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Publication numberUS3188163 A
Publication typeGrant
Publication dateJun 8, 1965
Filing dateJan 22, 1963
Priority dateJan 22, 1963
Publication numberUS 3188163 A, US 3188163A, US-A-3188163, US3188163 A, US3188163A
InventorsJr Joseph W Dehn, Harold J Kuhefuss
Original AssigneeInterchem Corp
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Blue dyed polypropylene fibers and process of dyeing them
US 3188163 A
Abstract  available in
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Claims  available in
Description  (OCR text may contain errors)

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.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2051004 *Sep 10, 1934Aug 11, 1936Gen Aniline Works IncProcess of producing n-substitution products of 1, 4-diaminoanthraquinones
US2131098 *Sep 20, 1935Sep 27, 1938Dreyfus HenryColoration of materials
US2152191 *Oct 28, 1936Mar 28, 1939Nat Aniline & Chem Co IncPreparation of di(arylamino) anthraquinones
US2596820 *Apr 13, 1949May 13, 1952Allied Chem & Dye Corp2, 3, 5, 6, tetramethyl anilino anthraquinones and method of making the same
US2605269 *Feb 23, 1950Jul 29, 1952Du Pont2, 3 xylidinoanthraquinone compounds and sulfonation products thereof
US2736731 *Apr 27, 1953Feb 28, 1956Sandoz AgDyes of the anthraquinone series which are fast to milling and process for their preparation
US2893985 *May 15, 1956Jul 7, 1959Sun Oil CoPolymerization of olefins
US3052510 *Dec 11, 1959Sep 4, 1962Reeves BrothersArt of dyeing synthetic polymeric
US3059987 *May 12, 1960Oct 23, 1962Koppers Co IncDyeing expanded polystyrene articles with disperse dyes
GB494802A * Title not available
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3361772 *Jul 19, 1963Jan 2, 1968Otto B May Inc1, 4-dihydroxy-2-[(substituted alkoxy and alkylthio)-alkoxy]-anthraquinones
US3409385 *Sep 21, 1964Nov 5, 1968Interchem CorpAnthraquinone dyed polypropylene fibers
US4083683 *Mar 11, 1977Apr 11, 1978American Color & Chemical CorporationMetal-containing polypropylene dyed with 1,4-bis-(2'-methyl-6'-ethylanilino)anthraquinone
US5593459 *Oct 24, 1994Jan 14, 1997Gamblin; Rodger L.Surfactant enhanced dyeing
US9194988 *Feb 26, 2008Nov 24, 2015Corning IncorporatedLight-polarizing article and dye dispersion and method for making same
US20100060984 *Feb 26, 2008Mar 11, 2010Corning IncorporatedLight-polarizing article and dye dispersion and method for making same
Classifications
U.S. Classification8/679, 8/909, 8/911, 8/908, 8/914, 8/907, 552/258, 8/912
International ClassificationC09B1/503, C09B1/54, C09B67/22, C09B1/515, C09B1/32
Cooperative ClassificationY10S8/911, Y10S8/909, C09B1/5155, C09B1/5035, Y10S8/912, C09B1/515, C09B67/0038, Y10S8/907, Y10S8/908, Y10S8/914, C09B1/503, C09B1/325, C09B1/545
European ClassificationC09B1/54D, C09B1/515, C09B1/515B, C09B1/32B, C09B1/503B, C09B67/00M1D, C09B1/503