EP1025293B1 - Verfahren zur herstellung von aus wässriger färbeflotte färbbaren modifizierten polypropylengarnen sowie deren verwendung - Google Patents
Verfahren zur herstellung von aus wässriger färbeflotte färbbaren modifizierten polypropylengarnen sowie deren verwendung Download PDFInfo
- Publication number
- EP1025293B1 EP1025293B1 EP98958229A EP98958229A EP1025293B1 EP 1025293 B1 EP1025293 B1 EP 1025293B1 EP 98958229 A EP98958229 A EP 98958229A EP 98958229 A EP98958229 A EP 98958229A EP 1025293 B1 EP1025293 B1 EP 1025293B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- polypropylene
- carboxylic acid
- employed
- approximately
- weight
- 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
- -1 polypropylene Polymers 0.000 title claims abstract description 58
- 239000004743 Polypropylene Substances 0.000 title claims abstract description 55
- 229920001155 polypropylene Polymers 0.000 title claims abstract description 55
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 42
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 14
- 239000004744 fabric Substances 0.000 claims abstract description 13
- 239000000835 fiber Substances 0.000 claims abstract description 9
- 239000004753 textile Substances 0.000 claims abstract description 9
- 238000001125 extrusion Methods 0.000 claims abstract description 7
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 5
- 239000000975 dye Substances 0.000 claims description 28
- 239000000654 additive Substances 0.000 claims description 17
- 238000004043 dyeing Methods 0.000 claims description 17
- 230000000996 additive effect Effects 0.000 claims description 15
- 238000009987 spinning Methods 0.000 claims description 8
- 239000004594 Masterbatch (MB) Substances 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 5
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 230000003068 static effect Effects 0.000 claims description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 claims 2
- 230000008569 process Effects 0.000 abstract description 16
- 238000010035 extrusion spinning Methods 0.000 abstract description 7
- 239000003086 colorant Substances 0.000 abstract description 2
- 150000001735 carboxylic acids Chemical class 0.000 abstract 2
- 239000008187 granular material Substances 0.000 description 8
- 239000000155 melt Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 238000012545 processing Methods 0.000 description 5
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000008202 granule composition Substances 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000006069 physical mixture Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- JFINOWIINSTUNY-UHFFFAOYSA-N pyrrolidin-3-ylmethanesulfonamide Chemical compound NS(=O)(=O)CC1CCNC1 JFINOWIINSTUNY-UHFFFAOYSA-N 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- NOSXUFXBUISMPR-UHFFFAOYSA-N 1-tert-butylperoxyhexane Chemical compound CCCCCCOOC(C)(C)C NOSXUFXBUISMPR-UHFFFAOYSA-N 0.000 description 1
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000008275 binding mechanism Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000434 metal complex dye Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
Classifications
-
- 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
- D06P3/792—Polyolefins using basic dyes
-
- 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
- D01F6/28—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D01F6/30—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds comprising olefins as the major constituent
-
- 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
- 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
- D06P3/794—Polyolefins using dispersed 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
- 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
- D06P3/798—Polyolefins using reactive 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
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/40—Knit fabric [i.e., knit strand or strip material]
Definitions
- the invention relates to a process for the preparation of dyeable from aqueous dye liquor modified polypropylene yarns, the polypropylene yarn obtained by this process and the use of polypropylene yarns for the production of textile fabrics.
- the invention also relates to a process for dyeing the polypropylene yarns or textile fabrics.
- the yarns are spin-dyed by using an extrusion process colored masterbatch granulate, made from a type of polypropylene suitable for fiber formation and a suitable color pigment.
- US-A-3 112 159 is a method for better staining provided by polyolefin fibers.
- a polyolefin mixed with a dicarboxylic acid compound and then spun the mixture.
- the fibers can then be subjected to amination. additionally solid dispersants can be added to this mixture. This will in the extrusion spinning plant only a physical mixture of polyolefin and receive a dye-binding additive and this while maintaining the mixing state processed into filament yarn.
- the present Invention the object of a process for the production of modified polypropylene yarns to provide that by a standard pull-out procedure aqueous dye liquor can be dyed with great depths of color.
- This coloring is supposed to commercially available dyes achieved using conventional dye concentrations become.
- the process should continue to have as few process steps as possible, which leads to cost savings and also be ecologically harmless.
- this object is achieved by a method which is characterized in that is that CR polypropylene suitable for fiber formation with a reactant, which can react with the CR polypropylene, mixed and the mixture obtained in one Extrusion spinning machine is processed into yarn.
- the controlled flow behavior can be different Ways to be achieved, for example by mechanical-thermal stress, ⁇ -radiation, oxidation or by adding peroxides.
- the process consists of processing the powdery polymer during processing or Processing process to add organic peroxides. Free radicals form in the heat, which are preferably hydrogen from the statistically predominant longest chains of hydrogen split off, lead to chain splitting via subsequent reactions and thus a closer one Molecular weight distribution cause, which increases the melt index.
- the easy flowing CR polypropylene thus contains, like any other thermally oxidatively stressed polypropylene type, Hydroxyl groups. These are inevitable in the polypropylene types mentioned generated end or page groups.
- the melt index MFR (melt flow rate, at 2.16 kg / 10 min) of the CR polypropylene used is in the range from about 10 to 1200.
- the melt index is preferably in Range of about 15 to 300.
- a range of about 20 to 120 das is particularly preferred
- the molecular weight of the CR polypropylene used is therefore in the range of approximately 300,000 to 80,000, preferably in the range of about 250,000 to 110,000 and particularly preferably in the range of about 220,000 to 130,000.
- reaction partner it is of crucial importance to select the reaction partner so that it about its functional groups with the CR polypropylene, for example additive or through a substitution reaction.
- This functionality is then used to when dyeing from aqueous dye liquor, the respective dyes, according to their Interaction possibilities, react with the functional groups and thereby deep and create permanent dyeings of the polypropylene yarn.
- Only through this later Incorporation of reactive groups according to the invention are in the polypropylene chain necessary anchor groups are available, which also have connections other than van der Waalssche, for example ionic or covalent binding mechanisms, are able to interact with the respective dyes to a greater extent and thus allow deeper staining.
- CR polypropylene suitable for fiber formation is thus used together with a certain reactant processed together, thereby during the extrusion and the necessary conditions for creating the thread are created, that a dye used in a later dyeing process out of aqueous dye liquor can wind up and is also sufficiently liable.
- Grafting methods that can lead to similar modifications is according to the
- the method according to the invention is not a separate, and therefore costly, processing step necessary. The invention thus not only opens up an inexpensive method, but also access to a previously unattainable market, which of fast changing fashion-related color specifications is determined.
- Another advantage of the invention is that the CR polypropylene is almost independent of its molecular weight and its molecular weight distribution can be used.
- a difunctional carboxylic acid or a corresponding carboxylic acid derivative in particular a carboxylic acid ester, a carboxylic anhydride, a carboxamide, a carboximide, a carboxylic acid halide or a Use carbonitrile.
- a carboxylic acid ester a carboxylic acid ester
- a carboxylic anhydride a carboxamide
- a carboximide a carboxylic acid halide or a Use carbonitrile.
- the reactant is used in an amount of up to about 12% by weight, preferably up to about 3% by weight and in particular up to about 1% by weight. The lower the one used The amount of the reactant is, the cheaper the process is.
- reaction initiator it can accelerate the reaction be advantageous to use a peroxidic additive as a reaction initiator.
- a peroxidic additive as a reaction initiator.
- This will used in conventional amounts, the weight percent concentration of which about Power of ten is lower than that of the reaction partner.
- suitable Reaction initiators have been inorganic and organic peroxides, such as 2,5-dimethyl-2,5-bis- (t.-butylperoxy-hexane).
- the spun filament yarns have residual elongation values in the Magnitude of 200-700%. This results in that for post-stretching drawing ratios of about 1: 6.4 to be applied to a final elongation of about 25% to 1: 2.4 resulting filament stretch titer of preferably about 2.5-3.2 dtex.
- the in the stretched filament yarns achieved tensile strengths are in the range of about 50-60cN / tex and do not differ from yarns made from unmodified polypropylene were manufactured.
- the yarns according to the invention can, under customary conditions, form textile fabrics, preferably processed into knitted fabrics.
- Another object of the present invention is a method for dyeing the invention Polypropylene yarns and textile fabrics.
- the polypropylene yarns of the invention and the fabrics of the invention in a simple manner using a standard extraction process from an aqueous dye liquor be colored. It is possible, using conventional dye concentrations, based on the weight of the goods, to achieve colorations with extremely large depths of color. It can be used almost any type of dye that is capable of its own functional groups with the polypropylene yarns according to the invention or React fabrics. This will not only make one deep but also one permanent coloring achieved.
- Acid, disperse and reactive dyes have also been found to be particularly suitable proven cationic dyes. When using these dyes it is possible to to be observed by the dye manufacturers in the dyeing conditions specified in the color cards.
- dyeing aids such as ionic and nonionic Wetting, dispersing, finishing, antistatic and leveling agents as well as retarders.
- Hostalen PPU 1780F1 CR polypropylene granules for fiber applications with a melt index of MFR 25 (melt flow rate, at 2.16kg / 10min) is mechanically with powdered pyromellitic dianhydride, mixed in the form that the proportion of pyromellitic dianhydride in the mixture is 0.5% by weight. This mixture is fed to the extrusion spinning plant and processed into filament yarns at a melt temperature of 285 ° C.
- Example 1 processed into filament yarns.
- Example 2 Commercial CR polypropylene granules, as described in Example 1, are used with a Masterbatch available from Hoechst AG under the name Hostamont TP AR 504 mixed from polypropylene and maleic anhydride, so that in the mixture Mixing proportion of 1.75% maleic anhydride is included. This mixture is in the Extrusion spinning system processed to filament yarns at 235 ° C.
- Granule mixtures as described in Examples 1 and 2, but provided with each a further additive in a concentration of 0.5 or 1 g / kg of granulate mixture become filament yarns at the temperatures given in the examples mentioned processed.
- the additive mentioned in turn represents a mixture consisting of low molecular weight Polypropylene and 7.5% by weight 2,5-dimethyl-2,5-bis (t-butylperoxy-hexane).
- Granule mixtures as described in Examples 5 to 8, only with a substitute for that there pyromellitic dianhydride used by caprolactam, are at temperatures of 265 ° C processed into filament yarn.
- Knitted fabrics made from filament yarns of Example 4 are dyed in a closed dyeing beaker according to the following program: enter the liquor at 60 ° C. and dwell for 15 minutes, then heat to 125 ° C. within 45 minutes and dye at this temperature for 120 minutes, then dye Cool to 50 ° C for 40 min, take colored samples and aftertreat 60 min at boiling temperature in an open bath with 1-2 g / l of a polyglycol ether derivative and soda.
- dye liquors with a liquor ratio of 1:50 and a pH value between pH2 and pH10 are generally 0.1-5% in cationic dye and contain 5 g / l of an anionic, synergetic surfactant mixture.
- Example 4 CIBasic Blue 5 3% 4 34.66 Example 4 CIBasic Blue 5 3% 6 36.69 Example 4 CIBasic Blue 5 3% 8th 40.30 Example 4 CIBasic Blue 5 3% 10 38.48
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Artificial Filaments (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19746635A DE19746635B4 (de) | 1997-10-22 | 1997-10-22 | Verfahren zur Herstellung von aus wäßriger Färbeflotte färbbaren modifizierten Polypropylengarnen sowie deren Verwendung |
| DE19746635 | 1997-10-22 | ||
| PCT/EP1998/006700 WO1999020817A1 (de) | 1997-10-22 | 1998-10-22 | Verfahren zur herstellung von aus wässriger färbeflotte färbbaren modifizierten polypropylengarnen sowie deren verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP1025293A1 EP1025293A1 (de) | 2000-08-09 |
| EP1025293B1 true EP1025293B1 (de) | 2003-06-25 |
Family
ID=7846280
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP98958229A Expired - Lifetime EP1025293B1 (de) | 1997-10-22 | 1998-10-22 | Verfahren zur herstellung von aus wässriger färbeflotte färbbaren modifizierten polypropylengarnen sowie deren verwendung |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6555038B1 (enrdf_load_stackoverflow) |
| EP (1) | EP1025293B1 (enrdf_load_stackoverflow) |
| JP (1) | JP4188557B2 (enrdf_load_stackoverflow) |
| AT (1) | ATE243784T1 (enrdf_load_stackoverflow) |
| DE (1) | DE19746635B4 (enrdf_load_stackoverflow) |
| WO (1) | WO1999020817A1 (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100591811C (zh) * | 2004-04-15 | 2010-02-24 | 清华大学 | 纺丝方法 |
| KR102162681B1 (ko) * | 2019-12-16 | 2020-10-07 | 주식회사 성화다이텍 | 개질 폴리프로필렌 원사에 대한 염착 및 견뢰도 특성 향상을 위해 개선된 공정이 적용된 염색방법 |
| KR102176636B1 (ko) * | 2020-01-23 | 2020-11-09 | 홍해숙 | 개질된 폴리프로필렌 원사에 대한 염착 및 견뢰도 향상을 위한 염색방법 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT610638A (enrdf_load_stackoverflow) | 1959-06-09 | |||
| NL270024A (enrdf_load_stackoverflow) * | 1960-10-07 | 1900-01-01 | ||
| BR6237778D0 (pt) * | 1961-04-12 | 1973-01-11 | W Taban | Processo continuo para produzir um poli-etileno modificado por um composto de acido maleico solido e poli-etileno modificado por composto de acido maleico solido |
| US3862265A (en) * | 1971-04-09 | 1975-01-21 | Exxon Research Engineering Co | Polymers with improved properties and process therefor |
| CA993592A (en) * | 1971-04-09 | 1976-07-20 | Thomas J. Grail | Polymers with improved properties and process therefor |
| CH641304B (de) * | 1977-12-28 | Ciba Geigy Ag | Verfahren zur herstellung von loesungen von salzen wasserloeslicher carbonsaeuren kationischer farbstoffe bzw. optischer aufheller. | |
| JPS54112990A (en) * | 1978-02-24 | 1979-09-04 | Idemitsu Kosan Co Ltd | Preparation of modified polypropylene |
| IT1155437B (it) * | 1982-12-22 | 1987-01-28 | Montedison Spa | Fibre tessili di polimeri olefinici funzionalizzati e procedimento per la loro preparazione |
| DE4030669A1 (de) * | 1990-09-28 | 1992-04-02 | Hoechst Ag | Beidseitig siegelbare, biaxial orientierte polyolefinmehrschichtfolie mit sehr guten optischen eigenschaften |
| US5587434A (en) * | 1995-10-13 | 1996-12-24 | Union Carbide Chemicals & Plastics Technology Corporation | Process for polymer degradation |
-
1997
- 1997-10-22 DE DE19746635A patent/DE19746635B4/de not_active Expired - Fee Related
-
1998
- 1998-10-22 EP EP98958229A patent/EP1025293B1/de not_active Expired - Lifetime
- 1998-10-22 AT AT98958229T patent/ATE243784T1/de not_active IP Right Cessation
- 1998-10-22 WO PCT/EP1998/006700 patent/WO1999020817A1/de active IP Right Grant
- 1998-10-22 US US09/529,929 patent/US6555038B1/en not_active Expired - Fee Related
- 1998-10-22 JP JP2000517132A patent/JP4188557B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ATE243784T1 (de) | 2003-07-15 |
| JP2001520331A (ja) | 2001-10-30 |
| JP4188557B2 (ja) | 2008-11-26 |
| DE19746635A1 (de) | 1999-04-29 |
| DE19746635B4 (de) | 2004-09-02 |
| EP1025293A1 (de) | 2000-08-09 |
| US6555038B1 (en) | 2003-04-29 |
| WO1999020817A1 (de) | 1999-04-29 |
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