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
- 238000004043 dyeing Methods 0.000 title claims description 11
- 229920000098 polyolefin Polymers 0.000 title claims description 6
- 239000000835 fiber Substances 0.000 title description 14
- 239000003054 catalyst Substances 0.000 title description 8
- 238000011282 treatment Methods 0.000 title description 7
- 230000004048 modification Effects 0.000 title description 3
- 238000012986 modification Methods 0.000 title description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title description 3
- 239000002243 precursor Substances 0.000 title description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 23
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 claims description 22
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 11
- 239000002657 fibrous material Substances 0.000 claims description 8
- 150000007529 inorganic bases Chemical class 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000001125 extrusion Methods 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- 229920013639 polyalphaolefin Polymers 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000000975 dye Substances 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- -1 nitrogen-containing compound Chemical class 0.000 description 7
- 239000004743 Polypropylene Substances 0.000 description 6
- 239000003086 colorant Substances 0.000 description 6
- 229920001155 polypropylene Polymers 0.000 description 6
- 238000000605 extraction Methods 0.000 description 5
- 238000002074 melt spinning Methods 0.000 description 5
- 230000000707 stereoselective effect Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000980 acid dye Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 229940093476 ethylene glycol Drugs 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- ZHFPEICFUVWJIS-UHFFFAOYSA-M sodium 2-hydroxy-5-[(3-nitrophenyl)diazenyl]benzoate Chemical compound [Na+].Oc1ccc(cc1C([O-])=O)N=Nc1cccc(c1)[N+]([O-])=O ZHFPEICFUVWJIS-UHFFFAOYSA-M 0.000 description 2
- CKMPIIPZKJISCU-UHFFFAOYSA-M sodium;4,8-diamino-1,5-dihydroxy-9,10-dioxoanthracene-2-sulfonate Chemical compound [Na+].O=C1C2=C(N)C=C(S([O-])(=O)=O)C(O)=C2C(=O)C2=C1C(O)=CC=C2N CKMPIIPZKJISCU-UHFFFAOYSA-M 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- NLXFWUZKOOWWFD-UHFFFAOYSA-N 1-(2-hydroxyethylamino)-4-(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NCCO)=CC=C2NC NLXFWUZKOOWWFD-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- JKYKXTRKURYNGW-UHFFFAOYSA-N 3,4-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C(O)C(S(O)(=O)=O)=C2 JKYKXTRKURYNGW-UHFFFAOYSA-N 0.000 description 1
- AOMZHDJXSYHPKS-DROYEMJCSA-L Amido Black 10B Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC2=CC(S([O-])(=O)=O)=C(\N=N\C=3C=CC=CC=3)C(O)=C2C(N)=C1\N=N\C1=CC=C(N(=O)=O)C=C1 AOMZHDJXSYHPKS-DROYEMJCSA-L 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- WZNOVKIUXSHKBP-UHFFFAOYSA-N N1CCNCC1.C(Cl)C1CO1.C(CCCCCCCCCCCCCCCCC)N Chemical compound N1CCNCC1.C(Cl)C1CO1.C(CCCCCCCCCCCCCCCCC)N WZNOVKIUXSHKBP-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000003945 chlorohydrins Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- DMYYMROEUDSFIN-UHFFFAOYSA-L disodium 3-hydroxy-4-[[2-methyl-4-[(2-methylphenyl)diazenyl]phenyl]diazenyl]naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].Cc1ccccc1N=Nc1ccc(N=Nc2c(O)c(cc3cc(ccc23)S([O-])(=O)=O)S([O-])(=O)=O)c(C)c1 DMYYMROEUDSFIN-UHFFFAOYSA-L 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920002717 polyvinylpyridine Polymers 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
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 (en)) |
| BE (1) | BE618943A (en)) |
| CH (2) | CH373555A (en)) |
| DE (1) | DE1444092A1 (en)) |
| ES (1) | ES278319A1 (en)) |
| FI (1) | FI40024B (en)) |
| GB (1) | GB982953A (en)) |
| NL (2) | NL279375A (en)) |
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 NL130157D patent/NL130157C/xx active
- BE BE618943D patent/BE618943A/xx unknown
- NL NL279375D patent/NL279375A/xx unknown
-
1962
- 1962-06-12 US US201818A patent/US3281203A/en not_active Expired - Lifetime
- 1962-06-12 GB GB22552/62A patent/GB982953A/en not_active Expired
- 1962-06-13 FI FI1156/62A patent/FI40024B/fi active
- 1962-06-14 DE DE19621444092 patent/DE1444092A1/de not_active Withdrawn
- 1962-06-14 CH CH1451062A patent/CH373555A/de unknown
- 1962-06-14 ES ES278319A patent/ES278319A1/es not_active Expired
- 1962-06-14 CH CH715862A patent/CH379464A/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 |
|---|---|
| CH379464A (de) | 1964-08-31 |
| GB982953A (en) | 1965-02-10 |
| ES278319A1 (es) | 1963-01-16 |
| CH373555A (de) | 1963-11-30 |
| NL130157C (en)) | |
| DE1444092A1 (de) | 1968-11-07 |
| BE618943A (en)) | |
| CH715862A4 (en)) | 1964-03-31 |
| NL279375A (en)) | |
| FI40024B (en)) | 1968-05-31 |
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