EP0765415A1 - Agents lissants thermostables pour textiles - Google Patents

Agents lissants thermostables pour textiles

Info

Publication number
EP0765415A1
EP0765415A1 EP95923248A EP95923248A EP0765415A1 EP 0765415 A1 EP0765415 A1 EP 0765415A1 EP 95923248 A EP95923248 A EP 95923248A EP 95923248 A EP95923248 A EP 95923248A EP 0765415 A1 EP0765415 A1 EP 0765415A1
Authority
EP
European Patent Office
Prior art keywords
agent according
carbon atoms
esters
smoothing agent
acids
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.)
Granted
Application number
EP95923248A
Other languages
German (de)
English (en)
Other versions
EP0765415B1 (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

Links

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 in the manufacture and processing of synthetic fibers. These spin finishes contain all so-called textile smoothing agents to reduce friction between filaments or fibers and between filaments and guide elements. Esters are increasingly being used as textile smoothing agents. The increasing automation of the manufacturing processes has resulted in extremely high demands being placed on the textile smoothing agents with regard to their thermal stability (thermostability). Even the esters known to be thermally stable can hardly meet these high requirements to a sufficient extent without further additives.
  • antioxidants such as butylated hydroxytoluene (BHT) because such compounds effectively improve the thermostability even in small to medium amounts.
  • BHT and related antioxidants have a relatively high volatility at the temperatures involved in manufacturing and processing textile fibers. As a result, this class of antioxidants evaporates quickly and therefore can only serve its purpose initially, but not for the entire process, to prevent oxidative damage to the textile smoothing agent.
  • 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.
  • WO 91/13134 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 relates in its preferred embodiment 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 the carrier. From an economic and ecological point of view, however, it is desirable to minimize the antioxidant content. Description of the invention
  • the object of the present invention was to provide thermostable textile smoothing agents which avoid the disadvantages of the known prior art.
  • the aim was to develop thermostable textile smoothing agents that require only a minimal amount of antioxidants.
  • R 1 is a monovalent radical and R 2 , R 3 , R 4 are identical or different divalent radicals of alkanes, cycloalkanes, aromatics or alkyl aromatics having 1 to 22 carbon atoms .
  • the polyols a) and the fatty acids b) can be saturated or olefinically unsaturated and can be straight-chain or branched with respect to their carbon skeleton.
  • 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 understood to be polyhydric alcohols having at least 2 OH groups.
  • the chemical constitution of the polyols is not subject to any particular restrictions, i.e. they can be straight or branched.
  • the polyols are preferably selected from the group formed by glycerol, trimethylolpropane, neopentyl glycol and pentaerythritol.
  • 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 in which the thiocarboxylic acids of the general formula (I) and / or (II) are esterified with monofunctional aliphatic alcohols having 1 to 22 carbon atoms, neopentyl glycol, glycerol, trimethylolpropane or pentaerythritol are.
  • monofunctional aliphatic alcohols having 1 to 22 carbon atoms
  • neopentyl glycol glycerol, trimethylolpropane or pentaerythritol are.
  • the polyfunctional alcohols neopentylglycol, glycerol, trimethylolpropane and pentaerythritol can be pure or else mixed esters.
  • “Pure” esters are understood to mean those esters in which all the hydroxyl groups of the polyfunctional alcohols are esterified with one or more thiocarboxylic acids of the general formula (I) and / or (II).
  • "Mixed” esters are such Understood esters in which at least one hydroxyl group is esterified with a thiocarboxylic acid of the general formula (I) or (II). The other hydroxyl groups are then esterified with fatty acids having 6 to 22 carbon atoms, as described in connection with component b).
  • the esters of monofunctional aliphatic alcohols of the type described and the “pure” esters of pentaerythritol are particularly preferred.
  • n- and i-butanol, 2-ethylhexanol, isotridecanol, lauryl alcohol, isostearyl alcohol and / or oleyl alcohol are particularly suitable.
  • 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 ß-laurylthiopropionic acid (C 12 H 25 SCH 2 CH 2 COOH) and ß-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, but are also easily accessible by known esterification reactions.
  • the mixed esters can easily be obtained by transesterification of the pure thioates with the fatty acids described.
  • esters of thiocarboxylic acids are used in an amount of 0.05 to 8% by weight, based on the sum of components a) and b), in the preparation of the thermally stable textile smoothing agents according to the invention. It is preferred to use the esters of thiocarboxylic acids in an amount of 0.5 to 5% by weight, in particular 1.0 to 3.0% by weight. This The amounts used relate to the amounts of pure esters of thiocarboxylic acids defined above. In the case of mixed esters of thiocarboxylic acids, higher amounts are to be used in accordance with the content of thiocarboxylic acids in the ester.
  • the esters of thiocarboxylic acids may be present from the start in the reaction between polyols a) and fatty acids b) or may only be added during the reaction. Furthermore, they can be added in their entirety or in portions.
  • the reaction between polyols a) and the fatty acids b) takes place under the conditions customary for esterification reactions.
  • the presence of the esters of thiocarboxylic acids of the general formula (I) and / or (II) on the one hand improves the thermostability and on the other hand improves the color of the textile smoothing agents obtained, since these are lighter in color than when produced without the presence of the described esters of thiocarboxylic acids.
  • antioxidants are additionally added to the agents according to the invention as additive d). These antioxidants are added after the reaction of the polyols a) with fatty acids b) in the presence of the esters of thiocarboxylic acids. Suitable antioxidants are butylated hydroxytoluene, dialkyl or diaryl phosphonates, trialkyl or triaryl phosphites, ascorbic or citric acid and their derivatives and, in particular, sterically hindered phenols.
  • the sterically hindered phenols of the structure (A-1 and / or A-6) are particularly preferably used as additional additives.
  • 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 much 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 quantities of 1.0% by weight of the sterically hindered Irganox R 1010 phenol - based on components a) to c) - give excellent thermostabilities.
  • the antioxidants d) in an amount of 1: 1 to 1: 4 in relation to the esters of thiocarboxylic acids.
  • Particularly good results are achieved with the sterically hindered phenols if the amount of the additional antioxidants d) is 10 to 50% by weight, based on the esters of thiocarboxylic acids, the range from 20 to 30% by weight being particularly preferred .
  • the textile smoothing agents according to the invention can, owing to their high thermostability, be used, inter alia, in spin finishes.
  • the present invention therefore furthermore relates to spin finishes for synthetic filaments, characterized in that they contain the thermostable textile smoothing agents described.
  • the textile smoothing agent can in turn 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 Tools 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.
  • the thread-locking agents are the polyacrylates, fatty acid sarcosides and / or copolymers with maleic anhydride known from the prior art suitable.
  • 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 produced by intensively mixing the textile smoothing agents according to the invention, if appropriate with the emulsifiers, wetting agents, antistatic agents and, if appropriate, with the customary auxiliaries at about 18-25 ° C.
  • the spin finishes are applied in the form of their aqueous dispersions to the synthetic filament fibers immediately after they emerge from the spinneret.
  • the spin finishes which have a temperature between 18 and 60 ° C, are applied with the help of application rollers or dosing points using suitable applicators.
  • 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).
  • Thermogravic Analyzes method (TGA isothermal method); with thermo balance TGA 951, DuPont, at 230 ° C after 10, 13 and 16 hours.
  • TGA Thermogravic Analyzes method
  • TGA 951, DuPont thermo balance
  • the application examples show that the textile smoothing agents according to the invention have a higher Thermostabi lity than the pure ester (comparison), despite only small additions to the thiocarboxylic acid esters. Furthermore, it can be seen that the addition of the smallest amounts of the sterically hindered phenols improve the thermostability in a synergistic manner (see AB) and AC)). In addition, when using the textile smoothing agents according to the invention, the residues remain lighter in color and more liquid than comparable esters without the addition of the esters of thiocarboxylic acids.

Landscapes

  • 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)

Abstract

L'invention concerne des agents lissants thermostables obtenus par réaction a) de polyols avec b) des acides gras ayant entre 6 et 22 atomes de C, en présence de 0,05 à 8 % en poids, par rapport à la somme des constituants a) et b), c) d'esters d'acides thiocarboxyliques de la formule générale (I) R1-S-R2-COOH et/ou (II) HOOC-R3-S-R4-COOH où R1 désigne un reste monovalent et R?2, R3, R4¿ désignent des restes bivalents identiques ou différents d'alcanes, de cycloalcanes, d'aromatiques ou d'alkylaromatiques ayant entre 1 et 22 atomes de C. Ces agents se caractérisent par leur excellente thermostabilité.
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 true EP0765415A1 (fr) 1997-04-02
EP0765415B1 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
WO2002010114A2 (fr) * 2000-08-02 2002-02-07 Mj Research & Development, L.P. Of Which Mjrd, Llc Is A General Partner Circuit d'huile lubrifiante et frigorigene
EP1609844A4 (fr) * 2003-04-02 2008-02-13 Idemitsu Kosan Co Composition de lubrifiant conducteur
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

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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

Non-Patent Citations (1)

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Title
See references of WO9534708A1 *

Also Published As

Publication number Publication date
WO1995034708A1 (fr) 1995-12-21
EP0765415B1 (fr) 1998-09-30
ES2121397T3 (es) 1998-11-16
US5464546A (en) 1995-11-07
DE59503796D1 (en) 1998-11-05

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