EP0280206A2 - Agent de glissement pour des matériaux textiles fibreux - Google Patents
Agent de glissement pour des matériaux textiles fibreux Download PDFInfo
- Publication number
- EP0280206A2 EP0280206A2 EP88102421A EP88102421A EP0280206A2 EP 0280206 A2 EP0280206 A2 EP 0280206A2 EP 88102421 A EP88102421 A EP 88102421A EP 88102421 A EP88102421 A EP 88102421A EP 0280206 A2 EP0280206 A2 EP 0280206A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- agents
- smoothing
- weight
- fiber materials
- textile
- 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
- 239000004753 textile Substances 0.000 title claims abstract description 33
- 239000000835 fiber Substances 0.000 title claims description 18
- 239000000463 material Substances 0.000 title description 3
- 239000000314 lubricant Substances 0.000 title 1
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 61
- 238000009499 grossing Methods 0.000 claims abstract description 59
- 239000002657 fibrous material Substances 0.000 claims abstract description 21
- 150000001983 dialkylethers Chemical class 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- -1 polyethylenes Polymers 0.000 claims description 28
- 239000006185 dispersion Substances 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 239000004698 Polyethylene Substances 0.000 claims description 14
- 229920000573 polyethylene Polymers 0.000 claims description 14
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 13
- 239000000194 fatty acid Substances 0.000 claims description 13
- 229930195729 fatty acid Natural products 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000002270 dispersing agent Substances 0.000 claims description 7
- 239000004014 plasticizer Substances 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 239000002216 antistatic agent Substances 0.000 claims description 4
- 239000000839 emulsion Substances 0.000 claims description 4
- 239000003205 fragrance Substances 0.000 claims description 4
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 4
- 229920001296 polysiloxane Polymers 0.000 claims description 4
- 239000003755 preservative agent Substances 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 239000003760 tallow Substances 0.000 description 20
- 238000009958 sewing Methods 0.000 description 12
- 150000004665 fatty acids Chemical class 0.000 description 10
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
- 239000004744 fabric Substances 0.000 description 7
- HBXWUCXDUUJDRB-UHFFFAOYSA-N 1-octadecoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCCCC HBXWUCXDUUJDRB-UHFFFAOYSA-N 0.000 description 6
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 5
- 235000010262 sodium metabisulphite Nutrition 0.000 description 5
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 4
- 244000060011 Cocos nucifera Species 0.000 description 4
- 235000013162 Cocos nucifera Nutrition 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000003925 fat Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- SRBSSROHORQGBO-UHFFFAOYSA-N 11-methyldodecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCC(C)C SRBSSROHORQGBO-UHFFFAOYSA-N 0.000 description 3
- 229940013085 2-diethylaminoethanol Drugs 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002926 oxygen Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- UKMSUNONTOPOIO-UHFFFAOYSA-N Behenic acid Natural products CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- GWFGDXZQZYMSMJ-UHFFFAOYSA-N Octadecansaeure-heptadecylester Natural products CCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCCCC GWFGDXZQZYMSMJ-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 150000008051 alkyl sulfates Chemical class 0.000 description 2
- 125000005233 alkylalcohol group Chemical group 0.000 description 2
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940096386 coconut alcohol Drugs 0.000 description 2
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 2
- 229940085632 distearyl ether Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 238000009981 jet dyeing Methods 0.000 description 2
- 238000009940 knitting Methods 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- NKBWPOSQERPBFI-UHFFFAOYSA-N octadecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCCCC NKBWPOSQERPBFI-UHFFFAOYSA-N 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000000985 reactive dye Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000012209 synthetic fiber Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 2
- 238000009941 weaving Methods 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 1
- MMMPXNOKIZOWHM-UHFFFAOYSA-N 1-octoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCC MMMPXNOKIZOWHM-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- ZEYUSQVGRCPBPG-UHFFFAOYSA-N 4,5-dihydroxy-1,3-bis(hydroxymethyl)imidazolidin-2-one Chemical compound OCN1C(O)C(O)N(CO)C1=O ZEYUSQVGRCPBPG-UHFFFAOYSA-N 0.000 description 1
- PBWGCNFJKNQDGV-UHFFFAOYSA-N 6-phenylimidazo[2,1-b][1,3]thiazol-5-amine Chemical compound N1=C2SC=CN2C(N)=C1C1=CC=CC=C1 PBWGCNFJKNQDGV-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VVZBFOKBSDGVGZ-UHFFFAOYSA-N BENZALKONIUM Chemical compound CCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 VVZBFOKBSDGVGZ-UHFFFAOYSA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 229910004879 Na2S2O5 Inorganic materials 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- DMQVGLKQBFOUEQ-UHFFFAOYSA-N S(=O)(=O)(OCC)[O-].C(C)N1C([NH+](CC1)C(C)O)CCCCCCCCCCCCCCCCC Chemical compound S(=O)(=O)(OCC)[O-].C(C)N1C([NH+](CC1)C(C)O)CCCCCCCCCCCCCCCCC DMQVGLKQBFOUEQ-UHFFFAOYSA-N 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 229940090958 behenyl behenate Drugs 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 244000144992 flock Species 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 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
- 239000003921 oil Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl 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])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- CSABAZBYIWDIDE-UHFFFAOYSA-N sulfino hydrogen sulfite Chemical class OS(=O)OS(O)=O CSABAZBYIWDIDE-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000004383 yellowing Methods 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
- D06M15/347—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated ethers, acetals, hemiacetals, ketones or aldehydes
-
- 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
- D06M13/165—Ethers
-
- 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 agents for smoothing textile fiber materials, a method for smoothing textile fiber materials and the use of dialkyl ethers as smoothing agents.
- the smoothing agents used must on the one hand reduce the friction between the individual fibers as well as between fibers or yarns and metal, and on the other hand ensure that fabric can be sewn perfectly. If excessive frictional forces occur during sewing, sewing damage occurs if threads are struck, broken or thermally damaged. The consequence of sewing damage is particularly serious in the case of knitwear, because drop stitches occur at the latest when the goods are mechanically stressed. For this reason, the mobility of the threads in the stitch structure is of great importance.
- the reduction in needles Stitch forces during sewing on modern high-speed sewing machines have become particularly important, since high-speed sewing machines can perform up to 7,000 punctures per minute purely mechanically. However, this requires thicker, more vibration-stable needles, which in turn more easily cause stitch damage.
- Paraffins, esters, polyethylenes, silkones and polyalkylene glycols are known smoothing agents (see, for example, in "Melliand Textile Reports” 3 , 203 to 207 (1977)), the effectiveness of which in many cases depends on the type of fiber substrate.
- From the German patent application DE-OS 32 38 395 polyethylenes with an average molecular weight of 3000 to 8000, a density of 0.94 to 1.01, an acid number of 25 to 60 and a saponification number of 40 to 80 are known as smoothing agents for textile fiber materials .
- the object of the present invention was to develop smoothing agents which, compared to smoothing agents from the prior art, show a significant improvement, i.e. Reduce the friction between individual fibers and between fibers and metal as well as a significant reduction in puncture forces and their effectiveness is independent of the type of fiber substrate.
- alkyl stands for saturated and / or unsaturated alkyl radicals, that is to say for alkyl and / or alkenyl radicals.
- Dialkyl ethers which contain 8 to 22 carbon atoms in the alkyl radicals of natural and / or synthetic origin are preferably present in the smoothing agents according to the invention, for example octyl dodecyl ether, didodecyl ether, tallow stearyl ether, ditalgia, distearyl ether, oleyl stearyl ether and / or 2-hydroxyhexadecyl-talgether.
- Dialkyl ethers having 16 to 18 carbon atoms in the alkyl chains of natural and / or synthetic origin for example ditalgal, distearyl ether, tallow stearyl ether and / or 2-hydroxyhexadecyl tallow, are particularly preferred.
- dialkyl ethers according to the invention are prepared in a manner known per se, for example by reacting alkali metal or ammonium salts of C 6-24 alkyl sulfates with C 6-24 alkyl alcohols at 180 ° C. or the ring having terminally alkoxylated C 6-24 olefins C 6-24 alkyl alcohols, optionally in the presence of a catalyst, is opened at 120-150 ° C.
- Symmetrical and / or asymmetrical dialkyl ethers are used as the only smoothing agent component or in combination with known smoothing agents in smoothing agent mixtures.
- Known smoothing agents are preferably paraffins with softening points between 35 and 80 ° C, polyethylenes, for example anoxidized polyethylene waxes, which are described in DE-OS 32 38 395, fatty acid esters with 8 to 22 carbon atoms in the fat residue and 1 to 22 carbon atoms in the Alcohol residue, for example methyl palmitate, stearyl stearate, behenyl behenate and / or isotridecyl stearate, silicones for example dimethylpolysiloxane and / or polyalkylene glycols, for example polyethylene glycols with average molecular weights from 600 to 2000, are used.
- the weight ratio of dialkyl ether to smoothing agents from the prior art is preferably between 10: 1 and 1: 4, particularly preferably between 4: 1 and
- the smoothing agents according to the invention are applied in the form of solutions, emulsions or dispersions to textile fiber materials.
- the application can be carried out both from water and from organic solvents, for example aliphatic and / or aromatic hydrocarbons, such as gasoline, cyclohexane, toluene, xylene or halogenated, preferably chlorinated hydrocarbons, such as methylene chloride, per-chloroethylene.
- the smoothing agent content in solutions is between 5 and 10 percent by weight, in emulsions and dispesions between 5 and 30 percent by weight.
- the smoothing agents according to the invention are preferably applied in the form of aqueous dispersions to textile fiber materials.
- the term “textile fiber materials” is understood to mean natural fibers, for example cotton, wool and / or cellulose, synthetic fibers, for example polyacrylonitrile, polyester, polyamide, triacetate, polyethylene and / or polypropylene, and mixtures of natural and synthetic fibers.
- the textile fiber materials can be in the form of a flock, sliver, knitting yarn, weaving yarn, sewing thread, knitted fabric, fabric or nonwoven fabric, preferably knitting yarn, weaving yarn, sewing thread, knitted fabric or fabric.
- the material can be raw white, bleached or colored.
- the yarns can be both filament and fiber yarns.
- aqueous dispersions containing the smoothing agents according to the invention are prepared in a manner known per se, either by mixing all the components at from 80 to 170 ° C. or by melting all the components with the exception of water and then water, if appropriate under pressure, at 80 to 170 ° C is added. However, it is also possible to add the melt to hot water at 80 to 100 ° C.
- the resulting finely divided aqueous dispersions have solids contents of 5 to 40 percent by weight and pH values of 3.5 to 11.
- the smoothing agents according to the invention are applied to the textile fiber materials with the aid of conventional apparatus, such as dyeing apparatus for cross-wound bobbins, skeins or muffs, reel runners or jet dyeing systems.
- conventional apparatus such as dyeing apparatus for cross-wound bobbins, skeins or muffs, reel runners or jet dyeing systems.
- the application after an exhaust process for example a drawing process from a dye or rinsing bath, is carried out from an aqueous liquor with a liquor ratio between 1: 2 and 1:40 and a pH value in the liquor between 2 and 8 at temperatures between 25 and 80 ° C and a concentration, based on the weight of the goods, of from 0.2 to 3.0, preferably from 0.2 to 2.5, percent by weight of smoothing agent.
- the smoothing agents according to the invention can also be applied to textile fiber materials by a forced application process, for example padding, immersion centrifugal process, godet application, via metering pump systems as are customary in the production of synthetic filament yarns or by spraying.
- a forced application process for example padding, immersion centrifugal process, godet application, via metering pump systems as are customary in the production of synthetic filament yarns or by spraying.
- the padding process - based on 100% active ingredient content - a concentration of 1 to 50 g / l of liquor, preferably of 5 to 20 g / l of liquor, is used, and at the same time high-finishing agents such as anti-crease or anti-shrinkage finishing agents can be used.
- textile and / or fiber auxiliaries also require further properties: for example, these should lead to little or no yellowing, shear stable, softening, little, if not non-foaming and thermally stable.
- the smoothing agents according to the invention which are preferably in In the form of aqueous dispersions, are mixed with plasticizers and conventional auxiliaries, such as antioxidants, defoamers, stabilizers, antistatic agents, preservatives, pH regulators and / or fragrances, contained in textile and / or fiber auxiliaries.
- Textile and / or fiber auxiliaries containing smoothing agents according to the invention preferably contain 5 to 30 percent by weight of dialkyl ether alone or in combination with paraffins, polyethylenes, fatty acid esters, silicones and / or polyalkylene glycols 1 to 20 weight percent dispersants 0 to 15 weight percent plasticizer 0 to 6% by weight of customary auxiliaries contained in textile and / or fiber auxiliaries, for example antioxidants, defoamers, stabilizers, antistatic agents, preservatives, pH regulators and / or fragrances ad 100 weight percent water.
- customary auxiliaries contained in textile and / or fiber auxiliaries for example antioxidants, defoamers, stabilizers, antistatic agents, preservatives, pH regulators and / or fragrances ad 100 weight percent water.
- the smoothing agents according to the invention can be dispersed in water by methods known per se using nonionic, cationic, anionic and / or amphoteric dispersants.
- Suitable nonionic dispersants are alkoxylated, preferably ethoxylated and / or propoxylated fats, oils, fatty alcohols with 8 to 24 carbon atoms in the fat residue, fatty amines with 8 to 24 carbon atoms in the fat residue and / or C 8-18 alkylphenols, for example castor oil 25 ethylene oxide units, tallow alcohol with 5 ethylene oxide units, tallow alcohol with 20 ethylene oxide units, C 12-18 coco alcohol with 10 ethylene oxide units and / or nonylphenol with 10 ethylene oxide units.
- fatty amines contain 2 to 10 ethylene oxide units.
- Suitable cationic dispersants are alkoxylated, preferably ethoxylated and / or propoxylated, alkylamines having 10 to 22 carbon atoms in the form of their ammonium salts, for example stearylamine with 10 moles of ethylene oxide.
- Suitable anionic dispersants are, for example, alkali and / or ammonium salts of C 6-24 fatty acids, C 8-22 alkyl and / or C 8-22 alkyl ether sulfates, C 8-22 alkyl and / or C 8 22 alkyl benzene sulfonates, C 8-22 alkyl and / or C 8-22 alkyl benzene sulfosuccinates and / or C 8-22 alkyl and / or C 8-22 alkyl ether phosphates.
- suitable amphoteric dispersants are C 8-22- alkyldimethylbetaines, NC 8-22 -alkylamido betaines and / or amphoteric surfactants to be derived from amino acids.
- Fatty acid amidopolyamines which preferably consist of saturated C 16-22 fatty acids or C 16-22 fatty acid mixtures and their esters and polyalkylene polyamines such as diethylene triamine, triethylene tetramine, tetraethylene pentamine or Aminoethylethanolamine can be obtained, the reaction being carried out in such a molar ratio that amine nitrogen atoms capable of salt formation are retained.
- the fatty acid amidopolyamines are in the form of their salts with preferably lower carboxylic acids or hydroxycarboxylic acids with 1 to 4 carbon atoms, for example acetic acid or glycolic acid.
- inorganic acids for example hydrogen halides, such as hydrogen chloride, oxygen acids of phosphorus, such as orthophosphoric acid, phosphoric and hypophosphorous acid, oxygen acids of sulfur, such as sulfuric acid and sulfurous acid, and also boric acid and phosphonic acids are suitable for the formation of fatty acid amidopolyamine salts.
- hydrogen halides such as hydrogen chloride
- oxygen acids of phosphorus such as orthophosphoric acid, phosphoric and hypophosphorous acid
- oxygen acids of sulfur such as sulfuric acid and sulfurous acid
- boric acid and phosphonic acids are suitable for the formation of fatty acid amidopolyamine salts.
- Quaternary ammonium salts such as lauryl trimethyl ammonium chloride and dodecyl benzyl trimethyl ammonium metho are also suitable sulfate, dimethyl-distearylammonium chloride and / or 3-ethyl-1-hydroxyethyl-2-heptadecyl-imidazolinium-ethyl sulfate as a plasticizer in textile and / or fiber auxiliaries containing smoothing agents according to the invention.
- mono- and / or diethanolamides such as tallow fatty acid diethanolamide, can also be present as softening constituents in the smoothing agents according to the invention.
- Textile and / or fiber auxiliaries containing smoothing agents according to the invention contain 0 to 0.5 percent by weight of antioxidants, for example oxygen acids of phosphorus, such as phosphorous and hypophosphorous acid, or alkali disulfites, 0 to 1.0 percent by weight of silicone-based defoamer, 0 to 1, 0% by weight stabilizers, for example starch derivatives and gum arabic, 0 to 5% by weight of antistatic agents, for example alkoxylated, preferably ethoxylated and / or propoxylated, C 6-24 fatty amines, 0 to 0.05% by weight of preservatives, for example formaldehyde, pH regulators, for example C 1-4 -carboxylic acids and / or C 1-4 hydroxycarboxylic acids, such as acetic acid, glycolic acid, alkali hydroxides such as potassium hydroxide and / or amino alcohols such as 2-diethylaminoethanol and / or 0 to 0.1 weight percent of fragrance
- the textile fiber materials treated with the smoothing agents according to the invention regardless of the way in which the smoothing agents are applied to the textile fiber material, have significantly lower friction values and greatly reduced puncture forces.
- the smoothing agents according to the invention have a high thermal stability in the production of high-strength filament yarns and are color-stable and non-volatile under thermal stress, for example when drying or fixing.
- EO means ethylene oxide
- the starting materials listed were heated for 1 hour at 155-160 ° C. with stirring in a cup autoclave. After cooling, 800 g of a finely divided dispersion with a pH of 8.8 were obtained.
- the feed materials were in one simple stirring apparatus melted homogeneously.
- the water likewise heated to 80 ° C., was allowed to flow in over 15 minutes, the mixture was stirred for another 30 minutes and then cooled.
- the fine-particle dispersion had a pH of 5.2.
- 604 g of a finely divided dispersion with a pH of 9.1 were produced from the starting materials by the method described in A.
- Formulations of stable aqueous dispersions F to K which contain smoothing agents from the prior art.
- 100% cotton yarn was dyed on a high temperature short liquor dyeing machine in the form of a press spool.
- the dyeing was carried out with reactive dyes, soaped and aftertreated to improve the wet fastness properties.
- the subsequent smoothing treatment was carried out from a fresh bath in acetic acid medium at a pH of 5.5 for 20 minutes at 50 ° C.
- the aqueous dispersions containing the smoothing agents B and E according to the invention and the known smoothing agents H, I and J were used with a respective Active ingredient requirement of 0.6 percent by weight.
- the yarns were dried on a pressure dryer.
- BW / PES knitwear was dyed with reactive and disperse dyes on a laboratory jet dyeing machine.
- the finish was carried out from a fresh bath at a pH of 6 in 20 minutes at 45 ° C. using aqueous dispersions containing the smoothing agents B or E according to the invention or the known smoothing agents H, I or J, each with an active ingredient coating of 0.5 percent by weight .
- the drying of the product sections was carried out in a tumbler.
- Cotton knitwear was refined on the padder using 50 g / l Flott Stabitex® FRD, Henkel KGaA (dimethyloldihydroxyethylene urea) and 5.0 g / l liquor magnesium chloride as a catalyst. Shock condensation was carried out on the stenter frame at 175 ° C. for 30 seconds. In order to improve the sewing ability and the handling, 50 g / l of each of the aqueous dispersions containing the smoothing agents A, B, C, D or E or the known smoothing agents F, G, H, I, J or K were added to the liquors. The squeeze effect on the foulard was about 80%.
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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT88102421T ATE82779T1 (de) | 1987-02-27 | 1988-02-19 | Glaettemittel fuer textilfasermaterialien. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3706362 | 1987-02-27 | ||
| DE19873706362 DE3706362A1 (de) | 1987-02-27 | 1987-02-27 | Glaettemittel fuer textilfasermaterialien |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0280206A2 true EP0280206A2 (fr) | 1988-08-31 |
| EP0280206A3 EP0280206A3 (fr) | 1990-04-18 |
| EP0280206B1 EP0280206B1 (en) | 1992-11-25 |
Family
ID=6321919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP88102421A Expired - Lifetime EP0280206B1 (en) | 1987-02-27 | 1988-02-19 | Lubricating agent for textile fibre materials |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0280206B1 (fr) |
| JP (1) | JPS63227869A (fr) |
| KR (1) | KR880010181A (fr) |
| AT (1) | ATE82779T1 (fr) |
| BR (1) | BR8800842A (fr) |
| DE (1) | DE3706362A1 (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992019805A1 (fr) * | 1991-05-02 | 1992-11-12 | Henkel Kommanditgesellschaft Auf Aktien | Utilisation de composes speciaux comme agents de lissage dans des huiles de peignage |
| WO1996006971A1 (fr) * | 1994-08-31 | 1996-03-07 | Henkel Corporation | Apprets donnant une grande cohesion aux fibres |
| DE102009054802B4 (de) * | 2009-12-16 | 2017-08-17 | Holmenkol Gmbh | Verwendung von Fettalkoholethern als Gleitmittel für Sportgeräte, Gleitmittelzusammensetzung und Verfahren zur Beschichtung eines Sportgeräts |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007302151A (ja) | 2006-05-12 | 2007-11-22 | Toyoda Gosei Co Ltd | エアバッグ |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2234721A (en) * | 1937-11-26 | 1941-03-11 | Eastman Kodak Co | Yarn treating process and composition therefor |
-
1987
- 1987-02-27 DE DE19873706362 patent/DE3706362A1/de not_active Withdrawn
-
1988
- 1988-02-19 AT AT88102421T patent/ATE82779T1/de active
- 1988-02-19 EP EP88102421A patent/EP0280206B1/de not_active Expired - Lifetime
- 1988-02-26 BR BR8800842A patent/BR8800842A/pt unknown
- 1988-02-27 JP JP63047340A patent/JPS63227869A/ja active Pending
- 1988-02-27 KR KR1019880002045A patent/KR880010181A/ko not_active Withdrawn
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992019805A1 (fr) * | 1991-05-02 | 1992-11-12 | Henkel Kommanditgesellschaft Auf Aktien | Utilisation de composes speciaux comme agents de lissage dans des huiles de peignage |
| US5464660A (en) * | 1991-05-02 | 1995-11-07 | Henkel Kommanditgesellschaft Auf Aktien | Use of special compounds as smoothing agents in combing oils |
| WO1996006971A1 (fr) * | 1994-08-31 | 1996-03-07 | Henkel Corporation | Apprets donnant une grande cohesion aux fibres |
| US5525243A (en) * | 1994-08-31 | 1996-06-11 | Henkel Corporation | High cohesion fiber finishes |
| DE102009054802B4 (de) * | 2009-12-16 | 2017-08-17 | Holmenkol Gmbh | Verwendung von Fettalkoholethern als Gleitmittel für Sportgeräte, Gleitmittelzusammensetzung und Verfahren zur Beschichtung eines Sportgeräts |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE82779T1 (de) | 1992-12-15 |
| KR880010181A (ko) | 1988-10-07 |
| BR8800842A (pt) | 1988-10-04 |
| JPS63227869A (ja) | 1988-09-22 |
| EP0280206A3 (fr) | 1990-04-18 |
| DE3706362A1 (de) | 1988-09-08 |
| EP0280206B1 (en) | 1992-11-25 |
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