EP0574441B1 - Preparations de filature pour fibres en filaments synthetiques - Google Patents
Preparations de filature pour fibres en filaments synthetiques Download PDFInfo
- Publication number
- EP0574441B1 EP0574441B1 EP92905481A EP92905481A EP0574441B1 EP 0574441 B1 EP0574441 B1 EP 0574441B1 EP 92905481 A EP92905481 A EP 92905481A EP 92905481 A EP92905481 A EP 92905481A EP 0574441 B1 EP0574441 B1 EP 0574441B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- carbon atoms
- molecular weight
- diols
- aliphatic
- dicarboxylic 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.)
- Expired - Lifetime
Links
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- 239000002736 nonionic surfactant Substances 0.000 description 1
- AEIJTFQOBWATKX-UHFFFAOYSA-N octane-1,2-diol Chemical compound CCCCCCC(O)CO AEIJTFQOBWATKX-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 150000002888 oleic acid derivatives Chemical class 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000006864 oxidative decomposition reaction Methods 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- XLKZJJVNBQCVIX-UHFFFAOYSA-N tetradecane-1,14-diol Chemical compound OCCCCCCCCCCCCCCO XLKZJJVNBQCVIX-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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
-
- 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
-
- 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 ricinate esters, dimer diols, 1,2-alkanediols and alpha, omega-alkanediols, and also the polyethylene glycols and hydrophobes Diol-linking polyvalent carboxylic acids and / or their derivatives.
- 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 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 (cf. Ullmanns Encyclopedia of Technical Chemistry, Volume 23, pages 7-9, Verlag Chemie, Weinheim 1983).
- Japanese published patent application JP-A-63/235576 discloses spin finishes for polyester fibers based on polyesters made from dicarboxylic acids, monocarboxylic acids and tetrahydrofuran-alkylene oxide random copolymers. However, these are also poorly biodegradable. According to Japanese published patent application JP-A-62/006982 (cf. Chemical Abstracts, Vol. 107: 79426c), applied polyesters made of terephthalic acid, ethylene oxide, propylene oxide and / or butylene oxide and, if appropriate, monocarboxylic acids or monohydric alcohols impart improved "bindability" and "weavability". There is no indication of the importance of a hydrophobic and hydrophilic part of the molecule in polyester. It is also exclusively polyester based on aromatic terephthalic acid, which is poorly biodegradable.
- Polyesters with hydrophilic and hydrophobic molecular parts from monoalcohols, dicarboxylic acids, secondary alcohols, polyethylene oxide and optionally polypropylene oxide are known as emulsifiers in epoxy resin-containing sizes for carbon and glass fibers from the European patent application EP-A-03 93 665. According to the teaching of this type, it is essential to the invention that the polyesters have the polyethylene oxide units at the polymer end, since only terminal polyethylene oxide units would have a hydrophilic character. Besides, these sizes are made of an epoxy resin and completely unsuitable for polyester as spinning preparations for synthetic fibers, since the sticky epoxy resins stick the synthetic filaments too much together, causing 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 sliding 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 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 and with removal any water of reaction or the alcohol released from the esters.
- block A hydrophilic polyethylene glycols
- block B hydrophobic diols
- 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 (see 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 if there are no polyethylene glycol components with molecular weights below 450.
- non-crystalline block copolyesters that are liquid at room temperature it is advisable to use polyethylene glycols with the low molecular weights in the stated amounts.
- hydrophobic diols selected from the group of the polypropylene glycols, polytetrahydrofurans, polycaprolactone diols, hydrogenation products of ricinate, 1,2-alkanediols, alpha, omega-alkanediols and / or dimerdiols are used as block B.
- Polypropylene glycols are commercially available products and are produced industrially analogously to the polyethylene glycols in the presence of bases as catalysts with polymerization with any molar mass.
- polypropylene glycols with molecular weights from 400 to 8,000, preferably from 600 to 4,000, although propylene glycol, dipropylene glycol or polypropylene glycols with molecular weights up to 400 in quantities 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 Industrial Chemistry, Volume 19 (1980), Verlag Chemie, Weinheim, pages 297-299). Suitable polytetrahydrofurans have a molecular weight between 200 to 8,000, preferably 800 to 6,000.
- Polycaprolactone diols are also commercially available products and can be used as catalysts at temperatures between 20 ° C. to about 150 by ring-opening polymerization of ⁇ -caprolactone with aliphatic and / or aromatic diols, for example by the so-called interox process in the presence of Lewis acids or organic acids ° C. Because of their biodegradability, preference is given to 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. In principle, however, all polycaprolactone diols with molecular weights of 400 to 4,000 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 ester.
- the 1,2-alkanediols which are suitable as hydrophobic diols are preferably aliphatic, saturated 1,2-alkanediols and, more particularly, are unbranched in 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 Industrial 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-hexadecanediol, are preferred , 1,2-octadecanediol 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 alkane diols are preferred. Good sliding properties are observed in this hydrophobic group with alpha, omega-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 monohydric, mono- and / or polyunsaturated fatty acids and / or their esters, which may contain saturated components in minor amounts if desired.
- Suitable polymerization products are derived from oleic acid, linoleic acid, linolenic acid, palmitolic acid, elaidic acid and / or erucic acid and / or esters of the aforementioned fatty acids and lower aliphatic alcohols, and / or fatty acid mixtures obtained from tallow, olive oil, sunflower oil, soybean oil or cottonseed oil. 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 8,000, polytetrahydrofurans with a molecular weight of 200 to 8,000, polycaprolactone diols with a molecular weight of 400 to 4,000, hydrogenation products of ricinate, alpha, omega-aliphatic alkane diols with 6 to 22 carbon atoms and / or dimer diols with 24 up to 36 carbon atoms.
- the polypropylene glycols with molecular weights from 400 to 8,000 and / or polytetrahydrofurans with molecular weights from 200 to 8,000 and in particular exclusively polypropylene glycols with molecular weights from 400 to 8,000, which are already described in more detail.
- the hydrophilic and Mix hydrophobic diols (blocks A and B) with monofunctional alcohols, preferably with monofunctional 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 via ester groups using aliphatic dicarboxylic acids with 2 to 36 C atoms, their anhydrides, their esters of aliphatic dicarboxylic acids of lower alcohols with 1 to 8 C atoms and / or Carbonic acid diesters 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 types of production with citations can be found in Ullmann's Encyclopedia of Technical 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. Carbonic acid diesters are used for transesterification 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-dicarboxylic acids having 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, thapissic acid, phellogenic acid and / or tetratriaconic acid.
- alpha, omega-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 with preferably alpha, omega-aliphatic dicarboxylic acids with 2 to 36 C atoms, esters of alpha, omega-aliphatic dicarboxylic acids with 2 to 36 C atoms and lower alcohols with 1 to 8 C atoms Atoms and / or anhydrides of alpha, omega-aliphatic dicarboxylic acids with 2 to 36 carbon atoms connected.
- monofunctional aliphatic carboxylic acids with 1 to 22 carbon atoms in amounts of 0.01 to 20 mol%, based on dicarboxylic acid, can be added, analogously to the diols.
- the spin finishes according to the invention contain block copolyesters as lubricants, both the sliding properties of the lubricants and the emulsifiability of the lubricants being determined by the weight ratio of the hydrophilic block A and the hydrophobic block B. Still sufficient sliding properties can be observed if the weight ratio of the blocks A: B 90:10 to 1:99. Increasing amounts of hydrophilic polyethylene glycols improve the emulsifiability; well-emulsifiable block copolyesters are obtained with weight ratios of blocks A: B of 20:80.
- the molecular weight and degree of polymerization in the block copolyesters is primarily determined 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 (COOH). Sufficient molecular weights are obtained if the molar ratios of hydroxyl groups to carboxyl groups OH: COOH 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 OH: COOH 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 methyl palmitate, isobutyl stearate and / or tallow fatty acid 2-ethylhexyl ester, polyol carboxylic 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 methyl palmitate, isobutyl ste
- 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 C8-C18 alkylphenols, for example castor oil with 25 mol ethylene oxide (EO) and / or C16-C18 fatty alcohol with 8 mol propylene oxide and 6 mol EO, if desired alkoxylated C8-C24 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 diethanolamide,
- Optional components can be the usual auxiliary substances.
- the thread-closing agents are the polyacrylates, fatty acid arcosides and / or copolymers with maleic anhydride (Melliand Textile Reports (1977), page 197) and / or polyurethanes according to the German patent application DE-A-38 30 468 known from the prior art, pH value regulators , for example C1-C4-carboxylic acids and / or C1-C4-hydroxycarboxylic acids such as acetic acid and / or glycolic acid, alkali metal hydroxides such as potassium hydroxide and / or amines such as triethanolamide, bactericides and / or corrosion inhibitors 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 exiting 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.
- the spin finishes according to the invention contain 35 to 100% by weight of lubricant, 0 to 65% by weight of emulsifiers, antistatic agents and / or wetting agents 0 to 10% by weight of pH regulators, bactericides and / or anti-corrosion 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 required sliding properties to the synthetic filament fibers. Even during the texturing of the synthetic filament fibers, the spin finishes according to the invention have sufficiently high thermal stabilities so that no or only slight 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.
- 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.
- MG 1000 polypropylene glycol
- MG 1000 polyethylene glycol
- tin (II) octoate 100 ml were stirred in an N2 stream Xylene and 92.7
- 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 copolyester was obtained which, as a 10% by weight solution in water, has an opalescent appearance.
- 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.
- a 7.5% by weight spin preparation of block copolyesters from the various examples was applied in water to polyester filaments (yarn type: pre-oriented yarn-PES; fineness: dtex 167, number of filaments: f 34; spinning speed 3300 m / min) (oil coating 0 , 35% by weight).
- the spin finishes with the block copolyesters according to the invention show, compared to the commercially available comparable sliding properties, stick / slip values, crimps and heater and pane evaluations.
- the electrical charges are a little worse, but in acceptable ranges, which can be increased to the desired level by adding antistatic agents.
- the thermal resistance also meets the high requirements of the fiber manufacturers.
- the block copolyesters are clearly superior to the commercially available products in their biodegradability (see Table 3).
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)
- Biological Depolymerization Polymers (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Chemical Treatment Of Fibers During Manufacturing Processes (AREA)
Abstract
Claims (10)
- Préparations de filature pour fibres de filaments synthétiques, contenant un lubrifiant à biodégradabilité améliorée, caractérisées en ce que le lubrifiant est un copolyester en masse préparé à partir des blocs :A) polyéthylèneglycols ayant un poids moléculaire de 450 à 20 000 etB) diols hydrophobes choisis dans le groupe des polypropylèneglycols, polytétrahydrofuranes, poly(caprolactonediols), produits d'hydrogénation des esters de l'acide ricinique, 1,2-alcanediols, alpha, oméga-alcanediols et/ou diols dimères et des acides dicarboxyliques ayant 2 à 36 atomes de C aliphatiques qui relient les blocs A) et B), leurs anhydrides, leurs esters d'alcools inférieurs de 1 à 8 atomes de C et/ou les diesters d'acide carbonique et d'alcools inférieurs de 1 à 8 atomes de C.
- Préparations de filature selon la revendication 1, caractérisées en ce que le lubrifiant est un copolyester en masse dans lequel les blocs A) et B) sont reliés par des diesters d'acide carbonique d'alcools inférieurs de 1 à 8 atomes de C, d'acides alpha, oméga-dicarboxyliques aliphatiques de 2 à 36 atomes de C, d'esters d'acides alpha-omega-dicarboxyliques aliphatiques avec de 2 à 36 atomes de carbone et d'alcools inférieurs de 1 à 8 atomes de C et/ou des anhydrides des acides alpha, oméga-dicarboxyliques aliphatiques de 2 à 36 atomes de C de préférence avec des acides alpha, oméga-dicarboxyliques aliphatiques de 2 à 36 atomes de C, des esters d'acides alpha, oméga-dicarboxyliques aliphatiques de 2 à 36 atomes de C et des alcools inférieurs de 1 à 8 atomes de C et/ou des anhydrides des acides alpha, oméga-dicarboxyliques aliphatiques de 2 à 36 atomes de C.
- Préparations de filature selon l'une des revendications 1 ou 2, caractérisées en ce que le lubrifiant est un copolyester en masse, le bloc B est constitué deB) diols hydrophobes choisis dans le groupe des polypropylèneglycols d'un poids moléculaire de 400 à 8 000, de polytétrahydrofuranes d'un poids moléculaire de 200 à 8 000, des poly(caprolactone-diols) d'un poids moléculaire de 400 à 4 000, de produits d'hydrogénation des esters d'acide ricinique, de alpha-oméga-alcane-diols aliphatiques de 6 à 22 atomes en C et/ou des diols dimères de 24 à 36 atomes de C.
- Préparations de filature selon l'une des revendications 1 à 3, caractérisées en ce que le lubrifiant est un copolyester en masse, le bloc B) représente :B) des diols hydrophobes choisis dans le groupe des polypropylèneglycols d'un poids moléculaire de 400 à 8 000, des polytétrahydrofuranes d'un poids moléculaire de 200 à 8 000 et notamment des polypropylèneglycols d'un poids moléculaire de 600 à 4 000.
- Préparations de filature selon l'une des revendications 1 à 4, caractérisées en ce que le lubrifiant est un copolyester en masse, préparé à partir de :A) polyéthylèneglycols d'un poids moléculaire de 600 à 3 000, de préférence 800 à 2 000 et,B) de diols hydrophobes choisis dans le groupe des polypropylèneglycols d'un poids moléculaire de 400 à 8 000, de polytétrahydrofuranes d'un poids moléculaire de 200 à 8 000, de poly(caprolactone-diols) d'un poids moléculaire de 400 à 4 000, de produits d'hydrogénation d'esters d'acide ricinique d'alpha, oméga-alcanediols aliphatiques de 2 à 24 atomes de C,et d'acides alpha, oméga-dicarboxyliques aliphatiques reliant les masses A) et B) avec 2 à 36 atomes de C, leurs anhydrides et/ou leurs esters d'alcools inférieurs de 1 à 8 atomes de C.
- Préparations de filature selon la revendication 5, caractérisées en ce que le lubrifiant est un copolyester séquencé, dans lequel :B) on choisit des diols hydrophobes dans le groupe des polypropylèneglycols d'un poids moléculaire de 400 à 8 000 et des polytétrahydrofuranes d'un poids moléculaire de 200 à 8 000, notamment des polypropylèneglycol d'un poids moléculaire de 400 à 8 000.
- Préparations de filature selon l'une des revendications 1 à 6, caractérisées en ce que le lubrifiant est un copolyester en masse qu'on prépare à partir des diols des blocs A) et B) et des acides dicarboxyliques qui les relient, leurs anhydrides, leurs esters d'alcools inférieurs de 1 à 8 atomes de C et/ou les diesters d'acide carbonique d'alcools inférieurs de 1 à 8 atomes de C en une proportion molaire de OH à COOH de 3:1 à 1:3, de préférence de 1,5:1 à 1:1,5 et notamment de 1,2:1 à 0,8:1.
- Préparation de filature selon l'une des revendications 1 à 7, caractérisées en ce que le lubrifiant est un copolyester en masse, préparé à partir des blocs A) et B) en une proportion pondérale de 90:10 à 1:99.
- Préparation de filature selon l'une des revendications 1 à 8, caractérisées en ce que les préparations de filature contiennent des lubrifiants en quantités de 35 à 100 % en poids, dont au moins 50 % en poids sont constitués par le copolyester en masse lubrifiant.
- Utilisation de copolyesters séquencé préparé à partir des blocs :A) polyéthylèneglycols d'un poids moléculaire de 450 à 20 000 et,B) diols hydrophobes choisis dans le groupe des polypropylèneglycols, polytétrahydrofuranes, poly(caprolactonediols), produits d'hydrogénation des esters de l'acide ricinique, 1,2-alcanediols, alpha, oméga-alcane-diols et/ou diols dimères et des acides dicarboxyliques aliphatiques qui relient les blocs A) et B) ayant 2 à 36 atomes de C, leurs anhydrides, leurs esters d'alcools inférieurs de 1 à 8 atomes de C et/ou les diesters d'acide carbonique et d'alcools inférieurs de 1 à 8 atomes de C, comme lubrifiant dans les préparations de filature pour fibres de filament synthétiques.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4107283 | 1991-03-07 | ||
| DE4107283A DE4107283A1 (de) | 1991-03-07 | 1991-03-07 | Spinnpraeparationen fuer synthetische filamentfasern |
| PCT/EP1992/000426 WO1992015749A1 (fr) | 1991-03-07 | 1992-02-27 | Preparations de filature pour fibres en filaments synthetiques |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0574441A1 EP0574441A1 (fr) | 1993-12-22 |
| EP0574441B1 true EP0574441B1 (fr) | 1995-02-01 |
Family
ID=6426677
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP92905481A Expired - Lifetime EP0574441B1 (fr) | 1991-03-07 | 1992-02-27 | Preparations de filature pour fibres en filaments synthetiques |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6204353B1 (fr) |
| EP (1) | EP0574441B1 (fr) |
| JP (1) | JPH06505062A (fr) |
| DE (2) | DE4107283A1 (fr) |
| ES (1) | ES2068029T3 (fr) |
| MX (1) | MX9201011A (fr) |
| TR (1) | TR25819A (fr) |
| WO (1) | WO1992015749A1 (fr) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4202065A1 (de) * | 1992-01-25 | 1993-07-29 | Henkel Kgaa | Verwendung von blockcopolyestern mit polyalkylenglykolbloecken als glaettemittel in spinnpraeparationen |
| DE19525406A1 (de) * | 1995-07-12 | 1997-01-16 | Henkel Kgaa | Herstellung und Verwendung hochviskoser Oligocarbonate aus Dimerdiol |
| WO2000011258A1 (fr) * | 1998-08-18 | 2000-03-02 | Matsumoto Yushi-Seiyaku Co., Ltd. | Composition de traitement de fibres synthetiques presentant une biodegradabilite satisfaisante |
| 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 (fr) * | 1999-07-19 | 2001-01-24 | Clariant International Ltd. | Amélioration de la lubricité au mouillé de matériaux textiles et lubrifiant utilisé dans des opérations au mouillé |
| EP1094147A1 (fr) | 1999-09-22 | 2001-04-25 | Clariant International Ltd. | Amélioration de la capacité de glissement au mouillé de matériaux textiles, et lubrifiant pour traitement au mouillé |
| 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 |
| JP4550816B2 (ja) * | 2003-07-08 | 2010-09-22 | カール・ジェイ・シェイドラー | 織物および皮革の光退色抵抗性および防汚性を改良するための方法および組成物 |
| 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 |
| 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 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA538843A (fr) * | 1957-03-26 | Wyandotte Chemicals Corporation | Melanges de composes nouveaux de polyoxyalkylene | |
| NL136133C (fr) * | 1965-10-21 | |||
| DE1768313B2 (de) | 1968-04-27 | 1977-05-18 | Henkel & Cie GmbH, 4000 Düsseldorf | Verfahren zur herstellung hoehermolekularer mehrwertiger alkohole |
| US3725352A (en) * | 1970-12-30 | 1973-04-03 | Union Carbide Corp | Aba block polymers of polyesters and polyethers |
| GB1455091A (en) | 1974-02-11 | 1976-11-10 | Toyo Boseki | Dispersion of linear polyester resin |
| US4062907A (en) * | 1976-08-25 | 1977-12-13 | Eastman Kodak Company | Polyester hot melt adhesive |
| JPS6028582A (ja) * | 1983-07-25 | 1985-02-13 | 互応化学工業株式会社 | ノリ剤組成物 |
| US4525575A (en) * | 1983-08-05 | 1985-06-25 | Mobay Chemical Corporation | Polyester polyols and mixtures made therefrom |
| JPS626982A (ja) | 1985-07-02 | 1987-01-13 | 松本油脂製薬株式会社 | 繊維処理剤組成物 |
| JPH0643665B2 (ja) | 1987-03-25 | 1994-06-08 | 三洋化成工業株式会社 | 繊維用処理剤 |
| GB8806419D0 (en) * | 1988-03-18 | 1988-04-20 | Du Pont | Improvements relating to fibres |
| JPH0268367A (ja) | 1988-08-30 | 1990-03-07 | Sanyo Chem Ind Ltd | 繊維糸条用ストレート型油剤 |
| DE3830468A1 (de) | 1988-09-08 | 1990-03-15 | Henkel Kgaa | Polyurethanhaltige spinnpraeparationen |
| JPH02120258A (ja) * | 1988-10-28 | 1990-05-08 | Dai Ichi Kogyo Seiyaku Co Ltd | ガラス繊維用集束剤 |
| DE3913145A1 (de) | 1989-04-21 | 1990-10-25 | Basf Ag | Schlichte fuer kohlenstoff-fasern |
-
1991
- 1991-03-07 DE DE4107283A patent/DE4107283A1/de not_active Withdrawn
-
1992
- 1992-02-27 EP EP92905481A patent/EP0574441B1/fr not_active Expired - Lifetime
- 1992-02-27 US US08/117,013 patent/US6204353B1/en not_active Expired - Fee Related
- 1992-02-27 DE DE59201342T patent/DE59201342D1/de not_active Expired - Fee Related
- 1992-02-27 WO PCT/EP1992/000426 patent/WO1992015749A1/fr not_active Ceased
- 1992-02-27 JP JP4504951A patent/JPH06505062A/ja active Pending
- 1992-02-27 ES ES92905481T patent/ES2068029T3/es not_active Expired - Lifetime
- 1992-03-05 TR TR92/0231A patent/TR25819A/xx unknown
- 1992-03-06 MX MX9201011A patent/MX9201011A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPH06505062A (ja) | 1994-06-09 |
| EP0574441A1 (fr) | 1993-12-22 |
| ES2068029T3 (es) | 1995-04-01 |
| US6204353B1 (en) | 2001-03-20 |
| DE59201342D1 (de) | 1995-03-16 |
| DE4107283A1 (de) | 1992-09-10 |
| WO1992015749A1 (fr) | 1992-09-17 |
| TR25819A (tr) | 1993-09-01 |
| MX9201011A (es) | 1992-09-01 |
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