EP0587601B1 - Fettsäuremethylester in schmälzmitteln für streichgarnspinnerei - Google Patents
Fettsäuremethylester in schmälzmitteln für streichgarnspinnerei Download PDFInfo
- Publication number
- EP0587601B1 EP0587601B1 EP92910454A EP92910454A EP0587601B1 EP 0587601 B1 EP0587601 B1 EP 0587601B1 EP 92910454 A EP92910454 A EP 92910454A EP 92910454 A EP92910454 A EP 92910454A EP 0587601 B1 EP0587601 B1 EP 0587601B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- weight
- meth
- fatty acid
- acid methyl
- methyl 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.)
- Expired - Lifetime
Links
- 235000019387 fatty acid methyl ester Nutrition 0.000 title claims abstract description 26
- 238000009987 spinning Methods 0.000 title claims abstract description 9
- 239000008041 oiling agent Substances 0.000 title abstract 3
- 239000004753 textile Substances 0.000 claims abstract description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 15
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000314 lubricant Substances 0.000 claims description 44
- 239000000835 fiber Substances 0.000 claims description 33
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 19
- 229920001577 copolymer Polymers 0.000 claims description 19
- 239000000839 emulsion Substances 0.000 claims description 16
- 238000009499 grossing Methods 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 11
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000003995 emulsifying agent Substances 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 7
- 229920001519 homopolymer Polymers 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- 230000001050 lubricating effect Effects 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 22
- -1 fatty acid esters Chemical class 0.000 description 18
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
- 238000003892 spreading Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 210000002268 wool Anatomy 0.000 description 8
- 150000002191 fatty alcohols Chemical class 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000003760 tallow Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- 238000009960 carding Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- OPJWPPVYCOPDCM-UHFFFAOYSA-N 2-ethylhexyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(CC)CCCC OPJWPPVYCOPDCM-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 3
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 3
- 238000007720 emulsion polymerization reaction Methods 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- ORFWYUFLWUWSFM-UHFFFAOYSA-N 2-methylpropyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(C)C ORFWYUFLWUWSFM-UHFFFAOYSA-N 0.000 description 2
- AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 238000003723 Smelting Methods 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229940037626 isobutyl stearate Drugs 0.000 description 2
- CPXCDEMFNPKOEF-UHFFFAOYSA-N methyl 3-methylbenzoate Chemical compound COC(=O)C1=CC=CC(C)=C1 CPXCDEMFNPKOEF-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 238000004804 winding Methods 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- 239000004808 2-ethylhexylester Substances 0.000 description 1
- WAYFJTUZNWOHQH-UHFFFAOYSA-N 2-propylideneoctanoic acid Chemical compound CCCCCCC(C(O)=O)=CCC WAYFJTUZNWOHQH-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- YHCCCMIWRBJYHG-UHFFFAOYSA-N 3-(2-ethylhexoxymethyl)heptane Chemical compound CCCCC(CC)COCC(CC)CCCC YHCCCMIWRBJYHG-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 229920003299 Eltex® Polymers 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 101500021084 Locusta migratoria 5 kDa peptide Proteins 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000004165 Methyl ester of fatty acids Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 239000012935 ammoniumperoxodisulfate Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- NOLXQSVNNIIHMV-UHFFFAOYSA-L disodium;2,2-diethyl-3-hexyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCC(C([O-])=O)(S(O)(=O)=O)C(CC)(CC)C([O-])=O NOLXQSVNNIIHMV-UHFFFAOYSA-L 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000007380 fibre production Methods 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions
Definitions
- the invention relates to the use of C8-C22 fatty acid methyl esters as smoothing agents in lubricants for card spinning in a mixture with homopolymers and / or copolymers of esters of acrylic acid and / or methacrylic acid with intrinsic viscosities [eta] below 400 ml ⁇ g ⁇ 1 in amounts of 0.05 to 10 wt .-% - based on lubricant. Furthermore, the invention relates to a process for the smelting of textile fibers for the production of carded yarns.
- Textile fibers that are processed into carded yarns are subjected to a carding process before spinning.
- the textile fibers are subjected to very high mechanical loads.
- the textile fibers are treated with a lubricant containing smoothing agents before carding.
- Lubricants contain smoothing agents to prevent fiber damage and emulsifiers so that they can be applied as an emulsion, as well as other additives if necessary.
- lubricants with hydrocarbons are used as smoothing agents. Since these smoothing agents are difficult to biodegrade, they are becoming more and more biodegradable smoothing agents for lubricants, for example by fatty acid esters, replaced (Textiltechnik International 1984 (8), 748-758).
- Lubricants with isobutyl stearate or 2-ethylhexyl stearate as smoothing agents are biodegradable, but they have an unsatisfactory spreading capacity on the fiber and therefore no optimal fiber / fiber and fiber / metal friction during the production of carded yarn.
- European patent application EP-A-0 394 802 describes textile lubricants and lubricants which can contain fatty acid methyl esters as smoothing agents. However, the European patent application relates to a method for reducing the viscosity of such lubricants by adding triacetin.
- the object of the invention was therefore to develop a lubricant for carded yarn spinning which, in addition to good biodegradability, has an excellent spreadability on the fiber.
- Another object of the present invention was to provide lubricants based on fatty acid methyl esters with viscosities in the range of the viscosities of mineral oil-based lubricants.
- triglycerides such as the higher viscosity beet oil or polymeric compounds can be used.
- winding oils are known which contain fatty alcohol polymethacrylates to prevent the washing oil from tending to spray off.
- German Offenlegungsschrift DE-A-39 24 160 discloses additives with carboxyl group-free homopolymers and / or copolymers of esters of acrylic acid and / or methacrylic acid with intrinsic viscosities of at least 300, preferably 800 ml g ⁇ 1. Due to their high intrinsic viscosity, these additives are able to improve the thread-pulling and / or the adhesiveness of oils and / or fats.
- the invention accordingly relates to the use of one or more C8 ⁇ 22 fatty acid methyl esters as smoothing agents for carded yarn spinning in a mixture with 0.05 to 10 wt .-% - based on lubricant - the viscosity improver homo- and / or copolymers of esters of acrylic acid and / or methacrylic acid with intrinsic viscosities [eta] below 400 ml g ⁇ 1, measured at 20 ° C. in tetrahydrofuran.
- the fatty acid methyl esters used according to the invention are commercially available products which are usually produced in the presence of acidic catalysts by the esterification of the free fatty acid known per se or by transesterification of fatty acid triglycerides with methanol.
- the resulting methyl esters can be used without further processing, after processing by distillation or after hydrogenation of the unsaturated portions.
- methyl esters of unsaturated and / or saturated fatty acids preferably of fatty acids with 12 to 22 carbon atoms, such as lauric, oleic, stearic, behenyl, linoleic and / or linolenic acid, can be used.
- the fatty acid methyl esters are preferably used in the lubricants for carded yarn production in amounts of 50 to 95, preferably 60 to 90% by weight.
- Another object of the present invention is a process for the smelting of textile fibers for the production of carded yarns, characterized in that the textile fibers are treated with an aqueous emulsion which contains an active substance content - based on the fiber weight - of 1 to 6% by weight of lubricant 60 to 90 wt .-% C8 ⁇ 22 fatty acid methyl ester 5 to 39.95 wt .-% emulsifiers and 0.05 to 10 wt .-% homo- and / or mixed copolymers of esters of Acrylic acid and / or methacrylic acid with intrinsic viscosities [eta] below 400 mg g ⁇ 1, measured at 20 ° C in tetrahydrofuran, and Have 0 to 10 wt .-% additives.
- an aqueous emulsion which contains an active substance content - based on the fiber weight - of 1 to 6% by weight of lubricant 60 to 90 wt .-% C
- the essential monomer building blocks of the polymer compounds provided as viscosity improvers are selected esters of acrylic acid and / or methacrylic acid - hereinafter referred to simply as (meth) acrylates or (meth) acrylic acid esters for the sake of simplicity.
- the alcohol component of these (meth) acrylates is derived from straight-chain and / or branched monofunctional alcohols having 4 to 18 carbon atoms, with those in the C chain range from 6 to 12 being particularly preferred, such as n-butyl (meth) acrylate, n- Hexyl (meth) acrylate, n-decyl (meth) acrylate and / or 2-ethylhexyl (meth) acrylate.
- the polymer compounds can be homopolymers and / or copolymers of the type indicated, conceptually separating two classes in the field of copolymers.
- first class different (meth) acrylates of the specified definition are copolymerized with one another and thus form a copolymer.
- second class copolymers are those with proportions of polymerizable comonomers that are not (meth) acrylates. In the latter case, at most approximately equal proportions of the comonomers are present in the polymer molecule.
- the comonomer content is expediently at most 35% by weight and preferably not more than 25% by weight, in each case based on the monomer mixture.
- Suitable comonomers of the last-mentioned type can, for example, styrene and styrene derivatives such as alkylstyrenes, (meth) acrylates of monofunctional alcohols with less than 4 carbon atoms, acrylonitrile, vinyl esters of aliphatic carboxylic acids such as vinyl acetate and / or vinyl esters of higher aliphatic carboxylic acids with up to 18 carbon atoms. Atoms that are free methacrylic acid or acrylic acid, (meth) acrylic acid amide or other common comonomers.
- Particularly suitable polymers are selected from copolymers of (meth) acrylates, derived from alcohols with 6 to 12 carbon atoms and (meth) acrylic acid, the copolymerization preferably in the weight ratio of (meth) acrylate: (meth) acrylic acid in the range from 85:15 to 98.5: 1.5, or copolymers of (meth) acrylate, derived from alcohols with 6 to 12 carbon atoms, and styrene and (meth) acrylic acid, the copolymers preferably having been prepared in the weight ratio (meth) acrylate: (meth) acrylic acid in the range 85:15 to 98.5: 1.5 and 2 to 25% by weight of the (meth ) Acrylates had been replaced by styrene.
- the polymer compounds are produced in particular by emulsion polymerization in an aqueous medium.
- Preferred working temperatures in the polymerization are in the range from 70 ° C. to 90 ° C.
- the water phase used for the aqueous emulsion polymerization preferably contains surface-active compounds, in particular anionic surfactants, to promote the water solubility of the monomer compounds, which are essentially water-insoluble.
- surface-active compounds in particular anionic surfactants, to promote the water solubility of the monomer compounds, which are essentially water-insoluble.
- the amount of these surfactants can make up, for example, up to 15% by weight, based on the monomer or monomer mixture used, and is advantageously in the range from about 1 to 15% by weight and in particular in the range from about 3 to 10% by weight. %, based in each case on the monomer weight.
- the surface-active compounds can be used in their entirety from the beginning, but they can also, if desired, be added to the aqueous medium in the course of the reaction.
- Suitable anionic surfactants belong, for example, to the classes of alkyl or aryl sulfonates, alkyl or aryl sulfates and ether sulfates. Suitable examples are fatty alcohol sulfates such as sodium lauryl sulfate or corresponding fatty alcohol ether sulfates such as the sodium salt of a C 12/14 fatty alcohol ⁇ 4 EO sulfate.
- Other suitable anionic emulsifiers are alkylbenzene sulfonates, alkylphenol sulfates or alkylphenol ether sulfates.
- emulsifiers are sulfosuccinic acid derivatives, for example dialkyl sulfosuccinates or sulfosuccinates of alkoxylated, in particular ethoxylated, alkanols, especially fatty alcohols.
- Suitable polymerization catalysts are, for example, ammonium persulfate or potassium persulfate. Preferred amounts of the catalyst are in the range from about 0.05 to 0.8% by weight, in particular in the range from about 0.1 to 0.3% by weight, based on the monomers used.
- the polymers are obtained directly as an aqueous emulsion, which can be used in this form in the lubricant.
- the amount of polymer is always based on the active substance content of the polymer in the emulsion if no other information has been given.
- the (meth) acrylate homo- or copolymers must not have too high an intrinsic viscosity, since otherwise a thread tension is observed and such polymers can no longer be emulsified in water.
- the maximum limit of the intrinsic viscosity is 400, preferably 300 and in particular 250 ml g ⁇ 1, measured at 20 ° C in tetrahydrofuran.
- the intrinsic viscosity [eta] should be above 50 and in particular above 150 ml g ⁇ 1, determined according to the method given, so that an increase in viscosity is noticeable in the specified lower amounts.
- the lubricants may contain, as further constituents, emulsifiers, additives such as corrosion inhibitors, antistatic agents, adhesion promoters, bactericides, antioxidants, pH regulators and viscosity improvers.
- Suitable emulsifiers are nonionic, anionic and cationic emulsifiers, for example partial esters of di- and / or triglycerol such as triglycerol monooleate, alkoxylated, preferably ethoxylated and / or propoxylated fats, oils, C8 ⁇ 22 fatty acids, C8 ⁇ 22 fatty alcohols and / or C8 ⁇ 22 fatty acid mono- and / or diethanolamides, such as optionally ethoxylated oleic acid mono- or diethanolamide, alkoxylated, preferably ethoxylated C8 ⁇ 22 fatty acids, the OH group of which is replaced by a C1 ⁇ 4 alkoxy group, alkali and / or ammonium salts of C8 ⁇ 22 alkyl sulfonates, alkali and / or ammonium salts of C8 ⁇ 22 alkyl sulfosuccinates such as sodium dioctyl sul
- the lubricants are prepared in a manner known per se by mixing the specified constituents in the stated amounts at temperatures between 18 and 25 ° C. in any order.
- the polymers are used in the form of their aqueous emulsions, generally as 10 to 40% by weight emulsions of active substance.
- the aqueous emulsion is applied at temperatures between 18 and 25 ° C, preferably by spraying on the textile fibers. It is particularly favorable to allow the emulsion to act on the fibers for 6 to 10 hours before the fibers are carded and spun. Details on the treatment of fibers for the production of carded yarns can be found in the article "New aspects of finishing in the carded yarn spinning mill” by Dr. Veitenhansl et. al. in "textile practice international", August 1984, pages 748 to 758.
- the aqueous emulsion is prepared in a manner known per se by mixing the fatty acid methyl ester-based lubricant with water at temperatures between 18 and 25.degree.
- Textile fibers of natural and / or synthetic origin for example wool, polyester or wool / polyester mixtures, are suitable.
- the optionally dyed textile fibers are present as flakes.
- a fatty acid methyl ester-based lubricant has excellent spreading properties on textile fibers.
- both the friction of individual fibers with one another and the friction between fibers and the metal surfaces are optimal.
- the carded yarns produced have high tensile strength and good uniformity.
- the wool flake was processed in a known manner to Nm 7 carded yarn.
- wool flake was treated with a lubricant which, instead of 70.9% by weight of tallow fatty acid methyl ester and 2.5 g of polymer emulsion, treated with 73.4% by weight stearic acid isobutyl ester or 73.4% by weight stearic acid Contained 2-ethylhexyl ether.
- the electrostatic charge of the treated wool flake was measured at the outlet of the card with a field strength measuring device from Eltex using the induction current method (measuring distance 100 mm).
- the yarn uniformity of the carded yarn was measured using a Uster Tester III from Zellweger-Uster in a standard climate (20 ° C., 65% relative humidity).
- the following can also be used. They provide spreading power and comparable results in the application test.
- the polymers were prepared by placing 690 g of demineralized water, 10 g of diethylhexylsulfosuccinate sodium salt (as a 75% strength aqueous solution) and 0.2 g of ammonium peroxodisulfate in a three-necked flask equipped with a stirrer, reflux condenser, dropping funnel and heating to 80 ° C. 300 g of the monomer mixture according to Table III were added and the mixture was stirred at 80 ° C. for one hour. Finely divided aqueous polymer emulsions were obtained. The intrinsic viscosities of the polymers were determined in tetrahydrofuran at 20 ° C.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Inorganic Fibers (AREA)
- Lubricants (AREA)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4117670 | 1991-05-29 | ||
DE4117670 | 1991-05-29 | ||
DE4201978 | 1992-01-25 | ||
DE4201978A DE4201978A1 (de) | 1991-05-29 | 1992-01-25 | Fettsaeuremethylester in schmaelzmitteln fuer streichgarnspinnerei |
PCT/EP1992/001121 WO1992021809A1 (de) | 1991-05-29 | 1992-05-20 | Fettsäuremethylester in schmälzmitteln für streichgarnspinnerei |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0587601A1 EP0587601A1 (de) | 1994-03-23 |
EP0587601B1 true EP0587601B1 (de) | 1995-07-12 |
Family
ID=25904067
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP92910454A Expired - Lifetime EP0587601B1 (de) | 1991-05-29 | 1992-05-20 | Fettsäuremethylester in schmälzmitteln für streichgarnspinnerei |
Country Status (6)
Country | Link |
---|---|
US (1) | US5439709A (es) |
EP (1) | EP0587601B1 (es) |
AU (1) | AU659841B2 (es) |
DE (2) | DE4201978A1 (es) |
ES (1) | ES2073923T3 (es) |
WO (1) | WO1992021809A1 (es) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19953326B4 (de) * | 1999-06-28 | 2006-11-02 | Industrial Technology Research Institute, Chutung | Biologisch abbaubares Spulöl |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2735151B1 (fr) * | 1995-06-09 | 1997-07-18 | Vetrotex France Sa | Composition d'ensimage pour fils composites et fils composites revetus de cette composition |
US20050020458A1 (en) * | 1998-10-15 | 2005-01-27 | Wolfgang Becker | Lubricants for spinning combed wool slivers and methods of using the same |
DE19847497A1 (de) * | 1998-10-15 | 2000-04-20 | Cognis Deutschland Gmbh | Schmälzmittel für die Kammzugherstellung |
DE10204808A1 (de) * | 2002-02-06 | 2003-08-14 | Cognis Deutschland Gmbh | Verwendung von ethoxylierten Fettsäuren als Glättemittel für synthetische und natürliche Fasern |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0394802A1 (de) * | 1989-04-26 | 1990-10-31 | Henkel Kommanditgesellschaft auf Aktien | Triacetinhaltige textile Gleitmittel |
WO1991008336A1 (de) * | 1989-11-30 | 1991-06-13 | Henkel Kommanditgesellschaft Auf Aktien | Polymerhaltige textile gleitmittel |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2182323A (en) * | 1939-03-04 | 1939-12-05 | Celanese Corp | Treatment of textile materials |
GB571490A (en) * | 1942-10-03 | 1945-08-27 | British Celanese | Improvements in or relating to the lubricating of textiles |
NL140244B (nl) * | 1949-07-27 | Kureha Chemical Ind Co Ltd | Werkwijze voor het stabiliseren van chloorhoudende kunststoffen. | |
BE598467A (es) * | 1959-12-23 | |||
DE1469457A1 (de) * | 1964-04-28 | 1969-01-09 | Procter & Gamble | Textilschmaelze |
US3926816A (en) * | 1970-05-22 | 1975-12-16 | Goulston Co George A | Textile fiber lubricants |
SU705036A1 (ru) * | 1976-03-26 | 1979-12-25 | Предприятие П/Я А-3324 | Замасливатель дл синтетических нитей |
DE2733493C2 (de) * | 1976-05-17 | 1986-11-13 | Henkel KGaA, 4000 Düsseldorf | Glättemittel für Textilfasermaterial |
US4110227A (en) * | 1977-09-19 | 1978-08-29 | Basf Wyandotte Corporation | Oxidation stable polyoxyalkylene fiber lubricants |
US4127490A (en) * | 1977-12-05 | 1978-11-28 | Basf Wyandotte Corporation | Fiber finish compositions |
JPS55128074A (en) * | 1979-03-26 | 1980-10-03 | Matsumoto Yushi Seiyaku Kk | Oil agent composition for synthetic fiber |
JPS58180678A (ja) * | 1982-04-14 | 1983-10-22 | 帝人株式会社 | 合成繊維処理用油剤 |
JPS61126675A (ja) * | 1984-11-22 | 1986-06-14 | Hitachi Ltd | フロツピ−デイスク付crt表示装置 |
JPS6290372A (ja) * | 1985-10-11 | 1987-04-24 | 花王株式会社 | ポリエステル繊維用紡績油剤 |
US4900615A (en) * | 1986-03-11 | 1990-02-13 | Union Oil Company Of California | Textile materials and compositions for use therein |
DE3924160A1 (de) * | 1989-07-21 | 1991-01-24 | Henkel Kgaa | Additiv zur beeinflussung der rheologie von oelen und fetten, seine herstellung und seine verwendung |
JPH0359172A (ja) * | 1989-07-21 | 1991-03-14 | Sanyo Chem Ind Ltd | 水性エマルション型紡糸油剤 |
JP2669559B2 (ja) * | 1989-09-07 | 1997-10-29 | 花王株式会社 | アクリル繊維用紡績油剤 |
DE3936975C1 (en) * | 1989-11-07 | 1991-01-24 | Tudapetrol Mineraloelerzeugnisse Nils Hansen Kg, 2000 Hamburg, De | Spooling oil to treat textured fibres or yarns - comprises vegetable oil, ester of vegetable fatty acid, fatty alcohol polyglycol ether, fatty alcohol methacrylate, etc. |
DE4114240A1 (de) * | 1991-05-02 | 1992-11-05 | Henkel Kgaa | Verwendung von speziellen verbindungen als glaettemittel in kaemmoelen |
-
1992
- 1992-01-25 DE DE4201978A patent/DE4201978A1/de not_active Withdrawn
- 1992-05-20 AU AU17932/92A patent/AU659841B2/en not_active Ceased
- 1992-05-20 EP EP92910454A patent/EP0587601B1/de not_active Expired - Lifetime
- 1992-05-20 US US08/142,451 patent/US5439709A/en not_active Expired - Lifetime
- 1992-05-20 DE DE59202885T patent/DE59202885D1/de not_active Expired - Fee Related
- 1992-05-20 ES ES92910454T patent/ES2073923T3/es not_active Expired - Lifetime
- 1992-05-20 WO PCT/EP1992/001121 patent/WO1992021809A1/de active IP Right Grant
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0394802A1 (de) * | 1989-04-26 | 1990-10-31 | Henkel Kommanditgesellschaft auf Aktien | Triacetinhaltige textile Gleitmittel |
WO1991008336A1 (de) * | 1989-11-30 | 1991-06-13 | Henkel Kommanditgesellschaft Auf Aktien | Polymerhaltige textile gleitmittel |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19953326B4 (de) * | 1999-06-28 | 2006-11-02 | Industrial Technology Research Institute, Chutung | Biologisch abbaubares Spulöl |
Also Published As
Publication number | Publication date |
---|---|
AU659841B2 (en) | 1995-06-01 |
DE4201978A1 (de) | 1992-12-03 |
ES2073923T3 (es) | 1995-08-16 |
US5439709A (en) | 1995-08-08 |
WO1992021809A1 (de) | 1992-12-10 |
EP0587601A1 (de) | 1994-03-23 |
DE59202885D1 (de) | 1995-08-17 |
AU1793292A (en) | 1993-01-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE69821161T2 (de) | Vernetzte Acrylat Copolymere in wässrige Emulsion mit Verdickungs und Suspensionseigenschaften | |
CH605262A5 (es) | ||
DE3305637A1 (de) | Copolymerisate, ihre herstellung und ihre verwendung als hilfsmittel in wasch- und reinigungsmitteln | |
DE69619292T2 (de) | Wasserabweisende Fasern und daraus hergestellte Vliesstoffe | |
DE102012021742A1 (de) | Zusammensetzung zur permanenten Hydrophilierung von Polyolefinfasern und deren Verwendung | |
EP0914513B1 (de) | Verfahren zur hydrophilen ausrüstung von fasern oder vliesstoffen | |
EP0587601B1 (de) | Fettsäuremethylester in schmälzmitteln für streichgarnspinnerei | |
EP0436524B1 (de) | Dispersionen zur ausrüstung von fasermaterialien | |
DE102013113656A1 (de) | Verwendung einer Tensidzusammensetzung zur hydrophilen Ausrüstung von Textilfasern und daraus hergestellten Textilerzeugnissen | |
DE4000304A1 (de) | Polymerhaltige spinnpraeparationen in form waessriger emulsionen oder waessriger loesungen | |
DE69301566T2 (de) | Öliges veredlungsmittel mit hohem schmiermittelanteil | |
DE3939549A1 (de) | Polymerhaltige textile gleitmittel | |
DE1594934C3 (de) | Verfahren zur Herstellung von gebundenen Faservliesen | |
WO1993015257A1 (de) | Verwendung von blockcopolyestern mit polyalkylenglykolblöcken als glättemittel in spinnpräparationen | |
DE2536119A1 (de) | Wasserfreies tiefziehmittel und verfahren zu dessen herstellung | |
DE60101689T3 (de) | Verdickungsmittel für wässrige Systeme | |
EP0230910B2 (de) | Textilbehandlungsmittel | |
EP1119658B1 (de) | Schmälzmittel für die kammzugherstellung | |
DE3325228A1 (de) | Veresterte, oxalkylierte quaternaere ammoniumverbindungen, verfahren zu deren herstellung und deren verwendung als faserpraeparationsmittel | |
EP0502870B1 (de) | Polymerhaltige textile gleitmittel | |
DE2151035A1 (de) | Polymere mit laengerkettigen fluoralkylseitenketten tragenden acrylestermonomereinheiten | |
DE2753646C2 (de) | Schmälzmittelgemische für Textilfasern | |
DE870688C (de) | Verfahren zum Schlichten | |
DE2659705B2 (de) | Präparation für synthetische Fäden und Fasern | |
DE2555896A1 (de) | Sekundaere aetheraminacetate und deren verwendung als praeparationsmittel fuer synthesefasern |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
17P | Request for examination filed |
Effective date: 19931122 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE CH DE ES FR GB IT LI |
|
17Q | First examination report despatched |
Effective date: 19940524 |
|
RBV | Designated contracting states (corrected) |
Designated state(s): DE ES FR GB IT |
|
GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
AK | Designated contracting states |
Kind code of ref document: B1 Designated state(s): DE ES FR GB IT |
|
ET | Fr: translation filed | ||
REG | Reference to a national code |
Ref country code: ES Ref legal event code: FG2A Ref document number: 2073923 Country of ref document: ES Kind code of ref document: T3 |
|
REF | Corresponds to: |
Ref document number: 59202885 Country of ref document: DE Date of ref document: 19950817 |
|
ITF | It: translation for a ep patent filed | ||
GBT | Gb: translation of ep patent filed (gb section 77(6)(a)/1977) |
Effective date: 19951016 |
|
PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |
|
26N | No opposition filed | ||
REG | Reference to a national code |
Ref country code: GB Ref legal event code: IF02 |
|
REG | Reference to a national code |
Ref country code: ES Ref legal event code: PC2A |
|
REG | Reference to a national code |
Ref country code: GB Ref legal event code: 732E |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: TP |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: ES Payment date: 20080619 Year of fee payment: 17 Ref country code: DE Payment date: 20080529 Year of fee payment: 17 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: IT Payment date: 20080528 Year of fee payment: 17 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: GB Payment date: 20080521 Year of fee payment: 17 |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: TP |
|
REG | Reference to a national code |
Ref country code: GB Ref legal event code: 732E Free format text: REGISTERED BETWEEN 20090514 AND 20090520 |
|
GBPC | Gb: european patent ceased through non-payment of renewal fee |
Effective date: 20090520 |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: ST Effective date: 20100129 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: FR Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20090602 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: FR Payment date: 20080514 Year of fee payment: 17 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: GB Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20090520 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: DE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20091201 |
|
REG | Reference to a national code |
Ref country code: ES Ref legal event code: FD2A Effective date: 20090521 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: ES Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20090521 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: IT Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20090520 |