cl IROMQOJTKYWOCZ-UHFFFAOYSA-N 0.000 description 4
- FCYPPRMBQLNIQV-UHFFFAOYSA-N 4-[2-(4-aminophenyl)ethenyl]benzenesulfonic acid Chemical compound NC1=CC=C(C=C1)C=CC1=CC=C(C=C1)S(=O)(=O)O FCYPPRMBQLNIQV-UHFFFAOYSA-N 0.000 description 4
- HSZUWLSIVJROCJ-UHFFFAOYSA-N 5-amino-2-(2-phenylethenyl)benzoic acid Chemical compound NC=1C=C(C(=CC1)C=CC1=CC=CC=C1)C(=O)O HSZUWLSIVJROCJ-UHFFFAOYSA-N 0.000 description 4
- YUNBHHWDQDGWHC-UHFFFAOYSA-N 6-aminonaphthalene-1-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=CC(N)=CC=C21 YUNBHHWDQDGWHC-UHFFFAOYSA-N 0.000 description 4
- 229920002292 Nylon 6 Polymers 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000004061 bleaching Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- FPJQJCMWFQFMPA-UHFFFAOYSA-N 2-[2-(4-aminophenyl)ethenyl]benzenesulfonic acid Chemical compound C1=CC(N)=CC=C1C=CC1=CC=CC=C1S(O)(=O)=O FPJQJCMWFQFMPA-UHFFFAOYSA-N 0.000 description 3
- YXOWKXCMKPVKMD-UHFFFAOYSA-N 4-[2-(4-amino-2-chlorophenyl)ethenyl]benzenesulfonic acid Chemical compound NC1=CC(=C(C=C1)C=CC1=CC=C(C=C1)S(=O)(=O)O)Cl YXOWKXCMKPVKMD-UHFFFAOYSA-N 0.000 description 3
- IOGHJPAMRJMQTC-UHFFFAOYSA-N 4-[2-(4-nitrophenyl)ethenyl]benzenesulfonic acid Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)C=CC1=CC=C(C=C1)S(=O)(=O)O IOGHJPAMRJMQTC-UHFFFAOYSA-N 0.000 description 3
- QBHYFEWQILVXEN-UHFFFAOYSA-N 5-amino-2-(2-phenylethenyl)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1C=CC1=CC=CC=C1 QBHYFEWQILVXEN-UHFFFAOYSA-N 0.000 description 3
- IEOIOVRVJPHUGJ-UHFFFAOYSA-N 5-amino-2-(2-phenylethenyl)benzonitrile Chemical compound N#CC1=CC(N)=CC=C1C=CC1=CC=CC=C1 IEOIOVRVJPHUGJ-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 3
- 235000013985 cinnamic acid Nutrition 0.000 description 3
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid group Chemical class C(C=CC1=CC=CC=C1)(=O)O WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical class Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 230000002087 whitening effect Effects 0.000 description 3
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
- AKYFRWPFHWROID-UHFFFAOYSA-N 2-[2-(4-nitrophenyl)ethenyl]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C=CC1=CC=C([N+]([O-])=O)C=C1 AKYFRWPFHWROID-UHFFFAOYSA-N 0.000 description 2
- NVAKPSFOMXLRAX-UHFFFAOYSA-N 3-chloro-4-(2-phenylethenyl)aniline Chemical compound ClC1=C(C=CC(=C1)N)C=CC1=CC=CC=C1 NVAKPSFOMXLRAX-UHFFFAOYSA-N 0.000 description 2
- FSTLXFIQXDXFSM-UHFFFAOYSA-N 3-methoxy-4-(2-phenylethenyl)aniline Chemical compound COC1=CC(N)=CC=C1C=CC1=CC=CC=C1 FSTLXFIQXDXFSM-UHFFFAOYSA-N 0.000 description 2
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical class NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 2
- NLEIGZYWILFSTL-UHFFFAOYSA-N 5-amino-N,N-dimethyl-2-(2-phenylethenyl)benzenesulfonamide Chemical compound CN(S(=O)(=O)C=1C(=CC=C(C1)N)C=CC1=CC=CC=C1)C NLEIGZYWILFSTL-UHFFFAOYSA-N 0.000 description 2
- BHOZTFDONSBGCM-UHFFFAOYSA-N 5-nitro-2-(2-phenylethenyl)benzenesulfonyl chloride Chemical compound [N+](=O)([O-])C1=CC(=C(C=C1)C=CC1=CC=CC=C1)S(=O)(=O)Cl BHOZTFDONSBGCM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229930016911 cinnamic acid Natural products 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- SXBGIRMBSWDFOI-UHFFFAOYSA-N phenyl 2-[2-(4-aminophenyl)ethenyl]benzenesulfonate Chemical compound C1(=CC=CC=C1)OS(=O)(=O)C=1C(C=CC2=CC=C(C=C2)N)=CC=CC1 SXBGIRMBSWDFOI-UHFFFAOYSA-N 0.000 description 2
- AFLIWCIFQBCMJS-UHFFFAOYSA-N phenyl 2-[2-(4-nitrophenyl)ethenyl]benzenesulfonate Chemical compound C1(=CC=CC=C1)OS(=O)(=O)C=1C(C=CC2=CC=C(C=C2)[N+](=O)[O-])=CC=CC1 AFLIWCIFQBCMJS-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003852 triazoles Chemical group 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- BTNQTHYUMJQUJG-ZZXKWVIFSA-N (e)-3-(4-sulfophenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=C(S(O)(=O)=O)C=C1 BTNQTHYUMJQUJG-ZZXKWVIFSA-N 0.000 description 1
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical group C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- BIEFDNUEROKZRA-UHFFFAOYSA-N 2-(2-phenylethenyl)aniline Chemical class NC1=CC=CC=C1C=CC1=CC=CC=C1 BIEFDNUEROKZRA-UHFFFAOYSA-N 0.000 description 1
- BRVWNIITDBKNRV-UHFFFAOYSA-N 2-[2-(2-phenylethenyl)phenyl]triazole Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1N1N=CC=N1 BRVWNIITDBKNRV-UHFFFAOYSA-N 0.000 description 1
- WEUCTQXHZKQIHH-UHFFFAOYSA-N 2-[2-(4-nitrophenyl)ethenyl]benzenesulfinic acid Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)C=CC=1C(=CC=CC1)S(=O)O WEUCTQXHZKQIHH-UHFFFAOYSA-N 0.000 description 1
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SHHKMWMIKILKQW-UHFFFAOYSA-N 2-formylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C=O SHHKMWMIKILKQW-UHFFFAOYSA-N 0.000 description 1
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 1
- WPGVQDHXOUAJBW-UHFFFAOYSA-N 2-methyl-5-nitrobenzenesulfonyl chloride Chemical compound CC1=CC=C([N+]([O-])=O)C=C1S(Cl)(=O)=O WPGVQDHXOUAJBW-UHFFFAOYSA-N 0.000 description 1
- YTZPUTADNGREHA-UHFFFAOYSA-N 2h-benzo[e]benzotriazole Chemical compound C1=CC2=CC=CC=C2C2=NNN=C21 YTZPUTADNGREHA-UHFFFAOYSA-N 0.000 description 1
- XDCSBQHFAMMEIO-UHFFFAOYSA-N 4-chloro-3-[2-(4-nitrophenyl)ethenyl]benzenesulfonic acid Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)C=CC1=C(C=CC(=C1)S(=O)(=O)O)Cl XDCSBQHFAMMEIO-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- XSAOGXMGZVFIIE-UHFFFAOYSA-N 4-formylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=O)C=C1 XSAOGXMGZVFIIE-UHFFFAOYSA-N 0.000 description 1
- PSVPUHBSBYJSMQ-UHFFFAOYSA-N 4-methylsulfonylbenzaldehyde Chemical compound CS(=O)(=O)C1=CC=C(C=O)C=C1 PSVPUHBSBYJSMQ-UHFFFAOYSA-N 0.000 description 1
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical class CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- IEOIOVRVJPHUGJ-VOTSOKGWSA-N 5-amino-2-[(e)-2-phenylethenyl]benzonitrile Chemical compound N#CC1=CC(N)=CC=C1\C=C\C1=CC=CC=C1 IEOIOVRVJPHUGJ-VOTSOKGWSA-N 0.000 description 1
- VQJYELGEYVQDOT-UHFFFAOYSA-N 5-amino-3-chloro-2-(2-phenylethenyl)benzenesulfonic acid Chemical compound ClC=1C=C(C=C(C=1C=CC1=CC=CC=C1)S(=O)(=O)O)N VQJYELGEYVQDOT-UHFFFAOYSA-N 0.000 description 1
- MHAWBMPPBIFKGG-UHFFFAOYSA-N 5-amino-3-methyl-2-(2-phenylethenyl)benzenesulfonic acid Chemical compound CC=1C=C(C=C(C=1C=CC1=CC=CC=C1)S(=O)(=O)O)N MHAWBMPPBIFKGG-UHFFFAOYSA-N 0.000 description 1
- SXKMNMYVCZYMBF-UHFFFAOYSA-N 5-nitro-2-(2-phenylethenyl)benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1C=CC1=CC=CC=C1 SXKMNMYVCZYMBF-UHFFFAOYSA-N 0.000 description 1
- FJMVKIWLOOMXEB-UHFFFAOYSA-N 5-nitro-2-(2-phenylethenyl)benzonitrile Chemical compound N#CC1=CC([N+](=O)[O-])=CC=C1C=CC1=CC=CC=C1 FJMVKIWLOOMXEB-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 241000974482 Aricia saepiolus Species 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- QXEVKTTXLVYPHY-UHFFFAOYSA-N C1(C(N1)=O)=O.NC=1C=C(C(=CC1)C=CC1=CC=CC=C1)S(=O)(=O)O Chemical compound C1(C(N1)=O)=O.NC=1C=C(C(=CC1)C=CC1=CC=CC=C1)S(=O)(=O)O QXEVKTTXLVYPHY-UHFFFAOYSA-N 0.000 description 1
- OTIJGSKBCSBCRD-UHFFFAOYSA-M C[S+]=N.NC1=CC=C(C=CC2=CC=CC=C2)C(S([O-])(=O)=O)=C1 Chemical compound C[S+]=N.NC1=CC=C(C=CC2=CC=CC=C2)C(S([O-])(=O)=O)=C1 OTIJGSKBCSBCRD-UHFFFAOYSA-M 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 238000000297 Sandmeyer reaction Methods 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 241001122767 Theaceae Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- HMFWKZUMVXYKBD-UHFFFAOYSA-N [O-][N+](C1=CC(Cl)=C(C=CC(C=C2)=CC=C2S(O)(=O)=O)C=C1)=O Chemical compound [O-][N+](C1=CC(Cl)=C(C=CC(C=C2)=CC=C2S(O)(=O)=O)C=C1)=O HMFWKZUMVXYKBD-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000005362 aryl sulfone group Chemical group 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- JESCPVSKEGXYSC-UHFFFAOYSA-N chlorobenzene;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.ClC1=CC=CC=C1 JESCPVSKEGXYSC-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229910000361 cobalt sulfate Inorganic materials 0.000 description 1
- 229940044175 cobalt sulfate Drugs 0.000 description 1
- KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 1
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- YIQJZVRKGSRPLF-UHFFFAOYSA-N phenyl 5-nitro-2-(2-phenylethenyl)benzenesulfonate Chemical compound C=1C=CC=CC=1OS(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1C=CC1=CC=CC=C1 YIQJZVRKGSRPLF-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 150000003015 phosphoric acid halides Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920006306 polyurethane fiber Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical group NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000002130 sulfonic acid ester group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
Classifications
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16D—COUPLINGS FOR TRANSMITTING ROTATION; CLUTCHES; BRAKES
- F16D1/00—Couplings for rigidly connecting two coaxial shafts or other movable machine elements
- F16D1/06—Couplings for rigidly connecting two coaxial shafts or other movable machine elements for attachment of a member on a shaft or on a shaft-end
- F16D1/08—Couplings for rigidly connecting two coaxial shafts or other movable machine elements for attachment of a member on a shaft or on a shaft-end with clamping hub; with hub and longitudinal key
- F16D1/09—Couplings for rigidly connecting two coaxial shafts or other movable machine elements for attachment of a member on a shaft or on a shaft-end with clamping hub; with hub and longitudinal key with radial clamping due to axial loading of at least one pair of conical surfaces
- F16D1/093—Couplings for rigidly connecting two coaxial shafts or other movable machine elements for attachment of a member on a shaft or on a shaft-end with clamping hub; with hub and longitudinal key with radial clamping due to axial loading of at least one pair of conical surfaces using one or more elastic segmented conical rings forming at least one of the conical surfaces, the rings being expanded or contracted to effect clamping
- F16D1/097—Couplings for rigidly connecting two coaxial shafts or other movable machine elements for attachment of a member on a shaft or on a shaft-end with clamping hub; with hub and longitudinal key with radial clamping due to axial loading of at least one pair of conical surfaces using one or more elastic segmented conical rings forming at least one of the conical surfaces, the rings being expanded or contracted to effect clamping with clamping effected by ring expansion only, e.g. with an expanded ring located between hub and shaft
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
- B23P—METAL-WORKING NOT OTHERWISE PROVIDED FOR; COMBINED OPERATIONS; UNIVERSAL MACHINE TOOLS
- B23P19/00—Machines for simply fitting together or separating metal parts or objects, or metal and non-metal parts, whether or not involving some deformation; Tools or devices therefor so far as not provided for in other classes
- B23P19/04—Machines for simply fitting together or separating metal parts or objects, or metal and non-metal parts, whether or not involving some deformation; Tools or devices therefor so far as not provided for in other classes for assembling or disassembling parts
- B23P19/06—Screw or nut setting or loosening machines
- B23P19/067—Bolt tensioners
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16B—DEVICES FOR FASTENING OR SECURING CONSTRUCTIONAL ELEMENTS OR MACHINE PARTS TOGETHER, e.g. NAILS, BOLTS, CIRCLIPS, CLAMPS, CLIPS OR WEDGES; JOINTS OR JOINTING
- F16B31/00—Screwed connections specially modified in view of tensile load; Break-bolts
- F16B31/04—Screwed connections specially modified in view of tensile load; Break-bolts for maintaining a tensile load
- F16B31/043—Prestressed connections tensioned by means of liquid, grease, rubber, explosive charge, or the like
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16D—COUPLINGS FOR TRANSMITTING ROTATION; CLUTCHES; BRAKES
- F16D1/00—Couplings for rigidly connecting two coaxial shafts or other movable machine elements
- F16D1/06—Couplings for rigidly connecting two coaxial shafts or other movable machine elements for attachment of a member on a shaft or on a shaft-end
- F16D1/08—Couplings for rigidly connecting two coaxial shafts or other movable machine elements for attachment of a member on a shaft or on a shaft-end with clamping hub; with hub and longitudinal key
- F16D1/0805—Couplings for rigidly connecting two coaxial shafts or other movable machine elements for attachment of a member on a shaft or on a shaft-end with clamping hub; with hub and longitudinal key with radial clamping due to deformation of a resilient body or a body of fluid
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16D—COUPLINGS FOR TRANSMITTING ROTATION; CLUTCHES; BRAKES
- F16D1/00—Couplings for rigidly connecting two coaxial shafts or other movable machine elements
- F16D1/06—Couplings for rigidly connecting two coaxial shafts or other movable machine elements for attachment of a member on a shaft or on a shaft-end
- F16D1/08—Couplings for rigidly connecting two coaxial shafts or other movable machine elements for attachment of a member on a shaft or on a shaft-end with clamping hub; with hub and longitudinal key
- F16D1/09—Couplings for rigidly connecting two coaxial shafts or other movable machine elements for attachment of a member on a shaft or on a shaft-end with clamping hub; with hub and longitudinal key with radial clamping due to axial loading of at least one pair of conical surfaces
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16B—DEVICES FOR FASTENING OR SECURING CONSTRUCTIONAL ELEMENTS OR MACHINE PARTS TOGETHER, e.g. NAILS, BOLTS, CIRCLIPS, CLAMPS, CLIPS OR WEDGES; JOINTS OR JOINTING
- F16B2200/00—Constructional details of connections not covered for in other groups of this subclass
- F16B2200/20—Connections with hook-like parts gripping behind a blind side of an element to be connected
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16B—DEVICES FOR FASTENING OR SECURING CONSTRUCTIONAL ELEMENTS OR MACHINE PARTS TOGETHER, e.g. NAILS, BOLTS, CIRCLIPS, CLAMPS, CLIPS OR WEDGES; JOINTS OR JOINTING
- F16B2200/00—Constructional details of connections not covered for in other groups of this subclass
- F16B2200/30—Dovetail-like connections
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T403/00—Joints and connections
- Y10T403/16—Joints and connections with adjunctive protector, broken parts retainer, repair, assembly or disassembly feature
- Y10T403/1633—Utilizing fluid pressure
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T403/00—Joints and connections
- Y10T403/22—Joints and connections with fluid pressure responsive component
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T403/00—Joints and connections
- Y10T403/46—Rod end to transverse side of member
Landscapes
- Engineering & Computer Science (AREA)
- General Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Physics & Mathematics (AREA)
- Fluid Mechanics (AREA)
- Shafts, Cranks, Connecting Bars, And Related Bearings (AREA)
- Hand Tools For Fitting Together And Separating, Or Other Hand Tools (AREA)
- Mounting Of Bearings Or Others (AREA)
- Coloring (AREA)
- Turbine Rotor Nozzle Sealing (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB47257/65A GB1115457A (en) | 1965-11-08 | 1965-11-08 | Improvements in propeller fastening |
| GB119166 | 1966-01-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO118138B true NO118138B (de) | 1969-11-10 |
Family
ID=26236553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO165387A NO118138B (de) | 1965-11-08 | 1966-10-28 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US3358772A (de) |
| JP (1) | JPS545199B1 (de) |
| DE (2) | DE1600033A1 (de) |
| ES (1) | ES333141A2 (de) |
| FR (1) | FR1507540A (de) |
| GB (1) | GB1115457A (de) |
| NL (1) | NL6615728A (de) |
| NO (1) | NO118138B (de) |
| SE (1) | SE344922B (de) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1115457A (en) * | 1965-11-08 | 1968-05-29 | P & O Res & Dev Co | Improvements in propeller fastening |
| US3549275A (en) * | 1968-11-14 | 1970-12-22 | Waukesha Bearings Corp | Ship's propeller securing and jacking means |
| US3746470A (en) * | 1969-02-27 | 1973-07-17 | Pilgrim P & O Valve Ltd | Mounting of propellers on shafts |
| NL6918492A (de) * | 1969-12-10 | 1971-06-14 | ||
| SE332578B (de) * | 1970-04-10 | 1971-02-08 | Karlstad Mekaniska Ab | |
| FR2175135B1 (de) * | 1972-03-08 | 1975-10-31 | Skf Ind Trading & Dev | |
| DE2212374C2 (de) * | 1972-03-15 | 1986-01-23 | C. Hoegger & Cie. AG, Gossau | Spannkopf zum Festspannen der Messersätze auf der Messerwelle einer Fleischzerkleinerungsmaschine |
| DE2220166C2 (de) * | 1972-04-25 | 1982-04-01 | Amsted-Siemag Kette Gmbh, 5240 Betzdorf | Spannmutter |
| US3841193A (en) * | 1972-06-02 | 1974-10-15 | Tokyo Shibaura Electric Co | Fastening device |
| GB1428300A (en) * | 1974-07-24 | 1976-03-17 | Eriksbergs Mek Verk | Propeller hub |
| US4008970A (en) * | 1975-11-13 | 1977-02-22 | Asko, Inc. | Force applying |
| DE2552873C2 (de) * | 1975-11-25 | 1985-04-04 | Albert Schrem Werkzeugfabrik GmbH, 7928 Giengen | Hydraulisches Spannelement |
| JPS5951477B2 (ja) * | 1978-01-31 | 1984-12-14 | 株式会社神戸製鋼所 | 舶用プロペラの取付構造 |
| GB1586703A (en) * | 1978-05-12 | 1981-03-25 | Pilgrim Eng Dev | Propeller fastening |
| US4182215A (en) * | 1978-05-30 | 1980-01-08 | Terra Tek, Inc. | Failsafe hydraulic prestressing nut |
| US4293996A (en) * | 1978-10-27 | 1981-10-13 | Carrier Corporation | Method for securing a wheel to a rotatable shaft |
| US4349291A (en) * | 1978-10-27 | 1982-09-14 | Carrier Corporation | Apparatus for securing a wheel to a rotatable shaft of a turbomachine |
| JPS5861162U (ja) * | 1981-10-21 | 1983-04-25 | 富士精工株式会社 | ナイフホルダ− |
| USRE33490E (en) * | 1984-03-30 | 1990-12-18 | Apparatus to mechanically stress a bolt-type fastener | |
| US4622730A (en) * | 1984-03-30 | 1986-11-18 | Rolf Steinbock | Apparatus to mechanically stress a bolt-type fastener |
| ZA851815B (en) * | 1984-03-30 | 1985-10-30 | Steinbock Rolf Henning | Apparatus to mechanically stress a bolt-type fastener |
| US4681493A (en) * | 1985-05-07 | 1987-07-21 | Hilti Aktiengesellschaft | Means for maintaining axial stress on a dowel assembly |
| US4745998A (en) * | 1986-10-09 | 1988-05-24 | The Falk Corporation | Disengageable friction coupling for releasably joining an element about a shaft |
| DE68918973T2 (de) * | 1988-03-25 | 1995-05-24 | Girardiere Christian | Schnappverbindungsvorrichtung für zwei ineinandergesteckte Teile. |
| US5285722A (en) * | 1992-11-16 | 1994-02-15 | The Minster Machine Company | Press shutheight adjustment using hydraulic tie rod assemblies |
| US5411337A (en) * | 1994-04-26 | 1995-05-02 | Anlock Products And Machine Co. | Axially guided locking ring assembly |
| GB9411384D0 (en) * | 1994-06-07 | 1994-07-27 | Hedley Purvis Ltd | Method of tensioning and de-tensioning a bolt |
| US5975840A (en) * | 1997-10-29 | 1999-11-02 | Envirotech Pumpsystems, Inc. | Pitot tube pump having axial-stabilizing construction |
| US7147380B2 (en) * | 2003-10-09 | 2006-12-12 | The Timken Company | Pressure screw assembly primarily used with an axially guided locking ring to permit controlled axial clearance movement of the chock bearing |
| CA2457968A1 (en) * | 2004-02-19 | 2005-08-19 | Intregra Technologies Limited | Hydraulic nut assembly |
| CN100455829C (zh) * | 2004-02-25 | 2009-01-28 | J·W·巴克内尔 | 液压辅助紧固件 |
| US7234388B2 (en) * | 2004-04-13 | 2007-06-26 | Helmerich & Payne, Inc. | Liner retention system |
| ES2303473B1 (es) * | 2007-01-26 | 2009-05-21 | Guillermo Petri Larrea | Sistema para garantizar los estiramientos de los tornillos en una union embridada y pretensada. |
| NO20093422A1 (no) * | 2009-11-26 | 2011-02-07 | Bolt Norge As | Anordning ved aksel-boringforbindelse |
| DE102010035057A1 (de) * | 2010-08-21 | 2012-02-23 | Schaeffler Technologies Gmbh & Co. Kg | Verstelleinrichtung für ein Wälzlager sowie Lagersystem mit dieser Verstelleinrichtung |
| DE102010040784A1 (de) * | 2010-09-15 | 2012-03-15 | Aktiebolaget Skf | Spannvorrichtung |
| US10400803B2 (en) | 2014-03-11 | 2019-09-03 | Corebon Ab | Friction connecting means |
| EP3454990B1 (de) * | 2016-05-10 | 2020-06-24 | FLSmidth A/S | Verriegelungsbolzenanordnung für eine brechervorrichtung |
| CN109476004A (zh) * | 2016-06-16 | 2019-03-15 | 超级螺栓公司 | 对多顶起螺栓张紧器的改进 |
| CN111386400A (zh) * | 2017-09-27 | 2020-07-07 | 江森自控科技公司 | 无键叶轮系统和方法 |
| EP3728876B1 (de) * | 2017-12-20 | 2023-05-17 | Superbolt, Inc. | Hydraulische mehrkammer-mehrschrauben-spannvorrichtungen |
| US11358243B2 (en) | 2018-04-25 | 2022-06-14 | Riverhawk Company | High torque friction fit low moment hub joint assembly for a shaft |
| FR3101114B1 (fr) * | 2019-09-23 | 2021-08-27 | Safran Aircraft Engines | Ensemble pour une turbomachine |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE629284A (de) * | ||||
| FR726990A (fr) * | 1931-11-27 | 1932-06-10 | Hélice monobloc à moyeu sphérique | |
| US2571265A (en) * | 1945-06-13 | 1951-10-16 | Leufven Axel Gustav Edvard | Hydraulic tensioning nut |
| GB744994A (en) * | 1953-02-13 | 1956-02-15 | English Electric Co Ltd | Improvements relating to annular joints |
| US2959258A (en) * | 1957-06-27 | 1960-11-08 | Hagemann Franz | Device for the rapid attachment and release of roller cages, toothed rollers or machines mounted on sole-plates |
| US3130628A (en) * | 1958-10-06 | 1964-04-28 | Moeller & Neumann Gmbh | Arrangement for elongating a stay bolt means or tension anchor independently of nut means associated therewith |
| GB908360A (en) * | 1960-02-17 | 1962-10-17 | Harry Freeman | Improvements relating to nuts and bolts or screws |
| US3059949A (en) * | 1960-06-29 | 1962-10-23 | Jr Herbert D Strong | Fastening device |
| GB980090A (en) * | 1960-09-29 | 1965-01-13 | P & O Pilgrim Valve Ltd | Improvements in or relating to nuts and bolts |
| US3097003A (en) * | 1962-04-16 | 1963-07-09 | Dominion Eng Works Ltd | Hydraulic tightening device |
| US3154006A (en) * | 1962-10-12 | 1964-10-27 | Danly Mach Specialties Inc | Tensioning system for power press tie rods |
| GB1001627A (en) * | 1963-02-18 | 1965-08-18 | P & O Res & Dev Co | Improvements in and relating to the mounting of propellers in torque or torque andthrust transmitting connection with a tapered shaft |
| FR1388233A (fr) * | 1964-02-18 | 1965-02-05 | P & O Res & Dev Co | Perfectionnements apportés au montage des hélices et autres organes mobiles sur un arbre assurant la transmission d'un couple ou d'un couple et d'une poussée |
| GB1115457A (en) * | 1965-11-08 | 1968-05-29 | P & O Res & Dev Co | Improvements in propeller fastening |
-
1965
- 1965-11-08 GB GB47257/65A patent/GB1115457A/en not_active Expired
-
1966
- 1966-10-28 NO NO165387A patent/NO118138B/no unknown
- 1966-10-28 US US590398A patent/US3358772A/en not_active Expired - Lifetime
- 1966-11-01 SE SE14972/66A patent/SE344922B/xx unknown
- 1966-11-05 DE DE19661600033 patent/DE1600033A1/de active Pending
- 1966-11-07 ES ES0333141A patent/ES333141A2/es not_active Expired
- 1966-11-08 JP JP7308666A patent/JPS545199B1/ja active Pending
- 1966-11-08 NL NL6615728A patent/NL6615728A/xx unknown
- 1966-12-29 US US605812A patent/US3462180A/en not_active Expired - Lifetime
-
1967
- 1967-01-05 FR FR90108A patent/FR1507540A/fr not_active Expired
- 1967-01-09 DE DE19671575230 patent/DE1575230A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS545199B1 (de) | 1979-03-14 |
| DE1575230A1 (de) | 1969-11-27 |
| NL6615728A (de) | 1967-05-09 |
| GB1115457A (en) | 1968-05-29 |
| SE344922B (de) | 1972-05-08 |
| FR1507540A (fr) | 1967-12-29 |
| US3462180A (en) | 1969-08-19 |
| DE1600033A1 (de) | 1971-03-04 |
| ES333141A2 (es) | 1967-10-01 |
| US3358772A (en) | 1967-12-19 |
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