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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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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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Prior art keywords
vinyl chloride
tetrahydrofurane
solvent
weight
chloride polymer
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US221713A
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Heisenberg Erwin
Kleine Johannes
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Glanzstoff AG
Vereinigte Glanzstoff Fabriken AG
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Glanzstoff AG
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    • 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
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
    • C08J3/091—Making 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L27/00—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 halogen; Compositions of derivatives of such polymers
    • C08L27/02—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 halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L27/04—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 halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
    • C08L27/06—Homopolymers or copolymers of vinyl chloride
    • 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
    • D01F6/02—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D01F6/08—Monocomponent 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
    • D01F6/10—Monocomponent 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
    • 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
    • C08J2327/00—Characterised 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
    • C08J2327/02—Characterised 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
    • C08J2327/04—Characterised 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
    • C08J2327/06—Homopolymers 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)

Description

Patented Nov. 4, 1952 SPINNING SOLUTIONS OF VINYL CHLORIDE POLYMER DISSOLVED IN A SOLVENT MIX- TURE CONTAINING TETRAHYDROFURAN E AND AN ADDITIONAL SOLVENT SELECTED FROM THE GROUP CONSISTING OF LAC-; TONES AND LACTAMS Erwin Heisenberg, Erlenbach-on-the-Main, and Johannes Kleinc, Munchen, Germany, assignors to Vereinigte Glanzstofi-Fabriken A. G., Wuppertal-Elberfeld, Germany, a German firm No Drawing.
Application April 18, 1951, Serial No. 221,713. In Germany August 18, 1949 8 Claims. (01. zoo-30.2
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.
It has been proposed in the literature to dissolve polyvinyl chloride in tetrahydrofurane and to work up these solutions into artificial threads. In this way, however, solutions are obtained of gluey'consistency which in practice cannot be spun.
Attempts have been made to overcome this disadvantage by subjecting the polyvinyl chloride to an additional chlorination before dissolving it. This does give an increased'solubility, for example even in acetone, but such a procedure means that the process involves an additional step. a
Even when the spinning properties are improved by heating the solutions before spinning, for example to 50 0., and even when spinning is carried out at this temperature, a satisfactory result is not obtained. Moreover, when working in the vicinity of the boiling point of the solvent, bubbles are readily formed in the thread which considerably reduces its quality. The thread is also embrittled by spinning at raised temperature so that optimum strength values are no longer obtained upon subsequent stretching.
A whole series of lactones and lactams have been proposed in the patent literaturewhich are said to be suitable as solvents for high polymers and copolymers of vinyl compounds. Such solvents or mixtures thereof, however, do not give solutions which can be used to spin threads of high quality.
In order to increase the solubility of polyvinyl chloride, certain quantities of other vinyl compounds have been added during polymerization. It has in fact been possible to increase the solubility of polyvinyl chloride in this way, but only at the cost of imparting inferior textile properties to the spun threads prepared therefrom.
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." These objects are 2 V achieved in a simple way according to the present invention, with production of good spinning solutions of vinyl chloride polymers and copolymers from which high quality threads can be spun, by incorporating into the tetr-ahydrofurane, which is used as solvent, certain quantities of butyrolactone. The results thus achieved are surprising because neither tetrahydrofurane nor butyrolactone by itself gives vinyl chloride polymer solutions which can be satisfactorily spun. The favorable influence of butyrolactone 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 butyrolactone 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 butyrolactone to three parts by weight of tetrahydrofurane.
Moreover, 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:
Glycol carbonate; 'y-Valerolactone; N-phenylpyrrolidone; N-methylpyrrolidone;
Diglycolide; a-Piperidone (a-valerolactam') a-Pyrrolidone -butyrolactam); 3-hydroxy-2-pyrrolidone; 4-hydroxy-2-pyrrolidone; N-fOllIlYL-l-DIDEIIdODG; e-Caprolactam;
sz-Heptolactam N-isopropyl-pyrrolidone; 'y-Caprolactoney a-Ethylbut'yrolactone; at,-Dimethyl-butyrolactone; -Isobutyl-butyrolactone; a-Ethy1-;8,y-dimethybbutyrolactone t'y-l3imethyl-butyrolactone;
we hy bi tyro ectqn a,a-Dimethyi a-yaleroiactone; 5,13-Dimethyl6-valerolactone; y-Diethyl-butyrolactone; o-Methylpyrrolidone ('y-valerolactam); p-Methyl-piperidone; etc.
Preferably the solvent mixture contains from 10 to 50% by weight of the additional solvent. In certain circumstances the upper limit can be exceeded since even then a certain improvement in solubility is obtained.
The examples given below describe in more detail individual mixtures which have particularly good properties due to the nature and pmportions of their ingredients.
When more than one of"the said "additional substances are admixed with tetrahydrofurane, which is possible according to this invention; preferably the proportions of the ingredients are maintainedjwithin the aboye described limits. the total quantity of the additionai vsubstances lying within these limits. I V
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. In this way for 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.
The following examples de'scr-ib'e, solely by way of illustration, presently "preferred embodiments of the process "of 'the'mvention:
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,
etc.
The 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.
Example '7 '0 P rt by we h 9 nellv i yl c ri a introduced with stirring at 25f? C. into a mixture of 250 parts by weight'oi glycol carbonate and 250 parts by weight of tetrahydroiurane, the mixture eate u ti mrl e's lu f n has taken a e.- and then cooled again to 210 The resultant solution is then ready for spinning or, casting.
Having thus disclosed the invention, what is claimed is: v f
1. "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.
2,. 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'.
' 3. 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.
4. 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.
5. A liquid composition of matter which can be 6 valerolaotone and tetrahydrofurane in the solvent mixture being about 1:3 by weight.
7. 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.
8. 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.
ERWIN HEISENBERG. JOHANNES KLEINE.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 2,529,449 Ham Nov. 7, 1950

Claims (1)

1. A LIQUID COMPOSITION OF MATTER WHICH CAN BE SPUN TO FORM THREADS AND THE LIKE AND WHICH CAN BE CASE 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 LACTONES AND LACTAMS WHICH CAN DISSOLVED POLYACRYLONITRILE COMPLETELY BUT WHICH DO NOT BY THEMSELVES GIVE VINYL CHLORIDE POLYMER SOLUTIONS WHICH CAN BE SPUN.
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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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
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

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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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Cited By (10)

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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 (en) * 1988-10-26 1990-04-27 Eternit Financiere GLUE FOR PLASTIC MATERIALS AND METHOD FOR IMPLEMENTING SAID GLUE
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 (en) * 1953-08-28 1957-06-13 Basf Ag Solvent for acetylene
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 (en) * 1980-06-10 1981-12-11 Rhone Poulenc Textile SOLUTIONS CONFORMABLE FROM CELLULOSE MIXTURES AND VINYL POLYCHLORIDE AND FORM ARTICLES THEREOF
FR2945040B1 (en) * 2009-05-04 2011-05-20 Rhodia Operations PROCESS FOR THE PREPARATION OF FLUOROALCANESULFINIC ACID ESTERS
WO2016158774A1 (en) * 2015-03-31 2016-10-06 株式会社カネカ Thermoplastic modacrylic resin composition, method for manufacturing same, molded article of same, and acrylic fibers and method for manufacturing same

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Cited By (14)

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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 (en) * 1988-10-26 1990-04-27 Eternit Financiere GLUE FOR PLASTIC MATERIALS AND METHOD FOR IMPLEMENTING SAID GLUE
EP0370844A1 (en) * 1988-10-26 1990-05-30 S.A. Financière Eternit Adhesive for plastics, and process for using this adhesive
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

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FR1023581A (en) 1953-03-20
US2617777A (en) 1952-11-11
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NL70828C (en)
US2616869A (en) 1952-11-04
NL72008C (en)
CH287831A (en) 1952-12-31

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