US3394144A - 1-amino-2-dicarboximidoalkoxy-4-hydroxyanthraquinones - Google Patents

1-amino-2-dicarboximidoalkoxy-4-hydroxyanthraquinones Download PDF

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Publication number
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
product
anthraquinone
compound
formula
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US490725A
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English (en)
Inventor
Ralph R Giles
Max A Weaver
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to US490725A priority Critical patent/US3394144A/en
Priority to GB41910/66A priority patent/GB1153043A/en
Priority to CH1375466A priority patent/CH468439A/fr
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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,

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  • 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)
US490725A 1965-09-27 1965-09-27 1-amino-2-dicarboximidoalkoxy-4-hydroxyanthraquinones Expired - Lifetime US3394144A (en)

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

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US490725A US3394144A (en) 1965-09-27 1965-09-27 1-amino-2-dicarboximidoalkoxy-4-hydroxyanthraquinones

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Cited By (3)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Patent Citations (3)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

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Publication number Publication date
GB1153043A (en) 1969-05-21
CH468439A (fr) 1969-02-15

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