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 PDFInfo
- 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
- Authority
- US
- United States
- Prior art keywords
- vinyl chloride
- tetrahydrofurane
- solvent
- weight
- chloride polymer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000002904 solvent Substances 0.000 title claims description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 title claims description 20
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 title claims description 18
- 229920000642 polymer Polymers 0.000 title claims description 17
- 150000002596 lactones Chemical class 0.000 title claims description 6
- 150000003951 lactams Chemical class 0.000 title claims description 5
- 238000009987 spinning Methods 0.000 title description 12
- 239000011877 solvent mixture Substances 0.000 title description 7
- 239000000203 mixture Substances 0.000 claims description 30
- 239000007788 liquid Substances 0.000 claims description 9
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 22
- 229930188620 butyrolactone Natural products 0.000 description 11
- 229920000915 polyvinyl chloride Polymers 0.000 description 9
- 239000004800 polyvinyl chloride Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 6
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 238000005266 casting Methods 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- GHELJWBGTIKZQW-UHFFFAOYSA-N 1-propan-2-ylpyrrolidin-2-one Chemical compound CC(C)N1CCCC1=O GHELJWBGTIKZQW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JMVIVASFFKKFQK-UHFFFAOYSA-N 1-phenylpyrrolidin-2-one Chemical compound O=C1CCCN1C1=CC=CC=C1 JMVIVASFFKKFQK-UHFFFAOYSA-N 0.000 description 1
- PTSGHGGLRADEFP-UHFFFAOYSA-N 4-methylpiperidin-2-one Chemical compound CC1CCNC(=O)C1 PTSGHGGLRADEFP-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- DZMJPYGBKWJZIR-UHFFFAOYSA-N chloroethene;styrene Chemical compound ClC=C.C=CC1=CC=CC=C1 DZMJPYGBKWJZIR-UHFFFAOYSA-N 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- JCMLRUNDSXARRW-UHFFFAOYSA-N trioxouranium Chemical compound O=[U](=O)=O JCMLRUNDSXARRW-UHFFFAOYSA-N 0.000 description 1
- 238000002166 wet spinning Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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.
Landscapes
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE287831X | 1949-08-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2616868A true US2616868A (en) | 1952-11-04 |
Family
ID=6059385
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
| 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 |
Family Applications After (2)
| 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 |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US2616868A (en(2012)) |
| BE (1) | BE497653A (en(2012)) |
| CH (1) | CH287831A (en(2012)) |
| FR (1) | FR1023581A (en(2012)) |
| GB (1) | GB674792A (en(2012)) |
| NL (3) | NL71803C (en(2012)) |
Cited By (10)
| 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)
| 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)
| 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 |
|---|---|---|---|---|
| NL66571C (en(2012)) * | 1941-06-21 |
-
0
- BE BE497653D patent/BE497653A/xx unknown
- NL NL72008D patent/NL72008C/xx active
- NL NL70828D patent/NL70828C/xx active
- NL NL71803D patent/NL71803C/xx active
-
1950
- 1950-08-12 CH CH287831D patent/CH287831A/de unknown
- 1950-08-15 GB GB20257/50A patent/GB674792A/en not_active Expired
- 1950-08-18 FR FR1023581D patent/FR1023581A/fr not_active Expired
-
1951
- 1951-04-18 US US221713A patent/US2616868A/en not_active Expired - Lifetime
- 1951-04-18 US US221714A patent/US2616869A/en not_active Expired - Lifetime
- 1951-04-18 US US221715A patent/US2617777A/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 (14)
| 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 |
|---|---|
| NL72008C (en(2012)) | |
| CH287831A (de) | 1952-12-31 |
| FR1023581A (fr) | 1953-03-20 |
| BE497653A (en(2012)) | |
| US2616869A (en) | 1952-11-04 |
| NL70828C (en(2012)) | |
| GB674792A (en) | 1952-07-02 |
| NL71803C (en(2012)) | |
| US2617777A (en) | 1952-11-11 |
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