US2616869A - Spinning solutions of vinyl chloride polymer in a solvent mixture of tetrahydrofurane and a nitrile - Google Patents

Spinning solutions of vinyl chloride polymer in a solvent mixture of tetrahydrofurane and a nitrile Download PDF

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Publication number
US2616869A
US2616869A US221714A US22171451A US2616869A US 2616869 A US2616869 A US 2616869A US 221714 A US221714 A US 221714A US 22171451 A US22171451 A US 22171451A US 2616869 A US2616869 A US 2616869A
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US
United States
Prior art keywords
tetrahydrofurane
vinyl chloride
solvent
weight
mixture
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
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US221714A
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English (en)
Inventor
Heisenberg Erwin
Kleine Johannes
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Glanzstoff AG
Vereinigte Glanzstoff Fabriken AG
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Glanzstoff AG
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Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00Processes of treating or compounding macromolecular substances
    • C08J3/02Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/09Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
    • C08J3/091Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L27/00Compositions 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 halogen; Compositions of derivatives of such polymers
    • C08L27/02Compositions 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 halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L27/04Compositions 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 halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
    • C08L27/06Homopolymers or copolymers of vinyl chloride
    • DTEXTILES; PAPER
    • D01NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01FCHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/02Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D01F6/08Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds from polymers of halogenated hydrocarbons
    • D01F6/10Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds from polymers of halogenated hydrocarbons from polyvinyl chloride or polyvinylidene chloride
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2327/00Characterised by the use 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 halogen; Derivatives of such polymers
    • C08J2327/02Characterised by the use 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 halogen; Derivatives of such polymers not modified by chemical after-treatment
    • C08J2327/04Characterised by the use 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 halogen; Derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
    • C08J2327/06Homopolymers or copolymers of vinyl chloride

Definitions

  • the present invention relates to liquid compo- 7 Claims. (01. 260-303) sitions of matter, more especially solutions of polymers and/or copolymers of vinyl chloride, M
  • the invention relates further to the production of such compositions and to the production of spun fila ments with the aid thereof.
  • a primary objectof the present invention is the embodiment of spinning solutions which are free of the prior art defects as hereinbefore set erties, and which can be further conditioned to p produce superior textile fibers.”
  • Theseobjects arc 2 achieved in a simple way according to the present invention, which production of good spinning solutions of vinyl chloride polymers and copoly-.- mers from which high quality threads can be spun, by incorporating into the tetrahydrofurane, which is used as solvent, certain quantitles of adipic acid dinitrile. The results thus achieved are surprising because neither tetrahydrofurane nor adipic acid dinitrile by itself gives vinyl chloride polymer solutions which can be satisfactorily spun.
  • adipic acid dinitrile becomes perceptible even on addition of about 10% by weight, relative to the weight of the solvent mixture, and increases with increasing quantity of the addition. The effect begins to diminish only when the adipic acid dinitrile becomes the predominant component of the mixture.
  • a particularly favorable proportion of the two said compounds in the mixture is a proportion of one part by weight of adipic acid dinitrile to four parts by weight of tetrahydrofurane.
  • Such compounds which can be used with tetrahydrofurane as solvents to give vinyl chloride polymer solutions which can be satisfactorily spun according to this invention comprise other nitriles and other chemical compound-s of analogous structure, such for example as:
  • the solvent mixture contains from to 50% by weight of the additional solvent.
  • the upper limit can be exceeded since even then a certain improvement in solubility is obtained.
  • solutions produced according to the invention can be spun without dif culty at room temperature to form artificial threads, artificial bristles and the like, either bythe wet spinning; process or by the dry spinning process.
  • Thesolutions are a s erysu t bleior th producti n of m by cast- 113g,
  • the solutions preferably contain from about to about by weight of polymer.
  • Example 1 100 parts by weight of-polyvinyl chloride are introduced with stirring at 25 C. into a mixture of 100 parts by weight of adipic acid dinitrile and 400 parts by weight of tetrahydroiurane. The mixture is heated slowly to boiling while stirring constantly and, when the polymer has entirely dissolved, is cooled again to room temperature (about 20 C.) The resultant solution can be spun, for example through multiehole stainless steel jets, into water; at .20? C.
  • Example 2 200 parts by weight of polyvinyl chloride are introduced with stirring at 20 C. intoaimixture of 150 parts by weight of glutaric acid dinitrile and 600 parts by weight of tetrahydrofurane. The thus-obtained mixture is heated slowly to boiling with constant stirring and, when dissolution of the polymer is complete, is again cooled at 20 C. The resultant solution can be made up into filaments, threads, bristles, fi1ms ,.etc.
  • Example 3 150 parts by Weight oi polyvinyl chloride are i t u with tirrin at 20C. into a mixture 4 of 150 parts by weight of succinonitrile and 600 parts by weight of tetrahydrofurane. Th thus obtained mixture is heated slowly to boiling with constant stirring and, when dissolution of the polymer is complete, is again cooled at 20 C. The resultant solution can be made up into filaments, threads, bristles, films, etc.
  • Example 4 chloride are introduced into a mixture of parts of vsuccinonitrile and 500 parts by weight of tetrahydrofurane. The mixture is heated, with stirring, untilcomplete solution is achieved, and
  • Example 5 100 parts by weight of polyvinyl chloride are introduced with stirring at 20 G. into a mixture of 60 parts by weight of glutaric acid dinitrile and 600 parts of tetrahydroiurane. The resultant mixture is heated to boiling and, when solution is complete, is cooled back to room temperature. The cooled solution may be used for spinning threads.
  • Example 6 parts by weight of polyvinyl chloride are introduced into a mixture of 300 parts by weight of adiponitrile and 300 parts by weight of tetrahydrofurane, the mixture is then slowly heated to boiling, while constantly stirring, and after solution is complete, the solution is cooled to room temperature. The cooled and filtered solution may be used in the spinning of threads.
  • nitrile succinonitrile, glutaric acid dinitrile, adiponitrile
  • succinonitrile glutaric acid dinitrile, adiponitrile
  • malonitrile fumaric acid dinitrile, diglycolonitrile, or 1,2-dicyanoe-cyclobutane
  • a liquid composition of matter which can be spun to form threads and the like and which can be cast to form films comprising a vinyl chloride polymer as solute in solution in tetrahydrofurane as solvent, said solvent having admixed therewith from about 10% to about 50% by weight of the mixture, of a nitrile which can dissolve polyacrylonitrile completely but which does not by itself give .vinyl chloride polymer solutions. which can be spun.
  • a liquid composition of matter which can be spun to form threads and the like and which can be cast to form films comprising a vinyl chloride polymer. as solutein solution in tetrahydroiurane as solvent said solvent having admixed therewith from about 10% to about 50% by weightof the mixture, of glutaric acid die nitrile.
  • a liquid composition of matter which can be spun to form threads and the like and which can be cast to form films comprising .a vinyl chloride polymer as solute in solution in tetrahydrofurane as. solvent, said solvent havingadmixed therewith, as an additional solvent, a nitrile, the proportion between additional solvent and tetrahydrofurane in the solvent mixture being about 1 :4, by weight.
  • a liquid composition of matter which can be spun to form threads and the like and which can be cast to form films comprising a vinyl chloride polymer as solute in solution in tetrahydrofurane as solvent, said solvent having admixed therewith, as an additional solvent, malonitrile, the proportion between additional solvent and tetrahydrofurane in the solvent mixture being about 1:4 by weight.
  • a liquid composition of matter which can be spun to form threads and the like and which can be cast to form films comprising a vinyl chloride polymer as solute in solution in tetra- 20 cinonitrile, the proportion between additional solvent and tetrahydrofurane in the solvent mixture being about 1:4 by weight.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Dispersion Chemistry (AREA)
  • Artificial Filaments (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US221714A 1949-08-18 1951-04-18 Spinning solutions of vinyl chloride polymer in a solvent mixture of tetrahydrofurane and a nitrile Expired - Lifetime US2616869A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE287831X 1949-08-18

Publications (1)

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US2616869A true US2616869A (en) 1952-11-04

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US221715A Expired - Lifetime US2617777A (en) 1949-08-18 1951-04-18 Solutions of vinyl chloride polymer in a mixture of tetrahydrofurane and a solvent from the group consisting of sulfone, sulfoxides, sulfonic acid esters, and sulfinic acid esters
US221713A Expired - Lifetime US2616868A (en) 1949-08-18 1951-04-18 Spinning solutions of vinyl chloride polymer dissolved in a solvent mixture containing tetrahydrofurane and an additional solvent selected from the group consisting of lactones and lactams
US221714A Expired - Lifetime US2616869A (en) 1949-08-18 1951-04-18 Spinning solutions of vinyl chloride polymer in a solvent mixture of tetrahydrofurane and a nitrile

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US221715A Expired - Lifetime US2617777A (en) 1949-08-18 1951-04-18 Solutions of vinyl chloride polymer in a mixture of tetrahydrofurane and a solvent from the group consisting of sulfone, sulfoxides, sulfonic acid esters, and sulfinic acid esters
US221713A Expired - Lifetime US2616868A (en) 1949-08-18 1951-04-18 Spinning solutions of vinyl chloride polymer dissolved in a solvent mixture containing tetrahydrofurane and an additional solvent selected from the group consisting of lactones and lactams

Country Status (6)

Country Link
US (3) US2617777A (xx)
BE (1) BE497653A (xx)
CH (1) CH287831A (xx)
FR (1) FR1023581A (xx)
GB (1) GB674792A (xx)
NL (3) NL70828C (xx)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3320205A (en) * 1962-07-28 1967-05-16 Kurashiki Rayon Co Method of manufacturing spinning solutions of mixed vinyl chloride and alpha-methylstrene polymers

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE965657C (de) * 1953-08-28 1957-06-13 Basf Ag Loesungsmittel fuer Acetylen
US2756218A (en) * 1953-10-09 1956-07-24 Chemstrand Corp Solutions of acrylonitrile polymers in 1, 5-dimethylpyrrolidone-2
US2906721A (en) * 1956-09-28 1959-09-29 Dow Chemical Co Method for preparing tetrahydrofuran lacquer of wet vinylidene chlorideacrylonitrile copolymer
US2918443A (en) * 1957-01-31 1959-12-22 American Marietta Co Vinyl chloride-vinyl acetate copolymer dissolved in solvent mixture containing aromatic hydrocarbon and pyrrolidone component
US2913430A (en) * 1957-04-09 1959-11-17 American Marietta Co Vinyl chloride-vinyl acetate copolymer dissolved in solvent mixture containing aromatic hydrocarbon and lactone component
US3005739A (en) * 1957-04-29 1961-10-24 Donald D Lang Method and apparatus for making multiconductor cable
US3109828A (en) * 1959-12-30 1963-11-05 Mobil Finishes Company Inc Dimethyl sulfoxide-aromatic hydrocarbon solvent system for vinyl chloride copolymers
US3361697A (en) * 1965-03-24 1968-01-02 Du Pont Plasticized polylactams containing cyclic saturated sulfone
FR2483966A1 (fr) * 1980-06-10 1981-12-11 Rhone Poulenc Textile Solutions conformables a partir de melanges de cellulose et polychlorure de vinyle et articles en forme obtenus
DK153684C (da) * 1982-12-01 1990-02-26 Heimann F & Co As Fremgangsmaade til fremstilling af en limet sammenfoejning mellem overflader af emner fremstillet af i vand uoploeselige, syntetiske, organiske polymerer
US4767808A (en) * 1984-10-05 1988-08-30 Hercon Laboratories Corporation Article useful for administration of pharmacologically-active substances transdermally, orally, or by means of implant
US4687798A (en) * 1986-01-27 1987-08-18 King Lloyd H Sr Solvent cement
FR2638167B1 (fr) * 1988-10-26 1994-07-29 Eternit Financiere Colle pour matieres plastiques et procede de mise en oeuvre de cette colle
US5817708A (en) * 1996-07-19 1998-10-06 The B. F. Goodrich Company Low volatile organic solvent based adhesive
US5821289A (en) * 1996-07-19 1998-10-13 The B.F. Goodrich Company Low volatile organic solvent based adhesive
FR2945040B1 (fr) * 2009-05-04 2011-05-20 Rhodia Operations Procede de preparation des esters d'acides fluoroalcanesulfiniques
WO2016158774A1 (ja) * 2015-03-31 2016-10-06 株式会社カネカ 熱可塑性モダクリル樹脂組成物、その製造方法、その成形体と、アクリル系繊維及びその製造方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2529449A (en) * 1948-02-27 1950-11-07 Monsanto Chemicals Composition comprising polymerized acrylonitrile and solvent therefor

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE443870A (xx) * 1941-06-21

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2529449A (en) * 1948-02-27 1950-11-07 Monsanto Chemicals Composition comprising polymerized acrylonitrile and solvent therefor

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3320205A (en) * 1962-07-28 1967-05-16 Kurashiki Rayon Co Method of manufacturing spinning solutions of mixed vinyl chloride and alpha-methylstrene polymers

Also Published As

Publication number Publication date
US2616868A (en) 1952-11-04
NL71803C (xx)
FR1023581A (fr) 1953-03-20
GB674792A (en) 1952-07-02
US2617777A (en) 1952-11-11
NL72008C (xx)
BE497653A (xx)
NL70828C (xx)
CH287831A (de) 1952-12-31

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