US2825623A - Partially acetylated, cyanoethylated cotton textile fibers and process of acetylating cyanoethylated cotton textile fibers - Google Patents
Partially acetylated, cyanoethylated cotton textile fibers and process of acetylating cyanoethylated cotton textile fibers Download PDFInfo
- Publication number
- US2825623A US2825623A US519264A US51926455A US2825623A US 2825623 A US2825623 A US 2825623A US 519264 A US519264 A US 519264A US 51926455 A US51926455 A US 51926455A US 2825623 A US2825623 A US 2825623A
- Authority
- US
- United States
- Prior art keywords
- cotton
- fibers
- cyanoethylated
- nitrogen
- textile fibers
- 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
- 229920000742 Cotton Polymers 0.000 title claims description 47
- 239000000835 fiber Substances 0.000 title claims description 41
- 239000004753 textile Substances 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 12
- 230000000397 acetylating effect Effects 0.000 title claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 15
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 230000021736 acetylation Effects 0.000 claims description 9
- 238000006640 acetylation reaction Methods 0.000 claims description 9
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- JXBPSENIJJPTCI-UHFFFAOYSA-N ethyl cyanate Chemical group CCOC#N JXBPSENIJJPTCI-UHFFFAOYSA-N 0.000 claims description 6
- -1 HYDROXYL GROUPS Chemical group 0.000 claims description 5
- 150000002825 nitriles Chemical class 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 230000000717 retained effect Effects 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 1
- 238000004326 stimulated echo acquisition mode for imaging Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 229920002678 cellulose Polymers 0.000 description 7
- 239000001913 cellulose Substances 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000007278 cyanoethylation reaction Methods 0.000 description 5
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 4
- 229920002301 cellulose acetate Polymers 0.000 description 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/188—Monocarboxylic acids; Anhydrides, halides or salts thereof
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/13—Cyanoethylation of fibers
Definitions
- This invention relates to partially acetylated, cyanoethylated alpha-cellulose textile fibers, such as acetylated, cyanoethylated cotton yarn, having the original fiber structure and more particularly the invention relates to processes of producing such materials from partially cyanoethylated cotton textile fibers having the fiber structure of the original cotton and containing free hydroxyl groups, cyanoethyl ether groups and from about 3% to about of nitrogen, by weight, of said fibers, the nitrogen being nitnle nitrogen in the cyanoethyl groups thereof.
- Cellulose acetate fibers have achieved a very great use in many types of fabrics.
- the cellulose acetate has been strictly a synthetic fiber, that is to say, the acetylated cellulose is dissolved up in solvents and spun by extrusion from spinnerettes.
- monofilaments are produced which have the advantages of this type of fiber but also its disadvantages, such as a difierent hand, surface, characteristics and the like.
- a cyanoethylated alpha-cellulose such as cyanoethylated cotton yarn
- a cyanoethylated cotton textile fibers are partially acetylated by reacting them with acetic anhydride to introduce at least 0.3 mole of acetyl group per anhydroglucose unit of the cellulose, as shown in the example given post.
- the acetylation is insufiicient to acetylate all of the free hydroxyl groups thereof and insufiicient to destroy the fibrous structure of the cyanoethylated cotton fibers.
- the cyanoethylation is carried out until only a portion of the hydroxyl groups of the anhydroglucose cellulose unit are cyanoethylated.
- the amount of cyanoethylation should vary between that giving a nitrogen content of about 3% up to around 5%, by weight, of the cyanoethylated cotton fibers.
- Somewhat higher degrees of cyanoethylation may be utilized without losing all of the fiber characteristics.
- the acetyl groups are introduced into the cyanoethylated cotton the fiber structure is not materially changed and there is not produced a single solid filament such as the ordinary cellulose acetate fiber. As a result the good hand and other physical properties of the cotton fiber are retained.
- the present invention should not be confused with a procedure which has been proposed in the past in which ligno-cellulose, not alpha-cellulose, is cyanoethylated to the point that it loses entirely its fibrous structure and is then acetylated. This results in a product which has to be dissolved and spun exactly as ordinary cellulose acetate and has none of the properties of the original lignocellulose fiber. In other words, a product is produced which bears no relation to that of the present invention.
- acetylation process used is not critical and any standard procedures may be employed. As the particular acetylation process technique forms no part of the present invention, a single representative method only will be described in the following specific example.
- the tensile strength is markedly in excess of that of ordinary cotton yarn of the same character which has a tensile strength of about 600 grams, elongation is increased, and tenacity remains substantially the same.
- the tensile strength and elongation are substantially the same as for the cyanoethylated cotton before acetylation.
- the denier is somewhat greater showing a moderate degree of swelling.
- the partially acetylated, cyanoethylated cotton textile fibers having the fibrous structure of the original cotton and containing both acetyl groups and cyanoethyl ether groups in addition to free hydroxyl groups, the so modified cotton fibers having a tensile strength greater than that of the original cotton fibers and containing at least 0.3 mol of acetyl group per anhydroglucose unit thereof and from about 3% to about 5% of nitrogen, by weight, of said fibers, the nitrogen being present as nitrile nitrogen in said cyanoethyl groups thereof.
- the partially acetylated, cyanoethylated cotton textile fibers of claim 1 which contain approximately 0.3 mol of acetyl group per anhydroglucose unit thereof.
- the improved process which comprises partially acetylating the said partially cyanoethylated cotton textile fibers with acetic anhydride in an inert organic solvent to convert only part of the free hydroxyl groups thereof into acetyl groups and produce partially acetylated, cyanoethy
- a process of producing an acetylated material from cyanoethylated cotton textile fibers having a nitrogen content of approximately 3.3%, by weight, of said fibers, the nitrogen being present as nitrile nitrogen in said cyanoethyl groups thereof, and a degree of cyanoethylation insuflicient to substantially destroy the fibrous characteristics of the cotton which comprises acetylating said cyanoethylated cotton textile fibers at the temperature of a steam bath with an excess of a liquid consisting of equal parts of pyridine and acetic anhydride, the reaction being maintained until substantially complete and the acetylation proceeding to a point where the fiber characteristics of the cyanoethylated cotton are still retained, and then washing the so treated yarn free of acetic acid.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Artificial Filaments (AREA)
Description
2,825,623 Patented Mar. 4, 1958 PARTIALLY ACETYLATED, CYANOETHYLATED COTTON TEXTILE FIBERS AND PROCESS OF ACETYLATING CYANOETHYLA-TED COTTON TEXTILE FIBERS James R. Stephens and Lorence Rapoport, Stamford, Conn, assignors to American Cyanamid Company, New York, N. Y., a corporation of Maine No Drawing.- Application June 30, 1955' Serial No. 519,264
4' Claims. (Cl. 8-129).
This invention relates to partially acetylated, cyanoethylated alpha-cellulose textile fibers, such as acetylated, cyanoethylated cotton yarn, having the original fiber structure and more particularly the invention relates to processes of producing such materials from partially cyanoethylated cotton textile fibers having the fiber structure of the original cotton and containing free hydroxyl groups, cyanoethyl ether groups and from about 3% to about of nitrogen, by weight, of said fibers, the nitrogen being nitnle nitrogen in the cyanoethyl groups thereof.
Cellulose acetate fibers have achieved a very great use in many types of fabrics. However, the cellulose acetate has been strictly a synthetic fiber, that is to say, the acetylated cellulose is dissolved up in solvents and spun by extrusion from spinnerettes. As a result monofilaments are produced which have the advantages of this type of fiber but also its disadvantages, such as a difierent hand, surface, characteristics and the like.
According to the present invention, instead of acetylating cellulose, a cyanoethylated alpha-cellulose, such as cyanoethylated cotton yarn, is acetylated to introduce some acetyl groups and we have found that in this way it is possible to retain the general physical characteristics of cotton yarn and to improve certain properties. In doing so, the cyanoethylated cotton textile fibers are partially acetylated by reacting them with acetic anhydride to introduce at least 0.3 mole of acetyl group per anhydroglucose unit of the cellulose, as shown in the example given post. Further, as there shown, the acetylation is insufiicient to acetylate all of the free hydroxyl groups thereof and insufiicient to destroy the fibrous structure of the cyanoethylated cotton fibers.
Cyanoethylation of alphacellulose, such as cotton, has become of increased interest in recent years because of the desirable properties obtained, such as increased tensile strength, resistance to microorganisms, such as those causing mildew, increased abrasion and heat resistance, and the like. With alpha-cellulose, such as cotton, the cyanoethylation is carried out until only a portion of the hydroxyl groups of the anhydroglucose cellulose unit are cyanoethylated. In general, in order to retain the fiber structure and desirable properties, the amount of cyanoethylation should vary between that giving a nitrogen content of about 3% up to around 5%, by weight, of the cyanoethylated cotton fibers. Somewhat higher degrees of cyanoethylation may be utilized without losing all of the fiber characteristics. When the acetyl groups are introduced into the cyanoethylated cotton the fiber structure is not materially changed and there is not produced a single solid filament such as the ordinary cellulose acetate fiber. As a result the good hand and other physical properties of the cotton fiber are retained.
The present invention should not be confused with a procedure which has been proposed in the past in which ligno-cellulose, not alpha-cellulose, is cyanoethylated to the point that it loses entirely its fibrous structure and is then acetylated. This results in a product which has to be dissolved and spun exactly as ordinary cellulose acetate and has none of the properties of the original lignocellulose fiber. In other words, a product is produced which bears no relation to that of the present invention.
It is an advantage of the present invention that the acetylation process used is not critical and any standard procedures may be employed. As the particular acetylation process technique forms no part of the present invention, a single representative method only will be described in the following specific example.
Example 17.3 parts of 40 S72 cotton yarn cyanoethylated to a nitrogen content of 3.31% nitrogen, 200 parts of pyridine and 200 parts of acetic anhydride are heated on a steam bath with gentle stirring until acetylation under these conditions is substantially complete. This does not mean that all hydroxyl groups of the cellulose are acetylated but that the reaction has proceeded about as far as it will under the conditions set forth. The yarn is then removed from the acetylating bath, washed in running water until free of acetic acid and dried at 70 C. On analysis for acetyl groups the product showed the acetylation to a degree of .3 mole of acetyl group per anhydroglucose unit of the cellulose.
The product had an excellent hand and the following physical characteristics:
The tensile strength is markedly in excess of that of ordinary cotton yarn of the same character which has a tensile strength of about 600 grams, elongation is increased, and tenacity remains substantially the same. The tensile strength and elongation are substantially the same as for the cyanoethylated cotton before acetylation. The denier is somewhat greater showing a moderate degree of swelling.
We claim:
1. The partially acetylated, cyanoethylated cotton textile fibers having the fibrous structure of the original cotton and containing both acetyl groups and cyanoethyl ether groups in addition to free hydroxyl groups, the so modified cotton fibers having a tensile strength greater than that of the original cotton fibers and containing at least 0.3 mol of acetyl group per anhydroglucose unit thereof and from about 3% to about 5% of nitrogen, by weight, of said fibers, the nitrogen being present as nitrile nitrogen in said cyanoethyl groups thereof.
2. The partially acetylated, cyanoethylated cotton textile fibers of claim 1 which contain approximately 0.3 mol of acetyl group per anhydroglucose unit thereof.
3. As a process of producing partially acetylated, cyanoethylated cotton textile fibers having the fibrous structure of the original cotton and containing a plurality of cyanoethyl ether groups, acetyl groups and free hydroxyl groups, from partially cyanoethylated cotton textile fibers containing free hydroxyl groups and cyanoethyl ether groups, containing from about 3% to about 5% of nitrogen, by weight, of said cyanoethylated fibers, the nitrogen being present as nitrile nitrogen in said cyanoethyl groups thereof, and having the fiber structure of the original cotton and a tensile strength greater than that of the original cotton fibers, the improved process which comprises partially acetylating the said partially cyanoethylated cotton textile fibers with acetic anhydride in an inert organic solvent to convert only part of the free hydroxyl groups thereof into acetyl groups and produce partially acetylated, cyanoethylated cotton textile fibers having the fibrous structure of the original cotton and containing at least 0.3 mol of acetyl group per anhydroglucose unit thereof, said acetylation being insuflicient to substantially destroy the fibrous characteristics of the said cotton textile fiber, insulficient to materially weaken the tensile strength thereof and insufiicient to acetylate all of the free hydroxyl groups thereof, and recovering the partially acetylated cyanoethylated cotton textile fibers so obtained, the modified cotton textile fibers so produced being partially acetylated, cyanoethylated cotton textile fibers having the fibrous structure of the original cotton and a tensile strength greater than that of the original cotton fibers and containing both cyanoethyl ether groups and acetyl groups, in addition to free hydroxyl groups.
4. A process of producing an acetylated material from cyanoethylated cotton textile fibers having a nitrogen content of approximately 3.3%, by weight, of said fibers, the nitrogen being present as nitrile nitrogen in said cyanoethyl groups thereof, and a degree of cyanoethylation insuflicient to substantially destroy the fibrous characteristics of the cotton, which comprises acetylating said cyanoethylated cotton textile fibers at the temperature of a steam bath with an excess of a liquid consisting of equal parts of pyridine and acetic anhydride, the reaction being maintained until substantially complete and the acetylation proceeding to a point where the fiber characteristics of the cyanoethylated cotton are still retained, and then washing the so treated yarn free of acetic acid.
References Cited in the file of this patent UNITED STATES PATENTS Haller Oct. 17, 1933 Stallings June 14, 1949 OTHER REFERENCES
Claims (2)
1. THE PARTIALLY ACETYLATED, CYANOETHYLATED COTTON TEXTILE FIBERS HAVING THE FIBROUS STRUCTURE OF THE ORIGINAL COTTON AND CONTAINING BOTH ACETYL GROUPS AND CYANOETHYL ETHER GROUPS IN ADDITION TO FREE HYDROXYL GROUPS, THE SO MODIFIED COTTON FIBERS HAVING A TENSILE STRENGTH GREATER THAN THAT OF THE ORIGINAL COTTON FIBERS AND CONTAINING AT LEAST 0.3 MOL OF ACETYL GROUP PER ANHYDROGLUCOSE UNIT THEREOF AND FROM ABOUT 3% TO ABOUT 5* OF NITROGEN, BY WEIGHT, OF SAID FIBERS, THE NITROGEN BEING PRESENT AS NITRILE NITROGEN IN SAID CYANOETHYL GROUPS THEREOF.
4. A PROCESS OF PRODUCING AN ACETYLLATED MATERIAL FROM CYANOETHYLATED COTTON TEXTILE FIBERS HAVING A NITROGEN CONTENT OF APPROXIMATELY 3.3%, BY WEIGHT, OF SAID FIBERS, THE NITROGEN BEING PRESENT AS NITRILE NITROGEN IN SAID CYANOETHYL GROUPS THEREOF, AND A DEGREE OF CYANOTHYLATION INSUFFICIENT TO SUBSTANTIALLY DESTORY THE FIBROUS CHARACTERISTICS OF THE COTTON, WHICH COMPRISES ACETYLATING SAID CYANOETHYLATED COTTON TEXTILE FIBERS AT THE TEMPERATURE OR A STEAM BATH WITH AN EXCESS OF A LIQUID CONSISTING OF EQUAL PARTS OF PYRIDINE AND ACETIC ANHYDRIDE, THE REACTION BEING MAINTAINED UNTIL SUBSTANTIALLY COMPLETE AND THE ACETYLATION PROCEEDING TO A POINT WHERE THE FIBER CHARACTERICS OF THE CYANOTHYLATED COTTON ARE STILL RETAINED, AND THEN WASHING THE SO TREATED YARN FREE OF ACETIC ACID.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US519264A US2825623A (en) | 1955-06-30 | 1955-06-30 | Partially acetylated, cyanoethylated cotton textile fibers and process of acetylating cyanoethylated cotton textile fibers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US519264A US2825623A (en) | 1955-06-30 | 1955-06-30 | Partially acetylated, cyanoethylated cotton textile fibers and process of acetylating cyanoethylated cotton textile fibers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2825623A true US2825623A (en) | 1958-03-04 |
Family
ID=24067540
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US519264A Expired - Lifetime US2825623A (en) | 1955-06-30 | 1955-06-30 | Partially acetylated, cyanoethylated cotton textile fibers and process of acetylating cyanoethylated cotton textile fibers |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2825623A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1168384B (en) * | 1960-03-14 | 1964-04-23 | Deering Milliken Res Corp | Process for the partial cyanaethylation of cellulose-containing textiles |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1930895A (en) * | 1930-02-13 | 1933-10-17 | Chem Ind Basel | Cellulose esters and process of making same |
| US2473308A (en) * | 1946-12-24 | 1949-06-14 | Rohm & Haas | Treatment of cellulosic textiles with strong hydroxide and acrylonitrile |
-
1955
- 1955-06-30 US US519264A patent/US2825623A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1930895A (en) * | 1930-02-13 | 1933-10-17 | Chem Ind Basel | Cellulose esters and process of making same |
| US2473308A (en) * | 1946-12-24 | 1949-06-14 | Rohm & Haas | Treatment of cellulosic textiles with strong hydroxide and acrylonitrile |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1168384B (en) * | 1960-03-14 | 1964-04-23 | Deering Milliken Res Corp | Process for the partial cyanaethylation of cellulose-containing textiles |
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