US3526639A - Anthraquinone dyestuffs - Google Patents
Anthraquinone dyestuffs Download PDFInfo
- Publication number
- US3526639A US3526639A US627655A US3526639DA US3526639A US 3526639 A US3526639 A US 3526639A US 627655 A US627655 A US 627655A US 3526639D A US3526639D A US 3526639DA US 3526639 A US3526639 A US 3526639A
- Authority
- US
- United States
- Prior art keywords
- parts
- alkyl
- sulfone
- anthraquinone
- phenyl
- 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
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 title description 3
- 150000004056 anthraquinones Chemical class 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 description 13
- 239000000975 dye Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- -1 4-aminophenyl-propyl Chemical group 0.000 description 6
- 238000004043 dyeing Methods 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000003884 phenylalkyl group Chemical group 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical group O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
- 150000003457 sulfones Chemical class 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- AQXYVFBSOOBBQV-UHFFFAOYSA-N 1-amino-4-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2N AQXYVFBSOOBBQV-UHFFFAOYSA-N 0.000 description 2
- VLJNQFJQILHMIR-UHFFFAOYSA-N 4-(3-methylsulfonylpropyl)aniline Chemical compound CS(=O)(=O)CCCC1=CC=C(N)C=C1 VLJNQFJQILHMIR-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000000802 nitrating effect Effects 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- CJUYSGNZBUFFPT-UHFFFAOYSA-N 4-[2-(1,1-dioxothiolan-2-yl)ethyl]aniline Chemical compound C1=CC(N)=CC=C1CCC1S(=O)(=O)CCC1 CJUYSGNZBUFFPT-UHFFFAOYSA-N 0.000 description 1
- FVXPBEUYCCZFJT-UHFFFAOYSA-N 9,10-dihydroxy-2,3-dihydroanthracene-1,4-dione Chemical compound C1=CC=C2C(O)=C(C(=O)CCC3=O)C3=C(O)C2=C1 FVXPBEUYCCZFJT-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 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
- 238000001256 steam distillation Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 235000010487 tragacanth 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/514—N-aryl derivatives
- C09B1/5145—N-aryl derivatives only amino and hydroxy groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/922—Polyester fiber
Definitions
- the present invention is concerned with new anthraquinone dyestuffs and synthetic materials dyed with them.
- the dyestufis of the present invention have the general formula wherein R signifies alkylene having 1 to 6 carbon atoms, R signifies phenyl, alkyl having 1 to 6 carbon atoms, phenyl alkyl in which the alkyl has up to 6 carbons or alkyl phenyl in which the alkyl has up to 6 carbons, R and R may also be linked with each other to form a tetramethylene sulfone ring with the S0 R is hydrogen or lower alkyl, and the carbons in the phenyl nucleus A as well as in R and R may be substituted by Cl, Br, OH or lower alkoxy. Lower alkyl and lower alkoxy groups have 1 to 3 carbon atoms.
- the foregoing dyes are obtained by condensing 1,4-dihydroxy-anthraquinone, its leuco-compound, or a 1-hydroxy-4-chloroor -bromo-anthraquinone, with an amine having the formula wherein R and R have the meaning given above. They are also obtained when 1-hydroxy-4-amino-anthraquinone is condensed with the chloro or bromo counterpart of the foregoing amine.
- the dyestuffs of the present invention are especially suited for dyeing and printing synthetic materials, such as polyamide, cellulose acetate, or cellulose triacetate, and more particularly polyester materials, such as polyethyleneglycol terephthalate.
- synthetic materials such as polyamide, cellulose acetate, or cellulose triacetate
- polyester materials such as polyethyleneglycol terephthalate.
- the above-mentioned materials can be printed in such manner that the printed articles are steamed in the presence of a carrier at temperatures of about to 100 C., or in the absence of a carrier at about 110 to 140 C., or treated at about 170-230 C. according to the so-called process of thermofixing.
- Dyeing is also suitably effected from an aqueous suspension in the presence of carriers at temperatures of about 100 to 110 C., in the absence of carriers between about 110 to 140 C., as well as according to the so-called process of thermofixing at about 170 to 230 C.
- EXAMPLE 1 A mixture consisting of 450 parts water, 27.0 parts 1,4- dihydroxy-anthraquinone, 27.0 parts leuco-1,4-dihydroxyanthraqunione, 54.3 parts 4-aminophenyl-propyl methyl sulfone, and 1.5 parts boric acid is heated to to for 24 hours.
- the mixture now contains besides the desired dyestufi the leuco-compound of this dyestuif, which leucocompound is oxidized by introducing air for 8 hours after the batch has been further admixed with 1.5 parts copper acetate and 9.0 parts piperidine, and heated to 60.
- the dye is now filtered off with suction and rinsed with water.
- the dye is mixed with 1.000 part water and 234 parts sodium hydroxide solution of 33 B., and stirred at 95 for one hour.
- the dye is again filtered off with suction, washed neutral with water, and dried. It is a blue powder dissolving in concentrated sulfuric acid with a greenish blue color.
- the 4-aminophenyl-propyl methyl sulfone is prepared by adding dimethylsulfoxide to styrene, oxidizing the resultant sulfoxide to the corresponding sulfone, nitrating said sulfone and reducing the nitro group thus introduced to obtain the amine.
- EXAMPLE 2 A mixture consisting of 100 parts water, 50 parts ethanol, 12.0 parts 1,4-dihydroxy-anthraquinone, 6.0
- 25 parts of the purified dye in finely divided form are made up into 1000 parts of a printing paste which contains 60 parts of tragacanth as a thickener, and 75 parts of the sodium salt of a sulfonated castor oil.
- a polyester textile is printed with this paste, dried, fixed in a thermo-fixing frame at 215 for 60 seconds, and then rinsed with water and dried, leaving the fabric with a deep reddish blue print having excellent fastness properties.
- Example 1 The dye thus formed is identical with that of Example 1. When applied to polyester fabrics it yields dyeings 4 which, with regard to their tinctorial properties, are not distinguishable from those of Example 1.
- a dyestuif according to claim 1 and having the formula 5 A dyestuif according to claim 1 and having the formula 6.
- a dyestufi according to claim 1 and having the formula References Cited UNITED STATES PATENTS OTHER REFERENCES Venkataraman: The Chemistry of Synthetic Dyes, vol. II (Academic Press, N.Y., 1952), p. 8125.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC0038722 | 1966-04-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3526639A true US3526639A (en) | 1970-09-01 |
Family
ID=7023410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US627655A Expired - Lifetime US3526639A (en) | 1966-04-06 | 1967-04-03 | Anthraquinone dyestuffs |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3526639A (cs) |
| AT (1) | AT263174B (cs) |
| BE (1) | BE696701A (cs) |
| CH (1) | CH479675A (cs) |
| DE (1) | DE1644502A1 (cs) |
| FR (1) | FR1517583A (cs) |
| GB (1) | GB1116269A (cs) |
| NL (1) | NL6704328A (cs) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB968709A (cs) * | 1961-08-16 | |||
| US2033316A (en) * | 1934-05-19 | 1936-03-10 | Gen Aniline Works Inc | Acid dyestuffs of the anthraquinone series |
| US3078281A (en) * | 1959-03-28 | 1963-02-19 | Basf Ag | Dyestuffs of the anthraquinone series and their production |
-
1966
- 1966-04-06 DE DE19661644502 patent/DE1644502A1/de active Pending
-
1967
- 1967-03-23 NL NL6704328A patent/NL6704328A/xx unknown
- 1967-04-03 US US627655A patent/US3526639A/en not_active Expired - Lifetime
- 1967-04-05 AT AT325567A patent/AT263174B/de active
- 1967-04-05 GB GB15656/67A patent/GB1116269A/en not_active Expired
- 1967-04-05 CH CH478467A patent/CH479675A/de not_active IP Right Cessation
- 1967-04-05 FR FR101566A patent/FR1517583A/fr not_active Expired
- 1967-04-06 BE BE696701D patent/BE696701A/xx unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2033316A (en) * | 1934-05-19 | 1936-03-10 | Gen Aniline Works Inc | Acid dyestuffs of the anthraquinone series |
| US3078281A (en) * | 1959-03-28 | 1963-02-19 | Basf Ag | Dyestuffs of the anthraquinone series and their production |
| GB968709A (cs) * | 1961-08-16 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1644502A1 (de) | 1969-10-23 |
| NL6704328A (cs) | 1967-10-09 |
| CH479675A (de) | 1969-10-15 |
| GB1116269A (en) | 1968-06-06 |
| AT263174B (de) | 1968-07-10 |
| FR1517583A (fr) | 1968-03-15 |
| BE696701A (cs) | 1967-10-06 |
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