DE1218653B - Manufacture of fibers u. a. made of polyvinyl alcohol and another polymer - Google Patents
Manufacture of fibers u. a. made of polyvinyl alcohol and another polymerInfo
- Publication number
- DE1218653B DE1218653B DEK43488A DEK0043488A DE1218653B DE 1218653 B DE1218653 B DE 1218653B DE K43488 A DEK43488 A DE K43488A DE K0043488 A DEK0043488 A DE K0043488A DE 1218653 B DE1218653 B DE 1218653B
- Authority
- DE
- Germany
- Prior art keywords
- polyvinyl alcohol
- vinyl
- fibers
- threads
- copolymer
- 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.)
- Pending
Links
- 239000004372 Polyvinyl alcohol Substances 0.000 title claims description 19
- 229920002451 polyvinyl alcohol Polymers 0.000 title claims description 19
- 239000000835 fiber Substances 0.000 title claims description 13
- 229920000642 polymer Polymers 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 19
- 229920002554 vinyl polymer Polymers 0.000 claims description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 150000001298 alcohols Chemical class 0.000 claims description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical group OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 4
- 238000000578 dry spinning Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000002166 wet spinning Methods 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 18
- FCYVWWWTHPPJII-UHFFFAOYSA-N 2-methylidenepropanedinitrile Chemical compound N#CC(=C)C#N FCYVWWWTHPPJII-UHFFFAOYSA-N 0.000 description 9
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 8
- 238000006359 acetalization reaction Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- -1 ethylene, propylene Chemical group 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000009987 spinning Methods 0.000 description 3
- 229920001567 vinyl ester resin Polymers 0.000 description 3
- NLXFWUZKOOWWFD-UHFFFAOYSA-N 1-(2-hydroxyethylamino)-4-(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NCCO)=CC=C2NC NLXFWUZKOOWWFD-UHFFFAOYSA-N 0.000 description 2
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 2
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
- LLMLNAVBOAMOEE-UHFFFAOYSA-N 2,3-dichlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1Cl LLMLNAVBOAMOEE-UHFFFAOYSA-N 0.000 description 1
- CKKAXVNHNGRBGL-UHFFFAOYSA-N 2-(cyclohexylamino)butanal Chemical compound C1(CCCCC1)NC(C=O)CC CKKAXVNHNGRBGL-UHFFFAOYSA-N 0.000 description 1
- KZMQZFPRPILIHO-UHFFFAOYSA-N 2-(methylamino)acetaldehyde Chemical compound CNCC=O KZMQZFPRPILIHO-UHFFFAOYSA-N 0.000 description 1
- RQSMGBAUYCTENZ-UHFFFAOYSA-N 2-(nonylamino)acetic acid Chemical compound CCCCCCCCCNCC(O)=O RQSMGBAUYCTENZ-UHFFFAOYSA-N 0.000 description 1
- QLIBJPGWWSHWBF-UHFFFAOYSA-N 2-aminoethyl methacrylate Chemical compound CC(=C)C(=O)OCCN QLIBJPGWWSHWBF-UHFFFAOYSA-N 0.000 description 1
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 1
- SHHKMWMIKILKQW-UHFFFAOYSA-N 2-formylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C=O SHHKMWMIKILKQW-UHFFFAOYSA-N 0.000 description 1
- XFFILAFLGDUMBF-UHFFFAOYSA-N 2-phenoxyacetaldehyde Chemical compound O=CCOC1=CC=CC=C1 XFFILAFLGDUMBF-UHFFFAOYSA-N 0.000 description 1
- WFYXNYMBYDZLLP-UHFFFAOYSA-N 2-prop-2-enylidenepropanedinitrile Chemical compound C=CC=C(C#N)C#N WFYXNYMBYDZLLP-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- MAGFQRLKWCCTQJ-UHFFFAOYSA-N 4-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-N 0.000 description 1
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 1
- VJOWMORERYNYON-UHFFFAOYSA-N 5-ethenyl-2-methylpyridine Chemical compound CC1=CC=C(C=C)C=N1 VJOWMORERYNYON-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- IQFVPQOLBLOTPF-UHFFFAOYSA-L Congo Red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(N=NC3=CC=C(C=C3)C3=CC=C(C=C3)N=NC3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-UHFFFAOYSA-L 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 238000007278 cyanoethylation reaction Methods 0.000 description 1
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- JWAJUTZQGZBKFS-UHFFFAOYSA-N n,n-diethylprop-2-en-1-amine Chemical compound CCN(CC)CC=C JWAJUTZQGZBKFS-UHFFFAOYSA-N 0.000 description 1
- TWJYXMZUQAMMKA-UHFFFAOYSA-N n,n-dimethyl-1-(oxiran-2-yl)methanamine Chemical compound CN(C)CC1CO1 TWJYXMZUQAMMKA-UHFFFAOYSA-N 0.000 description 1
- PWEZHCBZCWLRLV-UHFFFAOYSA-N n-(oxiran-2-ylmethyl)ethanamine Chemical compound CCNCC1CO1 PWEZHCBZCWLRLV-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L29/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical; Compositions of hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Compositions of derivatives of such polymers
- C08L29/02—Homopolymers or copolymers of unsaturated alcohols
- C08L29/04—Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L29/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical; Compositions of hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Compositions of derivatives of such polymers
- C08L29/14—Homopolymers or copolymers of acetals or ketals obtained by polymerisation of unsaturated acetals or ketals or by after-treatment of polymers of unsaturated alcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L31/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid; Compositions of derivatives of such polymers
- C08L31/02—Homopolymers or copolymers of esters of monocarboxylic acids
- C08L31/04—Homopolymers or copolymers of vinyl acetate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L35/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L35/04—Homopolymers or copolymers of nitriles
-
- 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
- D01F6/44—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds
- D01F6/50—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds of polyalcohols, polyacetals or polyketals
Landscapes
- 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)
- Manufacturing & Machinery (AREA)
- General Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Materials Engineering (AREA)
- Artificial Filaments (AREA)
Description
Int. Cl.:Int. Cl .:
DOIfDOIf
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
AUSLEGESCHRIFTEDITORIAL
Deutsche KL: 29 b-3/65German KL: 29 b-3/65
Nummer: 1218 653Number: 1218 653
Aktenzeichen: K 43488IV c/29 bFile number: K 43488IV c / 29 b
Anmeldetag: 18. April 1961 Filing date: April 18, 1961
Auslegetag: 8. Juni 1966Opening day: June 8, 1966
Die aus Polyvinylalkoholderivaten oder aus dem Kopolymerisat von Vinylidencyanid und Vinylacetat gewonnenen Fäden haben folgende Nachteile:Those made from polyvinyl alcohol derivatives or from the copolymer of vinylidenecyanide and vinyl acetate The threads obtained have the following disadvantages:
Die Fasern aus dem Polyvinylalkoholderivat PoIyvinylformal besitzen ausreichende Färbbarkeit und Trockenhitzebeständigkeit, haben jedoch sehr geringe Heißwasserbeständigkeit, so daß sie bis jetzt in der Praxis als Rohmaterial für synthetische Fasern nicht verwendet worden sind.The fibers made from the polyvinyl alcohol derivative polyvinyl formal have sufficient dyeability and dry heat resistance, but are very poor Hot water resistance so that it has not been put into practical use as a raw material for synthetic fibers until now have been used.
Andererseits besitzen die Fäden aus dem Kopolymerisat von Vinylidencyanid und Vinylacetat ausreichende Heißwasserbeständigkeit und Elastizität, haben jedoch eine niedrige Reißfestigkeit und sehr geringe Färbbarkeit.On the other hand, the threads made from the copolymer of vinylidenecyanide and vinyl acetate are sufficient Hot water resistance and elasticity, however, have low tear resistance and very low dyeability.
Erfindungsgegenstand ist ein Verfahren zum Herstellen von Fasern, Fäden oder Folien durch Naß- oder Trockenspinnen von Lösungen, die gelöst in Dimethylsulfoxyd oder Acetonitril und Wasser ein beliebiges Polyvinylalkoholderivat oder ein Vinylalkoholkopolymerisat, das, bezogen auf die Gesamtvinylmonomereinheiten, weniger als 90 Molprozent Vinylalkoholeinheiten besitzt, sowie ein zweites Polymeres enthalten. Das erfindungsgemäße Verfahren ist dadurch gekennzeichnet, daß man Lösungen verspinnt, die als zweites Polymeres Vinylidencyanid-Vinylacetat-Kopolymerisat enthalten.The subject of the invention is a method for producing fibers, threads or films by wet or Dry spinning of solutions dissolved in dimethyl sulfoxide or acetonitrile and any water Polyvinyl alcohol derivative or a vinyl alcohol copolymer which, based on the total vinyl monomer units, has less than 90 mole percent vinyl alcohol units, and contain a second polymer. The inventive method is characterized in that solutions are spun as second polymer vinylidenecyanide-vinyl acetate copolymer contain.
Als Beispiel werden in der folgenden Tabelle die physikalischen Eigenschaften und die Färbbarkeit von Fasern, die einerseits aus jedem selbständigen Material, nämlich aus Polyvinylformal (Formalisierungsgrad 65 Molprozent) und aus dem Kopolymerisat von Vinylidencyanid und Vinylacetat und andererseits aus einer Herstellen von Fasern u. a. aus Polyvinylalkohol und einem weiteren PolymerenAs an example, the following table shows the physical properties and dyeability of Fibers, on the one hand, from any independent material, namely from polyvinyl formal (degree of formalization 65 mol percent) and from the copolymer of vinylidenecyanide and vinyl acetate and on the other hand from a Manufacture of fibers, inter alia. made of polyvinyl alcohol and another polymer
Anmelder:Applicant:
Kurashiki Rayon Company Ltd., Kurashiki (Japan)Kurashiki Rayon Company Ltd., Kurashiki (Japan)
Vertreter:Representative:
Dipl.-Ing. R. Müller-Börner und Dipl.-Ing. H.-H. Wey, Patentanwälte,Dipl.-Ing. R. Müller-Börner and Dipl.-Ing. H.-H. Wey, patent attorneys,
Berlin 33, Podbielskiallee 68 <·Berlin 33, Podbielskiallee 68 <
Als Erfinder benannt:Named as inventor:
Kanji Matsubayashi, Osamu Fukushima, Kurashiki (Japan)Kanji Matsubayashi, Osamu Fukushima, Kurashiki (Japan)
Beanspruchte Priorität: Japan vom 19. April 1960 (21220), vom 8. Dezember 1960 (47 878)Claimed priority: Japan April 19, 1960 (21220), dated December 8, 1960 (47 878)
gemischten Spinnlösung der obengenannten Stoffe hergestellt sind, gezeigt. Dabei bedeutet A eine Polyvinylformalfolie, B eine Faser aus dem Kopolymerisat von Vinylidencyanid und Vinylacetat und C eine Mischfaser nach der Erfindung.mixed dope of the above substances are shown. A denotes a polyvinyl formal film, B a fiber made from the copolymer of vinylidenecyanide and vinyl acetate and C a mixed fiber according to the invention.
Denier denier
Trockenzerreißfestigkeit (g/d) Dry tensile strength (g / d)
Naßzerreißfestigkeit (g/d) Wet tensile strength (g / d)
Trockendehnbarkeit (%) Dry extensibility (%)
Naßdehnbarkeit (%) Wet extensibility (%)
Elastische Nachwirkung 3 °/0 (%) Elastic aftereffect 3 ° / 0 (%)
Elastische Nachwirkung 5°/0 (%) Elastic aftereffect 5 ° / 0 (%)
Erweichungspunkt [trocken] (0C) Softening point [dry] ( 0 C)
Erweichungspunkt [naß] (0C) Softening point [wet] ( 0 C)
Wasseraufnahmefähigkeit (%) Water absorbency (%)
Färbbarkeit (Milligramm Farbstoff je Gramm Faser)Dyeability (milligrams of dye per gram of fiber)
Direktfarbstoff *1) Direct dye * 1)
Dispersfarbstoff *2) Disperse dye * 2)
*]) = Kongorot (C. I. Direct Red 28).* ] ) = Congo Red (CI Direct Red 28).
*2) = Diacelliton Fast Brilliant Blue BF (C. I. Disperse Blue 3).* 2 ) = Diacelliton Fast Brilliant Blue BF (CI Disperse Blue 3).
3,0 3,5 2,03.0 3.5 2.0
55
18055
180
19,0 19,319.0 19.3
3,2 2,3 1,83.2 2.3 1.8
2525th
2828
8282
6565
180180
110110
1,01.0
1,01.0
3,0 3,4 2,63.0 3.4 2.6
2121
2323
8080
70 180 11070 180 110
2525th
19,0 19,019.0 19.0
609 578/512609 578/512
3 43 4
Aus der vorstehenden Tabelle geht klar hervor, daß das Kopolymerisat von Vinylidencyanid und Vinyl-From the table above it is clear that the copolymer of vinylidenecyanide and vinyl
eine Mischfaser aus Polyvinylalkoholderivaten oder acetat (Polymerisationsgrad 1800) wurden in Dime-a mixed fiber made of polyvinyl alcohol derivatives or acetate (degree of polymerization 1800) were
Kopolymerisaten von Vinylalkohol und dem Kopoly- thylsulfoxyd zu einer jeweils 15°/0igen Lösung auf-Kopolymerisaten of vinyl alcohol and the Kopoly- thylsulfoxyd to each 15 ° / 0 solution up
merisat von Vinylidencyanid und Vinylacetat eine gelöst und diese beiden Lösungen zwecks HerstellungMerisat of vinylidenecyanide and vinyl acetate dissolved one and these two solutions for the purpose of production
Reihe von Besonderheiten aufweist. 5 einer gemischten Spinnlösung in einem VerhältnisHas a number of peculiarities. 5 of a mixed dope in a ratio
Als Polyvinylalkoholderivate oder !Copolymerisate von 1:1 gemischt. Diese Lösung wurde durch Spinn-Mixed as polyvinyl alcohol derivatives or copolymers at 1: 1. This solution was made by spinning
von Vinylalkohol, werden erfindungsgemäß verwen- düsen von 0,08 mm Durchmesser in eine 70%igeof vinyl alcohol, nozzles 0.08 mm in diameter are used according to the invention in a 70% strength
det: Acetalisierungsprodukte von Polyvinylalkohol mit wäßrige Dimethylsulfoxydlösung gespritzt. Nachdemdet: Acetalization products of polyvinyl alcohol sprayed with aqueous dimethyl sulfoxide solution. After this
aliphatischen oder aromatischen Aldehyden, wie die Fäden 2 m durch das Fällbad gewandert waren,aliphatic or aromatic aldehydes, as the threads had wandered 2 m through the precipitation bath,
Formaldehyd, Benzaldehyd, Acetaldehyd, Propion- io passierten sie eine wäßrige Lösung von NatriumsulfatFormaldehyde, benzaldehyde, acetaldehyde, propionio they passed through an aqueous solution of sodium sulfate
aldehyd, Butyraldehyd, Octylaldehyd, Nonylaldehyd, (Konzentration 200 g/l) und wurden mit einer Ge-aldehyde, butyraldehyde, octylaldehyde, nonylaldehyde, (concentration 200 g / l) and were
Chlorbenzaldehyd, Dichlorbenzaldehyd, Phenylacet- schwindigkeit von 20 m/Min, aufgespult. Die FädenChlorobenzaldehyde, dichlorobenzaldehyde, phenylacetate speed of 20 m / min, wound on. The strings
aldehyd, Hexahydrobenzaldehyd, Phenoxyacetaldehyd wurden bei 205°C um 500 % heißgestreckt und dannaldehyde, hexahydrobenzaldehyde, phenoxyacetaldehyde were hot stretched 500% at 205 ° C and then
oder Mischacetalisierungsprodukte davon; ferner einer Heißbehandlung in Luft von 210° C bei kon-or mixed acetalization products thereof; furthermore a heat treatment in air at 210 ° C at con-
Cyanoäthylierungsprodukte von Polyvinylalkohol mit 15 stanter Länge unterworfen. Die auf diese Weise ge-Subjected cyanoethylation products of polyvinyl alcohol with 15 constant length. The in this way
Acrylnitril; durch Reaktion von Polyvinylalkohol mit wonnene Faser hatte sehr gute physikalische Eigen-Acrylonitrile; the reaction of polyvinyl alcohol with recovered fibers had very good physical properties
Harnstoff, Phenylisocyanat oder Phenylharnstoff er- schäften und Färbbarkeit.
haltenes Urethan; Ester von Polyvinylalkohol mitUrea, phenyl isocyanate or phenyl urea create and colorability.
retained urethane; Esters of polyvinyl alcohol with
Ameisensäure, Essigsäure oder Benzoesäure; Ver- Beispiel2Formic acid, acetic acid or benzoic acid; Ver Example2
seifungsprodukte von Polyvinylalkoholderivaten, die 20Soap products of polyvinyl alcohol derivatives, the 20th
in Wasser unlöslich und in organischen Lösungsmitteln Polyvinylf ormal (Polymerisationsgrad 2500), dasInsoluble in water and in organic solvents polyvinyl form (degree of polymerisation 2500), the
löslich sind, sowie Acetalisierungsprodukte davon; 0,2% basischen Stickstoff enthielt, der aus Allylaminare soluble, as well as acetalization products thereof; 0.2% basic nitrogen contained that from allylamine
Vinylester und Äthylen, Propylen oder Vinylchlorid mit einem Formalisierungsgrad von 67 MolprozentVinyl ester and ethylene, propylene or vinyl chloride with a degree of formalization of 67 mol percent
und ähnliche !Copolymerisate oder Acetalisierungs- und einem Acetalisierungsgrad von 13 Molprozentand similar copolymers or acetalization and a degree of acetalization of 13 mol percent
produkte davon und ähnliche !Copolymerisate von 25 herrührte, und das Kopolymerisat von Vinylidencyanidproducts thereof and similar copolymers of 25 originated, and the copolymer of vinylidenecyanide
Vinylalkohol. und Vinylacetat (Polymerisationsgrad 2000) wurdenVinyl alcohol. and vinyl acetate (degree of polymerization 2000)
Als Polyvinylalkoholderivate oder Kopolymerisate in einem gemischten Lösungsmittel, das aus 8,5 TeilenAs polyvinyl alcohol derivatives or copolymers in a mixed solvent consisting of 8.5 parts
von Vinylalkohol werden verwendet: die Reaktions- Acetonitril und 1,5 Teilen Wasser bestand, in einemof vinyl alcohol are used: the reaction consisted of acetonitrile and 1.5 parts of water, in one
produkte von Polyvinylalkohol mit Äthylenimin, Verhältnis von 6:4 zu einer 25%igen Lösung auf-products of polyvinyl alcohol with ethylene imine, ratio of 6: 4 to a 25% solution.
l-Dimethylamino-2, 3-epoxypropan oder 1-Methyl- 30 gelöst, wobei so eine gemischte Spinnlösung erhalten1-dimethylamino-2, 3-epoxypropane or 1-methyl-30 dissolved, thus obtaining a mixed spinning solution
äthylamino-2,3-epoxypropan; ferner Aminoacetalisie- wurde. Diese Lösung wurde durch Spinndüsen vonethylamino-2,3-epoxypropane; also Aminoacetalisie- was. This solution was through spinnerets from
rungsprodukte von Polyvinylalkohol mit Aminoacet- 0,2 mm Durchmesser in Luft von 120°C gespritzt undApproximation products of polyvinyl alcohol with aminoacet- 0.2 mm diameter in air at 120 ° C and injected
aldehyd, Methylaminoacetaldehyd, Nonylaminoacet- mit einer Geschwindigkeit von 300 m/Min, in einemaldehyde, methylaminoacetaldehyde, nonylaminoacet- at a speed of 300 m / min, in one
aldehyd, /S-Dimethylaminopropionaldehyd, /3-Amino- Abstand von 5 m unter den Spinndüsen aufgespult,aldehyde, / S-dimethylaminopropionaldehyde, / 3-amino- distance of 5 m under the spinnerets,
butyraldehyd, ^-Dimethylaminobutyraldehyd oder ß- 35 Diese Fäden wurden in Luft bei 200°C um 500%butyraldehyde, ^ -dimethylaminobutyraldehyde or ß- 35 These threads were in air at 200 ° C by 500%
Cyclohexylaminobutyraldehyd; Vinylmonomere wie heißgestreckt. Dann wurden die Fäden einem Heiß-Cyclohexylaminobutyraldehyde; Vinyl monomers such as hot stretched. Then the threads were
Vinylester und Allylamin, Diäthylallylamin, ß-Diäthyl- schrumpfen um 10% in Luft bei 210°C unterworfen,Vinyl ester and allylamine, diethyl allylamine, ß-diethyl shrinkage by 10% in air at 210 ° C,
aminoäthylmethacrylat, 4-Vinylpyridin, 2-Vinylpyridin Die Mischfäden hatten vorzügliche physikalischeaminoethyl methacrylate, 4-vinylpyridine, 2-vinylpyridine The mixed threads had excellent physical properties
oder 2-Methyl-5-vinylpyridin oder deren verseifte Ko- Eigenschaften, wie in der Tabelle angegeben,or 2-methyl-5-vinylpyridine or their saponified co-properties, as indicated in the table,
polymerisate; Quaternisierungsprodukte von Di- 40polymers; Quaternization products from Di- 40
methylsulfatoderÄthylbromidoderAcetalisierungspro- Beispiel 3
dukte davon, oder solche, die basischen Stickstoff fürmethyl sulfate or ethyl bromide or acetalization pro- Example 3
products of it, or those that contain basic nitrogen
das Polymere aufweisen, wobei sie eine Gruppe ent- Polyvinylalkohol (Polymerisationsgrad 2000), derthe polymers, where they have a group ent- Polyvinyl alcohol (degree of polymerisation 2000), the
halten, die in basischen Stickstoff umwandelbar ist, wie bis zu einem Veresterungsgrad von 51 Molprozenthold that is convertible to basic nitrogen, such as up to a degree of esterification of 51 mole percent
zwecksEinführungeinerAminogruppeundgleichzeitiger 45 cyanoäthyliert wurde, und das Kopolymerisat vonwas cyanoethylated for the purpose of introducing an amino group and at the same time 45, and the copolymer of
Verseifung mit flüssigem Ammoniak behandeltes Vinyl- Vinylidencyanid und Vinylacetat wurden zusammenLiquid ammonia saponification treated vinyl vinylidene cyanide and vinyl acetate were combined
acetat und Vinylchlorid. in einem Verhältnis von 3:7 in Dimethylsulfoxyd zuacetate and vinyl chloride. in a ratio of 3: 7 in dimethyl sulfoxide
Als Polyvinylalkoholderivate oder Kopolymerisate einer 15%igen Lösung aufgelöst. Die so erhalteneDissolved as polyvinyl alcohol derivatives or copolymers of a 15% solution. The thus obtained
von Vinylalkohol, die eine Säuregruppe enthalten, gemischte Spinnlösung wurde dann versponnen unddope mixed with vinyl alcohol containing an acid group was then spun and
werden verwendet: die Acetalisierungsprodukte von 50 die gewonnenen Fäden einer Wärmebehandlung ähn-are used: the acetalization products of 50 the threads obtained resemble a heat treatment-
Polyvinylalkohol mit eine Säuregruppe enthaltendem lieh wie im Beispiel 1 unterworfen.
Aldehyd wie a-Sulfoacetaldehyd, /S-SulfobutyraldehydPolyvinyl alcohol with an acid group-containing borrowed as in Example 1 subjected.
Aldehyde such as a-sulfoacetaldehyde, / S-sulfobutyraldehyde
und o-Sulfobenzaldehyd oder Verseifungsprodukte Beispiel4
oder Kopolymerisate von Vinylmonomeren, die eineand o-sulfobenzaldehyde or saponification products Example 4
or copolymers of vinyl monomers, the one
Säuregruppe enthalten, wie Allylsulfonsäure, Vinyl- 55 Polyvinylformal (Polymerisationsgrad 1700) mitAcid group, such as allylsulfonic acid, vinyl 55 polyvinyl formal (degree of polymerization 1700) with
sulfon^äure, p-Styrolsulfonsäure oder Crotonsäure und einem Formalisierungsgrad von 66 Molprozent undsulfonic acid, p-styrenesulfonic acid or crotonic acid and a degree of formalization of 66 mol percent and
Vinylester, oder Acetalisierungsprodukte davon. das Kopolymerisat von Vinylidencyanid und Vinyl-Vinyl esters, or acetalization products thereof. the copolymer of vinylidenecyanide and vinyl
Weiterhin können Polymere verwendet werden, die acetat wurden in Dimethylsulfoxyd zwecks HerstellungPolymers can also be used, the acetate was in dimethyl sulfoxide for the purpose of production
eine Säuregruppe oder eine in eine Säuregruppe um- einer gemischten Spinnlösung in einem Verhältnisan acid group or a mixed spinning solution in an acid group in a ratio
wandelbare Gruppe enthalten, wie mit Alkalien ver- 60 von 1:1 zu einer 15%igen Lösung aufgelöst. Dieseconvertible group, as dissolved with alkalis 60 of 1: 1 to a 15% solution. These
seifte Kopolymerisate von AHylbromid und Vinyl- Lösung wurde durch Spinndüsen von 0,08 mm Durchacetat, die mit Natriumsulfat zwecks Einführung einer messer in eine wäßrige Natriumacetatlösung gespritzt.Soaped copolymers of AHyl bromide and vinyl solution were through spinnerets of 0.08 mm through acetate, injected with sodium sulfate for the purpose of introducing a knife into an aqueous sodium acetate solution.
Sulfongruppe umgesetzt sind. Nachdem die Fäden 3 m des Fällbades passiert hatten,Sulphone group are implemented. After the threads had passed 3 m of the felling bath,
wurden sie mit einer Geschwindigkeit von 7 m/Min.they were at a speed of 7 m / min.
Beispiell 65 aufgespult. Die so erhaltenen Fäden wurden bei 210° CExample 6 5 wound. The threads thus obtained were at 210 ° C
um 800 % heißgestreckt. Bei dieser Art der Faserher-hot stretched by 800%. With this type of fiber
Polyvinylformal (Polymerisationsgrad 2000) mit stellung läßt sich das Lösungsmittel sehr leicht zueinem Formalisierungsgrad von 60 Molprozent und rückgewinnen, auch hat die Mischfaser, die auf diesePolyvinyl formal (degree of polymerization 2000) with position, the solvent can be very easily zueinem Degree of formalization of 60 mole percent and recover, also has the mixed fiber based on this
Weise erhalten wurde, ausgezeichnete physikalische Eigenschaften, wie in der Tabelle gezeigt.Manner was obtained, excellent physical properties, as shown in the table.
Polyvinylbenzal (Polymerisationsgrad 1700) mit einem Benzalisierungsgrad von 25 Molprozent und das Kopolymerisat von Vinylidencyanid und Vinylacetat wurden in Dimethylsulfoxyd jeweils zu einer 15°/0igen Lösung aufgelöst und die beiden Lösungen zur Herstellung einer gemischten Spinnlösung im Verhältnis von 6:4 vermischt. Diese Lösung wurde durch Spinndüsen von 0,08 mm Durchmesser in eine 50%ige Natriumacetatlösung gespritzt. Nachdem die Fäden 3 m des Fällbades passiert hatten, wurden sie mit einer Geschwindigkeit von 10 m/Min, aufgespult. Die so erhaltenen Fäden wurden in Luft von 2100C um 600 % heißgestreckt, wonach sie ähnliche gute physikalische Eigenschaften aufwiesen, wie sie in der Tabelle angegeben sind.Polyvinyl benzal (degree of polymerization 1700) with a benzalation of 25 mole percent and the copolymerizate of vinylidene cyanide and vinyl acetate were each dissolved in dimethylsulfoxide to a 15 ° / 0 solution and the two solutions to prepare a mixed dope in a ratio of 6: mixed. 4 This solution was injected into a 50% sodium acetate solution through spinnerets 0.08 mm in diameter. After the threads had passed 3 m of the felling bath, they were wound up at a speed of 10 m / min. The filaments thus obtained were in the air at 210 0 C hot stretched by 600%, after which they similar good physical properties showed, as given in the table.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2133060 | 1960-04-19 | ||
| JP4787860 | 1960-12-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1218653B true DE1218653B (en) | 1966-06-08 |
Family
ID=26358361
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK43488A Pending DE1218653B (en) | 1960-04-19 | 1961-04-18 | Manufacture of fibers u. a. made of polyvinyl alcohol and another polymer |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1218653B (en) |
| GB (1) | GB910983A (en) |
-
1961
- 1961-04-14 GB GB13481/61A patent/GB910983A/en not_active Expired
- 1961-04-18 DE DEK43488A patent/DE1218653B/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB910983A (en) | 1962-11-21 |
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