DE1930307C3 - Kationische Derivate der 4,4'Biss-triazinylamino-stilben^^-disulfonsäure, Verfahren zu ihrer Herstellung und Verwendung ab optische Aufhellungsmittel - Google Patents
Kationische Derivate der 4,4'Biss-triazinylamino-stilben^^-disulfonsäure, Verfahren zu ihrer Herstellung und Verwendung ab optische AufhellungsmittelInfo
- Publication number
- DE1930307C3 DE1930307C3 DE1930307A DE1930307A DE1930307C3 DE 1930307 C3 DE1930307 C3 DE 1930307C3 DE 1930307 A DE1930307 A DE 1930307A DE 1930307 A DE1930307 A DE 1930307A DE 1930307 C3 DE1930307 C3 DE 1930307C3
- Authority
- DE
- Germany
- Prior art keywords
- parts
- weight
- solution
- compound
- volume
- 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
- 239000002253 acid Substances 0.000 title claims description 15
- 239000003795 chemical substances by application Substances 0.000 title claims description 9
- 238000005282 brightening Methods 0.000 title claims description 7
- 230000003287 optical effect Effects 0.000 title claims description 6
- 125000002091 cationic group Chemical group 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 4
- 238000000034 method Methods 0.000 title description 2
- 206010004966 Bite Diseases 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims description 78
- 150000001875 compounds Chemical class 0.000 claims description 68
- -1 2-hydroxypropylene, phenylene Chemical group 0.000 claims description 22
- 239000007795 chemical reaction product Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000001450 anions Chemical class 0.000 claims description 6
- 150000004985 diamines Chemical class 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 3
- 239000007859 condensation product Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- REJHVSOVQBJEBF-OWOJBTEDSA-N 5-azaniumyl-2-[(e)-2-(4-azaniumyl-2-sulfonatophenyl)ethenyl]benzenesulfonate Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1\C=C\C1=CC=C(N)C=C1S(O)(=O)=O REJHVSOVQBJEBF-OWOJBTEDSA-N 0.000 claims 1
- REJHVSOVQBJEBF-UHFFFAOYSA-N DSD-acid Natural products OS(=O)(=O)C1=CC(N)=CC=C1C=CC1=CC=C(N)C=C1S(O)(=O)=O REJHVSOVQBJEBF-UHFFFAOYSA-N 0.000 claims 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000005628 tolylene group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 86
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 62
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
- 239000000460 chlorine Substances 0.000 description 42
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 19
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 19
- 235000011121 sodium hydroxide Nutrition 0.000 description 19
- 239000000203 mixture Substances 0.000 description 18
- 238000003756 stirring Methods 0.000 description 17
- 239000004744 fabric Substances 0.000 description 16
- 159000000000 sodium salts Chemical class 0.000 description 16
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 15
- 239000000725 suspension Substances 0.000 description 14
- 229910052801 chlorine Inorganic materials 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 239000011780 sodium chloride Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 239000002168 alkylating agent Substances 0.000 description 7
- 229940100198 alkylating agent Drugs 0.000 description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 230000002087 whitening effect Effects 0.000 description 6
- NSMMFSKPGXCMOE-UHFFFAOYSA-N 2-[2-(2-sulfophenyl)ethenyl]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C=CC1=CC=CC=C1S(O)(=O)=O NSMMFSKPGXCMOE-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 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 4
- 229920000742 Cotton Polymers 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000010414 supernatant solution Substances 0.000 description 4
- 238000004383 yellowing Methods 0.000 description 4
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229920003043 Cellulose fiber Polymers 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
- 229940073608 benzyl chloride Drugs 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
- HHSBHVJQXZLIRW-UHFFFAOYSA-N 3-n,3-n-dimethylbenzene-1,3-diamine Chemical compound CN(C)C1=CC=CC(N)=C1 HHSBHVJQXZLIRW-UHFFFAOYSA-N 0.000 description 2
- 101150065749 Churc1 gene Proteins 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 2
- 241000218657 Picea Species 0.000 description 2
- 102100038239 Protein Churchill Human genes 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- 235000021240 caseins Nutrition 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000002979 fabric softener Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 2
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- RSAVZMLVLNTTOW-UHFFFAOYSA-N 1-n,1-n,4-trimethylbenzene-1,3-diamine Chemical compound CN(C)C1=CC=C(C)C(N)=C1 RSAVZMLVLNTTOW-UHFFFAOYSA-N 0.000 description 1
- WDWLSTJFJPKYAV-UHFFFAOYSA-N 1-n,1-n-dibutyl-4-n-ethylpentane-1,4-diamine Chemical compound CCCCN(CCCC)CCCC(C)NCC WDWLSTJFJPKYAV-UHFFFAOYSA-N 0.000 description 1
- MKMCBDUEBALBFG-UHFFFAOYSA-N 1-n,1-n-diethyl-4-n-methylpentane-1,4-diamine Chemical compound CCN(CC)CCCC(C)NC MKMCBDUEBALBFG-UHFFFAOYSA-N 0.000 description 1
- SDIOBNKHLKIWOP-UHFFFAOYSA-N 2,2-diethylpropane-1,3-diamine Chemical compound CCC(CC)(CN)CN SDIOBNKHLKIWOP-UHFFFAOYSA-N 0.000 description 1
- KRMMOHWZHDVMBQ-UHFFFAOYSA-N 2-[2-[2-sulfo-4-(1,3,5-triazin-2-ylamino)phenyl]ethenyl]-5-(1,3,5-triazin-2-ylamino)benzenesulfonic acid Chemical class C=1C=C(C=CC=2C(=CC(NC=3N=CN=CN=3)=CC=2)S(O)(=O)=O)C(S(=O)(=O)O)=CC=1NC1=NC=NC=N1 KRMMOHWZHDVMBQ-UHFFFAOYSA-N 0.000 description 1
- SKJLIATVTKHMNL-UHFFFAOYSA-N 2-methoxyethyl n,n-bis(hydroxymethyl)carbamate Chemical compound COCCOC(=O)N(CO)CO SKJLIATVTKHMNL-UHFFFAOYSA-N 0.000 description 1
- HJXIRCMNJLIHQR-UHFFFAOYSA-N 2-n,2-n-dimethylbenzene-1,2-diamine Chemical compound CN(C)C1=CC=CC=C1N HJXIRCMNJLIHQR-UHFFFAOYSA-N 0.000 description 1
- BZFRCCRHMACPGO-UHFFFAOYSA-N 3-n,3-n,4-trimethylbenzene-1,3-diamine Chemical compound CN(C)C1=CC(N)=CC=C1C BZFRCCRHMACPGO-UHFFFAOYSA-N 0.000 description 1
- IOUFMOLZROGOAW-UHFFFAOYSA-N 3-n,3-n-diethyl-4-methylbenzene-1,3-diamine Chemical compound CCN(CC)C1=CC(N)=CC=C1C IOUFMOLZROGOAW-UHFFFAOYSA-N 0.000 description 1
- KFSNHOUZAIGMAF-UHFFFAOYSA-N 3-n,3-n-diethylbenzene-1,3-diamine Chemical compound CCN(CC)C1=CC=CC(N)=C1 KFSNHOUZAIGMAF-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000294754 Macroptilium atropurpureum Species 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 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 1
- 239000003610 charcoal Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000004664 distearyldimethylammonium chloride (DHTDMAC) Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- DNDUSOASNMMTNN-UHFFFAOYSA-N heptane-1,3-diamine Chemical compound CCCCC(N)CCN DNDUSOASNMMTNN-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- ZEFFDINQSBHDSD-UHFFFAOYSA-N n',n'-dibutyl-n-ethylbutane-1,4-diamine Chemical compound CCCCN(CCCC)CCCCNCC ZEFFDINQSBHDSD-UHFFFAOYSA-N 0.000 description 1
- LDIPAUVCWRHLAM-UHFFFAOYSA-N n',n'-dibutylbutane-1,4-diamine Chemical compound CCCCN(CCCC)CCCCN LDIPAUVCWRHLAM-UHFFFAOYSA-N 0.000 description 1
- KYCGURZGBKFEQB-UHFFFAOYSA-N n',n'-dibutylpropane-1,3-diamine Chemical compound CCCCN(CCCC)CCCN KYCGURZGBKFEQB-UHFFFAOYSA-N 0.000 description 1
- JSMPEGRPXGJWRD-UHFFFAOYSA-N n',n'-diethyl-n-methylbutane-1,4-diamine Chemical compound CCN(CC)CCCCNC JSMPEGRPXGJWRD-UHFFFAOYSA-N 0.000 description 1
- MKDYQLJYEBWUIG-UHFFFAOYSA-N n',n'-diethyl-n-methylethane-1,2-diamine Chemical compound CCN(CC)CCNC MKDYQLJYEBWUIG-UHFFFAOYSA-N 0.000 description 1
- SMJVVYQWUFKTKZ-UHFFFAOYSA-N n',n'-diethyl-n-methylpropane-1,3-diamine Chemical compound CCN(CC)CCCNC SMJVVYQWUFKTKZ-UHFFFAOYSA-N 0.000 description 1
- DFTJKKXEHWFFAB-UHFFFAOYSA-N n',n'-diethyl-n-propylpropane-1,3-diamine Chemical compound CCCNCCCN(CC)CC DFTJKKXEHWFFAB-UHFFFAOYSA-N 0.000 description 1
- JILXUIANNUALRZ-UHFFFAOYSA-N n',n'-diethylbutane-1,4-diamine Chemical compound CCN(CC)CCCCN JILXUIANNUALRZ-UHFFFAOYSA-N 0.000 description 1
- ZSGVHFYKNCHHBO-UHFFFAOYSA-N n',n'-dipentylpropane-1,3-diamine Chemical compound CCCCCN(CCCN)CCCCC ZSGVHFYKNCHHBO-UHFFFAOYSA-N 0.000 description 1
- DMDXQHYISPCTGF-UHFFFAOYSA-N n',n'-dipropylethane-1,2-diamine Chemical compound CCCN(CCC)CCN DMDXQHYISPCTGF-UHFFFAOYSA-N 0.000 description 1
- GZUCMODGDIGMBI-UHFFFAOYSA-N n',n'-dipropylpropane-1,3-diamine Chemical compound CCCN(CCC)CCCN GZUCMODGDIGMBI-UHFFFAOYSA-N 0.000 description 1
- VBARFWGILFILHY-UHFFFAOYSA-N n'-benzyl-n'-ethylpropane-1,3-diamine Chemical compound NCCCN(CC)CC1=CC=CC=C1 VBARFWGILFILHY-UHFFFAOYSA-N 0.000 description 1
- SMIQOXAFNYRXHC-UHFFFAOYSA-N n'-butyl-n'-ethylpropane-1,3-diamine Chemical compound CCCCN(CC)CCCN SMIQOXAFNYRXHC-UHFFFAOYSA-N 0.000 description 1
- GOODZUIQBJNDNO-UHFFFAOYSA-N n'-cyclohexyl-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)C1CCCCC1 GOODZUIQBJNDNO-UHFFFAOYSA-N 0.000 description 1
- FRVNYRKFLIOCNF-UHFFFAOYSA-N n'-ethyl-n'-methylpropane-1,3-diamine Chemical compound CCN(C)CCCN FRVNYRKFLIOCNF-UHFFFAOYSA-N 0.000 description 1
- GHGKUGQRRXYXEJ-UHFFFAOYSA-N n'-ethyl-n'-phenylpropane-1,3-diamine Chemical compound NCCCN(CC)C1=CC=CC=C1 GHGKUGQRRXYXEJ-UHFFFAOYSA-N 0.000 description 1
- SMGLLZNMFIPPIT-UHFFFAOYSA-N n'-methyl-n'-propylpropane-1,3-diamine Chemical compound CCCN(C)CCCN SMGLLZNMFIPPIT-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/68—Triazinylamino stilbenes
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Paper (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1095368A CH525991A (de) | 1968-07-22 | 1968-07-22 | Verfahren zum optischen Aufhellen von Textilmaterialien, insbesondere aus natürlicher oder regenerierter Cellulose |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1930307A1 DE1930307A1 (de) | 1970-02-12 |
| DE1930307B2 DE1930307B2 (de) | 1978-06-15 |
| DE1930307C3 true DE1930307C3 (de) | 1979-03-15 |
Family
ID=4368547
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1930307A Expired DE1930307C3 (de) | 1968-07-22 | 1969-06-14 | Kationische Derivate der 4,4'Biss-triazinylamino-stilben^^-disulfonsäure, Verfahren zu ihrer Herstellung und Verwendung ab optische Aufhellungsmittel |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3663538A (forum.php) |
| AT (1) | AT294751B (forum.php) |
| BE (1) | BE736364A (forum.php) |
| CH (3) | CH534170A (forum.php) |
| DE (1) | DE1930307C3 (forum.php) |
| DK (1) | DK137755B (forum.php) |
| FR (1) | FR2013466A1 (forum.php) |
| GB (1) | GB1274545A (forum.php) |
| NL (1) | NL6911208A (forum.php) |
| NO (1) | NO125051B (forum.php) |
| SE (1) | SE346539B (forum.php) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4012378A (en) * | 1972-02-11 | 1977-03-15 | Imperial Chemical Industries Limited | Reactive dyestuffs |
| GB1441109A (en) * | 1973-01-23 | 1976-06-30 | Ici Ltd | Coating compositions |
| CH597204A5 (forum.php) * | 1973-02-16 | 1978-03-31 | Sandoz Ag | |
| CH603878B5 (forum.php) * | 1973-09-21 | 1978-08-31 | Hoechst Ag | |
| DE2915323A1 (de) * | 1978-04-26 | 1979-11-08 | Sandoz Ag | Basische bzw. kationische, sulfonsaeuregruppenhaltige monoazo- oder disazoverbindungen |
| ATE4600T1 (de) * | 1979-09-21 | 1983-09-15 | The Procter & Gamble Company | Wasch- und weichmittelzusammensetzungen und verfahren zu ihrer herstellung. |
| DE3260229D1 (en) * | 1981-02-26 | 1984-07-19 | Ciba Geigy Ag | Amphoteric styrene derivatives |
| JP3220285B2 (ja) | 1993-05-18 | 2001-10-22 | 富士写真フイルム株式会社 | ジアミノスチルベン系化合物及びそれを用いた画像形成方法 |
| GB9626851D0 (en) * | 1996-12-24 | 1997-02-12 | Ciba Geigy Ag | Compounds |
| GB9930247D0 (en) * | 1999-12-22 | 2000-02-09 | Clariant Int Ltd | Improvements in or relating to organic compounds |
| GB9930177D0 (en) * | 1999-12-22 | 2000-02-09 | Clariant Int Ltd | Improvements in or relating to organic compounds |
| EP1485361A1 (en) * | 2002-03-19 | 2004-12-15 | Ciba SC Holding AG | Amphoteric and cationic fluorescent whitening agents |
| EP1656356A1 (en) * | 2003-08-21 | 2006-05-17 | Ciba SC Holding AG | Optical brighteners |
| RU2413719C2 (ru) * | 2008-11-28 | 2011-03-10 | Альбина Ивановна Леонтьева | Способ получения белофора кд-2 |
| WO2011146604A2 (en) * | 2010-05-18 | 2011-11-24 | Milliken & Company | Optical brighteners and compositions comprising the same |
| EP3020768B1 (en) | 2010-05-18 | 2018-04-25 | Milliken & Company | Optical brighteners and compositions comprising the same |
| USD840116S1 (en) | 2017-04-19 | 2019-02-05 | Gramercy Products, Inc. | Ball toy |
-
1968
- 1968-07-22 CH CH631672A patent/CH534170A/de not_active IP Right Cessation
- 1968-07-22 CH CH1095368A patent/CH525991A/de not_active IP Right Cessation
- 1968-07-22 CH CH1095368D patent/CH1095368A4/xx unknown
-
1969
- 1969-06-14 DE DE1930307A patent/DE1930307C3/de not_active Expired
- 1969-07-07 US US839640A patent/US3663538A/en not_active Expired - Lifetime
- 1969-07-15 NO NO2955/69A patent/NO125051B/no unknown
- 1969-07-16 GB GB35888/69A patent/GB1274545A/en not_active Expired
- 1969-07-21 DK DK392469AA patent/DK137755B/da unknown
- 1969-07-21 AT AT698769A patent/AT294751B/de not_active IP Right Cessation
- 1969-07-21 SE SE10243/69A patent/SE346539B/xx unknown
- 1969-07-22 FR FR6924879A patent/FR2013466A1/fr not_active Withdrawn
- 1969-07-22 NL NL6911208A patent/NL6911208A/xx unknown
- 1969-07-22 BE BE736364D patent/BE736364A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE346539B (forum.php) | 1972-07-10 |
| GB1274545A (en) | 1972-05-17 |
| US3663538A (en) | 1972-05-16 |
| NL6911208A (forum.php) | 1970-01-26 |
| DE1930307B2 (de) | 1978-06-15 |
| NO125051B (forum.php) | 1972-07-10 |
| BE736364A (forum.php) | 1970-01-22 |
| CH525991A (de) | 1972-03-30 |
| CH1095368A4 (forum.php) | 1972-03-30 |
| DE1930307A1 (de) | 1970-02-12 |
| DK137755B (da) | 1978-05-01 |
| DK137755C (forum.php) | 1978-10-09 |
| CH534170A (de) | 1973-02-28 |
| AT294751B (de) | 1971-12-10 |
| FR2013466A1 (forum.php) | 1970-04-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1930307C3 (de) | Kationische Derivate der 4,4'Biss-triazinylamino-stilben^^-disulfonsäure, Verfahren zu ihrer Herstellung und Verwendung ab optische Aufhellungsmittel | |
| DE1794330C3 (forum.php) | ||
| DE69110617T2 (de) | Neue Derivate von Phosphonalkanpolykarboxylsäuren und deren Verwendung. | |
| DE69807397T3 (de) | Triazinylaminostilben Verbindungen | |
| DE2830177C2 (de) | Stärkeätherderivate, Verfahren zu deren Herstellung und deren Verwendung bei der Papierherstellung | |
| EP1355004A1 (de) | Verwendung von Aufhellern zur Herstellung von Streichmassen | |
| EP0036076B1 (de) | Verfahren zur Herstellung von formaldehydfreien Ausrüstungsmitteln für cellulosehaltige Textilien und deren Verwendung | |
| DE4237545A1 (de) | Kupferphthalocyanin-Flüssigformierung | |
| EP0713882B1 (de) | Phosphonomethylierte Chitosane | |
| DD144934A5 (de) | Lagerstabile,konzentrierte waessrige loesungen von sulfogruppenhaltigen optischen aufhellern | |
| DE3807030A1 (de) | Waessriges textilbehandlungsmittel und verfahren zum knitterfestmachen von textilmaterial | |
| EP0026157A2 (de) | Quaternäre Ammoniumsalze aus Diepoxyden und Diaminen, ihre Herstellung und Verwendung | |
| EP1177180B1 (de) | Stilbenaufheller | |
| DE2406883A1 (de) | Stilbenverbindungen | |
| DE2335570A1 (de) | Verfahren zur herstellung von bistriazinylamino-stilben-disulfonsaeuren(2,2'), neue bis-triazinyl-amino-stilbendisulfonsaeuren-(2,2'), sowie deren verwendung als optische aufheller fuer organische materialien | |
| EP0061624B1 (de) | Kationische Farbstoffe und deren Verwendung | |
| DE2301531A1 (de) | 4,4'-diaminostilben-2,2'-disulfonsaeurederivate und ihre verwendung | |
| EP0212553B1 (de) | Verfahren zum Färben von Papier | |
| CH367473A (de) | Verfahren zur Herstellung eines Imprägniermittels zur gleichzeitigen Konservierung und Weichmachung von Textilien | |
| AT402518B (de) | Mit guanidin- oder ethylendiaminsalz flammgehemmte zellulose-materialien, enthaltend einen verfärbungsinhibitor | |
| DE1518383A1 (de) | Fuer die Behandlung von Cellulosematerialien bestimmte Produkte und chemische Praeparate,Verfahren zur Herstellung und Anwendung derselben und mit ihren behandelte Artikel | |
| DE3621410A1 (de) | Verfahren zur nachbehandlung von gefaerbten textilen materialien aus synthetischen polyamiden | |
| EP0831130B1 (de) | Lichtechte Disazofarbstoffe | |
| DE1954742C3 (de) | 4,4'-Bis-(sulfoanilino-triazinylamino)-stilben-2,2'-disulfosäuren | |
| DE3338088C1 (de) | Verfahren zur Neutralleimung von Papier, Karton, Pappe und anderen cellulosehaltigen Materialien |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| EI | Miscellaneous see part 3 | ||
| EHJ | Ceased/non-payment of the annual fee |