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 PDFInfo
- Publication number
- 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
- Authority
- US
- United States
- Prior art keywords
- dichlorohydrin
- treatment
- modification
- basic nitrogen
- dyeing characteristics
- 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
-
- 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.
Landscapes
- 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)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT1105661 | 1961-06-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3281203A true US3281203A (en) | 1966-10-25 |
Family
ID=11134725
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US201818A Expired - Lifetime US3281203A (en) | 1961-06-15 | 1962-06-12 | Modification of the dyeing characteristics of isotactic polyolefin fibers containing basic nitrogen groups through treatment with a diepoxide precursor and an alkaline catalyst |
Country Status (8)
Country | Link |
---|---|
US (1) | US3281203A (de) |
BE (1) | BE618943A (de) |
CH (2) | CH379464A (de) |
DE (1) | DE1444092A1 (de) |
ES (1) | ES278319A1 (de) |
FI (1) | FI40024B (de) |
GB (1) | GB982953A (de) |
NL (2) | NL130157C (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106436376A (zh) * | 2016-09-19 | 2017-02-22 | 江苏工程职业技术学院 | 一种涤棉织物同浴染色匀染剂的制备方法 |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 | |
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 |
-
0
- NL NL279375D patent/NL279375A/xx unknown
- BE BE618943D patent/BE618943A/xx unknown
- NL NL130157D patent/NL130157C/xx active
-
1962
- 1962-06-12 GB GB22552/62A patent/GB982953A/en not_active Expired
- 1962-06-12 US US201818A patent/US3281203A/en not_active Expired - Lifetime
- 1962-06-13 FI FI1156/62A patent/FI40024B/fi active
- 1962-06-14 CH CH715862A patent/CH379464A/de unknown
- 1962-06-14 DE DE19621444092 patent/DE1444092A1/de not_active Withdrawn
- 1962-06-14 ES ES278319A patent/ES278319A1/es not_active Expired
- 1962-06-14 CH CH1451062A patent/CH373555A/de unknown
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106436376A (zh) * | 2016-09-19 | 2017-02-22 | 江苏工程职业技术学院 | 一种涤棉织物同浴染色匀染剂的制备方法 |
CN106436376B (zh) * | 2016-09-19 | 2019-03-19 | 江苏工程职业技术学院 | 一种涤棉织物同浴染色匀染剂的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
FI40024B (de) | 1968-05-31 |
NL279375A (de) | |
BE618943A (de) | |
CH715862A4 (de) | 1964-03-31 |
NL130157C (de) | |
CH379464A (de) | 1964-08-31 |
ES278319A1 (es) | 1963-01-16 |
DE1444092A1 (de) | 1968-11-07 |
CH373555A (de) | 1963-11-30 |
GB982953A (en) | 1965-02-10 |
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