US2036860A - Process of producing artificial filaments - Google Patents
Process of producing artificial filaments Download PDFInfo
- Publication number
- US2036860A US2036860A US373685A US37368529A US2036860A US 2036860 A US2036860 A US 2036860A US 373685 A US373685 A US 373685A US 37368529 A US37368529 A US 37368529A US 2036860 A US2036860 A US 2036860A
- Authority
- US
- United States
- Prior art keywords
- filaments
- cellulose
- solvent
- derivative
- yarns
- 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
- 238000000034 method Methods 0.000 title description 10
- 229920002678 cellulose Polymers 0.000 description 26
- 239000001913 cellulose Substances 0.000 description 26
- 239000002904 solvent Substances 0.000 description 23
- 230000001376 precipitating effect Effects 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
- 229920002301 cellulose acetate Polymers 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000009987 spinning Methods 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 8
- 239000010902 straw Substances 0.000 description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 235000013773 glyceryl triacetate Nutrition 0.000 description 4
- 239000001087 glyceryl triacetate Substances 0.000 description 4
- 239000003350 kerosene Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 239000013557 residual solvent Substances 0.000 description 4
- 229960002622 triacetin Drugs 0.000 description 4
- 238000002166 wet spinning Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- VQLYBLABXAHUDN-UHFFFAOYSA-N bis(4-fluorophenyl)-methyl-(1,2,4-triazol-1-ylmethyl)silane;methyl n-(1h-benzimidazol-2-yl)carbamate Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1.C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 VQLYBLABXAHUDN-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 1
- KFUSEUYYWQURPO-UHFFFAOYSA-N 1,2-dichloroethene Chemical group ClC=CCl KFUSEUYYWQURPO-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229920001727 cellulose butyrate Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 229920006218 cellulose propionate Polymers 0.000 description 1
- -1 choloroform Substances 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- PCYQQSKDZQTOQG-NXEZZACHSA-N dibutyl (2r,3r)-2,3-dihydroxybutanedioate Chemical compound CCCCOC(=O)[C@H](O)[C@@H](O)C(=O)OCCCC PCYQQSKDZQTOQG-NXEZZACHSA-N 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 239000001761 ethyl methyl cellulose Substances 0.000 description 1
- 235000010944 ethyl methyl cellulose Nutrition 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
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
- D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
- D01F2/24—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from cellulose derivatives
- D01F2/28—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from cellulose derivatives from organic cellulose esters or ethers, e.g. cellulose acetate
Definitions
- This invention relates to the preparation of artificial filaments containing derivatives of cellulose and relates more particularly to the making of artificial filaments, yarns, bristles, straw or the like by a wet spinning process.
- An object of our invention is to prepare lustrous artificial filaments, yarns, bristles, straw and the like by a wet spinning process. Other objects of our invention will appear from the following detailed description.
- the material to be formed by our process may be in the nature of fine filaments which are extruded through fine orifices, and these filaments may be associated together to form yarns. If artificial bristles are to be made, orifices of larger size are employed in the spinning, while fine slits in metal caps, glass tubes or the like may be employed for spinning artificial straw.
- organic derivatives of cellulose While we prefer to employ organic derivatives of cellulose in making the filaments and the like, other derivatives of cellulose such as cellulose nitrate may be employed.
- organic derivatives of cellulose are organic esters of cellulose such *as cellulose acetate, cellulose formate, cellulose propionate and cellulose butyrate and cellulose ethers such as ethyl cellulose, methyl cellulose and benzyl cellulose.
- a substance which is a solvent for the derivative of cellulose at elevated temperatures which substance is not readily removable from the filaments or yarns by the precipitating bath, either because it is relatively insoluble therein or for other reasons.
- Such substance may or may not be a solvent for the derivative of cellulose at ordinary temperatures.
- examples of such substances when water is used as a precipitating bath are ethylene dichloride, methylene chloride, methyl phenyl ketone (acetophenone), tetrachlorethane, triacetin or dibutyl tartrate.
- This substance may be added to solutions of the derivative of cellulose wherein the derivative of cellulose is dissolved in liquids which are of themselves solvents for the derivative of cellulose, or they may be employed to form a solvent in admixture with the other liquids employed.
- cellulose acetate may be dissolved in a solvent mixture comprising ethyl or methyl alcohol and ethylene dichloride or methylene chloride neither of which is alone a solvent for the cellulose acetate, and upon extrusion of the solution into water, the alcohol is dissolved away, thus precipitating the filaments containing the derivative of cellulose and some methylene chloride or ethylene dichloride.
- any suitable solvent may be employed for preparing the spinning solution for the derivative of cellulose, examples of which are acetone, choloroform, mixtures of methylene chloride and ethyl or methyl alcohol, or mixtures of dichlorethylene and methyl or ethyl alcohol, depending upon the solubility characteristics of the specific derivative of cellulose employed.
- any suitable liquid that is a nonsolvent for the derivative of cellulose, but which dissolves or is miscible with at least part of the solvent may be employed. Examples of these are water or hydrocarbon such as benzene, toluene and their homologues or other coal tar hydrocarbons, and gasoline, kerosene or other petroleum hydrocarbons.
- the yarns, filaments, straw and the like as they leave the precipitating bath are opaque and lustrousless.
- they are subjected to elevated temperatures whereupon the precipitating liquid adhering to or absorbed in the same is driven off and the solvent or latent solvent because of its increased solvent power at elevated temperatures, causes the filaments, yarns, straw, bristles and the like to assume lustre and transparency.
- the heating of the filaments and the like may be done in any suitable manner, such as by causing the same to contact along a suitable length with feed rolls, pipes, rods, plates, etc., which may be heated electrically, by steam or in any other suitable manner.
- feed rolls pipes, rods, plates, etc.
- steam or in any other suitable manner.
- This heating of the filaments and the like may be performed upon the same immediately after they leave the precipitating bath, or the filaments may be first wound or wound and twisted prior to their being subjected to the heating treatment.
- a stretch may be imparted to the same so that finer filaments and the like may be produced through relatively large jet orifices.
- Example I A spinning solution is prepared as follows:
- the threads or filaments Prior to contacting with the rolls, the threads or filaments are dull and lustreless, but after contact with the heated rolls they are clear and lustrous. This is due to the fact that the ethylene dichloride and triacetin are hardly removed by the precipitating bath and remain in the yarn and are absorbed strongly by the yarns at the elevated temperatures as the water of the precipitating. bath is driven off. The products thus formed are materially stronger, tougher and more pliable than products not receiving this heat treatment.
- Example II A spinning solution is prepared by dissolving 1 part of an acetone soluble cellulose acetate, containing 54% by weight of combined acetic acid in 3 parts of a solvent mixture consisting of Parts by Weight Acetone 95 Methyl phenyl ketone 5 This solution is spun exactly as in Example I.
- the methyl phenyl ketone which is not soluble in or appreciably removed by the precipitating bath, causes the yarn to become lustrous and optically continuous when it is subjected to the elevated temperatures.
- Example III A spinning solution is formed by dissolving 1 part by weight of an acetone soluble cellulose acetate in 3 parts by weight of a solvent mixture consisting of:
- Method of forming filaments and the like which comprises extruding a solution of an organic substitution derivative of cellulose, containing a substance having .a solvent power for said cellulose derivative at elevated temperatures only, through orifices into a precipitating bath which incompletely extracts said substance, and bringing the filaments formed thereby into contact with a heated surface.
- Method of forming filaments and the like which comprises extruding a solution of cellulose acetate, containing a substance having a solvent power for cellulose acetate at elevated temperatures only, through orifices into a precipitating bath which incompletely extracts said substance, and bringing the filaments formed thereby into contact with a heated surface.
- Method of forming filaments and the like which comprises extruding a solution of an organic substitution derivative of cellulose, containing a substance substantially insoluble in water and having a. solvent power for said cellulose derivative at elevated temperatures only, through orifices into a precipitating bath containing water, and bringing the filaments formed thereby into contact with a heated surface.
- Method of forming filaments and the like which comprises extruding a solution of cellulose acetate, containing a substance substantially insoluble in water and having a solvent power for cellulose acetate at elevated temperatures only,
- Method of forming filaments and the like which comprises extruding a solution of cellulose acetate, comprising diethylene glycol, through orifices into a precipitating bath containing kerosene, and bringing the filaments formed. thereby 10 into contact with a heated surface.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Artificial Filaments (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE371394D BE371394A (en, 2012) | 1929-06-25 | ||
| US373685A US2036860A (en) | 1929-06-25 | 1929-06-25 | Process of producing artificial filaments |
| GB18923/30A GB356343A (en, 2012) | 1929-06-25 | 1930-06-20 | |
| FR697814D FR697814A (fr) | 1929-06-25 | 1930-06-23 | Perfectionnements à la fabrication des filaments et autres matières artificielles à l'aide de dérivés cellulosiques |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US373685A US2036860A (en) | 1929-06-25 | 1929-06-25 | Process of producing artificial filaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2036860A true US2036860A (en) | 1936-04-07 |
Family
ID=23473433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US373685A Expired - Lifetime US2036860A (en) | 1929-06-25 | 1929-06-25 | Process of producing artificial filaments |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2036860A (en, 2012) |
| BE (1) | BE371394A (en, 2012) |
| FR (1) | FR697814A (en, 2012) |
| GB (1) | GB356343A (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3023075A (en) * | 1954-10-26 | 1962-02-27 | British Celanese | Fibrous material |
| US3084414A (en) * | 1959-06-17 | 1963-04-09 | Celanese Corp | Aqueous spin bath |
-
0
- BE BE371394D patent/BE371394A/xx unknown
-
1929
- 1929-06-25 US US373685A patent/US2036860A/en not_active Expired - Lifetime
-
1930
- 1930-06-20 GB GB18923/30A patent/GB356343A/en not_active Expired
- 1930-06-23 FR FR697814D patent/FR697814A/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3023075A (en) * | 1954-10-26 | 1962-02-27 | British Celanese | Fibrous material |
| US3084414A (en) * | 1959-06-17 | 1963-04-09 | Celanese Corp | Aqueous spin bath |
Also Published As
| Publication number | Publication date |
|---|---|
| FR697814A (fr) | 1931-01-22 |
| BE371394A (en, 2012) | |
| GB356343A (en, 2012) | 1931-09-10 |
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