CH530439A - Verwendung von heterocyclisch substituierten Vinyl-v-triazolen der Cumarinreihe zum Aufhellen von nichttextilen organischen Materialien - Google Patents
Verwendung von heterocyclisch substituierten Vinyl-v-triazolen der Cumarinreihe zum Aufhellen von nichttextilen organischen MaterialienInfo
- Publication number
- CH530439A CH530439A CH1735470A CH1735470A CH530439A CH 530439 A CH530439 A CH 530439A CH 1735470 A CH1735470 A CH 1735470A CH 1735470 A CH1735470 A CH 1735470A CH 530439 A CH530439 A CH 530439A
- Authority
- CH
- Switzerland
- Prior art keywords
- triazole
- vinyl
- formula
- phenyl
- textile
- Prior art date
Links
- 239000004753 textile Substances 0.000 title claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 3
- 230000003287 optical effect Effects 0.000 claims description 8
- 239000011368 organic material Substances 0.000 claims description 5
- 125000000332 coumarinyl group Chemical class O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 4
- 238000005282 brightening Methods 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 230000021615 conjugation Effects 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
- 238000009833 condensation Methods 0.000 abstract description 4
- 230000005494 condensation Effects 0.000 abstract description 4
- 239000004952 Polyamide Substances 0.000 abstract description 2
- 229920002647 polyamide Polymers 0.000 abstract description 2
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- 229920002554 vinyl polymer Polymers 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- -1 polyethylene Polymers 0.000 description 15
- 150000001875 compounds Chemical group 0.000 description 14
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 238000009987 spinning Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- RBNQBFQJAPNXMI-UHFFFAOYSA-N 7-hydrazinyl-3-phenylchromen-2-one Chemical compound O=C1OC2=CC(NN)=CC=C2C=C1C1=CC=CC=C1 RBNQBFQJAPNXMI-UHFFFAOYSA-N 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000004775 coumarins Chemical class 0.000 description 4
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 235000011056 potassium acetate Nutrition 0.000 description 4
- 238000006798 ring closing metathesis reaction Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000003852 triazoles Chemical group 0.000 description 3
- OVGLVOLWBBGQHS-DUXPYHPUSA-N (1e)-1-hydroxyiminopropan-2-one Chemical compound CC(=O)\C=N\O OVGLVOLWBBGQHS-DUXPYHPUSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-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
- 230000009471 action Effects 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper 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
- 230000007717 exclusion Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- OENLEHTYJXMVBG-UHFFFAOYSA-N pyridine;hydrate Chemical compound [OH-].C1=CC=[NH+]C=C1 OENLEHTYJXMVBG-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
- ILWGLICVVNLLOB-UHFFFAOYSA-N 2-hydroxy-4-(2H-triazol-4-yl)benzaldehyde Chemical compound OC1=C(C=O)C=CC(=C1)C=1N=NNC1 ILWGLICVVNLLOB-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- VOMRTQQGXWPTJK-UHFFFAOYSA-N 3,5-dimethyl-1-phenylpyrazole-4-carbaldehyde Chemical compound CC1=C(C=O)C(C)=NN1C1=CC=CC=C1 VOMRTQQGXWPTJK-UHFFFAOYSA-N 0.000 description 1
- ZQSRZBGBCSSZEK-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-7-hydrazinylchromen-2-one Chemical compound ClC1=C(C=CC(=C1)Cl)C=1C(OC2=CC(=CC=C2C1)NN)=O ZQSRZBGBCSSZEK-UHFFFAOYSA-N 0.000 description 1
- CLFHFRQFMGHBIB-UHFFFAOYSA-N 3-(3-chlorophenyl)-7-hydrazinylchromen-2-one Chemical compound O=C1OC2=CC(NN)=CC=C2C=C1C1=CC=CC(Cl)=C1 CLFHFRQFMGHBIB-UHFFFAOYSA-N 0.000 description 1
- IGXQUTUFZNRDOC-UHFFFAOYSA-N 3-(4-chlorophenyl)-7-hydrazinylchromen-2-one Chemical compound O=C1OC2=CC(NN)=CC=C2C=C1C1=CC=C(Cl)C=C1 IGXQUTUFZNRDOC-UHFFFAOYSA-N 0.000 description 1
- VQAFWAZFVKGDIG-UHFFFAOYSA-N 3-(4-fluorophenyl)-7-hydrazinylchromen-2-one Chemical compound FC1=CC=C(C=C1)C=1C(OC2=CC(=CC=C2C1)NN)=O VQAFWAZFVKGDIG-UHFFFAOYSA-N 0.000 description 1
- QWZHDKGQKYEBKK-UHFFFAOYSA-N 3-aminochromen-2-one Chemical class C1=CC=C2OC(=O)C(N)=CC2=C1 QWZHDKGQKYEBKK-UHFFFAOYSA-N 0.000 description 1
- HCDKAKHHXNYECW-UHFFFAOYSA-N 3-hydrazinylchromen-2-one Chemical class C1=CC=C2OC(=O)C(NN)=CC2=C1 HCDKAKHHXNYECW-UHFFFAOYSA-N 0.000 description 1
- HWDSXZLYIKESML-UHFFFAOYSA-N 3-phenylchromen-2-one Chemical class O=C1OC=2C=CC=CC=2C=C1C1=CC=CC=C1 HWDSXZLYIKESML-UHFFFAOYSA-N 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- GQPYONBHVVYRKV-UHFFFAOYSA-N 4,6-diphenyl-1,3,5-triazine-2-carbaldehyde Chemical compound N=1C(C=O)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 GQPYONBHVVYRKV-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ROJGJNINTRCMBL-UHFFFAOYSA-N 5-(4-chlorophenyl)furan-2-carbaldehyde Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(C=O)O1 ROJGJNINTRCMBL-UHFFFAOYSA-N 0.000 description 1
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 1
- SHNRXUWGUKDPMA-UHFFFAOYSA-N 5-formyl-2-furoic acid Chemical compound OC(=O)C1=CC=C(C=O)O1 SHNRXUWGUKDPMA-UHFFFAOYSA-N 0.000 description 1
- PUQKOVRPNHYQIY-UHFFFAOYSA-N 5-formylfuran-2-carbonitrile Chemical compound O=CC1=CC=C(C#N)O1 PUQKOVRPNHYQIY-UHFFFAOYSA-N 0.000 description 1
- NVEHHZVMTJYIQT-UHFFFAOYSA-N 5-formylfuran-2-sulfonic acid;sodium Chemical compound [Na].OS(=O)(=O)C1=CC=C(C=O)O1 NVEHHZVMTJYIQT-UHFFFAOYSA-N 0.000 description 1
- KATWEGNKOJBEPF-UHFFFAOYSA-N 5-methylsulfonylfuran-2-carbaldehyde Chemical compound CS(=O)(=O)C1=CC=C(C=O)O1 KATWEGNKOJBEPF-UHFFFAOYSA-N 0.000 description 1
- MHZARHIXVLWEJX-UHFFFAOYSA-N 7-hydrazinyl-3-(3-methylphenyl)chromen-2-one Chemical compound CC=1C=C(C=CC1)C=1C(OC2=CC(=CC=C2C1)NN)=O MHZARHIXVLWEJX-UHFFFAOYSA-N 0.000 description 1
- LOTYTBMBDRFSKA-UHFFFAOYSA-N 7-hydrazinyl-6-methyl-3-phenylchromen-2-one Chemical compound O=C1OC=2C=C(NN)C(C)=CC=2C=C1C1=CC=CC=C1 LOTYTBMBDRFSKA-UHFFFAOYSA-N 0.000 description 1
- IYEOAPOYGIQKQF-UHFFFAOYSA-N C(#N)C=1C=C(C=CC1)C=1C(OC2=CC(=CC=C2C1)NN)=O Chemical compound C(#N)C=1C=C(C=CC1)C=1C(OC2=CC(=CC=C2C1)NN)=O IYEOAPOYGIQKQF-UHFFFAOYSA-N 0.000 description 1
- JWONWMLBGNQERM-UHFFFAOYSA-N C(=O)(O)C=1C=C(C=CC1)C=1C(OC2=CC(=CC=C2C1)NN)=O Chemical compound C(=O)(O)C=1C=C(C=CC1)C=1C(OC2=CC(=CC=C2C1)NN)=O JWONWMLBGNQERM-UHFFFAOYSA-N 0.000 description 1
- PNOIBJUAJXOBPK-UHFFFAOYSA-N ClC=1C=C(C=CC1Cl)C=1C(OC2=CC(=CC=C2C1)NN)=O Chemical compound ClC=1C=C(C=CC1Cl)C=1C(OC2=CC(=CC=C2C1)NN)=O PNOIBJUAJXOBPK-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
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- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000010953 base metal Substances 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
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- FPNANULSSQHZSS-UHFFFAOYSA-N ethyl 5-formylfuran-2-carboxylate Chemical compound CCOC(=O)C1=CC=C(C=O)O1 FPNANULSSQHZSS-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 150000002923 oximes Chemical class 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
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- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
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- 238000006116 polymerization reaction Methods 0.000 description 1
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- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 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
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/45—Heterocyclic compounds having sulfur in the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3472—Five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Detergent Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Artificial Filaments (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1735470A CH530439A (de) | 1969-06-13 | 1969-06-13 | Verwendung von heterocyclisch substituierten Vinyl-v-triazolen der Cumarinreihe zum Aufhellen von nichttextilen organischen Materialien |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1735470A CH530439A (de) | 1969-06-13 | 1969-06-13 | Verwendung von heterocyclisch substituierten Vinyl-v-triazolen der Cumarinreihe zum Aufhellen von nichttextilen organischen Materialien |
| CH905569A CH511318A (de) | 1969-06-13 | 1969-06-13 | Verwendung einer Verbindung der Cumarinylstyryltriazolreihe zum optischen Aufhellen von Textilien |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH530439A true CH530439A (de) | 1972-11-15 |
Family
ID=4347822
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1735570A CH530440A (de) | 1969-06-13 | 1969-06-13 | Verwendung einer Verbindung der Cumarinylstryryltriazolreihe zum optischen Aufhellen von nichtextilen organischen Materialien |
| CH905569A CH511318A (de) | 1969-06-13 | 1969-06-13 | Verwendung einer Verbindung der Cumarinylstyryltriazolreihe zum optischen Aufhellen von Textilien |
| CH1735470A CH530439A (de) | 1969-06-13 | 1969-06-13 | Verwendung von heterocyclisch substituierten Vinyl-v-triazolen der Cumarinreihe zum Aufhellen von nichttextilen organischen Materialien |
| CH1735370A CH527874A (de) | 1969-06-13 | 1969-06-13 | Verwendung von Arylvinyl-v-triazolen zum optischen Aufhellen von nichttextilen organischen Materialien |
| CH905569D CH905569A4 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-06-13 | 1969-06-13 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1735570A CH530440A (de) | 1969-06-13 | 1969-06-13 | Verwendung einer Verbindung der Cumarinylstryryltriazolreihe zum optischen Aufhellen von nichtextilen organischen Materialien |
| CH905569A CH511318A (de) | 1969-06-13 | 1969-06-13 | Verwendung einer Verbindung der Cumarinylstyryltriazolreihe zum optischen Aufhellen von Textilien |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1735370A CH527874A (de) | 1969-06-13 | 1969-06-13 | Verwendung von Arylvinyl-v-triazolen zum optischen Aufhellen von nichttextilen organischen Materialien |
| CH905569D CH905569A4 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-06-13 | 1969-06-13 |
Country Status (8)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3844781A (en) * | 1968-12-30 | 1974-10-29 | Canon Kk | Organic photoconductive materials |
| JPS52134264U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1976-04-08 | 1977-10-12 | ||
| DE19500195A1 (de) * | 1995-01-05 | 1996-07-11 | Bayer Ag | Verwendung weißgetönter Kunststoffe zum Weißtönen von Papierstreichmassen und derart weißgetönte Papierstreichmassen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1498700A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1965-10-04 | 1968-01-10 |
-
1969
- 1969-06-13 CH CH1735570A patent/CH530440A/de not_active IP Right Cessation
- 1969-06-13 CH CH905569A patent/CH511318A/de not_active IP Right Cessation
- 1969-06-13 CH CH1735470A patent/CH530439A/de not_active IP Right Cessation
- 1969-06-13 CH CH1735370A patent/CH527874A/de unknown
- 1969-06-13 CH CH905569D patent/CH905569A4/xx unknown
-
1970
- 1970-06-04 US US00043567A patent/US3714152A/en not_active Expired - Lifetime
- 1970-06-04 US US43564A patent/US3696097A/en not_active Expired - Lifetime
- 1970-06-12 BE BE751871D patent/BE751871A/xx unknown
- 1970-06-12 NL NL7008647A patent/NL7008647A/xx unknown
- 1970-06-12 DE DE19702029096 patent/DE2029096A1/de active Pending
- 1970-06-12 JP JP45050679A patent/JPS4837972B1/ja active Pending
- 1970-06-12 GB GB2867270A patent/GB1317291A/en not_active Expired
- 1970-06-12 BE BE751872D patent/BE751872A/xx unknown
- 1970-06-12 JP JP45050678A patent/JPS4837968B1/ja active Pending
- 1970-06-12 FR FR7021674A patent/FR2051162A5/fr not_active Expired
- 1970-06-12 GB GB2867170A patent/GB1325156A/en not_active Expired
- 1970-06-12 FR FR7021673A patent/FR2051161A5/fr not_active Expired
- 1970-06-12 DE DE19702029122 patent/DE2029122A1/de active Pending
- 1970-06-12 NL NL7008648A patent/NL7008648A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7008648A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-15 |
| FR2051161A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-04-02 |
| BE751872A (fr) | 1970-12-14 |
| JPS4837972B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-11-14 |
| CH511318A (de) | 1971-04-30 |
| CH905569A4 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-04-30 |
| CH527874A (de) | 1972-09-15 |
| FR2051162A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-04-02 |
| US3714152A (en) | 1973-01-30 |
| US3696097A (en) | 1972-10-03 |
| JPS4837968B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-11-14 |
| GB1317291A (en) | 1973-05-16 |
| NL7008647A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-15 |
| BE751871A (fr) | 1970-12-14 |
| CH530440A (de) | 1972-11-15 |
| GB1325156A (en) | 1973-08-01 |
| DE2029096A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-23 |
| DE2029122A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |