US2957225A - Fiber of poly - Google Patents

Fiber of poly Download PDF

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Publication number
US2957225A
US2957225A US582632A US58263256A US2957225A US 2957225 A US2957225 A US 2957225A US 582632 A US582632 A US 582632A US 58263256 A US58263256 A US 58263256A US 2957225 A US2957225 A US 2957225A
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Prior art keywords
polymer
percent
pentene
methyl
poly
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US582632A
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English (en)
Inventor
Frank J Welch
Frederick P Reding
Andrew T Walter
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Union Carbide Corp
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Union Carbide Corp
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Priority to BE557115D priority Critical patent/BE557115A/xx
Application filed by Union Carbide Corp filed Critical Union Carbide Corp
Priority to US582632A priority patent/US2957225A/en
Priority to DEU4514A priority patent/DE1108851B/de
Priority to GB13669/57A priority patent/GB823309A/en
Priority to FR1174518D priority patent/FR1174518A/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F10/14—Monomers containing five or more carbon atoms
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/02—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D01F6/04—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds from polyolefins

Definitions

  • the present invention relates to novel polymeric fibers and methods of making the same. More particularly it relates to poly(4-methyl-1-pentene) fibers, and methods employed in the preparation thereof.
  • the present invention also includes processes for preparing fibers from poly(4-methyll-pentene), and particularly high molecular weight fibers of a high degree of crystallinity.
  • filamentary material may be prepared from 4-methyl-l-pentene homopolymer having a melt index of 0.1 to 40 by extruding the said polymer through a spinneret at a temperature from about 260 C. to 350 C. to form a continuous fiber. This extruded product is then stretched to two to eight times its length at a temperature of 50 C. to 220 C.
  • the stretched-oriented fibers prepared from poly(4- methyl-l-pentene) by the process of the present invention have an ultimate elongation at break of at least 15 percent and up to approximately 30 percent and a tensile strength at break of at least 1.5 grams per denier. In its preferred embodiment, however, these fibers have an ultimate elongation at break of about 18 percent and a. tensile strength of 6 g.p.d.
  • a sample of poly(4-methyl-l-pentene), in granular or flaked form is charged to a suitable melting device such as, for example, a melt grid or extruder and fed in the molten conditions to a metering pump.
  • the polymer that is discharged at a constant rate from the metering pump is forced through a suitable filtering medium, such as a sand-pack, and thence through a spinning die having one or more (up to about 250) orifices.
  • a suitable filtering medium such as a sand-pack
  • the molten polymer filaments which are formed in this manner are then extenuated while still in the molten state to reduce their diameter and are then rapidly cooled in a stream of air or cool fluid medium and wound onto a bobbin to form a suitable yarn package.
  • the spun yarn is then stretched and oriented to improve its properties in the following manner: The spun yarn is withdrawn from the package and passed around an advancing roll (godet) to control the rate of feed to the stretching zone.
  • the yarn is stretched while passing through a heated zone by a second godet rotating with a higher surface speed than the first godet.
  • the yarn may be heated by radiation or by contact with a surface or a hot fiuid medium of suitable temperature (i.e., 50 C. to 220 C.).
  • suitable temperature i.e., 50 C. to 220 C.
  • the stretched yarn is then rewound onto a suitable bobbin for subsequent textile operations.
  • suitable temperature i.e. 50 C. to 220 C.
  • Polymeric fibers made in accordance with the present invention having a high melting point, a considerable degree of crystallinity (i.e., at least 50 percent, with a preferred range extending from about percent to about percent for the purified polymer), and a high degree of toughness and strength are of particular value for use in textile yarns.
  • the crystalline polymers preferably employed in forming the fibers of the present invention are obtained from the reaction product containing a mixture of amorphous and crystalline poly(4-methyl-1-pentene) by forming the polymer in a suitable solvent (i.e., aromatic and saturated aliphatic hydrocarbons such as hexane, heptane, benzene and the like) or placing it therein, wherein the amorphous polymer is dissolved and the crystalline portion, being insoluble, is separated out.
  • a suitable solvent i.e., aromatic and saturated aliphatic hydrocarbons such as hexane, heptane, benzene and the like
  • Poly(4-methyl'-l-pentene) is prepared by polymerizing 4-methyl-1-pentene in the presence of a catalyst composition composed of a halide (i.e., bromide, fluoride or chloride) of a metal such as, preferably, for example,
  • RAlR titanium, vanadium or tungsten, and a compound of the formula RAlR wherein A1 is aluminum; R is an alkyl group containing at least one carbon atom or hydrogen; and each of R and R is an alkyl group containing at least one carbon atom; and aninert diluent (i.e., a hydrocarbon solvent) to form poly(4-methyl-1-pentene).
  • A1 aluminum
  • R is an alkyl group containing at least one carbon atom or hydrogen
  • each of R and R is an alkyl group containing at least one carbon atom
  • aninert diluent i.e., a hydrocarbon solvent
  • the resultant product polymer poly(4-methyl-l-pentene) is a tough, clear, highly crystalline resin, having a melting point of about 235 C. and a high stiffness measured at room temperature of 150,000 pounds per square inch, as is seen also in Table II below.
  • the polymer has a melt index of approximately 0 at 250 C. and a density of 0.831 gram per cubic centimeter at 25 C
  • the stiffness of the resin at several different temperatures was measured by an Instron tester made by the Instron Engineering Company of Quincy, Massachusetts (Model 37-), at a rate of strain of 10 percent per minute, a force one hundred times that required to stretch the polymer one percent, and the results are as follows:
  • melt index of the polymer sample is the rate, in decigrams per minute, at which the polymer is extruded under these conditions.
  • polymers of high molecular weight extrude more slowly and therefore have a lower melt index.
  • The. polymerizations described herein are conducted in the presence of an inert. diluent which, is selected from the saturated aliphatic, saturated cycloaliphatic and aromatic hydrocarbons and while serving as a solvent for the monomer, need not necessarily function .as such for either the polymer or the catalyst.
  • the diluent must not contain highly polar substituents, (i.e., nitriles and the like) oxygen, sulfur, active hydrogen, (i.e., alcohols, water, certain amines) or olefinic unsaturation which react with the catalyst and consequently inactivate it.
  • Suitable hydrocarbon solvents are, for example, toluene, benzene, xylene, methylcyclohexane, cyclohexane, hexane, heptane, and highly purified'kerosene.
  • Heptane is a preferred diluent.
  • the catalyst employed herein is composed of two components which may or may not react chemically with each other in the reaction mix.
  • the first component is an organometallic compound such as trialkylalumium (triisobutyl aluminum and trioctyl aluminum) wherein the alkyl substituents contain at least one carbon atom and preferably from 2 to 12 carbon atoms.
  • the preferred trialkylaluminum is triiosbutyl aluminum.
  • the second component is a metallic halide such as'titanium tetrachloride, titanium trichloride, titanium dichloride, vanadium tetrachloride, vanadium trichloride, vanadium dichloride, zirconium tetrachloride, titanium tetrafluoride, titanium trifiuoride, titanium tetrabromide, and titanium tribromide. Titanium trichloride is most advantageously employed in this regard.
  • Halides of other metals in Groups IV-B, V-B, or VIB or the Periodic System of the Elements for example, zirconium, hafnium, niobium, tantalum, chromium or molybdenum, could be used in place of the titanium trichloride or other metallic halide.
  • the molecular ratio of the trialkylaluminum to titanium trichloride used to make the catalyst can vary from 0.5 up to 12 or more.
  • the ratio employed is not narrowly critical and may be varied considerably, without adversely affecting the reaction.
  • the polymerization works as well at higher ratios while the preferred ratio for efiicient and economic operation is l to 5.
  • the preferred molecular ratio of the trialkylaluminum to titanium tetrachloride or the ratio of equivalent amounts of other materials as listed hereinabove is somewhat more clearly delineated.
  • a ratio range of from 0.5 to 12 is operable whereas a range of 0.5 to 4 is preferred.
  • the conver-- sions are substantially decreased.
  • the total catalyst concentration in the reaction mix is not critical.
  • the upper limit for catalyst concentration is an economic one, although excess concentrations do tend to lower the molecular weight, while concentrations as low as one millimol of titanium trichloride per liter of diluent, for example, are wholly operative and may be further decreased.
  • polymerization may be conducted at atmospheric pressure in agitator equipped vessels. In such case, air and moisture are excluded by maintaining an inert (e.g., nitrogen) atmosphere. The rate of polymerization is slower at atmospheric pressure.
  • inert e.g., nitrogen
  • the temperature of polymerization has a marked effect on the molecular weight of the polymer. In general, the higher the'temperature,,the lower is the molecular weight. Temperatures ranging from 0 C. to 170 C. operative when employing titanium trichloride .as the cocatalyst, although temperatures from about 25 C. to about 150 C. are most advantageously employed. Yields of polymer are very low at temperatures in excess of 170 C. At temperatures below 25 C., the polymerization rate falls to low values. The polymerization at 50 C. proceeds very well in 4 to 8 hours to give conversions of 85 percent. It all the monomer is charged initially, about 20 percent of the polymer is soluble in hydrocarbons (amorphous fraction). By feeding the monomer slowly as the polymerization proceeds and thus avoiding a large initial concentration of monorner, the
  • insoluble fraction can be increased to 9095 percent.
  • V polymer are obtained. About 50 to 60 percent of the At 25 C., the polymerization proceeds more slowly than at 50 C.
  • titanium trichloride When titanium trichloride is used with triisobutylaluminum and Without avoiding a large initial concen tration of monomer, higher proportions of crystalline polymer is obtained in crystalline form employing titanium tetrachloride to percent for an equivalent amount of titanium trichloride. The remainder is amorphous polymer. For this reason as Well as the fact that the tetrachloride is not so effective at higher temperatures (i.e., C. to C.) with the monomer, titanium trichloride is preferred.
  • Crystallinity is determined by placing the product polymer in hexane, wherein the amorphous polymer is dissolved and the insoluble fraction separated therefrom. This insoluble portion is molded into plaques and X-ray difraction tests run thereon. These tests indicate that this insoluble portion which is employed in fiber-forming operation is about 100 percent Crystallinity.
  • the ratio of crystalline polymer formed in relation to the amount of amorphous polymer formed, is determined by recovery of the amorphous polymer from the hexane solvent by evaporation of the latter.
  • the contents of the reaction vessel are mixed with iopro'panol, methanol or water containing up to 10 percent hydrochloric acid to solubilize the catalyst residue.
  • the polymer is removed by filtration, washed again and dried.
  • the amorphous material can be separated by extracting with any suitable solvent such as, for example, toluene, heptane, hexane, kerosene and diethylether, at room tem perature.
  • the crystalline polymer is insoluble at room temperature and can be recovered by filtration.
  • the amorphous material can be precipitated from the solvent using, for example, methanol or isopropyl alcohol.
  • Examples 1 to -9 inclusive demonstrate the production of 4-methyl-l-pentene homopolymers.
  • Examples 10 and 11 describe the formation of polymeric fibers from the said homopolymer, and while illustrative of the invention, are not to be construed in limiting the scope thereof.
  • EXAMPLE 1 A mixture of 400 milliliters (mL) hexane, 60 grams (g.) 4-methyl-l-pentene, 8 g. triisobutylaluminum and 3.8 g. titanium tetrachloride was divided and charged to two Pyrex bottles. The bottles were capped and placed in a rotating basket in a 40 C. water bath. After 18 hours the bottles were removed and opened. A precipitate had formed which was filtered ofi, washed with isopropyl alcohol and dried. It weighed 18 g. The melt index of the solid was 0, and its density was 0.830. The filtrate of the reaction'mixture was diluted with isopropanol, causing a precipitate to form. This was washed with alcohol and dried. The dry material weighed 9 g. Its melt index was and its density was 0.830.
  • EXAMPLE 2 A mixture of 200 ml. hexane, 30 g. 4-methyl-l-pentene, 4 g. triisobutylaluminum and 1.9 g. titanium tetrachloride was polymerized in a capped Pyrex bottle at 40 C. for 6 /2 hours. The product was worked up in the same fashion as in Example 1. The soluble fraction weighed g., the insoluble fraction 7 g.
  • Example 3 The charge and procedure of Example 1 was repeated, but the polymerization was carried out at 60 C. for 17 hours.
  • the polymer (insoluble fraction) weighed 23 g., its melt index was zero, and its density was 0.830.
  • EXAMPLE 6 The same charge and conditions were used as in Example 5 except that the time of reaction was 16 hours. The polymer was separated into insolubleand solublein-heptane fractions. A total yield of 36 g. represented a 72 percent conversion of which 20 g. or 40 percent was insoluble polymer and 16 g. or 32 percent was soluble.
  • the yield of crystalline material was identical with that in Example 5.
  • the molecular weight of this polymer was higher than that in Example 5 where the amorphous polymer was lost during washing.
  • melt index of this sample was 0.04 and the flow rate was 1.1 measured at 250 C.
  • EXAMPLE 8 The following charges along with 50 g. of 4-methyl-' l-pentene were placed in six separate bottles and were reacted for six hours at 50 C. The techniques of ham dling were the same as in Example .4.- The polymer obtained was about 60 percent insoluble in heptane in all cases.
  • TiOls Triisobutyl- Al/Ti Hexane, Poly(4methylaluminum, g. ml. l-pentene), g.
  • EXAMPLE 10 A sample of poly(4-methyl-l-pentene) prepared as described in Example 5 was melt spun and hand-drawn to a 22-denier monofilament. The polymer was prepared at 50 C. in hexane with a titanium tetrachloridetriisobutylaluminum catalyst, and was evaluated without fractionation or separation of any amorphous polymer that might have been present. The polymer had a melt index of 41 measured at 250 C., a density of about 0.83 and a melting point of about 240 C.
  • the polymer was charged to the experimental plungerextruder, heated to 270 C., and extruded through a 0.047-inch diameter orifice at about 3 feet per minute and a hot-draw ratio of about 10 to l.
  • the spun filament could be stretched by hand from 300 percent to 400 percent over the surface of a metal pin heated to 55 C.
  • the tenacity and elongation of the handstretched filament was 2.3 grams per denier (g.p.d.) and 21 percent, respectively, and the stifiness modulus was very high-85 -g.p.d. Good temperature resistance was a very important feature of this stretched-fiber as indicated by the low shrinkage in boiling water percent) and in 200 C. ai-r (9.5 percent).
  • EXAMPLE 11 Poly(4-methyl-1-pentene) prepared in accordance with Example 6 was charged to the experimental plungerextruder heated to 27029,0 C. and extruded through a, 0.020 inch diameter orifice at about 15 feet per minute. The spun filament was stretched 200 percent over the surface of a metal pin heated to 200 C. The tenacity of the drawn filament was 2.2 to 4.5 g.-pd. with an elongation of 26 to 32 percent. The measured stiffness modulus was 22 to 31 g.p .d. The measured stifiness modulus of 22 to 31 g.p.d. was determined on an Instron Tester (Model T .M'., manufactured by Instron Engineering Corporation).
  • the stretched fiber was subjected to a consistent rate of elongation and that rate in elongation is equal to 50 percent of the initial length of the specimen (l-inch sample) per minute.
  • the stifiness modulus is determined on this curve, so obtained above, at a point that represents a stress of one percent elongation. The value thus .obtained is multiplied by 100 to yield the stifiness modulus as indicated above.
  • a stretched-oriented fiber formed from poly(4- methyl-l-pentene) having a erystallinity of at least 50 percent, said fiber being characterized by an ultimate elongation at break of at least 15 percent, a melting point of about 235 C. to about 240 C., and a tensile strength of at least 1.5 g.p.d.
  • a stretched-oriented fiber formed from purified poly(4-methyl-1-pentene) freed from amorphous polymer and having a crystallinity of at least percent, said fiber being characterized by an ultimate elongation at break of 15 percent to 30 percent, a melting point of about 235 C. to about 240 C., and a tensile strength of at least 1.5 g.p.d.
  • a stretched-oriented fiber formed from purified poly(4-methyl-1-pentene) freed from amorphous polymer and having a crystallinity of about percent, said fiber being characterized by an ultimate elongation at break of 15 percent to 30 percent, a melting point of about 235 C. to about 240 C., and a tensile strength of at least 1.5 'g.p.d.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Artificial Filaments (AREA)
US582632A 1956-05-04 1956-05-04 Fiber of poly Expired - Lifetime US2957225A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
BE557115D BE557115A (en(2012)) 1956-05-04
US582632A US2957225A (en) 1956-05-04 1956-05-04 Fiber of poly
DEU4514A DE1108851B (de) 1956-05-04 1957-04-29 Verfahren zur Herstellung von Fasern oder Faeden aus Poly-(4-methyl-1-penten)
GB13669/57A GB823309A (en) 1956-05-04 1957-04-30 Improved process for making fibres and filaments of poly (4-methyl-1-pentene)
FR1174518D FR1174518A (fr) 1956-05-04 1957-05-03 Procédé de fabrication de matières textiles

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GB (1) GB823309A (en(2012))

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3152380A (en) * 1961-05-05 1964-10-13 Du Pont Process for treating polypropylene fibers
US3303169A (en) * 1962-01-18 1967-02-07 Du Pont High-modulus, high-tenacity, lowshrinkage polyamide yarn
US3332920A (en) * 1962-10-18 1967-07-25 Ici Ltd New copolymers and articles
US3347838A (en) * 1966-04-07 1967-10-17 Ici Ltd Polymers and articles
US3445442A (en) * 1964-06-17 1969-05-20 Hercules Inc High molecular weight poly(4-methyl-1-pentene) fiber
US5169405A (en) * 1991-11-25 1992-12-08 Basf Corporation Multi-colored disperse dyeable fabric: polyester and poly-methyl-olefin blend
US5206315A (en) * 1989-04-10 1993-04-27 Phillips Petroleum Company Process for polymerizing 1-olefins and catalyst therefor
US20100056007A1 (en) * 2005-11-28 2010-03-04 Rabolt John F Method of solution preparation of polyolefin class polymers for electrospinning processing including

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2170439A (en) * 1936-04-02 1939-08-22 Standard Oil Dev Co Elastic fiber
US2210774A (en) * 1936-02-04 1940-08-06 Ici Ltd Fibers from ethylene polymers
US2352328A (en) * 1939-08-03 1944-06-27 Kleine Johannes Artificial filament, fiber, and foil
US2605509A (en) * 1945-08-10 1952-08-05 Dow Chemical Co Method of producing elastic thread
US2612679A (en) * 1950-10-23 1952-10-07 Ladisch Rolf Karl Filaments containing fillers
US2674025A (en) * 1949-08-15 1954-04-06 Texiclon Corp Polymeric filaments
US2681903A (en) * 1952-04-16 1954-06-22 Standard Oil Co Polymerization of iso-olefins in cycloparaffin diluents
US2712490A (en) * 1950-06-22 1955-07-05 Rhodiaceta Process for spinning swollen polyvinyl chloride
US2820778A (en) * 1955-12-28 1958-01-21 Basf Ag Production of polymerization products from olefinically unsaturated hydrocarbons
US2825721A (en) * 1953-01-27 1958-03-04 Phillips Petroleum Co Polymers and production thereof

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2210774A (en) * 1936-02-04 1940-08-06 Ici Ltd Fibers from ethylene polymers
US2170439A (en) * 1936-04-02 1939-08-22 Standard Oil Dev Co Elastic fiber
US2352328A (en) * 1939-08-03 1944-06-27 Kleine Johannes Artificial filament, fiber, and foil
US2605509A (en) * 1945-08-10 1952-08-05 Dow Chemical Co Method of producing elastic thread
US2674025A (en) * 1949-08-15 1954-04-06 Texiclon Corp Polymeric filaments
US2712490A (en) * 1950-06-22 1955-07-05 Rhodiaceta Process for spinning swollen polyvinyl chloride
US2612679A (en) * 1950-10-23 1952-10-07 Ladisch Rolf Karl Filaments containing fillers
US2681903A (en) * 1952-04-16 1954-06-22 Standard Oil Co Polymerization of iso-olefins in cycloparaffin diluents
US2825721A (en) * 1953-01-27 1958-03-04 Phillips Petroleum Co Polymers and production thereof
US2820778A (en) * 1955-12-28 1958-01-21 Basf Ag Production of polymerization products from olefinically unsaturated hydrocarbons

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3152380A (en) * 1961-05-05 1964-10-13 Du Pont Process for treating polypropylene fibers
US3303169A (en) * 1962-01-18 1967-02-07 Du Pont High-modulus, high-tenacity, lowshrinkage polyamide yarn
US3332920A (en) * 1962-10-18 1967-07-25 Ici Ltd New copolymers and articles
US3445442A (en) * 1964-06-17 1969-05-20 Hercules Inc High molecular weight poly(4-methyl-1-pentene) fiber
US3347838A (en) * 1966-04-07 1967-10-17 Ici Ltd Polymers and articles
US5206315A (en) * 1989-04-10 1993-04-27 Phillips Petroleum Company Process for polymerizing 1-olefins and catalyst therefor
US5169405A (en) * 1991-11-25 1992-12-08 Basf Corporation Multi-colored disperse dyeable fabric: polyester and poly-methyl-olefin blend
US20100056007A1 (en) * 2005-11-28 2010-03-04 Rabolt John F Method of solution preparation of polyolefin class polymers for electrospinning processing including
US8083983B2 (en) * 2005-11-28 2011-12-27 Rabolt John F Method of solution preparation of polyolefin class polymers for electrospinning processing included

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GB823309A (en) 1959-11-11
BE557115A (en(2012))
DE1108851B (de) 1961-06-15
FR1174518A (fr) 1959-03-12

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