EP0574441A1 - Spinning preparations for man-made filament fibres. - Google Patents
Spinning preparations for man-made filament fibres.Info
- Publication number
- EP0574441A1 EP0574441A1 EP92905481A EP92905481A EP0574441A1 EP 0574441 A1 EP0574441 A1 EP 0574441A1 EP 92905481 A EP92905481 A EP 92905481A EP 92905481 A EP92905481 A EP 92905481A EP 0574441 A1 EP0574441 A1 EP 0574441A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- carbon atoms
- diols
- molecular weight
- alpha
- esters
- 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
Links
Classifications
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- 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
-
- 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
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- 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
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- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
Definitions
- the present invention relates to spin finishes for synthetic filament fibers which contain polyester with a hydrophilic and a hydrophobic part of the molecule as a lubricant.
- the polyesters are block copolymers of hydrophilic polyethylene glycols and hydrophobic diols, selected from the group of polypropylene glycols, polytetrahydrofurans, polycaprolactone diols, hydrogenation products of ricinusic acid esters, dimer diols, 1,2-alkanediols and alpha.omega-alkanediols, and also the polyhydric carboxylic acids and / or their derivatives linking the polyethylene glycols and hydrophobic diols.
- the lubricants in the spin finishes should give the filaments the necessary sliding properties. At the same time, however, the lubricants must be temperature-resistant, non-corrosive, easily removable from the fiber and physiologically harmless so that the requirements for the spin finishes can be met.
- Typical lubricants for spin finishes are vegetable, animal and mineral oils or also synthetic esters, silicones, polyethers, ethoxylated fatty acids and the like (see Ullmanns Encyclopedia of Technical Chemistry, Volume 23, pages 7-9, Verlag Chemie, Weinheim 1983).
- Dicarboxylic acids, monocarboxylic acids and tetrahydrofuran-alkylene oxide random copolymers are also poorly biodegradable.
- polyesters from terephthalic acid, ethylene oxide, propylene oxide and / or butylene oxide and, if appropriate, monocarboxylic acids or monohydric alcohols impart improved synthetic fibers "bindability" and "weavability".
- Polyesters with hydrophilic and hydrophobic molecular parts made from monoalcohols, dicarboxylic acids, secondary alcohols, polyethylene oxide and possibly polypropylene oxide are known as emulsifiers in epoxy resin-containing sizes for carbon and glass fibers from European patent application EP-A-03 93 665. After that
- polyesters have the polyethylene oxide units at the end of the polymer, since only terminal polyethylene oxide units would have a hydrophilic character. Besides, these sizes are made of an epoxy resin and completely unsuitable for polyesters as spin finishes for synthetic fibers, since the sticky epoxy resins too much stick together the synthetic filaments, which leads to thread breaks.
- the object of the present invention is to provide spin finishes for synthetic filament fibers which contain lubricants with improved biodegradability.
- the lubricants should have good lubricating properties due to a hydrophobic part of the molecule and should be easy to incorporate into water by means of a hydrophilic part of the molecule.
- the lubricants should also ensure easy removal from the fiber and the highest possible temperature resistance.
- the present invention relates to spinning preparations for synthetic filament fibers, containing a lubricant with improved biodegradability, characterized in that the lubricant is a block copolyester made from the blocks
- hydrophobic diols selected from the group consisting of polypropylene glycols, polytetrahydrofurans, polycaprolactone diols, hydrogenation products of castor esters, 1,2-alkanediols, alpha, omega-alkanediols and / or dimer diols and the blocks
- the block copolyesters containing the invention are prepared by esterification or transesterification of the carbonic acid diesters, the dicarboxylic acids, their esters and / or their anhydrides with the hydrophilic polyethylene glycols (block A) and the hydrophobic diols (block B), preferably in the presence of an esterification catalyst analyzer and with removal of any water of reaction or the liberated alcohol of the esters.
- an esterification catalyst analyzer preferably in the presence of an esterification catalyst analyzer and with removal of any water of reaction or the liberated alcohol of the esters.
- polyethylene glycols with an average molecular weight of 450 to 20,000, preferably 600 to 3,000, in particular 800 to 2,000, are used as hydrophilic diols (block A) to build up the block copolyesters.
- Polyethylene glycols are commercially available products and are obtained industrially, for example, by base-catalyzed attack by alcoholate anions on ethylene oxide with ring opening and polymerization (compare Ullmann's Encyclopedia of Industrial Chemistry, Volume 19 (1980), Verlag Chemie, Weinheim, pages 31- 38). Within the specified molecular weight range, the polyethylene glycols with different molecular weights can be taken as block A in any mixtures.
- polyethylene glycols with molecular weights of 62 to less than 450 in minor amounts, preferably in amounts of 0.01 to 20% by weight, based on the total amount of polyethylene glycol.
- the emulsifiability of the block copolyesters is advantageous to dispense with polyethylene glycol components with molecular weights below 450.
- non-crystalline block copolyesters that are liquid at room temperature are desired, it is advisable to use polyethylene glycols with the low molecular weights in the stated amounts.
- block B uses hydrophobic diols selected from the group consisting of polypropylene glycols, polytetrahydrofurans, polycaprolactone diols, hydrogenation products of ricinate, 1,2-alkanediols, alpha, omega-alkanediols and / or dimer diols.
- Polypropylene glycols are commercially available products and are produced technically analogously to the polyethylene glycols in the presence of bases as catalysts under polymerization with any molar mass.
- polypropylene glycols with molecular weights from 400 to 8000, preferably from 600 to 4000, although propylene glycol, dipropylene glycol or polypropylene glycols with molecular weights up to 400 in amounts from 0.01 to 20 wt .-% - based on the total amount of hydrophobic diols - can be tolerated.
- Polytetrahydrofurans are also commercially available products and can be obtained by ring-opening polymerization of tetrahydrofuran (see Ullmann's Encyclopedia of technical chemistry, Volume 19 (1980), Verlag Chemie, Weinheim, pages 297-299). Suitable polytetrahydrofurans have a molecular weight between 200 to 8000, preferably 800 to 6000.
- Polycaprolactone diols are also commercially available products and can be used as catalysts at temperatures between 20 ° C. to 20 ° C. by ring-opening polymerization of 6-caprolactone with aliphatic and / or aromatic diols, for example by the so-called interox process in the presence of Lewis acids or organic acids about 150 ° C.
- polycaprolactone diols which have been prepared by ring-opening polymerization using alpha, omega-aliphatic diols having 2 to 36 C atoms, preferably straight-chain, saturated, aliphatic diols having 2 to 22 C atoms .
- alpha, omega-aliphatic diols having 2 to 36 C atoms, preferably straight-chain, saturated, aliphatic diols having 2 to 22 C atoms .
- all polycaprolactone diols with molecular weights of 400 to 4000 are suitable.
- Hydrogenation products of ricinate are sold by the applicant under the name Loxanol R. These are diols which are obtained by complete hydrogenation of the castor fatty acid esters, preferably the castor fatty acid methyl esters.
- the 1,2-alkanediols suitable as hydrophobic diols are preferably aliphatic, saturated 1,2-alkanediols and in particular also unbranched nature.
- Such 1,2-alkanediols are easily accessible, for example by acid-catalyzed ring opening of terminally epoxidized alkanes with water (see Ullmann's Encyclopedia of Technical Chemistry, Volume 7 (1980), Verlag Chemie, Weinheim, pages 227-235 ).
- Aliphatic, saturated, unbranched 1,2-alkanediols having 2 to 24 carbon atoms such as 1,2-octanediol, 1,2-decanediol, 1,2-dodecanediol, 1,2-tetradecanediol, 1,2, are preferred -Hexadecanediol, 1, 2-0ctadecanediol and / or their technical mixtures.
- Alpha, omega-alkanediols have two hydroxyl groups at the end and are accessible by hydrogenation of the corresponding dicarboxylic acids, the preparation of which will be described below. Also for reasons of biodegradability, aliphatic, saturated, unbranched alpha, omega-alkanediols are preferred. Good sliding properties are observed in this hydrophobic group with alpha, o-alkanediols with 6 to 22 carbon atoms.
- 1,8-octanediol 1,10-decanediol, 1,12-dodecanediol, 1,14-tetradecanediol, 1,16-hexadecanediol, 1,18-octadecanediol and / or their technical mixtures are particularly preferred.
- the dimer diols which are also possible as hydrophobic diols, can be prepared by hydrogenating dimeric fatty acids and / or their esters in accordance with German specification DE-B-17 68 313.
- Suitable starting materials are polymerization products of monovalent, mono- and / or polyunsaturated fatty acids and / or their esters, which, if desired, can contain components saturated in minor amounts.
- Suitable polymerization products are derived from oleic acid, linoleic acid, linolenic acid, palmitolinic acid, elaidic acid and / or erucic acid and / or esters of the aforementioned fatty acids and lower aliphatic alcohols, and / or obtained from tallow, olive oil, sunflower oil, soybean oil or cottonseed oil Fatty acid mixtures.
- Dimeral alcohols with 24 to 36 carbon atoms which are accessible by hydrogenation of the dimer fatty acids based on unsaturated fatty acids with 12 to 18 carbon atoms are particularly suitable.
- any mixtures of the hydrophobic diols listed can be used to build up the block copolyesters.
- Good properties are achieved if the hydrophobic diols are selected from the group of the polypropylene glycols with a Molecular weight of 400 to 8000, polytetrahydrofurans with a molecular weight of 200 to 8000, polycaprolactone diols with a molecular weight of 400 to 4000, hydrogenation products of castor esters, alpha, omega-aliphatic alkane diols with 6 to 22 carbon atoms and / or dimer diols with 24 to 36 carbon atoms.
- polypropylene glycols with molecular weights from 400 to 8000 and / or polytetrahydrofurans with molecular weights from 200 to 8000 and particularly exclusively polypropylene glycols with molecular weights from 400 to 8000, which have already been described in more detail, are preferred.
- low-viscosity block copolyesters it is advantageous to use the hydrophilic ones and hydrophobic diols (blocks A and B) with onofunctional alcohols, preferably with onofunctional aliphatic, saturated alcohols with 1 to 22 carbon atoms in amounts of 0.01 to 20 mol% - based on the total amount of diol.
- the hydrophilic polyethylene glycols with the hydrophobic diols are ester groups by means of aliphatic dicarboxylic acids having 2 to 36 carbon atoms, their anhydrides, their esters of aliphatic dicarboxylic acids of lower alcohols having 1 to 8 carbon atoms and / or Kohlenhoffredie ⁇ esters of lower alcohols with 1 to 8 carbon atoms.
- Aliphatic dicarboxylic acids can be obtained, for example, by oxidative degradation of higher monocarboxylic acids or by carbonylation.
- An overview of production methods with literary citations can be found in Ullmann's Encyclopedia of Industrial Chemistry, Volume 10 (1980), Verlag Chemie, Weinheim, pages 135-143.
- Carbonic acid diesters can be prepared by the following processes mentioned in the Houben Weyl "Methods of Organic Chemistry", 4th edition, volume E4, page 66.
- carbon Lens acid diesters of lower alcohols with 1 to 8 carbon atoms such as dimethyl, di-n-propyl, diisopropyl and / or di-2-ethylhexyl carbonate, are suitable.
- aliphatic dicarboxylic acids preference is given to saturated alpha, omega-D carboxylic acids with 2 to 36 carbon atoms, such as oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, brassylic acid, thapis acid, phellogenic acid and / or tetratriacontanedioic acid.
- o ega dicarboxylic acids or in a mixture with these it is of course also possible to use their anhydrides and / or esters, preferably esters of lower alcohols having 1 to 8 carbon atoms.
- dimer fatty acids can also be used to connect blocks A and B.
- dimer fatty acids are prepared by polymerizing mono- and / or polyunsaturated fatty acids and their esters, which, if desired, can also contain saturated components in addition to unsaturated components, in the presence of bases as catalysts.
- dimer fatty acids based on oleic acid, linoleic acid, linolenic acid, palmitoleic acid, eladic acid and / or erucic acid are suitable.
- Blocks A) and B) are particularly preferred, preferably with alpha-omega-aliphatic dicarboxylic acids with 2 to 36 C atoms, esters of alpha, omega-al-phatic dicarboxylic acids with 2 to 36 C atoms and low Alcohols with 1 to 8 carbon atoms and / or anhydrides of alpha, omega-aliphatic dicarboxylic acids with 2 to 36 carbon atoms are combined.
- monofunctional aliphatic carboxylic acids having 1 to 22 carbon atoms in amounts of 0.01 to 20 mol%, based on dicarboxylic acid, can be added, analogously to the diols.
- Spinning preparations are very particularly preferably produced from
- hydrophobic diols selected from the group of polypropylene glycols with a molecular weight of 400 to 8000, polytetrahydrofurans with a molecular weight of 200 to 8000, polycaprolactone diols with a molecular weight of 400 to
- the lubricant of which is a block copolyester B) hydrophobic diols selected from the group of polypropylene glycols with a molecular weight of 400 to 8,000 and polytetrahydrofurans with a molecular weight of 200 to 8,000, in particular polypropylene glycols, are very particularly preferred with a molecular weight of 400 to 8000.
- the spin finishes according to the invention contain block copolyesters as lubricants, with both the sliding properties of the lubricants and the ability of the lubricants to be determined are determined by the weight ratio of the hydrophilic block A and the hydrophobic block B.
- the molecular weight and the degree of polymerization in the block copolyesters is determined above all by the molar ratios of the hydroxyl groups of the diols (OH) to the carboxyl groups of the dicarboxylic acids, their anhydrides, esters and / or carbonic acid diesters (C00H). Sufficient molecular weights are obtained if the molar ratios of hydroxyl groups to carboxyl groups 0H: C00H are selected in the range from 3: 1 to 1: 3, preferably 1.5: 1 to 1: 1.5. Higher molecular weights of the block copolyesters are preferred, so that molar ratios of 0H: C00H in the range from 1.2: 1 to 0.8: 1 are recommended.
- the spin finishes according to the invention can contain, as lubricants, further lubricants known from the prior art, such as mineral oils, fatty acid esters with 8 to 22 C atoms in the fatty acid residue and 1 to 22 C atoms in the alcohol residue, for example palmitic acid methyl ester, isobutyl stearate and / or tallow fatty acid-2-ethylhexyl ester, polyolearbonic acid esters, for example coconut fatty acid esters of glycerol and / or alkoxylated glycerols, silicones, for example dimethylpolysiloxane and / or polyalkylene glycols, for example ethylene oxide-propylene oxide mixed polymers (man-made fibers, textile industry, 1977, page 335).
- mineral oils such as mineral oils, fatty acid esters with 8 to 22 C atoms in the fatty acid residue and 1 to 22 C atoms in the alcohol residue, for example palmitic acid methyl ester,
- the spin finishes according to the invention can contain emulsifiers, wetting agents and / or antistatic agents and, if appropriate, the customary auxiliaries such as pH regulators, thread closure agents, bactericides and / or corrosion inhibitors.
- 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 , oils, fatty alcohols with 8 to 24 carbon atoms and / or Cg-Cig-alkylphenols, for example castor oil with 25 mol ethylene oxide (EO) and / or Ciö-Ci8 fatty alcohol with 8 mol propylene oxide and 6 mol EO, if desired, alkoxylated Cg-C24 fatty acid mono- and / or di-ethanolamides, for example optionally ethoxylated oleic acid mono- and / or diethanolamide, tallow fatty acid mono- and / or diethanolamide and / or coconut fatty acid mono- and
- the thread-closing agents are the polyacrylates, fatty acid sarcosides and / or copolymers with maleic anhydride (Melliand Textilberichte (1977), page 197) and / or polyurethanes according to German published patent application DE-A-3830468, pH value regulators, for example, known from the prior art C 1 -C 4 -carboxylic acids and / or C 1 -C 4 -hydroxycarboxylic acids such as acetic acid and / or glycolic acid, alkali metal hydroxides such as potassium hydroxide and / or A ine such as triethanolamide, bactericides and / or corrosion inhibitors are possible.
- the spin finishes according to the invention are produced by intensively mixing the block copolyesters as lubricants and, if appropriate, further lubricants, emulsifiers, wetting agents, antistatic agents and / or customary auxiliaries at from 18 to 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 metering pumps using suitable applicators.
- emulsifiers 0 to 65% by weight emulsifiers, antistatic agents and / or wetting agents 0 to 10% by weight pH regulators, bactericides and / or corrosion protection agents, the amounts must be chosen so that they add up to 100 wt .-%.
- the lubricants mentioned in this list include the block copolyesters described as well as the lubricants known from the prior art with the proviso that at least 50% by weight, preferably 75 to 100% by weight and in particular 100% by weight of the Lubricants are block copolyesters.
- the application amount of the spin finishes in the form of their aqueous dispersion is in the range customary for the textile industry between 0.1 and 3% by weight, based on the weight of the filament fibers.
- the synthetic filament fibers polypropylene, polyester and / or polyamide are provided alone or as a mixture with the spin finishes according to the invention.
- the spin finishes according to the invention impart the necessary sliding properties to the synthetic filament fibers. Even during the texturing of the synthetic filament fibers, the spin finishes according to the invention prove that the thermal stability is sufficiently high, so that little or no undesirable deposits can be found on the filament fibers and / or the texturing elements.
- the crimping of the synthetic filament fibers treated in the spin finishes according to the invention is also easily possible and stable. However, the spin finishes according to the invention show particular advantages above all in their improved biodegradability.
- Another object of the present invention is the use of block copolyesters made from the blocks
- hydrophobic diols selected from the group of polypropylene glycols, polytetrahydrofurans, polycaprolactone diols, hydrolyzers Curing products of castor fatty acid esters, 1,2-alkanediols, alpha, omega-alkanediols and / or dimer diols and blocks
- block copolyesters used possibly in a mixture with other lubricants, emulsifiers, wetting agents, antistatic agents and / or customary auxiliaries, can also be found from the above, as well as the amount and application of the block copolyesters used.
- Example 2 225 g of polypropylene glycol (MW 1000), 100 g of succinic anhydride, 0.25 g of tin (II) octoate, 880 g of polyethylene glycol (MW 1000) and 100 ml of xylene were reacted analogously to Example 1.
- a waxy block co-polyester was obtained which, as a 10% by weight solution in water, has an opalescent appearance.
- Example 5 To prepare an aqueous dispersion, 10 g of the block copolyester were dissolved in 30 g of isopropanol and 60 g of water were then stirred in. A finely divided, stable dispersion was obtained.
- Example 5 To prepare an aqueous dispersion, 10 g of the block copolyester were dissolved in 30 g of isopropanol and 60 g of water were then stirred in. A finely divided, stable dispersion was obtained.
- Example 5 To prepare an aqueous dispersion, 10 g of the block copolyester were dissolved in 30 g of isopropanol and 60 g of water were then stirred in. A finely divided, stable dispersion was obtained.
- Example 5 To prepare an aqueous dispersion, 10 g of the block copolyester were dissolved in 30 g of isopropanol and 60 g of water were then stirred in. A finely divided, stable dispersion was obtained.
- polyester filaments (yarn type: pre-oriented yarn-PES; fineness: dtex 167, number of filaments: f 34; spinning speed 3300 m / min) applied (oil coating 0.35 wt .-%). The following parameters were determined:
- TGA Thermogravic Analyzes method
- DSC Differential Scanning Colorimetry
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polyesters Or Polycarbonates (AREA)
- Artificial Filaments (AREA)
- Materials For Medical Uses (AREA)
Abstract
Il est décrit des préparations de filature renfermant un agent de glissement à capacité de dégradation biologique améliorée, l'agent de glissement étant constitué par des copolyesters blocs. Les copolyesters blocs sont fabriqués à partir de polyéthylèneglycols hydrophiles et de diolènes hydrophobes, sélectionnés dans le groupe comprenant les polypropylèneglycols, le polytétrahydrofuranne, les polycaprolactone-diols, les produits d'hydratation des esters de l'acide ricinoléique, les 1,2-alcane-diols, les alpha-, oméga-alcane-diols et/ou des diols dimérisés, ainsi que des acides dicarboxyliques aliphatiques de 2 à 36 atomes de carbone liant les blocs A) et B), leurs anhydrides, leurs esters d'alcools inférieurs de 1 à 8 atomes de carbone et/ou leurs diesters d'acides carboxyliques d'alcools inférieurs de 1 à 8 atomes de carbone.There are described spinning preparations containing a slip agent with improved biological degradation capacity, the slip agent being constituted by block copolyesters. Block copolyesters are made from hydrophilic polyethylene glycols and hydrophobic diene, selected from the group consisting of polypropylene glycols, polytetrahydrofuran, polycaprolactone diols, hydration products of ricinoleic acid esters, 1,2-alkane -diols, alpha-, omega-alkane-diols and / or dimerized diols, as well as aliphatic dicarboxylic acids of 2 to 36 carbon atoms linking blocks A) and B), their anhydrides, their lower alcohol esters from 1 to 8 carbon atoms and / or their diesters of carboxylic acids of lower alcohols from 1 to 8 carbon atoms.
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4107283A DE4107283A1 (en) | 1991-03-07 | 1991-03-07 | SPINNING PREPARATIONS FOR SYNTHETIC FILAMENT FIBERS |
DE4107283 | 1991-03-07 | ||
PCT/EP1992/000426 WO1992015749A1 (en) | 1991-03-07 | 1992-02-27 | Spinning preparations for man-made filament fibres |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0574441A1 true EP0574441A1 (en) | 1993-12-22 |
EP0574441B1 EP0574441B1 (en) | 1995-02-01 |
Family
ID=6426677
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP92905481A Expired - Lifetime EP0574441B1 (en) | 1991-03-07 | 1992-02-27 | Spinning preparations for man-made filament fibres |
Country Status (8)
Country | Link |
---|---|
US (1) | US6204353B1 (en) |
EP (1) | EP0574441B1 (en) |
JP (1) | JPH06505062A (en) |
DE (2) | DE4107283A1 (en) |
ES (1) | ES2068029T3 (en) |
MX (1) | MX9201011A (en) |
TR (1) | TR25819A (en) |
WO (1) | WO1992015749A1 (en) |
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DE4202065A1 (en) * | 1992-01-25 | 1993-07-29 | Henkel Kgaa | USE OF BLOCK COPOLYESTERN WITH POLYALKYLENE GLYCOL BLOCKS AS GLAETTE IN SPINNING PREPARATIONS |
DE19525406A1 (en) * | 1995-07-12 | 1997-01-16 | Henkel Kgaa | Production and use of highly viscous oligocarbonates from dimer diol |
JP4299971B2 (en) * | 1998-08-18 | 2009-07-22 | 松本油脂製薬株式会社 | Treatment agent composition for synthetic fibers with good biodegradability |
US6537662B1 (en) * | 1999-01-11 | 2003-03-25 | 3M Innovative Properties Company | Soil-resistant spin finish compositions |
US6045826A (en) * | 1999-04-02 | 2000-04-04 | National Research Council Of Canada | Water-soluble compositions of bioactive lipophilic compounds |
US20080070981A1 (en) | 2000-02-23 | 2008-03-20 | Henryk Borowy-Borowski | Water-soluble compositions of bioactive lipophilic compounds |
US6632443B2 (en) | 2000-02-23 | 2003-10-14 | National Research Council Of Canada | Water-soluble compositions of bioactive lipophilic compounds |
EP1070781A1 (en) * | 1999-07-19 | 2001-01-24 | Clariant International Ltd. | Increase of wet lubricity of textile materials and wet lubricant |
EP1094147A1 (en) | 1999-09-22 | 2001-04-25 | Clariant International Ltd. | Enhancement of the wet sliding property of textile material and a wet sliding agent therefore |
US7144600B2 (en) * | 2003-02-18 | 2006-12-05 | Milliken & Company | Wax-free lubricant for use in sizing yarns, methods using same and fabrics produced therefrom |
US7579047B2 (en) * | 2003-05-20 | 2009-08-25 | Milliken & Company | Lubricant and soil release finish for textured yarns, methods using same and fabrics produced therefrom |
US7824566B2 (en) | 2003-07-08 | 2010-11-02 | Scheidler Karl J | Methods and compositions for improving light-fade resistance and soil repellency of textiles and leathers |
EP1641975A1 (en) * | 2003-07-08 | 2006-04-05 | Karl Scheidler | Methods and compositions for improving light-fade resistance and soil repellency of textiles and leathers |
US8685431B2 (en) * | 2004-03-16 | 2014-04-01 | Advanced Cardiovascular Systems, Inc. | Biologically absorbable coatings for implantable devices based on copolymers having ester bonds and methods for fabricating the same |
US9851341B2 (en) * | 2014-06-27 | 2017-12-26 | Eastman Chemical Company | Fibers with chemical markers used for coding |
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US3725352A (en) * | 1970-12-30 | 1973-04-03 | Union Carbide Corp | Aba block polymers of polyesters and polyethers |
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JPS626982A (en) | 1985-07-02 | 1987-01-13 | 松本油脂製薬株式会社 | Fiber treating composition |
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GB8806419D0 (en) * | 1988-03-18 | 1988-04-20 | Du Pont | Improvements relating to fibres |
JPH0268367A (en) | 1988-08-30 | 1990-03-07 | Sanyo Chem Ind Ltd | Straight-type lubricant for filament yarn |
DE3830468A1 (en) | 1988-09-08 | 1990-03-15 | Henkel Kgaa | POLYURETHANE SPIDER PREPARATIONS |
JPH02120258A (en) * | 1988-10-28 | 1990-05-08 | Dai Ichi Kogyo Seiyaku Co Ltd | Sizing agent for glass fiber |
DE3913145A1 (en) | 1989-04-21 | 1990-10-25 | Basf Ag | LEGS FOR CARBON FIBERS |
-
1991
- 1991-03-07 DE DE4107283A patent/DE4107283A1/en not_active Withdrawn
-
1992
- 1992-02-27 EP EP92905481A patent/EP0574441B1/en not_active Expired - Lifetime
- 1992-02-27 JP JP4504951A patent/JPH06505062A/en active Pending
- 1992-02-27 DE DE59201342T patent/DE59201342D1/en not_active Expired - Fee Related
- 1992-02-27 US US08/117,013 patent/US6204353B1/en not_active Expired - Fee Related
- 1992-02-27 WO PCT/EP1992/000426 patent/WO1992015749A1/en active IP Right Grant
- 1992-02-27 ES ES92905481T patent/ES2068029T3/en not_active Expired - Lifetime
- 1992-03-05 TR TR92/0231A patent/TR25819A/en unknown
- 1992-03-06 MX MX9201011A patent/MX9201011A/en unknown
Non-Patent Citations (1)
Title |
---|
See references of WO9215749A1 * |
Also Published As
Publication number | Publication date |
---|---|
JPH06505062A (en) | 1994-06-09 |
DE59201342D1 (en) | 1995-03-16 |
DE4107283A1 (en) | 1992-09-10 |
US6204353B1 (en) | 2001-03-20 |
WO1992015749A1 (en) | 1992-09-17 |
MX9201011A (en) | 1992-09-01 |
ES2068029T3 (en) | 1995-04-01 |
TR25819A (en) | 1993-09-01 |
EP0574441B1 (en) | 1995-02-01 |
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