USRE11659E - Raymond vidal - Google Patents
Raymond vidal Download PDFInfo
- Publication number
- USRE11659E USRE11659E US RE11659 E USRE11659 E US RE11659E
- Authority
- US
- United States
- Prior art keywords
- black
- dyeing
- coloring
- ammonia
- sulfur
- Prior art date
Links
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000004043 dyeing Methods 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 12
- 229910052717 sulfur Inorganic materials 0.000 description 12
- 239000011593 sulfur Substances 0.000 description 12
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N benzohydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 239000000835 fiber Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-Benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- YCIMNLLNPGFGHC-UHFFFAOYSA-N Catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 230000001264 neutralization Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VTWDKFNVVLAELH-UHFFFAOYSA-N 2-methylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C=CC1=O VTWDKFNVVLAELH-UHFFFAOYSA-N 0.000 description 2
- SPBDXSGPUHCETR-CVSKBELMSA-N Ivermectine Chemical group O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-CVSKBELMSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-M azane;chloride Chemical compound N.[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-M 0.000 description 2
- 230000005591 charge neutralization Effects 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- -1 hydroqninone Chemical compound 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000004753 textile 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
Definitions
- This invention has reference to an improved process of producing Incidentbblack, bluish-black, and black dycstutl's which can be used for dyeing textile fabrics without the use of mordants; and the invention consists of the process of producing these dyestuffs by subjecting ortho or para dioxybcnzcnes to the action of heat in the presence of sulfur and ble of producing the desired colors in the course of the reaction.
- the process can be carried out either in open or closed vessels at temperatures varying between 130 and 210eentigrade.
- the shade of the dyestuffs obtained varies according to the nature of the substances and temperature employed.
- dycstutl's are obtained when in the example before given the quinonc is replaced by tolu uinone or pyrocatcchin or the ammonia by a fatty amin, such as the mono or (ii methylamin.
- the various dyestuffs thus obtained may be used for dyeing either in their crude form or in their purified fornrby subjecting them to the before-described treatment with sulfuric acid; but in any case it is necessary for being used in dyeing that a suitable quantity of 50-- dium sullite be addcd,oi.' which, in practice, from two to three times the weight of the coloring-mattcr may be uscd.-
- coloring-matter derived from hydroquinone by heating with sulfur Witnessesi and ammonia, said coloring-matter being a EDWARD P. MACLEAN, dark mass, insoluble in water or acids, soln- ANTOINE ROUSSANNIGS, .Tr.
Description
UNITED STATES PATENT OFFICE.
RAYMOND VIDAL, OF PARIS, FRANCE.
BLACK DYE AND PROCESS OF MAKING SAME.
SPECIFICATION forming part of Iteissued Letters Patent No. 1 1,659, dated April 5, 18 98 Original No. 523,138, dated July 17, 1394. Application for reissue filed February 26, 1898. Serial Eo.888,908-
To to III/[107711 it may 1-0/1 ('II'IL:
Be it known that l, Ituuoxn Vino-u), aeitizen of the Republic of France, residing in Paris, France, have invented certain new and useful Improvements in lllaek Dyestuffs Dyeing without hlordauts, of which the fol lowing is a specification.
This invention has reference to an improved process of producing grecnislbblack, bluish-black, and black dycstutl's which can be used for dyeing textile fabrics without the use of mordants; and the invention consists of the process of producing these dyestuffs by subjecting ortho or para dioxybcnzcnes to the action of heat in the presence of sulfur and ble of producing the desired colors in the course of the reaction.
The process can be carried out either in open or closed vessels at temperatures varying between 130 and 210eentigrade. The shade of the dyestuffs obtained varies according to the nature of the substances and temperature employed.
The following proportions have given good results: twenty pounds of quinone,'ten pounds of sulfur, eight pounds of ammonia chlorid, twelve pounds of caustic soda. They are heated in a closed vessel for five hours at a temperature of 160 to 210 centigrade. At the end of this time the mass is permitted to cool. It is then pulverized and formsa dyestutl which can be used for dyeing without further purification.
\Vhen anaqucons'solution of these crude dyestuffs is subjected to the more.- or less extended action of sulfuric acid,va.rionsshades of colors mu y be obtained. The addition of sulfuric acid liberates sulfureted hydrogen, while simnltaneonsly the greater portion of the coloring-matter is precipitated from the solution. The precipitated coloring-matter is soluble in caustic soda and quiekly'soluble with a greenish-black shade in alkaline sultites, in which form vegetable fibers arcdycd in a grayish-blue, bluish-black, and black color. ()n the otherhand, the uncolorcd acid lit moi-,1 mm which the precipitate is separated by filtration ,dycs after neutralization by caustic soda either by the oxygen of the air or by oxidizing agents and imparts'an intensely violet-blue color. This coloring-matter, which is obtained only in small quantities, dyes the woolen fiber in the neutral bath violet-blue, in the acid-bath orseillc-rcdf '\\'hcn quinone is 'replaced by hydroquinone, the reaction takes place in an analogens manner. The resulting product is a dark mass insoluble in waterand inacids, soluble in alkalies and alkaline sulli tes. alkaline solutions are readily oxidized on exposure to air andihereupon become intensely black. 'lhcy dye unmordanted fiber 'a deep black, resistant to light, soaps, acid,
and friction. Other dycstutl's are obtained when in the example before given the quinonc is replaced by tolu uinone or pyrocatcchin or the ammonia by a fatty amin, such as the mono or (ii methylamin.
The various dyestuffs thus obtained may be used for dyeing either in their crude form or in their purified fornrby subjecting them to the before-described treatment with sulfuric acid; but in any case it is necessary for being used in dyeing that a suitable quantity of 50-- dium sullite be addcd,oi.' which, in practice, from two to three times the weight of the coloring-mattcr may be uscd.-
Having thus described my invention, I claim as now and desire to securo'by Let-tens Patcnt-- 1. The process herein described of produc ing greenish -black, bluishblack and black dyestuffs capable of dyeing the tlber'without niordants, which consistsin heating ortho or para dioxybenzcne, such as quinone, hydroqninone, toluquinone, or pyrocatechin in the presence of sulfur and of ammonia orof substances which are capable of generating: ammonia during the reaction, substantially as set forth.
The
2. The process herein described of pr lncing black dyestnff, by heating hydroqninone ble in alkalies and alkaline sulfites, the alka- [5 in presence of: sulfur and ammonia, substanline solutions being readily oxidiyed on expo- {daily as set forth. sure to ai r thereby becoming intensely black,
3. The described black coloring-inatters,- and capnbleof dyeing uninordanted cotton 5 derived from ortho or para dioxybenzene by fiber in black shades, substantially as set heating with sulfur and ammonia, said eolorforth. 2c
ing-matters being soluble in alkelies and al- In testimony whereof I have signed this 'kaline snl fites, and capable of dyeing unmorspecification in presence of two subscribing dented cotton fiber in black or blackish witnesses.
to shades, substantially as described.
4. The described coloring-matter derived from hydroquinone by heating with sulfur Witnessesi and ammonia, said coloring-matter being a EDWARD P. MACLEAN, dark mass, insoluble in water or acids, soln- ANTOINE ROUSSANNIGS, .Tr.
RAYMOND VIDAL.
Family
ID=
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