CA1080718A - 2-stilbenyl-1,2,3-triazoles which contain carboxyl groups - Google Patents

2-stilbenyl-1,2,3-triazoles which contain carboxyl groups

Info

Publication number: CA1080718A
Authority: CA; Canada
Prior art keywords: carbon atoms; formula; alkoxy; stilbenyl; triazole
Prior art date: 1974-09-09
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA234,833A

Other languages

English (en)

French (fr)

Other versions

CA234833S (en

Inventor

Hans R. Meyer

Reinhard Zweidler

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Original Assignee

Ciba Geigy 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.)

1974-09-09

Filing date

1975-09-05

Publication date

1980-07-01

1975-09-05 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1980-07-01 Application granted granted Critical

1980-07-01 Publication of CA1080718A publication Critical patent/CA1080718A/en

Status Expired legal-status Critical Current

Links

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 title claims abstract description 15
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 title description 9
150000001875 compounds Chemical class 0.000 claims abstract description 46
238000000034 method Methods 0.000 claims abstract description 45
230000008569 process Effects 0.000 claims abstract description 38
238000004519 manufacturing process Methods 0.000 claims abstract description 21
239000003513 alkali Substances 0.000 claims abstract description 9
UCFUJBVZSWTHEG-UHFFFAOYSA-N 4-(2-methylphenyl)-2h-triazole Chemical compound CC1=CC=CC=C1C1=CNN=N1 UCFUJBVZSWTHEG-UHFFFAOYSA-N 0.000 claims abstract description 6
230000007935 neutral effect Effects 0.000 claims abstract description 6
239000003960 organic solvent Substances 0.000 claims abstract description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 75
229910052739 hydrogen Inorganic materials 0.000 claims description 40
239000001257 hydrogen Substances 0.000 claims description 40
-1 amine salt cation Chemical class 0.000 claims description 37
125000003545 alkoxy group Chemical group 0.000 claims description 32
125000000217 alkyl group Chemical group 0.000 claims description 26
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 24
125000001624 naphthyl group Chemical group 0.000 claims description 23
150000002431 hydrogen Chemical group 0.000 claims description 21
239000000460 chlorine Substances 0.000 claims description 19
229920000728 polyester Polymers 0.000 claims description 17
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
229910052801 chlorine Inorganic materials 0.000 claims description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
229910052783 alkali metal Inorganic materials 0.000 claims description 11
150000001340 alkali metals Chemical class 0.000 claims description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 10
239000011368 organic material Substances 0.000 claims description 10
BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 claims description 8
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 8
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
229910052700 potassium Inorganic materials 0.000 claims description 8
239000011591 potassium Substances 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 8
238000005282 brightening Methods 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
238000009987 spinning Methods 0.000 claims description 7
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
150000001342 alkaline earth metals Chemical class 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
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 claims description 5
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
239000011734 sodium Substances 0.000 claims description 5
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 claims description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000005111 carboxyalkoxy group Chemical group 0.000 claims description 4
125000000068 chlorophenyl 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
BPJBHWUQHBGEKA-UHFFFAOYSA-N 4-(2-methylphenyl)-2h-benzo[e]benzotriazole Chemical compound CC1=CC=CC=C1C1=CC2=CC=CC=C2C2=NNN=C12 BPJBHWUQHBGEKA-UHFFFAOYSA-N 0.000 claims description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
235000019253 formic acid Nutrition 0.000 claims description 3
125000001188 haloalkyl group Chemical group 0.000 claims description 3
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 3
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
241001465754 Metazoa Species 0.000 claims description 2
SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 claims description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 2
125000003302 alkenyloxy group Chemical group 0.000 claims description 2
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
125000005359 phenoxyalkyl group Chemical group 0.000 claims description 2
235000013311 vegetables Nutrition 0.000 claims description 2
VQCHQSNJLLTVDO-UHFFFAOYSA-N 1-[2-(2-phenylethenyl)phenyl]pyrazole Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1N1C=CC=N1 VQCHQSNJLLTVDO-UHFFFAOYSA-N 0.000 claims 1
ADEHIXXUUTVIPM-UHFFFAOYSA-N 2-[2-(2-phenylethenyl)phenyl]benzotriazole Chemical class C=1C=CC=C(N2N=C3C=CC=CC3=N2)C=1C=CC1=CC=CC=C1 ADEHIXXUUTVIPM-UHFFFAOYSA-N 0.000 claims 1
DIOHCNXUEBUYCM-UHFFFAOYSA-N 4-[2-(2-phenylethenyl)phenyl]-2h-triazole Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1C1=CNN=N1 DIOHCNXUEBUYCM-UHFFFAOYSA-N 0.000 claims 1
150000001339 alkali metal compounds Chemical class 0.000 claims 1
150000001408 amides Chemical class 0.000 claims 1
235000013877 carbamide Nutrition 0.000 claims 1
150000003672 ureas Chemical class 0.000 claims 1
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 19
239000004744 fabric Substances 0.000 description 18
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 14
239000000243 solution Substances 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 11
239000000203 mixture Substances 0.000 description 11
239000002253 acid Substances 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
239000000463 material Substances 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
150000002148 esters Chemical class 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
235000019441 ethanol Nutrition 0.000 description 8
239000004753 textile Substances 0.000 description 8
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical class CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
150000001735 carboxylic acids Chemical class 0.000 description 6
229920000642 polymer Polymers 0.000 description 6
GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
239000004952 Polyamide Substances 0.000 description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
238000004043 dyeing Methods 0.000 description 5
150000002500 ions Chemical class 0.000 description 5
239000000155 melt Substances 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
229920002647 polyamide Polymers 0.000 description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
150000001768 cations Chemical class 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
230000032050 esterification Effects 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
239000008187 granular material Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
239000000049 pigment Substances 0.000 description 4
238000006068 polycondensation reaction Methods 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
238000003756 stirring Methods 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
239000004408 titanium dioxide Substances 0.000 description 4
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000010408 film Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000000758 substrate Substances 0.000 description 3
WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 2
POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
VZIQXGLTRZLBEX-UHFFFAOYSA-N 2-chloro-1-propanol Chemical compound CC(Cl)CO VZIQXGLTRZLBEX-UHFFFAOYSA-N 0.000 description 2
SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
CNGYZEMWVAWWOB-VAWYXSNFSA-N 5-[[4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl]amino]-2-[(e)-2-[4-[[4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulfophenyl]ethenyl]benzenesulfonic acid Chemical class N=1C(NC=2C=C(C(\C=C\C=3C(=CC(NC=4N=C(N=C(NC=5C=CC=CC=5)N=4)N(CCO)CCO)=CC=3)S(O)(=O)=O)=CC=2)S(O)(=O)=O)=NC(N(CCO)CCO)=NC=1NC1=CC=CC=C1 CNGYZEMWVAWWOB-VAWYXSNFSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
102000011632 Caseins Human genes 0.000 description 2
108010076119 Caseins Proteins 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
229920002292 Nylon 6 Polymers 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
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239000004793 Polystyrene Substances 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
230000008901 benefit Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000000969 carrier Substances 0.000 description 2
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 2
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XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
239000000835 fiber Substances 0.000 description 2
244000144992 flock Species 0.000 description 2
WCASXYBKJHWFMY-UHFFFAOYSA-N gamma-methylallyl alcohol Natural products CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 2
239000011521 glass Substances 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
238000001746 injection moulding Methods 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 2
239000004745 nonwoven fabric Substances 0.000 description 2
BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
239000000123 paper Substances 0.000 description 2
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239000004814 polyurethane Substances 0.000 description 2
239000004800 polyvinyl chloride Substances 0.000 description 2
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239000000843 powder Substances 0.000 description 2
238000012545 processing Methods 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
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125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
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239000007857 degradation product Substances 0.000 description 1
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125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
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238000010348 incorporation Methods 0.000 description 1
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239000000543 intermediate Substances 0.000 description 1
239000011872 intimate mixture Substances 0.000 description 1
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239000000990 laser dye Substances 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
229920000126 latex Polymers 0.000 description 1
239000010985 leather Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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239000002184 metal Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000000178 monomer Substances 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
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125000004433 nitrogen atom Chemical group N* 0.000 description 1
125000006574 non-aromatic ring group Chemical group 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
101150066242 outO gene Proteins 0.000 description 1
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150000002924 oxiranes Chemical class 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
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WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
239000005020 polyethylene terephthalate Substances 0.000 description 1
229920006324 polyoxymethylene Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
239000004627 regenerated cellulose Substances 0.000 description 1
230000033458 reproduction Effects 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
WBHHMMIMDMUBKC-QJWNTBNXSA-N ricinoleic acid Chemical class CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-QJWNTBNXSA-N 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
239000000344 soap Substances 0.000 description 1
150000003388 sodium compounds Chemical class 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
239000007858 starting material Substances 0.000 description 1
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
150000003440 styrenes Chemical class 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
238000007669 thermal treatment Methods 0.000 description 1
239000010409 thin film Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
229910000406 trisodium phosphate Inorganic materials 0.000 description 1
235000019801 trisodium phosphate Nutrition 0.000 description 1
SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
239000002759 woven fabric Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/22—Naphthotriazoles
- C07D249/24—Naphthotriazoles with stilbene radicals directly attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
- C07D249/20—Benzotriazoles with aryl radicals directly attached in position 2

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Graft Or Block Polymers (AREA)
Chemical Or Physical Treatment Of Fibers (AREA)
Compositions Of Macromolecular Compounds (AREA)

CA234,833A 1974-09-09 1975-09-05 2-stilbenyl-1,2,3-triazoles which contain carboxyl groups Expired CA1080718A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1222574A CH618057GA3 (en)	1974-09-09	1974-09-09	Process for optically brightening textile organic materials with 2-stilbenyl-1,2,3-triazoles

Publications (1)

Publication Number	Publication Date
CA1080718A true CA1080718A (en)	1980-07-01

Family

ID=4381051

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA234,833A Expired CA1080718A (en)	1974-09-09	1975-09-05	2-stilbenyl-1,2,3-triazoles which contain carboxyl groups

Country Status (8)

Country	Link
JP (1)	JPS5152437A (de)
BE (1)	BE833162A (de)
CA (1)	CA1080718A (de)
CH (1)	CH618057GA3 (de)
DE (2)	DE2539461A1 (de)
ES (1)	ES440784A1 (de)
FR (1)	FR2283894A1 (de)
GB (2)	GB1508330A (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5442479A (en) *	1977-09-12	1979-04-04	Mitsui Toatsu Chemicals	Fluorecent brightening of synthetic fiber material in organic solvent
US4366189A (en) *	1979-12-21	1982-12-28	Ciba-Geigy Corporation	4-Heterocyclyl-4'-vinylstilbenes
US4539161A (en) *	1980-07-25	1985-09-03	Ciba-Geigy Corporation	Amine oxide compounds

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1029792B (de) *	1951-09-06	1958-05-14	Geigy Ag J R	Optische Aufhellungsmittel
DE2010764C3 (de) *	1969-03-07	1975-08-28	Nippon Kayaku K.K., Tokio	4- (2-Triazolyl) -2-cyan-stilbene
BE789446A (fr) *	1971-10-02	1973-03-29	Ciba Geigy	Traitement d'azurants optiques du type triazolyl-stilbene pouvant etre incorpores a des detergents
IT966203B (it) *	1971-10-07	1974-02-11		Sbiancanti alchilbenzossazolilstil benici

1974
- 1974-09-09 CH CH1222574A patent/CH618057GA3/xx not_active IP Right Cessation
1975
- 1975-09-05 DE DE19752539461 patent/DE2539461A1/de not_active Withdrawn
- 1975-09-05 DE DE19752539537 patent/DE2539537A1/de not_active Ceased
- 1975-09-05 CA CA234,833A patent/CA1080718A/en not_active Expired
- 1975-09-08 GB GB36884/75A patent/GB1508330A/en not_active Expired
- 1975-09-08 ES ES440784A patent/ES440784A1/es not_active Expired
- 1975-09-08 FR FR7527429A patent/FR2283894A1/fr active Granted
- 1975-09-08 BE BE159818A patent/BE833162A/xx unknown
- 1975-09-08 GB GB36883/75A patent/GB1508329A/en not_active Expired
- 1975-09-09 JP JP50108617A patent/JPS5152437A/ja active Pending

Also Published As

Publication number	Publication date
CH618057B (de)
GB1508329A (en)	1978-04-19
BE833162A (fr)	1976-03-08
JPS5152437A (en)	1976-05-10
DE2539461A1 (de)	1976-03-18
ES440784A1 (es)	1977-03-16
CH618057GA3 (en)	1980-07-15
GB1508330A (en)	1978-04-19
FR2283894B1 (de)	1978-04-07
FR2283894A1 (fr)	1976-04-02
DE2539537A1 (de)	1976-03-18

Legal Events

Date	Code	Title	Description
1997-07-02	MKEX	Expiry
2023-08-15	MKEX	Expiry	Effective date: 19970702

Publication	Publication Date	Title
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US3849163A (en)	1974-11-19	Process for the optical brightening of organic materials
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US4317782A (en)	1982-03-02	Distyryl compounds
US3682946A (en)	1972-08-08	New bis-naphthoxazolyl-derivatives
US3956395A (en)	1976-05-11	Distyrylbenzene disulfone derivatives
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CA1080718A (en)	1980-07-01	2-stilbenyl-1,2,3-triazoles which contain carboxyl groups
US3825534A (en)	1974-07-23	Styryl compounds,processes for their manufacture and their use
US3351591A (en)	1967-11-07	4-azolyl-4'-oxdiazolyl-stilbenes
US4014870A (en)	1977-03-29	Stilbene compounds
DE2405056A1 (de)	1974-08-15	Neue benzofuran-derivate, verfahren zu deren herstellung und ihre verwendung als optische aufheller
US4166176A (en)	1979-08-28	Fluorescent dyestuffs
US3850914A (en)	1974-11-26	Novel alkyl-benzoxazolyl-p-phenyl stilbenes
US4206072A (en)	1980-06-03	Benzoxazolyl-phenyl-stilbenes
US3328310A (en)	1967-06-27	Optically brightened organic compositions
EP0002042A1 (de)	1979-05-30	Diamino-1,3,5-triazinylstilbenverbindungen, Verfahren zu deren Herstellung und ihre Verwendung als optische Aufheller
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US4013713A (en)	1977-03-22	Diarylvinyl-dihydrophenanthrene compounds
US4013642A (en)	1977-03-22	Heterocyclic compounds containing sulpho groups
US4172045A (en)	1979-10-23	Process for the manufacture of 2-stilbenyl-1,2,3-triazoles which contain carboxyl groups, novel 2-stilbenyl-1,2,3-triazoles which contain carboxyl groups and the use thereof as fluorescent brighteners
DE2309614A1 (de)	1973-09-20	Azolverbindungen, verfahren zu deren herstellung und deren verwendung
US4508784A (en)	1985-04-02	4-Styryl-4'-vinylbiphenyls, the production thereof and use thereof as fluorescent
US4140852A (en)	1979-02-20	Triazinyl styryl-benzoxazole fluorescent dyestuffs
US3758460A (en)	1973-09-11	Styryl compounds