US2956898A - Certification of correction - Google Patents

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US2956898A
US2956898A US2956898DA US2956898A US 2956898 A US2956898 A US 2956898A US 2956898D A US2956898D A US 2956898DA US 2956898 A US2956898 A US 2956898A
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
    • 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/40—Dyes ; Pigments
    • C11D3/42—Brightening agents ; Blueing agents
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/18—Grafting textile fibers

Definitions

  • the compounds of Formula I are valuable brightening agents for textile fibers, paper and the like and are distinguished from comparable known brightening agents by superior fastness properties, particularly by especially good fastness to light and fastness to washing.
  • the brighteners I of the present invention can be prepared eg by reacting two mols of cyanuric halide (e.g. cyanuric chloride) with one mol of 4,4'-diaminostilbene- 2,2'- disulfonic acid or alkali metal salt thereof and with States Patent Patented Oct. 18, 1960 ice able'to withstand the thermo-fixing process which usually takes place at the end of the finishing treatments. This requisite fastness to temperature is possessed in a very high measure by the compounds I employed according to the present invention.
  • the compounds I contain in the molecule thereof two reactive halogen (chlorine) atoms which can react with water, amines, phenolates, alcoholates and alkalies at temperatures above 60 to 70 to yield new substances of generally enhanced fluorescence but with somewhat slightly lower fastness properties. It was therefore to be assumed that when using these compounds on the fiber, a
  • the brighteners I do not yield a sulficient brightening effect on the polyamide type of fiber, when employed at temperatures between 20 and 50 C. It was therefore most unexpected and surprising that when used at increased temperature between 50 and 100 C., not only was there an enhanced brightening eifect but also-and this, in particular, was wholly unforeseeable a considerable and significant increase in fastness properties, such as fastness to light and fastness to washing, of
  • Illustrative of the radicals Y derived from the aforesaid secondary mono-hydroxyalkylamines are, for example, N-methyl-N-Bhydroxyethylamine, N-ethyl-N-fihydroxyethylarnine, N-isopropyl-N-B-hydroxyethylamine.
  • the action of the brighteners is based upon their capacity to convert invisible ultraviolet light into visible blue to violet fluorescent light.
  • the compounds employed according to the present invention produce especially good brightening effects on polyamide fibers, such as nylon, Perlon, Grilon, wool, silk, etc., but good brightening effects are also realized on cellulose fibers, such as cotton, staple rayon, viscose, paper, etc.
  • the brightening is produced either in an exhausting (or drawing-on) process from a neutral to weakly acid bath, primarily at temperatures between 50 and 100 C. or on the foulard with subsequent heat treatment, eg steaming at 100 to 120 C
  • a neutral to weakly acid bath primarily at temperatures between 50 and 100 C. or on the foulard with subsequent heat treatment, eg steaming at 100 to 120 C
  • the cellulosic fiber use is preferably made of an exhausting process from a neutral to weakly alkaline bath whichcontains a salt, such as Glaubers salt, at temperatures between 20 and 80 C.
  • the brightening according to the present invention may be carried out per se, i.e. as an independent process, or in combination with other processing treatment, such eg as a finishing process, washing, chemical bleaching, softening, etc.
  • the brighteners I are most advantageously employed .7
  • the brightened products be the resultant brightenings.
  • Example 1 25 millig rams per liter of sodium 4,4-bis-(2-(methyl)-5-hydroxyethylamino) 4 chloro-l,3,5-triazyl-(6)- amino)-stilbene-2,2'-disulfonate are added to an aqueous peracetic acid-bleaching bath which contains 2 grams per liter of peracetic acid of 30% strength, after which nylon piece goods are bleached in the said bath in a goods-toliquor ratio of 1:40 by weight for 30 minutes at 70 and for 15 minutes at 80.
  • the nylon which may be undyed nylon filament fabric (polyamide of the sebacic acid-hexamethylenediamine polycondensate type; has a whiter appearance-after being rinsed and driedthan a specimen of the same material similarly treated but in the absence of the brightener.
  • Example 2 Undyed wool skeins, pre-bleached with hydrogen peroxide, are moved about for 20 minutes at in a goodsto-liquor ratio of 1:40 by weight in an aqueous bath which contains 50 milligrams per liter of 4,4-bis-(2-flhydroxydiethylamino 4 chloro 1,3,5 triazyl (6)- amino)-stilbene-2,2'-disulfonic acid and is at a pH of 4 (adjusted with the aid of acetic acid). The material is then rinsed and dried. The wool is distinctly brightened.
  • Example 3 Bleached sulfite cellulose is ground for 20 minutes inthe hollander at a pulp density of 1:40 in the presence of 0.05% of sodium 4,4'-bis-(2-isopropyl-fi-hydroxyethylamino ,4 chloro 1,3,5 triazyl -(6) amino) stilbene-2,2-disulfonate and, after diluting the mass with water to a pulp density of 1:200, it is worked up into Example 4 Nylon piece goods, such as is employed in Example 1, is washed for 20 minutes at 8090 in a goods-to-liquor ratio of 1:20 by weight in an aqueous washing bath which contains, per liter, 1 gram of octylphenyldecagylcolether, lllmilligrams of the brightener employed in Example 1 and 0.1 gram of acetic acid. The washed material is then rinsed and dried. The obtained nylon is of distinctly brightened aspect.
  • the octylphenyldecaglycolether may, with like success, be replaced by any wash-active polyglycolether or by an acid-resistant anion-active washing agent such for example as sodium oleoylmethyltauride.
  • a method of enhancing the white content of organic material which comprises treating the said material with a dilute aqueous solution of a blue-fiuorescing compound of the formula tt t- N N N N $03M M y C G I l N lower lower lower lower lower alkyl fl-hydroxyfl-hydroxyalkyl alkyl alkyl wherein X stands for a halogen atom and M stands for a cation including hydrogen.
  • a method of enhancing the white content of textile fibrous material which comprises treating the said materials with a dilute aqueous solution of a blue-fluorescing compound of the formula wherein X stands for a halogen atom and M stands for a cation including hydrogen.
  • a method of enhancing the white content of a polyamide which comprises treating the said material with a dilute aqueous solution of a blue-fluorescing compound of the formula wherein X stands-for a halogen atom and M stands for a cation including hydrogen.
  • a method of enhancing the white content of cellulose-containing organic material which comprises treating the said material with a dilute aqueous solution of a blue-fluorescing compound of the formula wherein X stands for a halogen atom and M stands for a cation including hydrogen.
  • a method of enhancing the white content of organic material which comprises treating the said material with a dilute aqueous solution of a blue-fluorescing compound of the formula wherein X stands for a halogen atom and M stands for a cation including hydrogen, in a treating bath at a temperature. between 50 and C.
  • a method of enhancing the white content of organic material which comprises treating the said material with a dilute aqueous solution of a blue-fluorescing compound of the formula cation including hydrogen, on the foulard, followed by steaming at a temperature of 100 to C.
  • a method of enhancing the white content of organic material which comprises treating the said material with a dilute aqueous solution of a blue-fluorescing compound of the formula wherein X stands for a halogen atom and M stands for a cation ineluding'lhydrogen, said compound being present in an amount'of about 0.02 to about 0.5% by weight relative to the weight of the material being treated.
  • a method of enhancing the white content of organic material which-1-comprises treating said material with a dilute aqueous solution of sodium 4,4'-bis-2- (methyl-fl-hydroxyethylamino)-4-chloro-1,3,5-triazyl-(6)- amino)-stilbene-2;2'-disulfonate.
  • a method "hi -enhancing the white content of organic material which comprises treating said material with a dilute aqueous solution of 4,4bis-(2-p-hydroxydiethylamino-4-chloro-l,3,5-n-iazyl (6) amino)-stilbene- 2,2'-disulfonic acid.
  • a method of enhancing the white content of organic material which comprises treating said material with a dilute aqueous solution of sodium 4,4'-bis-(2-isopropyl-p-hydroxyethylamino 4 chime-1,3,5 -triazyl-( 6 amino)-stilbene-2,2'-disulfonate.

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  • 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)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

FIP8309 Unite The present invention relates to the improvement of the white conten of organic materials, more especially fibrous materials, such as textile fibers and paper fibers, and products (fabrics, sheets, foils, etc.) made therefrom, and is characterized in that the said materials are treated with a dilute aqueous solution of a blue-fluorescing compound of the formula YC \CNH CH=CH NH(|3/ C-Y I I is N N SOsM SOaM C F 2'( X wherein X stands for a halogen atom, Y stands for the radical of a secondary mono-hydroxyalkylamine which contains 3 to 5 carbon atoms, and M stands for H or an alkali metal cation.
According to the present invention, the compounds of Formula I are valuable brightening agents for textile fibers, paper and the like and are distinguished from comparable known brightening agents by superior fastness properties, particularly by especially good fastness to light and fastness to washing. t The brighteners I of the present invention can be prepared eg by reacting two mols of cyanuric halide (e.g. cyanuric chloride) with one mol of 4,4'-diaminostilbene- 2,2'- disulfonic acid or alkali metal salt thereof and with States Patent Patented Oct. 18, 1960 ice able'to withstand the thermo-fixing process which usually takes place at the end of the finishing treatments. This requisite fastness to temperature is possessed in a very high measure by the compounds I employed according to the present invention.
Another advantage possessed by the brighteners I, in comparison to the comparable prior brighteners, is that they yield more brilliant brightening effects when employed in increasing concentration.
The compounds I contain in the molecule thereof two reactive halogen (chlorine) atoms which can react with water, amines, phenolates, alcoholates and alkalies at temperatures above 60 to 70 to yield new substances of generally enhanced fluorescence but with somewhat slightly lower fastness properties. It was therefore to be assumed that when using these compounds on the fiber, a
temperature of about 50 C. should not be exceeded.
However, the brighteners I do not yield a sulficient brightening effect on the polyamide type of fiber, when employed at temperatures between 20 and 50 C. It was therefore most unexpected and surprising that when used at increased temperature between 50 and 100 C., not only was there an enhanced brightening eifect but also-and this, in particular, was wholly unforeseeable a considerable and significant increase in fastness properties, such as fastness to light and fastness to washing, of
two mols of a mono-hydroxyalkylamine which contains 3.
to 5 carbon atoms.
Illustrative of the radicals Y derived from the aforesaid secondary mono-hydroxyalkylamines are, for example, N-methyl-N-Bhydroxyethylamine, N-ethyl-N-fihydroxyethylarnine, N-isopropyl-N-B-hydroxyethylamine. The action of the brighteners is based upon their capacity to convert invisible ultraviolet light into visible blue to violet fluorescent light.
The compounds employed according to the present invention produce especially good brightening effects on polyamide fibers, such as nylon, Perlon, Grilon, wool, silk, etc., but good brightening effects are also realized on cellulose fibers, such as cotton, staple rayon, viscose, paper, etc.
For the polyamide type of fiber, the brightening is produced either in an exhausting (or drawing-on) process from a neutral to weakly acid bath, primarily at temperatures between 50 and 100 C. or on the foulard with subsequent heat treatment, eg steaming at 100 to 120 C For. the cellulosic fiber, use is preferably made of an exhausting process from a neutral to weakly alkaline bath whichcontains a salt, such as Glaubers salt, at temperatures between 20 and 80 C. I
' p The brightening according to the present invention may be carried out per se, i.e. as an independent process, or in combination with other processing treatment, such eg as a finishing process, washing, chemical bleaching, softening, etc.
The brighteners I are most advantageously employed .7
are especially fast to light and to washing.
In the optical brightening of polyamide fibers, it is particularly important that the brightened products be the resultant brightenings.
This unexpected stability makes it possible to employ the compounds I as white-toners in textile finishing. This represents an important step forward in this field.
The following illustrative examples set forth presentlypreferred exemplary embodiments of the invention. In the said examples, the parts and percentages are by weight. Temperatures are in degrees centigrade.
Example 1 25 millig rams per liter of sodium 4,4-bis-(2-(methyl)-5-hydroxyethylamino) 4 chloro-l,3,5-triazyl-(6)- amino)-stilbene-2,2'-disulfonate are added to an aqueous peracetic acid-bleaching bath which contains 2 grams per liter of peracetic acid of 30% strength, after which nylon piece goods are bleached in the said bath in a goods-toliquor ratio of 1:40 by weight for 30 minutes at 70 and for 15 minutes at 80. The nylon which may be undyed nylon filament fabric (polyamide of the sebacic acid-hexamethylenediamine polycondensate type; has a whiter appearance-after being rinsed and driedthan a specimen of the same material similarly treated but in the absence of the brightener.
The same whitening efiect is obtained if the same material is first treated with the said brightener in the presence of 0.6 gram per liter of aqueous treating bath, and only thereafter treated in the perace-tic acid-bleaching bath of the afore-indicated composition.
Example 2 Undyed wool skeins, pre-bleached with hydrogen peroxide, are moved about for 20 minutes at in a goodsto-liquor ratio of 1:40 by weight in an aqueous bath which contains 50 milligrams per liter of 4,4-bis-(2-flhydroxydiethylamino 4 chloro 1,3,5 triazyl (6)- amino)-stilbene-2,2'-disulfonic acid and is at a pH of 4 (adjusted with the aid of acetic acid). The material is then rinsed and dried. The wool is distinctly brightened.
' Example 3 Bleached sulfite cellulose is ground for 20 minutes inthe hollander at a pulp density of 1:40 in the presence of 0.05% of sodium 4,4'-bis-(2-isopropyl-fi-hydroxyethylamino ,4 chloro 1,3,5 triazyl -(6) amino) stilbene-2,2-disulfonate and, after diluting the mass with water to a pulp density of 1:200, it is worked up into Example 4 Nylon piece goods, such as is employed in Example 1, is washed for 20 minutes at 8090 in a goods-to-liquor ratio of 1:20 by weight in an aqueous washing bath which contains, per liter, 1 gram of octylphenyldecagylcolether, lllmilligrams of the brightener employed in Example 1 and 0.1 gram of acetic acid. The washed material is then rinsed and dried. The obtained nylon is of distinctly brightened aspect.
A similar effect is obtained when, in the preceding paragraph, the brightener of Example 1 is replaced by the same quantity of one of the brightencrs used in Examples 2 and 3.
The octylphenyldecaglycolether may, with like success, be replaced by any wash-active polyglycolether or by an acid-resistant anion-active washing agent such for example as sodium oleoylmethyltauride.
Having thus disclosed the invention What is claimed is:
1. A method of enhancing the white content of organic material, which comprises treating the said material with a dilute aqueous solution of a blue-fiuorescing compound of the formula tt t- N N N N $03M M y C G I l N lower lower lower lower alkyl fl-hydroxyfl-hydroxyalkyl alkyl alkyl wherein X stands for a halogen atom and M stands for a cation including hydrogen.
2. A method of enhancing the white content of textile fibrous material, which comprises treating the said materials with a dilute aqueous solution of a blue-fluorescing compound of the formula wherein X stands for a halogen atom and M stands for a cation including hydrogen.
3. A method of enhancing the white content of paper,
which comprises treating the said material with a dilute aqueous solution of a blue-fiuorescing compound of the formula N N N N $03M $0M 5 t N N lower lower lower lower alkyl B- hydroxy- B-hydroxyalkyl alkyl alkyl wherein X stands for a halogen atom and M stands for a cation including hydrogen.
4. A method of enhancing the white content of a polyamide, which comprises treating the said material with a dilute aqueous solution of a blue-fluorescing compound of the formula wherein X stands-for a halogen atom and M stands for a cation including hydrogen.
5. A method of enhancing the white content of cellulose-containing organic material, which comprises treating the said material with a dilute aqueous solution of a blue-fluorescing compound of the formula wherein X stands for a halogen atom and M stands for a cation including hydrogen.
6-. A method of enhancing the white content of organic material, which comprises treating the said material with a dilute aqueous solution of a blue-fluorescing compound of the formula wherein X stands for a halogen atom and M stands for a cation including hydrogen, in a treating bath at a temperature. between 50 and C.
7. A method of enhancing the white content of organic material, which comprises treating the said material with a dilute aqueous solution of a blue-fluorescing compound of the formula cation including hydrogen, on the foulard, followed by steaming at a temperature of 100 to C.
8. A method of enhancing the white content of organic material, which comprises treating the said material with a dilute aqueous solution of a blue-fluorescing compound of the formula wherein X stands for a halogen atom and M stands for a cation ineluding'lhydrogen, said compound being present in an amount'of about 0.02 to about 0.5% by weight relative to the weight of the material being treated.
9. A method of enhancing the white content of organic material, which-1-comprises treating said material with a dilute aqueous solution of sodium 4,4'-bis-2- (methyl-fl-hydroxyethylamino)-4-chloro-1,3,5-triazyl-(6)- amino)-stilbene-2;2'-disulfonate.
10. A method "hi -enhancing the white content of organic material, which comprises treating said material with a dilute aqueous solution of 4,4bis-(2-p-hydroxydiethylamino-4-chloro-l,3,5-n-iazyl (6) amino)-stilbene- 2,2'-disulfonic acid.
6 11. A method of enhancing the white content of organic material, which comprises treating said material with a dilute aqueous solution of sodium 4,4'-bis-(2-isopropyl-p-hydroxyethylamino 4 chime-1,3,5 -triazyl-( 6 amino)-stilbene-2,2'-disulfonate.
References Cited in the file of this patent UNITED STATES PATENTS 2,778,827 Ackermann Jan. 22, 1957 2,805,999 Ackermann Sept. 10, 1957 FOREIGN PATENTS 528,445 Canada July 31, 1956 715,239 Great Britain Sept. 8, 1954 UNITED STATES PATENT OFFICE CERTIFICATION OF CORRECTION Patent No.0 2,956,898 October 18,
Fritz Fleck It is hereby certified that error appears in the above numbered I ent requiring correction and that the said Letters Patent should read corrected below.
Column 2, line 46, for "polycondensate type; has" rea4 polycondensate type; "Nylon 610"). has
Signed and sealed this 1st day of August 1961,.
(SEAL) Attest:
ERNEST W. SWIDER Attesting Officer DAVID L. LADD Commissioner of Pate:

Claims (1)

1. A METHOD OF ENHANCING THE WHITE CONTENT OF ORGANIC MATERIAL, WHICH COMPRISES TREATING THE SAID MATERIAL WITH A DILUTE AQUEOUS SOLUTION OF A BLUE-FLUORESCING COMPOUND OF THE FORMULA
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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3018287A (en) * 1958-11-05 1962-01-23 Fidelity Union Trust Company Optical brighteners for use with paper
US3113825A (en) * 1961-03-27 1963-12-10 Gen Aniline & Film Corp Dyeing of viscose
US3142531A (en) * 1961-02-08 1964-07-28 Allied Chem Bleaching of gray cotton knit goods
US3157651A (en) * 1964-11-17 Triazine compounds
US3382200A (en) * 1964-05-11 1968-05-07 American Cyanamid Co Composition for treating and brightening cellulose fibers
US3481828A (en) * 1965-03-05 1969-12-02 Hardman & Holden Ltd Bleaching of wood pulp with thiourea dioxide and zinc sulfate
US3869311A (en) * 1969-06-03 1975-03-04 Centre Tech Ind Papier Application of precipitates of methylene-ureas and products obtained
US3907698A (en) * 1973-03-21 1975-09-23 American Cyanamid Co Bridged halotriazine compounds as bleach activators
US3959570A (en) * 1969-06-03 1976-05-25 Centre Technique De L'industrie Des Papiers Cartons Et Celluloses Application of precipitates of methylene ureas and products obtained
US3961880A (en) * 1973-06-29 1976-06-08 Ciba-Geigy Corporation Continuous process for optical brightening and printing of organic textile fiber material
US4105399A (en) * 1973-09-05 1978-08-08 Ciba-Geigy Corporation Optically brightening with a synergistic mixture
US4339238A (en) * 1980-01-14 1982-07-13 Ciba-Geigy Corporation Stable aqueous formulations of stilbene fluorescent whitening agents
US4386965A (en) * 1980-07-03 1983-06-07 Ciba-Geigy Corporation Process for obtaining coating compositions of improved whiteness

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB715239A (en) * 1951-06-26 1954-09-08 Bayer Ag New diaminostilbene compounds
CA528445A (en) * 1956-07-31 Ackermann Franz Derivatives of 4:4'-diaminostilbene-disulfonic acid-(2:2') and process of making same
US2778827A (en) * 1949-10-28 1957-01-22 Ciba Ltd Process for the manufacture of derivatives of 4:4'-diaminostilbene-2:2'-disulfonic acid
US2805999A (en) * 1949-10-18 1957-09-10 Ciba Ltd Detergent compositions containing derivatives of 4:4'-diaminostilbene-disulfonic acid

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA528445A (en) * 1956-07-31 Ackermann Franz Derivatives of 4:4'-diaminostilbene-disulfonic acid-(2:2') and process of making same
US2805999A (en) * 1949-10-18 1957-09-10 Ciba Ltd Detergent compositions containing derivatives of 4:4'-diaminostilbene-disulfonic acid
US2778827A (en) * 1949-10-28 1957-01-22 Ciba Ltd Process for the manufacture of derivatives of 4:4'-diaminostilbene-2:2'-disulfonic acid
GB715239A (en) * 1951-06-26 1954-09-08 Bayer Ag New diaminostilbene compounds

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3157651A (en) * 1964-11-17 Triazine compounds
US3018287A (en) * 1958-11-05 1962-01-23 Fidelity Union Trust Company Optical brighteners for use with paper
US3142531A (en) * 1961-02-08 1964-07-28 Allied Chem Bleaching of gray cotton knit goods
US3113825A (en) * 1961-03-27 1963-12-10 Gen Aniline & Film Corp Dyeing of viscose
US3382200A (en) * 1964-05-11 1968-05-07 American Cyanamid Co Composition for treating and brightening cellulose fibers
US3481828A (en) * 1965-03-05 1969-12-02 Hardman & Holden Ltd Bleaching of wood pulp with thiourea dioxide and zinc sulfate
US3869311A (en) * 1969-06-03 1975-03-04 Centre Tech Ind Papier Application of precipitates of methylene-ureas and products obtained
US3959570A (en) * 1969-06-03 1976-05-25 Centre Technique De L'industrie Des Papiers Cartons Et Celluloses Application of precipitates of methylene ureas and products obtained
US3907698A (en) * 1973-03-21 1975-09-23 American Cyanamid Co Bridged halotriazine compounds as bleach activators
US3961880A (en) * 1973-06-29 1976-06-08 Ciba-Geigy Corporation Continuous process for optical brightening and printing of organic textile fiber material
US4105399A (en) * 1973-09-05 1978-08-08 Ciba-Geigy Corporation Optically brightening with a synergistic mixture
US4339238A (en) * 1980-01-14 1982-07-13 Ciba-Geigy Corporation Stable aqueous formulations of stilbene fluorescent whitening agents
US4386965A (en) * 1980-07-03 1983-06-07 Ciba-Geigy Corporation Process for obtaining coating compositions of improved whiteness

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