US1941057A - Azo dyestuffs and fiber dyed therewith - Google Patents
Azo dyestuffs and fiber dyed therewith Download PDFInfo
- Publication number
- US1941057A US1941057A US318581A US31858128A US1941057A US 1941057 A US1941057 A US 1941057A US 318581 A US318581 A US 318581A US 31858128 A US31858128 A US 31858128A US 1941057 A US1941057 A US 1941057A
- Authority
- US
- United States
- Prior art keywords
- dyestuffs
- stands
- water
- azo dyestuffs
- dyed
- 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
- 239000000835 fiber Substances 0.000 title description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical group [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 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
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
- C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series
Definitions
- the present invention relates to new waterinsoluble azo dyestuffs and to fiber dyed therewith.
- water insoluble azo dyestuifs of a brightness not'lyet attained and of valuable properties as to fastness are obtained, by diazotizing a compound of the general formula:
- the dyeing has a reddish-yellow shade fast .to
- 55- isopropyl'e'b'enzene are diazotized' in the'usualmancbmt of caustic soda solution of 34.Bi this paste 116 boiling, so as to give lliter: u
- v Y wherein .1; stands for halogen, Y stands for hydrogen, --CH3 or --OCH3 and Z stands for hy- 0 drogen or halogen.
- the water-insoluble azo dyestuf is of the following formula CH3 CH3 j g c5 OH H I C: wherein Y stands forhydrogen, CH3 or OCH2 and Z stands for hydrogen or chlorine.
- eo-NEF-Qm CH having a vivid, bluish-red shade, fast to kierboiling.
- X stands for chlorine, bromine or a nitro group and R represents a radical of the benzene or naphthalene. series.
Description
Patented Dec. 26, 1933 v UNITED?" STATES \AZODYESTUFFS mrmnm- 1 THEREW ITHl Q5 Ernst Ruime and Karl Moldaenke, Frankfort-om 1 the-Main-Hochst, and Wetner Kirst, Frankporation .0: Delaware fort-on-the-Main, Germany, assig'nnrs to General Aniline Works, Inc New York, N; Y., a corv No Drawing. Application November 10, 1928, Serial No. 318581, and invGermany November -14, 1927 ZQClair'ns.
The present invention relates to new waterinsoluble azo dyestuffs and to fiber dyed therewith. We have found that water insoluble azo dyestuifs of a brightness not'lyet attained and of valuable properties as to fastness are obtained, by diazotizing a compound of the general formula:
([3113 x NH;
X 1130 CH| wherein X represents chlorine bromine or a nitro group, and coupling it with an arylamide of 2.3
. by wringing out or hydrorextracting and dyed in the dye-bath for hour. The dyed material is rinsed, soaped at the boil, again rinsed and dried.
1. (a) Grounding liquor I 4.5 grammes of 2.3 hydroxynaphthoic acid-2- methyl-4'-chloro-1-anilide are made into a paste with 9 com. of sodium Turkey red oil of 50% strength andQccm. of caustic soda'solution of 34 B,:this paste is covered by pouring boiling (onomo water over it and dissolved "while bo'iling, if iequired, so as to give]. liter. 7 i y -(b) Dye bath 1.84 grammes of2-amino-5-chloro-1-methy1-4- nor with 2.6 ccmfof hydrochloric acid of 22 B- and 0.72 grammes of dissolved sodium nitrite while cooling with ice After the diazotization is complete, the diazo compound is neutralized by means of 2 grammes of dissolved sodium acetate, there are then added 25 grammes of sodium chlorideand the whole is made up with cold water to 1 liter. I The dyeing has a vivid; bluish-red, shade, fast to men-boiling. .The dyestufi has the formula:
OH; on, r \d :CHi.
Q 2.10;) liquor I 3.6 grammes ofdiacetoacetic acid-ortho tolidide are dissolved; while. heating, "with 7.2
grammes of Turkey redjoiI; 5.4 ccm. of caustic soda solution of 34 B and 28 grammes of sodium sulfate so astogivel liter.
@w ww This is prepared in the same manner as that of 'Example 1, except that there .are finally added 2' com. of aceticiacid' of 50% strength; 1
The dyeing has a reddish-yellow shade fast .to
light and to kier-boiling.
ably the formula v11,0 v on;
CH: CH:
4.5 grammes of 2.3 hydroxynaphthoic acid-4'- The dyestuft ihas'probmethoxy-1'-anilide are made into a'paste with 9 room. of Turkey redoil of 50% strength? and 10.5
55- isopropyl'e'b'enzene are diazotized' in the'usualmancbmt of caustic soda solution of 34.Bi this paste 116 boiling, so as to give lliter: u
is poured over with water and dissolved, While 2. The water-insoluble azo dyestuffs of the while cooling with ice.
(b) Dye both CTHa The tints of furtherdyestuifs of the new type herein claimed are stated'in the following table:
following formula:
on. cm
v Y wherein .1; stands for halogen, Y stands for hydrogen, --CH3 or --OCH3 and Z stands for hy- 0 drogen or halogen.
3. The water-insoluble azo dyestufis of the following formula CH3 CH3 j g c5 OH H I C: wherein Y stands forhydrogen, CH3 or OCH2 and Z stands for hydrogen or chlorine.
Combined with the 4. The water-insoluble azo dyestuffs of the following arylamide Shade of the followin formula Diazo compound from of gfiihydmxynapb dyeing g CH3 CH3 7 thou: acid Y 7 V X CH 2-amino-5-oh1oro-1 2-methoxy-4-ch1oro- Scarlet V V methyl 4 isopro 1'-anllide 1 N=N X pylbonzene I Do. 2'5 dimetlioxy l Blulsh-red 0H anilide H36 X Do *ortho-anisidide Scarlet Do. OI'thO-fnlnidirln Bluish-scarlet Do a-naphthy mi n Bluish-red Do di-ottho-anisidide Bordeau-red \CQ NH C1 2 amino 6 nitro '-1 ortlio-anisidide Yellowish-red methyl 4 isopro 1 meme 2' th 1: 151 s It l t Y O -me QXY -0 010- care Y-anili e wherein X stands for chlorine, bromine or a, nitro f' fffigi fiz' f a group, and Y stands for CH3 or -OCH3. r V
' 'di-ortho-anisidide Reddish-orown w 5. The water-insoluble azo dyestuffs of the fol- V lowing formula V e A V CH3 CH3 r r 3 The tints obtained from diazotized 2-am1no-5- V .bromo-1-methyl-4-isopropylbenzene and an 7 N N O1 Jv arylamide of -2.3-hydroxy-naphthoic acid are r very similar to the corresponding dyestuffs ob- 0H CH 1 tained from the fi-chloro-derivative. r 13G We claim: 1. The water-insoluble azo. dyestuffs of the CQ NH l following formula wherein Y stands for OCH3 or -CI-Ia.
. 6. The water-insoluble azo dyestuffs of the following formula CH:\ /GH: x OH V r N===N x OH Z V 7 0H:
' 7 \oO-NHQOI wherein X stands for chlorine, bromine or a nitro I a group, Y stands for. hydrogen, CH or 0c1-I whereinXstands for chlorine, bromine or a nitro and Z stands for hydrogen or halogen.
group.
'7. The water-insoluble azo dyestuff of the following formula 'CH;\ CH: 0
, eo-NEF-Qm CH: having a vivid, bluish-red shade, fast to kierboiling.
8. The water-insoluble azo dyestuffs of the following formula:
wherein X stands for chlorine, bromine or a nitro group and R represents a radical of the benzene or naphthalene. series.
9. The water-insoluble azo dyestuffs of the following formula:
C0-NH-R wherein X stands for halogen, and R. represents 7 claim 1.
a radical of the benzene or naphthalene series. 10. The water-insoluble azo dyestuffs of the following formula:
as claimed in dyed with dyestuffs as claimed in dyed with dyestuffs vas claimed in dyed with dyestuffs as claimed in dyed with dyestufis as claimed in dyed with the dyestuff as claimed in dyed with dyestuffs as claimed in dyed with dyestufis as claimed in claim9.
19. Fiber claim 10.
20. Fiber dyed with dyestuffs as claimed in dyed with dyestuffs as claimed in ERNST RUNNE.
KARL MOLDAENKE. WERNER KIRST.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1941057X | 1927-11-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1941057A true US1941057A (en) | 1933-12-26 |
Family
ID=7750467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US318581A Expired - Lifetime US1941057A (en) | 1927-11-14 | 1928-11-10 | Azo dyestuffs and fiber dyed therewith |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1941057A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2437644A (en) * | 1944-07-31 | 1948-03-09 | American Cyanamid Co | Sulfofluorides of azoic dyestuffs |
-
1928
- 1928-11-10 US US318581A patent/US1941057A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2437644A (en) * | 1944-07-31 | 1948-03-09 | American Cyanamid Co | Sulfofluorides of azoic dyestuffs |
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