DE1794330B2 - Verwendung von bis-s-triazinylaminostilbenverbindungen zum optischen aufhellen von cellulosetextilmaterialien in sauren vernetzungsbaedern - Google Patents
Verwendung von bis-s-triazinylaminostilbenverbindungen zum optischen aufhellen von cellulosetextilmaterialien in sauren vernetzungsbaedernInfo
- Publication number
- DE1794330B2 DE1794330B2 DE19681794330 DE1794330A DE1794330B2 DE 1794330 B2 DE1794330 B2 DE 1794330B2 DE 19681794330 DE19681794330 DE 19681794330 DE 1794330 A DE1794330 A DE 1794330A DE 1794330 B2 DE1794330 B2 DE 1794330B2
- Authority
- DE
- Germany
- Prior art keywords
- bis
- compounds
- acid
- salt
- triazinylaminostilbe
- 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.)
- Granted
Links
- 239000002253 acid Substances 0.000 title description 18
- 229920002678 cellulose Polymers 0.000 title description 9
- 239000001913 cellulose Substances 0.000 title description 9
- 238000004132 cross linking Methods 0.000 title description 7
- 239000004753 textile Substances 0.000 title description 7
- 230000003287 optical effect Effects 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 title description 4
- 239000000463 material Substances 0.000 title 1
- -1 alkali metal salts Chemical class 0.000 description 18
- 150000003839 salts Chemical class 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 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 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000001447 alkali salts Chemical class 0.000 description 4
- 238000005282 brightening Methods 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- QDOPPSQPRXIRRX-UHFFFAOYSA-N 1,2-diphenyl-n,n'-bis(1,3,5-triazin-2-yl)ethene-1,2-diamine Chemical class N=1C=NC=NC=1NC(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)NC1=NC=NC=N1 QDOPPSQPRXIRRX-UHFFFAOYSA-N 0.000 description 2
- VGRFLABBLVKUGG-UHFFFAOYSA-N 2-[2-(2-sulfophenyl)-1,2-bis(1,3,5-triazin-2-ylamino)ethenyl]benzenesulfonic acid Polymers OS(=O)(=O)C1=CC=CC=C1C(NC=1N=CN=CN=1)=C(C=1C(=CC=CC=1)S(O)(=O)=O)NC1=NC=NC=N1 VGRFLABBLVKUGG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229910052782 aluminium Chemical class 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229940102253 isopropanolamine Drugs 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000021286 stilbenes Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000004552 water soluble powder Substances 0.000 description 2
- 230000002087 whitening effect Effects 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- LDCCBULMAFILCT-UHFFFAOYSA-N 2-aminobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1S(O)(=O)=O LDCCBULMAFILCT-UHFFFAOYSA-N 0.000 description 1
- BAHMPEMONSMYRQ-UHFFFAOYSA-N 2-aminobenzene-1,4-disulfonic acid;sodium Chemical compound [Na].NC1=CC(S(O)(=O)=O)=CC=C1S(O)(=O)=O BAHMPEMONSMYRQ-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 1
- VALLWWIZOBWSFP-UHFFFAOYSA-N 5-amino-2-[2-(4-amino-2-sulfophenyl)ethenyl]benzenesulfonic acid;sodium Chemical compound [Na].OS(=O)(=O)C1=CC(N)=CC=C1C=CC1=CC=C(N)C=C1S(O)(=O)=O VALLWWIZOBWSFP-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- VHSHFEIAFBKUPN-UHFFFAOYSA-N 6-[2-phenyl-1,2-bis(1,3,5-triazin-2-ylamino)ethenyl]cyclohexa-2,4-diene-1,1-disulfonic acid Polymers N1=C(N=CN=C1)NC(=C(C1C(C=CC=C1)(S(=O)(=O)O)S(=O)(=O)O)NC1=NC=NC=N1)C1=CC=CC=C1 VHSHFEIAFBKUPN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 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 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- HFXDKBNTHIMESS-UHFFFAOYSA-N NC(=O)N.C(O)C(=C(O)CO)C Chemical compound NC(=O)N.C(O)C(=C(O)CO)C HFXDKBNTHIMESS-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- DEKAXZAZRBCFSV-UHFFFAOYSA-N [Na].NC1=CC=C(S(O)(=O)=O)C=C1S(O)(=O)=O Chemical compound [Na].NC1=CC=C(S(O)(=O)=O)C=C1S(O)(=O)=O DEKAXZAZRBCFSV-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical class [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004656 dimethylamines Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical class CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 150000003956 methylamines Chemical class 0.000 description 1
- 150000003941 n-butylamines Chemical class 0.000 description 1
- 125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- INVZMZZUHLNNHA-UHFFFAOYSA-N phenyl(sulfo)sulfamic acid Chemical compound OS(=O)(=O)N(S(O)(=O)=O)C1=CC=CC=C1 INVZMZZUHLNNHA-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/30—Luminescent or fluorescent substances, e.g. for optical bleaching
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65801967A | 1967-08-03 | 1967-08-03 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1794330A1 DE1794330A1 (de) | 1972-03-16 |
| DE1794330B2 true DE1794330B2 (de) | 1973-04-12 |
| DE1794330C3 DE1794330C3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-11-08 |
Family
ID=24639579
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681794330 Granted DE1794330B2 (de) | 1967-08-03 | 1968-08-02 | Verwendung von bis-s-triazinylaminostilbenverbindungen zum optischen aufhellen von cellulosetextilmaterialien in sauren vernetzungsbaedern |
| DE1795047A Expired DE1795047C3 (de) | 1967-08-03 | 1968-08-02 | Bis-s- triazinylamino-stilben-2,2'disulfonsäuren |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1795047A Expired DE1795047C3 (de) | 1967-08-03 | 1968-08-02 | Bis-s- triazinylamino-stilben-2,2'disulfonsäuren |
Country Status (13)
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3542642A (en) * | 1968-03-01 | 1970-11-24 | Geigy Chem Corp | Quenching the fluorescence of optical brightener compounds in paper by means of hydroxymethylamino acetonitrile |
| US3682907A (en) * | 1968-09-12 | 1972-08-08 | Sumitomo Chemical Co | 4,4{40 -bis(2-{62 -sulfoethylamino-4-amino-1,3,5-triazine-6-ylamino)stilbene-2,2{40 -disulfonic |
| US3883515A (en) * | 1969-12-29 | 1975-05-13 | Ciba Geigy Corp | Adiabatic process for the production of 2,4-dichloro-6-amino-S-triazines |
| IT942451B (it) * | 1970-09-16 | 1973-03-20 | Sandoz Ag | Acidi bis traizinilamino stilbensolfonici |
| CH597204A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-02-16 | 1978-03-31 | Sandoz Ag | |
| CH583211A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-05-22 | 1976-12-31 | Sandoz Ag | |
| CH583212A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-07-02 | 1976-12-31 | Sandoz Ag | |
| USRE30227E (en) * | 1973-11-29 | 1980-03-11 | Ciba-Geigy Corporation | Agent for brightening and removing greyness from textiles |
| US4233167A (en) * | 1979-06-14 | 1980-11-11 | S. C. Johnson & Son, Inc. | Liquid detergent softening and brightening composition |
| DE3112435A1 (de) * | 1981-03-28 | 1982-10-07 | Bayer Ag, 5090 Leverkusen | Waessrige aminoplastdispersionen |
| US4597930A (en) * | 1983-07-11 | 1986-07-01 | Szal John R | Method of manufacture of a felted fibrous product from a nonaqueous medium |
| GB8704328D0 (en) * | 1987-02-24 | 1987-04-01 | Sandoz Products Ltd | Organic compounds |
| US4865326A (en) * | 1987-09-24 | 1989-09-12 | Acushnet Company | Optical brightners in golf ball clear coatings |
| US5018742A (en) * | 1987-09-24 | 1991-05-28 | Acushnet Company | Golf ball clear coating with optical brighteners |
| US5160536A (en) * | 1991-04-18 | 1992-11-03 | Acushnet Company | Printing ink for golf balls |
| DE4230656A1 (de) * | 1992-09-14 | 1994-03-17 | Ciba Geigy | Verfahren zur Verbesserung von Weissgrad, Helligkeit und Farbort von Füllstoffen und Pigmenten |
| DE4230655A1 (de) * | 1992-09-14 | 1994-03-17 | Ciba Geigy | Verfahren zur Verbesserung von Weißgrad, Helligkeit und Farbort von Faserstoffen |
| GB9412590D0 (en) * | 1994-06-23 | 1994-08-10 | Sandoz Ltd | Organic compounds |
| DE19500791C1 (de) * | 1995-01-13 | 1996-08-01 | Bayer Ag | Verfahren zur Herstellung von substituierten 4,4'-Diaminostilben-2,2'-disulfonsäuresalzen |
| US5891609A (en) * | 1997-12-15 | 1999-04-06 | Trebla Chemical Company | Photographic color developer replenishing concentrates |
| NL1012168C2 (nl) * | 1999-05-27 | 2000-11-28 | Security Transfer B V | Basispapier, alsmede veiligheidspapier. |
| ES2189619B1 (es) * | 2001-01-30 | 2004-10-01 | Elaboracion De Colorantes, S.A. | 2,2-(vinilenbis(3-sulfonato-4,1-fenilen) imino (6-(bid(2-hidroxipropil) amino) 1,3,5,-triazina-4,2-diil) imino))bis(benceno-1,4-disulfonato) de hexasodio y procedimiento para su obtencion. |
| JP4179584B2 (ja) * | 2001-03-22 | 2008-11-12 | 日本化薬株式会社 | 染色特性に優れる蛍光増白剤の水性液状組成物 |
| WO2005049682A1 (en) * | 2003-11-18 | 2005-06-02 | Ciba Specialty Chemicals Holding Inc. | Fluorescent whiteninig pigments |
| US7638016B2 (en) | 2005-02-19 | 2009-12-29 | International Paper Company | Method for treating kraft pulp with optical brighteners after chlorine bleaching to increase brightness |
| EP1712677A1 (en) * | 2005-04-08 | 2006-10-18 | Clariant International Ltd. | Aqueous solutions of optical brighteners |
| PL209690B1 (pl) * | 2005-11-24 | 2011-10-31 | Termo Organika Społka Z Ograniczoną Odpowiedzialnością | Sposób preparacji tworzyw, zabezpieczający przed działaniem promieniowania ultrafioletowego i ozonu |
| CN101547968A (zh) * | 2006-08-08 | 2009-09-30 | 克莱里安特财务(Bvi)有限公司 | 荧光增白剂的水溶液 |
| ES2387941T7 (es) * | 2008-03-26 | 2018-04-20 | Archroma Ip Gmbh | Composiciones mejoradas de abrillantamiento óptico |
| AU2014259497B2 (en) * | 2008-03-26 | 2016-05-12 | Archroma Ip Gmbh | Improved optical brightening compositions |
| RU2495972C2 (ru) * | 2008-03-26 | 2013-10-20 | Клариант Финанс (Бви) Лимитед | Усовершенствованные композиции для оптического отбеливания |
| US8613834B2 (en) | 2008-04-03 | 2013-12-24 | Basf Se | Paper coating or binding formulations and methods of making and using same |
| PT2370632E (pt) * | 2008-11-27 | 2015-02-09 | Clariant Int Ltd | Composições de branqueamento ótico aperfeiçoadas, para a impressão de alta qualidade por jato de tinta |
| EP2192230B2 (en) † | 2008-11-27 | 2020-01-01 | Clariant Finance (BVI) Limited | Optical brightening compositions for high quality inkjet printing |
| RU2556635C2 (ru) | 2009-12-02 | 2015-07-10 | Клариант Финанс (Бви) Лимитед | Концентрированные стабильные в хранении водные растворы оптических отбеливателей |
| ES2688665T3 (es) * | 2010-07-01 | 2018-11-06 | Archroma Ip Gmbh | Composiciones acuosas para blanqueamiento y matización en aplicaciones de revestimiento |
| JP2013536325A (ja) * | 2010-07-23 | 2013-09-19 | クラリアント・ファイナンス・（ビーブイアイ）・リミテッド | 白色紙の製造方法 |
| JP6068996B2 (ja) * | 2012-02-06 | 2017-01-25 | 日本製紙株式会社 | 顕色剤層にデキストリンを含有する感圧複写紙、および感圧複写紙の製造方法 |
| DE202014000968U1 (de) * | 2014-02-18 | 2014-06-18 | Hans Kölbl | Fügepresse für elektronische Geräte |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE551712A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1955-10-12 | |||
| GB930393A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1959-11-20 | 1900-01-01 | ||
| FR1388476A (fr) * | 1963-04-12 | 1965-02-05 | Gen Aniline & Film Corp | Agents avivants à base d'acide 4, 4'-bis [(4-carboxyméthylamino) et (4-nu-2-sulfoéthylamino)-6-sulfophénoxy-s-triazine-2-ylamino]-2, 2'-stilbène-disulfonique |
-
1967
- 1967-08-03 US US658019A patent/US3479349A/en not_active Expired - Lifetime
-
1968
- 1968-07-10 CH CH1021768D patent/CH1021768A4/xx unknown
- 1968-07-10 CH CH1021768A patent/CH547891A/xx unknown
- 1968-07-30 SE SE10325/68A patent/SE345272B/xx unknown
- 1968-07-30 SE SE13890/70A patent/SE363634B/xx unknown
- 1968-07-30 SE SE13889/70A patent/SE363633B/xx unknown
- 1968-08-02 DE DE19681794330 patent/DE1794330B2/de active Granted
- 1968-08-02 AT AT755668A patent/AT286225B/de not_active IP Right Cessation
- 1968-08-02 ES ES356804A patent/ES356804A1/es not_active Expired
- 1968-08-02 GB GB44885/70A patent/GB1243479A/en not_active Expired
- 1968-08-02 GB GB44884/70A patent/GB1241400A/en not_active Expired
- 1968-08-02 NL NL6811041A patent/NL6811041A/xx unknown
- 1968-08-02 GB GB37026/68A patent/GB1239818A/en not_active Expired
- 1968-08-02 DE DE1795047A patent/DE1795047C3/de not_active Expired
- 1968-08-02 FR FR1576100D patent/FR1576100A/fr not_active Expired
- 1968-08-05 BE BE719065D patent/BE719065A/xx not_active IP Right Cessation
-
1970
- 1970-08-24 SU SU1473678A patent/SU520057A3/ru active
- 1970-10-30 JP JP45095507A patent/JPS5113797B1/ja active Pending
- 1970-10-30 JP JP45095506A patent/JPS5241366B1/ja active Pending
- 1970-11-16 AU AU22277/70A patent/AU426935B2/en not_active Expired
-
1978
- 1978-09-28 NL NL7809830A patent/NL7809830A/xx not_active Application Discontinuation
- 1978-09-28 NL NL7809831A patent/NL7809831A/xx not_active Application Discontinuation
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| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |