US2814603A - Dimethylformamide-aliphatic diester spinning solutions of polyacrylonitriles - Google Patents
Dimethylformamide-aliphatic diester spinning solutions of polyacrylonitriles Download PDFInfo
- Publication number
- US2814603A US2814603A US392045A US39204553A US2814603A US 2814603 A US2814603 A US 2814603A US 392045 A US392045 A US 392045A US 39204553 A US39204553 A US 39204553A US 2814603 A US2814603 A US 2814603A
- Authority
- US
- United States
- Prior art keywords
- dimethylformamide
- percent
- solvent
- spinning solutions
- polyacrylonitriles
- 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
- 238000009987 spinning Methods 0.000 title claims description 13
- 229920002239 polyacrylonitrile Polymers 0.000 title claims description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 44
- 239000002904 solvent Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000011877 solvent mixture Substances 0.000 description 5
- 238000002845 discoloration Methods 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- BPGDAMSIGCZZLK-UHFFFAOYSA-N acetyloxymethyl acetate Chemical group CC(=O)OCOC(C)=O BPGDAMSIGCZZLK-UHFFFAOYSA-N 0.000 description 3
- -1 aliphatic diester Chemical class 0.000 description 3
- 235000015110 jellies Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- MLMGJTAJUDSUKA-UHFFFAOYSA-N 2-ethenyl-1h-imidazole Chemical compound C=CC1=NC=CN1 MLMGJTAJUDSUKA-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- FERWQICGOAENLD-UHFFFAOYSA-N butanoyloxymethyl butanoate Chemical compound CCCC(=O)OCOC(=O)CCC FERWQICGOAENLD-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- RYFCKWOMDKDLEZ-UHFFFAOYSA-N propanoyloxymethyl propanoate Chemical compound CCC(=O)OCOC(=O)CC RYFCKWOMDKDLEZ-UHFFFAOYSA-N 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
-
- 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
- D01F6/18—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 unsaturated nitriles, e.g. polyacrylonitrile, polyvinylidene cyanide
-
- 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
- D01F6/28—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D01F6/38—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds comprising unsaturated nitriles as the major constituent
-
- 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
- C08J2333/00—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 only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2333/18—Homopolymers or copolymers of nitriles
- C08J2333/20—Homopolymers or copolymers of acrylonitrile
Definitions
- This invention relates to the production of filaments from polyacrylonitrile or from mixed polymerisates containing polyacrylonitrile, dissolved in a solvent consisting of, or containing, dimethylformamide.
- the number of solvents suitable for practical use in the preparation of spinning solutions from polyacrylonitrile or mixed polymerisates containing this compound is particularly limited. It is equally known that dimethylformamide is on the Whole a satisfactory solvent, but requires being improved in several directions. Thus, for instance, the dispersion which is first formed when trying to dissolve the polyacrylonitrile in dimethylformamide, causes a tendency of the nitrile to form a jelly and renders the spinning solution inhomogenous to the extent that the spinning process is disturbed and the filament breaks.
- the compound to be added to the dimethylformamide is methyleneglycol-diacetate, methyleneglycoldipropionate or methyleneglycol-dibutyrate.
- I may, for instance, proceed as follows:
- Example 1 22 parts by weight of polyacrylonitrile, having a K-value of 87, were added to 78 parts of a solvent mixture consisting of 85 percent by weight dimethylformamide and 15 percent methyleneglycol-diacetate.
- the polymerisate was stirred according to well-known methods to form a dispersion which then dissolved in the solvent mixture under heating.
- the solution thus obtained yielded an unobjectionable liquid of high filament-forming capacity.
- the filaments spun from it had a particularly high stretching capacity and stretching velocities of 300-350 meters per minute could be employed.
- the filaments possessed particularly favorable mechanical properties and showed a resistance to breaking of 42 kilometers.
- Example 2 19 parts by weight of a co-polymer formed of 95 percent acrylonitrile and 5 percent vinylimidazol, having a K-value of about 92, was stirred to form a dispersion in percent of a solvent mixture consisting of percent by weight dimethylformarnide and 20 percent ethylideneglycol-diacetate. After heating to fusion temperature a light-colored solution was obtained, which could be spun without any disturbances. The filaments from the solution could be stretched at a velocity of 250-300 meters per minute. The resistance to breaking extended to 40 kilometers.
- Example 3 21 parts by weight of a co-polymer formed from percent by weight acrylonitrile and 10 percent acrylic acid amide (K-value near 87) were dispersed in 79 parts of a solvent mixture formed of 82 percent dimethylformamide and 18 percent methyleneglycol-dipropionate.
- Example 2 In following the methods reported with reference to Example 1 a solution of high filament-forming capacity was obtained. The resistance of the filaments extended to about 42 kilometers.
- the process of preparing spinning solutions which comprises dissolving a member selected from the group consisting of polyacrylonitrile and a copolymer of acrylo nitrile with another polymerizable unsaturated compound in minor proportion in a solvent comprising dimethylformamide in admixture with from 5 to 20 percent by weight of an aliphatic diester of the formula and n has the value zero to two inclusive.
- the process of preparing spinning solutions which 4 comprises dissolving a member selected from the group consisting of polyacrylonitn'le and a copolymer of acrylonitrile with another polymerizable unsaturated compound in minor proportion in a solvent comprising dimethylformarnide in admixture with from 7 to 10 percent by weight of an aliphatic diester of the formula CI'h-(CH2)11,.C0.0.R.O.CO. (CH2)nCH3 wherein R is a member of the group consisting of -OH;- and --0H- and n has the value zero to two inclusive.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Dispersion Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Artificial Filaments (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEV5267A DE926567C (de) | 1952-12-18 | 1952-12-18 | Verfahren zur Herstellung von Spinnloesungen aus Polyacrylsaeurenitril bzw. seinen Mischpolymerisaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2814603A true US2814603A (en) | 1957-11-26 |
Family
ID=7571174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US392045A Expired - Lifetime US2814603A (en) | 1952-12-18 | 1953-11-13 | Dimethylformamide-aliphatic diester spinning solutions of polyacrylonitriles |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US2814603A (en(2012)) |
| BE (1) | BE525129A (en(2012)) |
| CH (1) | CH316128A (en(2012)) |
| DE (1) | DE926567C (en(2012)) |
| FR (1) | FR1080225A (en(2012)) |
| GB (1) | GB731789A (en(2012)) |
| NL (1) | NL83914C (en(2012)) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3437628A (en) * | 1966-09-06 | 1969-04-08 | Standard Oil Co | Impact resistant nitrile polymer articles |
| US9816310B2 (en) | 2014-01-13 | 2017-11-14 | Donatello Doors Inc. | Thermal break system and method for doors and windows |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1060781B (de) * | 1954-10-13 | 1959-07-02 | Eickhoff Maschinenfabrik Geb | Planetenausgleichgetriebe fuer Bandantriebe mit zwei vom Band hintereinander umschlungenen Antriebstrommeln |
| US2889192A (en) * | 1956-12-19 | 1959-06-02 | American Cyanamid Co | Method of treating cellulose-containing textile materials, materials so treated and diester composition therefor |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2589055A (en) * | 1950-04-29 | 1952-03-11 | Eastman Kodak Co | Mixtures comprising polyacrylonitrile and polyalkyl alpha-acylaminoacrylates and articles obtained therefrom |
-
0
- NL NL83914D patent/NL83914C/xx active
- BE BE525129D patent/BE525129A/xx unknown
-
1952
- 1952-12-18 DE DEV5267A patent/DE926567C/de not_active Expired
-
1953
- 1953-06-17 CH CH316128D patent/CH316128A/de unknown
- 1953-06-30 FR FR1080225D patent/FR1080225A/fr not_active Expired
- 1953-11-13 US US392045A patent/US2814603A/en not_active Expired - Lifetime
- 1953-12-16 GB GB35031/53A patent/GB731789A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2589055A (en) * | 1950-04-29 | 1952-03-11 | Eastman Kodak Co | Mixtures comprising polyacrylonitrile and polyalkyl alpha-acylaminoacrylates and articles obtained therefrom |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3437628A (en) * | 1966-09-06 | 1969-04-08 | Standard Oil Co | Impact resistant nitrile polymer articles |
| US9816310B2 (en) | 2014-01-13 | 2017-11-14 | Donatello Doors Inc. | Thermal break system and method for doors and windows |
| US9885210B2 (en) | 2014-01-13 | 2018-02-06 | Donatello Doors Inc. | Thermal break system and method for doors and windows |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1080225A (fr) | 1954-12-07 |
| GB731789A (en) | 1955-06-15 |
| CH316128A (de) | 1956-09-30 |
| BE525129A (en(2012)) | |
| DE926567C (de) | 1955-04-21 |
| NL83914C (en(2012)) |
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