USRE11231E - Werke - Google Patents
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- USRE11231E USRE11231E US RE11231 E USRE11231 E US RE11231E
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- US
- United States
- Prior art keywords
- acid
- weight
- coloring
- parts
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- 239000002253 acid Substances 0.000 description 26
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
- 235000002639 sodium chloride Nutrition 0.000 description 4
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 210000002268 Wool Anatomy 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 2
- OIDPCXKPHYRNKH-UHFFFAOYSA-J Chrome alum Chemical compound [K]OS(=O)(=O)O[Cr]1OS(=O)(=O)O1 OIDPCXKPHYRNKH-UHFFFAOYSA-J 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229940037003 alum Drugs 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- ZJGXVJZARHWMSD-UHFFFAOYSA-N 3-diazo-2H-naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)C(=[N+]=[N-])C=C21 ZJGXVJZARHWMSD-UHFFFAOYSA-N 0.000 description 1
- 241001156002 Anthonomus pomorum Species 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 241000270299 Boa Species 0.000 description 1
- GIGZRLFGWCDIIB-UHFFFAOYSA-N C(C)ONC1=CC=C(C2=CC=C(NOCC)C=C2)C=C1 Chemical compound C(C)ONC1=CC=C(C2=CC=C(NOCC)C=C2)C=C1 GIGZRLFGWCDIIB-UHFFFAOYSA-N 0.000 description 1
- 235000009025 Carya illinoensis Nutrition 0.000 description 1
- 241001453450 Carya illinoinensis Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L Copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L Copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- RUDCBGCNXOSCTI-UHFFFAOYSA-N N-methoxy-4-[4-(methoxyamino)phenyl]aniline Chemical compound C1=CC(NOC)=CC=C1C1=CC=C(NOC)C=C1 RUDCBGCNXOSCTI-UHFFFAOYSA-N 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N O-Anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 235000015450 Tilia cordata Nutrition 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229950010935 dioxyline Drugs 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BHKPHCKISVSDGV-UHFFFAOYSA-N quinolin-8-yl benzoate Chemical compound C=1C=CC2=CC=CN=C2C=1OC(=O)C1=CC=CC=C1 BHKPHCKISVSDGV-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
Definitions
- This-novel body is'deri'vec'l from'a new n'aph UNITED STATES PATENT OFFICE.
- HANS KUZEL on noo1.is'r-oN-TnE-MMN,GER AnY, Asslenon TO THE 1mm;- WERKE, VORMALS MEISTER, LUCIUS a BRUNING, OF, SAME PLACE.
- My inventior t relates to the manufacture of azo coloringmiatter ranging in color from bluishsred to "violet, derived from the hereindescribed diazonaphthaline disulphonic acid, characterized, as above mentioned, by com- 5 bining said acid or its salts with diazo bodies and adapted for dyeing wool in greatly differing shades of color, depending upon the use of acids, such'as sulphuric acid or bisulphates or acids in combination with metallic mordants, such as alum, chrome alum, or alkaline chromates.
- Example L-Ninetytn ree parts, by weight, of aniline are diazotized in the usual manner with 267.7 parts, by weight, of hydrochloric acid of thirty per cent, and sixty-nine parts, by weight, of sodium nitrite and at atemperature between 0 and 5 centigrade, and while stirring well introduced into a paste prepared j and forty parts, by weight, of acetate of soda.
- naphthaline disulphonic acid differs es'sen- V tially fromthc known isomeric dioxynaphtha from four hundred and four parts, by weight, of the dlSOdllHl'l salt of the new dioxynaphthaline disulphonic acid and three hundred
- the coloring.-,matter a large part of which separates of itself, is precipitated by means of common salt, pressed off, and dried.
- Example II.Two hundred and forty-five parts, by weight, of na'phthionate of soda are diazotized in the usual manner with 267.7 parts,by weight, of hydrochloric acid of thirty per cent, and sixty-nine parts, by weight, of sodium nitrite and at a low temperatnrmand while stirring well mixed with a solution of four hundred and fuserparts, by weight, of the .di's'odium salt of thenew dioxynaphthaline disulphonic acid and-one hundred and thirtyfive parts, by weight, 'of sodafiir eighty parts, by weight, of caustic soda in about three thousand parts, Dy-Weight, of water. After someihon rs standing'the coloringmatter separates in gelatinous form. It is precipitated by pecans ef-common salt, filtered 015?, and dried.
- diazoabodies-mentioned in the examples can be substituted the diazo bodies derived from the following bases and amidesulphonic acids: as meta-'xylidine, 'x'yli-cumidme, alpha naphthylamine, beta naphthylam1ne, amidoazo-benz01e,amidoazo-toluol,sul-' phan lic acid, metanilic acid, ,toluidine sul- 8o phonic acid, amidonaphthol sulphonic' acid (13,) amidonaphthol sulphonic acid (G,) as mono-xylidine sulphonic acid, beta-naphth yl amine sulphonic acid, (Brenner) alpha-naphthylamine disulphonic acid, (Dahl,) betanaphthylaminedisulphonic acid, G, betanaphthylamine disulphonic acid, 5R3 beta
- the coloring-matter thns'produced is in we
- Thenew coloring-matter is the first having the property of dyeing wool of greatly dilfer- .ing shades, which will resist the influence of light and of alkali, so as to permitof their employment for industi'ial'purpose's. 'On be-.
- the shade obtained is a blue-red. If to the dye-bath are added mordants, such as alum, together with the acid, or after the coloris fixed on'the fiber by means of the acid, the shade will be a darkclaret with vivid reflection. The same will be the case when are added copper chloride or sulphate, On the addition of chrome-alum is obtained a dark violet. On the addition of alkali cliroinates a deep black is produced.
- the formula of the coloring-matter is expressed by I OII - on X --N O H 803m some.
- Theazo coloring-matter derived from the herein -described dioxynaphthaline disulphonic acidand diazo bodies which is a brown powder easily soluble in cold water and diluted acids, freely soluble in hot alcohol of 75Tralles, insoluble in ether and ligroine, and adapted for dyeing wool in greatly diifering shades ranging from bluish-red to deep black, dependingnpon the use of acids or the latter in combination with metallic mordants, as set forth.
Description
This-novel body" is'deri'vec'l from'a new n'aph UNITED STATES PATENT OFFICE.
HANS KUZEL, on noo1.is'r-oN-TnE-MMN,GER AnY, Asslenon TO THE 1mm;- WERKE, VORMALS MEISTER, LUCIUS a BRUNING, OF, SAME PLACE.
AZO
SPECIFICATION forming part of Reissued' Letters Patent No. 11,231, dated April 5, 1892.- Original No. 468,283, dated August 25, 1891. Application for ilments I'ehmsry 2a, 1892. Serial No. 422,940.
I ,Tdallwhont it may concern.-
Be it known that I, HANS KUZEL, doctor of philosophy, a citizen ofthe Empire of Germany, residing at Hiichst-on-the-Main, in the 5 Empire of Germany, have invented certain 113W and useful Improvements in Coloring- Matter; and I do hereby declare the following to boa full, clear, and exact description of the invention, such as ,will enable others skilled in the art to which it appertains to make and use the same.v t F In my application for Letters Patent Serial No. 360,968 I have described my process for the production of a new dioxynaphthaline disulphonic acid and this novel body itself.
thol trisnlphonic acid or its anhydride, which is described in the GermanLetter-sPatentNo. 16,955," recently published. This new dioxyline disulphon-ic acid of the German Letters Patent No. 40,893, 'whichiswlerived from another naphthol trisulphonic acidaiid fia' other properties, viz: A solution of it turns to reddish-violet on the addition on solution of chloride'of lime, and on combination with 'diazo bodies no other than brown azo coloring-matters are formed.
My inventior trelates to the manufacture of azo coloringmiatter ranging in color from bluishsred to "violet, derived from the hereindescribed diazonaphthaline disulphonic acid, characterized, as above mentioned, by com- 5 bining said acid or its salts with diazo bodies and adapted for dyeing wool in greatly differing shades of color, depending upon the use of acids, such'as sulphuric acid or bisulphates or acids in combination with metallic mordants, such as alum, chrome alum, or alkaline chromates.
In practically carrying out my invention 1' proceed as follows:
Example L-Ninetytn ree parts, by weight, of aniline are diazotized in the usual manner with 267.7 parts, by weight, of hydrochloric acid of thirty per cent, and sixty-nine parts, by weight, of sodium nitrite and at atemperature between 0 and 5 centigrade, and while stirring well introduced into a paste prepared j and forty parts, by weight, of acetate of soda.
naphthaline disulphonic acid differs es'sen- V tially fromthc known isomeric dioxynaphtha from four hundred and four parts, by weight, of the dlSOdllHl'l salt of the new dioxynaphthaline disulphonic acid and three hundred The coloring.-,matter, a large part of which separates of itself, is precipitated by means of common salt, pressed off, and dried.
Example II.Two hundred and forty-five parts, by weight, of na'phthionate of soda are diazotized in the usual manner with 267.7 parts,by weight, of hydrochloric acid of thirty per cent, and sixty-nine parts, by weight, of sodium nitrite and at a low temperatnrmand while stirring well mixed with a solution of four hundred and feurparts, by weight, of the .di's'odium salt of thenew dioxynaphthaline disulphonic acid and-one hundred and thirtyfive parts, by weight, 'of sodafiir eighty parts, by weight, of caustic soda in about three thousand parts, Dy-Weight, of water. After someihon rs standing'the coloringmatter separates in gelatinous form. It is precipitated by pecans ef-common salt, filtered 015?, and dried.
For the diazoabodies-mentioned in the examples can be substituted the diazo bodies derived from the following bases and amidesulphonic acids: as meta-'xylidine, 'x'yli-cumidme, alpha naphthylamine, beta naphthylam1ne, amidoazo-benz01e,amidoazo-toluol,sul-' phan lic acid, metanilic acid, ,toluidine sul- 8o phonic acid, amidonaphthol sulphonic' acid (13,) amidonaphthol sulphonic acid (G,) as mono-xylidine sulphonic acid, beta-naphth yl amine sulphonic acid, (Brenner) alpha-naphthylamine disulphonic acid, (Dahl,) betanaphthylaminedisulphonic acid, G, betanaphthylamine disulphonic acid, 5R3 betanaphthylamine trisulphonic acid, naphthalidine sulphonic acid, amidoazo-benzole sulphonic acid, meta- 'nitraniline, para nitraml ne,meta-amidobenzoic acid, ortho-amidosalicylic acid, para-amidosalicylic acid, amide-- para oxybenz o1c acid, ortho phcnetidine, i para-phenetldme, ortho-anisidine, para-aimisi amidonaphtholmethylether, benzidine, toulid ne, diethoxybenzidine, dimethoxybenzidine, meta-diamidodiphenic acid, or another amine or its sulphonic or carbonic acid.
dine, ortho amide para cresolmethylether, '5
The coloring-matter thns'produced is in we Thenew coloring-matter is the first having the property of dyeing wool of greatly dilfer- .ing shades, which will resist the influence of light and of alkali, so as to permitof their employment for industi'ial'purpose's. 'On be-.
ing dyed with sulphuric acid the shade obtained is a blue-red. If to the dye-bath are added mordants, such as alum, together with the acid, or after the coloris fixed on'the fiber by means of the acid, the shade will be a darkclaret with vivid reflection. The same will be the case when are added copper chloride or sulphate, On the addition of chrome-alum is obtained a dark violet. On the addition of alkali cliroinates a deep black is produced. By thisv characteristic property the new azo coloring-matter difiers'frorn all the azo coloring-matters known before, with which could not be produced more than one suitable shade,
and whicli, 1ike the coloring-matter of the German Letters Patent No.40,893, do not produce a black on the addition of chromate of .potash, as the chromate destroys the coloring matter.
The formula of the coloring-matter is expressed by I OII - on X --N O H 803m some.
Having thus described my invention and in what manner it can be performed, what I claimas' new, and desire tosecure byLetters Patent, is-
Theazo coloring-matter derived from the herein -described dioxynaphthaline disulphonic acidand diazo bodies, which is a brown powder easily soluble in cold water and diluted acids, freely soluble in hot alcohol of 75Tralles, insoluble in ether and ligroine, and adapted for dyeing wool in greatly diifering shades ranging from bluish-red to deep black, dependingnpon the use of acids or the latter in combination with metallic mordants, as set forth. Y
In testimony whereof I afiix my signatu re in presence of two witnesses.
HANS KUIZEL. WVitnesses:
JOSEF REVERDY,
HEINRICH HAHN.
Family
ID=
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