EP0309909B1 - Procédé pour l'inalterabilité des teintures de polyester à la lumière en utilisant des éther-esters de benzophénone - Google Patents

Procédé pour l'inalterabilité des teintures de polyester à la lumière en utilisant des éther-esters de benzophénone Download PDF

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Publication number
EP0309909B1
EP0309909B1 EP88115564A EP88115564A EP0309909B1 EP 0309909 B1 EP0309909 B1 EP 0309909B1 EP 88115564 A EP88115564 A EP 88115564A EP 88115564 A EP88115564 A EP 88115564A EP 0309909 B1 EP0309909 B1 EP 0309909B1
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Prior art keywords
acid
formula
benzophenone
polybasic
organic radical
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Expired - Lifetime
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EP88115564A
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German (de)
English (en)
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EP0309909A1 (fr
Inventor
Peter Dr. Neumann
Dieter Dr. Wegerle
Reinhold Krallmann
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BASF SE
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BASF SE
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • D06P3/54—Polyesters using dispersed dyestuffs
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/651—Compounds without nitrogen
    • D06P1/65106—Oxygen-containing compounds
    • 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
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/922—Polyester fiber

Definitions

  • the invention relates to a process for dyeing textile polyester material with disperse dyes using benzophenone ether esters to improve lightfastness, the use of these benzonophenone ether esters in dyeing textile polyester material and new benzophenone ether esters as such.
  • DE-B-1 156 760 discloses a process for improving the lightfastness of polyester dyeings, in which the fibers are placed in a boiling aqueous dyebath which contains, in addition to the dye, alkyl ether of 2,2 ', 4,4'-tetrahydroxybenzophenone contains, treated.
  • the benzophenone derivative is drawn onto the fiber together with the dye.
  • the fiber dyed in this way has better lightfastness when exposed in an exposure device (for example a Xenotest or fadeometer) compared to a fiber dyed without the addition of the tetrahydroxybenzophenone derivative.
  • the compounds described in DE-B-1 156 760 have a number of disadvantages: due to their intrinsic color, they shift the hue in particular in the case of brilliant dyeings and tarnish the coloring to a greater or lesser extent.
  • the absorption capacity on the textile structures is not exhaustive enough, so that the wastewater from the dyeing plants is contaminated with organic compounds.
  • the compounds mentioned tend to sublimation in a thermal aftertreatment usually carried out after the dyeing process.
  • benzophenone ether esters are proposed to improve the light fastness when dyeing textile polyester material. These are optionally substituted 2-hydroxy-4- (2-hydroxyethyl) benzophenone esters, in which the ester residue is derived from a monobasic organic acid.
  • JP-A-60-126 246 discloses 2-hydroxybenzophenone ether esters, in which the acid component of the esters is derived from dicarboxylic acids containing methylidene groups, such as itaconic acid. These connections are expressly excluded from the scope of protection of claims 5 and 6.
  • the 2-hydroxybenzophenone ether esters described are used as comonomers in the copolymerization with other ethylenically unsaturated monomers and as UV absorbers.
  • the object of the invention is to provide materials for the improvement of the light fastness of dyeings with disperse dyes on polyester, which are good for polyester, show a low tendency to sublimation and which do not or only slightly impair the dyeings, in particular with regard to their brilliance.
  • the invention therefore also relates to the new benzophenone derivatives of the formulas III to V in which Y represents a polyvalent organic radical derived from a polybasic heterocyclic acid and R1, R2, m, n and p have the meanings given for formula I, the new benzophenone derivatives of the formula IV in which g is the number 3 or 4 and R1, R2, m and X have the meanings given for formula I, and the new benzophenone derivatives of formula V in which R1, R2, m, n, p and X have the meanings given for formula I, with the proviso that at least one of the radicals R1 and R2 must be different from hydrogen.
  • alkyl radicals for R 1 and R 2 are methyl, ethyl, propyl, n- and tert-butyl.
  • Preferred radicals for R1 are hydrogen, chlorine and methyl, for R2 hydrogen and methyl.
  • polybasic aliphatic, cycloaliphatic or aromatic acids on which the radical X is based are: carbonic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, 3,3-dimethylglutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, maleic acid, fumaric acid, fumaric acid , Itaconic acid (applies exclusively to formulas I and II), citric acid, tricarballyl acid, butane-1,2,3,4-tetracarboxylic acid, ethylenediaminetetraacetic acid, phthalic acid, isophthalic acid, terephthalic acid, hexahydrophthalic acid, hexahydroisophthalic acid, hexahydroterephthalic acid, 3- and 4-phthalic acid, 3- and 4-phthalic acid, m-phenylene diacetic acid, p-phenylene diacetic acid, p
  • Thiophene-2,5-dicarboxylic acid, pyridine-2,6-, pyridine-2,5- and pyridine-3,5-dicarboxylic acid are mentioned as polyvalent organic radicals derived from a polybasic heterocyclic acid or the acids on which these are based. These acid residues correspond in particular to the radical Y in the formula III.
  • the polybasic acids can be expressed as X (COOH) p or Y (COOH) p , where X, Y and p have the meanings given for the formulas I to V.
  • Preferred polybasic acids are succinic acid, glutaric acid, adipic acid, sebacic acid, phthalic acid, isophthalic acid, terephthalic acid, p-phenylenedioxyacetic acid and diphenylene ether dicarboxylic acid.
  • the new compounds of the formula III to V are prepared in a manner known per se by reacting an alcohol of the formula VI in which R1, R2, m and n or g have the meanings given for the formulas III to V, with a polybasic acid X (COOH) p in the case of the preparation of compounds in formulas IV and V or with a polybasic acid Y ( COOH) p in the case of the preparation of compounds of the formula III, where X, Y and p have the meanings given above, in an inert solvent, in particular benzene, toluene or xylene, in the presence of an acidic catalyst, in particular sulfuric acid, p-toluenesulfonic acid or a strongly acidic ion exchanger, at reflux temperatures and working up in a conventional manner.
  • the starting compounds of the formula VI are known or, as in the case of the compounds substituted by radicals R 1 and / or R 2, can be obtained by reacting a corresponding substituted 2,4-dihydroxybenzophenone.
  • the 2-hydroxy-4- (ß-hydroxyethoxy) -4'-chloro and 2-hydroxy-4- (ß-hydroxyethoxyl) -4'-methylbenzophenone by conventional reaction with ethylene oxide or ethylene carbonate from the corresponding 2,4 -Dihydroxy-4'-chloro and 2,4-dihydroxy-4'-methylbenzophenone obtained.
  • textile materials made from polyesters are dyed in a conventional manner.
  • structures such as fibers, threads, flakes, foils, fabrics and knitted fabrics come into consideration as such.
  • the known dye classes such as Azo, anthraquinone, methine, quinophthalone and coumarin dyes belong, according to methods known per se, such as e.g. the high temperature process, the thermosol process or the carrier dyeing process are colored, e.g. can be found in the "Advice, dyeing and finishing of polyester fibers and polyester fiber mixtures", published by BASF Aktiengesellschaft 1974.
  • the benzophenone derivatives are added to the dyebaths in finely divided form, optionally as a powder or liquid preparation. They are used in amounts of 0.1 to 10, preferably 0.3 to 5% by weight, based on the textile material.
  • Benzophenone ether esters to be used particularly preferably in the process according to the invention are the diesters of succinic acid, glutaric acid, adipic acid, phthalic acid, p-phenylenedioxyacetic acid with the 2-hydroxy-4- (2-hydroxyethoxy) benzophenone.
  • 100 parts of a polyester yarn are in a dye bath containing 1500 parts of water, 0.6 parts of a mixture of the finely divided dyes 1.8 parts of a product obtained by adding 50 moles of ethylene oxide to 1 mole of sperm oil alcohol and subsequent sulfonation as a dyeing aid and 1.5 parts of the finely divided benzophenone compound of the formula contains, treats.
  • the process is started at 60 ° C., the temperature is raised to 130 ° C. in 20 minutes and dyeing is carried out for a further 90 minutes at this temperature in an HT dyeing machine.
  • a brown coloration is obtained which, when exposed to xenotest under hot and humid conditions (e.g. temperature 75 ° C, relative air humidity 80%), is significantly more lightfast than the same coloration without the addition of the benzophenone compound.
  • 100 parts of a knitted fabric made of polyester are in a dyebath, the 2500 parts of water, 1.2 parts of a mixture of the finely divided dyes 5 parts of a carrier based on salicylic acid methyl ester and 2 parts of the finely divided benzophenone compound of the formula contains, treats.
  • the dyeing is carried out for 90 minutes at the boiling point and a reddish-brown coloration is obtained which, in an exposure test in a fadeometer, gives significantly better results than a similar coloration without the addition of the benzophenone compound.
  • a polyester fabric is impregnated on a three-roll pad with a dye liquor containing 25 parts of a mixture of the finely divided dyes in 1000 parts
  • the fabric After impregnation with 60% liquor absorption, the fabric is dried at 120 ° C and thermosolated at 200 ° C for 60 seconds.
  • a gray coloration is obtained which is significantly better in light fastness than a same coloration without the addition of the benzophenone compound.
  • a dyeing is carried out analogously to Example 2 using the benzophenone compound of the formula by.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Coloring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Pyridine Compounds (AREA)
  • Polyesters Or Polycarbonates (AREA)

Claims (6)

  1. Procédé de teinture de matières textiles de polyester avec des colorants dispersés, avec utilisation simultanée de dérivés de benzophénone pour améliorer la solidité à la lumière, caractérisé en ce qu'on ajoute, au bain de teinture, au moins un dérivé de benophénone de formule I
    Figure imgb0032
     dans laquelle
    R¹   est mis pour un atome d'hydrogène, un reste alkyle à 1-4 atomes de carbone, un reste cyano, un atome de fluor, de chlore ou de brome ou un groupement trifluorométhyle,
    R²   est mis pour un atome d'hydrogène ou un reste alkyle à 1-6 atomes de carbone,
    m   est mis pour le nombre 1 ou 2,
    n   est mis pour le nombre 2, 3 au 4,
    p   est mis pour le nombre 2, 3 ou 4 et
    X   représente un reste organique polyvalent dérivé d'un polyacide aliphatique, cycloaliphatique, aromatique ou hétérocyclique.
  2. Procédé de teinture de matières textiles de polyester selon la revendication 1, caractérisé en ce qu'on ajoute au bain de teinture un dérive de benzophénone de formule II
    Figure imgb0033
     dans laquelle
    p   représente le nombre 2, 3 ou 4 et
    X   représente un reste organique polyvalent dérivé d'un polyacide aliphatique, cycloaliphatique, aromatique ou hétérocyclique.
  3. Utilisation de dérivés de benzophénone répondant à la formule I définie dans la revendication I dans la teinture de matières textiles de polyester avec des colorants dispersés, afin d'améliorer la solidité à la lumière, dans une proportion de 0,1 à 10% en poids par rapport au produit textile.
  4. Utilisation de dérivés de benzophénone répondant à la formule II définie dans la revendication 2, pour la teinture de matières textiles de polyester avec des colorants dispersés selon la revendication 3.
  5. Dérivés de benzophénone de formules III à V
    Figure imgb0034
     dans laquelle Y est mis pour un reste organique polyvalent dérivé d'un polyacide hétérocyclique, et R¹, R², m, n et p ont les significations indiquées pour la formule I,
    dérivés de benzophénone de formule IV
    Figure imgb0035
     dans laquelle g est mis pour le nombre 3 ou 4 et R¹, R², m et X ont les significations indiquées pour la formule I, à l'exclusion, pour X, de restes organiques polyvalents dérivés de polyacides aliphatiques et contenant des groupements méthylidène,
    dérivés de bensophénone de formule V
    Figure imgb0036
     dans laquelle R¹, R², m, n, p et X ont les significations indiquées pour la formule I, à l'exclusion, pour X, de restes organiques polyvalents dérivés de polyacides aliphatiques et contenant des groupements méthylidène, étant spécifié que l'un au moins des restes R¹ et R² est différent d'un atome d'hydrogène
  6. Procédé de préparation de composés de formules III à V selon la revendication 5, caractérisé en ce qu'on fait réagir un alcool de formule VI
    Figure imgb0037
     dans laquelle R¹, R², m et n ou g ont les significations indiquées pour R¹, R², m, n et g dans les formules III à V, avec un polyacide X(COOH)p dans le cas de la préparation de composés de formules IV et V, ou avec un polyalcool Y(COOH)p dans le cas de la préparation de composés de formule III, X, Y et p ayant les significations indiquées dans la revendication 5, dans un solvant inerte, en particulier dans du benzène, du toluène ou du xylène, en présence d'un catalyseur acide, en particulier d'acide sulfurique, d'acide p-toluènesulfonique ou d'un échangeur d'ions fortement acide, à la température de reflux, et on soumet le produit obtenu à un traitement ultérieur usuel.
EP88115564A 1987-09-30 1988-09-22 Procédé pour l'inalterabilité des teintures de polyester à la lumière en utilisant des éther-esters de benzophénone Expired - Lifetime EP0309909B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19873732980 DE3732980A1 (de) 1987-09-30 1987-09-30 Verfahren zur verbesserung der lichtechtheit von polyesterfaerbungen unter verwendung von benzophenonether-estern und neue benzophenonether-ester
DE3732980 1987-09-30

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EP0309909B1 true EP0309909B1 (fr) 1992-11-25

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US (1) US4911732A (fr)
EP (1) EP0309909B1 (fr)
JP (1) JPH01128956A (fr)
DE (2) DE3732980A1 (fr)

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3930516A1 (de) * 1989-09-13 1991-03-21 Riedel De Haen Ag Benzophenonether-ester, verfahren zu ihrer herstellung, sowie ihre verwendung zur verbesserung der lichtstabilitaet von polyesterfaerbungen
DE4007765A1 (de) * 1990-03-12 1991-09-19 Basf Ag Verwendung von benzophenon-derivaten als lichtschutzmittel fuer aromatische polycarbonate und aromatische polyestercarbonate
US6211383B1 (en) 1993-08-05 2001-04-03 Kimberly-Clark Worldwide, Inc. Nohr-McDonald elimination reaction
US5865471A (en) 1993-08-05 1999-02-02 Kimberly-Clark Worldwide, Inc. Photo-erasable data processing forms
US5645964A (en) 1993-08-05 1997-07-08 Kimberly-Clark Corporation Digital information recording media and method of using same
US5773182A (en) 1993-08-05 1998-06-30 Kimberly-Clark Worldwide, Inc. Method of light stabilizing a colorant
US5733693A (en) 1993-08-05 1998-03-31 Kimberly-Clark Worldwide, Inc. Method for improving the readability of data processing forms
US6017661A (en) 1994-11-09 2000-01-25 Kimberly-Clark Corporation Temporary marking using photoerasable colorants
US6017471A (en) 1993-08-05 2000-01-25 Kimberly-Clark Worldwide, Inc. Colorants and colorant modifiers
US5721287A (en) 1993-08-05 1998-02-24 Kimberly-Clark Worldwide, Inc. Method of mutating a colorant by irradiation
US5681380A (en) 1995-06-05 1997-10-28 Kimberly-Clark Worldwide, Inc. Ink for ink jet printers
US5700850A (en) 1993-08-05 1997-12-23 Kimberly-Clark Worldwide Colorant compositions and colorant stabilizers
US6576797B1 (en) 1994-03-31 2003-06-10 Ciba Specialty Chemicals Corporation Thioether substituted hydroxybenzophenones and stabilized compositions
US6071979A (en) 1994-06-30 2000-06-06 Kimberly-Clark Worldwide, Inc. Photoreactor composition method of generating a reactive species and applications therefor
US5685754A (en) 1994-06-30 1997-11-11 Kimberly-Clark Corporation Method of generating a reactive species and polymer coating applications therefor
US6242057B1 (en) 1994-06-30 2001-06-05 Kimberly-Clark Worldwide, Inc. Photoreactor composition and applications therefor
US6008268A (en) 1994-10-21 1999-12-28 Kimberly-Clark Worldwide, Inc. Photoreactor composition, method of generating a reactive species, and applications therefor
US5786132A (en) 1995-06-05 1998-07-28 Kimberly-Clark Corporation Pre-dyes, mutable dye compositions, and methods of developing a color
AU6378696A (en) 1995-06-05 1996-12-24 Kimberly-Clark Worldwide, Inc. Novel pre-dyes
AU5535296A (en) 1995-06-28 1997-01-30 Kimberly-Clark Worldwide, Inc. Novel colorants and colorant modifiers
US5782963A (en) 1996-03-29 1998-07-21 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
PL321573A1 (en) 1995-11-28 1997-12-08 Kimberly Clark Co Improved stabilising agents for dyes
US5855655A (en) 1996-03-29 1999-01-05 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US6099628A (en) 1996-03-29 2000-08-08 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5891229A (en) 1996-03-29 1999-04-06 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5763674A (en) * 1996-12-09 1998-06-09 General Electric Company High molecular weight dibenzoylresorcinol UV absorbers
US6524379B2 (en) 1997-08-15 2003-02-25 Kimberly-Clark Worldwide, Inc. Colorants, colorant stabilizers, ink compositions, and improved methods of making the same
CA2298615C (fr) 1998-06-03 2009-03-31 Kimberly-Clark Worldwide, Inc. Techniques recourant aux neonanoplastes et aux microemulsions relatives aux encres et a l'impression par jets d'encre
JP2002517523A (ja) 1998-06-03 2002-06-18 キンバリー クラーク ワールドワイド インコーポレイテッド 新規な光開始剤およびその利用
AU5219299A (en) 1998-07-20 2000-02-07 Kimberly-Clark Worldwide, Inc. Improved ink jet ink compositions
PL366326A1 (en) 1998-09-28 2005-01-24 Kimberly-Clark Worldwide, Inc. Novel photoinitiators and applications therefor
EP1144512B1 (fr) 1999-01-19 2003-04-23 Kimberly-Clark Worldwide, Inc. Nouveaux colorants,stabilisateurs de colorants, compositions d'encre, et leur procedes de preparation ameliores
US6331056B1 (en) 1999-02-25 2001-12-18 Kimberly-Clark Worldwide, Inc. Printing apparatus and applications therefor
US6294698B1 (en) 1999-04-16 2001-09-25 Kimberly-Clark Worldwide, Inc. Photoinitiators and applications therefor
US6368395B1 (en) 1999-05-24 2002-04-09 Kimberly-Clark Worldwide, Inc. Subphthalocyanine colorants, ink compositions, and method of making the same
US6537670B1 (en) 2000-11-03 2003-03-25 Cytec Technology Corp. Bis(alkyleneoxybenzophenone) ultraviolet light absorbers
KR100517501B1 (ko) * 2003-03-21 2005-09-28 삼성전자주식회사 내광성 착색제 및 이를 포함하는 내광성 잉크 조성물
KR100532102B1 (ko) * 2003-05-27 2005-11-29 삼성전자주식회사 벤조페논계 화합물 및 이를 포함하는 잉크 조성물

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60126246A (ja) * 1983-12-13 1985-07-05 Mitsubishi Petrochem Co Ltd メチレン二塩基酸誘導体
EP0254987A2 (fr) * 1986-07-26 1988-02-03 BASF Aktiengesellschaft Ethers-esters de la benzophénone et procédé d'amélioration de la stabilité à la lumière de colorations de polyesters par l'utilisation des éthers-esters de la benzophénone

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2920978A (en) * 1958-05-26 1960-01-12 Gen Aniline & Film Corp Stabilized polyester fibres
DE1643307C3 (de) * 1967-12-21 1974-01-17 Ciba-Geigy Marienberg Gmbh, 6141 Lautern 2-Hydroxy-4-(acyloxyäthoxy)benzophenone und Verfahren zu deren Herstellung
US3676471A (en) * 1967-12-21 1972-07-11 Advance Prod Gmbh 4-(betahydroxyethoxy-2-hydroxy-benzophenones) and esters thereof
US3644485A (en) * 1969-04-14 1972-02-22 Eastman Kodak Co 2-hydroxy-4-(2 - hydroxyethoxy) benzophenone esters and their use as stabilizers
GB1553781A (en) * 1976-08-05 1979-10-10 Exxon Research Engineering Co Bisphenol derivatives and their use as stabilizers
DE3438190A1 (de) * 1984-10-18 1986-04-24 Riedel-De Haen Ag, 3016 Seelze Uv-licht-stabilisator auf benzophenon-basis

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60126246A (ja) * 1983-12-13 1985-07-05 Mitsubishi Petrochem Co Ltd メチレン二塩基酸誘導体
EP0254987A2 (fr) * 1986-07-26 1988-02-03 BASF Aktiengesellschaft Ethers-esters de la benzophénone et procédé d'amélioration de la stabilité à la lumière de colorations de polyesters par l'utilisation des éthers-esters de la benzophénone

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JPH01128956A (ja) 1989-05-22
US4911732A (en) 1990-03-27
EP0309909A1 (fr) 1989-04-05
DE3732980A1 (de) 1989-04-13
DE3876204D1 (de) 1993-01-07

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