CH624108A5 - - Google Patents

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Info

Publication number: CH624108A5
Authority: CH; Switzerland
Prior art keywords: formula; alkyl; hydrogen; compounds; alkoxy
Prior art date: 1975-10-28

Application number

CH1393875A

Other languages

German (de)

English (en)

Inventor

Salvatore Dr Valenti

Original Assignee

Sandoz Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-10-28

Filing date

1975-10-28

Publication date

1981-07-15

1975-10-28 Application filed by Sandoz Ag filed Critical Sandoz Ag

1975-10-28 Priority to CH1393875A priority Critical patent/CH624108A5/de

1976-10-19 Priority to DE19762647179 priority patent/DE2647179A1/de

1976-10-22 Priority to NL7611722A priority patent/NL7611722A/xx

1976-10-22 Priority to IT51852/76A priority patent/IT1076499B/it

1976-10-26 Priority to GB44387/76A priority patent/GB1550440A/en

1976-10-26 Priority to ES452734A priority patent/ES452734A1/es

1976-10-26 Priority to US05/735,797 priority patent/US4104468A/en

1976-10-27 Priority to JP51128432A priority patent/JPS5253933A/ja

1976-10-27 Priority to BR7607203A priority patent/BR7607203A/pt

1976-10-27 Priority to BE171849A priority patent/BE847701A/xx

1976-10-28 Priority to FR7632522A priority patent/FR2329661A1/fr

1981-07-15 Publication of CH624108A5 publication Critical patent/CH624108A5/de

Links

150000001875 compounds Chemical class 0.000 claims description 105
125000001424 substituent group Chemical group 0.000 claims description 53
229910052739 hydrogen Inorganic materials 0.000 claims description 49
239000001257 hydrogen Substances 0.000 claims description 49
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
230000003287 optical effect Effects 0.000 claims description 30
150000002431 hydrogen Chemical class 0.000 claims description 24
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
238000000034 method Methods 0.000 claims description 23
-1 phenoxyphenyl Chemical group 0.000 claims description 23
229910052736 halogen Inorganic materials 0.000 claims description 17
150000002367 halogens Chemical class 0.000 claims description 17
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 16
125000004093 cyano group Chemical group *C#N 0.000 claims description 15
239000000460 chlorine Substances 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
238000005282 brightening Methods 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 10
239000000758 substrate Substances 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
125000003172 aldehyde group Chemical group 0.000 claims description 5
230000015572 biosynthetic process Effects 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
125000005493 quinolyl group Chemical group 0.000 claims description 4
239000004753 textile Substances 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical group C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 3
125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 3
BQIKRTGTPBOIMK-UHFFFAOYSA-N [O]C[O] Chemical compound [O]C[O] BQIKRTGTPBOIMK-UHFFFAOYSA-N 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000000129 anionic group Chemical group 0.000 claims description 3
150000001768 cations Chemical class 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000005605 benzo group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
125000001715 oxadiazolyl group Chemical group 0.000 claims 1
229920003023 plastic Polymers 0.000 claims 1
239000004033 plastic Substances 0.000 claims 1
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
238000003756 stirring Methods 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
239000000203 mixture Substances 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
229920000728 polyester Polymers 0.000 description 9
239000002244 precipitate Substances 0.000 description 8
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 7
239000005457 ice water Substances 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
239000011734 sodium Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
239000004952 Polyamide Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
229920002647 polyamide Polymers 0.000 description 5
239000000047 product Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
239000000835 fiber Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 4
NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 3
VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
239000008187 granular material Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
238000010992 reflux Methods 0.000 description 3
WTXXUAHMTVAQHW-UHFFFAOYSA-N 3-bromo-4-methylbenzaldehyde Chemical compound CC1=CC=C(C=O)C=C1Br WTXXUAHMTVAQHW-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000004743 Polypropylene Substances 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000004140 cleaning Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
BHYVHYPBRYOMGC-UHFFFAOYSA-N ethyl 4-formylbenzoate Chemical compound CCOC(=O)C1=CC=C(C=O)C=C1 BHYVHYPBRYOMGC-UHFFFAOYSA-N 0.000 description 2
239000004744 fabric Substances 0.000 description 2
239000002657 fibrous material Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000004312 hexamethylene tetramine Substances 0.000 description 2
235000010299 hexamethylene tetramine Nutrition 0.000 description 2
150000002430 hydrocarbons Chemical group 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
229920000098 polyolefin Polymers 0.000 description 2
229920001155 polypropylene Polymers 0.000 description 2
229920002635 polyurethane Polymers 0.000 description 2
239000004814 polyurethane Substances 0.000 description 2
229920000915 polyvinyl chloride Polymers 0.000 description 2
239000004800 polyvinyl chloride Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000004627 regenerated cellulose Substances 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
238000006277 sulfonation reaction Methods 0.000 description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
239000008096 xylene Substances 0.000 description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
QGXNHCXKWFNKCG-UHFFFAOYSA-N 2-(bromomethyl)benzonitrile Chemical compound BrCC1=CC=CC=C1C#N QGXNHCXKWFNKCG-UHFFFAOYSA-N 0.000 description 1
FGPWYCKELFZGGE-UHFFFAOYSA-N 2-cyanato-2-oxoacetic acid Chemical compound OC(=O)C(=O)OC#N FGPWYCKELFZGGE-UHFFFAOYSA-N 0.000 description 1
DYNFCHNNOHNJFG-UHFFFAOYSA-N 2-formylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=O DYNFCHNNOHNJFG-UHFFFAOYSA-N 0.000 description 1
LCRCBXLHWTVPEQ-UHFFFAOYSA-N 2-phenylbenzaldehyde Chemical compound O=CC1=CC=CC=C1C1=CC=CC=C1 LCRCBXLHWTVPEQ-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 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
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
238000004061 bleaching Methods 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
239000000969 carrier Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
239000003599 detergent Substances 0.000 description 1
AIPRAPZUGUTQKX-UHFFFAOYSA-N diethoxyphosphorylmethylbenzene Chemical compound CCOP(=O)(OCC)CC1=CC=CC=C1 AIPRAPZUGUTQKX-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
150000002148 esters Chemical group 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
238000001746 injection moulding Methods 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229940071125 manganese acetate Drugs 0.000 description 1
UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
239000000178 monomer Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
239000004745 nonwoven fabric Substances 0.000 description 1
229940078552 o-xylene Drugs 0.000 description 1
150000002903 organophosphorus compounds Chemical class 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
230000003014 reinforcing effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000007017 scission Effects 0.000 description 1
230000035939 shock Effects 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000009987 spinning Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003459 sulfonic acid esters Chemical class 0.000 description 1
238000004381 surface treatment Methods 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
- C07F9/653—Five-membered rings
- C07F9/65306—Five-membered rings containing two nitrogen atoms
- C07F9/65312—Five-membered rings containing two nitrogen atoms having the two nitrogen atoms in positions 1 and 2
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
- D06L4/60—Optical bleaching or brightening
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/918—Cellulose textile
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/924—Polyamide fiber
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/926—Polyurethane fiber
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/928—Polyolefin fiber

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Detergent Compositions (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CH1393875A 1975-10-28 1975-10-28 CH624108A5 (ja)

Priority Applications (11)

Application Number	Priority Date	Filing Date	Title
CH1393875A CH624108A5 (ja)	1975-10-28	1975-10-28
DE19762647179 DE2647179A1 (de)	1975-10-28	1976-10-19	Organische verbindungen, deren herstellung und verwendung
NL7611722A NL7611722A (nl)	1975-10-28	1976-10-22	Werkwijze voor de bereiding van nieuwe stilbeen- derivaten.
IT51852/76A IT1076499B (it)	1975-10-28	1976-10-22	Derivati del 4 vinil stilbene loro preparazione e loro impiego quali candeggianti ottici
GB44387/76A GB1550440A (en)	1975-10-28	1976-10-26	1,3,4-oxadiazole derivatives
ES452734A ES452734A1 (es)	1975-10-28	1976-10-26	Un procedimiento para la preparacion de nuevos derivados de estilbeno.
US05/735,797 US4104468A (en)	1975-10-28	1976-10-26	1,3,4-Oxadiazolyl-(2)-vinyl stilbene optical brighteners
JP51128432A JPS5253933A (en)	1975-10-28	1976-10-27	New oxadiazol compounds* process for manufacture thereof and optical whitening agent
BR7607203A BR7607203A (pt)	1975-10-28	1976-10-27	Processo para a obtencao de compostos e processo para o aclaramento otico de substratos texteis ou nao-texteis
BE171849A BE847701A (fr)	1975-10-28	1976-10-27	Nouveaux derives du 4-vinyl-stilbene utilisables comme azurants optiques et leur preparation,
FR7632522A FR2329661A1 (fr)	1975-10-28	1976-10-28	Nouveaux derives du 4-vinyl-stilbene utilisables comme azurants optiques et leur preparation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1393875A CH624108A5 (ja)	1975-10-28	1975-10-28

Publications (1)

Publication Number	Publication Date
CH624108A5 true CH624108A5 (ja)	1981-07-15

Family

ID=4396633

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1393875A CH624108A5 (ja)	1975-10-28	1975-10-28

Country Status (11)

Country	Link
US (1)	US4104468A (ja)
JP (1)	JPS5253933A (ja)
BE (1)	BE847701A (ja)
BR (1)	BR7607203A (ja)
CH (1)	CH624108A5 (ja)
DE (1)	DE2647179A1 (ja)
ES (1)	ES452734A1 (ja)
FR (1)	FR2329661A1 (ja)
GB (1)	GB1550440A (ja)
IT (1)	IT1076499B (ja)
NL (1)	NL7611722A (ja)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3070041D1 (en) *	1979-12-13	1985-03-07	Ciba Geigy Ag	Optical brighteners from bistyryl benzene, process for their preparation and their use
US4666627A (en) *	1983-05-08	1987-05-19	Ciba-Geigy Corporation	4-Heterocyclylvinyl-4-'styryl-biphenyls
JPS60177340A (ja) *	1984-02-24	1985-09-11	Fuji Photo Film Co Ltd	感光性組成物
US5118781A (en) *	1991-01-22	1992-06-02	Administrator Of The National Aeronautics And Space Administration	Poly(1,3,4-oxadiozoles) via aromatic nucleophilic displacement
US5707904A (en) *	1996-01-31	1998-01-13	Highland Industries, Inc.	Fabric for backlit signs and awnings
US5895705A (en) *	1997-07-11	1999-04-20	Highland Industries, Inc.	Awning and backlit sign fabric having a selectively eradicable ink layer and a process for producing same
CN109096220B (zh) *	2018-09-12	2020-08-28	信阳师范学院	2-羰基-5-芳基-1,3,4-噁二唑位阻型发光材料及其制备方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH506583A (de) *	1966-04-04	1971-04-30	Ciba Geigy Ag	Verwendung von Stilbenyl-1,3,4-oxdiazol-Derivaten als optische Aufhellmittel ausserhab der Textilindustrie
FR2203819B1 (ja) *	1972-10-18	1978-09-15	Ciba Geigy Ag

1975
- 1975-10-28 CH CH1393875A patent/CH624108A5/de not_active IP Right Cessation
1976
- 1976-10-19 DE DE19762647179 patent/DE2647179A1/de not_active Withdrawn
- 1976-10-22 IT IT51852/76A patent/IT1076499B/it active
- 1976-10-22 NL NL7611722A patent/NL7611722A/xx not_active Application Discontinuation
- 1976-10-26 US US05/735,797 patent/US4104468A/en not_active Expired - Lifetime
- 1976-10-26 ES ES452734A patent/ES452734A1/es not_active Expired
- 1976-10-26 GB GB44387/76A patent/GB1550440A/en not_active Expired
- 1976-10-27 BE BE171849A patent/BE847701A/xx unknown
- 1976-10-27 BR BR7607203A patent/BR7607203A/pt unknown
- 1976-10-27 JP JP51128432A patent/JPS5253933A/ja active Pending
- 1976-10-28 FR FR7632522A patent/FR2329661A1/fr active Granted

Also Published As

Publication number	Publication date
DE2647179A1 (de)	1977-05-12
NL7611722A (nl)	1977-05-02
ES452734A1 (es)	1978-01-01
IT1076499B (it)	1985-04-27
BR7607203A (pt)	1977-09-13
JPS5253933A (en)	1977-04-30
BE847701A (fr)	1977-04-27
US4104468A (en)	1978-08-01
FR2329661B1 (ja)	1982-05-14
FR2329661A1 (fr)	1977-05-27
GB1550440A (en)	1979-08-15

Legal Events

Date	Code	Title	Description
1982-06-30	PL	Patent ceased

Publication	Publication Date	Title
DE1793482C3 (de)	1975-09-25	Neue Bis-stilbenverbindungen und Verfahren zu deren Herstellung
DE2262633A1 (de)	1973-07-05	Neue sulfogruppenhaltige 4,4'divinyldiphenyl-verbindungen
EP0003784B1 (de)	1981-01-28	Distyryl-Verbindungen, sowie deren Herstellung und Verwendung als Weisstöner und Laserfarbstoff
CH508692A (de)	1971-06-15	Verwendung von Styryl-naphthalin-Derivaten als optische Aufhellmittel ausserhalb der Textilindustrie
EP0136259B1 (de)	1988-06-15	4-Heterocyclylvinyl-4'-styryl-biphenyle
CH624108A5 (ja)	1981-07-15
DE2262340A1 (de)	1973-06-28	Stilbenverbindungen
EP0020298B1 (de)	1983-06-22	Benzoxazolyl-Stilbene, Verfahren zu ihrer Herstellung und ihre Verwendung zum optischen Aufhellen von organischen Materialien
DE2212480C2 (de)	1984-03-29	Neue Triazolyl-äthenylphenylenverbindungen, deren Herstellung und Verwendung als optische Aufheller
DE2028037A1 (ja)	1970-12-23
CH636352A5 (de)	1983-05-31	Benzoxazolyl-phenyl-stilbene.
DE1794386C3 (de)	1975-06-19	Verwendung von Bis-stilben-Verbindungen als optische Aufhellmittel
DE2525683A1 (de)	1976-01-02	Sulfogruppenhaltige heterocyclen
DE1594835A1 (de)	1971-01-28	Neue Tolanderivate und deren Verwendung als optische Aufhellmittel
DE1644360A1 (de)	1971-03-25	Sulfonsaeuregruppenfreie basische Farbstoffe und ihre Herstellung
DE2332089A1 (de)	1974-01-03	Neue distyryl-verbindungen, verfahren zu deren herstellung und deren verwendung
DE2609421A1 (de)	1976-09-16	Neue benzoxazol-styryle
DE2029157C3 (de)	1979-08-30	Verfahren zur Herstellung von halogenhaltigen v-Triazolverbindungen
CH560736A5 (en)	1975-04-15	Stilbene optical brighteners - for natural, synthetic and semi-synthetic textiles and as scintillators in photography
DE3126464A1 (de)	1983-01-20	"bis-oxdiazolyl-naphthaline, verfahren zu deren herstellung und deren verwendung"
DE3003540A1 (de)	1981-08-06	Benzoxazolylstilbene, verfahren zu deren herstellung und deren verwendung als optische aufheller
DE1955065A1 (de)	1971-05-19	Styrylverbindungen
DE2839595A1 (de)	1979-03-29	Benzodifurane
DE2029122A1 (ja)	1970-12-23
DE2405063A1 (de)	1974-08-15	Neue benzofuran-derivate, verfahren zu deren herstellung und ihre verwendung als optische aufheller