US1875452A - Max habtmann - Google Patents
Max habtmann Download PDFInfo
- Publication number
- US1875452A US1875452A US1875452DA US1875452A US 1875452 A US1875452 A US 1875452A US 1875452D A US1875452D A US 1875452DA US 1875452 A US1875452 A US 1875452A
- Authority
- US
- United States
- Prior art keywords
- fibrous materials
- fibers
- dyed
- solvents
- absence
- 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
- 239000002657 fibrous material Substances 0.000 description 36
- 239000000835 fiber Substances 0.000 description 30
- 238000000034 method Methods 0.000 description 30
- 229920000742 Cotton Polymers 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- 239000000126 substance Substances 0.000 description 22
- 150000002513 isocyanates Chemical class 0.000 description 20
- 210000002268 Wool Anatomy 0.000 description 14
- 229920002678 cellulose Polymers 0.000 description 14
- 239000001913 cellulose Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 235000013311 vegetables Nutrition 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 10
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 10
- DGTNSSLYPYDJGL-UHFFFAOYSA-N Phenylisocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 150000002170 ethers Chemical class 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000004043 dyeing Methods 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N [N-]=C=O Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 2
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 2
- JRVZITODZAQRQM-UHFFFAOYSA-N 1-isocyanato-2-nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1N=C=O JRVZITODZAQRQM-UHFFFAOYSA-N 0.000 description 2
- 240000008564 Boehmeria nivea Species 0.000 description 2
- 240000000491 Corchorus aestuans Species 0.000 description 2
- 235000011777 Corchorus aestuans Nutrition 0.000 description 2
- 235000010862 Corchorus capsularis Nutrition 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 229940032330 Sulfuric acid Drugs 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- -1 aliphatic isocyanates Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229920003086 cellulose ether Polymers 0.000 description 2
- 238000005039 chemical industry Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical class CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 230000002045 lasting Effects 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000010446 mirabilite Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000004627 regenerated cellulose Substances 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 230000000717 retained Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000009738 saturating Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical class NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
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
- D06M13/322—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 nitrogen
- D06M13/395—Isocyanates
-
- 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
- Y10S8/11—Isocyanate and carbonate modification of fibers
Definitions
- the present invention relates to new fibrous materials. It comprises the manufacture of the new fibrous materials, the fibrous materials themselves, and the application thereof in the textile industry, such as for instance for the production of mixed fabrics and multi-colored materials.
- Such organic isocyanates are for example the phenylisocyanates, the naphthyl-isoc anates, the nitro-phenyl-isocyanates, furt er aliphatic isocyanates, such as the methyl or ethyl-isocyanates.
- Such fibers are for instance the fibers o vegetable origin, such as cotton, linen jute, ramie, etc.-, further the artificial fibers from so-called regenerated cellulose (viscose silk and cuprammonium silk), and the fibersof animal origin, such as wool and silk.
- animal fibers such as wool and silk
- isocyanates with retention of their structure but with profound change in the behavior of the treated material towards dyestuffs.
- Wool loses its
- the treatment of fibrous materials with organic isocyanates may be performed by aflinity for the typi-' saturating the previously dried goods with the isocyanate and allowing them to remain therein at the ordinar temperature or at araised temperature.
- atalysts such as pyridine, zinc chloride or the like, may be added.
- the present invention is distinguished in that the fibrous materials treated are only affected insofar as their physical and chemical properties are concerned, their fibrous structure remaining unchanged, whereas in the known process the purpose was the dissolution of the cellulose and its reprecipitation in the form of a carbamic acid ester. Moreover, the present invention is not limited to cellulose but is applicable also to animal fibers.
- Ewample 1 in a vacuum and the yarn is freed by washing with hot alcohol from the residual pyridine and from some diphenyl-urea which has been formed.
- the yarn is externally uni changed but has increased in weight up to 30 per cent. and has a nitrogen content of 25 per cent. It is strongly dyed b basic dyestuffs without a mordant. Also y acetate silk dyestuffs the mode of dyeing'being similar to that usual for this fiber, whereas direct dyestufi's are scarcely absorbed.
- This yarn is no longer dyed by acid dyestuffs, such as dyestufi- No. 66, Schultz, Farbstofitabellen, 6th Edition.
- Example 7 Wool fiber treated as descri the same quantity of untreated wool, it so is introduced into a dye-bath containing 2 per cent. of acid-dyestufi for exam le paraaminoacetanilidwacetyl- -acid, Sc ultz, 5th Edition, No. 66), 10 per cent. of Glaubers' 7 salt and 2 er cent. of sulfuricacid at 66 B. as at 95 the treatment lasting for 1 hour.
- the yarn is amtgle 3, remains undyed when, in admixture W1
- the wool on the other hand, is dyed a deep blue red.
- What I claim is 1. Process of altering the chemical properties of natural fibrous materials, comprising treating fibrous materials with organic isocyanates in the absence of solvents.
- Process of altering the chemical prop- 10g erties ofnatural fibrous materials consisting in treating fibers of vegetable origin which, contrary to esters and ethers of cellulose can be dyed without difiiculty with dyestuffs containmg more than one sulfo group, with organic isocynates in the absence of solvents and inpresence of a tertiary base as catalyst.
Description
I cal wool dyestufis.
Patented Sept. 6, 1932 UNITED STATES PATE NT OFFICE MAX HABTMANN, OF RIEHEN, NEAR BASE, SWITZERLAND, ASSIGNORTO THE FIRE 0F SOCIETY OF CHEMICAL INDUSTRY IN BASLE, OF
BASEL, SWITZERLAND FIBBOUS MATERIAL AND PROCESS OF MAKING SAME No Drawing. Application filed July 27, 1929, Serial No. 381,8 88, and in Switzerland Auguste, 1928.
The present invention relates to new fibrous materials. It comprises the manufacture of the new fibrous materials, the fibrous materials themselves, and the application thereof in the textile industry, such as for instance for the production of mixed fabrics and multi-colored materials.
It has been found that quite generally new dyeing properties are imparted to fibrous'materials of vegetable, animal, or artificial origin, by treating these materials with organic isocyanates of the general formula R.N=C=O, wherein R is any organic residue in the absence of solvents,
Such organic isocyanates are for example the phenylisocyanates, the naphthyl-isoc anates, the nitro-phenyl-isocyanates, furt er aliphatic isocyanates, such as the methyl or ethyl-isocyanates.
This method is particularly valuable for the treatment of such fibers which, contrary to cellulose ethers and esters, are dyed without dilficulty with dyestuffs containing more than one sulfo grou Such fibers are for instance the fibers o vegetable origin, such as cotton, linen jute, ramie, etc.-, further the artificial fibers from so-called regenerated cellulose (viscose silk and cuprammonium silk), and the fibersof animal origin, such as wool and silk.
For example, by the action of phenylisocyanate on vegetable fiber, such as cotton, in the piece or in the form of yarn, there is obtained a product whose outer structure is retained but whose properties in respect of dyestuffs have been profoundly changed. By this treatment/the cotton loses its afiinity to substantive cotton dyestuffs while it is easily dyed by acetate silk dyesufis, for instance by insoluble azo-dyestuifs and amino-anthraquinones. Like cotton or other vegetable fibers, w
animal fibers, such as wool and silk, can also be treated with isocyanates with retention of their structure but with profound change in the behavior of the treated material towards dyestuffs. Wool loses its The treatment of fibrous materials with organic isocyanates may be performed by aflinity for the typi-' saturating the previously dried goods with the isocyanate and allowing them to remain therein at the ordinar temperature or at araised temperature. atalysts, such as pyridine, zinc chloride or the like, may be added.
, mg process or printing process multi-colored materials are obtained. The possibility of producing such'efiects even exists in the case of piece goods, if the latter have been treated locally with an isocyanate. i
' From the process described in the specification No. 1,357,450 the present invention is distinguished in that the fibrous materials treated are only affected insofar as their physical and chemical properties are concerned, their fibrous structure remaining unchanged, whereas in the known process the purpose was the dissolution of the cellulose and its reprecipitation in the form of a carbamic acid ester. Moreover, the present invention is not limited to cellulose but is applicable also to animal fibers.
- The following examples illustrate the invention:--
Ewample 1 in a vacuum and the yarn is freed by washing with hot alcohol from the residual pyridine and from some diphenyl-urea which has been formed. The yarn is externally uni changed but has increased in weight up to 30 per cent. and has a nitrogen content of 25 per cent. It is strongly dyed b basic dyestuffs without a mordant. Also y acetate silk dyestuffs the mode of dyeing'being similar to that usual for this fiber, whereas direct dyestufi's are scarcely absorbed.
' 1 with exclusion of moisture.
then boiled with alcohol, whereby a product Example 3 Woolen yarn wnich has been dried in a vacuum is saturated with plrenylisocyanate 80 that it contains an equal weight thereof and heated for 48 hours in the water-bath is obtained whose structure is unaltered and which has suffered a considerable increase in weight, for instance up to 50 per cent. This yarn is no longer dyed by acid dyestuffs, such as dyestufi- No. 66, Schultz, Farbstofitabellen, 6th Edition. Example 4 The fiber, treated as described in Example 1, is mixed with 4 arts of untreated cotton and dyed in a dyeath prepared with 2 per cent. of direct dyestuff (such as No. 424, Schultz, Farbstofitabellen, 5th Edition) and per cent. of Glaubers salt (calculated on the total weight of the fibrous material), the dveing being continued for 1 hour at 90 C.
ereas the cotton is dyed as usual a powerful blue, the treated fibers remain nearly Ema/mp1s 5 Goods'treated as described in Example 1 are entered into a dye-bath'which contains 1 w per cent of solid green and .1 per cent. of
acetic acid of 40 per cent, strength, and aiter I hour the tem rature of the bath is grad-' ually raised to 0 C. There is obtained a powerful green dyeing.
Example 7 Wool fiber, treated as descri the same quantity of untreated wool, it so is introduced into a dye-bath containing 2 per cent. of acid-dyestufi for exam le paraaminoacetanilidwacetyl- -acid, Sc ultz, 5th Edition, No. 66), 10 per cent. of Glaubers' 7 salt and 2 er cent. of sulfuricacid at 66 B. as at 95 the treatment lasting for 1 hour.
The yarn is amtgle 3, remains undyed when, in admixture W1 The wool, on the other hand, is dyed a deep blue red.
What I claim is 1. Process of altering the chemical properties of natural fibrous materials, comprising treating fibrous materials with organic isocyanates in the absence of solvents.
2. Process of altering the chemical properties of natural fibrous materials, consisting in treating fibrous materials with organic P isocyanates in the absence of solvents and in the presence of a tertiary base as catalyst.
3. Process of altering the chemical properties of natural .fibrous materials, comprising treating with organic isocyanates in the absence of solvents such fibers which, contrary to esters and ethers of cellulose, can be dyed without difiiculty with dyestufis containing more than one sulfo group.
4. Process of altering the chemical properties of natural fibrous materials, consisting in treatin with organic isocyanates in the absence 0 solvents and in presence of a tertiary base as catalyst such fibers which, contrary to esters and ethers of cellulose, can be dyed without difiiculty with dyestuffs contaimng more than one sulfo group.
5. Process of altering the chemical properties of natural fibrous materials, comprising treating fibers of vegetable origin which, contrary to esters and ethers of cellulose, can
- be dyed without difficulty with dyestufis containing more than one sulfo group, with organic isocynates in the absence of solvents.
6. Process of altering the chemical prop- 10g erties ofnatural fibrous materials, consisting in treating fibers of vegetable origin which, contrary to esters and ethers of cellulose can be dyed without difiiculty with dyestuffs containmg more than one sulfo group, with organic isocynates in the absence of solvents and inpresence of a tertiary base as catalyst.
7. Process of altering'the chemical properties of natural fibrous materials, comprising treating cotton with organic isocyanates in the absence of solvents.
8. Process of; altering the chemical prop-' erties of natural fibrous materials, consisting in treating cotton with organic isocyanates in the absence of solvents and in presence of a tertiary base as catalyst.
9. Process of altering the chemical properties or natural fibrous materials, COIDPIIS- ingtreating cotton with phenyl-isocyanate in the absence of solvents.
' 10. Process of'altering the chemical propertles 01 natural fibrous materials, conslsting in treating cotton with phenyl-isocyanate in the absence of solvents and in presence of a Y tertiary base as catalyst. 125
. In witness whereof I have hereunto signed A my name this 18th day of July, 1929.
MAX HARTMANN.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1875452A true US1875452A (en) | 1932-09-06 |
Family
ID=3424240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US1875452D Expired - Lifetime US1875452A (en) | Max habtmann |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1875452A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2468716A (en) * | 1947-04-16 | 1949-04-26 | American Cyanamid Co | Treatment of hydrogen-donor textile materials and products thereof |
| US2597025A (en) * | 1947-09-13 | 1952-05-20 | Armour & Co | Potentially reactive aromatic diisocyanate-water resinous reaction product and method of preparing |
| US2795517A (en) * | 1953-12-02 | 1957-06-11 | Ici Ltd | Modification of the properties of fibrous materials |
| US3145074A (en) * | 1962-10-02 | 1964-08-18 | Nathan H Koenig | Isocyanate treatment of wool in presence of methylpyrrolidone |
-
0
- US US1875452D patent/US1875452A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2468716A (en) * | 1947-04-16 | 1949-04-26 | American Cyanamid Co | Treatment of hydrogen-donor textile materials and products thereof |
| US2597025A (en) * | 1947-09-13 | 1952-05-20 | Armour & Co | Potentially reactive aromatic diisocyanate-water resinous reaction product and method of preparing |
| US2795517A (en) * | 1953-12-02 | 1957-06-11 | Ici Ltd | Modification of the properties of fibrous materials |
| US3145074A (en) * | 1962-10-02 | 1964-08-18 | Nathan H Koenig | Isocyanate treatment of wool in presence of methylpyrrolidone |
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