US2121337A - Dyeing mixed fibers - Google Patents
Dyeing mixed fibers Download PDFInfo
- Publication number
- US2121337A US2121337A US120904A US12090437A US2121337A US 2121337 A US2121337 A US 2121337A US 120904 A US120904 A US 120904A US 12090437 A US12090437 A US 12090437A US 2121337 A US2121337 A US 2121337A
- Authority
- US
- United States
- Prior art keywords
- dyeing
- fibers
- mixed
- metachrome
- dyes
- 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
- 238000004043 dyeing Methods 0.000 title description 17
- 239000000975 dye Substances 0.000 description 16
- 239000002585 base Substances 0.000 description 10
- 239000004744 fabric Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000002657 fibrous material Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 210000002268 wool Anatomy 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 229940123208 Biguanide Drugs 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 229910052804 chromium Inorganic materials 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- 239000004627 regenerated cellulose Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229920002955 Art silk Polymers 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- -1 dichloracetyl compound Chemical group 0.000 description 2
- NAPSCFZYZVSQHF-UHFFFAOYSA-N dimantine Chemical compound CCCCCCCCCCCCCCCCCCN(C)C NAPSCFZYZVSQHF-UHFFFAOYSA-N 0.000 description 2
- 229950010007 dimantine Drugs 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 229920000223 polyglycerol Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 1
- HONMCSLFRKBQHG-UHFFFAOYSA-N 1,3-diamino-1,3-diphenylurea Chemical compound C=1C=CC=CC=1N(N)C(=O)N(N)C1=CC=CC=C1 HONMCSLFRKBQHG-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- MNWJUMZPXYLPGT-UHFFFAOYSA-N 1-(diaminomethylidene)-2-octadecylguanidine Chemical compound CCCCCCCCCCCCCCCCCCN=C(N)N=C(N)N MNWJUMZPXYLPGT-UHFFFAOYSA-N 0.000 description 1
- QLOKJRIVRGCVIM-UHFFFAOYSA-N 1-[(4-methylsulfanylphenyl)methyl]piperazine Chemical compound C1=CC(SC)=CC=C1CN1CCNCC1 QLOKJRIVRGCVIM-UHFFFAOYSA-N 0.000 description 1
- GLKRSFJCYTXIOF-UHFFFAOYSA-N 2-octadecylguanidine Chemical compound CCCCCCCCCCCCCCCCCCN=C(N)N GLKRSFJCYTXIOF-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- SQSPRWMERUQXNE-UHFFFAOYSA-N Guanylurea Chemical compound NC(=N)NC(N)=O SQSPRWMERUQXNE-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 240000002329 Inga feuillei Species 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000009967 direct dyeing Methods 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 238000009963 fulling Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 230000009247 menarche Effects 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- QXYMVUZOGFVPGH-UHFFFAOYSA-N picramic acid Chemical compound NC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O QXYMVUZOGFVPGH-UHFFFAOYSA-N 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 150000003672 ureas Chemical class 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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
- D06P3/8219—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and amide 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
- D06P1/64—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
- D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
- D06P1/6494—Compounds containing a guanyl group R-C-N=, e.g. (bi)guanadine, dicyandiamid amidines
-
- 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
-
- 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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/14—Wool
- D06P3/20—Wool using mordant dyes using metallisable dyes
-
- 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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/64—Natural or regenerated cellulose using mordant dyes or metallisable dyes
Definitions
- Metach'rome Dyes (cf. index of Colour Index,' 1924 I), that are dyes, generally orthohydroxyazo' dyes, which are used in presence of metachrome mordant (ammonium sulfate and potassium chromate), thus forming the chromium complex compound of the dye on the fiber.
- metachrome mordant ammonium sulfate and potassium chromate
- dyes containing acid groups which in themselves have a certain dyeing ca-- pacity on vegetable fibrous material are known to be improved in their fastness to water and which dissolved in washing by treatment before or with compounds having ample quaternary bases of various kinds.
- the treatment is not applicable for lack of any afhnlty for vegetable fiber. From their constitutionfor example from that of Metachrome Brown (Colour Index, 1923 I No. 101), it could not be supposed that the formation of a sparingly soluble salt decisive for the fixation with a base of high molecular weight would proceed of itself.
- the present invention is based on the obserafter the dyeing cation activity, for exvation that Metachrome Dyes serve very well for dyeing fibrous materials consisting of, cellulose fibrous materials and wool in even shades, if
- the fibers are pre-treated with a cation-active compound of high molecular weight it is well known that some groups of dye cotton and other cellulosic material without premordanting the fibers, however, until yet no colorlessorganic compounds were known which are taken up from a dilute aqueous solution and bound by the fibers so that they can be removed neither by washing nor soaping.
- bases having an amnity for artificial fibers such organic bases of high molecular weight or the salts thereof are meant, water to form solutions of about 0.05 per cent. strength are absorbed by the fibers under corresponding exhaustion of the bath and remain on the fiber even when washing orsoaping the latter.
- Such bases are,'for instance, those which lean in their constitution towards the constitution of direct dyeing dyes, for example, the product of reaction of dichloracetylbenzldine with a trialkyl- Y which in itself has an amnity for artificial cellulosic fibers.
- the bases which contain polyether radicles and guanidine radicles or, are derived from guanidine.
- bases are made, for example, by the reaction of the chlorhydrin of: a polyglycerol containing, for example, 7 glycerol molecules, with stearyldimethylamine; cyandlamide with a base of high molecular weight, for instance oleylamine, dodecylamine or the like.
- a base of high molecular weight for instance oleylamine, dodecylamine or the like.
- Derivatives of high molecular weight of guanidlne, guanyl urea and the like have similar eflect.
- the mode of operation is preferably as follows: r
- the mixed fibers are treated for 1 to 2 hours at room temperature in a bath, for example of 1 per cent. strength, of the chloride of the basemolecular weight; the goods are then or by the reaction of dl-' or iminogroups is substituted by the dichloracetyl compound of squeezed, rinsed and dyed in the manner usual for dyeing wool with Metachrome Dyes.
- t'l'lfhe following examples illustrate the inven- Emmple 1.
- -4 mixed fabric of wool and copper artificial silk is treated for 1 to 2 hours at room temperature in a cold solution of 1 per cent. strength of a quaternary base obtainable by the reaction of the chlorhydrin of a polyglycerol containing about 'I molecules of glycerol with octadecyl-dimethylamine; the goods are squeezed and rinsed. They are then dyed for an hour and a half at the boil in a bath with 8 per-cent. of Metachrome Bordeaux B (Colour Index 1928, No. 107) and 3 per cent. of Metachrome Mordant. There is obtained adyeing uniform in .all fibers. Precipitations do not occur in-the -5 grams per liter of. oleyl-biguanide, squeezed and rinsed. It is then dyed at the boil of the general formula liquor.
- Ermnrlple 2 A mixed fabric of wool and viscose artificial silk is treated for an hour and a half at room temperature in a liquor which contains then for an hour and a half in a fresh bath with 4 per cent. of Metachrome Brown B (Colour Index 1923 I, No. 101) 4 per cent of Metachrome Mordant being added. A uniform dyeing of both kinds of fiber is obtained.
- the process for dyeing mixed fabrics or other mixed fibrous materials consisting of regenerated cellulose and animal fibers which comprises pre-treating the material with an amidine wherein R means an alkyl radicle with at least other then l0 carbon atoms and a: is a connecting radicle of the group consisting of NH, -o-, -NH-C-NH and then dyeing both the fibers of the mixed material in even shades with an ortho-hydroxyazo dye in the presence of a chromium mordant.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Description
. dyeing fabrics or menarche 21, 1938- a 7 re OFFICE DYEING mo mans Karl Brodersen.
Anhalt, German Works, 1110.,
. Delaware and Alfred Peters. Deccan-in asslgnors New York, N. Y a corporation of to General Aniline No Drawing. Application no is, 1937, Se-
rial No. 120,904. lin 1936 if on.
name Metach'rome Dyes (cf. index of Colour Index,' 1924 I), that are dyes, generally orthohydroxyazo' dyes, which are used in presence of metachrome mordant (ammonium sulfate and potassium chromate), thus forming the chromium complex compound of the dye on the fiber. On the other hand, dyes containing acid groups which in themselves have a certain dyeing ca-- pacity on vegetable fibrous material are known to be improved in their fastness to water and which dissolved in washing by treatment before or with compounds having ample quaternary bases of various kinds. In the case of Metachrome Dyes the treatment is not applicable for lack of any afhnlty for vegetable fiber. From their constitutionfor example from that of Metachrome Brown (Colour Index, 1923 I No. 101), it could not be supposed that the formation of a sparingly soluble salt decisive for the fixation with a base of high molecular weight would proceed of itself.
' The present invention-is based on the obserafter the dyeing cation activity, for exvation that Metachrome Dyes serve very well for dyeing fibrous materials consisting of, cellulose fibrous materials and wool in even shades, if
the fibers are pre-treated with a cation-active compound of high molecular weight it is well known that some groups of dye cotton and other cellulosic material without premordanting the fibers, however, until yet no colorlessorganic compounds were known which are taken up from a dilute aqueous solution and bound by the fibers so that they can be removed neither by washing nor soaping. In the following with the expression bases having an amnity for artificial fibers such organic bases of high molecular weight or the salts thereof are meant, water to form solutions of about 0.05 per cent. strength are absorbed by the fibers under corresponding exhaustion of the bath and remain on the fiber even when washing orsoaping the latter. I
Such bases are,'for instance, those which lean in their constitution towards the constitution of direct dyeing dyes, for example, the product of reaction of dichloracetylbenzldine with a trialkyl- Y which in itself has an amnity for artificial cellulosic fibers.
'of high Gey Jan 13.
amine or an analogous product of reaction of a tertiary base with ete diaminodiphenylurea.
Particularly advantageous are the bases which contain polyether radicles and guanidine radicles or, are derived from guanidine.
These bases are made, for example, by the reaction of the chlorhydrin of: a polyglycerol containing, for example, 7 glycerol molecules, with stearyldimethylamine; cyandlamide with a base of high molecular weight, for instance oleylamine, dodecylamine or the like. Derivatives of high molecular weight of guanidlne, guanyl urea and the like have similar eflect.
We mention, for ablc:--
Oleyl or stearylbiguanide of the formula or the corresponding compounds containing another higher alkyl radlcle with at least 10 carbon atoms or the biguanides in which the hydrogen Of the i alkyl or hydroxyalkyl.
Stearylguanidine of the formula CuHtr-NH-fi-NH:
and the corresponding alkyl and hydroxyalkyl derivatives.
The urea derivative of the constitution mHxr-O-fi-NH: I
instance, as especially suit- With the aid of these bases having an afiinity forartiflcial fibers it becomes possible to uniformly dye mixed fibers consisting of wool and cellulose wool in a single bath process. The fastness to washing, fulling and sweat of the dye- Inga, is considerably better than that imparted by other known processes. The application of Monochrome Dyes for the dyeing of such mixed fabrics has become possible owing to this invention.
The mode of operation is preferably as follows: r
The mixed fibers are treated for 1 to 2 hours at room temperature in a bath, for example of 1 per cent. strength, of the chloride of the basemolecular weight; the goods are then or by the reaction of dl-' or iminogroups is substituted by the dichloracetyl compound of squeezed, rinsed and dyed in the manner usual for dyeing wool with Metachrome Dyes.
t'l'lfhe following examples illustrate the inven- Emmple 1. -4 mixed fabric of wool and copper artificial silk is treated for 1 to 2 hours at room temperature in a cold solution of 1 per cent. strength of a quaternary base obtainable by the reaction of the chlorhydrin of a polyglycerol containing about 'I molecules of glycerol with octadecyl-dimethylamine; the goods are squeezed and rinsed. They are then dyed for an hour and a half at the boil in a bath with 8 per-cent. of Metachrome Bordeaux B (Colour Index 1928, No. 107) and 3 per cent. of Metachrome Mordant. There is obtained adyeing uniform in .all fibers. Precipitations do not occur in-the -5 grams per liter of. oleyl-biguanide, squeezed and rinsed. It is then dyed at the boil of the general formula liquor.
Ermnrlple 2.A mixed fabric of wool and viscose artificial silk is treated for an hour and a half at room temperature in a liquor which contains then for an hour and a half in a fresh bath with 4 per cent. of Metachrome Brown B (Colour Index 1923 I, No. 101) 4 per cent of Metachrome Mordant being added. A uniform dyeing of both kinds of fiber is obtained.
What we claim is:-
l. The process for dyeing mixed fabrics or other mixed fibrous materials consisting of regenerated cellulose and animal fibers which comprises pre-treating the material with an amidine wherein R means an alkyl radicle with at least other then l0 carbon atoms and a: is a connecting radicle of the group consisting of NH, -o-, -NH-C-NH and then dyeing both the fibers of the mixed material in even shades with an ortho-hydroxyazo dye in the presence of a chromium mordant.
2. The process .for dyeing mixed fabrics or mixed fibrous materials consisting of regenerated cellulose and animal fibers which comprises pre-treating the material with a biguanlde of the general formula r a-nn-c-mr-c-nm NH 11 wherein It means an alkyl radicle with at least 10 carbon atoms, and then dyeing both the fibers of the mixed material in even shades with an ortho-hydroxyazo dye in the presence of a chromium mordant.
3. The process for dyeing mixed fabrics or other mixed fibrous materials consisting of regenerated cellulose and animal fibers which comprises pretreating the material with oleyl-biguanide and then dyeing both the fibers of the mixed material in even shades with an ortho-hydroxyazo dye in the presence of a chromium mordant.
4. The process for dyeing mixed fabrics or other mixed fibrous materials consisting of regenerated cellulose and animal fibers which comprises pre-t'reating the material with oleyl-biguanide and then dyeing. both the fibers in even shades in the presence of ammonium sulfate and alkali metal chromate with the dye prepared by coupling diazotized picramic acid with metaphenylene-diamine.
KARL BRODERSEN. ALFRED PETERS.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2121337X | 1936-01-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2121337A true US2121337A (en) | 1938-06-21 |
Family
ID=7985924
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US120904A Expired - Lifetime US2121337A (en) | 1936-01-18 | 1937-01-16 | Dyeing mixed fibers |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2121337A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2434178A (en) * | 1948-01-06 | Metachkome dyeing with a colloid | ||
| US2442957A (en) * | 1942-09-19 | 1948-06-08 | American Cyanamid Co | Ethylene sulfide reaction products of guanylurea |
| US2443166A (en) * | 1945-01-13 | 1948-06-08 | American Cyanamid Co | Metachrome dyeing with cationic and non-ionic agents |
| US2448448A (en) * | 1942-06-08 | 1948-08-31 | Courtaulds Ltd | Dyeing of textile fibers containing nitrogen |
| US2453333A (en) * | 1942-09-19 | 1948-11-09 | American Can Cyanamid Company | Reaction of biguanide and ethylene sulfide |
| US2455897A (en) * | 1945-10-12 | 1948-12-07 | American Cyanamid Co | 1, 5-diarylbiguanides from aromatic amines and dicyanimide |
| US2573489A (en) * | 1944-11-17 | 1951-10-30 | Sandoz Ltd | Formaldehyde-dicyandiamide poly-hydroxypropylene-polyamine reaction product |
| FR2499386A1 (en) * | 1981-02-06 | 1982-08-13 | Cohen Daniel | CHILD SEAT |
-
1937
- 1937-01-16 US US120904A patent/US2121337A/en not_active Expired - Lifetime
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2434178A (en) * | 1948-01-06 | Metachkome dyeing with a colloid | ||
| US2448448A (en) * | 1942-06-08 | 1948-08-31 | Courtaulds Ltd | Dyeing of textile fibers containing nitrogen |
| US2442957A (en) * | 1942-09-19 | 1948-06-08 | American Cyanamid Co | Ethylene sulfide reaction products of guanylurea |
| US2453333A (en) * | 1942-09-19 | 1948-11-09 | American Can Cyanamid Company | Reaction of biguanide and ethylene sulfide |
| US2573489A (en) * | 1944-11-17 | 1951-10-30 | Sandoz Ltd | Formaldehyde-dicyandiamide poly-hydroxypropylene-polyamine reaction product |
| US2443166A (en) * | 1945-01-13 | 1948-06-08 | American Cyanamid Co | Metachrome dyeing with cationic and non-ionic agents |
| US2455897A (en) * | 1945-10-12 | 1948-12-07 | American Cyanamid Co | 1, 5-diarylbiguanides from aromatic amines and dicyanimide |
| FR2499386A1 (en) * | 1981-02-06 | 1982-08-13 | Cohen Daniel | CHILD SEAT |
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