US2300589A - Animalizing cellulosic fibers - Google Patents
Animalizing cellulosic fibers Download PDFInfo
- Publication number
- US2300589A US2300589A US290220A US29022039A US2300589A US 2300589 A US2300589 A US 2300589A US 290220 A US290220 A US 290220A US 29022039 A US29022039 A US 29022039A US 2300589 A US2300589 A US 2300589A
- Authority
- US
- United States
- Prior art keywords
- animalizing
- fibers
- alkali
- soluble
- cellulosic 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
- 239000000835 fiber Substances 0.000 title description 22
- 239000003795 chemical substances by application Substances 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 210000002268 wool Anatomy 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 238000009987 spinning Methods 0.000 description 10
- 229920000297 Rayon Polymers 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- 239000003513 alkali Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical group NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 4
- 229920002994 synthetic fiber Polymers 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 230000000153 supplemental effect Effects 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
- D01F2/06—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from viscose
- D01F2/08—Composition of the spinning solution or the bath
Definitions
- an animalizing agent which is soluble in the spinning solution can be more easily and homogeneously distributed throughout the fiber than a pulverized and dispersed insoluble agent.
- the animalizing agents to be used according to our invention may be of various chemical structure. What they have in common are (1) the commbn characteristics of all animalizing agents, 1. e. they are high molecular, water insol uble basic substances, which increase the amnity of cellulosic fiber treated therewith to acid wool dyestuffs; and (2) theycontain one or more sulfonamldo groups by which they are rendered soluble in alkali lyes, for instance, in caustic soda lye.
- animalizing agents there may be mentioned, for examplareaction products from. aliphatic polyamines with arylsulioethyleneimides reaction products of chloroparaifinesuliochlorides obtainable according to the U. S. Patent No.
- Example 1 7.5% of a reaction product from polyethyleneimine and benzenesulioethyleneimide, (prepared ccording to Example 10 of the U. S. Patent No. 233,296 of Nelles et al. issued February 25, 1941) calculated on the weight of the cellulose, are dissolved in a small quantity of caustic sodalye and stirred into a viscose spinning solution. The solution is then worked up into viscose staple fibers as usual.
- The'fibers so obtained have good afiinity for acid wool dyestuffs and may be dyed alone or mixed with wool fibers, for instance, with Supranolbrillantred B (compare Schultz, Dyestufl Tables, vol. 2, 1932, p.
- Example 2 treatments are To a reaction product according to Example 10 tillation of the solvent, a tough, nearly colorless resin is obtained which, by dissolving in dilute aqueous alkali, filtering and precipitating with Very level dilute acetic acid, can be freed from small quantities oi alkali-insoluble products.
- the fibers so obtained ar dyed, alone or in mixture with animal fibers, by acid wool dyestuffs in very fast shades.
- Example 3 Parafilne is treated with sulfur dioxide and chlorine according to the method described in U. 8. Patent No. 2,046,090, until. the chlorine content of the resulting product is about 38%. 300 parts of this product are heatedfor hours to 115-120 C.- with 270 parts ethylenediamine (78%) in 150 parts butyl alcohol, similarly as described in the French Patent No. 709,626.
- Example 4 p-Aminobenzenesuli'oethyleneimide (melting point 129-130 C.) is prepared according to Gabriel, Ber. d. deutsch. chem. Ges. 28. Pa e 2933 by reactingp-acetylaminobenzenesuliochloride with ethyieneimine and saponiiying with aqueous alkali. By heating the imide for several hours to 100 C., a polymeric, infusible, colorless polyamide is obtained which is soluble in dilute aqueous alkali.
- Example 5 SOaN H1 which is worked up as usual.
- the fibers obtained therefrom are well dyed by acid wool dyestufis, for instance those mentioned in Example 1.
- Good tone-in-tone dyeings are obtained on mixed viscose-wool material in most cases.
- Process for increasing the aillnity of cellu:- losic fibers towards acid wool dyestuffs which comprises incorporating with the fibers highmolecular weight, water-insoluble. alkali-soluble sulfonamides containing in addition to the nitrogen of the sulfamide groups, basic nitrogen atoms.
- Process for increasing the amnity oi artificial cellulosic fibers towards acid wool dyestufis which comprises incorporating highmolecular weight, water-insoluble, alkali-soluble sulionamides containing in addition to the nitrogen oi' the sulfamide groups, basic nitrogen atoms, with an alkaline cellulose solution and precipitating the fibers from said solution.
- Process for increasing the affinity or artificial cellulosic fibers towards acid wool dyestufls which comprises incorporating highmolecular weight, water-insoluble, alkali-soluble sulfonamides containing in addition to the nitrogen of the sulfamide groups, basic nitrogen atoms with a viscose spinning solution.
- Cellulosic fibers having increased aflinity towards acid wool dyestuffs, said fibers having incorporated therewith high-molecular weight, water-insoluble, alkali-soluble sulfonamides containing in addition to the nitrogen of the suitamide groups, basic nitrogen atoms.
- Viscose artificial fibers having increased afiinity towards acid wool dyestufls, said fibers having incorporated therewith high-molecular weight, water-insoluble, alkali-soluble sulionamides containing in addition to the nitrogen of the sulfamide groups, basic nitrogen atoms.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Artificial Filaments (AREA)
- Coloring (AREA)
Description
Patented Nov. 3, 1942 UNITED STATES PATENTQOFFICE 2,300,589 snnuamzmc CELLULOSIC mans Johannes Nelles, Leverkusen-Schlebusch, and tto Bayer, Leverkusen I. G.-Werk, Germany, assignors, by mesne assignments, to General Aniline & Film Corporation, New York, N. Y., a
corporation of Delaware No Drawing. Application August 15, 1939, Serial No. 290,220. In Germany August 23, 1938 Claims. (01. 106-164) especially nitrogen, the high molecular character of which is caused by the presence of high molecular aliphatic radicals or by condensation or polymerization of low molecular basic compounds. It is also known that animalizing agents should be insoluble or difiicultly soluble in water, in order not to be removed from the fibers by wet treatments. In view of their insolubility in water and aqeuous liquids, animalizing agents were hitherto applied to the fibers or added to spinning solutions oi! artificial fibers in the form of solutions in organic solvents or in the form of aqueous dispersions.
We have now found an improvement in the art of animalizing which consists in employing. such v animalizing agents which, due to the presence of at least one sulfonamido group in their molecule, are soluble in alkali lyes. With the aid of these new animalizing agents it is now possible, for instance, to manufacture artificial fibers from viscose spinning solutions containing the animalizing agent homogeneously dissolved therein. Thereby the production of animalized artificial fibers is very much simplified because it is no longer necessary to prepare special solutions or dispersions of the animalizing agent and to apply such solutions or dispersions in special working steps to the material; also the disturbances are avoided which often occurred by. obstruction of pipes or nozzles of the spinning apparatus, when dispersions of an animalizing agent were added to the spinning solution. Furthermore, an animalizing agent which is soluble in the spinning solution, can be more easily and homogeneously distributed throughout the fiber than a pulverized and dispersed insoluble agent.
The animalizing agents to be used according to our invention may be of various chemical structure. What they have in common are (1) the commbn characteristics of all animalizing agents, 1. e. they are high molecular, water insol uble basic substances, which increase the amnity of cellulosic fiber treated therewith to acid wool dyestuffs; and (2) theycontain one or more sulfonamldo groups by which they are rendered soluble in alkali lyes, for instance, in caustic soda lye. As such animalizing agents there may be mentioned, for examplareaction products from. aliphatic polyamines with arylsulioethyleneimides reaction products of chloroparaifinesuliochlorides obtainable according to the U. S. Patent No. 2,046,090, with ammonia or ethylenediamine, condensation products of benezylchloridep-sulfochloride with 111- and polyamines, condensation products of naphthaleneand diphenyl-poly-(fl-chloroethylsulfamide) .with amines, reaction products .of polystyrene'sulfochlo-- ride with asymmetric dialkylethylenediamine, the formaldehyde condensation products of naphthalene-tri (as diethylethylenediaminesuliamide) and many others.
Our invention is furthermore illustrated by the following examples, the parts being by weight, if not otherwise stated:
Example 1 7.5% of a reaction product from polyethyleneimine and benzenesulioethyleneimide, (prepared ccording to Example 10 of the U. S. Patent No. 233,296 of Nelles et al. issued February 25, 1941) calculated on the weight of the cellulose, are dissolved in a small quantity of caustic sodalye and stirred into a viscose spinning solution. The solution is then worked up into viscose staple fibers as usual. The'fibers so obtained have good afiinity for acid wool dyestuffs and may be dyed alone or mixed with wool fibers, for instance, with Supranolbrillantred B (compare Schultz, Dyestufl Tables, vol. 2, 1932, p. 204), Anthralaneblue' G (compare 1. c., lrst supplemental vol., 1934, p. 68), 'piamondblack P23 (compare 1. 6., vol 1, 1931, p. 104). dyeings oi! good fastness to wet obtained. 0
Example 2 treatments are To a reaction product according to Example 10 tillation of the solvent, a tough, nearly colorless resin is obtained which, by dissolving in dilute aqueous alkali, filtering and precipitating with Very level dilute acetic acid, can be freed from small quantities oi alkali-insoluble products.
12% of this alkali-soluble animalizing agent are added to a viscose spinning solution which.
is worked up as usual. The fibers so obtained ar dyed, alone or in mixture with animal fibers, by acid wool dyestuffs in very fast shades.
Example 3 Parafilne is treated with sulfur dioxide and chlorine according to the method described in U. 8. Patent No. 2,046,090, until. the chlorine content of the resulting product is about 38%. 300 parts of this product are heatedfor hours to 115-120 C.- with 270 parts ethylenediamine (78%) in 150 parts butyl alcohol, similarly as described in the French Patent No. 709,626.
7% of the resulting animalizing agent, calculated on the weight of the cellulose, dissolved in aqueous alkali are' incorporated with a viscose staple fiber spinning solution. Fibers obtained therefrom are well dyed by acid wool dyestufls.
Example 4 p-Aminobenzenesuli'oethyleneimide (melting point 129-130 C.) is prepared according to Gabriel, Ber. d. deutsch. chem. Ges. 28. Pa e 2933 by reactingp-acetylaminobenzenesuliochloride with ethyieneimine and saponiiying with aqueous alkali. By heating the imide for several hours to 100 C., a polymeric, infusible, colorless polyamide is obtained which is soluble in dilute aqueous alkali.
4% of this product, dissolved in aqueous alkali, are added to a viscose spinning solution. The fibers obtained therefrom in the usual manner are oi. mat, wool-like appearance. They are easily dyed by acid wool dyestufi's, and the dyeings are oi good fastness. V
Example 5 SOaN H1 which is worked up as usual. The fibers obtained therefrom are well dyed by acid wool dyestufis, for instance those mentioned in Example 1. Good tone-in-tone dyeings are obtained on mixed viscose-wool material in most cases.
We claim:
1. Process for increasing the aillnity of cellu:- losic fibers towards acid wool dyestuffs which comprises incorporating with the fibers highmolecular weight, water-insoluble. alkali-soluble sulfonamides containing in addition to the nitrogen of the sulfamide groups, basic nitrogen atoms.
2. Process for increasing the amnity oi artificial cellulosic fibers towards acid wool dyestufis which comprises incorporating highmolecular weight, water-insoluble, alkali-soluble sulionamides containing in addition to the nitrogen oi' the sulfamide groups, basic nitrogen atoms, with an alkaline cellulose solution and precipitating the fibers from said solution.
3. Process for increasing the affinity or artificial cellulosic fibers towards acid wool dyestufls which comprises incorporating highmolecular weight, water-insoluble, alkali-soluble sulfonamides containing in addition to the nitrogen of the sulfamide groups, basic nitrogen atoms with a viscose spinning solution.
4. Cellulosic fibers having increased aflinity towards acid wool dyestuffs, said fibers having incorporated therewith high-molecular weight, water-insoluble, alkali-soluble sulfonamides containing in addition to the nitrogen of the suitamide groups, basic nitrogen atoms.
5. Viscose artificial fibers having increased afiinity towards acid wool dyestufls, said fibers having incorporated therewith high-molecular weight, water-insoluble, alkali-soluble sulionamides containing in addition to the nitrogen of the sulfamide groups, basic nitrogen atoms.
JOHANNES NELLES. OTTO BAYER.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2300589X | 1938-08-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2300589A true US2300589A (en) | 1942-11-03 |
Family
ID=7994121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US290220A Expired - Lifetime US2300589A (en) | 1938-08-23 | 1939-08-15 | Animalizing cellulosic fibers |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2300589A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2471039A (en) * | 1940-02-21 | 1949-05-24 | Orthner Ludwig | Manufacture of improved fibrous materials and the materials thus obtained |
| US2784107A (en) * | 1951-12-13 | 1957-03-05 | Courtaulds Ltd | Production of artificial filaments, threads and the like |
| US2892674A (en) * | 1955-05-27 | 1959-06-30 | Ici Ltd | Treatment of cellulosic materials |
| US2910341A (en) * | 1953-11-09 | 1959-10-27 | Du Pont | Spinning viscose |
| US3023182A (en) * | 1958-01-18 | 1962-02-27 | Kurashiki Rayon Co | Polyvinyl alcohol fibers of improved dyeability |
-
1939
- 1939-08-15 US US290220A patent/US2300589A/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2471039A (en) * | 1940-02-21 | 1949-05-24 | Orthner Ludwig | Manufacture of improved fibrous materials and the materials thus obtained |
| US2784107A (en) * | 1951-12-13 | 1957-03-05 | Courtaulds Ltd | Production of artificial filaments, threads and the like |
| US2910341A (en) * | 1953-11-09 | 1959-10-27 | Du Pont | Spinning viscose |
| US2892674A (en) * | 1955-05-27 | 1959-06-30 | Ici Ltd | Treatment of cellulosic materials |
| US3023182A (en) * | 1958-01-18 | 1962-02-27 | Kurashiki Rayon Co | Polyvinyl alcohol fibers of improved dyeability |
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