DE221696C - - Google Patents
Info
- Publication number
- DE221696C DE221696C DE1907221696D DE221696DA DE221696C DE 221696 C DE221696 C DE 221696C DE 1907221696 D DE1907221696 D DE 1907221696D DE 221696D A DE221696D A DE 221696DA DE 221696 C DE221696 C DE 221696C
- Authority
- DE
- Germany
- Prior art keywords
- pyrazolone
- naphthyl
- methyl
- acid
- disulfonic acid
- 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
- 239000000975 dye Substances 0.000 claims description 24
- 239000000987 azo dye Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000003460 sulfonic acids Chemical class 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 description 16
- NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 description 12
- 210000002268 Wool Anatomy 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 5
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 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
- NNZXDXMEXBYSRF-UHFFFAOYSA-N 2-methyl-4H-pyrazol-3-one Chemical compound CN1N=CCC1=O NNZXDXMEXBYSRF-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 3
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 3
- 229960004889 salicylic acid Drugs 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
- DOPJTDJKZNWLRB-UHFFFAOYSA-N 2-Amino-5-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C=C1O DOPJTDJKZNWLRB-UHFFFAOYSA-N 0.000 description 2
- HUWXDEQWWKGHRV-UHFFFAOYSA-N 3,3'-Dichlorobenzidine Chemical compound C1=C(Cl)C(N)=CC=C1C1=CC=C(N)C(Cl)=C1 HUWXDEQWWKGHRV-UHFFFAOYSA-N 0.000 description 2
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- CDOUPQQJGFCACL-UHFFFAOYSA-N N-(2-amino-5-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC(C)=CC=C1N CDOUPQQJGFCACL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- ZARYBZGMUVAJMK-UHFFFAOYSA-N 2-amino-4-chloro-5-nitrophenol Chemical compound NC1=CC(Cl)=C([N+]([O-])=O)C=C1O ZARYBZGMUVAJMK-UHFFFAOYSA-N 0.000 description 1
- NZFRIOGEBLHAST-UHFFFAOYSA-N 2-ethyl-4H-pyrazol-3-one Chemical compound CCN1N=CCC1=O NZFRIOGEBLHAST-UHFFFAOYSA-N 0.000 description 1
- DTNODBHGOLWROS-UHFFFAOYSA-N 3-amino-4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1N DTNODBHGOLWROS-UHFFFAOYSA-N 0.000 description 1
- -1 3-methyl-5-pyrazolone - p-phenylenediamine Chemical compound 0.000 description 1
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-Nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- WQTCZINVPXJNEL-UHFFFAOYSA-N 4-amino-3-methylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=CC=C1N WQTCZINVPXJNEL-UHFFFAOYSA-N 0.000 description 1
- KRBZPDUCRARLKM-UHFFFAOYSA-N 5-amino-1,6-dimethylcyclohexa-2,4-diene-1-sulfonic acid Chemical compound CC1C(N)=CC=CC1(C)S(O)(=O)=O KRBZPDUCRARLKM-UHFFFAOYSA-N 0.000 description 1
- 241000947840 Alteromonadales Species 0.000 description 1
- 229910020320 CLi Inorganic materials 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N Ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 229940018564 M-PHENYLENEDIAMINE Drugs 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
- ZUJURJDZOPMJPH-UHFFFAOYSA-M [Cl-].[N-]=[N+]=C1CC=CC=C1 Chemical compound [Cl-].[N-]=[N+]=C1CC=CC=C1 ZUJURJDZOPMJPH-UHFFFAOYSA-M 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 235000020127 ayran Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001808 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000001771 impaired Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
- C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
- C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
- C09B35/10—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type
- C09B35/18—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type from heterocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
OTten-PATENTAMT. OTten PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- Ju 221696 KLASSE 22 a. GRUPPE- Ju 221696 CLASS 22 a. GROUP
Es wurde gefunden, daß die durch Kondensation von Naphtylhydrazinsulfosäuren mit Acetessigester erhältlichen Naphtylpyrazolonsulfosäuren sehr wertvolle Komponenten für die Darstellung von Azofarbstoffen sind, und zwar wird durch die Einführung des Naphtylrestes in das Farbstoffmolekül gegenüber dem Phenylrest die Farbkraft der betreffenden Azofarbstoffe verstärkt, ohne daß die sonstigenIt has been found that the by condensation of naphtylhydrazine sulfonic acids with Acetoacetic ester available naphthylpyrazolone sulfonic acids are very valuable components for the preparation of azo dyes, and that is due to the introduction of the naphthyl radical in the dye molecule compared to the phenyl radical, the color strength of the azo dyes in question reinforced without the others
ίο guten Eigenschaften derartiger Pyrazolonfarbstoffe, wie Lichtechtheit oder Egalisierungsvermögen, beeinträchtigt werden. So ist z. B. der Anilinfarbstoff aus dem von der 2 · 4 · 8-Naphtylamindisulfosäure derivierenden Pyrazolonderivat ein Gelb von hervorragender Farbkraft und Lichtechtheit, der Farbstoff aus Dichlorbenzidin und 2 Molekülen des Pyrazolonderivates aus 2 · 6 · 8-Naphtylamindisulfosäure ein sehr wertvolles, lichtechtes Baumwoll-ίο good properties of such pyrazolone dyes, such as lightfastness or leveling ability, are impaired. So is z. B. the aniline dye from that of 2 x 4 x 8-naphthylamine disulfonic acid derived pyrazolone derivative a yellow with excellent color strength and lightfastness, the dye Dichlorobenzidine and 2 molecules of the pyrazolone derivative from 2 · 6 · 8-naphthylamine disulphonic acid a very valuable, lightfast cotton
orange.orange.
In eine mit überschüssiger Soda versetzte Lösung von 38,2 kg 1 - β - Naphtyl-4 · 8 - disulfosäure : 3 - methyl - 5 - pyrazolon läßt man unter Rühren eine Diazobenzolchloridlösung einfließen, die in üblicher Weise aus 9,3 kg Anilin hergestellt ist. Nach einer halben Stunde ist die Farbstoffbildung beendet. Es wird zur Erzielung einer gut preßbaren Form des Farbstoffs auf 700 erwärmt, ausgesalzen, gepreßt und getrocknet. Der Farbstoff zieht sauer sehr gut auf Wolle in klarer, gelber Nuance, ist lichtecht und egalisiert gut.A solution of 38.2 kg of 1 - β - naphthyl-4 · 8 - disulfonic acid: 3 - methyl - 5 - pyrazolone, mixed with excess soda, is poured into a diazobenzene chloride solution, which is prepared in the usual way from 9.3 kg of aniline, with stirring is. The formation of the dye has ended after half an hour. It is heated to 70 0 of the dye to obtain a good crimp shape, salted, pressed and dried. The dyestuff absorbs very well on wool in a clear, yellow shade, is lightfast and levels out well.
18,4 kg Benzidin (bzw. 21,2 kg Tolidin), werden in der üblichen Weise tetrazotiert und mit einer sodaalkalischen Lösung von 76,4 kg i-ß-Naphtyl-4 · S-disulfosäure-s-methyl-S-pyrazolon gekuppelt. Beide Farbstoffe scheiden sich lebhaft rot gefärbt und kristallinisch aus, werden gepreßt und getrocknet. Sie färben ungebeizte Baumwolle in rotstichig orangefarbenen bzw. roten Nuancen von großer Säureechtheit.18.4 kg benzidine (or 21.2 kg tolidine), are tetrazotized in the usual way and with a soda-alkaline solution of 76.4 kg i-ß-Naphthyl-4 · S-disulfonic acid-s-methyl-S-pyrazolone coupled. Both dyes are lively red colored and crystalline, are pressed and dried. They dye unstained cotton a reddish orange color or red nuances of great acid fastness.
12,2 kg Dianisidin werden in üblicher Weise tetrazotiert und in eine mit Soda alkalisch gehaltene Lösung von 38,2 kg i-ß-Naphtyl-4 · 8-disulfosäure-3-methyl-5-pyrazolon unter Rühren einlaufen gelassen. Die tief blaurote Lösung wird nach 5 Stunden ausgesalzen und der Farbstoff gepreßt und getrocknet. Er zieht gut auf ungebeizte Baumwolle und färbt dieselbe blaurot.12.2 kg of dianisidine are tetrazotized in the usual way and kept alkaline with soda Solution of 38.2 kg of i-ß-naphthyl-4 · 8-disulfonic acid-3-methyl-5-pyrazolone with stirring let in. The deep blue-red solution is salted out after 5 hours and the Dye pressed and dried. It pulls well on unstained cotton and dyes the same blue red.
25<3 kg Dichlorbenzidin werden in der üblichen Weise mit Salzsäure und Nitrit tetrazotiert und die Lösung der Tetrazoverbindung wird unter Rühren in eine überschüssige Soda enthaltende Lösung von 76,4 kg i-ß-Naphtyl-6 · 8 - disulfosäure - 3 - methyl - 5 - pyrazolon einlaufen gelassen. Nach 2 Stunden ist die Farbstoffbildung beendet. Man wärmt an, salzt aus, preßt und trocknet. Der Farbstoff färbt 2 5 <3 kg of dichlorobenzidine are tetrazotized in the usual way with hydrochloric acid and nitrite and the solution of the tetrazo compound is poured into a solution of 76.4 kg of i-ß-naphthyl-6 · 8-disulfonic acid-3-methyl with stirring - 5 - pyrazolone run in. The formation of the dye has ended after 2 hours. You warm up, salt out, press and dry. The dye stains
ungeheizte Baumwolle in sehr klarer, rotstichig orangefarbener Nuance an und ist sehr lichtecht.unheated cotton in a very clear, reddish orange shade and is very lightfast.
18,4 kg Benzidin werden in der üblichen Weise tetrazotiert und halbseitig mit 13,8 kg Salicylsäure schwach sodaalkalisch gekuppelt. Das Produkt hat sich nach 12 Stunden vollkommen und kristallinisch ausgeschieden. Man fügt nun noch eine alkalische Lösung von 38,2 kg i-ß-Naphtyl-4 · 8-disulfosäure-3-methyl-5-pyrazolon hinzu und setzt das Rühren des Gemisches noch weitere 12 Stunden fort. Der nunmehr fertig gebildete Farbstoff wird angewärmt, ausgesalzen, gepreßt und getrocknet. Er färbt ungeheizte Baumwolle in sehr klarer, gelbstichig orangefarbener Nuance von erheblicher Lichtechtheit an.18.4 kg of benzidine are tetrazotized in the usual way and on one side with 13.8 kg Salicylic acid coupled weakly with alkaline soda. The product has been completely used after 12 hours and precipitated in crystalline form. An alkaline solution of 38.2 kg of i-β-naphthyl-4 · 8-disulfonic acid-3-methyl-5-pyrazolone is now added and continue stirring the mixture for a further 12 hours. Of the The dye, which is now completely formed, is heated, salted out, pressed and dried. He dyes unheated cotton in a very clear, yellowish orange shade of considerable Lightfastness on.
16,4 kg 2-Acetamino-4-toluidin werden in16.4 kg of 2-acetamino-4-toluidine are in
35 kg Salzsäure und 250 1 Wasser gelöst und bei o° mit 6,9 kg Nitrit diazotiert. Die resultierende Lösung wird unter Rühren in eineDissolved 35 kg of hydrochloric acid and 250 l of water and diazotized at 0 ° with 6.9 kg of nitrite. The resulting Solution is poured into a
sodaalkalische Lösung von i-Naphtol-4-sulfosäure einlaufen gelassen. Die Farbstoffbildung ist sofort beendet, und das Gemisch wird nun zwecks Verseifung der Acetylgruppe auf 950 erwärmt, mit so viel Natronlauge versetzt, daß es 5 Prozent Natron enthält, und eine halbe Stunde auf 950 gehalten. Nun wird das Natron partiell mit Schwefelsäure neutralisiert und der Farbstoff gepreßt. Das noch alkalische Preßgut wird wieder angeteigt, mit 7 kg Nitrit versetzt und unter Rühren bei 50 in überschüssige Salzsäure eingetragen. Nach 6 Stunden ist die Diazotierung beendet. Man preßt ab, teigt die Diazoverbindung mit kaltem Wasser an und trägt sie in eine sodaalkalisch gehaltene Lösung von 38,2 kg i-ß-Naphtyl-4 · 8-disulfosäure-3-methyl-5-pyrazolon (bzw. ι - β - Naphtyl-6 · 8-disulfosäure-3-methyl-5 - pyrazolon) ein. Nach 4 Stunden ist die Kuppelung beendet. Man wärmt an, salzt aus, preßt und trocknet. Beide Farbstoffe färben Wolle lebhaft in roten walkechten Tönen an.soda-alkaline solution of i-naphthol-4-sulfonic acid allowed to run in. The dye formation is immediately terminated, and the mixture is then heated to 95 0 for the purpose of hydrolysis of the acetyl group, treated with caustic soda so much that it contains 5 percent soda, and held for half an hour to 95 0th Now the soda is partially neutralized with sulfuric acid and the dye is pressed. The still alkaline material to be pressed is made into a paste again, admixed with 7 kg of nitrite and added to excess hydrochloric acid under stirring at 5 0th The diazotization is complete after 6 hours. One squeezes off, pastes the diazo compound with cold water and carries it into a soda-alkaline solution of 38.2 kg of i-ß-naphthyl-4 · 8-disulfonic acid-3-methyl-5-pyrazolone (or ι - β - Naphthyl-6 · 8-disulfonic acid-3-methyl-5-pyrazolone). The coupling is finished after 4 hours. You warm up, salt out, press and dry. Both dyes dye wool vividly in red milled shades.
In der folgenden Tabelle sind die Nuancen einer Anzahl der neuen Farbstoffe aufgeführt:The following table lists the nuances of a number of the new dyes:
2 - Acetamino - 4 - toluidin 4- a-Naphtol-4-sulfo-5
2 - acetamino - 4 - toluidine 4- a-naphtol-4-sulfo-
Wolleon unheated
Wool
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT45760D AT45760B (en) | 1907-06-28 | 1909-03-03 | Process for the preparation of azo dyes. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE221696C true DE221696C (en) |
Family
ID=482651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1907221696D Expired - Lifetime DE221696C (en) | 1907-06-28 | 1907-06-28 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE221696C (en) |
-
1907
- 1907-06-28 DE DE1907221696D patent/DE221696C/de not_active Expired - Lifetime
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