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 PDFInfo
- 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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- Prior art keywords
- tetrahydrofurane
- vinyl chloride
- solvent
- weight
- mixture
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Classifications
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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 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.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Dispersion Chemistry (AREA)
- Artificial Filaments (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
Patented Nov. 4, 1952 POLYMER IN A SOLVENT MIXTURE OF TETRAHYDROFURANE AND A NITRILE Erwin Heisenberg, Erlenbach-on-the-Main, and
Johannes Kleine, Munchen, Germany, assignors to Vereinigtc Glanzstofif-Fabriken A. G., Wuppcrtal-Elberfeld, Germany No Drawing. Application'April 18, 1951, Serial -No. 221,714. In Germany August '18, 1949 1 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
which canbe 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 fila ments 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 bespun.
Attempts have been made to overcome this disadvantage by subjecting the polyvinyl chloride to an additional chlorination before dissolv ing it. This does give an increased solubility, for example even in acetone, but such a procedure means that the process involves an additional step. i' Even when the spinning properties are improved byheating the solutions before spinning, for example to 50 C., 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 literature which are said to be suitable as solvents for high polymers and copolymers of vinyl compounds. Suchsolvents or mixtures thereof, however, do notgive solutions which can be used to spin threads of high quality. l
In order to increase the solubility of polylvinyl chloride, certain quantities of other vinyl compounds have been added during polymerization. It has injfact been possible to increase the solubility of polyvinyl chloride in this way, butaonly at the cost of imparting inferior textile properties to the spun threads obtained therefrom.
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." Theseobjectsarc 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. The .favorable influence of 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.
Moreover, admixture with" tetrahydrofurane according to the invention. produces a -fimd'a-=- mental change not only in the solvent power of adipic acid dinitrile but also in the solvent power of other solvents which have previously been proposed for polyacylonitrile 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 nitriles and other chemical compound-s of analogous structure, such for example as:
- 1,2,3-tricyano-propane;
1,1,2-tricyano-propane; 1,2-dicyano-cyclobutane; 1,3-dicyano-cyclobutane; 1,3,3,5-tetracyanopentane; 1,2,5-tric 'yano=1Fhydroxy pentane; 1,2,3}!-tetracyano-cyclobutane;
e 3 1,2-dicyano-3-methyl-cyclobutane; fl-hydroxyglutaric acid dinitrile; a-hydroxyglutaric acid dinitrile; Diglycolonitrile; Thiodiglycolenitrile; fi-methyl-malonitrile;
Bis- (5, 3-dicyano-isopropyl) -ether; Bis- (fi-cyanoethyl) -ether Bis-(B-cyanoethyl) -sulfide; etc.
Preferably the solvent mixture contains from 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 pro portions of their ingredients. i
When more than one of the said additional substances are admixed with tetrahydrofurane, which is possible according to the'present. inven. tion, preferably the proportions'of the ingredie ents are maintained within the above described limits,'the total quantity of the additional1 sub.- stances lying within these limits.
The favorable effects in improving the solubility with the solvent mixtures used according to the invention are obtained not only with polyvinyl chloride but also with copolymers of vinyl chloride, for example vinyl chloride-vinyl acetate copolymers, vinyl chloride-vinylidene chloride copolymers, vinyl chloride-styrene copolymers, vinyl chloride-vinyl acetate-vinylidene chloride copolymers, etc.
One of the most important advantages of solutions produced according to the invention is that the solutions 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.
in this way tor -example artificial threads are obtained with a strength of 2.5 to 3 grams/denier and tn i lls Q 5=25%. .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.
The following examples describe, solely by way of illustration, presently preferred embodiments of the process of the invention.
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
is thereupon cooled to room temperature (20 H After filtering, if necessary, the solution maybespun'into water at 25 C.
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.
In each of Examples 4, 5 and 6, the recited nitrile (succinonitrile, glutaric acid dinitrile, adiponitrile) may, with equivalent results, be replaced by an equivalent quantity of malonitrile, fumaric acid dinitrile, diglycolonitrile, or 1,2-dicyanoe-cyclobutane, while .otherwise proceeding as, described in ,the respective example.
Havingthus disclosed the invention, what is claimed is;
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 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.
2. 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.
3. 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.
4. A liquid composition of matter which can be s n' o torn; hr dsandthelike and whicncan 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, glutaric acid dinitrile, the proportion between additional solvent and tetrahydrofurane in the solvent mixture being about 1:4 by weight.
5. 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.
6. 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.
7. A liquid composition of matter which can be spun to form threads and the like and which REFERENCES CITED UNITED STATES PATENTS Name Date Ham Nov 7, 1950 Number
Claims (1)
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 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.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE287831X | 1949-08-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2616869A true US2616869A (en) | 1952-11-04 |
Family
ID=6059385
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
| 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 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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) | US2616869A (en) |
| BE (1) | BE497653A (en) |
| CH (1) | CH287831A (en) |
| FR (1) | FR1023581A (en) |
| GB (1) | GB674792A (en) |
| NL (3) | NL70828C (en) |
Cited By (1)
| 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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE965657C (en) * | 1953-08-28 | 1957-06-13 | Basf Ag | Solvent for acetylene |
| 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 (en) * | 1980-06-10 | 1981-12-11 | Rhone Poulenc Textile | SOLUTIONS CONFORMABLE FROM CELLULOSE MIXTURES AND VINYL POLYCHLORIDE AND FORM ARTICLES THEREOF |
| DK153684C (en) * | 1982-12-01 | 1990-02-26 | Heimann F & Co As | PROCEDURE FOR PREPARING A LIMITED JOINT BETWEEN SURFACES OF SUBSTANCES MADE BY WATER INSOLuble, SYNTHETIC ORGANIC POLYMERS |
| 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 (en) * | 1988-10-26 | 1994-07-29 | Eternit Financiere | ADHESIVE FOR PLASTIC MATERIALS AND METHOD OF IMPLEMENTING THE SAME |
| US5821289A (en) * | 1996-07-19 | 1998-10-13 | The B.F. Goodrich Company | Low volatile organic solvent based adhesive |
| US5817708A (en) * | 1996-07-19 | 1998-10-06 | The B. F. Goodrich Company | Low volatile organic solvent based adhesive |
| 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 |
Citations (1)
| 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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE443870A (en) * | 1941-06-21 |
-
0
- NL NL71803D patent/NL71803C/xx active
- NL NL72008D patent/NL72008C/xx active
- BE BE497653D patent/BE497653A/xx unknown
- NL NL70828D patent/NL70828C/xx active
-
1950
- 1950-08-12 CH CH287831D patent/CH287831A/en unknown
- 1950-08-15 GB GB20257/50A patent/GB674792A/en not_active Expired
- 1950-08-18 FR FR1023581D patent/FR1023581A/en not_active Expired
-
1951
- 1951-04-18 US US221714A patent/US2616869A/en not_active Expired - Lifetime
- 1951-04-18 US US221715A patent/US2617777A/en not_active Expired - Lifetime
- 1951-04-18 US US221713A patent/US2616868A/en not_active Expired - Lifetime
Patent Citations (1)
| 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)
| 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 |
|---|---|
| US2617777A (en) | 1952-11-11 |
| NL70828C (en) | |
| GB674792A (en) | 1952-07-02 |
| FR1023581A (en) | 1953-03-20 |
| CH287831A (en) | 1952-12-31 |
| US2616868A (en) | 1952-11-04 |
| BE497653A (en) | |
| NL72008C (en) | |
| NL71803C (en) |
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