US3211755A - 1-amino-2-benzoyl-4-hydroxy anthraquinone - Google Patents

1-amino-2-benzoyl-4-hydroxy anthraquinone Download PDF

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Publication number
US3211755A
US3211755A US311986A US31198663A US3211755A US 3211755 A US3211755 A US 3211755A US 311986 A US311986 A US 311986A US 31198663 A US31198663 A US 31198663A US 3211755 A US3211755 A US 3211755A
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United States
Prior art keywords
dyeing
benzoyl
amino
fibers
dyestuff
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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
Application number
US311986A
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English (en)
Inventor
Fitzpatrick Joseph William
Wehner Philip
Hildreth John David
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis Corp
Original Assignee
Toms River Chemical Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to BE653575D priority Critical patent/BE653575A/xx
Application filed by Toms River Chemical Corp filed Critical Toms River Chemical Corp
Priority to US311986A priority patent/US3211755A/en
Priority to CH1000564A priority patent/CH448337A/de
Priority to FR988072A priority patent/FR1426169A/fr
Priority to GB37900/64A priority patent/GB1033269A/en
Priority to DET27088A priority patent/DE1279253B/de
Application granted granted Critical
Publication of US3211755A publication Critical patent/US3211755A/en
Assigned to CIBA-GEIGY CORPORATION reassignment CIBA-GEIGY CORPORATION MERGER (SEE DOCUMENT FOR DETAILS). Assignors: TOMS RIVER CHEMICAL CORPORATION
Assigned to CIBA-GEIGY CORPORATION, A CORP. OF N.Y. reassignment CIBA-GEIGY CORPORATION, A CORP. OF N.Y. MERGER (SEE DOCUMENT FOR DETAILS). EFFECTIVE DATE: NOV. 2,1981, STATE OF INCORP. NEW YORK, Assignors: TOMS RIVER CHEMICAL CORPORATION
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C09B1/503—Amino-hydroxy-anthraquinones; Ethers and esters thereof unsubstituted amino-hydroxy anthraquinone

Definitions

  • This invention relates to a novel blue disperse dyestuif of the anthraquinone series and to the use of this dyestuff in coloring polyester materials. More particularly, this invention relates to 1-amino-2 benzoyl-4-hydroxy anthraquinone and to its use in coloring polyester fibers.
  • Polyester fibers present particular dyeing problems, arising at least in part out of the hydrophobic nature of such fibers.
  • the class of dyes known as disperse dyestuffs has come to have the widest application. These dyestulfs are essentially water-insoluble products applied in a finely divided condition from a dispersion.
  • the dyeing difficulties associated with polyester fibers have been met by the development of special methods for the application of disperse dyes to the fibers. Of these methods, the one known as, the Pad/Thermofix method has become of increasing importance since it is particularly adapted for high-speed, continuous dyeing operations.
  • a fabric is padded by passing it through an aqueous suspension of the dyestuff and squeezing the fabric between closely-set rollers in order to remove excess dye liquor.
  • the dyestuff is only loosely attached to the fiber at this point.
  • the dyestuff is then fixed on the fiber by subjecting the material to a short, intensive heat-treatment at elevated temperatures of the order of about 120-220 C. It is evident that a dyestufl, in order to be suitable for application by this method, must be fast to sublimation or else it will wholly or partially volatilize from the fiber during the heat-treatment step. The result of such sublimation will be a loss of color value on the polyester fiber and, if a union dyeing operation is being carried out, the staining of the other fibers, such as cotton, which may be present in the blend.
  • the dyestulf of this invention is of particular interest in that it provides blue dyeings of excellent shade and light fastness on polyester fibers such as polyethylene terephthalate. Blue dyestuffs of satisfactory light fastness properties for use in coloring polyester fibers are difficult to obtain.
  • the said dyestuffs are preferably used in a finely divided form and the dyeing is carried out in the 3,211,755 Patented Oct. 12, 1965 Ice presence of a dispersing agent such as sulfite' cellulose waste liquor or a synthetic detergent, or a combination of different wetting and dispersing agents.
  • a dispersing agent such as sulfite' cellulose waste liquor or a synthetic detergent, or a combination of different wetting and dispersing agents.
  • Dyestuff preparations of this kind can be made by known methods, for example, by grinding the dyestutf(s) either in dry or wet formwith or Without the addition of a dispersing agent.
  • the dyestuff of the present invention is particularly adapted for dyeing by the so-called thermofixation or Pad/ Thermofix method, in which the fabric to be dyed is impregnated advantageously at atemperature not exceeding 60 C. with an aqueous dispersion of the dyestuif, which may contain 1 to 50% of urea and a thickening agent, especially sodium alginate, and the fabric is squeezed in the usual manner.
  • the squeezing is preferably carried out so that the goods retain 50 to of their weight of dye liquor.
  • the dyestuff is fixed by subjecting the impregnated fabric to a heat treatment at temperatures above 100 0., for example, at a temperature ranging from -220 C., it being of advantage to dry the fabric prior to this treatment, for example, in a current of warm air.
  • the padding liquor contains a dyestufi suitable for dyeing cotton, for example, a direct dyestuif or vat dyestuff, or more especially a so-called reactive dyestuff, i.e. a dyestuff capable of being fixed on cellulose fibers with the formation of a chemical bond, for example, a dyestufi containing a chlorotriazine or chlorodiazine residue.
  • a dyestufi suitable for dyeing cotton for example, a direct dyestuif or vat dyestuff, or more especially a so-called reactive dyestuff, i.e. a dyestuff capable of being fixed on cellulose fibers with the formation of a chemical bond, for example, a dyestufi containing a chlorotriazine or chlorodiazine residue.
  • an agent capable of binding acid for example, an alkali carbonate, alkali phosphate, alkali borate or alkali perborate, or a mixture of two or more of these agents.
  • an agent capable of binding acid for example, an alkali carbonate, alkali phosphate, alkali borate or alkali perborate, or a mixture of two or more of these agents.
  • the dyeings produced on polyester fibers by the process of the invention are advantageously given an after-treatment, for example, by heating them with an aqueous solution of a non-ionic detergent.
  • the dyestufls may be applied by printing.
  • a printing colour which in addition to the usual printing assistants such as wetting and thickening agents, contains the finely dispersed dyestuif, if desired, in admixture with one of the foresaid cotton dyestuffs, and, if desired, in the presence of urea and/ or an agent capable of binding acid.
  • polyester defines synthetic polymeric polyesters such as the highly polymeric linear polyesters, the molecules of which have recurring monomeric units connected by ester linkages.
  • Dibasic acids for example, aromatic acids such as terephthalic acid, diphenyl-4,4'-dicarboxylic acid and/or diphenylsulfone-4,4'-dicarboxylic acid and dihydroXy compounds, for example, glycols such as ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol and/ or butylene glycol, as well as other diols, such as 1,4-cyclohexyldiol can be used as the monomers to form the polymeric polyesters.
  • Typical commercial examples of such fibers are Dacron, Terylene, Fortrel, T revira, Terlanca, Kodel, Vycron, etc. They are 3 disclosed, for example, in US. Patent No. 2,901,466 and British Patents Nos. 578,079, 579,462, 588,411, 588,497 and 596,688.
  • the present invention is, of course, equally applicable to the dyeing of blends of polyester fibers and cellulosic fibers.
  • the latter term includes native cellulose, such as linen or more particularly cotton, as well as regenerated cellulose, such as viscose or cuprammonium rayon.
  • Example 1 10.7 parts of boric acid are dissolved in 320 parts of oleum at 50-60" C. with stirring. 30 parts of 1- amino-2-benz0yl-4-bromo anthraquinone are added slowly and the reaction mixture heated slowly to 100 C. over 1 hour and held at 100 C. for a further period of 1 hour. The reaction mixture is then heated quickly to 120 C. and held at 120 C. for 5 hours, dry air being blown through the reaction mixture to remove the bromine gas liberated. At the end of this period, the reaction mixture is cooled to 60 C. and then drowned in 1,000 parts of cold water. The resulting mixture is suction-filtered at 60 C. and then washed with cold water until neutral, followed by drying with warm air. The product, 1- amino-2-benzoyl-4-hydroxy anthraquinone, is obtained as a blue powder in a yield of 26 parts and has the formula:
  • Example 2 parts of the dyestuif of Example 1 are brought to a state of fine dispersion by milling in a ball mill with 2.5
  • a polyester fabric from ethylene glycol and terephthalic acid is then padded with the above liquor and mechanically squeezed to a pick up.
  • the padded material is then air dried and developed by dry heat curing for 1 minute at 200 C.
  • the dyed fabric is then cold rinsed, scoured and finally dried. A bright blue dyeing of excellent light and sublimation fastness and good penetration characteristics is obtained.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US311986A 1963-09-27 1963-09-27 1-amino-2-benzoyl-4-hydroxy anthraquinone Expired - Lifetime US3211755A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
BE653575D BE653575A (is") 1963-09-27
US311986A US3211755A (en) 1963-09-27 1963-09-27 1-amino-2-benzoyl-4-hydroxy anthraquinone
CH1000564A CH448337A (de) 1963-09-27 1964-07-30 Verfahren zur Herstellung neuer 1-Amino-2-benzoyl-4-hydroxyanthrachinone
FR988072A FR1426169A (fr) 1963-09-27 1964-09-14 1-amino-2-benzoyl-4-hydroxyanthraquinones et leur procédé de préparation
GB37900/64A GB1033269A (en) 1963-09-27 1964-09-16 1-amino-2-benzoyl-4-hydroxyanthraquinones and process for their manufacture
DET27088A DE1279253B (de) 1963-09-27 1964-09-25 Verfahren zur Herstellung von 1-Amino-2-benzoyl-4-hydroxyanthrachinonen

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US311986A US3211755A (en) 1963-09-27 1963-09-27 1-amino-2-benzoyl-4-hydroxy anthraquinone

Publications (1)

Publication Number Publication Date
US3211755A true US3211755A (en) 1965-10-12

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US311986A Expired - Lifetime US3211755A (en) 1963-09-27 1963-09-27 1-amino-2-benzoyl-4-hydroxy anthraquinone

Country Status (5)

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US (1) US3211755A (is")
BE (1) BE653575A (is")
CH (1) CH448337A (is")
DE (1) DE1279253B (is")
GB (1) GB1033269A (is")

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3617173A (en) * 1968-06-24 1971-11-02 Toms River Chemical Corp 2-benzoylanthraquinone dyes for polyester fibers

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB661045A (en) * 1948-01-30 1951-11-14 Ciba Ltd Manufacture of anthraquinone derivatives
US2773071A (en) * 1954-01-26 1956-12-04 Interchem Corp Anthraquinone dyes
US2967752A (en) * 1958-05-30 1961-01-10 Sandoz Ltd Blue disperse dyestuffs of the anthraquinone series

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE628695A (is") * 1962-02-21

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB661045A (en) * 1948-01-30 1951-11-14 Ciba Ltd Manufacture of anthraquinone derivatives
US2773071A (en) * 1954-01-26 1956-12-04 Interchem Corp Anthraquinone dyes
US2967752A (en) * 1958-05-30 1961-01-10 Sandoz Ltd Blue disperse dyestuffs of the anthraquinone series

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3617173A (en) * 1968-06-24 1971-11-02 Toms River Chemical Corp 2-benzoylanthraquinone dyes for polyester fibers

Also Published As

Publication number Publication date
CH448337A (de) 1967-12-15
BE653575A (is")
GB1033269A (en) 1966-06-22
DE1279253B (de) 1968-10-03

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AS Assignment

Owner name: CIBA-GEIGY CORPORATION

Free format text: MERGER;ASSIGNOR:TOMS RIVER CHEMICAL CORPORATION;REEL/FRAME:003947/0757

Effective date: 19811102

Owner name: CIBA-GEIGY CORPORATION, A CORP. OF N.Y.

Free format text: MERGER;ASSIGNOR:TOMS RIVER CHEMICAL CORPORATION;REEL/FRAME:004124/0150

Effective date: 19811022

Owner name: CIBA-GEIGY CORPORATION, NEW YORK

Free format text: MERGER;ASSIGNOR:TOMS RIVER CHEMICAL CORPORATION;REEL/FRAME:003947/0757

Effective date: 19811102