US3366710A - Modification of stereoregular polyolefins with polyethylene glycol - Google Patents
Modification of stereoregular polyolefins with polyethylene glycol Download PDFInfo
- 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
- Authority
- US
- United States
- Prior art keywords
- polyolefin
- modifiers
- stereoregular
- polyethylene glycol
- modifier
- Prior art date
- 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
Links
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.
Landscapes
- 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)
Priority Applications (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE616010D BE616010A (US07714131-20100511-C00038.png) | 1961-04-04 | ||
NL276760D NL276760A (US07714131-20100511-C00038.png) | 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 (US07714131-20100511-C00038.png) | 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 |
Family
ID=27493936
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)
Cited By (2)
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)
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)
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)
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 (US07714131-20100511-C00038.png) * | 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 (US07714131-20100511-C00038.png) * | 1961-05-31 |
-
0
- BE BE616010D patent/BE616010A/xx unknown
- NL NL276760D patent/NL276760A/xx unknown
-
1962
- 1962-04-03 GB GB12826/62A patent/GB987421A/en not_active Expired
- 1962-04-04 LU LU41492A patent/LU41492A1/xx unknown
-
1964
- 1964-09-30 US US400611A patent/US3366710A/en not_active Expired - Lifetime
- 1964-10-27 US US406939A patent/US3375213A/en not_active Expired - Lifetime
- 1964-11-30 US US414919A patent/US3316328A/en not_active Expired - Lifetime
Patent Citations (7)
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)
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 |
---|---|
BE616010A (US07714131-20100511-C00038.png) | 1900-01-01 |
GB987421A (en) | 1965-03-31 |
US3316328A (en) | 1967-04-25 |
LU41492A1 (US07714131-20100511-C00038.png) | 1962-06-04 |
NL276760A (US07714131-20100511-C00038.png) | 1900-01-01 |
US3375213A (en) | 1968-03-26 |
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