US3416945A - Process for the optical brightening of fibers containing terephthalic acid polyesters - Google Patents

Process for the optical brightening of fibers containing terephthalic acid polyesters Download PDF

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Publication number
US3416945A
US3416945A US45844865A US3416945A US 3416945 A US3416945 A US 3416945A US 45844865 A US45844865 A US 45844865A US 3416945 A US3416945 A US 3416945A
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Prior art keywords
fabric
brightening
brightener
formula
terephthalic acid
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English (en)
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Zweidler Reinhard
Keller Max
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Novartis Corp
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Geigy Chemical Corp
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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06LDRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/60Optical bleaching or brightening
    • D06L4/614Optical bleaching or brightening in aqueous solvents
    • D06L4/636Optical bleaching or brightening in aqueous solvents with disperse brighteners
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06LDRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/60Optical bleaching or brightening
    • D06L4/65Optical bleaching or brightening with mixtures of optical brighteners
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/29Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913Rod, strand, filament or fiber
    • Y10T428/2933Coated or with bond, impregnation or core
    • Y10T428/2964Artificial fiber or filament
    • Y10T428/2967Synthetic resin or polymer
    • Y10T428/2969Polyamide, polyimide or polyester
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/29Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913Rod, strand, filament or fiber
    • Y10T428/2933Coated or with bond, impregnation or core
    • Y10T428/2971Impregnation
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2582Coating or impregnation contains an optical bleach or brightener or functions as an optical bleach or brightener [e.g., it masks fabric yellowing, etc.]
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2861Coated or impregnated synthetic organic fiber fabric

Definitions

  • ABSTRACT OF THE DISCLOSURE 15 An improved pad dyeing process for the optical brightening of terephthalic acid polyster fibers is disclosed.
  • the process comprises impregnating the fiber at room temperature with either 214'"-chlorinc-2"-cyanostilbyl-4" (naphtho-l',2':4,5) l,2.3-triazole alone or in a weight ratio of 1:5 to 2:1 with at least One other brightener compound which t'orms colorless blue fluorescent solutions and contains no stilbene groups and has at least one hetero atom fused with a benezene ring selected from coumarin, benzoxazole or naphthalic acid amides.
  • the fiber is squeezed out and heated at preferably 180-220 C. to achieve a white to reddishwhite whiter-white effect.
  • the present invention concerns a process for the optical brightening of fibers containing terephthalic acid polyesters as well as, as industrial product, the fiber materials brightened according to the invention.
  • polyester fibers especially of the Dacron type with optical brightencrs of the oxazole and the like types by methods corresponding to those of the well-known pad-dyeing process, i.e, by impregnation of the goods on a pad mangle (foularding) at room temperature (about 15 to 40 C.), removal of an excess of the impregnating liquor and sub sequent drying and developing by exposure to a higher temperature, in the range of 140 to 220 C., for a short time, up to about one minute.
  • the aqueous brightening dispersion to be used as pad liquor according to the invention contains about 0.5 to 6 g. per liter of finely distributed brightener of Formula I.
  • the particle size of the brightener in the dispersion should be about 1 to 5;!- or even less.
  • the fine degree of distribution of the brightener is attained by the usual methods, advantageously by milling with sand and in the presence of water and a dispersing agent, e.g., a condensation product of naphthalene sulfonic acid and formaldehyde.
  • the amount of'the dispersing agent is about ,4, to 1/ calculated on the weight of the brightener used.
  • the dispersion advantageously contains dispersing or emulsifying agents, e.g., fatty alcohol polyglycol ethers such as stearyl alcohol polyglycol ethers having 8 to 10 ethyleneoxy groups, or it contains protective colloids such as higher polymeric polyacrylates or polyacrylamides such as the commercial product Separan AP (sold by Dow Chemical) or Irgamin E (sold by Geigy, Basel, Switzerland), also thickeners such as alginates or cellulose derivatives, e.g. carboxyalkyl cellulose derivatives such as carboxymethyl cellulose or alkyl cellulose derivatives such as methyl cellulose.
  • dispersing or emulsifying agents e.g., fatty alcohol polyglycol ethers such as stearyl alcohol polyglycol ethers having 8 to 10 ethyleneoxy groups
  • protective colloids such as higher polymeric polyacrylates or polyacrylamides
  • thickeners such as alginates or cellulose derivatives, e.g. carb
  • fabrics which consist exclusively of polyesters are used as "fibers containing terephthalic acid polyesters," for example, fabrics made of poly-(1,2-ethyleneglycol)-terephthalic acid esters such as the commercial products Dacron (E. I. du Pont de Nemours, Wilmington, Del.), Terylene (Imperial Chemical Industries Ltd., London, England), Trevira (Farbwerke Hoechst A.G., Frankfurt am Main, Germany), Diolen (Ve occidentale Glanzstolf AG., Wuppertal, Germany) or Tergal (Rhodiaceta, Lyons, France), but also fabrics made of poly-(1,4-cyclohexyleneglycol)-terephthalic acid esters, e.g., the commercial product Kodel (Tennessee Eastman, Kingsport, Tenn.) are used.
  • the polyterephthalic acid part is brightened. If it is desired to brighten the other component as well, then a brightening pad liquor is used which, in addition to the components mentioned above also contains an optical brightener suitable for the brightening of this component of the fabric. If the fabric is of the preferred mixture of polyterephthalate and cotton, then the cotton part is advantageously optically brightened with a brightener from the class of 4,4-bis-(triazinylamino)-stilbene disulfonic acids, e.g., with one of the brightener: described in U.S. Patent No. 2,473,475.
  • the goods are impregnated with the brightening dispersion by the usual methods, advantageously on a pad mangle.
  • the impregnated material is advantageously squeezed so that its remaining liquor content is from 40 3 to 100%, calculated on the dry weight of the material.
  • the squeezed goods are then, optionally after an intermediate drying, heated to higher temperatures, advantageously with hot air at ISO-220 C.
  • This mixture of brighteners according to the invention consists of the above-mentioned stilbene compound of Formula I and of at least one compound having affinity to polyesters, which compound forms colorless, blue-fluorescent solutions, contains no stilbene groups and contains at least one hetero ring fused with a benzene ring.
  • the mixtures according to the invention cause a surprising, unexpected rise in the strength of the brightening effect.
  • Suitable brighteners containing the coumarin ring are chiefly derivatives of 3-phenyl-7-aminocoumarin; of these the 3-phenyl coumarin compounds substituted in the 7- position by the 3-methyl-pyrazolyl-(l), the naphtho- (1',2':4,S)-triazolyl-(2) or the 4-chloro-6-diethylamino- 1,3,5-triazinyl-(2) radical are particularly suitable.
  • Suitable compounds containing a benzoxazole ring are. e.g., the bis-benzoxazolyl-(2)-ethylenes and -2,5-thiophenes.
  • naphthalic acid imides are 4- alkoxy-naphthalie acid-N-methyl-imide or 4-a'cetamino naphthalic acid-N-butyl-imide.
  • the weight ratio of the brightener of Formula 1 to the other components as defined is advantageously from about 1:5 to 2:1, preferably up about 1:1.
  • the particle size of the brightener should be about 1 to 5;. or even less.
  • the necessary degree of distribution of the brightener is attained by the usual methods described hcreinbct'ore.
  • the aqueous suspension of the active substances to be used as pad liquor in this aspect of the invention preferably contains 0.3 to 5 g. per liter of the brightening mixture and also, advantageously, emulsifying agents, such as the known commercial products- 4 Separan AP or Irgamin E. as well as thickeners, all mentioned in the foregoing.
  • the goods are impregnated with the brightening suspension on a pad mangle and further treated in the manner described hereinbefore.
  • Fibers containing polyesters of terephthalic acid brightcned according to the invention show a similar greatly improved white appearance in daylight and this white shade has similar good fastness to light as the brightened polyester materials obtained by the treatment described under the first aspect of this invention.
  • Example 1 A white ethyleneglycol terephthalate polyester fabric (Dacron) is impregnated on a pad mangle at 25 C. with a ad liquor containing 2 g. of the brightening agent of Formula I in 1000 ml. of water. The fabric is squeezed to leave a liquor content of (calculated on the fiber dry weight) thereon given an intermediate drying at in a hot air stream, and then developed by pasing it for 30 seconds through a heat chamber at 210-220". The fabric so treated shows a very strong, brilliant white effeet.
  • the pad liquor used is produced as follows: 30 parts of thcbrightener, with the addition of 2 parts of sodium methylene-bis-(naphthalene sulfonate) (commercially available under the trade name of Belloid TD) as dispersant, in parts of water are milled with sand until a particle size of at most 5; to smaller than 1;!- is attained. Water and parts of a thickenerconsisting of a stearyl alcohol polyglycol ether having about 9 ethyleneoxy groups are added to this 30% paste and the whole is diluted to 1000 parts so that a 10% paste is obtained. 20 parts of this 10% paste are then diluted with water to 1000 parts and the suspension obtained is used for the processing in the foulard described in the above example.
  • Example 2 A blended fabric consisting of 67% polyethylene glycol terephthalate and 33% cotton, which has been previously bleached with hydrogen peroxide, is impregnated at 25 in a foulard with a suspension obtained analogously to Example 1 which contains 2 g. of the brightener of Formula I and 0.5 g. of the brightener of the formula 3, 1 in 1000 ml. of water. The fabric is squeezed to a liquor content of 60% calculated on the dry fabric weight, given an intermediate drying at 60 and then developed for 2% minutes at 180. The fabric thus treated shows a very strong, brilliant white effect in daylight.
  • Example 4 An unbleached mixed fabric consisting of 65% polyethylene glycol terephthalate and 35% cotton is impregnated at 20 on a pad mangle with a suspension produced according to Example 1 containing 1.5 g. of the brightening agent of Formula I in 1000 ml. of water. The fabric is then wrung out to a liquor content of 50% based on the dry fabric weight and passed through a tentering frame which is so adjusted that the fabric is first pre-dried at 100' and is then heated for 30 seconds at 210'. The fabric thus treated is quite clearly brown colored and, as yet, has no visual white effect. It is then bleached on a covered jigger with an 85 hot aqueous solution which contains 3 m l.
  • Example 6 A mixed fabric made of 67% polyethylene glycol terephthalate and 33% cotton which has been previously bleached with sodium chlorite, is padded at with a pad liquor obtained according to Example 5 which contains 1.2 g. of the brightener of Formula V and 0.8 g. of the brightener of Formula I, in 1000 ml. of water.
  • the fabric is squeezed to a liquor content of about 60% 0f the dry fabric weight, given an intermediate drying at 60, and then developed for 2 minutes at 180.
  • the resulting fabric has a beautiful, brilliant white effect in daylight, of very good fastness to light.
  • Example 7 A mixed fabric made of 67% polyethylene glycol terephthalate and 33% cotton which has been previously bleached with sodium chlorite 'or hydrogen peroxide, is impregnated at 25' on a 'pa'd mangle with a liquor produced analogously to Example 5, but which contains 1.2 g. of the brightener of Formula V, 0.8 g. of the brightener in 1000 ml. of water. The fabric is then thoroughly rinsed, first with warm and then with cold water and afterwards dried at a temperature of 5fl-80. After this treatment both fibers in the mixed fabric show a strong, brilliant white effect.
  • Example 5 A polyethyleneglycol terephthalate fabric (Dacron) is padded at '25 with a suspension containing 1.2 g. of
  • the brightener of the formula ind 0.8 g. of the brightener of Formula I in 1000 ml. of .vater.
  • the goods are squeezed to a liquor content of 50% on the dry fabric weight, given an intermediate drying at and then developed for 30 seconds at 2l0220.
  • the fabric is given a strong, brilliant white effect which has very good fastness to light.
  • the suspension used is produced as follows: 30 parts of the mixture of brighteners of the weight ratio given above and about 2 parts of sodium methylene bis-(naphthalene sulfonate) in 70 parts of water are milled with sand until a particle size of at most 5 microns to less than 1 micron is attained. To 330 parts of the 30%-paste Example 8 A Dacron fabric is impregnated on a pad mangle at 25' with a liquor produced analogously to Example 5 from 1.2 g. of the brightening agent of the formula CH: CH:
  • the fabric is squeezed to a liquor content of 50% (calculated on the dry fabric weight). given an intermediate drying at 60 and then developed for 30 seconds at 210- 220.
  • the resulting fabric shows a very strong, brilliant white effect in daylight, which has very good fastness to light.
  • Example 9 A Dacron fabric is impregnated on a pad mangle at 25 with a liquor produced analogously to Example and 0.8 g. of the brightener of Formula I in l000'ml. of
  • Example 10 A Dacron fabric is impregnated at on a pad mangle with a liquor produced analogously to Example 5 from L2 g. of the brightener of the formula and 0.8 g. of the brightener of Formula I, in 1000 ml. of water.
  • the fabric is wrung out to leave a liquor content of 50% based on the dry fabric weight, pre-dried at and then developed for 30 seconds at 2l0-220 In daylight, the fabric so treated shows a strong, very lightstable, brilliant white effect.
  • Example l 1 An unbleached blended fabric consisting of polyethylene glycol terephthalate and 35% cotton is impregnated at 20' on a pad mangle with a liquor produced according to Example 1 containing 1.2 g. of the brightener of Formula V and 0.8 g. of the brightener of Formula I in 1000 ml. of water.
  • the fabric is wrung out to leave a liquor content of 50%., calculated on the dry weight of the'fabric, and then passed through a tentering frame which is so adiusted that the fabric is pre-dried at and is afterwards heated for 30 seconds at 210'.
  • the fabric so treated is brown colored and has not yet any visual white effect. It is then bleached on a covered iigger with an aqueous solution, having a temperature of 85', which contains 3 ml. of 30%-hydrogen peroxide, 1 ml. of sodium silicate solution (38 136.), 0.25 g. of sodium hydroxide and 0.06 g. of the brightener of Formula IV in 1000 ml. of water.
  • the fabric is then thoroughly rinsed, first with warm and then with cold water, and dried at a temperature of 50-80. After this treatment, both fibers of the blended fabric show a strong, brilliant white effect.
  • the concentration of the exhaustion bath is the highest one usable with excessive "greening" occurring in the brightened fiber material.
  • a fiber material containing terephthalic acid polyester fibers said fiber having been impregnated with from about 0.2 to 6 grams of the compound defined in claim 1 per kilogram of said fiber material and then having been heated at from 180 to 220' C.
  • naphthalic acid imide compound is 4-alkoxy-naphthalic acid-N-methyl imide.
  • naphthalic acid imide compound is 4-acetamino-naphthalic acid-N-butyl imide.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US45844865 1964-05-29 1965-05-24 Process for the optical brightening of fibers containing terephthalic acid polyesters Expired - Lifetime US3416945A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH706164A CH424701A (de) 1964-05-29 1964-05-29 Verfahren zum optischen Aufhellen von polymere Ester der Terephthalsäure enthaltendem Fasermaterial
CH706064A CH427722A (de) 1964-05-29 1964-05-29 Verfahren zum optischen Aufhellen von Polyester der Terephthalsäure enthaltendem Fasermaterial

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US3416945A true US3416945A (en) 1968-12-17

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US45844865 Expired - Lifetime US3416945A (en) 1964-05-29 1965-05-24 Process for the optical brightening of fibers containing terephthalic acid polyesters
US74711868 Expired - Lifetime US3467600A (en) 1964-05-29 1968-07-24 Combination optical brightener for terephthalic acid polyester fibers

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Application Number Title Priority Date Filing Date
US74711868 Expired - Lifetime US3467600A (en) 1964-05-29 1968-07-24 Combination optical brightener for terephthalic acid polyester fibers

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US (2) US3416945A (xx)
JP (1) JPS5015903B1 (xx)
BE (2) BE664606A (xx)
CH (2) CH427722A (xx)
DE (2) DE1519475B1 (xx)
FR (2) FR1440255A (xx)
GB (2) GB1052355A (xx)
NL (2) NL6506796A (xx)
SE (2) SE328844B (xx)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3900608A (en) * 1971-10-23 1975-08-19 Bayer Ag Preparations of optical brighteners
US5187015A (en) * 1989-02-17 1993-02-16 Minnesota Mining And Manufacturing Company Ice release composition, article and method
US5646207A (en) * 1994-03-14 1997-07-08 Ppg Industries, Inc. Aqueous sizing compositions for glass fibers providing improved whiteness in glass fiber reinforced plastics
US8066140B1 (en) * 2003-02-28 2011-11-29 The Charles Machine Works, Inc. Container door and container door latching and sealing system

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4055565A (en) * 1969-12-30 1977-10-25 Sumitomo Chemical Company, Limited Optical brightening agents of naphthalimide derivatives
US4622775A (en) * 1982-11-30 1986-11-18 Kraft, Inc. Hydroponic plant collars
DE3878550D1 (de) * 1987-11-27 1993-03-25 Ciba Geigy Ag Aufhellerdispersion.
DE3878540D1 (de) * 1987-11-27 1993-03-25 Ciba Geigy Ag Aufhellerdispersion.
CN111926559A (zh) * 2020-08-18 2020-11-13 宁夏峰盛科技有限公司 一种三嗪基香豆素型荧光增白剂及其制备方法

Citations (10)

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Publication number Priority date Publication date Assignee Title
US2945033A (en) * 1957-05-29 1960-07-12 Geigy Ag J R 7-triazinylamino-3-phenyl coumarins
US2972611A (en) * 1961-02-21 Irrttnrpsrumttuiatotvt stttkvnf
US3123617A (en) * 1964-03-03 Xnhxch
US3127416A (en) * 1960-09-26 1964-03-31 Ciba Ltd New chlorinated dicarboxylic acid dichloride and process for its manufacture
US3147253A (en) * 1961-06-17 1964-09-01 Hodogaya Chemical Co Ltd Process for manufacturing alpha, betadi-[aryloxazolyl-(2)]-ethylene
US3181948A (en) * 1958-06-02 1965-05-04 Gevaert Photo Prod Nv Method for optical bleaching of coated papers and resultant product
US3288786A (en) * 1962-09-10 1966-11-29 Gen Aniline & Film Corp Naphthotriazole optical brighteners
US3288801A (en) * 1962-06-07 1966-11-29 Sandoz Ltd Fluorescent 1, 2, 3-triazole derivatives of 3-phenyl-coumparin
US3310564A (en) * 1961-01-21 1967-03-21 Kasai Toshiyasu Novel 4-alkoxy naphthalimides
US3330834A (en) * 1967-07-11 Naphthalimide whitening agents anb method of making same

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE560579A (fr) * 1956-09-06 1960-04-22 Geigy Ag J R Composes triazolyl-stilbeniques fluorescents, leur preparation et leurs applications.
NL242891A (xx) * 1958-09-02
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

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2972611A (en) * 1961-02-21 Irrttnrpsrumttuiatotvt stttkvnf
US3123617A (en) * 1964-03-03 Xnhxch
US3330834A (en) * 1967-07-11 Naphthalimide whitening agents anb method of making same
US2945033A (en) * 1957-05-29 1960-07-12 Geigy Ag J R 7-triazinylamino-3-phenyl coumarins
US3181948A (en) * 1958-06-02 1965-05-04 Gevaert Photo Prod Nv Method for optical bleaching of coated papers and resultant product
US3127416A (en) * 1960-09-26 1964-03-31 Ciba Ltd New chlorinated dicarboxylic acid dichloride and process for its manufacture
US3310564A (en) * 1961-01-21 1967-03-21 Kasai Toshiyasu Novel 4-alkoxy naphthalimides
US3147253A (en) * 1961-06-17 1964-09-01 Hodogaya Chemical Co Ltd Process for manufacturing alpha, betadi-[aryloxazolyl-(2)]-ethylene
US3288801A (en) * 1962-06-07 1966-11-29 Sandoz Ltd Fluorescent 1, 2, 3-triazole derivatives of 3-phenyl-coumparin
US3288786A (en) * 1962-09-10 1966-11-29 Gen Aniline & Film Corp Naphthotriazole optical brighteners

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3900608A (en) * 1971-10-23 1975-08-19 Bayer Ag Preparations of optical brighteners
US5187015A (en) * 1989-02-17 1993-02-16 Minnesota Mining And Manufacturing Company Ice release composition, article and method
US5646207A (en) * 1994-03-14 1997-07-08 Ppg Industries, Inc. Aqueous sizing compositions for glass fibers providing improved whiteness in glass fiber reinforced plastics
US6207737B1 (en) 1994-03-14 2001-03-27 Ppg Industries Ohio, Inc. Glass fiber sizing, sized glass fibers and polyolefin reinforced articles
US8066140B1 (en) * 2003-02-28 2011-11-29 The Charles Machine Works, Inc. Container door and container door latching and sealing system

Also Published As

Publication number Publication date
DE1519476B2 (de) 1973-04-19
DE1519476A1 (de) 1970-12-23
BE664605A (xx) 1965-11-29
CH424701A (de) 1966-08-15
SE329589B (xx) 1970-10-19
SE328844B (xx) 1970-09-28
DE1519476C3 (de) 1973-11-08
FR1440255A (fr) 1966-05-27
JPS5015903B1 (xx) 1975-06-09
FR1440254A (fr) 1966-05-27
DE1519475B1 (de) 1970-05-14
GB1052355A (xx) 1966-12-21
BE664606A (xx) 1965-11-29
NL6506796A (xx) 1965-11-30
GB1051814A (xx) 1966-12-21
NL6506795A (xx) 1965-11-30
CH427722A (de) 1966-09-30
US3467600A (en) 1969-09-16

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