EP0023028B1 - Mischungen von optischen Aufhellern und deren Verwendung - Google Patents
Mischungen von optischen Aufhellern und deren Verwendung Download PDFInfo
- Publication number
- EP0023028B1 EP0023028B1 EP80104163A EP80104163A EP0023028B1 EP 0023028 B1 EP0023028 B1 EP 0023028B1 EP 80104163 A EP80104163 A EP 80104163A EP 80104163 A EP80104163 A EP 80104163A EP 0023028 B1 EP0023028 B1 EP 0023028B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- denotes
- group
- phenyl
- alkoxy
- Prior art date
- 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
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 43
- 230000003287 optical effect Effects 0.000 title claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 74
- -1 C1-C9 alkyl Chemical group 0.000 claims description 60
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 43
- 125000003545 alkoxy group Chemical group 0.000 claims description 41
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 26
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 150000003254 radicals Chemical class 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 15
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 13
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000005605 benzo group Chemical group 0.000 claims description 8
- 150000003857 carboxamides Chemical class 0.000 claims description 8
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- 125000004442 acylamino group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000005504 styryl group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000003944 tolyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 229940124530 sulfonamide Drugs 0.000 claims description 5
- 150000003456 sulfonamides Chemical class 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical group OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 3
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 3
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- MALIONKMKPITBV-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)CC1=CC=C(O)C(Cl)=C1 MALIONKMKPITBV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
- HJMZMZRCABDKKV-UHFFFAOYSA-N carbonocyanidic acid Chemical compound OC(=O)C#N HJMZMZRCABDKKV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- 125000001725 pyrenyl group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- NFGODEMQGQNUKK-UHFFFAOYSA-M [6-(diethylamino)-9-(2-octadecoxycarbonylphenyl)xanthen-3-ylidene]-diethylazanium;chloride Chemical group [Cl-].CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C1=C2C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C21 NFGODEMQGQNUKK-UHFFFAOYSA-M 0.000 claims 1
- 238000005282 brightening Methods 0.000 claims 1
- 0 N#CC1C=CC=C[C@]1C=C*1C=CC(C=Cc(cccc2)c2C#N)=CC1 Chemical compound N#CC1C=CC=C[C@]1C=C*1C=CC(C=Cc(cccc2)c2C#N)=CC1 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 230000008569 process Effects 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000370 acceptor Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- USLPZCOPYRKTGY-UHFFFAOYSA-N 2-(2-phenylethenyl)benzonitrile Chemical compound N#CC1=CC=CC=C1C=CC1=CC=CC=C1 USLPZCOPYRKTGY-UHFFFAOYSA-N 0.000 description 2
- RBABXJPJIHMBBP-UHFFFAOYSA-N 2-[2-[4-[2-(2-cyanophenyl)ethenyl]phenyl]ethenyl]benzonitrile Chemical compound N#CC1=CC=CC=C1C=CC(C=C1)=CC=C1C=CC1=CC=CC=C1C#N RBABXJPJIHMBBP-UHFFFAOYSA-N 0.000 description 2
- KIAAMJMIIHTGBH-UHFFFAOYSA-N 4-[2-[4-[2-(4-cyanophenyl)ethenyl]phenyl]ethenyl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C=CC(C=C1)=CC=C1C=CC1=CC=C(C#N)C=C1 KIAAMJMIIHTGBH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 125000003106 haloaryl group Chemical group 0.000 description 2
- 125000005059 halophenyl group Chemical group 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000009021 linear effect Effects 0.000 description 2
- 239000000979 synthetic dye Substances 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZWTSHXKQOKSKMB-UHFFFAOYSA-N 2-[2-(1-cyano-2-phenylethenyl)phenyl]-3-phenylprop-2-enenitrile Chemical class C=1C=CC=C(C(=CC=2C=CC=CC=2)C#N)C=1C(C#N)=CC1=CC=CC=C1 ZWTSHXKQOKSKMB-UHFFFAOYSA-N 0.000 description 1
- WQUHPLQCUQJSQW-UHFFFAOYSA-N 4-(2-phenylethenyl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C=CC1=CC=CC=C1 WQUHPLQCUQJSQW-UHFFFAOYSA-N 0.000 description 1
- JGDLUGKNDDIMSQ-UHFFFAOYSA-N Bc1ccc(C)cc1 Chemical compound Bc1ccc(C)cc1 JGDLUGKNDDIMSQ-UHFFFAOYSA-N 0.000 description 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- FQAWBFKSPCQARO-BUHFOSPRSA-N N#Cc1ccccc1/C=C/c1ccc(C=[ClH]=[I]c(cccc2)c2C#N)cc1 Chemical compound N#Cc1ccccc1/C=C/c1ccc(C=[ClH]=[I]c(cccc2)c2C#N)cc1 FQAWBFKSPCQARO-BUHFOSPRSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical class C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical class OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical class CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- DIORMHZUUKOISG-UHFFFAOYSA-N sulfoformic acid Chemical compound OC(=O)S(O)(=O)=O DIORMHZUUKOISG-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910001868 water Inorganic materials 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- D06L4/65—Optical bleaching or brightening with mixtures of optical brighteners
Definitions
- optical brighteners Venkataraman, The Chemistry of Synthetic Dyes, Vol. V, Chapter VIII.
- French Patent No. 1,415,977 it is also known from French Patent No. 1,415,977 to use mixtures of optical brighteners consisting of 1,4-bis (cyano-2-styryl) benzene, 1,4-bis (cyano-4-styryl) benzene and 4- (cyano-2-styryl) -1- (cyano-4-styryl) benzene.
- a mixture which consists of one of these isomeric bis (cyanostyryl) benzenes, namely 1,4-bis (cyano-2-styryl) benzene and a brightener from the series of naphthalimide derivatives (Chemical Abstracts Vol. 83 , No. 61504 c). It has now been found that the effect of these known mixtures can be exceeded if the mixture known from the French patent mentioned is mixed with other brighteners of the formulas 4 to 8 listed below.
- alkyl and alkoxy groups and other groups derived therefrom contain 1 to 4 carbon atoms.
- the term “non-chromophoric substituents” is to be understood as meaning alkyl, alkoxy, aryl, aralkyl, trifluoromethyl, cycloalkyl, halogen, alkylsulfonyl, carboxy, sulfonic acid, cyano, carbonamide, sulfonamide, carboxylic acid alkyl ester, sulfonic acid alkyl ester.
- component B consisting of one or more compounds of the formulas 2b-6b where R 1 in the 5-position is a hydrogen or chlorine atom, a methyl or phenyl group and R 2 is a hydrogen atom or R 1 and R 2 are both a methyl group in the 5,6- or 5,7-position, n 0 or 1 and B.
- R 14 is (C 1 -C 6 ) alkyl, (C 1 -C 6 ) chloroalkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, hydroxy (C 1 -C 4 ) alkyl or a group of the formula - (CH 2 CH 2 O) n ⁇ R, n 2 or 3 and R hydrogen or (C 1 -C 4 ) alkyl, R, 5 phenyl, halophenyl, (C 1 -C 4 ) -alkylphenyl or (C 1 -C 4 ) -alkoxiphenyl, R 22 is (C 1 -C 4 ) -alkyl and R 23 is cyano or carbo- (C 1 -C 4 ) -alkoxy, where R 3 is hydrogen or (C 1 -C 6 ) alkyl, (C 1 -C 6 ) chloroalkyl, (C 1 -C 4 ) alk
- component B consisting of one or more compounds of the following formulas: wherein R 1 and R 2 in the 5,6-position methyl and B carbomethoxy, R hydrogen, R 1 hydrogen or methyl in the 5-position and B carbomethoxy, cyano or a group of the formulas wherein R 14 and R 22 are (C 1 -C 3 ) alkyl and R 15 is phenyl, 4-methylphenyl or 4-methoxyphenyl, or R 1 is hydrogen, methyl or t-butyl in the 5-position, R 2 is hydrogen or methyl in 7-position and B is phenyl, where R 3 is hydrogen or methoxy, or or where R 2 is hydrogen or methyl.
- component A Mixtures of the following composition are particularly preferred as component A: the proportion of compounds 1 and 3 should be approximately the same.
- the proportion of the individual compounds 1 to 3 in component A can fluctuate within the limits specified, preference being given to mixtures which contain the compounds 1 and 3 in approximately equal parts. From the limits given above for the weight ratios of compounds 1 to 3, it follows that the proportion of compounds 1 and 3 can be 0% and the proportion of compound 2 can be 100%. In this case there is pure connection 2. It is understood that the composition of component A is chosen within the various limits given above so that the sum of all individual compounds is 100%.
- the ratio of compounds 10 and 11 determines the composition of the mixture. If the proportion of 10 is higher, the proportion of compound 1 increases at the expense of compound 3, if the proportion of compound 11 is higher, the proportion of compound 3 in mixtures will be higher than 1.
- one of the symbols X or Q represents an aldehyde group and the other symbol a group of the formulas where R represents an optionally substituted alkyl radical having preferably 1-6 C atoms, an aryl radical preferably phenyl, a cycloalkyl radical or an aralkyl radical, preferably benzyl.
- the process is preferably carried out in solvents in the presence of a proton acceptor.
- solvents which may be mentioned are hydrocarbons such as toluene, xylene, alcohols such as methanol, ethanol, isopropanol, butanol, glycols, hexanols, cyclohexanols, and furthermore ethers such as diisopropyl ether, tetrahydrofuran, dioxane and dimethyl sulfoxide.
- Polar organic solvents such as formamide, dimethylformamide and N-methylpyrrolidone are particularly suitable, with dimethylformamide being particularly emphasized.
- Suitable proton acceptors are primarily basic compounds, such as alkali or alkaline earth metal hydroxides, alcoholates or amides, strongly basic amines and anion exchange resins in the hydroxyl form.
- alkali hydrodes in particular potassium hydroxide, is preferred.
- the reaction temperature depends on the type of components to be reacted, in particular on the type of organic compound containing carbonyl groups and the proton acceptor; it is between - 10 ° C and + 100 ° C, advantageously between 0 ° -50 ° C.
- a preferred embodiment is to bring the reactants together at lower temperatures and to complete the reaction at a higher temperature.
- the claimed process can be carried out, for example, by introducing the proton acceptor in the solvent and adding a solution of the reaction components 9-11 in the solvent, but it is also possible to introduce the compounds 9-11 and adding them to the proteone acceptors.
- a further embodiment consists in presenting the compounds 9-11, in which X or Q represents a group of the formula 12a-d, then first adding the proton acceptor and then the aldehyde component. The reaction generally takes place with intense heat so that cooling may be necessary.
- the reactor mixture is worked up in a known manner, e.g. by adding methanol or ethanol and separating the precipitated products.
- the product mixtures obtained in this way can be analyzed and characterized by HPLC (high pressure liquid chromatography).
- the starting compounds of the formulas 9-11 are known or can be prepared by known processes.
- R, " and R 2" are hydrogen or alkyl and B "is a group of the formulas ⁇ CN or ⁇ COOalkyl and R, 4 .
- Alkyl or methoxyethyl means.
- the following compounds under formula 4 are of particular importance: and
- the mixing ratio for the individual components is between 0.05 and 0.95 parts by weight for component A and correspondingly 0.95 to 0.05 parts by weight for the other compounds of the formulas 4 to 8.
- These compounds of the formulas 4 to 8 can be used individually or in any mixture with one another, the mixing ratio of these compounds with one another being completely uncritical and being able to be varied as desired.
- a mixing ratio of 5 to 50% by weight for component A and 95 to 50% by weight of one or more brighteners of the formulas 4 to 8 (component B) is preferred.
- the optimal mixing ratio of all compounds depends in individual cases on the structure of the respective compounds and can be easily determined by simple preliminary tests.
- the individual components are dispersed in a liquid medium e.g. Water brought into the commercial form.
- the individual components can be dispersed individually and the dispersions can then be added together.
- the individual components can also be mixed together in bulk and then dispersed together. This dispersion process takes place in the usual way in ball mills, colloid mills, bead mills or dispersion kneaders.
- the mixtures according to the invention are particularly suitable for lightening textile material made from linear polyesters, polyamides and acetyl cellulose. However, these mixtures can also be used with good results in mixed fabrics which consist of linear polyesters and other synthetic or natural fiber materials, in particular fibers containing hydroxyl groups, in particular cotton.
- optical brighteners are applied under the conditions customary for the use of optical brighteners, for example using the exhaust process at 90 ° C. to 130 ° C. with or without the addition of accelerators (carriers) or using the thermosol process.
- the water-insoluble brighteners and the mixtures according to the invention can also be used in organic solvents, e.g. Perchlorethylene, fluorinated hydrocarbons can be used in solution.
- the textile material can be treated in the exhaust process with the solvent liquor which contains the optical brightener, or one can impregnate, splash, spray the textile material with the brightener-containing solvent liquor and then dry at temperatures of 120-220 ° C, the optical brightener being used is completely fixed in the fiber.
- the material is squeezed between rollers with a padder so that a moisture absorption of approx. 80% results. This corresponds to an absorption of optical brighteners on the goods of 0.064%.
- the material which had been blocked in this way was then thermosolated on a stenter for 30 seconds at 170 ° (Table I) or 210 ° (Table 11).
- the specified degrees of whiteness according to Ganz were obtained. The degrees of whiteness were measured using a DMC-25 reflectance spectrophotometer. (Carl Zeiss company, Oberkochen).
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
- Paper (AREA)
- Prostheses (AREA)
- Dental Preparations (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT80104163T ATE2017T1 (de) | 1979-07-21 | 1980-07-16 | Mischungen von optischen aufhellern und deren verwendung. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792929687 DE2929687A1 (de) | 1979-07-21 | 1979-07-21 | Mischungen von optischen aufhellern |
| DE2929687 | 1979-07-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0023028A1 EP0023028A1 (de) | 1981-01-28 |
| EP0023028B1 true EP0023028B1 (de) | 1982-12-15 |
Family
ID=6076455
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP80104163A Expired EP0023028B1 (de) | 1979-07-21 | 1980-07-16 | Mischungen von optischen Aufhellern und deren Verwendung |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4330427A (da) |
| EP (1) | EP0023028B1 (da) |
| JP (1) | JPS5618655A (da) |
| AT (1) | ATE2017T1 (da) |
| AU (1) | AU533417B2 (da) |
| BR (1) | BR8004478A (da) |
| CA (1) | CA1151806A (da) |
| DE (2) | DE2929687A1 (da) |
| ES (1) | ES493376A0 (da) |
| ZA (1) | ZA804365B (da) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3313332A1 (de) * | 1983-04-13 | 1984-10-18 | Hoechst Ag, 6230 Frankfurt | Mischungen von optischen aufhellern zum aufhellen von polyvinylchlorid |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH650792A5 (en) * | 1979-12-13 | 1985-08-15 | Ciba Geigy Ag | Optical brighteners from bisstyrylbenzene compounds and preparation thereof |
| DE3070041D1 (en) * | 1979-12-13 | 1985-03-07 | Ciba Geigy Ag | Optical brighteners from bistyryl benzene, process for their preparation and their use |
| DE3001065A1 (de) * | 1980-01-12 | 1981-07-16 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von optischen aufhellern |
| DE3027479A1 (de) * | 1980-07-19 | 1982-03-04 | Hoechst Ag, 6000 Frankfurt | Mischungen von optischen aufhellern und deren verwendung |
| DE3104992A1 (de) * | 1981-02-12 | 1982-08-26 | Hoechst Ag, 6000 Frankfurt | "mischungen von optischen aufhellern" |
| DE3339383A1 (de) * | 1983-10-29 | 1985-05-09 | Bayer Ag, 5090 Leverkusen | Distyrylverbindungen |
| JPS60217999A (ja) * | 1984-03-31 | 1985-10-31 | 株式会社新潟鐵工所 | 流体荷役装置 |
| US4778622A (en) * | 1986-03-21 | 1988-10-18 | Ciba-Geigy Corporation | Mixtures of fluorescent whitening agents |
| EP0252009B1 (de) * | 1986-07-01 | 1990-08-01 | Ciba-Geigy Ag | 1,4-Distryrylbenzolverbindungen und deren Mischungen mit anderen 1,4-Distryrylbenzolverbindungen |
| CH671956A5 (da) * | 1987-01-29 | 1989-10-13 | Ciba Geigy Ag | |
| US4830763A (en) * | 1987-02-26 | 1989-05-16 | Ciba-Geigy Corporation | Process for increasing the degree of whiteness of polyester-containing textile material |
| DE3878550D1 (de) * | 1987-11-27 | 1993-03-25 | Ciba Geigy Ag | Aufhellerdispersion. |
| DE3878540D1 (de) * | 1987-11-27 | 1993-03-25 | Ciba Geigy Ag | Aufhellerdispersion. |
| US6492032B1 (en) | 2000-10-12 | 2002-12-10 | Eastman Chemical Company | Multi-component optically brightened polyolefin blend |
| DE10219993A1 (de) * | 2002-05-03 | 2003-11-20 | Basf Ag | Verfahren zum Aufhellen von textilen Materialien |
| ES2316862T3 (es) * | 2002-12-10 | 2009-04-16 | Ciba Holding Inc. | Mezclas de agentes de blanqueo fluorescentes. |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1469821B2 (de) * | 1959-06-24 | 1972-03-23 | Badische Anilin & Soda Fabrik AG, 6700 Ludwigshafen | Optische Aufheller für makromolekulare organische Stoffe |
| CH533670A (de) * | 1968-12-05 | 1973-02-15 | Ciba Geigy Ag | Optische Aufhellmittel enthaltende anorganische Weisspigmente |
| DE2037854C2 (de) * | 1970-07-30 | 1983-07-07 | Bayer Ag, 5090 Leverkusen | 3-(4-Chlor-1-pyrazolyl)-7-v-triazol-2-yl-cumarin-Verbindungen und deren Verwendung zum optischen Aufhellen |
| JPS51100522A (ja) * | 1975-03-01 | 1976-09-04 | Kubota Ltd | Sagyokiratsukaboshisochi |
| JPS544973A (en) * | 1977-06-13 | 1979-01-16 | Daiken Trade & Industry | Waterproof treatment for board |
-
1979
- 1979-07-21 DE DE19792929687 patent/DE2929687A1/de not_active Withdrawn
-
1980
- 1980-07-15 ES ES493376A patent/ES493376A0/es active Granted
- 1980-07-16 EP EP80104163A patent/EP0023028B1/de not_active Expired
- 1980-07-16 AT AT80104163T patent/ATE2017T1/de not_active IP Right Cessation
- 1980-07-16 US US06/169,296 patent/US4330427A/en not_active Expired - Lifetime
- 1980-07-16 DE DE8080104163T patent/DE3061345D1/de not_active Expired
- 1980-07-18 JP JP9769380A patent/JPS5618655A/ja active Granted
- 1980-07-18 ZA ZA00804365A patent/ZA804365B/xx unknown
- 1980-07-18 CA CA000356458A patent/CA1151806A/en not_active Expired
- 1980-07-18 BR BR8004478A patent/BR8004478A/pt not_active IP Right Cessation
- 1980-07-18 AU AU60636/80A patent/AU533417B2/en not_active Ceased
Non-Patent Citations (1)
| Title |
|---|
| "The Chemistry of Synthetic Dyes", Band V, Kapital VIII, Venkataraman * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3313332A1 (de) * | 1983-04-13 | 1984-10-18 | Hoechst Ag, 6230 Frankfurt | Mischungen von optischen aufhellern zum aufhellen von polyvinylchlorid |
Also Published As
| Publication number | Publication date |
|---|---|
| ES8105055A1 (es) | 1981-05-16 |
| BR8004478A (pt) | 1981-01-27 |
| AU6063680A (en) | 1981-01-22 |
| ES493376A0 (es) | 1981-05-16 |
| ATE2017T1 (de) | 1982-12-15 |
| ZA804365B (en) | 1981-07-29 |
| JPS5618655A (en) | 1981-02-21 |
| DE3061345D1 (en) | 1983-01-20 |
| JPH0116867B2 (da) | 1989-03-28 |
| AU533417B2 (en) | 1983-11-24 |
| DE2929687A1 (de) | 1981-02-12 |
| EP0023028A1 (de) | 1981-01-28 |
| US4330427A (en) | 1982-05-18 |
| CA1151806A (en) | 1983-08-16 |
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