US2673163A - Process for working up cellulose derivatives - Google Patents
Process for working up cellulose derivatives Download PDFInfo
- Publication number
- US2673163A US2673163A US184333A US18433350A US2673163A US 2673163 A US2673163 A US 2673163A US 184333 A US184333 A US 184333A US 18433350 A US18433350 A US 18433350A US 2673163 A US2673163 A US 2673163A
- Authority
- US
- United States
- Prior art keywords
- cellulose
- cellulose derivatives
- melting
- content
- moisture
- 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
- 229920002678 cellulose Polymers 0.000 title claims description 34
- 239000001913 cellulose Substances 0.000 title claims description 31
- 238000000034 method Methods 0.000 title claims description 14
- 238000002844 melting Methods 0.000 claims description 17
- 230000008018 melting Effects 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000007493 shaping process Methods 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims 1
- 235000010980 cellulose Nutrition 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 229940081735 acetylcellulose Drugs 0.000 description 6
- 229920002301 cellulose acetate Polymers 0.000 description 6
- 239000002245 particle Substances 0.000 description 4
- 229920002284 Cellulose triacetate Polymers 0.000 description 3
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 3
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 3
- -1 fatty acid ester Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 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
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920006218 cellulose propionate Polymers 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- FJIKWRGCXUCUIG-UHFFFAOYSA-N lormetazepam Chemical compound N=1C(O)C(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1Cl FJIKWRGCXUCUIG-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003124 powdered cellulose Polymers 0.000 description 1
- 235000019814 powdered cellulose Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
- D01D1/00—Treatment of filament-forming or like material
- D01D1/04—Melting filament-forming substances
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B3/00—Preparation of cellulose esters of organic acids
- C08B3/22—Post-esterification treatments, including purification
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
- C08L1/08—Cellulose derivatives
- C08L1/10—Esters of organic acids, i.e. acylates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
- C08L1/08—Cellulose derivatives
- C08L1/10—Esters of organic acids, i.e. acylates
- C08L1/12—Cellulose acetate
-
- 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
- the present invention relates to improvements in the process for working up molten cellulose derivatives.
- cellulose derivative herein comprises all meltable derivatives of cellulose, primarily organic esters and ethers of cellulose.
- the invention relates to all kinds of processes in which the product passes through the molten state, for example, injection molding and spinning from the melt.
- cellulose derivatives display the disadvantage of insufiicient stability. This instability may cause undesirable discoloration; it may also impair the mechanical properties of the finished products.
- the melting point and thus the temperature at which the working up of the molten cellulose derivative may take place can be lowered considerably by imparting to the cellulose derivative a definite moisture content which is Within certain limits characteristic for each of the cellulose derivatives.
- the lower limit in the moisture content the open air.
- cellulose derivatives normally are produced in the anhydrous state and, when coming into contact with the atmosphere, they take up small amounts of moisture.
- the normally hydrolyzed cellulose acetate takes up about 1.5% of water, whereas the triacetate only takes up 0.1 to 0.3%.
- the moisture content required for the process of the present invention is definitely higher than that indicated above.
- the upper limit of the amount of water allowed is determined by the proportion of water that causes foaming of the molten cellulose derivative whose melting point is usually considerably above 100 C.
- the present invention is based on the discovery that cellulose derivatives can take no substantial proportions of water without losing them at temperatures above 100 C. and that the such proportions of water considerably lower themelting points of the cellulose derivatives and therewith the temperatures required for the Working 2 up process.
- the moisture content to be used generally lies between about 05-10%.
- the preferred moisture content is at 8-9% with a hydro lyzed cellulose acetate derivative, and at about 6% with cellulose triacetate.
- the content of water required in each case may be obtained in a simple manner by drying the cellulose derivative during its production only to the extent desired, or by spraying onto the derivative the amount of water still required above the content of moisture already present and then taking care that a uniform distribution occurs by mixing and storing in a sealed vessel. It is also possible to obtain the desired content of moisture by the action of steam on the cellulose derivative.
- cellulose derivatives Preferably highly stable cellulose derivatives should be used for such working, up processes, for instance, cellulose derivatives obtained by means of perchloric acid or zinc chloride catalysts. Further stabilization can be eiiected by first removing the atmospheric oxygen with evacuation, or by replacing it by inert gases.
- a further feature of the invention is that the cellulose derivatives are preferably in the finely divided state with a large surface, before being melted.
- Preferably loose or powdery precipitated cellulose derivatives are used.
- Their particle size should be such that they can be passed through a screen with a width of mesh of 1 mm.
- the particle size of the material to be worked up surprisingly influences the homogeneity of the finished product. This is true even when melting the cellulose derivatives in kneading machines, that is, to say under very high pressure.
- dyestuifs or pigments or other additive substances may be added to the cellulose derivatives during the preparatory stage of their production or in the melting vessel.
- a cellulose tripropionate, precipitated in the usual manner and having a moisture content of is pressed at about 150 C. by means of a worm press through an orifice of 0.2 mm. diameter, the resultant monofil shows variations in diameter, although the mass in the worm was well kneaded during melting. These changes in diameter are caused by the non-homogeneous melting of the cellulose tripropionate. If, however, the same cellulose triproprionate is converted to a loose, powdery form prior to melting, for example, by milling until the particles pass through a screen with a Width of mesh of at most 1 mm., a perfectly uniform monofil is thus obtained which displays improved properties.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Textile Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Biochemistry (AREA)
- Mechanical Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Artificial Filaments (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH688313X | 1949-09-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2673163A true US2673163A (en) | 1954-03-23 |
Family
ID=4529039
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US184333A Expired - Lifetime US2673163A (en) | 1949-09-14 | 1950-09-11 | Process for working up cellulose derivatives |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2673163A (enrdf_load_stackoverflow) |
| BE (1) | BE498083A (enrdf_load_stackoverflow) |
| CH (1) | CH277668A (enrdf_load_stackoverflow) |
| FR (1) | FR1042620A (enrdf_load_stackoverflow) |
| GB (1) | GB688313A (enrdf_load_stackoverflow) |
| NL (1) | NL156003B (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6224811B1 (en) | 1999-01-29 | 2001-05-01 | Celanese Acetate Llc | Thermal bonding of wet cellulose based fibers |
| US20070017395A1 (en) * | 2005-07-22 | 2007-01-25 | Neri Joel D | Method and apparatus for uniformly heating a substrate |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1516225A (en) * | 1923-11-15 | 1924-11-18 | Eastman Kodak Co | Process of manufacturing cellulose acetate |
| GB285829A (en) * | 1927-02-22 | 1928-12-06 | Ste Chim Usines Rhone | Process of manufacture of powdered plastic material |
| GB413262A (en) * | 1932-10-06 | 1934-07-12 | British Celanese | Treatment of cellulose derivatives |
| US1987610A (en) * | 1930-07-08 | 1935-01-15 | Celanese Corp | Organic ester of cellulose and method of treating the same |
| GB447187A (en) * | 1934-11-06 | 1936-05-06 | Arthur Eichengruen | Process for the production of moulding powders |
| US2180009A (en) * | 1938-06-16 | 1939-11-14 | Eastman Kodak Co | Precipitation of cellulose triacetate |
| US2303340A (en) * | 1939-05-16 | 1942-12-01 | Celanese Corp | Production of artificial materials |
| US2303339A (en) * | 1938-10-18 | 1942-12-01 | Celanese Corp | Manufacture of artificial materials |
| US2346210A (en) * | 1941-02-05 | 1944-04-11 | Du Pont | Method for improving organic derivatives of cellulose |
| US2356277A (en) * | 1940-10-25 | 1944-08-22 | Celanese Corp | Treatment of cellulose acetate |
| US2571975A (en) * | 1947-05-10 | 1951-10-16 | Du Pont | Melt spinning process |
-
0
- NL NL7312157.A patent/NL156003B/xx unknown
- BE BE498083D patent/BE498083A/xx unknown
-
1949
- 1949-09-14 CH CH277668D patent/CH277668A/de unknown
-
1950
- 1950-09-11 US US184333A patent/US2673163A/en not_active Expired - Lifetime
- 1950-09-13 FR FR1042620D patent/FR1042620A/fr not_active Expired
- 1950-09-14 GB GB22665/50A patent/GB688313A/en not_active Expired
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1516225A (en) * | 1923-11-15 | 1924-11-18 | Eastman Kodak Co | Process of manufacturing cellulose acetate |
| GB285829A (en) * | 1927-02-22 | 1928-12-06 | Ste Chim Usines Rhone | Process of manufacture of powdered plastic material |
| US1987610A (en) * | 1930-07-08 | 1935-01-15 | Celanese Corp | Organic ester of cellulose and method of treating the same |
| GB413262A (en) * | 1932-10-06 | 1934-07-12 | British Celanese | Treatment of cellulose derivatives |
| GB447187A (en) * | 1934-11-06 | 1936-05-06 | Arthur Eichengruen | Process for the production of moulding powders |
| US2180009A (en) * | 1938-06-16 | 1939-11-14 | Eastman Kodak Co | Precipitation of cellulose triacetate |
| US2303339A (en) * | 1938-10-18 | 1942-12-01 | Celanese Corp | Manufacture of artificial materials |
| US2303340A (en) * | 1939-05-16 | 1942-12-01 | Celanese Corp | Production of artificial materials |
| US2356277A (en) * | 1940-10-25 | 1944-08-22 | Celanese Corp | Treatment of cellulose acetate |
| US2346210A (en) * | 1941-02-05 | 1944-04-11 | Du Pont | Method for improving organic derivatives of cellulose |
| US2571975A (en) * | 1947-05-10 | 1951-10-16 | Du Pont | Melt spinning process |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6224811B1 (en) | 1999-01-29 | 2001-05-01 | Celanese Acetate Llc | Thermal bonding of wet cellulose based fibers |
| EP1024217A3 (en) * | 1999-01-29 | 2002-11-06 | Celanese Acetate, LLC. | Thermal bonding of wet cellulose based fibers |
| US20070017395A1 (en) * | 2005-07-22 | 2007-01-25 | Neri Joel D | Method and apparatus for uniformly heating a substrate |
Also Published As
| Publication number | Publication date |
|---|---|
| CH277668A (de) | 1951-09-15 |
| FR1042620A (fr) | 1953-11-03 |
| NL156003B (nl) | |
| BE498083A (enrdf_load_stackoverflow) | |
| GB688313A (en) | 1953-03-04 |
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