US2617777A - 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 - Google Patents

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 Download PDF

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Publication number
US2617777A
US2617777A US221715A US22171551A US2617777A US 2617777 A US2617777 A US 2617777A US 221715 A US221715 A US 221715A US 22171551 A US22171551 A US 22171551A US 2617777 A US2617777 A US 2617777A
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US
United States
Prior art keywords
solvent
acid esters
tetrahydrofurane
mixture
vinyl chloride
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Expired - Lifetime
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US221715A
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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 andthe like andwhich 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 superior textile fibers.
  • admixture with tetrahydrofurane according to the invention produces a fundamental change not only in the solvent power of dimethylsulfoxide 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 sulfoxides and other chemical compounds of analogous structure, as for instance sulfones, sulfonic acid esters, sulfinic acid esters and the like, 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 difliculty at room temperature to form artificial threads, artificial bristles and the like, either by the wet spinning process or by the dry spinning process. In this way for example artificial threads are obtained with a strength of 2.5 to 3 grams/ denier and extensions of l5-25%.
  • the solutions are also very suitable for the production of films by casting.
  • the solutions preferably contain from about to about by weight of polymer.
  • Example 1 200 parts by Weight of polyvinyl chloride are introduced with stirring at 20 C. into a mixture of 150 parts by weight of dimethylsulfoxide and 600 parts by weight of tetrahydrofurane. The mixture is heated slowly to boilin while stirring and, when complete solution has been achieved, it is cooled again to about 20 C. The resultant solution can be spun, for example through multihole stainless steel jets, into water at 20 C.
  • Example 2 150 parts by weight of polyvinyl chloride are introduced with stirring at 20 C. into a mixture of 100 parts by weight of dimethylsulfone and 600 parts by weight of tetrahydrofurane.
  • Example 3 150 parts by weight of a copolymer from equimolecular amounts of acrylonitrile and vinyl chloride are introduced with stirring at 20 C. into a mixture of parts by weight of dimethy-lsulfone and 600 parts by weight of tetrahydrofu-rane. The mixture is heated until complete solution takes place, and is then cooled again to room temperature whereupon, after filtering if necessary, it may be spun into filament form, for example into water at 25 C.
  • Example 5 parts by weight of polyvinyl chloride are introduced with stirring at 20 C. into a mixture of 60 parts by weight of dimethylsulfone and 600 parts by weight of tetrahydrofurane. The mixture is heated and, when complete solution has been achieved, is cooled again to room temperature. The solution is then ready for use in the spinning of threads or in the casting of films.
  • Example 6 150 parts by weight of polyvinyl chloride are introduced with stirring at 20 C.- into a mixture of 250 parts by weight of dimethylsulfoxide and 509 parts by Weight of tetrahydrofurane, and the mixture heated. After complete solution has taken place, the solution is cooled to 20 C. and filtered, if necessary. It may then be converted into spun thread or cast film form.
  • Example 7 The procedure described in Example 5 is repeated, using parts by weight of the polyvinyl chloride, 300 parts by weight of the dimethylsulfone, and 300 parts by weight of the tetrahydrofurane.
  • the obtained solution may be spun into water at 25 C. or may be cast into film form.
  • dimethylsulfone of Examples 4, 5 and '7 and the dimethylsulfoxide of Example 6 may, with equivalent results, be replaced by an equivalent amount of tetramethylenesulfoxide, hexamethylenesulfoxide or methane sulfinic acid methyl ester, while otherwise proceeding as described in the respective example.
  • 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 an additional solvent selected from the group consisting of sulfone, sulfoxides, sulfonic acid esters and sulfinic acid esters which can di solve polyacrylonitrile completely but which do not by themselves 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 solute in a solution in tetrahydrofurane as solvent, said solvent having admixed therewith from about 10 to about 50% by weight of the mixture, of a sulfoxide.
  • 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 dimethylsulfoxide.
  • 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 sulfone, sulfoxides, sulfonic acid esters and sulfinic acid esters, the
  • 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 dimethylsulfoxide, the proportion between dimethylsulfoxide and tetrahydrofurane in the solvent mixture being about 1:2 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)
US221715A 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 Expired - Lifetime US2617777A (en)

Applications Claiming Priority (1)

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

Publications (1)

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US2617777A true US2617777A (en) 1952-11-11

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ID=6059385

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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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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

Country Status (6)

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

Cited By (7)

* 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
US3361697A (en) * 1965-03-24 1968-01-02 Du Pont Plasticized polylactams containing cyclic saturated sulfone
US4454091A (en) * 1980-06-10 1984-06-12 Rhone-Poulenc-Textile Solutions, which can be shaped, from mixtures of cellulose and polyvinyl chloride, and shaped articles resulting therefrom and the process for their manufacture
CN102414173A (zh) * 2009-05-04 2012-04-11 罗地亚经营管理公司 氟烷亚磺酸酯的制备方法
US20180016416A1 (en) * 2015-03-31 2018-01-18 Kaneka Corporation Thermoplastic modacrylic resin composition, method for manufacturing same, molded article of same, and acrylic fibers and method for manufacturing same

Families Citing this family (11)

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

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2545317A (en) * 1941-06-21 1951-03-13 Rhodiaceta Solution of a conjoint polymer of vinylidene chloride and ethyl acrylate

Family Cites Families (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

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2545317A (en) * 1941-06-21 1951-03-13 Rhodiaceta Solution of a conjoint polymer of vinylidene chloride and ethyl acrylate

Cited By (11)

* 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
US3361697A (en) * 1965-03-24 1968-01-02 Du Pont Plasticized polylactams containing cyclic saturated sulfone
US4454091A (en) * 1980-06-10 1984-06-12 Rhone-Poulenc-Textile Solutions, which can be shaped, from mixtures of cellulose and polyvinyl chloride, and shaped articles resulting therefrom and the process for their manufacture
CN102414173A (zh) * 2009-05-04 2012-04-11 罗地亚经营管理公司 氟烷亚磺酸酯的制备方法
CN102414173B (zh) * 2009-05-04 2014-01-01 罗地亚经营管理公司 氟烷亚磺酸酯的制备方法
US20180016416A1 (en) * 2015-03-31 2018-01-18 Kaneka Corporation Thermoplastic modacrylic resin composition, method for manufacturing same, molded article of same, and acrylic fibers and method for manufacturing same
US20190300675A1 (en) * 2015-03-31 2019-10-03 Kaneka Corporation Thermoplastic modacrylic resin composition, method for manufacturing same, molded article of same, and acrylic fibers and method for manufacturing same
US10752752B2 (en) * 2015-03-31 2020-08-25 Kaneka Corporation Thermoplastic modacrylic resin composition, method for manufacturing same, molded article of same, and acrylic fibers and method for manufacturing same
US10787558B2 (en) * 2015-03-31 2020-09-29 Kaneka Corporation Thermoplastic modacrylic resin composition, method for manufacturing same, molded article of same, and acrylic fibers and method for manufacturing same

Also Published As

Publication number Publication date
US2616868A (en) 1952-11-04
NL71803C (es)
FR1023581A (fr) 1953-03-20
US2616869A (en) 1952-11-04
GB674792A (en) 1952-07-02
NL72008C (es)
BE497653A (es)
NL70828C (es)
CH287831A (de) 1952-12-31

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