USRE11178E - Place - Google Patents
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- Publication number
- USRE11178E USRE11178E US RE11178 E USRE11178 E US RE11178E
- Authority
- US
- United States
- Prior art keywords
- molecule
- acid
- soda
- sulpho
- pounds
- Prior art date
Links
- 239000002253 acid Substances 0.000 description 11
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 102000007469 Actins Human genes 0.000 description 1
- 108010085238 Actins Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- NRZRRZAVMCAKEP-UHFFFAOYSA-N Naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- NUIURNJTPRWVAP-UHFFFAOYSA-N Tolidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000009933 burial Methods 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000005002 naphthylamines Chemical class 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- -1 sulpho acids Chemical class 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Definitions
- one molecule of a tetra-so compound with one molecule of a naphthylamiue or a snlphoacid of a naphthylamine can be converted into soluble coloring-matter by neactmg on them with another molecule of a difiergnt amine or with a phenol: 7
- alpha-naphthsline sulpho-acid :n-alpha-naphthylamine sulpho-oead produced (which is a wootdye-stufi 1n deal!) is allowed to react in presence of acetate of soda on the tetrazoditolyl formed inthe usual manner by diazotizing thirty-two pounds of tolidine sulphate, or its equivalent of the base,
- Emmple 2 -l'he intermediate product produced in the samo manneras given in Ex ample ⁇ is reached upon with twenty-five pounds of bela'naphthylamine monosulphoacid soda salt in theplacoot the n'aphflnionic acid.
- tetrnm-bennole and its By eta-a0 bodies mean the followin homologues, tetrazo-oxydiphenyl, as well as the alkylized compounds, or the carbo or sulpho acids of the same.
- This coloring-matter appears as a brick-red powder, soluble in cold water, but much more soluble in hot water; soluble in concentrated acid, from which it is precipitated by water.
- the dyed fiber turns blue upon the addition of sulphuric acid, and brown upon the addition of acetic acid.
Description
UNITED STATES RUPERT GREVILLE-WILLIA'MS, oF ALBANY, NEW YORK, ASSIGNOR worse; I
PATENT OFFICE.
ALBANY COAL DYE AND CHEMICAL COMPANY, OF SAME.PLACE.'
MANUFACTURE OF MIXED AZO COLORS.
noxromin m ofleinuedmtsrl mt In. 11,178, am July 21, 1891.
Original Io. 418,145, dated Inn-her 28. 1389! it time fled 21, 1891- Burial In. 339,886.
"one molecule of a tetra-so compound with one molecule of a naphthylamiue or a snlphoacid of a naphthylamine can be converted into soluble coloring-matter by neactmg on them with another molecule of a difiergnt amine or with a phenol: 7
I have now found that a new class of intermediate bodies can be obtained by combining one molecule of uaphthaline-azo-naphthyla mine, or sulpho-acids of the same, with one molecule of a tetrazo compound, and that. these intermediate bodies can be converted into new and useful coloring-matters by reacting on them with another moleeuleof one of the naphtbylamines or asulpho-acid of the same.
The following are examples of how I carry out my process practically; 1 I
' Emanqile 1.Twenty-five pounds of naphthionste of soda are dissolved in fifty gallons of -w1.ter,and thirty pounds of muriatic acid,
22 Baume, are added. The precipitated free naphthionic acid is cooled with ice, seven pounds of nitrite of soda, dissolved in live times its weight of water, are run very slowly in. When the azotintion is complete, twentyfive pounds more-naphthionst'e of soda d18- ed in twen gallons of water are added 801' w pounds of aeetate'of and then fifteen 7 The mixture is stirred until the molecule of free na'phthionie acid is combined with the moleculeof ano-naphthalinesulpho-scnd. The reaction is complete when the whole product is transformed into a clear, bright, scarlet so- 1 tion. The alpha-naphthsline sulpho-acid :n-alpha-naphthylamine sulpho-oead produced (which is a wootdye-stufi 1n deal!) is allowed to react in presence of acetate of soda on the tetrazoditolyl formed inthe usual manner by diazotizing thirty-two pounds of tolidine sulphate, or its equivalent of the base,
dye-tests show no improvement. The temperature is then raised to boiling-point, and enough soda-lye added to convert the color 111(0 its soda salt. It is than precipitated with common salt, filtered 0E, pressed, and dried. The color dyes unmet-dented cotton a bright red in an alkaline or soap batlnand is fast to washing. 'lhe shade is similar to that of the color commercially known as benzo-purpurine 4'. ll," and has the following formula:
CH: son =1 ch rms 0,3 1;
! so ls 50 M on, NB,
.monosuIpho-acid) in presence of caustic soda,
instead of acetate of soda, asimilar body. is. obtained.
Emmple 2. -l'he intermediate product produced in the samo manneras given in Ex ample} is reached upon with twenty-five pounds of bela'naphthylamine monosulphoacid soda salt in theplacoot the n'aphflnionic acid.
'tetnm-diphenyl and its homologous, tetmmnaphflnliuefietrmstilbene, tritium-fluorine; tetraro-diphenolether. tetrnm-bennole and its By eta-a0 bodies I mean the followin homologues, tetrazo-oxydiphenyl, as well as the alkylized compounds, or the carbo or sulpho acids of the same. I
This coloring-matter appears as a brick-red powder, soluble in cold water, but much more soluble in hot water; soluble in concentrated acid, from which it is precipitated by water.
The dyed fiber turns blue upon the addition of sulphuric acid, and brown upon the addition of acetic acid.
Having now described my invention, what I claim, and desire to secure by Letters Patent, is+, i
1. he herein-describedprocess for the production of new azo coloring-matters, which process consists in combining one molecule of one of the herein-mentioned tetrazo comn'ds with one molecule of the herein-described naphthalineazocnaphthylemine or its 'sulpho compounds, and afterward actin g on the intermediate body thus formed with one molecule of one of the naphthylamiues or snlpho-acids of the same, substantially as set forth.
molecule of one :2. The process for producing new coloringmatters. by reversing the process in claim -1, by'combining the sulpho-ecids of the same, on the intermediate thus produced with the herein-described naphthaline-az naphthyla- 'mine or sulpho-acids of the same, substantially as set forth.
3. The substantive ezo dye-stuffs, produced as herein described,which are soluble in concentrated acids with a blue color,are precipitated from this solution water, are soluble in alkalies, and which have the property of dyeing nnmordanted cotton a. bright red color in an alkaline or soap bath, substantially as set forth.
' RUPERT GREVILLE-WILLIAMS.
Witnessest HENRY H. Lnnn,
22 Southampton J osnrn LAKE,
17 Gracechurch Street, London Edge, London.
tetrazo body first with one of the naphthylamines or and then reacting bythe addition of
Family
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