US3423161A - Dyeable chloromethylstyrene-vinylgrafted polypropylene fibers and process of producing same - Google Patents

Dyeable chloromethylstyrene-vinylgrafted polypropylene fibers and process of producing same Download PDF

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US3423161A
US3423161A US156132A US3423161DA US3423161A US 3423161 A US3423161 A US 3423161A US 156132 A US156132 A US 156132A US 3423161D A US3423161D A US 3423161DA US 3423161 A US3423161 A US 3423161A
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fiber
chloromethylstyrene
polypropylene
fibers
preformed
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Catherine S H Chen
Evalyn F Hosterman
Robert F Stamm
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Wyeth Holdings LLC
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American Cyanamid Co
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
    • D06M14/18—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation
    • D06M14/26—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation on to materials of synthetic origin
    • D06M14/28—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation on to materials of synthetic origin of macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds

Definitions

  • the present invention relates to a light and thermally stable, chemically modified, preformed polypropylene fiber. More particularly, it relates to a light and thermally stable, preformed, vinyl-grafted, uniformly dyeable polypropylene fiber, and to methods for preparing the same.
  • preformed polypropylene fibers of high average molecular weight in the range of from about 100,000 to about 500,000 are manifestly unsuitable as textile fibers. They possess undesirably low sticking temperatures in the range of about 140 C. and are found to be heat-unstable, waxy to the touch, nondyeable and, in general, relatively inert to all aftertreatments. For instance, when such fibers are subjected to moderate heat as that developed during ironing of a fabric prepared therefrom, the fibers either discolor, partially fuse or melt. In view of the increased demand for uniformly dyeable, light-stable, heat-stable, high sticking temperature-polypropylene fibers, it would be highly desirable to provide such fibers so as to meet a long-felt need.
  • a heat-stable, light-stable, colorless, uniformly dyeable, preformed polypropylene fiber of good tensile strength is provided utilizing an overall straightforward method in its preparation.
  • the method involves irradiating a chloromethylstyreneswollen, preformed polypropylene fiber in the presence of a polymerizable vinyl monomer and a cross-linking agent. Fiber so-modified is rendered readily dyeable. Reaction of the fiber with a nucleophilic reagent can occur swiftly prior to the dyeing operation and dyestuffs can be more evenly distributed throughout the fiber. Surprisingly, no sticking temperature is observed within the range of 25 C. to 270 C.
  • preformed polypropylene fiber is initially irradiated while causing the fiber to be contacted with a chloromethylstyrene monomer in the presence of a polymerizable vinyl monomer and a cross-linking agent which are provided in specific amounts.
  • Dyeing of such treated fiber can be carried out in the presence of dyestuffs in a suitable organic medium.
  • dyeing can occur in an aqueous medium, in the absence of an organic solvent, usually at temperatures ranging from about 15 C. to
  • a nucleophilic reagent such as an amine, ammonia, an alkali metal sulfite, an alkali metal bisulfite, or an alkali metal sulfide.
  • the preformed polypropylene fiber to be treated is a linear, isotactic polymer of weight-average molecular weight equal to from about 100,000 to about 1,000,000 and, preferably, from about 250,000 to about 750,000.
  • the preformed, untreated fiber possesses a waxy hand and is insoluble in most organic solvents.
  • the fiber can be modified utilizing any one of several techniques.
  • the modification in essence, involves the grafting to the fiber of a mixture of chloromethylstyrene and a vinyl monomer in the presence of a cross-linking agent.
  • One method involves the simultaneous contact of the latter mixture and the preformed polypropylene fiber in the substautial absence of oxygen while subjecting the fiber soswollen with the monomers to ionizing irradiation.
  • Another method for achieving modification of the fiber is to irradiate initially the preformed fiber by means of ionizing radiation to form free radicals throughout the fiber and then to immerse the so-irradiated polymer in the aforementioned monomeric mixture.
  • the latter technique is similarly conducted in the absence of oxygen.
  • Still another method is to irradiate the preformed polymeric fiber in the presence of oxygen-containing gas (e.g., air) to form a mixture of hydroperoxides both on the fiber and in the fiber, and then to heat the latter in the presence of the aforementioned mixture and in the absence of oxygen so as to graft the chloromethylstyrene, vinyl monomer and cross-linking agent on to the polymeric molecules throughout the fiber.
  • oxygen-containing gas e.g., air
  • Radiation utilized in the process of the invention can be of several types.
  • One type is particulate radiation, such as a-particles and ,B-radiation (electrons), obtained from radioactive nuclei or high-energy electrons from machine sources.
  • Another type of radiation may be electromagnetic radiation, such as gamma-rays or X-rays.
  • the preferred source of radiation is a beam of high-energy electrons possessing energies in the range of from about 0.02 mev. to 20 mev., and preferably in the energy range of from about 0.05 mev. to 4 mev.
  • a beam of electrons of 0.5 mev. has been found to be eminently satisfactory for the treatment of most thicknesses of carded staple fiber, tow fiber or even woven fabric.
  • rads are employed in the grafting procedure so as to render the fiber substantially free from the waxy hand as well as to impart enhanced uniform dyeability with little or no attendant loss of mechanical strength. Surprisingly, the original low sticking temperature of the fiber is no longer found. Rather no measurable sticking temperature up to 270 C. is observed.
  • the chloromethylstyrene monomer reactant may be either ortho-, metaor para-chloromethylstyrene or mixtures of the same in various proportions.
  • chloromethylstyrene is exemplified herein, it is understood that a wide variety of styrenes, such as bromomethylstyrene, chloromethylstyrene with other substituents such as halogen, alkyl or aryl groups on the ring, as well as u-haloor a-alkyl-substituted chloromethylstyrenes may be used in the practice of the invention.
  • Illustrative vinyl monomers which may be used in conjunction with the chloromethylstyrene or its analogs are: styrene, methylstyrene, acrylonitrile, rnethylmethacrylate and equivalents thereof.
  • Admixed with the aforementioned monomers are crosslinking agents exemplary of which are: divinyl benzene, bis-methylene acrylamide, triallyl cyanurate, .tetraallyl melamine, hexaallyl melamine and diallyl sebacate.
  • the chloromethylstyrene and vinyl monomer are supplied in sufficient amounts to swell the fiber and simultaneously provide grafts which fall within the following ranges based on the overall weight of the polymeric fiber.
  • the graft provided by the chloromethylstyrene monomer falls within the range of from about 1% to about and preferably between 4% and 8.5%.
  • the graft provided by the vinyl monomer other than the chloromethylstyrene monomer ranges from about 10% to about 30%, and preferably from about 13% to 16%.
  • the cross-linking agent is provided in such amounts as to form a graft contributing to an overall weight increase in the polymer ranging from about 1% to about 10%.
  • the grafting step is carried out heterogeneously in the absence of oxygen.
  • a solid preformed polypropylene fiber and a mixture of a liquid chloromethylstyrene, a polymerizable vinyl monomer and a cross-linking agent are contacted in such an oxygenfree environment.
  • Swelling of the fiber by the aforementioned monomeric mixture is most readily induced by employing increased temperatures, usually between 40 C. and 120 C.
  • an inert gas such as nitrogen or any of the rare gases to expedite the penetration of the monomer mixture into the fiber is also contemplated.
  • the grafting procedure may be carried out heterogeneously by contacting the polypropylene fiber with the monomeric mixture in the vapor phase.
  • So-grafted, preformed, colorless polypropylene fibers possessing, high tensile strength and uniformly enhanced dyeability may be dyed in an organic medium, such as dimethyl'formarnide.
  • the fibers may be dyed in a conventional aqueous environment by causing a nucleophilic or electron-donating reagent in the solid, liquid or gaseous state to react with them, and thereafter subjecting resultant fibers to dyeing at temperatures in the range of from about 20 C. to about 150 C., and preferably from about C. to about 100 C.
  • the nucleophilic reagent can be added to chloromethylstyrenated and styrenated, cross-linked, preformed polypropylene fiber.
  • the so-treated fiber may be added to the nucleophilic reagent, if desired.
  • the order of addition is not critical.
  • the nucleophilic reagent is a normally solid material, such as alkali metal sulfides or sulfites
  • a solvent therefor is employed as a carrier.
  • dimethylformamide can be used for such purpose.
  • the nucleophilic reagent is a liquid, such as certain tertiary amines, diamines, hydroxyamines, pyridines and the like, the latter can be used without any diluent.
  • the nucleophilic reagent is a gas, such as ammonia or trimethylamine, an appropriate solvent therefor can be employed.
  • nucleophilic reagents may be employed in the present invention.
  • Illustrative reagents are: pyridine, a-picoline, ,B-picoline, 'y-picoline or mixtures thereof, trimethylamine, triethylamine, tri-n-propylamine, N,N-dimethylamine, aminotriacetic acid, tri-fihydroxyethylamine, fl-dimethylaminoethyl alcohol, N,N- dimethyl-o (or m-, or p-) toluidine, N,N-dimethylbenzylamine, dimethylaniline, N-ethyl-N-methylaniline, N,N-diethylaniline, quinoline, isoquinoline, dl-nicotine, N,N-din propylaniline, 6 methylquinoline, 2 phenylpyridine, N,N-dimethyl-a- (or 5-) naphthyl
  • so-grafted polymeric fibers can be uniformly dyed without prior nucleophilic reagent pretreatment with acid and direct dyes at about 75 C. to 130 C. in a solvent such as dimethylformamide.
  • the dyes employed are the following: Calcocid Brilliant Scarlet 3 RN (Acid Red 18); Calcocid Fast Red A (Acid Red 88); Calcocid Yellow MCG (Acid Yellow 23); Calcocid Alizarin Green CGN (Acid Green 25); Calcocid Alizarin Blue SAPG (Acid Blue 45); Calcocid Red FC (Direct Red 1) Calcocid Fast Orange 2R (Direct Orange 26); Calcozine Violet N (Direct Violet 1).
  • the grafted material may initially be treated with a n-ucleophilic reagent whereby the fibers are rendered dyeable in standard aqueous dye baths using either an acid or a direct dye.
  • a n-ucleophilic reagent whereby the fibers are rendered dyeable in standard aqueous dye baths using either an acid or a direct dye.
  • the following dyes produce extremely deep shades of true colors: Calcocid Phloxine 2G (Acid Red 1); Calcocid Green B Conc. (Acid Green 1) and Calcodur Turquoise GL (Direct Blue 86).
  • the grafted fiber initially treated with a solubilized alkali metal sulfide or sulfite permits ready dyeability with basic dyestuffs.
  • a solubilized alkali metal sulfide or sulfite permits ready dyeability with basic dyestuffs.
  • the fiber material can be dyed with basic dyes of which the following are illustrative: Calcozine Acrylic Violet 3R, Sevron Blue 2G, Calcozine Acrylic Red 36, Sevron Yellow R.
  • EXAMPLE 1 Twenty-five parts of 3 denier polypropylene tow are placed in a suitable glass ampoule reactor. The latter is attached to a high vacuum line and evacuated. One hundred parts of a mixture consisting of 47.34 parts of chloromethylstyrene, 47.34 parts of styrene and 5.32 parts of divinyl benzene are distilled into the ampoule under reduced pressure of residual gases of about 10- mm. Hg. The reactor is sealed off and its contents allowed to equilibrate overnight.
  • the ampoule and contents are subjected to irradiation with 250 kiloelectron volts, peak value (kevp.), X-rays to a total dose of 0.27M rad at a dose rate of 1.6M rads/hr.
  • the contents are permitted to remain sealed overnight and are then removed from the glass ampoule by breaking the latter.
  • the fiber is washed several times with toluene, then with methanol and dried in an oven at C.
  • a weight gain of 7.6 parts indicates a graft of about 8.5% chloromethylstyrene, 13.6%
  • a portion of these same dyed fibers is potted in polymethylmethacrylate.
  • Several thin cross sections are next prepared by slicing the potted fibers on a microtome. Examination of the cross sections of the fibers by microscopic techniques reveals that about 75% of the fibers are dyed completely to the center. The examination further reveals that fibers which are not dyed all the way through to the center, exhibit dye penetration to at least (or greater than) two-thirds of the radius of each such fiber. In addition, no sticking temperature up to 270 C. is observed.
  • Another portion of the grafted, but undyed fibers is likewise potted and sectioned as above. These sections are examined by transmitted light in an ultraviolet microscope at wavelengths where polychloromethylstyrene absorbs strongly but where polypropylene is essentially transparent. It is observed that at least 90% to 95% of the fibers are grafted all the way to the center. Those fibers which are not grafted all the way to the center exhibit transparent center sections.
  • EXAMPLE 2 Polypropylene tow (25 parts) is placed in one ampoule of a suitable apparatus consisting of two ampoules connected at their necks with a tube which is attached to a high vacuum line. In the other ampoule are added 100 parts of a mixture consisting of 40 parts of methylstyrene, 20 parts of divinyl benzene and 40 parts of chloromethylstyrene. The monomeric mixture is degassed by repeated freeze-evacuate-thaw cycles. The evacuated apparatus is sealed off and the fiber irradiated with 250 kevp. X-rays to a total dose of 1M rad at a dose rate of 1M rad/hr. During irradiation, the monomeric mixture is shielded from X-rays by one-half inch lead shield around the ampoule containing it. Thirty seconds after irradiation is terminated, the monomeric mixture is poured onto the fiber,
  • a polypropylene-grafted fiber weight gain of 7 parts shows a 5.5% graft of the chloromethylstyrene, 14.5% graft of the methylstyrene and 2% of the divinyl benzene.
  • 0.5 part of the grafted fiber is dyed a brilliant blue by 0.005 part Calcocid Alizarin Blue SAPG in 25 parts by volume of dimethylformamide at 120 C. for about one hour.
  • Typical dyes so utilized are: Calcocid Brilliant Scarlet 3N (Acid Red 18), Calcocid Phloxine 2G (Acid Red 1), Calcomine Fast Orange (Direct Orange 26) Calcocid Yellow MCG (Acid Yellow 23), Calcocid Green B Conc. (Acid Green 1), Calcodur Turquoise GL (Direct Blue 86), Calcocid Alizarin Blue SAPG (Acid Blue 45), and Calcozine Violet N Conc. (Direct Violet 1).
  • each of the fibers so-dyed is exposed simultaneously to heat and ultraviolet and visible light in a standard carbon arc fadeometer. Visual examination of each is next performed after 20, 40 and 80 hours. No fading is noticed after 40 hours exposure. Further, each dyed portion is rated in a fadeometer test. This is the same rating given to these specific dyes when they are dyed on wool to deep shades and exposed in the same manner.
  • Each of the dyed fiber samples is color-fast to washing at 160 F. with a 1% soap solution containing 0.1% sodium carbonate.
  • EXAMPLE 3 This example illustrates the treatment of polypropylene powder.
  • polypropylene powder is placed in a suitable ampoule attached to a high vacuum line.
  • Four parts of a mixture comprising 1.5 parts of chloromethylstyrene, 1.75 parts of acrylonitrile and 0.75 part of divinyl benzene are vacuum-distilled onto the powder.
  • the ampoule is then sealed off under a reduced pressure of about 10- mm. Hg and subjected to irradiation with 25 0 kevp. X-rays to a dose of 0.27M rad at a dose rate of 1.6M rads/hr.
  • Polypropylene powder with a 9% graft of chloromethylstyrene, 15% graft of acrylonitrile and 2.1% graft of divinyl benzene is obtained.
  • the grafted powder does not melt below 310 C. while the ungrafted polypropylene powder melts at about 165 C. Further, the grafted powder advantageously exhibits improved antistatic properties. Moreover, it can also be extruded in the usual fashion to form a nondiscoloring polypropylene fiber.
  • EXAMPLE 4 In a suitable glass bottle, carded polypropylene fiber (15 parts), through which nitrogen has been blown for about one hour, is immersed in 160 parts of a mixture consisting of chloromethylstyrene previously purged with nitrogen, parts of methylmethacrylate and 20 parts of divinyl benzene. The mixture is heated to 55 C. for one hour, while nitrogen is bubbled through it, to increase the amount of monomer imbided by the fiber during the process of swelling. The bottle containing the fiber and monomer is tightly stoppered and irradiated with 3 mev. X-rays at a dose rate of 0.4M rad/hr. to a total dose of 0.2M rad.
  • Weight gain after extraction of the fiber with toluene at room temperature shows a 9.5% graft of the chloromethylstyrene, a 16% graft of the methylmethacrylate and a 3% graft of the divinyl benzene.
  • the fiber is readily dyeable to deep shades in dimethylformamide or in aqueous dye baths after treatment with pyridine.
  • So-grafted, pyridine-treated fiber is placed in an atmosphere of air at 23 C. and 50% relative humidity for 48 hours after which it is weighed. It is then placed in an oven at 105 C., cooled and weighed again. The percent moisture regain is defined as the maximum difference in weight observed, multiplied by and divided by the bone-dry weight. Typical data are shown below which are to be compared with the figure of 4% for the material cited in this example.
  • EXAMPLE 5 0.5 part of polypropylene fiber, prepared in accordance with Example 4 above, is heated at 100 C. for one hour in a mixture of 500 parts of dimethylformamide and 1 part of sodium sulfite. The fiber samples are washed with water and dried at 100 C. Portions of each are then dyed in aqueous solutions of each of the following basic dyes:
  • Dyeability is markedly improved over controls which consist of ungrafted, untreated polypropylene fiber and grafted but not treated polypropylene fiber.
  • a process for preparing a dyeable, preformed, colorless, heat-stable polypropylene fiber of good tensile strength which comprises the steps of: subjecting preformed polypropylene fibers in the solid state and in the substantial absence of oxygen environment to high energy ionizing radiation at a temperature between about 70 C. and 150 C.
  • nucleophilic reagent is selected from the class consisting of pyridine, a-picoline, ,B-picoline, a mixture of w, 18-, 'y-picolines, trimethylamine and aminotriacetic acid.
  • nucleophilic reagent is pyridine.
  • nucleophilic reagent is a-picoline.
  • nucleophilic reagent is fi-picoline.
  • nucleophilic reagent is a mixture of 02-, 5-, 'y-picolines.
  • nucleophilic reagent is trimethyla-mine.
  • nucleophilic reagent is aminotriacetic acid
  • a light-stable, heat-stable colorless, cross-linkcd chloromethylstyrene-vinyl-grafted, preformed polypropylene fiber capable of being uniformly dyed substantially to the center of said fiber and possessing good tensile strength, a spongy structure and devoid of a sticking temperature up to at least 270 C. produced by the process of claim 1.

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3927968A (en) * 1972-05-10 1975-12-23 Teijin Ltd Process for producing an ion-exchangeable and solvent-resistant filamentary structure

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US2999056A (en) * 1956-10-04 1961-09-05 Du Pont Irradiation bonding of acidic compounds to shaped polymeric structures
US3006830A (en) * 1957-05-31 1961-10-31 Dow Chemical Co Method for improving the dyeability of fiber-forming cellulose esters
US3012001A (en) * 1957-03-06 1961-12-05 Us Rubber Co Composition of vinyl chloride polymer plus two unsaturated monomers
US3014776A (en) * 1959-06-23 1961-12-26 American Cyanamid Co Low temperature dyeing of acrylic polymers
US3018154A (en) * 1959-09-24 1962-01-23 Allied Chem Colored aromatic polyester material and process of making same
US3022191A (en) * 1956-06-01 1962-02-20 Montedison Spa Shaped articles of propylene polymers having modified surface characteristics and method of making the same
US3218117A (en) * 1961-08-02 1965-11-16 American Cyanamid Co Polypropylene fibers and method for preparing same
US3278255A (en) * 1961-08-02 1966-10-11 American Cyanamid Co Polypropylene fibers and method for preparing same

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3022191A (en) * 1956-06-01 1962-02-20 Montedison Spa Shaped articles of propylene polymers having modified surface characteristics and method of making the same
US2999056A (en) * 1956-10-04 1961-09-05 Du Pont Irradiation bonding of acidic compounds to shaped polymeric structures
US3012001A (en) * 1957-03-06 1961-12-05 Us Rubber Co Composition of vinyl chloride polymer plus two unsaturated monomers
US3006830A (en) * 1957-05-31 1961-10-31 Dow Chemical Co Method for improving the dyeability of fiber-forming cellulose esters
US3014776A (en) * 1959-06-23 1961-12-26 American Cyanamid Co Low temperature dyeing of acrylic polymers
US3018154A (en) * 1959-09-24 1962-01-23 Allied Chem Colored aromatic polyester material and process of making same
US3218117A (en) * 1961-08-02 1965-11-16 American Cyanamid Co Polypropylene fibers and method for preparing same
US3278255A (en) * 1961-08-02 1966-10-11 American Cyanamid Co Polypropylene fibers and method for preparing same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3927968A (en) * 1972-05-10 1975-12-23 Teijin Ltd Process for producing an ion-exchangeable and solvent-resistant filamentary structure

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