US3337670A - Process of recovering the constituents of a polyvinyl chloride coagulating bath - Google Patents
Process of recovering the constituents of a polyvinyl chloride coagulating bath Download PDFInfo
- Publication number
- US3337670A US3337670A US317113A US31711363A US3337670A US 3337670 A US3337670 A US 3337670A US 317113 A US317113 A US 317113A US 31711363 A US31711363 A US 31711363A US 3337670 A US3337670 A US 3337670A
- Authority
- US
- United States
- Prior art keywords
- solvent
- coagulating bath
- water
- bath
- azeotropic mixture
- 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
- 230000001112 coagulating effect Effects 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 10
- 229920000915 polyvinyl chloride Polymers 0.000 title description 10
- 239000004800 polyvinyl chloride Substances 0.000 title description 10
- 239000000470 constituent Substances 0.000 title description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 229920000642 polymer Polymers 0.000 claims description 14
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 12
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 9
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 8
- 238000009987 spinning Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 238000005345 coagulation Methods 0.000 description 8
- 230000015271 coagulation Effects 0.000 description 8
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- UDHXJZHVNHGCEC-UHFFFAOYSA-N Chlorophacinone Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)C(=O)C1C(=O)C2=CC=CC=C2C1=O UDHXJZHVNHGCEC-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 240000005020 Acaciella glauca Species 0.000 description 1
- 101100165177 Caenorhabditis elegans bath-15 gene Proteins 0.000 description 1
- 125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- -1 sec-butyl alcohols Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- 238000002166 wet spinning Methods 0.000 description 1
Images
Classifications
-
- 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
- D01F13/00—Recovery of starting material, waste material or solvents during the manufacture of artificial filaments or the like
- D01F13/04—Recovery of starting material, waste material or solvents during the manufacture of artificial filaments or the like of synthetic polymers
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
- Y02P70/62—Manufacturing or production processes characterised by the final manufactured product related technologies for production or treatment of textile or flexible materials or products thereof, including footwear
Definitions
- the process of the present invention makes it possible to recover in a very simple manner the constituents of the coagulation baths.
- the new process comprises extruding a solution of a vinyl chloride polymer in cyclopentanone or cyclohexanone into an azeotropic mixture of water and a monohydric aliphatic alcohol containing three or four carbon atoms, preferably isopropyl alcohol, n-propyl alcohol or sec-butyl alcohol.
- the aliphatic alcohol distils first as an azeotrope with water, and may be immediately returned as such into the spinning bath, since it has the appropriate composition.
- the solvent for the vinyl chloride polymer e.g. cyclopentanone or cyclohexanone
- the solvent for the vinyl chloride polymer is recovered in the anhydrous state from the bottom of the distillation column and can be reused immediately for dissolving more polyvinyl chloride.
- This ready separation of the constituents of the spinning bath and the possibility of immediately reusing them make it possible to use only small quantities of solvent and aliphatic alcohol.
- vinyl chloride polymer is used herein to denote, besides polyvinyl chloride itself, polyvinyl chloride copolymers containing a major proportion of polyvinyl chloride, and derivatives of polyvinyl chloride obtained by superchlorination.
- the spinning solutions may optionally contain substances intended to modify certain of the mechanical, physical, and chemical or dyeing properties of the filaments produced.
- the yarns and fibres obtained by the process of the invention may be finished in any appropriate operation and may be used alone, or blended with other natural or artificial (including wholly synthetic) fibres, in weaving or knitting or for the production of unwoven articles.
- EXAMPLE 1 A crystalline polyvinyl chloride polymer, obtained by polymerization at 15 C. and having an Afnor index of 3,337,670 Patented Aug. 22, 1967 130 (index determined at 25 C. in cy-clohexanone in accordance with the French standard NF T 51013), is dissolved in cyclohexanone to form a 25% solution. This solution is then heated to 140 C. and extruded through a spinneret having 260 holes each of a diameter of 0.06 mm. into a first bath having the composition of an isopropyl alcohol/water azeotrope (12.7% of water).
- the length of the bath is cm., the temperature 50 C., and the speed of the filaments leaving the bath is 13 m./ minute.
- the filaments then enter a second bath 15 cm. long of the same composition and temperature as the first. They leave this bath also at 13 m./ minute.
- the filaments next enter a third bath identical to the second one, and a fourth bath, which is also the same except that its length is 20 cm.
- the filaments enter a fifth bath 20 cm. long consisting of water at C.
- the filaments are wound up at 30 m./min. and then stretched three times their length in hot air at C.
- the filaments finally obtained have a breaking strength of 2.8 g./ den. and an elongation at break of 17%.
- the various components of the coagulation baths are recovered by fractional distillation.
- the isopropyl alcohol is recovered as its azeotrope with Water and the substantially anhydrous cyclohexanone is recovered in directly reusable form.
- EXAMPLE 2 A 25% polyvinyl chloride solution in cyclopentanone is wet-spun into a coagulation bath having the composition of the n-propyl alcohol/water azeotrope (27% of water). The components of the coagulation baths are thereafter recovered as in Example 1, by fractional distillation. The azeotrope of the n-propyl alcohol, which boils at 87 C., separates immediately from the cyclopentanone, which boils at C.
- EXAMPLE 3 A 12% solution in cyclohexanone of a vinyl chloride polymer having an Afnor index of 500 is wet-spun, using as coagulation bath the azeotrope of sec-butyl alcohol (30% of water). The various components of the coagulation baths are thereafter recovered, as in the preceding examples, by fractional distillation. The azeotrope of the sec-butyl alcohol, which boils at 88.5 C., separates immediately from the cyclohexanone which boils at 156 C.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Artificial Filaments (AREA)
- Shaping By String And By Release Of Stress In Plastics And The Like (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR913141A FR1345068A (fr) | 1962-10-23 | 1962-10-23 | Procédé de filage humide de solutions de polymères à base de chlorure de vinyle |
Publications (1)
Publication Number | Publication Date |
---|---|
US3337670A true US3337670A (en) | 1967-08-22 |
Family
ID=8789296
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US317113A Expired - Lifetime US3337670A (en) | 1962-10-23 | 1963-10-18 | Process of recovering the constituents of a polyvinyl chloride coagulating bath |
Country Status (7)
Country | Link |
---|---|
US (1) | US3337670A (enrdf_load_html_response) |
BE (1) | BE638968A (enrdf_load_html_response) |
DE (1) | DE1251904B (enrdf_load_html_response) |
ES (1) | ES291566A1 (enrdf_load_html_response) |
FR (2) | FR1345068A (enrdf_load_html_response) |
GB (1) | GB985729A (enrdf_load_html_response) |
NL (2) | NL299515A (enrdf_load_html_response) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3440148A (en) * | 1965-01-27 | 1969-04-22 | Acsa Applic Chimiche Spa | Method for recovering the components of a coagulation bath used in the spinning of polyvinyl chloride |
US3457343A (en) * | 1965-08-28 | 1969-07-22 | Algemeine Kunstzijde Unie Nv | Wet spinning process |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5248471A (en) * | 1987-07-06 | 1993-09-28 | Alliedsignal Inc. | Process for forming fibers |
WO2010106143A1 (en) | 2009-03-20 | 2010-09-23 | Dsm Ip Assets B.V. | Net for aquaculture |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2327872A (en) * | 1940-07-01 | 1943-08-24 | Pro Phylae Tic Brush Company | Method of making synthetic materials such as fibers |
US2953818A (en) * | 1958-02-14 | 1960-09-27 | Du Pont | Process for producing polyvinyl fluoride film from mixture of polyvinyl fluoride particles and latent solvent therefor |
US3078242A (en) * | 1957-09-30 | 1963-02-19 | Du Pont | Composition comprising a solution of an organic compound containing two reactive groups and a polymer in the form of particles below about 15 microns |
-
0
- BE BE638968D patent/BE638968A/xx unknown
- NL NL133195D patent/NL133195C/xx active
- DE DENDAT1251904D patent/DE1251904B/de active Pending
- NL NL299515D patent/NL299515A/xx unknown
-
1962
- 1962-10-23 FR FR913141A patent/FR1345068A/fr not_active Expired
-
1963
- 1963-09-11 ES ES0291566A patent/ES291566A1/es not_active Expired
- 1963-10-18 GB GB41310/63A patent/GB985729A/en not_active Expired
- 1963-10-18 US US317113A patent/US3337670A/en not_active Expired - Lifetime
-
1965
- 1965-02-11 FR FR5193A patent/FR87296E/fr not_active Expired
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2327872A (en) * | 1940-07-01 | 1943-08-24 | Pro Phylae Tic Brush Company | Method of making synthetic materials such as fibers |
US3078242A (en) * | 1957-09-30 | 1963-02-19 | Du Pont | Composition comprising a solution of an organic compound containing two reactive groups and a polymer in the form of particles below about 15 microns |
US2953818A (en) * | 1958-02-14 | 1960-09-27 | Du Pont | Process for producing polyvinyl fluoride film from mixture of polyvinyl fluoride particles and latent solvent therefor |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3440148A (en) * | 1965-01-27 | 1969-04-22 | Acsa Applic Chimiche Spa | Method for recovering the components of a coagulation bath used in the spinning of polyvinyl chloride |
US3457343A (en) * | 1965-08-28 | 1969-07-22 | Algemeine Kunstzijde Unie Nv | Wet spinning process |
Also Published As
Publication number | Publication date |
---|---|
BE638968A (enrdf_load_html_response) | 1900-01-01 |
ES291566A1 (es) | 1964-01-16 |
NL133195C (enrdf_load_html_response) | 1900-01-01 |
GB985729A (en) | 1965-03-10 |
FR1345068A (fr) | 1963-12-06 |
NL299515A (enrdf_load_html_response) | 1900-01-01 |
DE1251904B (de) | 1967-10-12 |
FR87296E (fr) | 1966-07-08 |
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