US2616868A - 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 - Google Patents

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 Download PDF

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Publication number
US2616868A
US2616868A US221713A US22171351A US2616868A US 2616868 A US2616868 A US 2616868A US 221713 A US221713 A US 221713A US 22171351 A US22171351 A US 22171351A US 2616868 A US2616868 A US 2616868A
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United States
Prior art keywords
vinyl chloride
tetrahydrofurane
solvent
weight
chloride polymer
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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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US221713A
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English (en)
Inventor
Heisenberg Erwin
Kleine Johannes
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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 compositions of matter, more especially solutions of polymers and/or copolymers of vinyl chloride, which can be spun to form threads and the like and which can be cast to form films.
  • the invention relates further to the production of such compositions and to the production of spun filaments with the aid thereof.
  • a primary object of the present invention is the embodiment of spinning solutions which are free of the prior art defects as hereinbefore set forth.
  • a further object of the invention is the preparation of spun polymeric or copolymeric vinyl chloride filaments of improved physical properties and manifestly superior textile properties, and which can be further conditioned to produce superiortextile-fibers.”
  • admixture with tetrahydrofurane ac cording to the invention produces a fundamental change not only in the solvent power of butyrolactone but also in the solvent power of other solvents which have previously been proposed for polyacrylonitrile but which by themselves cannot be used to give vinyl chloride polymer solutions which can be satisfactorily spun.
  • 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 lactones as well as lactams and other chemical compounds of analogous structure, such for example as:
  • the solvent mixture contains from 10 to 50% by weight of the additional solvent.
  • the upper limit can be exceeded since even then a certain improvement in solubility is obtained.
  • the favorable 'eiieets in improving the solubility with the solven mixtur ll g a c to the invention are obtained not only with polyvinyl chloride but also with copolyrners oi vinyl chloride, ior example vinyl chloride-vinyl aceat e p y ers, v nyl ch qride-vi y dene chloride copoylmers, vinyl chloride-styrene copolymere, vinyl chloride-vinyl acetate-vinylidcne ide enql mers e et
  • One of the most important advantages of solutions produced according to the invention is that the solutions can bespujn' without difiiculty at room temperature to form artificial threads, artificial bristles and the like, i'therby the wet spinning process 'o'r'by thedr'y spinning process.
  • sxampleurtificial threads are ob taine d with a strengthoff 215 to 3 "grams/denier and extensions of "-25%.
  • the solutions are also very suitable for the production of films by casting;
  • the s'olutions preferably contain from about 15 to about 25% by weight of polymer.
  • Example l 210 parts by weight of polyvinyl chloride are introduced with stirring at G. into a mixture of l50 parts by'wei'ght of butyrolactone and 500 parts by weight of tetr'ahydrofurane. The mixture is heated to boiling while stirring and, when solution is complete, is cooled to 20? C... The resultant solution can be spun, for example, through multi-hole stainless steel jets, into water at 209 ,r
  • Example 3 100 parts by weight of polyvinyl chloride are introduced with stirring at C. into a mixture of 100 parts by weight of N-methylpyrrolidone and 400 parts by weight :of tetrahydrofurane. The mixture is heated to boiling and then cooled again to room temperature (about 20 0.). The resulting solution can be spun into water. at 20". C.
  • Example 3 100 parts by weight of, polyvinyl chloride are introduced with stirring at 25 C. into a mixture of 80 parts by weight of glycol carbonate and 400 parts by weight of tetrahydrofurane, the mixture heated to boiling in the course of 36. minutes and, when complete solution has taken place, cooled again to 20 Q. The resultant 50- 4 lution is then ready for spinning or casting, after le-f n t e dete t ii eemi
  • Example 4 parts by weight of a copolymer from equimolecular" amounts of vinyl chloride and acrylonitrile are introduced with stirring at 25 C. into a mixture of 80 parts by weight of butyrolactone and 420 parts by weight of tetrahydrofurane. The mixture is brought to boiling in the'cou'rse' of 45 minutes and, when solution is complete, is cooled to about 20 C. The product is then ready for use in preparing threads, films,
  • butyrolactone may with equivalent results be replaced, in this example, by an equivalent quantity or e-caprolactam, N-isopropyl-pyrrolidone or ycaprolactone, while otherwise proceeding as described.
  • En emble 5 parts y wei ht of polyvinyl hloride are introduced with stirring at :20? G. into a mixture of 50 parts y w i ht of u yr la to e and .500 parts by wei ht of tet ah dro urane. the mixt r heated in order to e e solution and, when lu ion is complete, eoo edaga n t 2.0? C. The resultant solution is then ready .1. spinning or casting.
  • the butyro ct ne may with equ valent r s t be replaced, in this exam le. by an equivalen quantity o e-c prolaet m N-ie propyl-pyrolidone or y-eapr act ne While, other-w s eceeding as described.
  • Example '6 120 parts by weight oi polyvinyl chloride are introduced with stirring at zll" into a mixture of parts by weight'ot butyrolactone and'375 parts by weight of tetrahydrofurangthemix ture heated to effect solution and, when solution is complete, cooled again to 20 C, The resultant solution is' then ready spinning or casting.
  • 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 tetrahydr'o'furane as solvent, said solvent having admixed therewith irom about 10% to about 50% by weight of the mixture, of an additional'solvent selected .from the group consisting of lactones and la'ctams which can dissolve polyacrylonitrile completely but whioh'do not by themselves give vinyl chloride polymer sdmtionswmehcan be spun.
  • a liquid composition Iof matter which can be spun to form threads and the'like' and which can be cast to form n cfolnfprising'ia vinyl chloride polymer as solut in. a soliitio'n'in tetra hydrofura'ne' as solvent, said solvent having admixed therewith from about 10'.%'t0 about5.0% by weight of the mixture, of a butyrola'ctone'.
  • a liquid composition of matter which can be spun'to form threads and the like and which an be. ast it as, eo s n vinyl chloride polymer as solute in solution in tetrahydrofurane as solvent, said solvent having admixed therewith from about to about 50% by weight of the mixture, of butyrolactone.
  • 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 an additional solvent selected from the group consisting of lactones and lac tams, the proportion between additional solvent and tetrahydrofurane in the solvent mixture being about 1:3 by weight.
  • a liquid composition of matter which can be 6 valerolaotone and tetrahydrofurane in the solvent mixture being about 1:3 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 glycol carbonate, the proportion between glycol carbonate and tetrahydrofurane in the solvent mixture being about 1:3 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 e-caprolactam, the proportion between e-caprolactam and tetrahydrofurane in the solvent mixture being about 1:3 by weight.

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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)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Dispersion Chemistry (AREA)
  • Artificial Filaments (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US221713A 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 Expired - Lifetime US2616868A (en)

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DE287831X 1949-08-18

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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

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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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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 (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
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
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
WO1984002143A1 (en) * 1982-12-01 1984-06-07 Heimann F & Co As A glue solution
US4687798A (en) * 1986-01-27 1987-08-18 King Lloyd H Sr Solvent cement
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
FR2638167A1 (fr) * 1988-10-26 1990-04-27 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

Families Citing this family (8)

* 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
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
GB1035998A (en) * 1962-07-28 1966-07-13 Kurashiki Rayon Kk Method of manufacturing a spinning solution
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
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 (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
WO1984002143A1 (en) * 1982-12-01 1984-06-07 Heimann F & Co As A glue solution
US4675354A (en) * 1982-12-01 1987-06-23 A/S F. Heimann & Co. Glue solution
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
FR2638167A1 (fr) * 1988-10-26 1990-04-27 Eternit Financiere Colle pour matieres plastiques et procede de mise en oeuvre de cette colle
EP0370844A1 (fr) * 1988-10-26 1990-05-30 S.A. Financière Eternit Colle pour matieres plastiques et procédé 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
US5859103A (en) * 1996-07-19 1999-01-12 B. F. Goodrich Company Low volatile organic solvent based adhesive
US5962560A (en) * 1996-07-19 1999-10-05 The B.F. Goodrich Company Low volatile organic solvent based adhesive

Also Published As

Publication number Publication date
NL71803C (xx)
FR1023581A (fr) 1953-03-20
US2616869A (en) 1952-11-04
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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