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

Process of dyeing polyethylene and polypropylene materials Download PDF

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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
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anthraquinone
dye
fastness
butylamino
proceeding
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US27471A
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Tessandori Marco
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ACNA Chimica Organica SpA
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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
    • 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.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Description

3 ,092,435 1 Patented June 4, 1963 3,092,435 PROCESS OF DYEING POLYETHYLENE AND POLYPROPYLENE MATERIALS Marco Tessandori, Milan, Italy, assignor to Aziende Colori Nazionali Aifini S.p.A., Milan, Italy, a corporation of Italy No Drawing. Filed May 9, 1960, Ser. No. 27,471 Claims priority, application Italy May 11, 1959 23 Claims. (Cl. 84)
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.
Heretofore it has not been possible to obtain satisfactory dyeing of articles made of polyethylene or polypropylene. This difficulty has been ascribed to the fact that these substances do not contain reactive or polar atoms or atom groups, whereas polymers exhibiting such polarity or reactivity can form bonds of varied nature with dyes.
The use of plastosoluble dyes which under certain conditions will dissolve in materials containing no reactive groups, such as, e.-g., polyethylene and polypropylene, has not proven satisfactory because the resulting dyepolymer solutions obtained have exhibited little or no fastness.
It is therefore an object of this invention to provide a method for the direct dyeing of synthetic materials obtained by polymerizing mono-olefinic hydrocarbons such as ethylene and propylene, whereby the dyed polymer exhibits good intensity and fastness. Additional objects will become apparent hereinafter.
I have found that certain dyes of the anthraquinone type are particularly suitable for the direct dyeing of polyalkylene hydrocarbons such as polyethylene or polypropylene materials. These anthraquinonetype dyes contain in the a position at least one alkyl amino or cycloalkyl amino group, in which the alkyl portion thereof contains from 2 to 18 carbon atoms. The alkyl portion preferably contains from 3 to 6 carbon atoms and is of the branched type.
The anthraquinone nucleus may also contain other substituents such as halogens, alkyls, OH, OR,
CONH NH or NHR (where R is an alkyl, cycloalkyl or an aryl group containing not more than 10 carbon atoms and n is a whole number from 1 to 6) which constituents are capable of comprising particular characteristics of color and fastness.
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.
The following examples further illustrate this invention. All parts are by weight unless otherwise indicated.
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):
A NH(CH2)3CH3 and 0.1 g. of common soap.
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.
In contrast, by proceeding as in Example 1, but substituting l,4-dirnethylamino anthraquinone,
g NHOH Blue Celliton B, Color Index N. 61500) 'for the 1,4- di(bu-tylamino) anthraquinone of Example 1, the fibre is not dyed with satisfactory intensity.
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.
In contrast, when the following compound is used as a dye:
II o NHOH:
(Somalia Blue G, Color Index N. 611525) the fibre is not dyed with satisfactory intensity.
' 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.
Example 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.
7 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 10 for the l,4-di(butylamin0) anthraquinone, a. violet color With good intensity and fastness 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 13 By proceeding as described in Example 1, but substiiuting (l) NH:
for the l,4-di(butylamino)anthraquinone, a violet-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;
for the l,4-di( butylamino) anthnaquinone, a blue color with good intensity and fastness is obtained.
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.
Variations can, of course, be made without departing from the spirit of this invention.
Having thus described this invention, what I desire to secure and claim by Letters Patent is:
1. A method for the direct dyeing of a synthetic material obtained by polymerizing a mono-olefinic hydrocarbon, this process consisting essentially of treating a shaped article of said material with an anthraquinone dye containing an alpha substituent selected from the group consisting of alkylamino and cycloalkylamino groups, the alkyl portion thereof containing from 2 to 18 carbon atoms.
2. The method of claim 1 wherein the synthetic material is polyethylene.
3. The method of claim 1 wherein the synthetic material is polypropylene.
4. The method of claim 1 wherein the alkyl portion contains from 3 to 6 carbon atoms.
5. The method of claim 1 wherein the alkyl amine group is branched.
6. The method of claim 1 wherein the cycloalkyl portion is selected from the group consisting of cyclohexyl and substituted cyclohexyl.
7. The method of claim 1 wherein the anthraquinone ring of the dye contains in addition to the said alpha substituent, at least one other substituent selected from the group consisting of halogen, alkyl, OH, OR,
SR, R, CN, CONH NH and NHR, where 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.
8. The method of claim 1 wherein the dye is 1,4 di (butylamino) anthraquinone.
9. The method of claim 1 wherein 1-to1ylamino-4- butylamino-anthraquinone is used as the dye.
10. The method of claim 1 wherein 1,4-di(cyclohexylamino) anthraquinone is used as the dye.
11. The method of claim 1 wherein 1-amino-2-bromo- 4-butylamino-anthraquinone is used as the dye.
12. The method of claim 1 wherein l-isobutylaminoanthraquinone is used as the dye.
13. The method of claim 1 wherein 1,5-di(isobutylamino) anthraquinone is used as the dye.
14. The method of claim 1 wherein l-cyclohexylamino- 4-isobutylamino-anthraquinone is used as the dye.
15. The method of claim 1 wherein 1-hydroxy-4-cyc1ohexylamino-anthraquinone is used as the dye.
16. The method of claim 1 wherein 1-hydroxy-4-isobutylamino-anthraquinone is used as the dye.
17. The method of claim 1 wherein 1,4-di(isobutylamino)anthraquinone is used as the dye.
18. The method of claim 1 wherein 1-amino-4-propylamino-anthraquinone is used as the dye.
19. The method of claim 1 'Wherein l-amino-Z-cyano- 4-propylamino-anthraquinone is used as the dye.
20. The method of claim 1 wherein 1-amino-2carbamyl-4-propylamino-anthraquinone is used as the dye.
21. The method of claim 1 wherein 1,4-di(isopropylamino)-anthraquinone is used as the dye.
22. The method of claim 1 wherein 1-hydroxy-4-isopropylamino-anthraquinone is used as the dye.
23. The method of claim 1 wherein 1-hydroxy-4-butylamino anthraquinone is used as the dye References Cited in the file of this patent UNITED STATES PATENTS

Claims (1)

1. A METHOD FOR THE DIRECT DYEING OF A SYNTHETIC MATERIAL OBTAINED BY POLYMERIZING A MONO-OLEFINIC HYDROCARBON, THIS PROCESS CONSISTING ESSENTIALLY OF TREATING A SHAPED ARTICLE OF SAID MATERIAL WITH AN ANTHRAQUINONE DYE CONTAINING AN ALPHA SUBSTITUENT SELECTED FROM THE GROUP CONSISTING OF ALKYLAMINO AND CYCLOALKYLAMINO GROUPS, THE ALKYL PORTION THEREOF CONTAINING FROM 2 TO 18 CARBON ATOMS.
US27471A 1959-05-11 1960-05-09 Process of dyeing polyethylene and polypropylene materials Expired - Lifetime US3092435A (en)

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BE (1) BE590670A (en)
CH (1) CH371778A (en)
DE (1) DE1201295B (en)
ES (1) ES258127A1 (en)
FR (1) FR1257940A (en)
GB (1) GB872882A (en)
LU (1) LU38619A1 (en)

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 (en) * 1978-02-17 1979-09-14 Bayer Ag NEW ANTHRAQUINONIC DYES THAT DO NOT CONTAIN NITRO GROUPS AND SULPHONIC ACID GROUPS
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 (en) * 1978-02-17 1979-09-14 Bayer Ag NEW ANTHRAQUINONIC DYES THAT DO NOT CONTAIN NITRO GROUPS AND SULPHONIC ACID GROUPS
US6126701A (en) * 1999-06-08 2000-10-03 Calogero; Frank Method of dyeing polyolefin fibers

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CH371778A (en) 1963-10-31
CH530060A4 (en) 1963-03-29
ES258127A1 (en) 1960-11-16
FR1257940A (en) 1961-04-07
LU38619A1 (en)
DE1201295B (en) 1965-09-23
GB872882A (en) 1961-07-12
BE590670A (en)

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