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 PDFInfo
- 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
- Authority
- US
- United States
- Prior art keywords
- solvent
- acid esters
- tetrahydrofurane
- mixture
- vinyl chloride
- 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
- 239000000203 mixture Substances 0.000 title claims description 28
- 239000002904 solvent Substances 0.000 title claims description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 title claims description 23
- 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 16
- 150000003462 sulfoxides Chemical class 0.000 title claims description 7
- 150000003457 sulfones Chemical class 0.000 title claims description 6
- 150000003453 sulfinic acid esters Chemical class 0.000 title claims description 5
- 150000003459 sulfonic acid esters Chemical class 0.000 title claims description 5
- 239000007788 liquid Substances 0.000 claims description 7
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 12
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 12
- 229920000915 polyvinyl chloride Polymers 0.000 description 10
- 239000004800 polyvinyl chloride Substances 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 8
- 238000009987 spinning Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 239000011877 solvent mixture Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- -1 Tetramethylenesulfoxide Pentamethylenesulfoxide Hexamethylenesulfoxide Chemical compound 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- PLUBXMRUUVWRLT-UHFFFAOYSA-N Ethyl methanesulfonate Chemical compound CCOS(C)(=O)=O PLUBXMRUUVWRLT-UHFFFAOYSA-N 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- IEJNAGSUKYCWCR-UHFFFAOYSA-N chloroethene;1,1-dichloroethene;ethenyl acetate Chemical compound ClC=C.ClC(Cl)=C.CC(=O)OC=C IEJNAGSUKYCWCR-UHFFFAOYSA-N 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- XCEDLSQLKUOFPM-UHFFFAOYSA-N diethyl ethane-1,2-disulfonate Chemical compound CCOS(=O)(=O)CCS(=O)(=O)OCC XCEDLSQLKUOFPM-UHFFFAOYSA-N 0.000 description 1
- KVUVCQAPHDGTOD-UHFFFAOYSA-N dimethyl chloromethanedisulfonate Chemical compound COS(=O)(=O)C(S(=O)(=O)OC)Cl KVUVCQAPHDGTOD-UHFFFAOYSA-N 0.000 description 1
- OAKHVBAFWUJTIW-UHFFFAOYSA-N dimethyl propane-1,3-disulfonate Chemical compound COS(=O)(=O)CCCS(=O)(=O)OC OAKHVBAFWUJTIW-UHFFFAOYSA-N 0.000 description 1
- 238000000578 dry spinning Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- HCVLXRGYPQDGMC-UHFFFAOYSA-N ethyl methanesulfinate Chemical compound CCOS(C)=O HCVLXRGYPQDGMC-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- OPUAWDUYWRUIIL-UHFFFAOYSA-N methanedisulfonic acid Chemical compound OS(=O)(=O)CS(O)(=O)=O OPUAWDUYWRUIIL-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- UTOWKUXZEJXEMP-UHFFFAOYSA-N methyl ethanesulfinate Chemical compound CCS(=O)OC UTOWKUXZEJXEMP-UHFFFAOYSA-N 0.000 description 1
- UJXJECMZMLSTEB-UHFFFAOYSA-N methyl methanesulfinate Chemical compound COS(C)=O UJXJECMZMLSTEB-UHFFFAOYSA-N 0.000 description 1
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 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
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
- LBMZLLXZMSMJPJ-UHFFFAOYSA-N thiepane 1-oxide Chemical compound O=S1CCCCCC1 LBMZLLXZMSMJPJ-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 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 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.
Landscapes
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE287831X | 1949-08-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2617777A true US2617777A (en) | 1952-11-11 |
Family
ID=6059385
Family Applications (3)
| 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 |
| 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 |
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 |
| 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) | US2617777A (enrdf_load_html_response) |
| BE (1) | BE497653A (enrdf_load_html_response) |
| CH (1) | CH287831A (enrdf_load_html_response) |
| FR (1) | FR1023581A (enrdf_load_html_response) |
| GB (1) | GB674792A (enrdf_load_html_response) |
| NL (3) | NL70828C (enrdf_load_html_response) |
Cited By (7)
| 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)
| 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 |
| 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 |
Citations (1)
| 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)
| 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 |
-
0
- NL NL72008D patent/NL72008C/xx active
- NL NL71803D patent/NL71803C/xx active
- NL NL70828D patent/NL70828C/xx active
- BE BE497653D patent/BE497653A/xx unknown
-
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 US221715A patent/US2617777A/en not_active Expired - Lifetime
- 1951-04-18 US US221714A patent/US2616869A/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 |
|---|---|---|---|---|
| US2545317A (en) * | 1941-06-21 | 1951-03-13 | Rhodiaceta | Solution of a conjoint polymer of vinylidene chloride and ethyl acrylate |
Cited By (11)
| 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 |
|---|---|
| FR1023581A (fr) | 1953-03-20 |
| NL71803C (enrdf_load_html_response) | |
| CH287831A (de) | 1952-12-31 |
| NL72008C (enrdf_load_html_response) | |
| NL70828C (enrdf_load_html_response) | |
| GB674792A (en) | 1952-07-02 |
| US2616869A (en) | 1952-11-04 |
| BE497653A (enrdf_load_html_response) | |
| US2616868A (en) | 1952-11-04 |
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