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WO1993015257A1 - Utilisation de copolyesters - blocs comportant des blocs polyalkyleneglycol, comme agents de lissage dans des preparations pour filature - Google Patents

Utilisation de copolyesters - blocs comportant des blocs polyalkyleneglycol, comme agents de lissage dans des preparations pour filature Download PDF

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Publication number
WO1993015257A1
WO1993015257A1 PCT/EP1993/000124 EP9300124W WO9315257A1 WO 1993015257 A1 WO1993015257 A1 WO 1993015257A1 EP 9300124 W EP9300124 W EP 9300124W WO 9315257 A1 WO9315257 A1 WO 9315257A1
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Prior art keywords
acid
weight
carbon atoms
atoms
general structure
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.)
Ceased
Application number
PCT/EP1993/000124
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German (de)
English (en)
Inventor
Ulrich Eicken
Raymond Mathis
Norbert Bialas
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Filing date
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Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of WO1993015257A1 publication Critical patent/WO1993015257A1/fr
Anticipated expiration legal-status Critical
Ceased 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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/507—Polyesters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/66—Polyesters containing oxygen in the form of ether groups
    • C08G63/664—Polyesters containing oxygen in the form of ether groups derived from hydroxy carboxylic acids
    • 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

  • the present invention relates to the use of block copolyesters based on polyether alcohols and hydroxycarboxylic acids as smoothing agents in spin finishes for synthetic filaments, a process for producing these block copolyesters and spin finishes containing such smoothing agents.
  • the first process that takes place immediately after the filaments are formed is the treatment of the fiber surface with preparation agents.
  • preparation agents which are mostly referred to as "spin finishes" in the German-language literature, have to be applied to the filaments, among other things, since the original rough surface of the polymer filaments causes high frictional forces.
  • spin finishes In order to reduce these high frictional forces, spinning preparations contain smoothing agents.
  • Typical smoothing agents for spin finishes are vegetable, animal and mineral oils or also synthetic esters, silicones, polyethers and ethoxylated fatty acids, esters and alcohols.
  • the texturing process has been increasingly used by the fiber manufacturers, since texturing enables smooth filament yarns to be converted into voluminous and / or elastic yarns that are produced
  • the smooth filament yarns are twisted, which can be fixed or even increased by thermal treatment under defined tension.
  • the smoothing agents should significantly reduce the friction on the texturing elements and filament fibers, and should be very thermostable, so that no crack products are formed during the thermal treatment that resinify the texturing bar or filaments.
  • thermostable smoothing agents the common addition compounds of ethylene oxide and / or propylene oxide to alcohols can also be used, since these depolymerize almost completely without residue during the thermal treatment and are therefore removed from the texturing rail.
  • the object of the present invention was to provide readily biodegradable smoothing agents which, on the one hand, reduce the high friction in spin finishes on filaments and, on the other hand, are temperature-stable up to about 250 ° C. under the conditions of the thermal treatment during texturing.
  • block copolyesters with blocks of polyether alcohols and hydroxycarboxylic acids or polyhydroxycarboxylic acids solve this task.
  • Block copolyesters with blocks of polyalkylene glycols and polymerized hydroxycarboxylic acids are mentioned as suitable textile lubricants from German published patent application DE-A-24 30 342, but no more precise details can be found there.
  • common textile lubricants differ from smoothing agents for spin finishes in their requirements, especially with regard to thermal stability. Accordingly, it cannot be inferred from the reference in the German Offenlegungs ⁇ that these block copolyesters are also suitable smoothing agents for spin finishes.
  • An object of the present invention is accordingly the use of block copolyesters of the general structure (A-C00) m -B, where an integer from 2 to 6 means and
  • R H, or an optionally substituted alkyl and / or
  • Alkenyl radical with 1 to 24 carbon atoms R * H, or an optionally substituted alkyl and / or
  • B an m-valent radical of a polyether alcohol with an average molecular weight of 400 to 6000 and with 2 to 6 hydroxyl groups selected from the group of polyalkylene glycols, adducts of ethylene, propylene and / or butylene oxide with aliphatic diols with 2 to 36 C atoms and / or on aliphatic polyols with 3 to 6 hydroxyl groups and with 4 to 10 C atoms, as a smoothing agent in spin finishes for synthetic filaments.
  • the block copolyesters of the general structure used for the purposes of the invention are known compounds which are described in German Offenlegungsschrift DE-A-2430342 or in European Patent EP-B-424.
  • the block copolyesters used according to the invention are derived from the complex monocarboxylic acids of the general structure A-C00H and / or their derivatives such as lower esters of alkanols with 1 to 6 C atoms and also from polyether alcohols with an average molecular weight of 400 to 6000 and with 2 to 6 hydroxyl groups.
  • the complex monocarboxylic acids correspond to those in German Offenlegungsschrift DE-A-2430342 and European patent EP-B-424 and are in turn derived from monohydroxymonocarboxylic acids of the general structure (A2) '
  • R1, R2 and p have the meaning given for the general structure (A).
  • suitable monohydroxymonocarboxylic acids are, in particular, 12-hydroxystearic acid and / or 9 c-octadecen-12-ol acid (ricinoleic acid). 12-hydroxystearic acid is accessible by hydrogenating ricinoleic acid.
  • Ricinoleic acid itself, in the form of its triglycerides, is the main constituent of castor oil, which still contains triglycerides of palmitic, stearic, oleic and linoleic acid - to name the most important.
  • the technical ricinoleic acid obtained from castor oil therefore always contains the monocarboxylic acid palmitic, stearic, oleic and linoleic acid in quantities depending on the area of cultivation and crop failure.
  • the monocarboxylic acids listed are contained in amounts of about 5 to 20% by weight. From this it can be deduced that the technical 12-hydroxystearic acid obtained by hydrogenation of technical ricinoleic acid also contains monocarboxylic acids as an impurity, especially stearic acid.
  • the complex monocarboxylic acid of the general structure A-COOH can be prepared according to German published patent application DE-A-2430342 by intermolecular esterification of the monohydroxymonocarboxylic acids (A2) in the presence of a conventional monocarboxylic acid which contains no hydroxyl groups and accordingly acts as a chain terminator .
  • the carboxylic acid acting as a chain terminator is provided by the RCO group in the general structure (A).
  • the 12-hydroxystearic acid and ricinoleic acid preferred in the context of the invention always contain, as mentioned, the impurities palmitic, stearic, oleic and linoleic acid, the RCO group of the general structure (A) preferred for the alkyl and / or alkenyl radical derived from these acids.
  • the amount of chain terminating monocarboxylic acid present determines the number of condensed monohydroxy monocarboxylic acids, ie the index n.
  • the amount of chain terminating monocarboxylic acid can be determined by simple experiments and calculations.
  • fertilizer A is derived from technical 12-hydroxystearic acid and / or technical ricinoleic acid.
  • A is very particularly preferably derived from technical 12-hydroxystearic and / or technical ricinoleic acid and has a degree of polymerization n in the range from 1.5 to 10.
  • B represents an m-valent radical of a polyether alcohol having 2 to 6 hydroxyl groups and an average molecular weight of 400 to 6000.
  • polyether alcohol is used for those compounds which have at least two ether groups and have at least two free hydroxyl groups. Accordingly, the polyether alcohols are selected from the group already described.
  • the adducts are preferably those of ethylene oxide and / or propylene oxide with aliphatic saturated diols having 2 to 22 carbon atoms, such as ethylene glycol, neopentyl glycol, 1,4-butanediol, 1,8-octanediol, 1,12-dodecanediol and 1,18-octadecanediol and / or those of ethylene oxide and / or propylene oxide on glycerol, trimethylolpropane for pentaerythritol and / or dipentaerythritol.
  • the polyalkylene glycols can be homopolymers and copolymers and the latter can be block and random polymers of ethylene, propylene and butylene oxide.
  • B particularly preferably represents a divalent radical of a polyether alcohol, ie m denotes the number 2.
  • polyethylene glycols are particularly suitable, preferably with a molecular weight of 600 to 3000 and in particular of 800 to 1500.
  • block copolyesters of the general structure are used in which B is the divalent radical of a polyethylene glycol with a molecular weight of 800 to 1500, in particular up to 1200, and A is derived from a complex monocarboxylic acid based on technical 12- Hydroxystearic acid and / or technical ricinoleic acid and the degree of polymerization n a Number from 1 to 10 means.
  • B is the divalent radical of a polyethylene glycol with a molecular weight of 800 to 1500, in particular up to 1200
  • A is derived from a complex monocarboxylic acid based on technical 12- Hydroxystearic acid and / or technical ricinoleic acid and the degree of polymerization
  • n a Number from 1 to 10 means.
  • the block copolyesters used according to the invention can be produced either by a one-pot process or by a step process.
  • the monohydroxymonocarboxylic acids are first partially or completely esterified with one another (precondensed) in the presence of chain-terminating monocarboxylic acids.
  • These precondensed complex monocarboxylic acids which correspond to the general structure A-C00H, are then esterified with the polyether alcohols until almost all of the hydroxyl and carboxyl groups have reacted.
  • the monohydroxymonocarboxylic acids (A2), monocarboxylic acids and polyether alcohols are esterified with one another from the start in a reaction vessel.
  • the block copolyesters obtained by both processes are very similar in composition and in properties.
  • the block copolyesters used according to the invention can be produced by a new process which is characterized in that esters of the complex monocarboxylic acid of the general structure A-C00H with lower alkanols having 1 to 6 carbon atoms with polyether alcohols the average molecular weight of 400 to 6000 with 2 to 6 hydroxyl groups selected from the group of polyalkylene glycols, adducts of ethylene, propylene and / or
  • Butylene oxide can be esterified on aliphatic diols with 2 to 36 C atoms and / or on aliphatic polyols with 3 to 6 hydroxyl groups and with 4 to 10 C atoms with simultaneous removal of the resulting alcohols with 1 to 6 C atoms.
  • the monomeric or polymeric (precondensed) monohydroxycarboxylic acid instead of the monomeric or polymeric (precondensed) monohydroxycarboxylic acid, its esters with alkanols having 1 to 6 carbon atoms are used.
  • the ester of the precondensed monohydroxycarboxylic acid can also be used.
  • the ester and the polyether alcohol are in any case transesterified in a one-pot process in the customary manner with simultaneous removal of the alkanol having 1 to 6 carbon atoms which is formed.
  • esterification known per se or the esterification according to the invention is carried out in weight ratios of polyether alcohol to, optionally precondensed, hydroxycarboxylic acid of 1: 9 to 9: 1.
  • block copolyesters are surprisingly obtained, in particular when the same proportions by weight are used, which give finely divided and more stable aqueous dispersions than those obtained by the normal esterification processes according to German Offenlegungsschrift DE-A-2430342 and European Patent EP-B- 424 block copolyesters produced.
  • the esterification or transesterification is generally carried out in the presence of the known catalysts such as titanium tetrabutylate, tin octoate or sodium methylate.
  • the block copolyesters can be used alone or in a mixture with lubricants known from the prior art.
  • Suitable smoothing agents are to be selected from the group of mineral oils, fatty acid esters of alkanols with 8 to 22 carbon atoms in the fatty acid residue and 1 to 22 carbon atoms in the alcohol residue, for example methyl palmitate, isobutyl stearate and / or 2-ethylhexyl tallow fatty acid, fatty acid esters of polyols with 2 to 6 hydroxyl groups, for example coconut fatty acid esters of glycerol, alkoxylated alcohols, for example adducts of ethylene oxide (EO) and propylene oxide (PO) with tallow alcohol, tri ethylol propane and / or pentaerythritol, polyalkylene glycols, for example ethylene oxide / propylene oxide mixed polymers , Guerbet alcohols such as 2-butylhexanol, 2-hexyloctanol and / or silicones.
  • EO ethylene oxide
  • PO propylene
  • fatty acid esters of alkanols with 1 to 12 carbon atoms in the alcohol residue are fatty acid esters of alkanols with 1 to 12 carbon atoms in the alcohol residue, ethylene oxide / propylene oxide copolymers of alkanols with 2 to 22 carbon atoms, such as propanol, butanol, capron alcohol, pelargon alcohol, lauryl alcohol, myristyl alcohol, palmityl alcohol, Stearyl alcohol and / or behenyl alcohol, aliphatic diols with 6 to 25 C atoms and / or polyols such as trimethylolpropane, pentaerythritol, neopentyl glycol and / or glycerol as well as Guerbet alcohols with a total of 6 to 38 C atoms.
  • ethylene oxide / propylene oxide copolymers of alkanols with 2 to 22 carbon atoms such as propanol, butanol
  • the block copolyesters are particularly preferably used in the sense of the invention in a mixture with the known known smoothing agents, 15 to 95% by weight of block copolyesters and 5 to 85% by weight of the smoothing agents described being able to make up.
  • the block copolyesters are particularly preferably used in amounts of 50 to 90, preferably 60 to 85% by weight with the known smoothing agents in amounts of 10 to 50, preferably 15 to 40% by weight, based on the mixture of smoothing agents.
  • smoothing agents as diverse as fatty acid esters and ethylene oxide / propylene oxide copolymers can be incorporated into the block copolyesters without phase separation occurring.
  • ethylhexyl stearate and an ethylene oxide / propylene oxide copolymer (Breox ⁇ from BP Chemicals) are not compatible (phase separation), but each that in itself with the block copolyesters.
  • Mixtures of the block copolyesters with the known smoothing agents of the type described are single-phase and can be easily emulsified in water.
  • the block copolyesters are applied alone or in a mixture with other smoothing agents, preferably from an aqueous dispersion in the form of a suspension or emulsion.
  • the block copolyesters are generally emulsified in water before application. It has proven particularly advantageous in the present invention that the block copolyesters are self-emulsifying in water, so that emulsifiers can be dispensed with.
  • emulsifiers known from the prior art, such as mono- and / or diglycerides, for example glyceryl mono- and / or glycerol dioleate, alkoxylated, preferably ethoxylated and / or propoxylated fats, oils, fatty alcohols with 8 to 24 carbon atoms and / or CQ- to Cig-alkylphenols, for example castor oil with 25 moles of ethylene oxide and / or CQ- to Ci8 ⁇ fatty alcohol with 8 moles of propylene oxide and 6 moles of ethylene oxide, if desired alkoxylated ZQ- to C24 ⁇ fatty acid mono- and / or diethanola ide, for example ethoxylated oleic acid mono- and / or diethanolamide, tallow fatty acid mono- and / or diethanolamide and / or coconut fatty acid mono- and / or diethanolamide is possible in customary amounts, if desired.
  • antistatics such as alkali and / or ammonium salts of alkoxylated, preferably ethoxylated and / or propoxylated, optionally end-capped Cg to C22 ⁇ al yl and / or CQ to C22 _A alkylene alcohol sulfonates, Reaction products from optionally alkoxylated CQ to C22 _A 1'yl alcohols with phosphorus pentoxide or phosphorus oxychloride in the form of their alkali Li, ammonium and / or amine salts, for example phosphoric acid esters of ethoxylated Ci2-Ci4 ⁇ fatty alcohols, neutralized with alkanolamine, alkali and / or ammonium salts of Cg- to C22 ⁇ alkyl sulfosuccinates and / or amine oxides.
  • the block copolyesters used according to the invention can also be mixed with customary auxiliaries from the group of thread closing agents, pH regulators, bactericides and / or corrosion inhibitors.
  • the thread-closing agents which are known from the prior art are polyacrylates, fatty acid sarcosides and / or copolymers with maleic anhydride (Melliand Textile Reports (1977), page 197) and / or polyurethanes in accordance with German Offenlegungsschrift DE-A-3839468.
  • pH regulators are, for example, Ci to C4 carboxylic acids and / or Ci to C4 hydroxycarboxylic acids, alkali metal hydroxides and / or amines.
  • the block copolyesters are preferably used in the form of their aqueous dispersion.
  • the aqueous dispersions of the block copolyesters have a water content of 99.8 to 60% by weight and an active substance content of block copolyesters of between 0.2 to 40% by weight.
  • Aqueous dispersions with an active substance content of block copolyesters between 0.2 to 10% by weight are recommended for laboratory tests, in particular for filament free of preparation.
  • the active substance content is preferably between 3 to 40 and in particular between 5 to 30% by weight.
  • the application amount of the aqueous dispersion is in the range customary for the textile industry between 0.1 and 30% by weight, preferably between 1 and 10% by weight, based on the weight of the filaments.
  • block copolyesters according to the invention enables synthetic filaments to be imparted the required smoothness properties, in particular the synthetic filaments made of polypropylene, polyester and / or polyamide and in particular polyester.
  • Another object of the invention are spin finishes for synthetic filaments containing a mixture of smoothing agents, characterized in that the mixture of smoothing agents consists of
  • block copolyester of the general structure (A-C00) m B with the meanings given in claim 1 for A, B and m and 5 to 85 wt .-% smoothing agents liquid at room temperature selected from the group mineral oils, fatty acid esters with 8 to 22 carbon atoms in the fatty acid residue and 1 to 22 carbon atoms in the alkanol, fatty acid esters of polyols with 2 to 6 hydroxyl groups, alkoxylated alcohols, Guerbet alcohols, polyalkylene glycols and silicones.
  • spin finishes whose mixture of smoothing agents consists of block copolyesters of the general structure, where A is derived from the complex monocarboxylic acid based on technical 12-hydroxystearic acid and / or technical ricinoleic acid and B is a divalent polyethylene glycol radical and fatty acid esters with 8 to 22 C- Atoms in the fat residue and 1 to 22 carbon atoms in the alkanol residue.
  • the spin finishes can additionally contain the emulsifiers already described in amounts of 0.1 to 5, the anti-static agents described in amounts of 0.1 to 5, customary auxiliaries from the group of thread-closing agents described, pH value regulators, Contain bactericides and / or anti-corrosion agents in amounts of 0.1 to 5% by weight, based on the spin finish, the 100% by weight missing amounts being water.
  • the spin finishes preferably contain water in amounts of 99.8 to 60% by weight and a total active substance content of 0.2 to 40% by weight.
  • the total active substance content is the content of all components of the spin finish except water, whereby for laboratory applications the total Active substance content is preferably in the range from 0.2 to 10% by weight and for practical applications is between 3 to 40% by weight.
  • the average particle diameter in an aqueous dispersion (10% by weight of active substance) is 260 nm.
  • 500 g of ricinoleic acid with an acid number of 173 were analogous to Example 1 with 500 g of polyethylene glycol with an average molecular weight of 1000 esterified with xylene as entrainer (12 hours) until a paste-like copolyester with the acid number 4.7 was obtained after azeotropic distillation of water and removal of xylene.
  • esters from pre-fatty acid and pentaerythritol 80 parts by weight of esters from pre-fatty acid and pentaerythritol and 20 parts by weight of Breox R 50 A 380; BP Chemicals: cloudy, 2 phases
  • copolyester was carried out using the dish test: 3 g of copolyester according to Example 2 were weighed into an aluminum dish and stored in a drying cabinet at 180 to 200 ° C. for 3 to 18 hours, cooled and weighed. The mass loss in% was recorded. Table 3 shows the results for thermal resistance.
  • Block copolyester according to Example 2 was converted into a 0.4 or 0.8% by weight dispersion with water.
  • Block copolyester according to Example 5 was converted into a 0.4 or 0.8% by weight dispersion with water.
  • spin preparation 1 80 parts by weight of spin preparation 1 (0.4 or 0.8% by weight) were mixed with 20 parts by weight of spin preparation VI (0.4 or 0.8% by weight) as in spin preparation 3 mixed.
  • spin preparation 1 70 parts by weight of spin preparation 1 (0.4 or 0.8% by weight) were mixed with 30 parts by weight of spin preparation V2 (0.4 or 0.8% by weight) from butanol • 50 %
  • spin preparation V2 0.4 or 0.8% by weight
  • E0 ⁇ 50% by weight of propylene oxide (PO) (MW approximately 1200) is added analogously to spin preparation 3.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

L'invention a pour objet l'utilisation de copolyesters-blocs de formule (A-COO)m-B, dans laquelle A désigne le reste d'un acide monocarboxylique complexe, et B, le reste de valence m, d'un polyéther-alcool de poids moléculaire moyen compris entre 400 et 6000, et m = 2 à 6 groupes hydroxyle, comme agents de lissage dans des préparations pour filature de filaments synthétiques, un procédé de fabrication de ces copolyesters-blocs, ainsi que les préparations pour filature renfermant lesdits agents de lissage.
PCT/EP1993/000124 1992-01-25 1993-01-20 Utilisation de copolyesters - blocs comportant des blocs polyalkyleneglycol, comme agents de lissage dans des preparations pour filature Ceased WO1993015257A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19924202065 DE4202065A1 (de) 1992-01-25 1992-01-25 Verwendung von blockcopolyestern mit polyalkylenglykolbloecken als glaettemittel in spinnpraeparationen
DEP4202065.4 1992-01-25

Publications (1)

Publication Number Publication Date
WO1993015257A1 true WO1993015257A1 (fr) 1993-08-05

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PCT/EP1993/000124 Ceased WO1993015257A1 (fr) 1992-01-25 1993-01-20 Utilisation de copolyesters - blocs comportant des blocs polyalkyleneglycol, comme agents de lissage dans des preparations pour filature

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DE (1) DE4202065A1 (fr)
WO (1) WO1993015257A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995007742A1 (fr) * 1993-09-15 1995-03-23 Henkel Kommanditgesellschaft Auf Aktien Polymeres sequences contenant des groupes esters, utiles comme agents anti-mousse pour systemes aqueux
CN118345636A (zh) * 2024-06-18 2024-07-16 淄博鲁瑞精细化工有限公司 一种低泡型纱线平滑剂及其制备方法

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5646212A (en) * 1994-09-02 1997-07-08 Ici Americas Inc. Polyalkylene glycol anhydroxy carboxylic acid dispersant
DE4442966A1 (de) * 1994-12-02 1996-06-05 Henkel Kgaa Wasser-in-Öl-Emulsionen
DE10148002A1 (de) * 2001-09-28 2003-04-24 Goldschmidt Ag Th Gleit- und Trennmittel für Gummiformkörper
JP2005146279A (ja) 2003-11-10 2005-06-09 Gr Advanced Materials Ltd エマルションインク
GB0424505D0 (en) 2004-11-05 2004-12-08 Gr Advanced Materials Ltd Emulsion ink

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1172085A (en) * 1965-10-21 1969-11-26 Teijin Ltd Process for improving Surface Characteristics of Polyester Shaped Articles
DE2430342A1 (de) * 1973-06-25 1975-01-16 Ici Ltd Neue verbindungen
GB1455091A (en) * 1974-02-11 1976-11-10 Toyo Boseki Dispersion of linear polyester resin
EP0000424A1 (fr) * 1977-07-12 1979-01-24 Imperial Chemical Industries Plc Copolymères à bloc ester-éther, linéaires ou ramifiés, et leur utilisation comme agents tensioactifs, seuls ou en mélanges avec des agents tensioactifs usuels
WO1992015749A1 (fr) * 1991-03-07 1992-09-17 Henkel Kommanditgesellschaft Auf Aktien Preparations de filature pour fibres en filaments synthetiques

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1172085A (en) * 1965-10-21 1969-11-26 Teijin Ltd Process for improving Surface Characteristics of Polyester Shaped Articles
DE2430342A1 (de) * 1973-06-25 1975-01-16 Ici Ltd Neue verbindungen
GB1455091A (en) * 1974-02-11 1976-11-10 Toyo Boseki Dispersion of linear polyester resin
EP0000424A1 (fr) * 1977-07-12 1979-01-24 Imperial Chemical Industries Plc Copolymères à bloc ester-éther, linéaires ou ramifiés, et leur utilisation comme agents tensioactifs, seuls ou en mélanges avec des agents tensioactifs usuels
WO1992015749A1 (fr) * 1991-03-07 1992-09-17 Henkel Kommanditgesellschaft Auf Aktien Preparations de filature pour fibres en filaments synthetiques

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995007742A1 (fr) * 1993-09-15 1995-03-23 Henkel Kommanditgesellschaft Auf Aktien Polymeres sequences contenant des groupes esters, utiles comme agents anti-mousse pour systemes aqueux
US5710207A (en) * 1993-09-15 1998-01-20 Henkel Kommanditgesellschaft Auf Aktien Block polymers containing ester groups as defoamers for aqueous systems
CN118345636A (zh) * 2024-06-18 2024-07-16 淄博鲁瑞精细化工有限公司 一种低泡型纱线平滑剂及其制备方法

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