US3424704A - Treatment of polyolefin-fatty acid salt mixtures with a hydrocarbon or halogenated hydrocarbon to improve dye receptivity - Google Patents

Treatment of polyolefin-fatty acid salt mixtures with a hydrocarbon or halogenated hydrocarbon to improve dye receptivity Download PDF

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Publication number
US3424704A
US3424704A US513570A US3424704DA US3424704A US 3424704 A US3424704 A US 3424704A US 513570 A US513570 A US 513570A US 3424704D A US3424704D A US 3424704DA US 3424704 A US3424704 A US 3424704A
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United States
Prior art keywords
solvent
polyolefin
hydrocarbon
treatment
acid
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Expired - Lifetime
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US513570A
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English (en)
Inventor
Gerrit Schuur
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Shell USA Inc
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Shell Oil Co
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C08K5/098—Metal salts of carboxylic acids
    • 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
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/928—Polyolefin fiber

Definitions

  • the improvement in dyeability is provided by a pretreatment of the metal-containing polyolefin composition, prior to the dyeing steps; the pretreatment consists of contact with an organic solvent in which the maximum solubility of the polyolefin is by weight and the maximum swelling is 15% by volume. Solvents of the type used in dry cleaning are suitable.
  • This invention relates to a process for improving the dyeability of a polyolefin. More particularly, the invention relates to a method of treating a polymer of an alpha monoolefin and especially polypropylene in order to improve its dyeability.
  • the organic solvents used in this invention to treat the polyolefin fibers are those solvents in which the polymers are insoluble or dissolve to a maximum of 5% by weight or swell to a maximum of 15% by volume at room temperature. Conventional dry cleaning solvents are particularly effective.
  • Suitable solvents include halogenated saturated or unsaturated hydrocarbons such as carbon tetrachloride, tricholorethylene, perchloroethylene, aromatic hydrocarbons, such as benzene, toluene, xylene, petroleum distillates such as white spirit, mineral spirits, cleaners naphtha, Stoddard solvent, gasoline, etc., aliphatic hydrocarbons such as isooctane, ligroin, cyclohexane, dioxane, etc.
  • the metal compounds which are present and distributed in the polyolefin are compounds of metals having a valence of at least two as disclosed, for example, in Belgian Patent No. 617,280.
  • Preferred metals are aluminum, zinc and nickel.
  • the preferred metal compounds are salts of higher saturated fatty acids and especially those having from 16 to 20 carbon atoms.
  • Especially preferred compounds are aluminum mono-, dior tristearate.
  • the amount of metal compound is preferably between about 0.02 and 0.2% by weight, based on the metal.
  • the metal is distributed uniformly throughout the polymer by a convenient means such as by thorough blending of the metal compound with the polymer at any stage before extrusion of the resin fiber.
  • the treatment of the metal containing polyolefins may be carried out at room temperature, i.e., about 20 C. and up to about C.
  • the length of time in which the polymer is contacted with the solvent is not critical except that it must be of sufficient time to affect the polymer in order to obtain the desired increase in coloring. Suitable times are bet-ween a few minutes, i.e., about 3 to 5 minutes and up to about an hour. A very short period of time such as 10 to 15 seconds is also unsuitable. Treating times over about one hour are not excluded but in general do not bring about any further increase in polymer colormg.
  • the polymers which are improved according to the invention are polyolefins and especially the polymers of alpha-monoolefins. Particularly improved is highly crystalline or isotactic polypropylene prepared by the well known low pressure methods in the presence of Ziegler type catalysts.
  • the polymer may be in any suitable form such as fibers, filaments, yarns, fabrics, strips, films, sheets, plates, blocks, rods and the like.
  • the solvent is removed as carefully and as thoroughly as possible prior to dyeing or coloring operations.
  • solvent for example, by evaporation at high temperature or by air drying
  • dyeability is improved even to a greater degree.
  • Suitable methods of removing the solvent are, for example, by subjecting the fabrics, fibers, etc. to brushing such as by passing them through one or more brushes or in the case of films, plates, sheets and the like, absorbing the solvent completely on rags, sponges, etc.
  • the material is colored or dyed according to suitable methods well known to those skilled in the art.
  • the dyes and coloring agents which are improved by the process of this invention are those in which in addition to the coloring groups have a hydroxyl group which is present in the form of a hydroxyl or carboxyl group in an ortho position with respect to a carbonyl group, i.e.,
  • dyes of this description are those disclosed in detail in Belgian Patents 617,280, 632,117, 631,326, 632,118 and 632,119. These dyestuffs include azosalicylic acids, diazosalicylic acids, and the corresponding cresotinic acid derivatives and diazorecorsylic acids derived from gamma or beta resorcylic acid.
  • dyestuffs of these types are the following azo dyestufis: 4-acetylbenzeneazosalicylic acid 2,3-dichlorobenzeneazosalicylic acid 4-nitrobenzeneazosalicylic acid 2-trifiuoromethylbenzeneazosalicylic acid 3-trifluoromethylbenzeneazo-o-cresotinic acid 4-fiuorobenzeneazosalicylic acid 3fluorobenzeneazo-m-cresotinic acid Benzeneazobenzeneazosalicylic acid Z-methylbenzeneazo-2-methylbenzeneazosalicylic acid p-Acetophenoneazobenzeneazosalicylic acid 3-chlorobenzeneazobenzeneazosalicylic acid Benzeneazo-gamma-resorcylic acid 3-methylbenzeneazo-gamma-resorcyclic acid Benzeneazo-beta-resorcylic acid 3-methoxy
  • Isotactic polypropylene was mixed with an aluminum fatty acid salt to provide a mixture containing 0.08% by weight aluminum. The mixture was extruded to prepare continuous fibers of 7 and 4 denier.
  • Method A the solvent was removed by air drying at from 20 to 100 C. for from 1 to 24 hours with the higher drying temperatures requiring a shorter drying time.
  • Method B the solvent was carefully removed from the fibers and yarns by passing through a series of brushes.
  • Example II The procedure of Example I was repeated with exception that the samples were not treated with a solvent.
  • a process for preparing polyolefins having improved dyeability which comprises treating a fatty acid metal salt containing polyolefin with an organic solvent in which the maximum solubility of the polyolefin is 5% by weight and maximum swelling of the polyolefin is 15% by voltime and wherein the metal is a polyvalent metal and present in the polyolefin in an amount of between about 0.02 and 0.2% by weight and thereafter removing the solvent from the treated polyolefin.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
US513570A 1965-02-22 1965-12-13 Treatment of polyolefin-fatty acid salt mixtures with a hydrocarbon or halogenated hydrocarbon to improve dye receptivity Expired - Lifetime US3424704A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL6502222A NL6502222A (xx) 1965-02-22 1965-02-22

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US3424704A true US3424704A (en) 1969-01-28

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NL (1) NL6502222A (xx)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101445497B (zh) * 2008-12-22 2012-01-18 湖南海利化工股份有限公司 碱式羧酸铝催化合成呋喃酚的方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2984634A (en) * 1957-01-30 1961-05-16 Eastman Kodak Co Crystalline polymerized monoolefinic hydrocarbons containing metal salt of carboxylic acid
US3257379A (en) * 1962-08-30 1966-06-21 Otto B May Inc Monoazo beta-resorcylic acid dyes
US3322704A (en) * 1963-12-16 1967-05-30 Shell Oil Co Polyolefin-metal salt-lubricant compositions having improved dye receptivity
US3355402A (en) * 1963-09-05 1967-11-28 Mitsubishi Rayon Co Dyeable polypropylene fibers containing aluminum salts

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2984634A (en) * 1957-01-30 1961-05-16 Eastman Kodak Co Crystalline polymerized monoolefinic hydrocarbons containing metal salt of carboxylic acid
US3257379A (en) * 1962-08-30 1966-06-21 Otto B May Inc Monoazo beta-resorcylic acid dyes
US3355402A (en) * 1963-09-05 1967-11-28 Mitsubishi Rayon Co Dyeable polypropylene fibers containing aluminum salts
US3322704A (en) * 1963-12-16 1967-05-30 Shell Oil Co Polyolefin-metal salt-lubricant compositions having improved dye receptivity

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101445497B (zh) * 2008-12-22 2012-01-18 湖南海利化工股份有限公司 碱式羧酸铝催化合成呋喃酚的方法

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Publication number Publication date
NL6502222A (xx) 1966-08-23

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