US3394144A - 1-amino-2-dicarboximidoalkoxy-4-hydroxyanthraquinones - Google Patents
1-amino-2-dicarboximidoalkoxy-4-hydroxyanthraquinones Download PDFInfo
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- US3394144A US3394144A US490725A US49072565A US3394144A US 3394144 A US3394144 A US 3394144A US 490725 A US490725 A US 490725A US 49072565 A US49072565 A US 49072565A US 3394144 A US3394144 A US 3394144A
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- amino
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- anthraquinone
- compound
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- 239000000047 product Substances 0.000 description 17
- -1 anthraquinone compounds Chemical class 0.000 description 15
- 229920000728 polyester Polymers 0.000 description 15
- 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 description 14
- 150000001875 compounds Chemical class 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000975 dye Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000000835 fiber Substances 0.000 description 8
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 150000004056 anthraquinones Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000004753 textile Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 229960002317 succinimide Drugs 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229920002301 cellulose acetate Polymers 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- TWYIPMITVXPNEM-UHFFFAOYSA-N 1-(2-hydroxyethyl)pyrrolidine-2,5-dione Chemical compound OCCN1C(=O)CCC1=O TWYIPMITVXPNEM-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920004934 Dacron® Polymers 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide 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
- 229920004933 Terylene® Polymers 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 229940014800 succinic anhydride Drugs 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
- 238000005292 vacuum distillation Methods 0.000 description 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
- MRGLOEHAJRFNTE-UHFFFAOYSA-N 1-(3-aminopropoxy)ethanol Chemical compound CC(O)OCCCN MRGLOEHAJRFNTE-UHFFFAOYSA-N 0.000 description 1
- KZMBWDGCFLVNTQ-UHFFFAOYSA-N 1-(3-hydroxypropyl)pyrrolidine-2,5-dione Chemical compound OCCCN1C(=O)CCC1=O KZMBWDGCFLVNTQ-UHFFFAOYSA-N 0.000 description 1
- ZGDOXWZYKDETSP-UHFFFAOYSA-N 1-amino-4-hydroxy-9,10-dioxoanthracene-2-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC(S(O)(=O)=O)=C2N ZGDOXWZYKDETSP-UHFFFAOYSA-N 0.000 description 1
- AQXYVFBSOOBBQV-UHFFFAOYSA-N 1-amino-4-hydroxyanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2N AQXYVFBSOOBBQV-UHFFFAOYSA-N 0.000 description 1
- BTLXPCBPYBNQNR-UHFFFAOYSA-N 1-hydroxyanthraquinone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2O BTLXPCBPYBNQNR-UHFFFAOYSA-N 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- HCXMMSVIJXNUQQ-UHFFFAOYSA-N 1-phenoxyanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1OC1=CC=CC=C1 HCXMMSVIJXNUQQ-UHFFFAOYSA-N 0.000 description 1
- MWFLUYFYHANMCM-UHFFFAOYSA-N 2-(2-hydroxyethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCO)C(=O)C2=C1 MWFLUYFYHANMCM-UHFFFAOYSA-N 0.000 description 1
- NQGXOOJUAKCSLM-UHFFFAOYSA-N 2-phenoxyanthracene-9,10-dione Chemical compound C=1C=C2C(=O)C3=CC=CC=C3C(=O)C2=CC=1OC1=CC=CC=C1 NQGXOOJUAKCSLM-UHFFFAOYSA-N 0.000 description 1
- IHUYWFRKUCEIJR-UHFFFAOYSA-N 3-(3-hydroxypropyl)pyrrolidine-2,5-dione Chemical compound OCCCC1CC(=O)NC1=O IHUYWFRKUCEIJR-UHFFFAOYSA-N 0.000 description 1
- RPCTYNXSSJMSMO-UHFFFAOYSA-N 3-ethyl-3-hydroxypyrrolidine-2,5-dione Chemical compound CCC1(O)CC(=O)NC1=O RPCTYNXSSJMSMO-UHFFFAOYSA-N 0.000 description 1
- LWLBBGCCSWKJLA-UHFFFAOYSA-N 3-propylpyrrolidine-2,5-dione Chemical compound CCCC1CC(=O)NC1=O LWLBBGCCSWKJLA-UHFFFAOYSA-N 0.000 description 1
- HCXJFMDOHDNDCC-UHFFFAOYSA-N 5-$l^{1}-oxidanyl-3,4-dihydropyrrol-2-one Chemical group O=C1CCC(=O)[N]1 HCXJFMDOHDNDCC-UHFFFAOYSA-N 0.000 description 1
- JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 description 1
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 229920002821 Modacrylic Polymers 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- GHAZCVNUKKZTLG-UHFFFAOYSA-N N-ethylsuccinimide Chemical compound CCN1C(=O)CCC1=O GHAZCVNUKKZTLG-UHFFFAOYSA-N 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000006355 carbonyl methylene group Chemical group [H]C([H])([*:2])C([*:1])=O 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000009991 scouring Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- AUPJTDWZPFFCCP-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCCN(C)CCS([O-])(=O)=O AUPJTDWZPFFCCP-GMFCBQQYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/04—Homopolymers or copolymers of styrene
- C08L25/06—Polystyrene
-
- 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
- C09B1/503—Amino-hydroxy-anthraquinones; Ethers and esters thereof unsubstituted amino-hydroxy anthraquinone
-
- 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
- C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
- C09B1/545—Anthraquinones with aliphatic, cycloaliphatic or araliphatic ether groups
Definitions
- This invention relates to novel anthraquinone compounds and more particularly to anthraquinone compounds, such as anthraquinone dyestuffs, containing a dicarboximido radical.
- novel dyestuffs of the invention have the general formula wherein R represents a 1-amino-4-hydroxyanthraquinone radical, e.g. a radical having the structure:
- R represents a straight or branched-chain alkylene radical, e.g. methylene, ethylene, propylene, butylene, 2,2- dimethyl-propyl, isobutyl and the like; cycloalkylene e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like; or alkylene-oxyalkylene, e.g. C H OC H C H OC H and the 1ike;
- R represents a dicarboxirnido radical, e.g. a radical havin g the structure:
- o halophenylene e.g.
- novel anthraquinone dyes of the invention may be prepared by several methods, including:
- the first method is preferred as will be shown in the following examples:
- Example 2 Preparation 0t N-3- hydroxypropylsuccinimide The procedure of Example 1 was repeated, substituting an equimolar quantity of 3-aminopropanol-1 for Z-aminoethanol. Vacuum distillation of the reaction mixture yielded 111.8 g. of the product.
- Example 3 Preparation of N-3-(2-hydroxyethoxy) propylsuccinimide The procedure of Example 1 was repeated, substituting an equimolar quantity of 3-aminopropoxyethanol for 2- aminoethanol. Vacuum distillation of the reaction mixture yielded 129.1 g. of product.
- Example 4 Preparation of N-2- hydroxyethylphthalimide The procedure of Example 1 was repeated, substituting an equimolar quantity of phthalic anhydride for succinic anhydride. The reaction mixture was diluted with 500 ml. methanol. An amount of 133.0 g. of product was obtained, M.P. 125126 C. Evaporation of methanol permitted recovery of an additional 37.6 g. of product, M.P. 123-124 C.
- Example An amount of 5.0 g. of N-2-hydroxyethylsuccinimide, 0.9 g. of l-amino-4-hydroxy-2-phenoxyanthraquinone, and 0.25 g. of potassium hydroxide was heated at l35140 C. for a period of 3 hr., with a slow stream of nitrogen above the surface to aid in the removal of phenol.
- the material was neutralized with acetic acid and diluted with alcohol so that it could be drowned in water and filtered.
- the precipitate was dissolved in acetone and filtered, and the acetone solution was drowned in hexane to precipitate the product.
- the product is 1-amino-4- hydroxy-2-(2 succinimide)ethoxyanthraquinone, which dyes polyesters in a bright, lightfast shade of red, with good resistance to sublimation. It also dyes cellulose acetate in a bright, light-fast shade, only slightly less bluish than the polyester.
- the above compound may also be prepared by using solvents in addition to a large excess of hydroxyethylsuccinimide such as dimethyl sulfoxide or N-methyl pyrrolidone or a mixture of pyridine and dimethyl formamide.
- the product had the structure:
- Example 6 The 3-hydroxypropylsuccinimide in Example 6 was replaced by N-hydroxyethoxypropylsuccinimide.
- the product is 1-amino-4-hyrlroxy-2-[2-(3-succinimidopropoxy)- ethoxy]anthraquinone, which dyes polyesters and cellulose acetate in bright, light-fast shades like those obtained from the compound of Examples 5 and 6.
- the product had the structure:
- Example 8 An amount of 1.10 g. of potassium carbonate and 1.54 g. succinimide was added to 25 ml. dimethyl formamide and heated to C. 0.75 g. of l-amino-2-[2-(2-chloroethoxy)ethoxy] 4 hydroxyanthraquinone was added. After 4.5 hr. at 7580 C., the solution was poured into 60 ml. of Water, with 10 ml. methanol being used to rinse the reactor flask. 10 ml. 5% HCl were used to destroy the alkalinity. The precipitate was filtered out and recrystallized from hot Z-methoxyethauol solution.
- the product was l-amino 4 hydroxy-2-[2-(2-succinimidoethoxy) ethoxy]anthraquinone.
- the red shade on polyesters and cellulose acetate exhibited excellent light-fastness, and the dyeings on polyesters showed no sublimation to heat at 350 F. for one minute.
- Example 9 When the succinimide in Example 8 was replaced by phthalimide, and the anthraquinone intermediate in EX- ample 8 was replaced by l-amino-Z-(2-chloro)ethoxy-4- hydroxyanthraquinone, the product was 1-amino-4- hydroxy-2-(2-phthalimido)ethoxyanthraquinone. The same compound was obtained by reacting 1-amino-4-hydroxy' 2-phenoxy-anthraquinone with N-Z-hydroxyethyl phtha limide. The product had the structure:
- l-amino 4 hydroxy-2-(2-succinimido)ethoxyanthraquinone was prepared from the corresponding anthraquinone sulfonic acid by the following method: 4.0 g. of potassium hydroxide, 15 ml. of N-methylpyrrolidine, 2.0 g. of 1-amino-4-hydroxyanthraquinone-2-sulfonic acid, sodium salt and 5.0 g. of N-2-hydroxyethylsuccinimide were reacted at l20-125 C. for 8 hr.
- the anthraquinone compounds of the invention may be used for imparting bright red dyeings of excellent fastness to hydrophobic fibers such as linear polyester, cellulose ester, acrylic, modacrylic, polyamide, etc., fibers in the manner described in US. Patents 2,880,050, 2,757,064, 2,782,187 and 2,043,827.
- the following example illustrates a method by which the anthraquinone compounds of the invention can be used to dye polyester textile materials.
- 0.1 g. of the dye is dissolved in the dye pot by warming in 5 cc. of ethylene glycol monomethyl ether. A 2% sodium-N-methyl-N-oleyl taurate and 0.5% sodium lignin sulfonate aqueous solution is added, with stirring, until a fine emulsion is obtained. Water is then slowly added to a total volume of 200 cc. 3 cc. of Dacronyx (a chlorinated benzene emulsion) are added and 10 grams of a textile fabric made of Kodel polyester fibers are entered. The fabric is worked 10 minutes Without heat and then for 10 minutes at C. The dye bath is then brought to the boil and held at the boil for one hour.
- Dacronyx a chlorinated benzene emulsion
- the fabric is rinsed in warm water, then scoured in aqueous 0.20% soap, 0.2% soda ash solution. After scouring, the fabric is rinsed With Water and dried.
- the anthraquinone compounds of the invention are water-insoluble, they can be applied from aqueous dispersions in the manner of the so-called dispersed dyes.
- coloration can also be effected, for example, by incorporating the anthraquinone compounds into the spinning dope and spinning the fiber as usual.
- the anthraquinone compounds of our invention have varying utility as dyes. The degree of utility varies, for example, depending upon the material being dyed and the formula of the anthraquinone compound. Thus, for example, all the dyes will not have the same degree of utility for the same material.
- Polymeric linear polyester materials of the terephthalate type are illustrative of the linear aromatic polyester textile materials that can be dyed with the new anthraquinone compounds of our invention.
- the terephthalate fibers sold under the trademarks Kodel, Dacron, and Terylene, for example, in the form of filaments, yarn and fabric, for example, are illustrative of the polyester textile materials that can be dyed.
- Kodel polyester fibers are more particularly described in US. Patent 2,901,446. Dacron and Terylene polyester fibers are described, for example, US. Patent 2,465,319.
- the polymeric linear polyester materials disclosed in Us. Patents 2,945,010, 2,957,745 and 2,989,363 for example, can be dyed.
- the linear aromatic polyester materials specifically named have a melting point of at least 200 C.
- Nylon in fiber, yarn and fabric form, is representative of polyamides which can be dyed with the compounds.
- a compound having the formula 0 NH, II I ll 0 OH wherein R straightor branchedchain alkylene of 1 to 5 carbon atoms, 1,4-cyclohexylenedimethylene,
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
- Indole Compounds (AREA)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US490725A US3394144A (en) | 1965-09-27 | 1965-09-27 | 1-amino-2-dicarboximidoalkoxy-4-hydroxyanthraquinones |
GB41910/66A GB1153043A (en) | 1965-09-27 | 1966-09-20 | Anthraquinone Dyes for Synthetic Fibres |
CH1375466A CH468439A (fr) | 1965-09-27 | 1966-09-23 | Procédé de préparation de dérivés de l'anthraquinone |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US490725A US3394144A (en) | 1965-09-27 | 1965-09-27 | 1-amino-2-dicarboximidoalkoxy-4-hydroxyanthraquinones |
Publications (1)
Publication Number | Publication Date |
---|---|
US3394144A true US3394144A (en) | 1968-07-23 |
Family
ID=23949209
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US490725A Expired - Lifetime US3394144A (en) | 1965-09-27 | 1965-09-27 | 1-amino-2-dicarboximidoalkoxy-4-hydroxyanthraquinones |
Country Status (3)
Country | Link |
---|---|
US (1) | US3394144A (fr) |
CH (1) | CH468439A (fr) |
GB (1) | GB1153043A (fr) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5954843A (en) * | 1998-08-28 | 1999-09-21 | Chevron Chemical Company Llc | Aminocarbamates of polyalkyl or polyalkenyl N-hydroxyalkyl succinimides and fuel compositions containing the same |
US5993497A (en) * | 1998-08-28 | 1999-11-30 | Chevron Chemical Company Llc | Esters of polyalkyl or polyalkenyl N-hydroxyalkyl succinimides and fuel compositions containing the same |
EP0982322A1 (fr) * | 1998-08-28 | 2000-03-01 | Chevron Chemical Company LLC | Ethers de polyalkyl ou polyakenyl n-hydroxyalkyl succinimides et compositions de combustible les contenant |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1915334A (en) * | 1930-10-16 | 1933-06-27 | Du Pont | Fluosilicate of organic heterocyclic bases and process of making it |
US2075359A (en) * | 1930-10-16 | 1937-03-30 | Du Pont | Insecticide |
US3184455A (en) * | 1960-07-14 | 1965-05-18 | Bayer Ag | Anthraquinone dyestuffs and process for their production |
-
1965
- 1965-09-27 US US490725A patent/US3394144A/en not_active Expired - Lifetime
-
1966
- 1966-09-20 GB GB41910/66A patent/GB1153043A/en not_active Expired
- 1966-09-23 CH CH1375466A patent/CH468439A/fr unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1915334A (en) * | 1930-10-16 | 1933-06-27 | Du Pont | Fluosilicate of organic heterocyclic bases and process of making it |
US2075359A (en) * | 1930-10-16 | 1937-03-30 | Du Pont | Insecticide |
US3184455A (en) * | 1960-07-14 | 1965-05-18 | Bayer Ag | Anthraquinone dyestuffs and process for their production |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5954843A (en) * | 1998-08-28 | 1999-09-21 | Chevron Chemical Company Llc | Aminocarbamates of polyalkyl or polyalkenyl N-hydroxyalkyl succinimides and fuel compositions containing the same |
US5993497A (en) * | 1998-08-28 | 1999-11-30 | Chevron Chemical Company Llc | Esters of polyalkyl or polyalkenyl N-hydroxyalkyl succinimides and fuel compositions containing the same |
EP0982322A1 (fr) * | 1998-08-28 | 2000-03-01 | Chevron Chemical Company LLC | Ethers de polyalkyl ou polyakenyl n-hydroxyalkyl succinimides et compositions de combustible les contenant |
US6114542A (en) * | 1998-08-28 | 2000-09-05 | Chevron Chemical Company Llc | Ethers of polyalkyl or polyalkenyl N-hydroxyalkyl succinimides and fuel compositions containing the same |
US6352566B1 (en) | 1998-08-28 | 2002-03-05 | Chevron Chemical Company Llc | Ethers of polyalkyl or polyalkenyl N-hydroxyalkyl succinimides and fuel compositions containing the same |
Also Published As
Publication number | Publication date |
---|---|
CH468439A (fr) | 1969-02-15 |
GB1153043A (en) | 1969-05-21 |
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