US3188163A - Blue dyed polypropylene fibers and process of dyeing them - Google Patents

Blue dyed polypropylene fibers and process of dyeing them Download PDF

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US3188163A
US3188163A US253041A US25304163A US3188163A US 3188163 A US3188163 A US 3188163A US 253041 A US253041 A US 253041A US 25304163 A US25304163 A US 25304163A US 3188163 A US3188163 A US 3188163A
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dyeing
bath
polypropylene fibers
sodium
blue
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US253041A
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Jr Joseph W Dehn
Harold J Kuhefuss
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Interchemical Corp
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Interchemical Corp
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Priority to US253041A priority Critical patent/US3188163A/en
Priority to FR938428A priority patent/FR1360646A/en
Priority to GB25673/63A priority patent/GB979565A/en
Priority to CH804063A priority patent/CH449153A/en
Priority to DEJ23981A priority patent/DE1258995B/en
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    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0034—Mixtures of two or more pigments or dyes of the same type
    • C09B67/0038—Mixtures of anthraquinones
    • 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
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/22—Dyes with unsubstituted amino groups
    • 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
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
    • C09B1/325—Dyes with no other substituents than the amino groups
    • 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
    • C09B1/503—Amino-hydroxy-anthraquinones; Ethers and esters thereof unsubstituted amino-hydroxy anthraquinone
    • C09B1/5035—Amino-hydroxy-anthraquinones; Ethers and esters thereof unsubstituted amino-hydroxy anthraquinone only amino and hydroxy groups
    • 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
    • C09B1/515—N-alkyl, N-aralkyl or N-cycloalkyl derivatives
    • 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
    • C09B1/515—N-alkyl, N-aralkyl or N-cycloalkyl derivatives
    • C09B1/5155—N-alkyl, N-aralkyl or N-cycloalkyl derivatives only amino and hydroxy groups
    • 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
    • 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
    • Y10S8/907—Nonionic emulsifiers for dyeing
    • 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
    • Y10S8/908—Anionic emulsifiers for dyeing
    • 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
    • Y10S8/908—Anionic emulsifiers for dyeing
    • Y10S8/909—Sulfonated or sulfated alphatic hydrocarbons
    • 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
    • Y10S8/908—Anionic emulsifiers for dyeing
    • Y10S8/91—Soap
    • Y10S8/911—Sulfonated
    • 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
    • Y10S8/908—Anionic emulsifiers for dyeing
    • Y10S8/912—Arylene sulfonate-formaldehyde condensate or alkyl aryl sulfonate
    • 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
    • Y10S8/913—Amphoteric emulsifiers for dyeing
    • Y10S8/914—Amino carboxylic acids

Definitions

  • This invention relates to blue dyed polypropylene and textiles and to a process for dyeing them.
  • textiles composed of polypropylene fibers may be dyed blue with good strength and build-up, using a more or less conventional method for disperse dyeing, with 1,4-bis(2,4',6-triethylanilino)-anthraquinone.
  • the blue textiles display superior washfastness and lightfastness, and the dye has better afiinity for the fiber than do the commercially available blue dyes now recommended for such dyeings.
  • the compound is one known to the art, but the art had hitherto no knowledge of its value or even of its possible use as a polypropylene dye.
  • the dyeing is conveniently carried out by dispersing 1,4-bis-(2,4f,6'-triethylauilino)-anthraquinone with suitable dispersing agents and immersing the polypropylene textile in the dyebath, heated to around boiling temperature, for an hour or two.
  • the dyed fibers of this invention were evaluated along with dyeings similarly made with the best available commercial blue dyestuffs recommended by the manufacturer of the polypropylene fibers used in these tests. Fibers dyed according to this invention showed definite superiority over those dyed according to the manufacturers recommendations, in washfastness, lightfastness, and ailinity of the dye for the fiber.
  • Example 1 A mixture of 2.00 g. of 1,4-bis-(2',4',6'-triethylanilino)- anthraquinone (a commercially available chemical), 1.00 g. of Marasperse N, and 1.00 g. of Cyclopon AF was ground with a hand muller in the presence of water. The resulting dispersion was dried in an oven at about 0 C. and the dried material was ground to a powder with mortar and pestle. This material was used in a dyebath. Polypropylene cloth of convenient size was scoured 30 minutes at 70 C. in a bath containing an anionic wetting agent, such as Sulframin AB to the amount of about 1% paste diluted with 295 cc.
  • an anionic wetting agent such as Sulframin AB
  • Example 4 The foregoing process was repeated using 200 mg. of dye dispersion instead of 50 mg, thus yielding a 2.0% dyeing instead of a /2% dyeing.
  • the dispersing agent used is not critical; any reasonably efiicient one will do. A few suitable are here listed by way of example.
  • Marasperse N sodium ligno sulfate
  • Marasperse CB partially desulfonated sodium ligno sulfate
  • Blancol N sodium salt of a sulfonated naphthalene and formaldehyde condensate
  • Tamol SN a neutral salt of a complex condensed aryl organic acid
  • Cyclopon AF sodium N-acyl-N-methyl taurate
  • Igepon CN-42 sodium N-cyclohexyl-N-palmitoyl taurate
  • Igepons T-33, T-43, T-5l, T-73, T-77 sodium N-methyl-N-oleyl taurates
  • Igepon TE-42 sodium N-methyl-N-tallow acid taurate
  • anionic and non-ionic surfactants are suitable. No critical limitation appears to exist.
  • suitable surfactants there may be mentioned Sulframin by weight based on the weight of the cloth and 0.25% by weight (same basis) of sodium carbonate.
  • a dyebath was made up, the total amount being about 40 times the weight of the cloth to be dyed.
  • the bath contained 1%, based on the weight of cloth, of Sulframin Example 2 Similarly dyeings were made using 2% of dye based on the weight of cloth. Both /2% and 2% dyeings were used in the evaluation tests.
  • Example 3 mg. of dye dispersion was made into a paste with 5 cc. of a 1% aqueous Triton X-100' solution and the The goods were AB (sodium alkyl benzene sulfonate); Nacconol NR (sodium alkylaryl); Duponol ME (a long chain alcohol sulfate sodium salt); Tergitol NP-9 or Tergitol NP- 40 (nonylphenyl polyethylene glycol ether); Tergitol NP-l4 (or NP-27 or NP-35 or TMN) (other alkylaryl polyglycols); Triton X- (other alkylaryl polyether glycols which are reaction products of tertiary-octyl phe- Duponol RA is a fortified (b) heating the bath to around 200 F. for about 1-2 hours, (c) removing the fiber from the bath and drying.
  • AB sodium alkyl

Description

AB and /2 of dye on the same basis.
United States Patent 3,188,163 BLUE DYED PQLYPROPYLENE FIBERS AND PRUCESS 0F DYEENG THEM Joseph W. Dehn, In, Great Neck, and Harold J. Kuhefuss,
Brooklyn, N.Y., assignors to Interchemical {Imperation, New York, N .Y., a corporation of Ohio No Drawing. Filed Jan. 22, 1963, Ser. No. 253,041
' 2 Claims. (Cl. 8-39) This invention relates to blue dyed polypropylene and textiles and to a process for dyeing them.
We have found that textiles composed of polypropylene fibers may be dyed blue with good strength and build-up, using a more or less conventional method for disperse dyeing, with 1,4-bis(2,4',6-triethylanilino)-anthraquinone. The blue textiles display superior washfastness and lightfastness, and the dye has better afiinity for the fiber than do the commercially available blue dyes now recommended for such dyeings. The compound is one known to the art, but the art had hitherto no knowledge of its value or even of its possible use as a polypropylene dye.
The dyeing is conveniently carried out by dispersing 1,4-bis-(2,4f,6'-triethylauilino)-anthraquinone with suitable dispersing agents and immersing the polypropylene textile in the dyebath, heated to around boiling temperature, for an hour or two.
The dyed fibers of this invention were evaluated along with dyeings similarly made with the best available commercial blue dyestuffs recommended by the manufacturer of the polypropylene fibers used in these tests. Fibers dyed according to this invention showed definite superiority over those dyed according to the manufacturers recommendations, in washfastness, lightfastness, and ailinity of the dye for the fiber.
Example 1 A mixture of 2.00 g. of 1,4-bis-(2',4',6'-triethylanilino)- anthraquinone (a commercially available chemical), 1.00 g. of Marasperse N, and 1.00 g. of Cyclopon AF was ground with a hand muller in the presence of water. The resulting dispersion was dried in an oven at about 0 C. and the dried material was ground to a powder with mortar and pestle. This material was used in a dyebath. Polypropylene cloth of convenient size was scoured 30 minutes at 70 C. in a bath containing an anionic wetting agent, such as Sulframin AB to the amount of about 1% paste diluted with 295 cc. of water. 10 g. of polypropylene cloth was entered in the bath, which was then heated on the steam bath at a temperature of 200 F. for 45 minutes. The cloth was then removed and the dyebath restored to its original volume with warm water. The pH was adjusted to 3.5-4 with formic acid. The cloth was replaced in the bath and dyed at 200 F. for 30 minutes more. A soaping with Duponol RA, a rinse with water, and air drying completed the process.
Example 4 The foregoing process was repeated using 200 mg. of dye dispersion instead of 50 mg, thus yielding a 2.0% dyeing instead of a /2% dyeing.
The dispersing agent used is not critical; any reasonably efiicient one will do. A few suitable are here listed by way of example. Marasperse N (sodium ligno sulfate); Marasperse CB (partially desulfonated sodium ligno sulfate); Blancol N (sodium salt of a sulfonated naphthalene and formaldehyde condensate); Tamol SN (a neutral salt of a complex condensed aryl organic acid); Cyclopon AF (sodium N-acyl-N-methyl taurate); Igepon CN-42 (sodium N-cyclohexyl-N-palmitoyl taurate); Igepons T-33, T-43, T-5l, T-73, T-77 (sodium N-methyl-N-oleyl taurates); Igepon TE-42 (sodium N-methyl-N-tallow acid taurate); Igepon TN-54 (sodium N-methyl-N-pahnitoyl taurate).
Many anionic and non-ionic surfactants are suitable. No critical limitation appears to exist. As examples of suitable surfactants there may be mentioned Sulframin by weight based on the weight of the cloth and 0.25% by weight (same basis) of sodium carbonate.
A dyebath was made up, the total amount being about 40 times the weight of the cloth to be dyed. The bath contained 1%, based on the weight of cloth, of Sulframin Example 2 Similarly dyeings were made using 2% of dye based on the weight of cloth. Both /2% and 2% dyeings were used in the evaluation tests.
Instead of sodium carbonate in the scouring bath other suitable alkalies may be used, the pH of such baths being in the neighborhood of 11-12.
Example 3 mg. of dye dispersion was made into a paste with 5 cc. of a 1% aqueous Triton X-100' solution and the The goods were AB (sodium alkyl benzene sulfonate); Nacconol NR (sodium alkylaryl); Duponol ME (a long chain alcohol sulfate sodium salt); Tergitol NP-9 or Tergitol NP- 40 (nonylphenyl polyethylene glycol ether); Tergitol NP-l4 (or NP-27 or NP-35 or TMN) (other alkylaryl polyglycols); Triton X- (other alkylaryl polyether glycols which are reaction products of tertiary-octyl phe- Duponol RA is a fortified (b) heating the bath to around 200 F. for about 1-2 hours, (c) removing the fiber from the bath and drying.
References Cited by the Examiner UNITED STATES PATENTS 2,051,004 8/36 Koeberleet al. 260-378 2,131,098 9/38 Dreyfus 8-55 7 2,152,191 1 3/39 Herrett 260-378 2,596,820 5/52 Ogilvie 260-378 X 2,605,269 7/52 Buxbaum 260-378 X 2,736,731 2/56 Peter et al. 260-378 X 2,893,985 7/59 Powelson 260-949 3,052,51'0 9/62 Simpson et al. 8-55 3,059,987 10/62 Bauman 8-55 FOREIGN PATENTS 494,802 11/ 38 Great Britain.
NORMAN G. TORCHIN, Primary Examiner. ABRAHAM H. WINKELSTEIN. Examiner.

Claims (1)

  1. 2. PROCESS FOR DYEING POLYPROPYLENE FIBERS BLUE, CONSISTING ESSENTIALLY OF (A) IMMERSING POLYPROPYLENE FIBER IN AN AQUEOUS DYEBATH CONTAINING CONVENTIONAL AMOUNTS OF THE DYE, 1,4-BIS(2'',4'',6''-TRIETHYL ANILINO) ANTHRAQUINONE DISPERSED THEREIN AND A SUITABLE DISPERSING AGENT, (B) HEATING THE BATH TO AROUND 200*F. FOR ABOUT 1-2 HOURS, (C) REMOVING THE FIBER FROM THE BATH AND DRYING.
US253041A 1963-01-22 1963-01-22 Blue dyed polypropylene fibers and process of dyeing them Expired - Lifetime US3188163A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US253041A US3188163A (en) 1963-01-22 1963-01-22 Blue dyed polypropylene fibers and process of dyeing them
FR938428A FR1360646A (en) 1963-01-22 1963-06-18 New Disperse Dyes of the Anthraquinone Series
GB25673/63A GB979565A (en) 1963-01-22 1963-06-27 New disperse anthraquinone dyes
CH804063A CH449153A (en) 1963-01-22 1963-06-28 Process for the preparation of an anthraquinone series dye
DEJ23981A DE1258995B (en) 1963-01-22 1963-06-29 Process for the preparation of anthraquinone dyes

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3361772A (en) * 1963-07-19 1968-01-02 Otto B May Inc 1, 4-dihydroxy-2-[(substituted alkoxy and alkylthio)-alkoxy]-anthraquinones
US3409385A (en) * 1964-09-21 1968-11-05 Interchem Corp Anthraquinone dyed polypropylene fibers
US4083683A (en) * 1977-03-11 1978-04-11 American Color & Chemical Corporation Metal-containing polypropylene dyed with 1,4-bis-(2'-methyl-6'-ethylanilino)anthraquinone
FR2426113A1 (en) * 1978-05-20 1979-12-14 Bayer Ag PROCESS FOR DYING SYNTHETIC FIBERS WITH MIXTURES OF ANTHRAQUINONIC DYES
US5593459A (en) * 1994-10-24 1997-01-14 Gamblin; Rodger L. Surfactant enhanced dyeing
US20100060984A1 (en) * 2007-02-28 2010-03-11 Corning Incorporated Light-polarizing article and dye dispersion and method for making same

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2051004A (en) * 1933-09-19 1936-08-11 Gen Aniline Works Inc Process of producing n-substitution products of 1, 4-diaminoanthraquinones
US2131098A (en) * 1934-09-28 1938-09-27 Dreyfus Henry Coloration of materials
GB494802A (en) * 1936-12-30 1938-11-01 Chemical Works Formerly Sandoz Anthraquinone dyestuffs and a process for their manufacture
US2152191A (en) * 1936-10-28 1939-03-28 Nat Aniline & Chem Co Inc Preparation of di(arylamino) anthraquinones
US2596820A (en) * 1949-04-13 1952-05-13 Allied Chem & Dye Corp 2, 3, 5, 6, tetramethyl anilino anthraquinones and method of making the same
US2605269A (en) * 1950-02-23 1952-07-29 Du Pont 2, 3 xylidinoanthraquinone compounds and sulfonation products thereof
US2736731A (en) * 1952-05-09 1956-02-28 Sandoz Ag Dyes of the anthraquinone series which are fast to milling and process for their preparation
US2893985A (en) * 1956-05-15 1959-07-07 Sun Oil Co Polymerization of olefins
US3052510A (en) * 1962-09-04 Art of dyeing synthetic polymeric
US3059987A (en) * 1960-05-12 1962-10-23 Koppers Co Inc Dyeing expanded polystyrene articles with disperse dyes

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3052510A (en) * 1962-09-04 Art of dyeing synthetic polymeric
US2051004A (en) * 1933-09-19 1936-08-11 Gen Aniline Works Inc Process of producing n-substitution products of 1, 4-diaminoanthraquinones
US2131098A (en) * 1934-09-28 1938-09-27 Dreyfus Henry Coloration of materials
US2152191A (en) * 1936-10-28 1939-03-28 Nat Aniline & Chem Co Inc Preparation of di(arylamino) anthraquinones
GB494802A (en) * 1936-12-30 1938-11-01 Chemical Works Formerly Sandoz Anthraquinone dyestuffs and a process for their manufacture
US2596820A (en) * 1949-04-13 1952-05-13 Allied Chem & Dye Corp 2, 3, 5, 6, tetramethyl anilino anthraquinones and method of making the same
US2605269A (en) * 1950-02-23 1952-07-29 Du Pont 2, 3 xylidinoanthraquinone compounds and sulfonation products thereof
US2736731A (en) * 1952-05-09 1956-02-28 Sandoz Ag Dyes of the anthraquinone series which are fast to milling and process for their preparation
US2893985A (en) * 1956-05-15 1959-07-07 Sun Oil Co Polymerization of olefins
US3059987A (en) * 1960-05-12 1962-10-23 Koppers Co Inc Dyeing expanded polystyrene articles with disperse dyes

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3361772A (en) * 1963-07-19 1968-01-02 Otto B May Inc 1, 4-dihydroxy-2-[(substituted alkoxy and alkylthio)-alkoxy]-anthraquinones
US3409385A (en) * 1964-09-21 1968-11-05 Interchem Corp Anthraquinone dyed polypropylene fibers
US4083683A (en) * 1977-03-11 1978-04-11 American Color & Chemical Corporation Metal-containing polypropylene dyed with 1,4-bis-(2'-methyl-6'-ethylanilino)anthraquinone
FR2426113A1 (en) * 1978-05-20 1979-12-14 Bayer Ag PROCESS FOR DYING SYNTHETIC FIBERS WITH MIXTURES OF ANTHRAQUINONIC DYES
US5593459A (en) * 1994-10-24 1997-01-14 Gamblin; Rodger L. Surfactant enhanced dyeing
US20100060984A1 (en) * 2007-02-28 2010-03-11 Corning Incorporated Light-polarizing article and dye dispersion and method for making same
US9194988B2 (en) * 2007-02-28 2015-11-24 Corning Incorporated Light-polarizing article and dye dispersion and method for making same

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GB979565A (en) 1965-01-06
CH449153A (en) 1967-12-31

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