US3554980A - Method for preventing stickiness of fibres consisting of or comprising copolyamide - Google Patents
Method for preventing stickiness of fibres consisting of or comprising copolyamide Download PDFInfo
- Publication number
- US3554980A US3554980A US601757A US60175766A US3554980A US 3554980 A US3554980 A US 3554980A US 601757 A US601757 A US 601757A US 60175766 A US60175766 A US 60175766A US 3554980 A US3554980 A US 3554980A
- Authority
- US
- United States
- Prior art keywords
- acid
- copolyamide
- stickiness
- yarn
- fibres
- 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
- 238000000034 method Methods 0.000 title description 29
- 229910052751 metal Inorganic materials 0.000 abstract description 31
- 239000002184 metal Substances 0.000 abstract description 31
- 239000000203 mixture Substances 0.000 abstract description 17
- 239000004952 Polyamide Substances 0.000 abstract description 14
- 229920002647 polyamide Polymers 0.000 abstract description 14
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract description 8
- 238000006068 polycondensation reaction Methods 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 238000011084 recovery Methods 0.000 abstract description 3
- 150000003839 salts Chemical class 0.000 description 44
- 239000008187 granular material Substances 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000835 fiber Substances 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 8
- 229920006017 homo-polyamide Polymers 0.000 description 8
- 238000009987 spinning Methods 0.000 description 8
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical class 0.000 description 6
- 239000002131 composite material Substances 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 238000002074 melt spinning Methods 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- KTAAUBVMSAZOLC-UHFFFAOYSA-L calcium;hexanedioate Chemical compound [Ca+2].[O-]C(=O)CCCCC([O-])=O KTAAUBVMSAZOLC-UHFFFAOYSA-L 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 description 5
- 239000011261 inert gas Substances 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 229940098697 zinc laurate Drugs 0.000 description 5
- GPYYEEJOMCKTPR-UHFFFAOYSA-L zinc;dodecanoate Chemical compound [Zn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O GPYYEEJOMCKTPR-UHFFFAOYSA-L 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 4
- 235000011037 adipic acid Nutrition 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- -1 aliphatic mono Chemical class 0.000 description 4
- 229910052790 beryllium Inorganic materials 0.000 description 4
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 4
- PZWDHVKNXVLHOV-UHFFFAOYSA-K di(hexadecanoyloxy)alumanyl hexadecanoate Chemical compound [Al+3].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O PZWDHVKNXVLHOV-UHFFFAOYSA-K 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- ZHTQUFVYQREVJP-UHFFFAOYSA-L zinc;hexacosanoate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCCCCCCCCCC([O-])=O ZHTQUFVYQREVJP-UHFFFAOYSA-L 0.000 description 4
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 3
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 3
- 239000008116 calcium stearate Substances 0.000 description 3
- 235000013539 calcium stearate Nutrition 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000004503 fine granule Substances 0.000 description 3
- 239000010419 fine particle Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000004804 winding Methods 0.000 description 3
- RWYRUDPAALLKPX-UHFFFAOYSA-N 2,2-difluoro-n-methylethanamine;hydrochloride Chemical compound Cl.CNCC(F)F RWYRUDPAALLKPX-UHFFFAOYSA-N 0.000 description 2
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 239000001749 Calcium fumarate Substances 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229960002684 aminocaproic acid Drugs 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- AZCXESWAJPYJPO-UHFFFAOYSA-L barium(2+);undec-10-enoate Chemical compound [Ba+2].[O-]C(=O)CCCCCCCCC=C.[O-]C(=O)CCCCCCCCC=C AZCXESWAJPYJPO-UHFFFAOYSA-L 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 235000019296 calcium fumarate Nutrition 0.000 description 2
- 238000010622 cold drawing Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000003951 lactams Chemical class 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- NCRZJKMYPDVONB-UHFFFAOYSA-L magnesium;decanedioate Chemical compound [Mg+2].[O-]C(=O)CCCCCCCCC([O-])=O NCRZJKMYPDVONB-UHFFFAOYSA-L 0.000 description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 238000009877 rendering Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052716 thallium Inorganic materials 0.000 description 2
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- VHOCUJPBKOZGJD-UHFFFAOYSA-N triacontanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O VHOCUJPBKOZGJD-UHFFFAOYSA-N 0.000 description 2
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 description 2
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- VTDMBRAUHKUOON-UHFFFAOYSA-N 4-[(4-carboxyphenyl)methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CC1=CC=C(C(O)=O)C=C1 VTDMBRAUHKUOON-UHFFFAOYSA-N 0.000 description 1
- FITNAOAKVDEJHB-UHFFFAOYSA-N 6-azaniumylhexylazanium;benzene-1,3-dicarboxylate Chemical compound NCCCCCCN.OC(=O)C1=CC=CC(C(O)=O)=C1 FITNAOAKVDEJHB-UHFFFAOYSA-N 0.000 description 1
- XDOLZJYETYVRKV-UHFFFAOYSA-N 7-Aminoheptanoic acid Chemical compound NCCCCCCC(O)=O XDOLZJYETYVRKV-UHFFFAOYSA-N 0.000 description 1
- VWPQCOZMXULHDM-UHFFFAOYSA-N 9-aminononanoic acid Chemical compound NCCCCCCCCC(O)=O VWPQCOZMXULHDM-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 125000003118 aryl group Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000001268 conjugating effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011812 mixed powder Substances 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002683 reaction inhibitor Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/36—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino acids, polyamines and polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/01—Hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F1/00—General methods for the manufacture of artificial filaments or the like
- D01F1/02—Addition of substances to the spinning solution or to the melt
- D01F1/10—Other agents for modifying properties
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/78—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products
- D01F6/80—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products from copolyamides
-
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S524/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S524/921—Elastic memory or heat shrinkable compositions
Definitions
- the present invention relates to a method for preventing stickiness of fibres produced from copolyamides.
- the polyamide fibres have been heretofore used in a Wide field owing to its excellent properties, but most of these fibres have been formed from homopolyamides.
- the homopolyamides have a number of disadvantages in dyeability, hygroscopicity, elastic recovering property etc., so that a large number of copolyamides copolymerized with at least two polyamide forming materials have been proposed in order to improve these disadvantages. It is considered that, in general, the fibres consisting of these copolyamides have excellent properties in dyeability, hygroscopicity, elastic recovering property etc. as compared with homopolyamide fibres and also the shrinking property in hot water is increased, so that they suit for particular uses.
- a large disadvantage to retard practice of the copolyamide fibres consists in an inherent stickiness of the copolyamides, so that in spite of that said fibres have a large number of advantages, these fibres have heretofore not been produced commercially.
- the copolyamides are melt spun and then treated with an oil composition, such as, an aqueous emulsion and thereafter taken up on a bobbin, the fibres stick with each other, so that when said fibres are subjected to next processes, such as, drawing and the other processes an unevenness occurs in yarn tension when unwinding yarn from a bobbin and a uniform treatment can not be eifected and moreover in the worst case, the yarn is broken and the operatability is highly damaged.
- an oil composition such as, an aqueous emulsion and thereafter taken up on a bobbin
- the inventors have made various investigations in order to solve the above described problems resulting in accomplishment of the present invention.
- the object of the present invention is to provide fibre consisting of copolyamide, which has no stickiness without deteriorating the other excellent properties.
- a further object is to provide a method of producing a practical fibre from polyamide having such a high copolymerization ratio that a practical fibre can not be obtained as such due to a high stickiness.
- the other object is to provide polyamide composite filaments having no stickiness but an excellent latent crimpability, which consist of a copolyamide and a homopolyamide.
- the objects above described can be attained by previously mixing homogeneously a small quantity of metal salts of aliphatic mono or dicarboxylic acid to the copolyamide when melt spinning said copolyamide.
- the copolyamides to be applied to the method of the present invention include polyamides obtained by copolycondensating two or more polyamide forming compounds selected from the group consisting of lactams, w-aminocarboxylic acids and salts of diamines and dicarboxylic acids, for example, the polyamide forming materials such as, -y-butyrolactam, o-valerolactarn, e-caprolactam, heptolactam, 6-aminocaproic acid, 7-aminoheptanoic acid, 9 aminononanoic acid, ll-aminoundecanoic acid or salts of diamines, such, as tetramethy lenediamine, pentamethylenediamine, hexamethylenediamine, heptamethylenediamine, octamethylenediamine, nonamethylenediamine, decamethylenediamine, undecamethylenediamine, dodecamethylenediamine, me
- copolyamides involve polyamide copolymers added with inorganic or organic substances of delustrants, pigments, dyestuffs, light stabilizers, heat resistants, antistatic agents and plasticizers.
- the metal salts of aliphatic monoand dicarboxylic acid which may be used for the method according to the invention are aliphatic carboxylic salts in granular form of metals selected from the group consisting of lithium, beryllium, sodium, magnesium, aluminium, potassium, calcium, manganese, nickel, copper, zinc, silver, barium, mercury, thallium, lead, etc. and an aliphatic carboxylic acid forming the salts thereof is mono and dicarboxylic acid having three or more carbon atoms.
- the monocarboxylic acid includes, for example, saturated aliphatic acids such as propionic acid, butylic acid, valeric acid, caproic acid, enanthylic acid, caprylic acid, pelargonic acid, capric acid, undecylic acid, laulic acid, tridecylic acid, myristic acid, pentadecylic acid, palmitic acid, heptadecylic acid, stearic acid, nondecanoic acid, arachic acid, behenic acid, lignoceric acid, cerotic acid, heptacosanoic acid, montanoic acid, nonacosanoic acid, melissylic acid, hentriacontanoic acid, dotriacontanoic acid, tetratriacontanoic acid, ceroplastic acid, hexatriacontanoic acid, octatriacon-tanoic acid, hexatetracont
- metal salts of carboxylic acid having less than 2 carbon atoms to the method according to the invention is not suitable because when said metal salts are mixed to copolyamide before and during the polymerization, said metal salts are disintegrated and act as a chain reaction inhibitor and moreover, when said metal salts are deposited to the fine flake or granules of copolyamide and supplied to a melting device they are also disintegrated to very decrease a stability of the melt viscosity of copolyamide and deteriorate quality of fibres.
- metal salts of aromatic monoand dicarboxylic acids other than those of aliphatic monoor dicarboxylic acid not only some of them act as to vary the viscosity of copolyamide, but also in general the dispersibility thereof in the copolyamide melts is insufficient, so that they are ineffective to prevent a stickiness between fibres of copolyamide and therefore not suitable to be used in the method according to the invention.
- One or more than two of these metal salts of aliphatic carboxylic acid alone or more than two of them are added into starting materials of the copolyamide to effect the polycondensation thereof or these metal salts are added during or after the polycondensation reaction and mixed with agitation, whereby they are very homogeneously dispersed.
- the copolyamide containing the metal salts of aliphatic carboxylic acid in a homogeneous dis persed state is melt spun in a conventional process directly or after moulded into fine granules or fine flakes.
- the metal salts incorporated in the copolyamide in molten state are to be homogeneously dispersed in the copolyamide and it is well effected by a mechanical or physical mixing and dispersing operations such as stirring, shaking, etc., when required.
- the aforesaid operations may be attained by a screw or a pump housed in a melt extruder.
- the content amount of the metal salts to perform the purpose of the invention is preferable within range from 0.03 to 3% by weight based upon the total weight of the copolyamide. In the case of less than 0.03% by weight, the effect for preventing stickiness is insufficient whereas in the case of more than 3% by weight, yarn breakage is developed during the manufacture of fibre and the drawing step and therefore the quality of the fibre is deteriorated.
- the stickiness of the copolyamide may be never developed and moreover the copolymerization ratio which has heretofore been considerably restricted owing to the increase of the stickiness is relatively increased whereby the polyamide fibre free from stickiness while having an extremely high heat shrinking property can be obtained. Furthermore, within the above range of the content an amount of the metal salts, the strength, elongation, dyeability, hygroscopicity, elastic recovering property and the other desired properties are not substantially decreased.
- composite filaments obtained by melting copolyamide containing metal salts of aliphatic carboxylic acid according to the invention and well known homopolyamide separately and by spinning them from the same orifice simultaneously have a good mutually bonding property of the both polymers and also the copolymer does not show any stickiness, the latent crimpability is increased use to the high heat shrinking property and the fibre having extremely excellent crimpability and bulky can be obtained by heat treatment.
- the fibre consisting of the copolyamide melt spun according to the method of the invention can be treated uniformly and easily in a treatment with an oil composition, taking up, drawing after spinning and the succeeding knitting and weaving processes without accompanying any disadvantage such as, bad unwinding from a bobbin or stickiness between fibres as in a conventional homopolyamide fibre and furthermore the treatment velocity can be further increased.
- the fibres obtained by the method of the invention are provided with the excellent properties as described above which have never been seen in conventional homopolyamide fibres, so that they are preferable as raw material for producing various clothings, interior decorations, commercial articles, etc. by using solely or in combination with the other fibres.
- said fibres are mix-spun or mix-woven with the other fibres and then subjected to heat treatment by utilizing the high shrinking property, interesting fancy yarns or fancy fabrics can be manufactured.
- FIG. 1 is a graph showing a resistance of a well known and drawn copolyamide yarn in unwinding it from a bobbin;
- FIG. 2 is a graph showing a resistance of the undrawn copolyamide yarn improved by the method according to the invention in unwinding it from a bobbin.
- EXAMPLE 1 To e-caprolactam was added 10% by weight of salt of N,N'-bis(w-aminopropyl)piperazine with adipic acid, 19. mol of acetic acid as a viscosity regulator and further 0.5% by weight of calcium stearate and the resulting mixture was heated with agitation in the nitrogen gas atmosphere at 250 C. for 7 hours under a normal pressure to conduct copolycondensation, whereafter the reacted product was extruded from bottom of a reactor in the form of strip to permit passing through water bath so as to be cooled and solidified, which was then cut into copolyamide fine granules of 3 mm X 3 mm.
- the thusly obtained fine granules were washed with hot water of approximately C. to remove monomer therefrom and dried by a vacuum drier at 80 C. under 0.1 mm. Hg to reduce the water content to 0.065% and whereafter supplied to a heat grid type of melt-spinning device. After residence for 40 rnlnutes, the copolymer melted at 270 C., was extruded from nozzles and applied with the spinning oil composition consisting of an aqueous emulsion by means of the rotary roller and then taken up on a bobbin as an undrawn yarn having 412 d./ 28 filaments.
- the resulting two yarns were determined with respect to stickiness degree by the following means. That is, a bobbin was arranged at right angle to the bottom thereof. A tension meter (TI-80 type made by Toyo Sokki Co.) was located at a position right above the bobbin and separated from it 90 cm. along the extension line of the bobbin axis.
- a tension meter TI-80 type made by Toyo Sokki Co.
- a guide was secured to a point separated 12 cm. from the tension meter along a line inclined by 20 from the bobbin axis.
- a winding machine was arranged at a position located horizontally with respect to the guide.
- the yarn unwound from the bobbin was passed through the tension meter and taken up by the winder through the guide.
- the unwinding resistance of the yarn perceived on the tension meter was recorded on a chart by means of a pen writing recorder (WTR-211 type made by Watanabe Sokki Co.).
- the take-up velocity was 100 m./ min. and the graduation of 1 cm. in the chart to record the unwinding resistance of yarn was adjusted so as to correspond to a resistance of 5 g. load.
- FIG. 1 is a diagrammatical view of a control yarn containing no calcium stearate, which shows a stickiness corresponding to to 12 g.
- FIG. 2 illustrates a resistance of the sample used in the method according to the invention which exhibits the-resistance of only 2 to 3 g.
- copolyamide fine granule which was not applied with aluminium palmitate, was treated in the same manner as described above to take up undrawn yarn having the same denier on a bobbin, which was a control yarn.
- the stickiness degree of the samples was 7 measured by the method according to Example 1, and as the result the control yarn showed an unwinding resistance of 8 to 9 g., whereas the sample containing aluminium palmitate recorded to resistance of only 1 to 2 g.
- the drawing operation at a high speed became impossible owing to the high stickiness of the control yarn, so that the winding rate was reduced to 50 m./rnin. to continue the cold drawings.
- comparative tests of the samples of the both 40 d./7 filaments were made with respect to the yarn properties such as dyeability, hygroscopicity, shrinkability, elastic recovering properties, etc. and the both yarns exhibited the same value and no influence due to an appli cation of aluminium palmitate was perceived.
- EXAMPLE 3 To the salt of undecamethylenediamine and terephthalic acid were added 20% by weight of salt of paraxylylenediamine and adipic acid, 0.3% by weight of titanium oxide, mol of hexamethylenediamine based upon the total amount of the starting material of the polycondensation as a viscosity regulator and further 1% by weight of zinc cerotate. The resulting mixture was heated at 295 C. under an inert gas and polymerized with agitation for 6 hours and then processed into the fine particles of 3 mm x 3 mm., washed with water and dried by the conventional process.
- the resulting fine particles were fed into a melt extruder (YE4NT type manufactured by Yamakawa Tekko Seisakusho) to spin denier monofilament and furthermore the fine granules free from zinc cerotate were prepared and spun under the exactly same condition.
- a melt extruder Yamakawa Tekko Seisakusho
- the resulting two 80 denier filaments were determined in respect of each stickiness degree according to the method as mentioned in Example 1 and as the result, the control yarn free from zinc cerotate suflfered the frequent yarn breakages during the determination owing to its high stickiness degree resulting in rendering the determination impossible, while the yarn containing zinc cerotate exhibited an unwinding resistance of only 2 to 3 g.
- EXAMPLE 4 To the salt of hexamethylene diamine and isophthalic acid were added 8% by weight of salt of paraxylylenediamine and dodecandicarboxylic and M mol of acetic acid as a viscosity regulator, 0.3% by weight of titanium oxide and further 0.8% by weight of zinc laurate and the resulting mixture was heated to 260 C. in the presence of an inert gas, stirred for 7 hours to effect the polymerization, processed into the fine granules of 3 mmqb x 3 mm.
- copolyamide fine granules free from zinc laurate were prepared and spun under the exactly same condition.
- the resulting two yarns were determined in respect of each stickiness degree according to the method as mentioned in Example 1 and as the result the control yarn free from zinc laurate showed the unwinding resistance of 6 to 8 g., while the yarn containing zinc laurate exhibited the unwinding resistance of only 1 to 2 g. and a remarkable eifect of preventing the stickiness due to an application of zinc laurate was perceived. Furthermore, these two yarns were determined in respect of an amount of spinning oil composition deposited thereto by the ether extraction process as the result, both yarns showed the same amount.
- EXAMPLE 5 To s-caprolactam, were added 10% by weight of salt of bis('y-aminopropyl)ether and terephthalic acid, 1 mol of acetic acid as a viscosity regulator and further 0.5% by weight of calcium adipate and the resulting mixture was heated to 250 C., in the presence of an inert gas, stirred for 7 hours to effect the polymerization and processed into the copolyamide fine granules of 3 mm x 3 mm. Moreover, the copolyamide fine granules free from calcium adipate were prepared under the same condition.
- the thusly obtained two filaments were determined in respect of each stickiness according to the method as mentioned in Example 1 and as the result, the filament free from calcium adipate showed the unwinding resistance of 2 to 3 g., while the filament containing calcium adipate exhibited that of only 0.5 to 1 g. Furthermore, the two samples were subjected to the drawing process in which the filaments free from calcium adipate suffered the frequent breakages owing to its high stickiness. The resultant two drawn filaments were determined comparatively in respect of the yarn properties and crimpability, but no substantial difference was perceived.
- EXAMPLE 6 To e-caprolactam were added 12% by weight of salt consisting of hexamethylenediamine and isophthalic acid and mol of acetic acid as a viscosity regulator, which was further added or not added with 1% by weight of beryllium propionate, 1% by weight of barium undecylenate, 1% by weight of zinc melissate, 1% by weight of magnesium sebacate and 1% by weight of calcium fumarate. The resulting six starting materials of polymerization were heated respectively to 250 C. in the presence of an inert gas stirred to 7 hours to effect polymerization, processed into copolyamide fine granules of 2 mm x 2. mm., washed with water and dried in the conventional process. The thusly obtained fine granules were fed into a melt spinning apparatus to form the yarn having 268 d./ 18 filaments.
- the resultant six bobbin filaments were determined in respect of respective stickiness according to the method as mentioned in Example 1 and as the result, the sample filament free from metal salt suffered the yarn breakage simultaneous with the starting of a winding device arranged in a measuring apparatus owing to its violent stickiness, resulting in rendering the determination impossible.
- the sample containing beryllium propionate exhibited the unwinding resistance of 2 to 3 g., that containing barium undecylenate showed 2 to 3 g., that containing zinc melissate showed 1 to 2 g., that containing magnesium sebacate showed 3 to 4 g. and that containing calcium fumarate recorded the unwinding resistance of 1 to 2 g.
- a copolyamide composition of improved elastic recovery properties, dyability, resistance to stickiness and hydroscopicity consisting essentially of a copolyamide which is a polycondensation product of at least two polyamide forming compounds selected from the group consisting of lactams, omegaamino carboxylic acids and salts of diamines with dicarboxylic acids; and incorporated homogeneously in said copolyamide 0.03 to 3% by weight, based on the copolyamide, of at least one metal salt selected from the group consisting of metal salts of aliphatic mono and di-carboxylic acids, having three or more carbon atoms.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Artificial Filaments (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Nonwoven Fabrics (AREA)
- Yarns And Mechanical Finishing Of Yarns Or Ropes (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US798208*A US3574047A (en) | 1965-12-23 | 1968-09-03 | Composite filament having reduced stickiness |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP7972565 | 1965-12-23 | ||
JP7972465 | 1965-12-23 | ||
JP7972665 | 1965-12-23 | ||
JP3556966 | 1966-06-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3554980A true US3554980A (en) | 1971-01-12 |
Family
ID=27460110
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US601757A Expired - Lifetime US3554980A (en) | 1965-12-23 | 1966-12-14 | Method for preventing stickiness of fibres consisting of or comprising copolyamide |
Country Status (8)
Country | Link |
---|---|
US (1) | US3554980A (xx) |
BE (1) | BE691700A (xx) |
DE (2) | DE1669477A1 (xx) |
ES (1) | ES334835A1 (xx) |
FR (1) | FR1514205A (xx) |
GB (3) | GB1127479A (xx) |
NL (3) | NL157631B (xx) |
SE (1) | SE328957B (xx) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3667207A (en) * | 1970-05-01 | 1972-06-06 | Du Pont | Crimpable composite polyamide yarn |
US3846357A (en) * | 1971-10-21 | 1974-11-05 | Aquitaine Total Organico | Process for the polymerization of lactames allowing substances affected by high temperatures to be added during polymerization |
US3915912A (en) * | 1970-03-05 | 1975-10-28 | Asahi Chemical Ind | Modified polyamide compositions containing a polyethylene glycol derivative and a fatty acid or fatty acid salt |
US4379256A (en) * | 1979-09-21 | 1983-04-05 | Compagnie Internationale Pour L'informatique Cii Honeywell Bull | Apparatus and method for measuring the speed of a movable system with respect to a data carrier |
US4383207A (en) * | 1979-09-21 | 1983-05-10 | Cii-Honeywell Bull | Apparatus and method for displacing movable system with respect to a data carrier |
US20040249099A1 (en) * | 1996-03-26 | 2004-12-09 | Chemence, Inc. | Acrylic esters of 2-cyano-2, 4 pentenedioic acid |
US11230808B2 (en) * | 2018-06-21 | 2022-01-25 | Heimbach Gmbh | Clothing for paper machines or pulp dewatering machines and the use of such a clothing |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3726945A (en) * | 1972-02-11 | 1973-04-10 | Bayer Ag | Homogeneous mixtures of polyamides and hydroxyl-containing polyolefines |
IT1170091B (it) * | 1983-12-30 | 1987-06-03 | Snia Fibre | Procedimento per la filatura di materiali polimerici termoplastici per fusione di fibre sintetiche, fibre e manufatti relativi |
DE69032154T2 (de) * | 1989-12-22 | 1998-07-02 | Nippon Oils & Fats Co Ltd | Mittel zur Verbesserung des Schiebewiderstandes |
DE19622027C1 (de) * | 1996-05-31 | 1997-07-31 | Inventa Ag | Hochschrumpfende PA-Fasern und -Garne und Verfahren zu ihrer Herstellung sowie deren Verwendung |
WO2020018608A1 (en) * | 2018-07-18 | 2020-01-23 | Invista North America S.A R.L. | A modified polyamide fiber and articles made thereof |
-
1966
- 1966-12-14 US US601757A patent/US3554980A/en not_active Expired - Lifetime
- 1966-12-19 SE SE17342/66A patent/SE328957B/xx unknown
- 1966-12-22 GB GB57515/66A patent/GB1127479A/en not_active Expired
- 1966-12-22 GB GB57516/66A patent/GB1136173A/en not_active Expired
- 1966-12-22 ES ES334835A patent/ES334835A1/es not_active Expired
- 1966-12-22 DE DE19661669477 patent/DE1669477A1/de active Pending
- 1966-12-22 DE DE19661669478 patent/DE1669478A1/de not_active Withdrawn
- 1966-12-22 GB GB57517/66A patent/GB1138520A/en not_active Expired
- 1966-12-23 NL NL6618085.A patent/NL157631B/xx unknown
- 1966-12-23 NL NL6618086A patent/NL6618086A/xx unknown
- 1966-12-23 BE BE691700D patent/BE691700A/xx unknown
- 1966-12-23 NL NL6618087A patent/NL6618087A/xx unknown
- 1966-12-23 FR FR88741A patent/FR1514205A/fr not_active Expired
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3915912A (en) * | 1970-03-05 | 1975-10-28 | Asahi Chemical Ind | Modified polyamide compositions containing a polyethylene glycol derivative and a fatty acid or fatty acid salt |
US3667207A (en) * | 1970-05-01 | 1972-06-06 | Du Pont | Crimpable composite polyamide yarn |
US3846357A (en) * | 1971-10-21 | 1974-11-05 | Aquitaine Total Organico | Process for the polymerization of lactames allowing substances affected by high temperatures to be added during polymerization |
US4379256A (en) * | 1979-09-21 | 1983-04-05 | Compagnie Internationale Pour L'informatique Cii Honeywell Bull | Apparatus and method for measuring the speed of a movable system with respect to a data carrier |
US4383207A (en) * | 1979-09-21 | 1983-05-10 | Cii-Honeywell Bull | Apparatus and method for displacing movable system with respect to a data carrier |
US20040249099A1 (en) * | 1996-03-26 | 2004-12-09 | Chemence, Inc. | Acrylic esters of 2-cyano-2, 4 pentenedioic acid |
US11230808B2 (en) * | 2018-06-21 | 2022-01-25 | Heimbach Gmbh | Clothing for paper machines or pulp dewatering machines and the use of such a clothing |
Also Published As
Publication number | Publication date |
---|---|
BE691700A (xx) | 1967-05-29 |
DE1669476A1 (de) | 1970-12-23 |
GB1138520A (en) | 1969-01-01 |
DE1669478A1 (de) | 1970-10-29 |
NL6618086A (xx) | 1967-06-26 |
NL6618087A (xx) | 1967-06-26 |
ES334835A1 (es) | 1968-04-16 |
NL157631B (nl) | 1978-08-15 |
GB1127479A (en) | 1968-09-18 |
NL6618085A (xx) | 1967-06-26 |
SE328957B (xx) | 1970-09-28 |
GB1136173A (en) | 1968-12-11 |
FR1514205A (fr) | 1968-02-23 |
DE1669477A1 (de) | 1970-12-17 |
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