US3092435A - Process of dyeing polyethylene and polypropylene materials - Google Patents

Process of dyeing polyethylene and polypropylene materials Download PDF

Info

Publication number
US3092435A
US3092435A US27471A US2747160A US3092435A US 3092435 A US3092435 A US 3092435A US 27471 A US27471 A US 27471A US 2747160 A US2747160 A US 2747160A US 3092435 A US3092435 A US 3092435A
Authority
US
United States
Prior art keywords
anthraquinone
dye
fastness
butylamino
proceeding
Prior art date
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
US27471A
Other languages
English (en)
Inventor
Tessandori Marco
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.)
ACNA Chimica Organica SpA
Original Assignee
ACNA Chimica Organica SpA
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
Application filed by ACNA Chimica Organica SpA filed Critical ACNA Chimica Organica SpA
Application granted granted Critical
Publication of US3092435A publication Critical patent/US3092435A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • C09B1/56—Mercapto-anthraquinones
    • C09B1/58—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals
    • 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
    • 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
    • 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
    • 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
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/79—Polyolefins
    • D06P3/794—Polyolefins using dispersed dyes

Definitions

  • This invention relates to a method for the direct dyeing of synthetic materials obtained by polymerizing monoolefinic hydrocarbons such as ethylene and propylene. The polymer may then be worked to obtain yarns or films.
  • the anthraquinone nucleus may also contain other substituents such as halogens, alkyls, OH, OR,
  • the aflinity for the material to be dyed is so great that it is no longer necessary to use swelling agents or carriers, nor is it necessarry to carry out the dyeing at temperatures in excess of 100 C.
  • Example 1 10 g. of polypropylene fibres are immersed in a dyeing bath containing 0.1 g. of the following compound (1,4- di(butylamino) anthraquinone):
  • the dyeing is carried out at the boiling temperature
  • the fibre is 2 then strongly soaped at 40-60 C.
  • a brilliant blue color with a reddish shade, having high intensity and good fastness, is obtained.
  • Example 2 By proceeding as described in Example 1, but substituting for the 1,4-di(butylamino) anthraquinone, the fibre is dyed an intense brilliant greenish blue color having good cfiastness.
  • Example 3 By proceeding as described in Example 1, but substia very brilliant intense blue color with good fastness is 10 g. of polyethylene film (NI-W. 31,000, determined according to Harris, J. Polymer Science 1952, p. 353) are immersed in a bath containing 0.1 g. of the dye employed in Example 1 and 0.1 g. of ordinary soap. Dyeing is carried out at C.-for 30 minutes. A blue color having good intensity and fastness is obtained.
  • polyethylene film NI-W. 31,000, determined according to Harris, J. Polymer Science 1952, p. 353
  • Dyeing is carried out at C.-for 30 minutes. A blue color having good intensity and fastness is obtained.
  • Example 2 By proceeding as described in Example l'but substituting for the 1,4-dibutylarnino) anthraquinone 0.1 g. of the following compound I O l lHCiHm a blue gray color having good fastnes's is obtained.
  • Example 6 By proceeding as described in Example 1, but substituting for -the l,4-di(butylamino) anthraquinone a compound having the formula /CH3 IfH-OHa-OH a red color with good intensity and fastness is obtained.
  • Example 7 By proceeding as described in Example 1, but substituting NH are H on, ⁇ CHS for the l,4-di(butylamino) anthraquinone, a bordeauxred color having good intensity and fastness is obtained.
  • Example 8 By proceeding as described in Example 1, but substituting for the 1,4-di(butylamino) anthraquinone a blue color with good intensity and iastness is obtained.
  • Example 9 By proceeding as described in Example 1, but substitoting g 7 OH: (H) NH-CHa-C 6 NH-CHn-CH for the 1,4-di(buty1amino) anthraquinone a blue color with good intensity and i'astness is obtained.
  • Example 11 By proceeding as described in Example 1, but substituting I /OHa b NEOH2O for the 1,4-di('butylamino)anthraquinone, a violet color with good intensity and fastness is obtained.
  • Example 12 By proceeding as described in Example 1, but substituting Y for the 1,4-di-(butylamino)anthraquinone, a blue color with good intensity and fastness is obtained.
  • Example 14 By proceeding as described in Example 1, but substituting i O NH-O'Hz-CHrGH;
  • Example 15 By proceeding as described in Example 1, but substituting :for the 1,4-di(hutylamino) anthraquinone, a blue color with good intensity and fastness is obtained.
  • Example 1 6 By proceeding as described in Example 1, but substituting NH-OH for the 1,4-di(butylamino)anthraquinone, a violet color with good intensity and fastness is obtained.
  • Example 17 By proceeding as described in Example 1, but substituting for the 1,4-di(butylamino)anthraquinone, a violet color with good intensity and fastness is obtained.
  • R is selected from the group consisting of alkyl, cycloalkyl, and aryl containing up to 10 carbon atoms, and n is a positive integer from 1 to 6.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US27471A 1959-05-11 1960-05-09 Process of dyeing polyethylene and polypropylene materials Expired - Lifetime US3092435A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT793859 1959-05-11

Publications (1)

Publication Number Publication Date
US3092435A true US3092435A (en) 1963-06-04

Family

ID=11125553

Family Applications (1)

Application Number Title Priority Date Filing Date
US27471A Expired - Lifetime US3092435A (en) 1959-05-11 1960-05-09 Process of dyeing polyethylene and polypropylene materials

Country Status (8)

Country Link
US (1) US3092435A (zh)
BE (1) BE590670A (zh)
CH (1) CH371778A (zh)
DE (1) DE1201295B (zh)
ES (1) ES258127A1 (zh)
FR (1) FR1257940A (zh)
GB (1) GB872882A (zh)
LU (1) LU38619A1 (zh)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3223752A (en) * 1961-05-31 1965-12-14 Monsanto Co Dyeable polyolefin containing modified polyester
US3226177A (en) * 1961-12-02 1965-12-28 Mitsui Kagaku Kogyo Kabushiki Process for the dyeing of polyolefin fibrous materials
US3337288A (en) * 1963-05-06 1967-08-22 Dainichiseika Color Chem Reactive coloring matter, processes for producing the same and processes for coloring articles with the same
US3390947A (en) * 1964-06-24 1968-07-02 Gen Aniline & Film Corp Process for dyeing polyester textile materials with substituted anthraquinone dyestuffs
US3441536A (en) * 1964-09-14 1969-04-29 Allied Chem Synthetic resin compositions containing alpha - phenylthioanthraquinones as colorants
US3485569A (en) * 1966-10-11 1969-12-23 Du Pont Process for dyeing fabric having polypropylene backing and polyamide pile yarns
FR2417527A1 (fr) * 1978-02-17 1979-09-14 Bayer Ag Nouveaux colorants anthraquinoniques non porteurs de groupes nitro et de groupes acide sulfonique
US6126701A (en) * 1999-06-08 2000-10-03 Calogero; Frank Method of dyeing polyolefin fibers

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2036196A (en) * 1933-05-18 1936-04-07 Ici Ltd Application of dyestuffs
US2795477A (en) * 1953-06-24 1957-06-11 Cfmc Coloration of fibres having a polyvinyl derivative base
US2848462A (en) * 1950-10-31 1958-08-19 Saul & Co Dyestuffs of the anthraquinone series
US2895967A (en) * 1958-03-07 1959-07-21 Eastman Kodak Co Metallized anthraquinone dyes
US2900216A (en) * 1955-05-28 1959-08-18 Bayer Ag Process for the dyeing of polymers of acrylonitrile or asymmetric dicyanoethylene
US2952690A (en) * 1957-03-12 1960-09-13 Ciba Ltd Anthraquinone dyestuffs
US2984634A (en) * 1957-01-30 1961-05-16 Eastman Kodak Co Crystalline polymerized monoolefinic hydrocarbons containing metal salt of carboxylic acid

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2036196A (en) * 1933-05-18 1936-04-07 Ici Ltd Application of dyestuffs
US2848462A (en) * 1950-10-31 1958-08-19 Saul & Co Dyestuffs of the anthraquinone series
US2795477A (en) * 1953-06-24 1957-06-11 Cfmc Coloration of fibres having a polyvinyl derivative base
US2900216A (en) * 1955-05-28 1959-08-18 Bayer Ag Process for the dyeing of polymers of acrylonitrile or asymmetric dicyanoethylene
US2984634A (en) * 1957-01-30 1961-05-16 Eastman Kodak Co Crystalline polymerized monoolefinic hydrocarbons containing metal salt of carboxylic acid
US2952690A (en) * 1957-03-12 1960-09-13 Ciba Ltd Anthraquinone dyestuffs
US2895967A (en) * 1958-03-07 1959-07-21 Eastman Kodak Co Metallized anthraquinone dyes

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3223752A (en) * 1961-05-31 1965-12-14 Monsanto Co Dyeable polyolefin containing modified polyester
US3226177A (en) * 1961-12-02 1965-12-28 Mitsui Kagaku Kogyo Kabushiki Process for the dyeing of polyolefin fibrous materials
US3337288A (en) * 1963-05-06 1967-08-22 Dainichiseika Color Chem Reactive coloring matter, processes for producing the same and processes for coloring articles with the same
US3390947A (en) * 1964-06-24 1968-07-02 Gen Aniline & Film Corp Process for dyeing polyester textile materials with substituted anthraquinone dyestuffs
US3441536A (en) * 1964-09-14 1969-04-29 Allied Chem Synthetic resin compositions containing alpha - phenylthioanthraquinones as colorants
US3485569A (en) * 1966-10-11 1969-12-23 Du Pont Process for dyeing fabric having polypropylene backing and polyamide pile yarns
FR2417527A1 (fr) * 1978-02-17 1979-09-14 Bayer Ag Nouveaux colorants anthraquinoniques non porteurs de groupes nitro et de groupes acide sulfonique
US6126701A (en) * 1999-06-08 2000-10-03 Calogero; Frank Method of dyeing polyolefin fibers

Also Published As

Publication number Publication date
BE590670A (zh)
DE1201295B (de) 1965-09-23
ES258127A1 (es) 1960-11-16
CH371778A (de) 1963-10-31
FR1257940A (fr) 1961-04-07
LU38619A1 (zh)
CH530060A4 (zh) 1963-03-29
GB872882A (en) 1961-07-12

Similar Documents

Publication Publication Date Title
US3096140A (en) Process for dyeing polyolefins
US2628963A (en) 1,4-diamino-2,3-anthraquinone-dicarboximides
US3771949A (en) Pretreatment and dyeing of shaped articles derived from wholly aromatic polyamides
US3092435A (en) Process of dyeing polyethylene and polypropylene materials
US2757064A (en) Polyester fibers dyed with anthraquinone dyes
US2882119A (en) Process for dyeing polyester materials
US3328484A (en) Polypropylene or polyester compositions of improved dyeability containing a linear polyamide and a linear sulfonated polyamide
US2952506A (en) Process for even and level dyeing of filament nylon fabrics
US3514246A (en) Method of dyeing shaped polycarbonate resins
US3881865A (en) Anthraquinone dyestuff mixtures
US3918902A (en) Dyeing of synthetic organic material with aliphatic and halogenated aliphatic solution
US3556709A (en) Polyolefin fiber dyeing with an arylazo 8-hydroxy-quinoline-5-sulfonic acid and fibers so dyed
US3658460A (en) Process for dyeing synthetic polyamide textiles in the presence of organic sulphonic acids and basic nitrogen compounds
US3820952A (en) Use of solid carrier for dyeing hydrophobic fibers
US2383995A (en) Colored material
US2760841A (en) Dyeing of mixed cellulose derivative-
US2916345A (en) Process for dyeing articles of polyeth-
GB1029444A (en) New anthraquinone dyestuffs
US3346521A (en) Polyolefin-fusible cellulose ether blends
US3179484A (en) Method for improving the dye-receptivity and dyeability of polypro-pylene
US3877870A (en) Use of solid carrier for dyeing hydrophobic fibers
US3198596A (en) Process for dyeing polypropylene filaments containing inorganic alkaline earth metalcompounds with 1-aminoanthraquinone dyes and the product obtained thereby
US3252749A (en) Process of dyeing polyolefins and other hydrophobic fibers
US3359230A (en) Process for the mass coloration of polyesters
US3390947A (en) Process for dyeing polyester textile materials with substituted anthraquinone dyestuffs