US3281203A - Modification of the dyeing characteristics of isotactic polyolefin fibers containing basic nitrogen groups through treatment with a diepoxide precursor and an alkaline catalyst - Google Patents

Modification of the dyeing characteristics of isotactic polyolefin fibers containing basic nitrogen groups through treatment with a diepoxide precursor and an alkaline catalyst Download PDF

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US3281203A
US3281203A US201818A US20181862A US3281203A US 3281203 A US3281203 A US 3281203A US 201818 A US201818 A US 201818A US 20181862 A US20181862 A US 20181862A US 3281203 A US3281203 A US 3281203A
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dichlorohydrin
treatment
modification
basic nitrogen
dyeing characteristics
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Riboni Ubaldo
Bartolucci Luigi
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Montedison SpA
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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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/11—Compounds containing epoxy groups or precursors thereof
    • 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
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/651—Compounds without nitrogen
    • D06P1/65106—Oxygen-containing compounds
    • 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
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/651—Compounds without nitrogen
    • D06P1/65106—Oxygen-containing compounds
    • D06P1/65118—Compounds containing hydroxyl groups
    • 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
    • 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
    • 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
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/22—Effecting variation of dye affinity on textile material by chemical means that react with the fibre
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/928—Polyolefin fiber

Definitions

  • the invention also encompasses'the improved products obtained from this process.
  • dichlorohydrins are employed in aqueous solutions dissolved in organic solvents such as aliphatic, aromatic hydrocarbons, etc., or in the anhydrous state.
  • the alkaline agent is added directly to the vessel or apparatus wherein the treatment of the fibers is carried out, either immediately before or after the introduction of fibers into the vessel.
  • the treatment of the yarns is performed before and/or after their stretching, for times which may vary from a few (at least 30) seconds to 2-3 hours, and at temperatures varying from room temperature to 10' below the melting point of the polymer.
  • the alkaline agent e.g. sodium hydroxide
  • Dichlorohydrin may be employed either in the pure form or while containing the normal impurities.
  • (LH II 1 is prepared by introducing 64 g. (1 mole) of ethyleneglycol and 0.4 cc. of boron trifiuoride in 45% ethereal solution into a three-necked 500-cc. flask, provided with thermometer, stirrer and reflux condenser. The mass is warmed up to C. and 185 g. epichlorohydrin are added within two hours. The mass is kept in reaction for one additional hour, and then is cooled to room temperature.
  • the diehlorohydrin thus obtained which has a titer of about 72%, is ready for use.
  • the treated yarn is dyed with the fol-lowing dyes:
  • Alizarine yellow 2 G (C.l. #14025) (C.l. mordant yellow 1) (acid) Red for wool B (C.l. #27200) (C.l. acid red 115) (acid) Alizarine red S (C.l. #58005) (C.l. mordant red 3) (acid) Alizarine blue SE (C.l. #63000) (C.l. acid blue 43) (acid) Acid black .lVS (C.l. #20470) (C.l. acid black 1) (acid) Setacyl bright blue BG (C.l. #61505) (C.l. disperse blue 3) (plastosol)
  • the dyeings are carried out by maintaining the yarn in the bath containing 2.5% dye, based on the weight of fiber, at a fiber/bath ratio of I:40.
  • the dyeings with acid dyes are carried out in the presence of 3% ammonium acetate (based on the weight of fiber) and 1% of a surfactant prepared by the condensation of ethylene oxide with p.cresol. 30 minutes after the boiling commences, 2%, based on the weight of fiber, of a 10% acetic acid solution is added in order to improve the rate of utilization of the bath.
  • Dyeings with plastosoluble (dispersed) dyes are carried out in the presence of 2% (based on the fiber weight) of a surfactant.
  • the yarns, after dyeing, are rinsed with running water and are intensely dyed, either with the acid or plastosoluble dyes. The light, washing and friction fastness'of these dyed yarns is shown to be entirely satisfactory.
  • Example 2 1 Here and In the following examples the lntrlnsle viscosity has been measured in tetralin at C.
  • the ture is 30 C.
  • the yarn is allowed to remain in the e oxidation bath for 2 minutes.
  • the roving is allowed to pass between rolls so that 2% of the pure opoxide is allowed to remain on the yarn.
  • the collected roving is treated in an autoclave with steam at 120 C. for 1 hour.
  • the yarn upon being dyed with the dyes of Example 1, gives intense, fast colors.
  • Example 4 sodium hydroxide is added as in Example 4. The mass is then treated in hot air at 130' C. for 20 minutes, washed with water and dried. The treated yarn yields intense and fast colors upon being dyed with the dyes of Example 1.
  • Example 7 2000 cc. of monochioroglyccrol and 5 cc. of a 45% ether solution of boron triiiuorlde are poured into a 3- liter, three-necked flask, provided with reflux condenser, thermometer and tap funnel. The mixture is heated at 95-400 C. and 610 cc. of epichiorohydrin are added over a period of about two hours so as to keep the temperature constant. When these additions are completed, the fiaslt is kept at 95-100 C. for two additional hours and the excess monochloroglyccrol is distilled off under vacuum.
  • a process for improving the dyeing characteristics of fibrous materials such as filaments and yarns obtained by the extrusion of mixes of a polyaipha-olefin exhibiting a high content of crystallinity due to isotactic structure and 1-25%, based on the weight of said poiyolcfin, of a polymeric basic-nitrogen containing compound which process comprises contacting the fibrous materials in a bath with a glycol dichlorohydrin and a stoichiometric amount of a strong inorganic base to convert said dichlorohydrin into dicpoxide, at temperatures between room temperature and 10' C. below the softening point of the polymer, for a time varying from 30 seconds to 3 hours.
  • polymeric basicnitrogen containing compound is selected from the group consisting of octadecylamine-epichlorohydrin-piperazine condensates, octndccyiaminc-epichlorohydrin-hexamethylenediamine condensates, isotactic crystalline polyvinyl pyridines and dihalogen derivative-diamine condensates.
  • glycol dichlorohydrin is the dichlorohydrin of diglycidylether.
  • glycol diehlorohydrin is the dichlorohydrin of the ethyieneglyeol diglycidyiether.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Artificial Filaments (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

United States Patent 3,281,203 MODIFICATION OF THE DYEING CHARACTER- ISTICS 0F ISOTACTIC POLYOLEFIN FIBERS CONTAINING B A S I C NITROGEN GROUPS THROUGH TREATMENT WITH A DIEPOXIDE PRECURSOR AND AN ALKALINE CATALYST Uhaldo Riboni, Milan, and Luigi Bartolucci, Temi, Italy, assignors to Montecatinl Soeieta Generale per llndustria Minerarla e Chimiea, Milan, Italy, a corporation of Italy No Drawing. Filed June 12, 1962, Ser. No. 201,818 Claims priority, application Italy, June 15, 1961, 11,056 16 Claims. (Cl. 8-1155) The present invention relates to a process for improving the dyeing characteristics of textile fibers obtained by the extrusion of mixes containing:
(A) polyolefin prepared with stereo-specific catalysts, and
exhibiting a high content of crystallinity due to the isotactic structure.
(B) a basic nitrogen-containing compound.
The invention also encompasses'the improved products obtained from this process.
Processes for improving the dye receptivity of textile fibers to different classes of dyes, especially to acid dyes. by the extrusion of mixtures containing crystalline polyolefins with 1-25% by weight based on the polyolefin, of polymeric basic nitrogen-containing products, have been described in commonly assigned United States applications.
Methods have also'becn described, in commonly assigned applications, for further improving the dyeing characteristics, particularly the 'fastness of the thus obtained polyolefinic fibers, by means of treatments with diepoxidie compounds, particularly with aqueous solutions of ethyleneglyool digiycidyl ether or diglycidyl ether.
We have now surprisingly found that remarkably better results are obtained when the fibers obtained from the mixes mentioned above are treated with chlorohydrins and alkaline agents such as sodium hydroxide or potassium hydroxide and the like, which form the corresponding diepoxidic compounds at the moment of use or, even more desirably, to operate so that the diepoxide formation occurs directly on the fiber.
The dichlorohydrins are employed in aqueous solutions dissolved in organic solvents such as aliphatic, aromatic hydrocarbons, etc., or in the anhydrous state.
The alkaline agent is added directly to the vessel or apparatus wherein the treatment of the fibers is carried out, either immediately before or after the introduction of fibers into the vessel.
The treatment of the yarns is performed before and/or after their stretching, for times which may vary from a few (at least 30) seconds to 2-3 hours, and at temperatures varying from room temperature to 10' below the melting point of the polymer. The alkaline agent, e.g. sodium hydroxide, is added to the solution of diehlorohydrin in the amount stoichiometrically needed for conversion to the diepoxide. Dichlorohydrin may be employed either in the pure form or while containing the normal impurities.
The following examples are given to better illustrate the present invention without limiting its scope.
All .parts and proportions are by weight unless otherwise indicated.
"ice
in (LH II 1 is prepared by introducing 64 g. (1 mole) of ethyleneglycol and 0.4 cc. of boron trifiuoride in 45% ethereal solution into a three-necked 500-cc. flask, provided with thermometer, stirrer and reflux condenser. The mass is warmed up to C. and 185 g. epichlorohydrin are added within two hours. The mass is kept in reaction for one additional hour, and then is cooled to room temperature.
The diehlorohydrin thus obtained, which has a titer of about 72%, is ready for use.
A yarn obtained by the melt spinning of a mix comprising of polypropylene prepared with stereospecific catalysts ([n] =l.5l, ash content=0.028%, residue to heptane extraction=95.6%) and 5% of octadecy-lamine/ epichlorohydrin/piperazine condensate, is immersed for 5 minutes at 25' C. in a 5% aqueous solution of the dichlorohydrin of ethyleneglycol diglycidylether, to which 13 g. of NaOH per liter of solution have been added immediately before. After a treatment with squeezing rolls, about 70% of the solution remains on the yarn. The yarn is then subjected to a thermal treatment at C. for 20 minutes.
The treated yarn is dyed with the fol-lowing dyes:
Alizarine yellow 2 G (C.l. #14025) (C.l. mordant yellow 1) (acid) Red for wool B (C.l. #27200) (C.l. acid red 115) (acid) Alizarine red S (C.l. #58005) (C.l. mordant red 3) (acid) Alizarine blue SE (C.l. #63000) (C.l. acid blue 43) (acid) Acid black .lVS (C.l. #20470) (C.l. acid black 1) (acid) Setacyl bright blue BG (C.l. #61505) (C.l. disperse blue 3) (plastosol) The dyeings are carried out by maintaining the yarn in the bath containing 2.5% dye, based on the weight of fiber, at a fiber/bath ratio of I:40.
The dyeings with acid dyes are carried out in the presence of 3% ammonium acetate (based on the weight of fiber) and 1% of a surfactant prepared by the condensation of ethylene oxide with p.cresol. 30 minutes after the boiling commences, 2%, based on the weight of fiber, of a 10% acetic acid solution is added in order to improve the rate of utilization of the bath.
Dyeings with plastosoluble (dispersed) dyes are carried out in the presence of 2% (based on the fiber weight) of a surfactant. The yarns, after dyeing, are rinsed with running water and are intensely dyed, either with the acid or plastosoluble dyes. The light, washing and friction fastness'of these dyed yarns is shown to be entirely satisfactory.
Example 2 1 Here and In the following examples the lntrlnsle viscosity has been measured in tetralin at C.
ture is 30 C. The yarn is allowed to remain in the e oxidation bath for 2 minutes. The roving is allowed to pass between rolls so that 2% of the pure opoxide is allowed to remain on the yarn. The collected roving is treated in an autoclave with steam at 120 C. for 1 hour. The yarn, upon being dyed with the dyes of Example 1, gives intense, fast colors.
Example 3 A yarn obtained by the melt spinning of a mix containing 95% polypropylene prepared with stereospecific catalysts (l l)=l.5l, ash contcnt=0.028%, heptanc extraction rcsiduc=95.6%) and of an octndecyi-nmine/epichlorohydrin/pipcrazinc condensate is immersed for 5 minutes at 40 C. in a 6% aqueous solution of the dichlorohydrin of ethyleneglycol diglycidylether. An amount of sodium hydroxide corresponding to 80% of the theoretical amount based on the dichlorohydrin is then added. The mass is finally centrifuged, treated with warm water and dried. The treated yarn gives intense, fast colors upon being dyed with the dyes of Example 1.
Example 4 A yarn obtained through the melt spinning of a mix eontaining 95% of polypropylene prepared with stereospeeific catalysts ([v7] )=l.5l, ash oontent=0.028%. heptane extraction residue=95.6%) and 5% of dichloroethane/hexamethylenedinmine condensate is immersed for minutes. at 20' C.. in a 3% aqueous solution of the dichlorohydrin of ethylcnegiycol diglycidylether. Then an amount equivalent to the sodium hydroxide used in Example 3 is added. The mass is centrifuged, heated in autoclave at 120' C. for one hour and then washed with water and dried. The treated yarn gives intense. fast colors upon being dyed with the dyes of Example 1.
Example 5 A yarn obtained by the melt spinning of a mix containing 95% of polypropylene prepared with stereospecific catalysts ([r7]=l.5l, ash content=0.028%, heptanc extraction residue=95.6%) and 5% of octadecylamine/ cpichlorohydrinlhcxamethylencdiamine condensate is immersed for 30 minutes at 60 C. in a 3% aqueous solution of the dichlorohydrin of ethyleneglycol digiycidylether.
Then sodium hydroxide is added as in Example 4. The mass is then treated in hot air at 130' C. for 20 minutes, washed with water and dried. The treated yarn yields intense and fast colors upon being dyed with the dyes of Example 1.
Example 6 A yarn obtained by the melt spinning of a mix containing 95% of polypropylene prepared with stereo specific catalysts ]==l.5l, ash contcnt=0.028%, hcptanc extraction residue=95.6%) and 5% of isotactic crystalline poly-2-vinylpyridine ([v;]=0.22 is immersed for 40 minutes at 40' C. in a 10% aqueous solution of the diehlorohydrin of ethyleneglycol digiycidyicther.
Then stoichiometrically equivalent amounts of sodium hydroxide are added. The mass is centrifuged, treated in hot air at 130' C. for 30 minutes, washed with water and dried. The treated yarn gives intense, fast colors upon being dyed with the dyes of Example 1.
Example 7 2000 cc. of monochioroglyccrol and 5 cc. of a 45% ether solution of boron triiiuorlde are poured into a 3- liter, three-necked flask, provided with reflux condenser, thermometer and tap funnel. The mixture is heated at 95-400 C. and 610 cc. of epichiorohydrin are added over a period of about two hours so as to keep the temperature constant. When these additions are completed, the fiaslt is kept at 95-100 C. for two additional hours and the excess monochloroglyccrol is distilled off under vacuum.
Then the dichlorohydrin of the formula:
is collected at ISO-165 C. under 3 mm. pressure. The yield of pure dichlorohydrin is higher than A 40% aqueous solution of this dichlorohydrin is prepared and treated with an amount of NaOH solution equivalent to the theoretical amount required. A roving of the yarn obtained following the procedure of Example I is passed into this solution immediately. After a squeezing between rolls so as to leave on the yarn about 2% pure diglycidylcther, the yarn is treated with a stream of hot air at C. for 15 minutes. The colors obtained upon dyeing these yarns with the acid dyes of Example I, after the epoxidic treatment, are fast and bright.
Many variations and modifications can, of course, be practiced without departing from the spirit and scope of the present invention.
Having thus described the invention, what it is desired to secure and claim by Letters Patent is:
1. A process for improving the dyeing characteristics of fibrous materials such as filaments and yarns obtained by the extrusion of mixes of a polyaipha-olefin exhibiting a high content of crystallinity due to isotactic structure and 1-25%, based on the weight of said poiyolcfin, of a polymeric basic-nitrogen containing compound, which process comprises contacting the fibrous materials in a bath with a glycol dichlorohydrin and a stoichiometric amount of a strong inorganic base to convert said dichlorohydrin into dicpoxide, at temperatures between room temperature and 10' C. below the softening point of the polymer, for a time varying from 30 seconds to 3 hours.
2. The process of claim 1 wherein the fibrous materials are successively contacted in said bath with the glycol dichlorohydrin and the strong inorganic base.
3. The process of claim 1 wherein the fibrous materials are simultaneously contacted in said bath with the glycol dichlorohydrin and the strong inorganic base.
4. The process of claim 1 wherein the polymer exhibiting a high content of crystallinity due to isotactic structure is polypropylene.
5. The process of claim I wherein the polymeric basicnitrogen containing compound is selected from the group consisting of octadecylamine-epichlorohydrin-piperazine condensates, octndccyiaminc-epichlorohydrin-hexamethylenediamine condensates, isotactic crystalline polyvinyl pyridines and dihalogen derivative-diamine condensates.
6. The process of claim 1 wherein the glycol dichlorohydrin is the dichlorohydrin of diglycidylether.
7. The process of claim 1 wherein the glycol diehlorohydrin is the dichlorohydrin of the ethyieneglyeol diglycidyiether.
8. The process of claim 1 wherein the strong inorganic base is sodium hydroxide.
. 9. The process of claim 1 wherein the glycol dichlorohydrin is in the anhydrous state.
10. The process of claim 1 wherein the glycol dichlorohydrin is in aqueous solution. A
11. The process of claim 1 wherein the glycol dichlorohydrin is dissolved in an organic solvent.
12. The process of claim 1 wherein the fibrous materials are contacted with the glycol dichlorohydrin and the stroniinorganic base before stretching thereof.
13. The process of claim 1 wherein the fibrous materials are contacted with the glycol diehlorohydrin and the strong inorganic base after stretching thereof.
14. The process of claim 1 when carried out in a batchwisc manner.
15. The process of claim 1 when carried out in a continuous manner.
References Cited by the Examiner UNITED STATES PATENTS 2,730,427 1/1956 Suen 8-116 2,903,381 9/1959 Schroeder 8116 X 2,985,501 5/1961 6 Goldann 8115.5 Battaglioli. Cappuccio et a1. 855 X Cappuccio et a1 8-55 X Cappuccio et a1 8-1155 Monaci et a1. 8-115.5
NORMAN G. TORCHIN, Primary Examiner.
JULIAN S. LEVITT, Examiner.
Gagarine S120 10 I. CANNON, Assistant Examiner.

Claims (1)

1. A PROCESS FOR IMPROVING THE DYEING CHARACTERISTICS OF FIBROUS MATERIALS SUCH AS FILAMENTS AND YARNS OBTAINED BY THE EXTRUSION OF MIXES OF A POLYALPHA-OLEFIN EXHIBTING A HIGH CONTENT OF CRYSTALLINITY DUE TO ISOTACTIC STRUCTURE AND 1-25%, BASED ON THE WEIGHT OF SAID POLYOLEFINE, OF A POLYMERIC BASIC-NITROGEN CONTAINING COMPOUND, WHICH PROCESS COMPRISES CONTACTING THE FIBROUS MATERIALS IN A BATH WITH A GLYCOL DICHLOROHYDRIN AND A STOICHIOMETRIC AMOUNT OF A STRONG INORGANIC BASE TO CONVERT SAID DICHLOROHYDRIN INTO DIEPOXIDE, AT TEMPERATURES BETWEEN ROOM TEMPERATURE AND 10* C. BELOW THE SOFTENING POINT OF THE POLYMER, FOR A TIME VARYING FROM 30 SECONDS TO 3 HOURS.
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CN106436376A (en) * 2016-09-19 2017-02-22 江苏工程职业技术学院 Preparation method of leveling agent for one-bath dyeing of polyester-cotton fabric

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US3013998A (en) * 1956-09-27 1961-12-19 Montedison Spa Dyeable compositions, articles formed therefrom and methods for making said articles
US3098697A (en) * 1956-12-12 1963-07-23 Dichloroethane
US3151928A (en) * 1960-05-05 1964-10-06 Montedison Spa Process for improving the tinctorial characteristics of polyolefin fibres
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US2730427A (en) * 1952-08-13 1956-01-10 American Cyanamid Co Shrinkage control of cellulosic and wool textiles with diglycidyl ether compounds
US2903381A (en) * 1954-09-03 1959-09-08 Shell Dev Treatment of synthetic textiles with a polyepoxide having a plurality of 1,2 epoxy groups
US2985501A (en) * 1956-04-03 1961-05-23 Deering Milliken Res Corp Process of producing flat drying, wet crease resistant cellulosic fabrics by reaction with cross-linking agents and products produced thereby
US2998295A (en) * 1956-08-08 1961-08-29 Bohme Fettchemie Gmbh Process for the improvement of shaped thermoplastic materials containing carbonamidegroups
US3013998A (en) * 1956-09-27 1961-12-19 Montedison Spa Dyeable compositions, articles formed therefrom and methods for making said articles
US3098697A (en) * 1956-12-12 1963-07-23 Dichloroethane
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
US3151928A (en) * 1960-05-05 1964-10-06 Montedison Spa Process for improving the tinctorial characteristics of polyolefin fibres
US3223472A (en) * 1960-12-15 1965-12-14 Montedison Spa Process for improving the tinctorial characteristics of fibers obtained from olefin polymers

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106436376A (en) * 2016-09-19 2017-02-22 江苏工程职业技术学院 Preparation method of leveling agent for one-bath dyeing of polyester-cotton fabric
CN106436376B (en) * 2016-09-19 2019-03-19 江苏工程职业技术学院 A kind of preparation method of polyester-cotton fabric co-bathing dyeing levelling agent

Also Published As

Publication number Publication date
FI40024B (en) 1968-05-31
NL279375A (en)
BE618943A (en)
CH715862A4 (en) 1964-03-31
NL130157C (en)
CH379464A (en) 1964-08-31
ES278319A1 (en) 1963-01-16
DE1444092A1 (en) 1968-11-07
CH373555A (en) 1963-11-30
GB982953A (en) 1965-02-10

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