US3366710A - Modification of stereoregular polyolefins with polyethylene glycol - Google Patents

Modification of stereoregular polyolefins with polyethylene glycol Download PDF

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Publication number
US3366710A
US3366710A US400611A US40061164A US3366710A US 3366710 A US3366710 A US 3366710A US 400611 A US400611 A US 400611A US 40061164 A US40061164 A US 40061164A US 3366710 A US3366710 A US 3366710A
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United States
Prior art keywords
polyolefin
modifiers
stereoregular
polyethylene glycol
modifier
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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
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US400611A
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English (en)
Inventor
Jack J Press
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Individual
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Individual
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Filing date
Publication date
Priority to NL276760D priority Critical patent/NL276760A/xx
Priority to BE616010D priority patent/BE616010A/xx
Priority to FR892895A priority patent/FR1321694A/fr
Priority to GB12826/62A priority patent/GB987421A/en
Priority to LU41492A priority patent/LU41492A1/xx
Priority to US400611A priority patent/US3366710A/en
Application filed by Individual filed Critical Individual
Priority to US406939A priority patent/US3375213A/en
Priority to US414919A priority patent/US3316328A/en
Priority to US433226A priority patent/US3497574A/en
Priority to US502719A priority patent/US3425969A/en
Priority to US502720A priority patent/US3505429A/en
Application granted granted Critical
Publication of US3366710A publication Critical patent/US3366710A/en
Priority to US703784A priority patent/US3484838A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/10—Homopolymers or copolymers of propene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L39/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
    • C08L39/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
    • C08L39/06—Homopolymers or copolymers of N-vinyl-pyrrolidones
    • 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
    • D06P3/791—Polyolefins using acid dyes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00—Applications
    • C08L2203/12—Applications used for fibers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L39/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
    • C08L39/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L39/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
    • C08L39/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
    • C08L39/08—Homopolymers or copolymers of vinyl-pyridine
    • 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
    • D01F6/44—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds
    • D01F6/46—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds of polyolefins
    • 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
    • Y10S8/09—Polyolefin
    • 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

  • a dye receptive stereoregular polyolefin composition is prepared by using about 2 to 20 percent polyethylene glycol of molecular weight from 100,000 to 5,000,000 meltdispersed in stereoregular polypropylene, polymethylpentens, or polymethylbutene.
  • the invention relates to stereoregular polyolefins. More particularly, this invention relates to polymeric compositions having improved afiinity for dyes, said com-positions containing a major amount of stereoregular polyolefins.
  • This invention relates to stereoregular polyolefins having increased affinity for dyes and other polar substances
  • a matrix of a stereoregular polyolefin taken from the group consisting of polypropylene, polymethylpentene and polymethylbutene said matrix of polyolefin having dispersed therein between about 2 and 20% of a modifying polymer which is hydrophilic, non-soluble in the polyolefin and fusible at a temperature not exceeding the temperature of processing of the polyolefin C. to 350 C.
  • said modifying polymer being selected from the group consisting of alkylene oxide polymers having molecular weights between 100,000 and 5,000,000,
  • poly N-vinyl pyrrolidone poly N-vinyl morpholine, and t v. poly N-vinyl oxazolidinone.
  • ethylene glycol resins of different molecular weight, was prepared and labeled as follows:
  • Each of the dried mixtures was prepared in the form of a disc in the following manner.
  • the powder of each sample was spread uniformly in a circular shouldered Pyrex glass dish with an inside diameter of 4 inches.
  • the dishes were then covered by an inner nesting circular shouldered Pyrex glass dish with a bottom outer separation rib projecting downwardly about 0.05 inch.
  • the assembly weighted with a preheated 5 pound weight was then placed in an oven at 250 C. for 6 to minutes. Then the Weight was removed and the assembly was placed in a refrigerator at about 4 C. to cool.
  • the assembly dishes were then separated to give a fused disc.
  • ASC-Cibalan Brilliant Scarlet RL a neutral dyeing metallized acid dye
  • Alkylene oxide polymers of 1000 to 10,000 molecular weight are considered suitable for use in plasticizing or improving the impact resistance of polypropylene. However, if these liquid or waxy substances plasticize polypropylene, they will adversely aifect the desirable properties in films and fibers. As shown, these relatively low molecular weight polyglycols have negligible effect on the dyeability of polypropylene. However, the polyalkylene oxides having molecular Weights of 100,000 to 4,00%- -000 can be used in relatively low percentages with negli gible eifect on desired physical properties to impart a greater degree of dyeability to the polypropylene as indicated by the results above.
  • Example 3 In accordance with the general procedure set forth in Example 1, I prepared two separate discs utilizing as modifiers poly N-vinyl oxazolidinone and poly N-vinyl morpholine. The dispersion of each of the homopolymers in each of their respective polypropylene discs was considered fair. Each disc exhibited only a slight increase in opacity over a control. The discs prepared with each of the modifiers was dyed in accordance with the procedure outlined in Example 1. I found that each disc was dyed to a light/ medium shade with DO disperse dyes heretofore described.
  • my modifiers with polyolefins are readily available. They may be combined during formation of the polymeric modifier or during actual polymerization of the polyolefin, with or without melting. They may be added to freshly polymerized polyolefin, which is still in solution in a suitable solvent, in the powdered form, or as a solution in a compatible solvent, or merely as a dispersion. They may be added to the polyolefin during precipitation, washing, neutralizing or compounding of the freshly prepared polyolefin prior to drying. This may be accomplished by adding the modifier as a powder or as a solution which is a non-solvent for the polyolefin.
  • the modifiers may also be melt mixed during processing or blending of the polymer prior to use in extension of fiber, film, coating or plastic. It may also be added as a liquid or powder to finely ground or micronized polyolefin polymers and then melt dispersed in situ during hot dip or spray coating or during spreading and heat coating operation. They may be incorporated in polyolefin solutions or emulsion and then applied to surfaces with or without heating.
  • the level of addition of the modifiers heretofore listed should be between 2 and 20% of the weight of the overall composition. If less than 2% is utilized, significant improvement will not be achieved in dyeability. If an amount greater than 20% is added to the polyolefin, many of the physical properties of the final product, such as fiber or film, are adversely affected. These include loss of strength and a lower resistance to repeated flexing.
  • Polyimines have high molecular mobility which apparently gives them some ease of solution in polyolefins. However, there is also a high tendency to sweat out and separate when the combination is made into fiber or film.
  • soluble polyvinylpyridines confer little or no dyeability on the polyolefin when dissolved therein. This appears to be the case until the preformed modified polyolefin is post treated with epoxy compounds, concentrated acids, alkylating agents, nitrous oxide gas, and alkylene oxides. However, such post treatments are diflicult, costly and generally impractical.
  • hydrophilic polymeric modifiers which may be soluble in either water or an oxygenated solvent but which are not soluble in the polyolefin.
  • modifiers which are fusible and can be dispersed in the'polyolefin.
  • My hydrophilic modifiers must be fusible with the polyolefin. This is necessary for the formation of a continuous network of modifier throughout the polyolefin in order to permit dye penetration and efficient coordination of the dye and modifier throughout the film or fibre.
  • a polymeric composition having improved aflinity for dyes consisting essentially of:
  • a matrix of stereoregular polyolefin taken from the group consisting of polypropylene, polymethylpentene, and polymethylbutene;
  • said matrix having melt-dispersed therein polyethylene glycol of a molecular weight from 100,000 to 5,000,- 000 in an amount between 2 and 20 percent by Weight of the combination of matrix plus polyethylene glycol as a continuous network throughout the matrix.

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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)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Coloring (AREA)
US400611A 1961-04-04 1964-09-30 Modification of stereoregular polyolefins with polyethylene glycol Expired - Lifetime US3366710A (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
NL276760D NL276760A (en)) 1961-04-04
BE616010D BE616010A (en)) 1961-04-04
FR892895A FR1321694A (fr) 1961-04-04 1962-03-30 Produits polyéthyléniques perfectionnés
GB12826/62A GB987421A (en) 1961-04-04 1962-04-03 Stereo regular polyolefins
LU41492A LU41492A1 (en)) 1961-04-04 1962-04-04
US400611A US3366710A (en) 1961-04-04 1964-09-30 Modification of stereoregular polyolefins with polyethylene glycol
US406939A US3375213A (en) 1961-04-04 1964-10-27 Modification of stereoregular polyolefins with synergistic polymeric combinations
US414919A US3316328A (en) 1961-04-04 1964-11-30 Stereoregular polyolefin compositions
US433226A US3497574A (en) 1961-04-04 1965-02-16 Adhesive compositions
US502719A US3425969A (en) 1961-04-04 1965-10-22 Process of preferentially modifying stereoregular polyhydrocarbons to improve dyeability
US502720A US3505429A (en) 1961-04-04 1965-10-22 Preferentially modified stereoregular polyhydrocarbons
US703784A US3484838A (en) 1961-04-04 1968-02-07 Modification of stereoregular polyolefin with hydrophilic copolymers

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US11397261A 1961-04-04 1961-04-04
US400611A US3366710A (en) 1961-04-04 1964-09-30 Modification of stereoregular polyolefins with polyethylene glycol
US406939A US3375213A (en) 1961-04-04 1964-10-27 Modification of stereoregular polyolefins with synergistic polymeric combinations
US414919A US3316328A (en) 1961-04-04 1964-11-30 Stereoregular polyolefin compositions

Publications (1)

Publication Number Publication Date
US3366710A true US3366710A (en) 1968-01-30

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Family Applications (3)

Application Number Title Priority Date Filing Date
US400611A Expired - Lifetime US3366710A (en) 1961-04-04 1964-09-30 Modification of stereoregular polyolefins with polyethylene glycol
US406939A Expired - Lifetime US3375213A (en) 1961-04-04 1964-10-27 Modification of stereoregular polyolefins with synergistic polymeric combinations
US414919A Expired - Lifetime US3316328A (en) 1961-04-04 1964-11-30 Stereoregular polyolefin compositions

Family Applications After (2)

Application Number Title Priority Date Filing Date
US406939A Expired - Lifetime US3375213A (en) 1961-04-04 1964-10-27 Modification of stereoregular polyolefins with synergistic polymeric combinations
US414919A Expired - Lifetime US3316328A (en) 1961-04-04 1964-11-30 Stereoregular polyolefin compositions

Country Status (5)

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US (3) US3366710A (en))
BE (1) BE616010A (en))
GB (1) GB987421A (en))
LU (1) LU41492A1 (en))
NL (1) NL276760A (en))

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3425981A (en) * 1965-02-12 1969-02-04 Union Carbide Corp Olefin polymer compositions containing ethylene oxide polymers having a molecular weight of from 100,000 to 10 million
US5288532A (en) * 1990-08-28 1994-02-22 Viskase Corporation Transferable modifier-containing film

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3408341A (en) * 1964-10-21 1968-10-29 Eastman Kodak Co Crystallinity promoters
US3449154A (en) * 1965-09-07 1969-06-10 Gaf Corp Poly-alpha-olefins coated with lactams or lactones and methods for producing same
US3479417A (en) * 1966-11-16 1969-11-18 Gaf Corp Graft copolymers of alpha-olefins and preformed,water-insoluble,homopolymer of n-vinyl-2-pyrrolidone
US3530201A (en) * 1966-12-06 1970-09-22 Uniroyal Inc Dyeable polyolefins containing thermoplastic nitrogen containing polymers and polyethylene oxide
US3622264A (en) * 1968-06-13 1971-11-23 Uniroyal Inc Fiber blends of polyolefin with polyvinylpyridines of quinolines with and without a polyethylene oxide and acid and disperse dye variegated dyeing thereof
US3652198A (en) * 1968-09-13 1972-03-28 Uniroyal Inc Mixture of filaments capable of being dyed to a multicolor pattern with anionic disperse dyes
US3914403A (en) * 1973-05-11 1975-10-21 Gaf Corp Hair care preparations containing N-vinyl pyrrolidone homo- and copolymers and a quaternized copolymer of vinyl pyrrolidone
DE2324922C3 (de) * 1973-05-17 1978-03-02 Ciba-Geigy Ag, Basel (Schweiz) Polyolefinformmassen mit erhöhter Verarbeitungsstabilität und mit verbesserter Farbe
US3971612A (en) * 1975-09-22 1976-07-27 Champion International Corporation Flip-top carton of trunk type for frozen ice cream and comestibles of similar consistency
US4133844A (en) * 1977-07-22 1979-01-09 E. I. Du Pont De Nemours And Company Product and process
US5169405A (en) * 1991-11-25 1992-12-08 Basf Corporation Multi-colored disperse dyeable fabric: polyester and poly-methyl-olefin blend
WO2013141033A1 (ja) * 2012-03-23 2013-09-26 東レ株式会社 ポリメチルペンテン複合繊維またはポリメチルペンテン多孔質繊維およびそれらからなる繊維構造体

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB814582A (en) * 1956-07-31 1959-06-10 Glanzstoff Ag A process for dyeing polyolefine textile materials
GB834160A (en) * 1957-04-10 1960-05-04 Gen Aniline & Film Corp Pigment composition
US3107228A (en) * 1956-12-12 1963-10-15 Montecatimi Societa Generale P Polypropylene containing a dye-receptive modifier which comprises polyal-kyleneimine or mixztures thereof with an epoxy resin
US3137989A (en) * 1959-02-18 1964-06-23 Montedison Spa Dyeable bulky yarns based on polypropylene
US3153680A (en) * 1959-08-03 1964-10-20 Montedison Spa Poly-alpha-olefin compositions having improved dye affinity
US3255275A (en) * 1961-01-30 1966-06-07 Dow Chemical Co Process for enhancing the dye-receptivity of continuous, coherent articles and products therefrom
US3303148A (en) * 1960-03-28 1967-02-07 Eastman Kodak Co High-density polypropylene blend with a cellulose ether or ester

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2628214A (en) * 1945-10-27 1953-02-10 Du Pont Curing of polyethylenes
US2527863A (en) * 1947-08-29 1950-10-31 Du Pont Modification and dyeing of acrylonitrile polymers
US2927904A (en) * 1956-11-19 1960-03-08 Phillips Petroleum Co Method of foaming blend of crystalline 1-olefin polymer and rubber and product obtained thereof
NL235375A (en)) * 1958-01-24
US3003845A (en) * 1958-04-01 1961-10-10 Dow Chemical Co Dye-receptive polymer compositions of fiber-forming polymers and crosslinked n-vinyl - 3 - morpholinone copolymers, preparation thereof and articles resulting therefrom
US3022267A (en) * 1958-05-14 1962-02-20 Sinclair Refining Co Stabilized isotactic polypropylene and method
US3069220A (en) * 1960-01-28 1962-12-18 Allied Chem Process for dyeing polyolefins
NL128493C (en)) * 1961-05-31

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB814582A (en) * 1956-07-31 1959-06-10 Glanzstoff Ag A process for dyeing polyolefine textile materials
US3107228A (en) * 1956-12-12 1963-10-15 Montecatimi Societa Generale P Polypropylene containing a dye-receptive modifier which comprises polyal-kyleneimine or mixztures thereof with an epoxy resin
GB834160A (en) * 1957-04-10 1960-05-04 Gen Aniline & Film Corp Pigment composition
US3137989A (en) * 1959-02-18 1964-06-23 Montedison Spa Dyeable bulky yarns based on polypropylene
US3153680A (en) * 1959-08-03 1964-10-20 Montedison Spa Poly-alpha-olefin compositions having improved dye affinity
US3303148A (en) * 1960-03-28 1967-02-07 Eastman Kodak Co High-density polypropylene blend with a cellulose ether or ester
US3255275A (en) * 1961-01-30 1966-06-07 Dow Chemical Co Process for enhancing the dye-receptivity of continuous, coherent articles and products therefrom

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3425981A (en) * 1965-02-12 1969-02-04 Union Carbide Corp Olefin polymer compositions containing ethylene oxide polymers having a molecular weight of from 100,000 to 10 million
US5288532A (en) * 1990-08-28 1994-02-22 Viskase Corporation Transferable modifier-containing film
US5374457A (en) * 1990-08-28 1994-12-20 Viskase Corporation Transferable modifier-containing film
US5382391A (en) * 1990-08-28 1995-01-17 Viskase Corporation Method for producing transferable modifier-containing film

Also Published As

Publication number Publication date
US3375213A (en) 1968-03-26
GB987421A (en) 1965-03-31
BE616010A (en)) 1900-01-01
NL276760A (en)) 1900-01-01
US3316328A (en) 1967-04-25
LU41492A1 (en)) 1962-06-04

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