US2200452A - Method of producing cellulosic fibers having affinity for acid dyes - Google Patents
Method of producing cellulosic fibers having affinity for acid dyes Download PDFInfo
- Publication number
- US2200452A US2200452A US20704A US2070435A US2200452A US 2200452 A US2200452 A US 2200452A US 20704 A US20704 A US 20704A US 2070435 A US2070435 A US 2070435A US 2200452 A US2200452 A US 2200452A
- Authority
- US
- United States
- Prior art keywords
- cellulosic fibers
- fibers
- acid dyes
- affinity
- producing cellulosic
- 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 19
- 238000000034 method Methods 0.000 title description 10
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 title description 4
- 239000000980 acid dye Substances 0.000 title description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000009987 spinning Methods 0.000 description 5
- 229920002678 cellulose Polymers 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 229920002994 synthetic fiber Polymers 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 229920002955 Art silk Polymers 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- UPHWVVKYDQHTCF-UHFFFAOYSA-N octadecylazanium;acetate Chemical compound CC(O)=O.CCCCCCCCCCCCCCCCCCN UPHWVVKYDQHTCF-UHFFFAOYSA-N 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004380 Cholic acid Substances 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 1
- 229960002471 cholic acid Drugs 0.000 description 1
- 235000019416 cholic acid Nutrition 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 1
- GVHKXTXVQJKDEQ-UHFFFAOYSA-N dodecan-1-amine;2-hydroxypropanoic acid Chemical compound CC(O)C(O)=O.CCCCCCCCCCCCN GVHKXTXVQJKDEQ-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/645—Aliphatic, araliphatic or cycloaliphatic compounds containing amino groups
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/655—Compounds containing ammonium groups
- D06P1/66—Compounds containing ammonium groups containing quaternary ammonium groups
Definitions
- a good afiinity for said wool-dyestuffs is imparted to vegetable or artificial cellulosic fibers by incorporating in the fiber, according to the customary methods, a primary, secondary or tertiary amine of the general formula (R1, R2, R3)N or a quarternary ammonium base of the general formula: (R132 R: R4 N) OH, or a salt of any of these compounds.
- the amine or ammonium base should be taken up and retained by the fiber; this is the case when at least one of the residues represented by R1, R2, R3 and R4 comprises an aliphatic chain having eight or more carbon atoms.
- the remaining groups in the amine or ammonium base may' 'be hydrogen, aromatic residues or aliphatic residues containing less than eight carbon atoms.
- nitrogen atom of the amine or ammonium base 30 may itself be a member ofa ring system, that is to say it may belong to a heterocyclic ring.
- the compounds may be incorporated in the cellulosic fibers by impregnating the fiber with a solution or emulsion of the base or of a salt there- 35 of with an inorganic or organic acid.
- vAn addition of formaldehyde increases the fastness of the dyeings produced on fibers treated in accordance with the invention.
- the formaldehyde may be added to the impregnating bath or it may be 40 applied to the fibers in a separate bath.
- the amine or ammonium base or salt thereof may be incorporated in the spinning solution and the latter then spun according to the known methods. Since the compounds are contained in the artificial fibers thus produced, the same effect is attained. The effect is further improved by the simultaneous addition of proteins to the 50 spinning solution directly before the spinning in 'accordancewith the process described in the U. S. Patent 2,059,632 to Paul Esselmann and Karl Kfisslinger, one of these being also an in- The.
- cholic acid or acid amines such as formamide or acetamide.
- the amine or ammonium base or salt thereof may be incorporated inthe spinning solution or artificial fibers prepared according to the aforesaid patent may be subsequently treated with a solution or emulsion of the base or asalt thereof.
- Example 1 200 grams of stearylamine acetate are dissolved in 40 liters of water containing 5 per cent of formaldehyde, 2 kilos of cellulosic artificial silk or cotton are introduced into the bath thus prepared and frequently moved therein upwards and downwards during 15 to 20 minutes. Thematerial is then centrifuged and dried at 80 to 90 C.
- Example 2 The procedure is as in Example 1 with the exception that instead of stearylamine acetate there are used 20 grams of isopropyl; dodecylamine lactate or 200 grams of N-dodecyl- 1:3-propylene diamine formate.
- the term-cellulosic is intendedto include materials consisting of cellulose or cellulose hydrate, however, it shall exclude cellulose derivatives such as cellulose esters and ethers.
- a method of increasing the aflinity of cellulosic fibers for acid dyes comprisesimp regnating the undyed fibers with formaldehyde and an, aqueous liquid containing a compouhd selected from the group consisting of amines containing an aliphatic radical of more than 8 carbon atoms, tetra alkyl ammonium bases containing at least one radical with more than 8 carbon atoms and salts of these compounds, and drying the fibers thus treated.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
. Patented May 14,
PATENT, OFFICE METHOD OF PRODUCING OELLULOSIC FI- BERS HAVING AFFINITY FOR ACID DYES Karl Kiisslinger, Dessau, Hermann Klare, Wolfcn Kreis Bitterfeld, and Herbert Rein, Dessau, Germany, assignors to I. G. Farbenindustrie Aktiengesell'schaft, Germany Frankfort on the Main,
No Drawing. Application May 9, 1935, Serial In Germany May 15, 1934 2 Claims. (01. 8-116) One'of its objects is an improved process of this kind. Another object is to improve the capacity of vegetable or artificial cellulosic fibers to be dyed by acid dyes as used for dyeing wool.
6 Further objects will be seen from the detailed specification following hereafter.
According to this invention a good afiinity for said wool-dyestuffs is imparted to vegetable or artificial cellulosic fibers by incorporating in the fiber, according to the customary methods, a primary, secondary or tertiary amine of the general formula (R1, R2, R3)N or a quarternary ammonium base of the general formula: (R132 R: R4 N) OH, or a salt of any of these compounds. These substances react on the fiber with the dyestuif acid and thus fix the dyestuff to the cellulosic fiber, so that they give to cotton, artificial silk and other cellulosic fibers dyeing properties similar to those of animal fibers. It is essential for the purpose of the invention that the amine or ammonium base should be taken up and retained by the fiber; this is the case when at least one of the residues represented by R1, R2, R3 and R4 comprises an aliphatic chain having eight or more carbon atoms. The remaining groups in the amine or ammonium base may' 'be hydrogen, aromatic residues or aliphatic residues containing less than eight carbon atoms. nitrogen atom of the amine or ammonium base 30 may itself be a member ofa ring system, that is to say it may belong to a heterocyclic ring.
The compounds may be incorporated in the cellulosic fibers by impregnating the fiber with a solution or emulsion of the base or of a salt there- 35 of with an inorganic or organic acid. vAn addition of formaldehyde increases the fastness of the dyeings produced on fibers treated in accordance with the invention. The formaldehyde may be added to the impregnating bath or it may be 40 applied to the fibers in a separate bath.
Instead of introducing the compounds subsequently to the production of the artificial fibers, the amine or ammonium base or salt thereof may be incorporated in the spinning solution and the latter then spun according to the known methods. Since the compounds are contained in the artificial fibers thus produced, the same effect is attained. The effect is further improved by the simultaneous addition of proteins to the 50 spinning solution directly before the spinning in 'accordancewith the process described in the U. S. Patent 2,059,632 to Paul Esselmann and Karl Kfisslinger, one of these being also an in- The.
ventor of' the present invention. These proteins may be fixed by the addition to the spinning solution of suitable compounds, for instance,
cholic acid or acid amines such as formamide or acetamide. In this case also the amine or ammonium base or salt thereof may be incorporated inthe spinning solution or artificial fibers prepared according to the aforesaid patent may be subsequently treated with a solution or emulsion of the base or asalt thereof.
The following examples illustrate the invention: v
Example 1.-200 grams of stearylamine acetate are dissolved in 40 liters of water containing 5 per cent of formaldehyde, 2 kilos of cellulosic artificial silk or cotton are introduced into the bath thus prepared and frequently moved therein upwards and downwards during 15 to 20 minutes. Thematerial is then centrifuged and dried at 80 to 90 C.
Example 2.The procedure is as in Example 1 with the exception that instead of stearylamine acetate there are used 20 grams of isopropyl; dodecylamine lactate or 200 grams of N-dodecyl- 1:3-propylene diamine formate.
The term-cellulosic is intendedto include materials consisting of cellulose or cellulose hydrate, however, it shall exclude cellulose derivatives such as cellulose esters and ethers.
What we claim is:
1.-A method of increasing the aflinity of cellulosic fibers for acid dyes which method comprises treating the undyed fibers with formaldehyde and an aqueous liquid containing a com; pound selected from the group consisting of amines containing an aliphatic radical of more than 8- carbon atoms, tetra alkyl ammonium bases containing at least one radical with more than 8 carbon atoms and salts of these compounds, and drying the fibers thus treated.
2. A method of increasing the aflinity of cellulosic fibers for acid dyes which method comprisesimp regnating the undyed fibers with formaldehyde and an, aqueous liquid containing a compouhd selected from the group consisting of amines containing an aliphatic radical of more than 8 carbon atoms, tetra alkyl ammonium bases containing at least one radical with more than 8 carbon atoms and salts of these compounds, and drying the fibers thus treated.
: KARL Kdssmwna.
HERMANN KI..AR.E. HERBERT REIN.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2200452X | 1934-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2200452A true US2200452A (en) | 1940-05-14 |
Family
ID=7989747
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US20704A Expired - Lifetime US2200452A (en) | 1934-05-15 | 1935-05-09 | Method of producing cellulosic fibers having affinity for acid dyes |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2200452A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2448125A (en) * | 1943-03-26 | 1948-08-31 | Ciba Ltd | Amide derivatives and process of making same |
| US2580491A (en) * | 1950-08-08 | 1952-01-01 | Jr Kyle Ward | Reducing the crystallinity of native fibrous cellulosic material |
-
1935
- 1935-05-09 US US20704A patent/US2200452A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2448125A (en) * | 1943-03-26 | 1948-08-31 | Ciba Ltd | Amide derivatives and process of making same |
| US2580491A (en) * | 1950-08-08 | 1952-01-01 | Jr Kyle Ward | Reducing the crystallinity of native fibrous cellulosic material |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2131145A (en) | Process for increasing the reactivity of naturally or artificially shaped articles or materials and product obtained thereby | |
| US2083122A (en) | Manufacture of artificial filaments, threads, films, and the like | |
| US2350188A (en) | Textile treatment | |
| US3038820A (en) | Process for imparting a soft feel to textile fibers | |
| US2345110A (en) | Process for improving fibrous material and the material treated by such a process | |
| US2004476A (en) | Dyeing of textiles | |
| US4072464A (en) | Epoxypropyl ammonium salt and boric acid assisted dyeing process | |
| US2200452A (en) | Method of producing cellulosic fibers having affinity for acid dyes | |
| US2183754A (en) | Process of dyeing | |
| US2017119A (en) | Treatment of textile and other materials | |
| US2203493A (en) | Treatment of cellulosic material | |
| US2131121A (en) | Process of increasing the fastness of dyeings | |
| US2263387A (en) | Process of dyeing | |
| US2186894A (en) | Treating fibrous materials | |
| GB496234A (en) | Process for improving artificial silk fabrics | |
| US3009761A (en) | Polyquaternary ammonium compounds | |
| US1957493A (en) | Treatment of textile and other materials | |
| US2448448A (en) | Dyeing of textile fibers containing nitrogen | |
| US2307973A (en) | Dyeings | |
| US2148655A (en) | Coloration of textile materials | |
| US2364725A (en) | Process for improving the dyeings | |
| GB486010A (en) | Improvements in dyeing textile fibres | |
| GB440647A (en) | Improvements relating to vegetable and artificial cellulosic fibres | |
| US1856033A (en) | Artificial forms or threads fast to water and easily dyed and process of making same | |
| GB501913A (en) | Process for dyeing cellulose and cellulose derivative-fibrous material with acid dyestuffs |