EP0765415B1 - Agents lissants thermostables pour textiles - Google Patents

Agents lissants thermostables pour textiles Download PDF

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Publication number
EP0765415B1
EP0765415B1 EP95923248A EP95923248A EP0765415B1 EP 0765415 B1 EP0765415 B1 EP 0765415B1 EP 95923248 A EP95923248 A EP 95923248A EP 95923248 A EP95923248 A EP 95923248A EP 0765415 B1 EP0765415 B1 EP 0765415B1
Authority
EP
European Patent Office
Prior art keywords
lubricants
esters
acid
weight
thiocarboxylic
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
Application number
EP95923248A
Other languages
German (de)
English (en)
Other versions
EP0765415A1 (fr
Inventor
Raymond Mathis
Norbert Bialas
F. Norman Tuller
Richard P. Crews
Elbert H. Mudge
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cognis IP Management GmbH
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0765415A1 publication Critical patent/EP0765415A1/fr
Application granted granted Critical
Publication of EP0765415B1 publication Critical patent/EP0765415B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
    • D06M13/248—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing sulfur
    • D06M13/252—Mercaptans, thiophenols, sulfides or polysulfides, e.g. mercapto acetic acid; Sulfonium compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/144—Alcohols; Metal alcoholates
    • D06M13/148—Polyalcohols, e.g. glycerol or glucose
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions

Definitions

  • thermostable textile smoothing agents obtainable by reacting polyols with C 6-22 fatty acids in the presence of small amounts of special esters of thiocarboxylic acids and spin finishes which contain these textile smoothing agents.
  • spin finishes are used used. These spin finishes all contain so-called textile smoothing agent to avoid friction between filaments or fibers and to minimize between filaments and governing bodies.
  • textile Smoothing agents are increasingly being used in esters.
  • thermal Stability thermal stability
  • antioxidants such as butylated hydroxytoluene (BHT) to use because such connections are already in small up to medium quantities effectively improve the thermal stability.
  • BHT butylated hydroxytoluene
  • antioxidants e.g. B. the commercially known Irganox R 1010 known to those skilled in the art, the volatility of which is relatively low.
  • this procedure has the disadvantage that this group of antioxidants has only a limited solubility in the esters. It follows from this that the required concentration of dissolved antioxidant cannot be achieved to a sufficient extent.
  • a method for improving the solubility of antioxidants in smoothing agents is known from WO 91/13134, the antioxidant being incorporated into a carrier medium via covalent bonds.
  • the teaching of WO 91/13134 in its preferred embodiment relates to the fact that so-called "superstable lubricants" are obtained when the proportion of the covalently bound antioxidant in the carrier medium is in the range from greater than 0 to 30% by weight.
  • the proportion of the covalently bound antioxidant in the carrier medium is in each case 10 or 20% by weight.
  • An example of a particularly suitable product is a textile smoothing agent in which 10% by weight of Irganox R 1010 is covalently bonded to pentaerythritol pelargonate as a carrier. From an economic and ecological point of view, however, it is desirable to minimize the antioxidant content.
  • GB-A-454 449 describes the use of certain carboxylic acids or thiocarboxylic acids as a replacement for oleic acid as spinning oil.
  • GB-A-738 749 describes a mixture of water-soluble alkali salt of an organic acid and water-insoluble fatty acid glycol ester or fatty alcohol ether as an additive in spin finishes to improve the emulsion properties.
  • GB-A-930 336 describes esters of polyols and fatty acids in a mixture with other constituents as spinning oils. Thiocarboxylic acid esters are not included.
  • GB-A-499 371 describes the addition of certain sulfur-containing compounds as antioxidants to smoothing agents which contain unsaturated compounds.
  • the object of the present invention was to provide thermostable textile smoothing agents To provide the disadvantages of the known prior art avoid technology.
  • the aim was to create thermostable textiles Developing smoothing agents that contain a minimal amount of antioxidants need.
  • the polyols a) and the fatty acids b) can be saturated or olefinic unsaturated and straight or branched with respect to their carbon skeleton be.
  • the radicals R 1 to R 4 can be saturated or olefinically unsaturated, straight-chain or branched, insofar as this is an alkyl, alkylene, cycloalkylene or cycloalkyl group or the alkyl part of an alkaryl group.
  • Polyols are polyvalent in the context of the present invention Alcohols understood with at least 2 OH groups.
  • the chemical constitution the polyols are not subject to any particular restrictions, i.e. they can be straight or branched.
  • the polyols selected from that of glycerol, trimethylolpropane, neopentyl glycol and pentaerythritol formed group.
  • the fatty acids with 8 to 18 carbon atoms are preferred, which are also preferably saturated.
  • the best effects are achieved in the context of the present invention if fatty acids with 8 to 10 carbon atoms are used as component b).
  • the latter acids are known to those skilled in the art as caprylic acid, pelargonic acid and capric acid. These acids can be used as component b) either individually or in mixtures. Mixtures of C 8 and C 10 fatty acids are known as so-called pre-fatty acids.
  • esters of thiocarboxylic acids are preferred in which the thiocarboxylic acids of the general formula (I) and / or (II) with monofunctional aliphatic alcohols with 1 to 22 C atoms, neopentyl glycol, glycerin, trimethylolpropane or pentaerythritol are esterified.
  • monofunctional aliphatic alcohols with 1 to 22 C atoms
  • neopentyl glycol, glycerin, trimethylolpropane or pentaerythritol are esterified.
  • polyfunctional alcohols neopentyl glycol, glycerin, Trimethylolpropane and pentaerythritol can be pure or else also act as mixed esters.
  • esters are called “pure” esters understood in which all hydroxyl groups of the polyfunctional alcohols with one or more thiocarboxylic acids of the general formula (I) and / or (II) are esterified.
  • “Mixed” esters are such Understood esters in which at least one hydroxyl group with a Thiocarboxylic acid of the general formula (I) or (II) is esterified. The other hydroxyl groups are then with fatty acids with 6 to 22 carbon atoms, as described in connection with component b), esterified.
  • the esters of monofunctional aliphatic are particularly preferred Alcohols of the type described and the "pure” esters of pentaerythritol.
  • the monofunctional aliphatic alcohols are particularly suitable n- and i-butanol, 2-ethylhexanol, isotridecanol, lauryl alcohol, isostearyl alcohol and / or oleyl alcohol.
  • R 1 denotes an alkyl group with 6 to 18 C atoms
  • R 2 denotes an alkylene group with 1 or 2 C atoms.
  • Particularly suitable examples are ⁇ -laurylthiopropionic acid (C 12 H 25 SCH 2 CH 2 COOH) and ⁇ -octylthiopropionic acid (C 8 H 17 SCH 2 CH 2 COOH).
  • R 3 and R 4 are an alkylene group having 2 carbon atoms, ie thiodipropionic acid (HOOCCH 2 CH 2 SCH 2 CH 2 COOH).
  • esters of thiocarboxylic acid are commercially available compounds that but are also easily accessible by known esterification reactions.
  • the mixed esters can easily be obtained by transesterification of the pure thioates obtained with the fatty acids described.
  • esters of thiocarboxylic acids in an amount of 0.05 to 8 % By weight, based on the sum of components a) and b), is used. It is preferred to use the esters of thiocarboxylic acids in an amount of 0.5 to 5 wt .-%, in particular from 1.0 to 3.0 wt .-%, use. This The quantities used relate to the quantities defined above on pure esters of thiocarboxylic acids. With mixed esters of thiocarboxylic acids are in accordance with the content of thiocarboxylic acids in the ester use higher quantities.
  • esters of thiocarboxylic acids can be used in the Implementation between polyols a) and fatty acids b) from the beginning be or be added only during the implementation. Furthermore they can be added in their entirety or in portions will.
  • the reaction between polyols a) and the fatty acids b) takes place under the conditions customary for esterification reactions.
  • the presence the esters of thiocarboxylic acids of the general formula (I) and / or (II) causes an improvement in thermal stability on the one hand and on the other a color improvement of the textile smoothing agents obtained, since these are lighter in color than when manufactured without the presence of those described Esters of thiocarboxylic acids.
  • the invention Agents additionally added antioxidants as additive d).
  • This Antioxidants are added after the reaction of the polyols a) with fatty acids b) added in the presence of the esters of thiocarboxylic acids.
  • antioxidants butylated hydroxytoluene, dialkyl or diarylphosphonates are suitable, Trialkyl or triaryl phosphites, ascorbic or citric acid and their Derivatives and especially sterically hindered phenols.
  • the sterically hindered are particularly preferred as additional additives Phenols of the structure (A-1 and / or A-6) used.
  • the additional additives d) ensure that the inherently good thermal stability of the textile smoothing agents according to the invention is further improved in a synergistic manner. This can be seen, inter alia, from the fact that significantly smaller amounts of the antioxidants d) have to be added than described, for example, in WO 91/13134 (10 to 20% by weight) in order to achieve comparable thermostabilities. For example, even amounts of 1.0% by weight of the sterically hindered Irganox R 1010 phenol - based on components a) to c) - give excellent thermal stability.
  • the antioxidants d) in relation to the esters of thiocarboxylic acids in an amount from 1: 1 to 1: 4.
  • the sterically hindered phenols particularly good results if the amount of additional Antioxidants d) 10 to 50% by weight, based on the esters of thiocarboxylic acids - Is, the range of 20 to 30 wt .-% is particularly preferred is.
  • the textile smoothing agents according to the invention due to their high thermal stability, among other things can be used in spin finishes.
  • Another subject of The present invention is therefore spin finishes for synthetic filaments, characterized in that they have the described thermostable contain textile smoothing agents.
  • the textile smoothing agent in turn may contain the additional antioxidants d).
  • the spin finishes contain at least about 35% by weight of the textile smoothing agents.
  • Other components of the spin finishes can be emulsifiers, wetting agents and / or antistatic agents and those known from the prior art Auxiliaries such as thread closing agents, pH regulators, bactericides and / or anti-corrosion agents.
  • Suitable emulsifiers, wetting agents and / or antistatic agents are anionic, cationic and / or nonionic surfactants, such as mono- and / or diglycerides, for example glycerol mono- and / or glycerol dioleate, alkoxylated, preferably ethoxylated and / or propoxylated fats or oils, fatty alcohols with 8 to 24 carbon atoms and / or C 8-18 alkylphenols, for example addition products of 25 mol ethylene oxide onto castor oil and / or addition products of 8 mol propylene oxide and 6 mol ethylene oxide onto C 16-18 fatty alcohols, if desired alkoxylated C 8- 24 fatty acid mono- and / or diethanolamides, for example - optionally ethoxylated - oleic acid mono- and / or diethanolamide, tallow fatty acid mono- and / or diethanolamide and / or coconut fatty acid mono- and / or
  • alkyl sulfosuccinates for example sodium dioctyl sulfosuccinate and / or amine oxides, for example dimethyldodecylamine oxide.
  • an antistatic can act as an emulsifier at about the same time.
  • Suitable thread closure agents are the polyacrylates, fatty acid sarcosides and / or copolymers with maleic anhydride known from the prior art.
  • Suitable pH regulators are C 1-4 carboxylic acids and / or C 1-4 hydroxycarboxylic acids, e.g. B. acetic acid and / or glycolic acid, alkali hydroxides such as potassium hydroxide and / or amines such as triethanolamide, the presence of bactericides and / or anti-corrosion agents is possible.
  • the spin finishes according to the invention can be mixed intensively the textile smoothing agent according to the invention, optionally with the emulsifiers, Wetting agents, antistatic agents and, if necessary, with the usual additives Produce approx. 18-25 ° C.
  • the thermal stability was determined by means of a bowl test. For this purpose, 3 g of substance were placed in an aluminum dish and exposed to a temperature of 250 ° C. in an oven for 3 hours. Then it was determined how much of the substance (in%) is still present after the thermal treatment. The higher the value, the better.
  • the pure pentaerythritol full ester of pelargonic acid without any addition of antioxidants served as a comparison (comparison). example % Residue comparison 69.8 AA) 76.7 FROM) 96.6 AC) 89.2
  • the application examples show that the textile smoothing agents according to the invention have a higher thermal stability than the pure ester (comparison), despite only minor additions to the thiocarboxylic acid esters. Furthermore shows that the addition of the smallest amounts of the sterically hindered Phenols synergistically improve thermal stability (see AB) and AC)). In addition, when using the invention textile smoothing agent the residues lighter colored and more liquid than comparable ones Esters without the addition of the esters of thiocarboxylic acids.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)

Claims (11)

  1. Agents lissants thermostables pour textiles qu'on peut obtenir par réaction :
    a) de polyols avec
    b) des acides gras ayant de 6 à 22 atomes de carbone en présence de 0,05 à 8 % en poids, par rapport à la somme des composants a) et b) sur
    c) des esters d'acides thiocarboxyliques des formules générales (I) et/ou (II) : R1 - S - R2 - COOH HOOC - R3 - S - R4 - COOH
    dans lesquelles :
    R1 représente un radical monovalent et R2, R3, R4 des radicaux égaux ou différents bivalents d'alcanes, de cycloalcanes, d'aromates ou d'alkylaromates ayant de 1 à 22 atomes de C.
  2. Agents lissants selon la revendication 1,
    caractérisés en ce que
    les polyols sont choisis dans le groupe du néopentylglycol, du glycérol, du triméthylolpropane et du pentaérythritol.
  3. Agents lissants selon les revendications 1 ou 2,
    caractérisés en ce que
    les acides gras comprennent 8 à 10 atomes de carbone et sont de préférence saturés.
  4. Agents lissants selon une des revendications 1 à 3,
    caractérisés en ce que
    les acides gras sont l'acide caprylique, l'acide pélargonique et/ou l'acide caprique.
  5. Agents lissants selon une des revendications 1 à 4,
    caractérisés en ce que
    les acides thiocarboxyliques sont estérifiés par des alcools monofonctionnels ayant de 1 à 22 atomes de C, le glycol néopentylique, le glycérol, le triméthylolpropane ou le pentaérythritol.
  6. Agents lissants selon une des revendications 1 à 5,
    caractérisés en ce que
    dans la formule (I) R1 représente un groupe alkyle ayant de 6 à 18 atomes de C et R2 un groupe alkylène ayant 1 ou 2 atomes de C.
  7. Agents lissants selon une des revendications 1 à 6,
    caractérisés en ce que
    dans la formule (II) R3 et R4 représentent en groupe alkylène ayant 2 atomes de C.
  8. Agents lissants selon une des revendications 1 à 7,
    caractérisés en ce que
    les esters de l'acide thiocarboxylique sont présents en une quantité de 0,5 à 5 % en poids, en particulier de 1 à 3 % en poids, par rapport à la somme des composants a) et b).
  9. Agents lissants selon une des revendications 1 à 8,
    caractérisés en ce qu'
    en supplément des antioxydants, de préférence des phénols empêchés stériquement, sont contenus comme additif d).
  10. Agents lissants selon une des revendications 1 à 9,
    caractérisés en ce que
    les antioxydants sont contenus au prorata des esters des acides thiocarboxyliques dans une quantité de 1:1 à 1:4.
  11. Préparations de filage pour des filaments synthétiques,
    caractérisées en ce qu'
    elles contiennent des agents lissants pour textiles selon la revendication 1.
EP95923248A 1994-06-16 1995-06-07 Agents lissants thermostables pour textiles Expired - Lifetime EP0765415B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US260852 1994-06-16
US08/260,852 US5464546A (en) 1994-06-16 1994-06-16 Thermally stable textile lubricants
PCT/EP1995/002189 WO1995034708A1 (fr) 1994-06-16 1995-06-07 Agents lissants textiles thermostables

Publications (2)

Publication Number Publication Date
EP0765415A1 EP0765415A1 (fr) 1997-04-02
EP0765415B1 true EP0765415B1 (fr) 1998-09-30

Family

ID=22990898

Family Applications (1)

Application Number Title Priority Date Filing Date
EP95923248A Expired - Lifetime EP0765415B1 (fr) 1994-06-16 1995-06-07 Agents lissants thermostables pour textiles

Country Status (5)

Country Link
US (1) US5464546A (fr)
EP (1) EP0765415B1 (fr)
DE (1) DE59503796D1 (fr)
ES (1) ES2121397T3 (fr)
WO (1) WO1995034708A1 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5972497A (en) * 1996-10-09 1999-10-26 Fiberco, Inc. Ester lubricants as hydrophobic fiber finishes
WO1998024559A1 (fr) * 1996-12-05 1998-06-11 Henkel Corporation Thioesters utilises en tant que lubrifiants limites
US6106942A (en) * 1998-12-02 2000-08-22 Celanese Acetate Llc Liquid crystalline polymer monofilaments having improved adhesion characteristics
US7252779B2 (en) * 2000-08-02 2007-08-07 Mj Research Limited Partnership Transesterification composition of fatty acid esters, and uses thereof
CN100341988C (zh) * 2003-04-02 2007-10-10 出光兴产株式会社 导电润滑剂组合物
JP6445205B1 (ja) * 2018-06-28 2018-12-26 竹本油脂株式会社 合成繊維用処理剤及び合成繊維
CN111576046A (zh) * 2020-04-23 2020-08-25 桐乡市恒隆化工有限公司 一种原油上油的纺丝拉伸一步法用油剂及其制备方法
CN113717778B (zh) * 2021-08-23 2022-12-06 江苏悦孚油品有限公司 一种针织大圆机合成油及其制备方法

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB360982A (en) * 1935-02-24 1931-11-16 Ig Farbenindustrie Ag Improvements in or relating to the treatment of textiles
GB497574A (en) * 1937-04-20 1938-12-20 Lister And Company Ltd Improvements in treating textiles and oils therefor
GB738749A (en) * 1952-04-18 1955-10-19 Exxon Research Engineering Co Emulsifiable oleaginous composition
NL262835A (fr) * 1960-03-29
US4066558A (en) * 1974-02-11 1978-01-03 Ici Americas Inc. Low viscosity spin finish systems for neat finish application
US3963628A (en) * 1974-06-07 1976-06-15 Union Carbide Corporation Fiber lubricant composition
US4069160A (en) * 1975-01-20 1978-01-17 Hoechst Fibers Industries, Division Of American Hoechst Corporation Texturing finish for synthetic filaments
US4072617A (en) * 1976-04-12 1978-02-07 Dow Badische Company Finish for acrylic fiber
US4111819A (en) * 1977-11-14 1978-09-05 Shell Oil Company Textile fiber lubricant
US4371658A (en) * 1980-05-05 1983-02-01 Allied Corporation Polyamide yarn spin finish containing a glyceride and oxidized polyethylene
US4400281A (en) * 1981-08-19 1983-08-23 Atlantic Richfield Co. Yarn processing lubricants
DE3402155A1 (de) * 1984-01-23 1985-07-25 Henkel KGaA, 4000 Düsseldorf Spinnpraeparation fuer das schmelzspinnen von synthetischen fasermaterialien
US5155244A (en) * 1990-02-28 1992-10-13 Karlshamns Ab Preparation of antioxidant glyceride derivatives utilizing esterification

Also Published As

Publication number Publication date
WO1995034708A1 (fr) 1995-12-21
US5464546A (en) 1995-11-07
EP0765415A1 (fr) 1997-04-02
ES2121397T3 (es) 1998-11-16
DE59503796D1 (en) 1998-11-05

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