US2018103A - Hydrazine sulphonate - Google Patents
Hydrazine sulphonate Download PDFInfo
- Publication number
- US2018103A US2018103A US649446A US64944632A US2018103A US 2018103 A US2018103 A US 2018103A US 649446 A US649446 A US 649446A US 64944632 A US64944632 A US 64944632A US 2018103 A US2018103 A US 2018103A
- Authority
- US
- United States
- Prior art keywords
- amino
- hydrazine
- parts
- acid
- benzoylamino
- 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
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- ZMJZYXKPJWGDGR-UHFFFAOYSA-N aminosulfamic acid Chemical compound NNS(O)(=O)=O ZMJZYXKPJWGDGR-UHFFFAOYSA-N 0.000 title description 6
- -1 aroylamino hydroxynaphthalenes Chemical class 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- TYEUVMQIBMZFLS-UHFFFAOYSA-N n-(3-hydroxynaphthalen-2-yl)benzamide Chemical compound OC1=CC2=CC=CC=C2C=C1NC(=O)C1=CC=CC=C1 TYEUVMQIBMZFLS-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- PXLIDIMHPNPGMH-UHFFFAOYSA-N sodium chromate Chemical compound [Na+].[Na+].[O-][Cr]([O-])(=O)=O PXLIDIMHPNPGMH-UHFFFAOYSA-N 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
- BERPCVULMUPOER-UHFFFAOYSA-N Quinolinediol Chemical class C1=CC=C2NC(=O)C(O)=CC2=C1 BERPCVULMUPOER-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant 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
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/48—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom
- C07C311/49—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom to nitrogen atoms
Definitions
- the present invention relates to new hydrazine-sulphonates, more particularly it relates to compounds corresponding to the following probable general formula:
- Y stands for alkyl, alkoxy or halogen.
- compositions of matter, thus produced are then brought onto the fibers in the presence of an alkali and the goods, thus treated, are thereafter subjectedtoa steaming operation.
- 2-hydroxynaphthalene As combining components of the aforesaid kind may be named: 2-hydroxynaphthalene, its-nuclear substitution products as, for instance, aroylamino hydroxynaphthalenes, (2 hydroxynaphthalene-3-carbonyl) -amino-aryls (as described in U. S. Patents,N,0. 1,101,111 and No. 1,140,747), (6 halogenor 6-arylamino-2-hydroxy-naphthalene-3-carbonyl)-amino-aryls (see German Patent No. 396,519 and British Patent No. 330,349), derivatives of l-hydro-xy-naphthalene-4-carboxylic acid (see U. S.
- Patent No. 1,453,660 as, for instance, l-hydroxy-naphthalene 4 phenyl-ketone;-compounds. containing an acidic methylene group capable of being combined with diazocompounds, as,'for instance, pyrazolones and derivatives of fl-ketonaldehyde, for instance, acetoacetyl-amino-aryls and di- (aceto-acetyl-amino) aryls (see U. S. Patents No..'1 .594,864, No. 1,594,866, No. 1,594,867, No. 1,580,709, No. 1,634,090), dihydroxy-quinolines (see U. S. Patents No.
- the dyeing preparations yield under these conditions, by steaming only, insoluble azo-dyestuffs on the Such application to the fiber may consist in dyeing according to the one-bath method, or in printing; the dye-bath or the printing paste, or even the dyeing preparations themselves in powder form, are advantageously mixed with the usual dyeing or printing assistants having wetting, emulsifying or solvent properties, or also with the additional agents customarily used in nitrosamine-printing colors, such. as, for example, chromate.
- a printing paste which contains:
- a bluish-green print is obtained.
- a violet print is obtained.
- Z means an acyl radical of the lower aliphatic series or of the aromatic isocyclic series and Y stands for alkyl, alkoxy or halogen, which compounds represent when dry yellowish to brownish powders and are valuable intermediates for the production of azo dyestuffs.
- R represents a radical of the aromatic isocyclic series and Y stands for alkyl, alkoxy or halogen, which compounds represent when dry 3.
- Y stands for alkyl, alkoxy or halogen, which compounds represent when dry 3.
- alkyl wherein the benzene nucleus I may be substituted by alkyl, alkoxy or halogen and Y means alkyl, alkoxy or halogen, which compounds represent when dry yellowish to brownish powders and are valuable intermediates for the production of azo dyestuffs.
Description
Patented Oct. 22, 1935 UNITED STATES PATENT OFFICE bach-on-the-Main,
Germany, assignors to General Aniline Works, Inc., New-York, N. Y., a corporation of Delaware No Drawing. Application December 29, 1932,
Serial No. 649,446. 1932 In Germany January 12,
4 Claims. (01. 260-124) The present invention relates to new hydrazine-sulphonates, more particularly it relates to compounds corresponding to the following probable general formula:
wherein Y stands for alkyl, alkoxy or halogen.
These compounds are produced by acting with a reducing agent on the corresponding 2.5-disubstituted 4-acylamino-benzene-l-diazo-sulphonic acids.
They are of a great value for the production of azo-dyestuffs. For this purpose, they are advantageously first mixed. with combining components containing a hydroxyor an o-alkali metal group, whereof the adjacent position is capable of attaching an aryl azo group, provided that neither of the dyestuil' components contains a group producing solubility in water. The compositions of matter, thus produced, are then brought onto the fibers in the presence of an alkali and the goods, thus treated, are thereafter subjectedtoa steaming operation.
As combining components of the aforesaid kind may be named: 2-hydroxynaphthalene, its-nuclear substitution products as, for instance, aroylamino hydroxynaphthalenes, (2 hydroxynaphthalene-3-carbonyl) -amino-aryls (as described in U. S. Patents,N,0. 1,101,111 and No. 1,140,747), (6 halogenor 6-arylamino-2-hydroxy-naphthalene-3-carbonyl)-amino-aryls (see German Patent No. 396,519 and British Patent No. 330,349), derivatives of l-hydro-xy-naphthalene-4-carboxylic acid (see U. S. Patent No. 1,453,660), as, for instance, l-hydroxy-naphthalene 4 phenyl-ketone;-compounds. containing an acidic methylene group capable of being combined with diazocompounds, as,'for instance, pyrazolones and derivatives of fl-ketonaldehyde, for instance, acetoacetyl-amino-aryls and di- (aceto-acetyl-amino) aryls (see U. S. Patents No..'1 .594,864, No. 1,594,866, No. 1,594,867, No. 1,580,709, No. 1,634,090), dihydroxy-quinolines (see U. S. Patents No. 1,820,039, No. 1,846,073 andNo. 1,846,074, British Patent No. 332,940), (2-hydroxy-carbazole-3-carbonyl) -amino-aryls,"(2 hydroxy benzo carbazole-3-carbonyl) -amino-aryls, (2 hydroxy anthracene-3-carbonyl) -amino-aryls.
The hydrazinesulpho'nate and the coupling .component, or an alkali metal salt of the latter,
may be ground together and this mixture may be applied in an alkaline medium to the fiber. The dyeing preparations yield under these conditions, by steaming only, insoluble azo-dyestuffs on the Such application to the fiber may consist in dyeing according to the one-bath method, or in printing; the dye-bath or the printing paste, or even the dyeing preparations themselves in powder form, are advantageously mixed with the usual dyeing or printing assistants having wetting, emulsifying or solvent properties, or also with the additional agents customarily used in nitrosamine-printing colors, such. as, for example, chromate.
The following examples serve to illustratethe invention, but they are not intended to limit it thereto, the parts being by weight:
(1) 225 parts of the sodium salt of 4-benzoylamino 2.5 dimethoxybenzene-l-diazo sulphonic acid of 87.05% strength are suspended in 3000 parts .of acetic acid of 3% strength, the whole is heated to i C. to C. and at this temperature 150 parts of zincdust are slowly introduced. When the mass has-become dissolved and decolorized, it is rendered alkaline by means of sodium carbonate, filtered by suction while hot, sodium chloride is added and the product worked up as usual. There are thus obtained 385 parts of a feebly yellow press cake of the sodium salt of 4-benzoylamino-2.5dimethoxybenzene-l-hydrazine-sulphonic acid containing,58.35% of the pure substance.
It corresponds to the following formula:
(2) 394 parts of thesodium salt of 4-benzoylamino-Z-chloro-S methoxybenzene-l-diazosulphonic acid are suspended in a solution of parts of calcined sodium carbonate in 4000 parts of water, parts of sodium-hydrosulphite are added thereto and the whole .is heated in the course of hour to 60 C. to 65 C. This temperature is maintained until the mass has become decolorized, indicating complete reduction. Thereupon, the Whole is heated-to 8 5 C. to 90 C., filtered by suction, sodium chloride is added to the filtrate and the product is worked'up' as usual. There are obtained 1222 parts of a nearly colorless paste of the sodium salt of 4-benzoylg amjno-2-chloro-S-methoxybenzene 1 hydrazine sulphonic acid containing 19.36% of the pure substance. 7
It corresponds to the following formula:
Q-OO-NHQNlEb-NH-SOr-Na V V V o1 V 4r--( phenoxy-acetyl-amino Q 2,5 -dimethoxybenzene-l-diazosulphonic acid,
.dimethoxybenzene-l-diazosulphonic acid, 4-benzoylamino-2,5-dimethylbenzene-l-diazosulphonic acid, 4-benzoylamino2-methyl-5-ch1orobenzene- 1 -diazosulphonic acid, a
4-(01- or p-naphthoylamino) -2-methoxy@-5-methylbenzene-l-diazosulphonicacid, 4-benzoylamino-2-cho1oro 5 methylbenzene-ldiazosulphonic acid,
I 2.5-dimethoxy-benzene-l-diazosulphonic acid, 4- (2'-chlorobenzoylamino) -2,5-diethoxybenzene- .1 :diazosulohom'c acid,
. miibl'otolmmmo-i-i-li-idzlcisuiplrxlmci a cadirl,
4 nb-ireimasmlnlpironalmnir-r ll-.5 ,-5(l: dihtnorbelnmnzer-1 1 l ll-aiiasmlnlpmin Lei mil 5 imdi i.
1 1 1 3 )E iildzleanelal: 5: wins :1 )',J :tsiislei El :1 n waddle r02 1: nl 1H o fltitjti ftllll l'iihi etenmwiofcii itiimimtssnio examiner-emu 4-.(4K-methylbenzene- 1"-sulphonylamino) 2,5
4- 3'-methoxy-naphthalene-2Gcarbonylamino) Caustic soda solution of 34 B 30 7 Water -1 273 Starch tragacanth-thickening 500 Sodium chromate solution (1:4) 20 is printed on the material; the material is then 5 dried, steamed for 10 minutes in a Mather-Flatt apparatus; rinsed hot, soaped and rinsed again.
, A violet print is thus obtained.
(5) 60 parts of the sodium salt of 4-benzoy1- 10 amino 2.5 dimethoxybenz'ene-l-hydrazine-sulphonic acid of 58.35% strength, obtainable as de-. scribed in Example 1,10 parts of anhydrous sodium acetate and 30 parts of Z-hydroxyanthracene 3 carbonyl-( l-amino-Z-methylbenzene are ground to form a homogeneous powder. 7 There are obtained 100 parts of dyestuff preparation.
A printing paste which contains:
. Parts 2 The above dyestuff preparation 1 u .50 Thiodiglycol Caustic soda solution of 34 B. 1 35' Water 375 Neutral starch tragaeanth-thickening 500 Sodium chromate solution (1:4) 20 is printed on the material and the goods are treated as indicated in Example 4.
A bluish-green print is obtained. By using, instead of 2'-hydroxy-anthracene- 3 -carbonyll-amino-Z-methylbenzen'e) 3-benzoylamino-2-hydroxynaphthalene, a violet print. is obtained.
(6) A printing paste which contains:
A slimming:sittetaccmmininmg: i i
new? i: :is; nirrmtla i m d I 1th a ante-teal m 72(11 1: hall a; (moist "are v'ov'ccelcofli 1 19:: not elzesclniitk dl:: mfiazmpl o le. l. V
l 1. r ar'ielldlis-wiviele t [lilffil its .tt'ilst s tofatuiniu l l l 1r 'g'iism g1 toklr 2h ytqmimn'n .eulnlnnozo la :adi 's admit: i and: in i here 13 250,?! o: ntonqrmntst it no 1 1 rpnossss: mm We: a amounted: i 11' m a 1mm Mariel-snow 1 i2 )1 d haltet ,1 e-le; mirth $411K itltnoiregroliningxeimpimlas. 7 Mi" The following table indicates the shades of a series of other dyeings or prints obtained in an yellowish to brownish powders and are valuable intermediates for the production of azo dyestuffs.
Sodium salt of 4-benzoyl-amino-2,5-diethoxybenzene-1- hygrazine sulphonic acid.
Do Sodium salt of 4-acetyl-amino-2,5-diu1ethoxy-benzene-l-l1ydrazine sulphonic acid.
Do Do Sodium salt of 4-(pl1enoxy-acetylamino)- begzene-l-hydrazine sulphonic acid.
hylbenzene-l-sulphonyl:amino)-2,5-
Z-hydroxynanhthalnna 3-methy1-1-phenyl-5-pyrazolone 1-l1ydroxynaphthalene-4-phenylketone V 2-hydroxy-carbazole-3-carbonyl-(1-amin0-4-chlorobenzene) 3-benzoylamino-2-hydroxynaphthalene 4,4-di-(acetoacetyl-amino)-3,3-dimethyl-diphenyl Brownish violet.
Brownish-orange.
iolet.
Do. Yellowish-orange.
2,3,-hydroxynaphthoyl-(1-amino-2-methoxy-benzene) Redjgish-blue. 0.
4,4-di)-(acetoacetyl-amino)-3,3-dimethyl-diphenyl g fgfiggish-orange. Q55 1]giifiififififitiififli 51558 i-iiltliiy nhtfiih Reddish-blue.
zene 2,3-hydroxynaphthoyl-(l-amino-Z-ethoxybenzene) Blue. 4,4-di-(acetoacetyl-amino)-3,3-dimethyl-diphenyl Orange. 2,3-hydroxynaphthoyl-aminobenzene Reddish-vlolet.
dinlethoxy-benzene-l-hydrazine sulphonic acld.
analogous manner:
We claim:
1. The hydrazine sulphonates corresponding to the general formula:
wherein Z means an acyl radical of the lower aliphatic series or of the aromatic isocyclic series and Y stands for alkyl, alkoxy or halogen, which compounds represent when dry yellowish to brownish powders and are valuable intermediates for the production of azo dyestuffs.
2. The hydrazine sulphonates corresponding to the general formula:
wherein R represents a radical of the aromatic isocyclic series and Y stands for alkyl, alkoxy or halogen, which compounds represent when dry 3. The hydrazine sulphonates corresponding to the general formula:
alkyl wherein the benzene nucleus I may be substituted by alkyl, alkoxy or halogen and Y means alkyl, alkoxy or halogen, which compounds represent when dry yellowish to brownish powders and are valuable intermediates for the production of azo dyestuffs.
4. The 4-benzoylamino 2,5 dimethoxy benzene-1-hydrazine-su1phonate of the formula:
which compound represents a feebly yellow powder and is a valuable intermediate for the production of azo dyestufis.
ARTHUR ZITSCHER. WILHELM SEIDENFADEN.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2018103X | 1932-01-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2018103A true US2018103A (en) | 1935-10-22 |
Family
ID=7966121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US649446A Expired - Lifetime US2018103A (en) | 1932-01-12 | 1932-12-29 | Hydrazine sulphonate |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2018103A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3352876A (en) * | 1960-01-05 | 1967-11-14 | Ciba Geigy Corp | 2-indanyl-hydrazines and salts thereof |
| US5400710A (en) * | 1993-06-23 | 1995-03-28 | Man Roland Druckmaschinen Ag | Apparatus for exchanging a doctor blade in a rotary printing press |
-
1932
- 1932-12-29 US US649446A patent/US2018103A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3352876A (en) * | 1960-01-05 | 1967-11-14 | Ciba Geigy Corp | 2-indanyl-hydrazines and salts thereof |
| US5400710A (en) * | 1993-06-23 | 1995-03-28 | Man Roland Druckmaschinen Ag | Apparatus for exchanging a doctor blade in a rotary printing press |
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