US3132106A - Brightener composition for paper derived from metanilic and sulfanilic acids - Google Patents
Brightener composition for paper derived from metanilic and sulfanilic acids Download PDFInfo
- Publication number
- US3132106A US3132106A US159791A US15979161A US3132106A US 3132106 A US3132106 A US 3132106A US 159791 A US159791 A US 159791A US 15979161 A US15979161 A US 15979161A US 3132106 A US3132106 A US 3132106A
- Authority
- US
- United States
- Prior art keywords
- paper
- brightener
- composition
- compound
- parts
- 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 - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims description 41
- 239000002253 acid Substances 0.000 title description 4
- 150000007513 acids Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 229940126062 Compound A Drugs 0.000 description 8
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 8
- 238000005282 brightening Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 229920001131 Pulp (paper) Polymers 0.000 description 6
- TXVWTOBHDDIASC-UHFFFAOYSA-N 1,2-diphenylethene-1,2-diamine Chemical group C=1C=CC=CC=1C(N)=C(N)C1=CC=CC=C1 TXVWTOBHDDIASC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical group NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 3
- 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 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- -1 alkali metal bases Chemical class 0.000 description 3
- 229940037003 alum Drugs 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229950000244 sulfanilic acid Drugs 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000004513 sizing Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- XDVZFVQLRRGUKX-UHFFFAOYSA-N 5,5-diamino-2-[2-(2-sulfophenyl)ethenyl]cyclohexa-1,3-diene-1-sulfonic acid Chemical compound C1=CC(N)(N)CC(S(O)(=O)=O)=C1C=CC1=CC=CC=C1S(O)(=O)=O XDVZFVQLRRGUKX-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
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 101100184147 Caenorhabditis elegans mix-1 gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 101000976697 Homo sapiens Inter-alpha-trypsin inhibitor heavy chain H1 Proteins 0.000 description 1
- 102100023490 Inter-alpha-trypsin inhibitor heavy chain H1 Human genes 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- ANBBXQWFNXMHLD-UHFFFAOYSA-N aluminum;sodium;oxygen(2-) Chemical compound [O-2].[O-2].[Na+].[Al+3] ANBBXQWFNXMHLD-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000018984 mastication Effects 0.000 description 1
- 238000010077 mastication Methods 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 229910001388 sodium aluminate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 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
Definitions
- This invention relates to an improved brightene'r composition; to a process for brightening paper therewith; and to the biightened paper provided.
- a 'Ilhe brightener composition ofthis invention it its acid form is represented by the following:
- V H scan and para-sulfophenyl radicals i.e.,
- composition iii-any event being a mixture oi at I 1east-two of the following three compounds.
- DAS-f TNHOaHqOH Compound C V N HOCzHANH r NIhICzHsOH I NH l mplates acid andneutral salts of the foregoing sulfonic acids with inorganic bases such as alkali metal bases, e.g., sodium, potassium and ammonium hydroxides and carbonates.
- alkali metal bases e.g., sodium, potassium and ammonium hydroxides and carbonates.
- H'eretofore DAS 'triazine brighteners have been used to neutralize the yell-owishtinge of natural or un-- treated paper, thereby giving it :an optically bright, i.e., a'white, appearance.
- DAS brighteners are disadvantageous inespecially one respect, that is, they do not show their normal fullblue fluorescence when applied under acidic conditions such as are encountered conventional paper making processes. This objection applies to a degree, even to the very components which make up the brightening
- the P o p p; during mastication", i.e., in the beater operation, ofiten is as low as 4.2 as a result of the use of precidified pulp, i.e., one in which alumin is added before any of the other ingredients, hr the use of a white water, i.e;, recovered liquor from previous beater operations, as the beater liquor.
- the disadvantage is thus manifested when the brightener is added to paper pulp bet ore it is converted into sheet paper. Moreover, in some cases these brighteners actually cause additional yellowing of the ⁇ paper,the
- the present invention is the DAS triazine brightener composition of the present invention is a superior brightener ior'paper even when a manutacturing operation.
- This composition shows a definite advantage in increased pI-I stability and increased water solubility over other DAS triazine brighteners, even bver the component DAS which make up the brightener conipositioii of this invention. They may thus be "used in relatively high concentrations to treat pulp under low pH conditions without increasing yellowness in the paper pulp; Thus, for example, a-mixture containing equal parts of coinpound A and compound B,described above, is added at paper pulp having a pH of 4.3 during the beater'operation. The resultantpaper when, viewed under ultraviolet light fluoresces much more.
- the brightener composition thereof may be made in any of several alternative ways.
- preformed compound A may be mechanically mixed with preformed compound B in theproper proportions, or alternatively cyanuric' chloride may be reacted with diaminostilbenedisulfonic acid, ethanolamine acids, the last two components being in a ratio of between 1:2 and 2:1. Howsoever prepared, the brightener mixture within the scope of the present invention showsthe aforementioned advantages.
- the brightener of the present invention can be applied in the pulp stage, it is not limited to such application.
- the application step may be combined either with a finishing or sizing operation by incorporating the brightener into the finishing compositions.
- the amount of brightener added to the paper is not highly critical, since the usage depends on the desired degree of brightening. In preferred practice a range of 0.01% to 0.2% based on the weight of the dry paper stock is used, since good brightening isobtained economically.
- Any conventional paper stock may be brightened by the practice of this invention including paper produced from ground wood pulp, sulfite pulp and other pulps or mixtures thereof.
- Example 1 A mixture of 37 parts of 4,4-diaminostilbene-2,2'- disulfonic acid (in the form of its disodium salt) in 360 parts of water with 270 parts of acetone is cooled to about C. A solution containing 36.9 parts of cyanuric chloride in 200 parts of acetone is added rapidly. and after stirring for about 5 minutes, the mixture is neutralized with a 15% aqueous solution of sodium carbonate (gradually over a' 30-minute period). To the gelled condensation mixture is metanilic acid and 17.3 parts of sulfanilic acid. The reaction mixture is heated to 30 C. and then gradually neutralized with sodium carbonate solution (over an overnight period);
- Example 3 v The procedure of Example 1 is followed except that 11.5 parts of metanilic acid and 23.1 parts of sulfanilic acid are used in place of the 17.3 parts of each used therein.
- Example 4 A beater mixture is prepared using 200 parts of dry bleached sulfite pulp in 4,000 ml. water (making a 5.0% consistency pulp), and 30 ml. of 10.0% alum. Then 0.14 part of the brightener composition of Example 1 is added (0.07% concentration on the dry pulp aqueous solution. The batch is stirred for one-half hour and handsheets are formed. The sheets are clear white and fluorescent without any evidence of yellow coloration. V
- Example 5 A white water formulation similar to that encountered in actual manufacturing processes is prepared using 4,000 m1. tap water, 10 ml. of commercial sodium silicate solution, 5 ml. of 4.0% rosin and sufficient 10% alum solution to bring the pH to 5 .5.
- a 5.0% consistency bleached sulfite pulp composition is made up using this white water with 200 parts of dry bleached sulfite pulp and 13 parts of clay. This is stirred 10 minutes and then 70 ml. of 4.0% rosin (pH 7.6) is added. The mixture is stirred an additional 10 minutes, then 0.14 part of the brightener composition of Example 2 is added as a 13.5% solution and the mixture is stirred for another 10 minutes. After adding 68 ml. of 10.0% alum (p11. 4.0), the mixture is stirred for an additional 10 minutes and then, after adjusting the pH to 5.5 using sodium aluminate, sheets are formed. A clear white sheet is obtained, which fluoresces under ultraviolet light or daylight, and shows no yellow tinge.
- Example 6 7 5 at 220 F. for 3 minutes.
- the resulting sheets are con- Example 1 is followed except that and the paper i Q siderably whiter than control sheets similarly coated but a member selected from the group consisting of (a) a mix- 1 ture of at least two of three isomeric compounds rep- 10 resented by the following formula:
- I'claim 1. An aqueous brightener composition consisting essentially of water and at least 0.01 weight percent of a I composition of claim 1.
- R radicals are meta-sulfophenyl and parasulfophenyl, the average occurrence of meta-sulfophenyl 1n the entire composition being between about 0.33 and ITIH IIIH wherein the R radicals are meta-sulfopheny1 and parasulfophenyl, the average'occurrence of meta-sulfophenyl in the entire composition being between about 0.33 and 0.66 per diarninostilbene moiety, and (b) a salt of the compounds recited in (a) wherein the salt-forming cation is a member selected from the group consisting of sodium,
- composition of claim 1 wherein the average occurrence of the meta-sulfophenyl radical is 0.66 per 3.
- the composition of claim 1 wherein the average occurrence of the meta-sulfophenyl radical is 0.5 per diaminosti1bene moiety.
- a process of brightening paper which comprises con- 2,924,549 Klein et al. Feb. 9, 1960 cting said paper with a composition of claim 1. I 45 2,945,762 Carroll et al. July 19, 1960 C 5.
- Aprocess of brightening paper which comprises 0011- 3,012,971 Gessner et al. Dec. 12, 1961 tacting paper pulp with the composition of claim 1. 3,025,242 Seyler Mar. 13,, 1962 tacting sheet paper, during a finishing operation, with the I 9.
- a composition of matter consisting essentially of
Landscapes
- Paper (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL285926D NL285926A (enrdf_load_stackoverflow) | 1961-12-15 | ||
| US159791A US3132106A (en) | 1961-12-15 | 1961-12-15 | Brightener composition for paper derived from metanilic and sulfanilic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US159791A US3132106A (en) | 1961-12-15 | 1961-12-15 | Brightener composition for paper derived from metanilic and sulfanilic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3132106A true US3132106A (en) | 1964-05-05 |
Family
ID=22574034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US159791A Expired - Lifetime US3132106A (en) | 1961-12-15 | 1961-12-15 | Brightener composition for paper derived from metanilic and sulfanilic acids |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3132106A (enrdf_load_stackoverflow) |
| NL (1) | NL285926A (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3366575A (en) * | 1964-03-13 | 1968-01-30 | Nippon Kayaku Kk | Enhancement of optical brightening effects by using two or more species of brightening agent |
| US3533957A (en) * | 1964-05-27 | 1970-10-13 | Geigy Chem Corp | Pyrazoline optical brighteners |
| WO2004005617A1 (en) * | 2002-07-05 | 2004-01-15 | Ciba Specialty Chemicals Holding Inc. | Triazinylaminostilbene disulphonic acid mixtures |
| US20040182533A1 (en) * | 2001-09-03 | 2004-09-23 | Thierry Blum | Method for increasing the whiteness of paper by means of cationic polyelectrolytes |
| EP2239371A1 (en) * | 2009-04-10 | 2010-10-13 | 3V SIGMA S.p.A | Paper coating compositions |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2924549A (en) * | 1955-12-15 | 1960-02-09 | Bayer Ag | Paper containing an organic fluorescent dye |
| US2945762A (en) * | 1955-10-12 | 1960-07-19 | Eastman Kodak Co | Supersensitization of photographic emulsions using triazines |
| US3012971A (en) * | 1959-04-07 | 1961-12-12 | Du Pont | Whitening composition for paper |
| US3025242A (en) * | 1961-03-20 | 1962-03-13 | Du Pont | Whitening agent composition and process for its manufacture |
-
0
- NL NL285926D patent/NL285926A/xx unknown
-
1961
- 1961-12-15 US US159791A patent/US3132106A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2945762A (en) * | 1955-10-12 | 1960-07-19 | Eastman Kodak Co | Supersensitization of photographic emulsions using triazines |
| US2924549A (en) * | 1955-12-15 | 1960-02-09 | Bayer Ag | Paper containing an organic fluorescent dye |
| US3012971A (en) * | 1959-04-07 | 1961-12-12 | Du Pont | Whitening composition for paper |
| US3025242A (en) * | 1961-03-20 | 1962-03-13 | Du Pont | Whitening agent composition and process for its manufacture |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3366575A (en) * | 1964-03-13 | 1968-01-30 | Nippon Kayaku Kk | Enhancement of optical brightening effects by using two or more species of brightening agent |
| US3533957A (en) * | 1964-05-27 | 1970-10-13 | Geigy Chem Corp | Pyrazoline optical brighteners |
| US20040182533A1 (en) * | 2001-09-03 | 2004-09-23 | Thierry Blum | Method for increasing the whiteness of paper by means of cationic polyelectrolytes |
| WO2004005617A1 (en) * | 2002-07-05 | 2004-01-15 | Ciba Specialty Chemicals Holding Inc. | Triazinylaminostilbene disulphonic acid mixtures |
| US20060030707A1 (en) * | 2002-07-05 | 2006-02-09 | Fabienne Cuesta | Triazinylaminostibene disulphonic acid mixtures |
| US7270771B2 (en) | 2002-07-05 | 2007-09-18 | Ciba Specialty Chemicals Corporation | Triazinylaminostilbene disulphonic acid mixtures |
| RU2330870C2 (ru) * | 2002-07-05 | 2008-08-10 | Циба Спешиалти Кемикэлз Холдинг Инк. | Смеси дисульфоновых кислот триазиниламиностильбена |
| KR101016563B1 (ko) | 2002-07-05 | 2011-02-22 | 시바 홀딩 인크 | 트리아지닐아미노스틸벤 디설폰산 혼합물 |
| EP2292837A1 (en) | 2002-07-05 | 2011-03-09 | Basf Se | Triazinylaminostilbene disulphonic acid mixtures |
| EP2239371A1 (en) * | 2009-04-10 | 2010-10-13 | 3V SIGMA S.p.A | Paper coating compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| NL285926A (enrdf_load_stackoverflow) |
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