EP0578794A1 - Verfahren zur verbesserung des wärmschutzes von polyamiden 6.6-filamenten und damit hergestellte filamente - Google Patents
Verfahren zur verbesserung des wärmschutzes von polyamiden 6.6-filamenten und damit hergestellte filamenteInfo
- Publication number
- EP0578794A1 EP0578794A1 EP19930901582 EP93901582A EP0578794A1 EP 0578794 A1 EP0578794 A1 EP 0578794A1 EP 19930901582 EP19930901582 EP 19930901582 EP 93901582 A EP93901582 A EP 93901582A EP 0578794 A1 EP0578794 A1 EP 0578794A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- filaments
- iodide
- polyamide
- quaternary phosphonium
- heat
- 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.)
- Withdrawn
Links
- 239000004952 Polyamide Substances 0.000 title claims abstract description 17
- 229920002647 polyamide Polymers 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims abstract description 14
- 238000009413 insulation Methods 0.000 title claims 2
- LSMAIBOZUPTNBR-UHFFFAOYSA-N phosphanium;iodide Chemical group [PH4+].[I-] LSMAIBOZUPTNBR-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000005406 washing Methods 0.000 claims abstract description 9
- 238000004043 dyeing Methods 0.000 claims abstract description 7
- 239000008187 granular material Substances 0.000 claims description 9
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 8
- ICHYAUXLTDROHM-UHFFFAOYSA-M benzhydryl(triphenyl)phosphanium;iodide Chemical compound [I-].C1=CC=CC=C1C([P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 ICHYAUXLTDROHM-UHFFFAOYSA-M 0.000 claims description 3
- CYUKLJGLQGQRCJ-UHFFFAOYSA-N triphenyl(trityl)phosphanium Chemical compound C1=CC=CC=C1C([P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CYUKLJGLQGQRCJ-UHFFFAOYSA-N 0.000 claims description 3
- JOZHCQBYRBGYAJ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 JOZHCQBYRBGYAJ-UHFFFAOYSA-M 0.000 claims description 2
- 239000000835 fiber Substances 0.000 abstract description 2
- 239000010949 copper Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 229910052802 copper Inorganic materials 0.000 description 8
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 8
- 229910001868 water Inorganic materials 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 7
- 229920002302 Nylon 6,6 Polymers 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 4
- -1 Lil Chemical class 0.000 description 4
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000005749 Copper compound Substances 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 206010003549 asthenia Diseases 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001880 copper compounds Chemical class 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 150000004694 iodide salts Chemical class 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- XZEDOJJUYAVDJB-UHFFFAOYSA-N 1,1-diiododecane Chemical compound CCCCCCCCCC(I)I XZEDOJJUYAVDJB-UHFFFAOYSA-N 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- SRYAPISJVHGDFA-UHFFFAOYSA-N 4,4-dimethyl-9,10-dihydro-4ah-acridine Chemical compound C1=CC=C2NC3C(C)(C)C=CC=C3CC2=C1 SRYAPISJVHGDFA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000004953 Aliphatic polyamide Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000008351 acetate buffer Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229920003231 aliphatic polyamide Polymers 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- UKFWSNCTAHXBQN-UHFFFAOYSA-N ammonium iodide Chemical class [NH4+].[I-] UKFWSNCTAHXBQN-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- KFZGFJXYQHKJJV-UHFFFAOYSA-N benzene dihydroiodide Chemical compound I.I.C1=CC=CC=C1 KFZGFJXYQHKJJV-UHFFFAOYSA-N 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- REJGOFYVRVIODZ-UHFFFAOYSA-N phosphanium;chloride Chemical group P.Cl REJGOFYVRVIODZ-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000009971 piece dyeing Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003336 secondary aromatic amines Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- AEFPPQGZJFTXDR-UHFFFAOYSA-M tetraphenylphosphanium;iodide Chemical compound [I-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 AEFPPQGZJFTXDR-UHFFFAOYSA-M 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- IZYFBZDLXRHRLF-UHFFFAOYSA-N tritylphosphane;hydroiodide Chemical compound [I-].C=1C=CC=CC=1C(C=1C=CC=CC=1)([PH3+])C1=CC=CC=C1 IZYFBZDLXRHRLF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/60—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyamides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/50—Phosphorus bound to carbon only
-
- 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
- D01F1/00—General methods for the manufacture of artificial filaments or the like
- D01F1/02—Addition of substances to the spinning solution or to the melt
- D01F1/10—Other agents for modifying properties
Definitions
- the invention relates to a method for improving the heat protection of polyamide 6.6 filaments based on Cu / l and filaments produced therewith.
- Heat protection systems for polyamide 6.6 on Cu / l resp. Cu / I / Br bases are known (US-A-3 947 424).
- the iodides are in the form of alkali, alkaline earth or substituted or. contain unsubstituted ammonium iodides. They are easy to wash out of the heat-protected nylon 66 yarns with warm water.
- the washability of the heat protection additives is meaningless because tire yarns during processing - apart from brief impregnation with the dip solution - are not subject to wet finishing operations and are enclosed in rubber.
- secondary aromatic amines the NH group of which can also be a ring member of a heterocycle, provide non-washable thermal protection for polyamides (for example alkylated phenothiazine derivatives; 5,5-dimethylacridane; N, N'-diarylphenylene) diamine).
- polyamides for example alkylated phenothiazine derivatives; 5,5-dimethylacridane; N, N'-diarylphenylene
- REPLACEMENT LEAF Copper (I) benzothiazolyl-2-mercaptide, 2-mercaptobenzimidazole and unsubstituted benzimidazole have become known.
- the additives mentioned do not give any white threads in the presence of copper, for example as Cul, and are not able to reduce the washability of water-soluble iodides, such as Lil, NaI or KI, added in a known manner from the yarn.
- the object of the invention is to provide a method which makes it difficult to wash out heat protection for polyamides based on Cu / l /.
- Another task is to reduce the tensile strength loss of an industrial yarn through the improved heat protection.
- This object is achieved according to the invention by adding 0.2 to 1.0% by weight, preferably 0.3 to 0.8% by weight, of a guaternary phosphonium iodide to the polyamide.
- those phosphonium iodides have proven to be suitable whose solubility in boiling water (96-98 ° C.) is less than 10.0 g / 1, preferably less than 0.8 g / 1.
- the quaternary phosphonium iodides are melt-soluble, i.e. are homogeneously distributable in a polyamide melt.
- the addition is advantageously carried out in the polyamide melt before extrusion.
- the phosphonium iodide can also the granules before Melting powdered.
- the quaternary phosphonium iodides contain one or more triarylphosphoniono, preferably triphenylphosphoniono groups and comprise the following 2 types:
- Ph phenyl and R 1 can optionally be an aryl, arylalkyl or alkyl radical.
- the aryl groups can also carry up to three substituents, for example tertiary butyl or other alkyl groups, -OH, -Cl, -Br or I.
- R 1 is a phenyl, benzyl, benzhydryl, trityl - or a generally unbranched alkyl radical having at least four, preferably at least ten, carbon atoms.
- Suitable examples of iType 1 are tetraphenylphosphonium iodide, benzyltriphenylphosphonium iodide, benzhydryl triphenylphosphonium iodide and trityl triphenylphosphonium iodide.
- Type 2 with the general formula [Ph 3 PR 2 -PPh3] 2+ 2l _ , wherein R 2 is optionally an o-xylylene, p-xylylene or an alpha, omega-alkanediyl radical.
- the filaments After washing out / blind dyeing, the filaments have a tensile strength loss of less than 17% at 8 h / 177 ° C
- the application of the method is not limited to filaments and fibers, but is also intended for foils and other shaped articles.
- the quaternary phosphonium iodides mentioned are prepared in a known manner by reacting triphenylphosphine with the corresponding aliphatic mono- or dihalohydrocarbons in the individual case, such as solvents, such as N, N-dimethylformamide, chloroform and others. If one does not start from an iodine alkane, which immediately provides the desired salt, but from chlorinated or bromocarbons, then the quaternary phosphonium chlorides or bromide obtained from hot aqueous solution can be obtained by double reaction with NaI or KI into the much heavier ones convert soluble iodide.
- the quaternary phosphonium iodides used according to the invention are used together with a copper compound, preferably copper (I) iodide, in heat-protection systems for aliphatic polyamides which are difficult to wash out, the Cu content in the product being between 10 and 100 ppm, preferably between 15 and 65 ppm and the I content between 300 and 1500 ppm is selected, the I content comprising the iodine contained in the quaternary phosphonium iodide and in the Cul optionally used.
- the molar ratio l / Cu is always at least 2 and is preferably chosen between 3 and 25.
- the quaternary phosphonium iodides can either be powdered onto finished granules or added to the polyamide at the extruder inlet. If the granules do not already contain a copper compound, one is applied to the granules at the same time, copper (I) iodide being particularly preferred because this forms polyamide-melt-soluble diiodocuprates (I) with the quaternary phosphonium iodides. This reaction may take place well below the polyamide melting point.
- REPLACEMENT LEAF Circular knit stockings were produced from both nylon 66 threads, which were subjected to simultaneous aging tests by heating in air both in the raw state, after washing and after blind dyeing.
- the progress according to the invention is shown on the basis of the tensile strength losses shown in Table 1.
- thermoresistance test is carried out as follows: Filaments or a knitted fabric are hung tension-free in a chamber (Binder type Led heating cabinet) with a closed air circulation system and treated at 177 ⁇ 1 ° C for 8 h. After the test period, the samples are measured at room temperature.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Artificial Filaments (AREA)
- Coloring (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH29892 | 1992-02-03 | ||
| CH298/92 | 1992-02-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0578794A1 true EP0578794A1 (de) | 1994-01-19 |
Family
ID=4183808
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP19930901582 Withdrawn EP0578794A1 (de) | 1992-02-03 | 1993-01-21 | Verfahren zur verbesserung des wärmschutzes von polyamiden 6.6-filamenten und damit hergestellte filamente |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0578794A1 (enrdf_load_stackoverflow) |
| JP (1) | JPH06507215A (enrdf_load_stackoverflow) |
| BR (1) | BR9303967A (enrdf_load_stackoverflow) |
| TW (1) | TW210368B (enrdf_load_stackoverflow) |
| WO (1) | WO1993015138A1 (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5768875A (en) * | 1993-03-17 | 1998-06-23 | Rhone-Poulenc Viscosuisse S.A. | Filter fabric with core sheating thread, and a bag produced therefrom |
| US8101252B1 (en) | 1997-10-31 | 2012-01-24 | Asahi Kasei Kabushiki Kaisha | Air bag |
| DE19847626B4 (de) * | 1998-10-15 | 2004-08-19 | L. Brüggemann KG | Mit Kupfersalz und aliphatischem halogeniertem Phosphat stabilisierte Polyamidzusammensetzung |
| WO2011055562A1 (ja) * | 2009-11-09 | 2011-05-12 | 旭化成せんい株式会社 | エアバッグ用織物およびエアバッグ |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1258079B (de) * | 1966-02-23 | 1968-01-04 | Bayer Ag | Stabilisierung von Polyamiden |
| DE1261668B (de) * | 1966-04-28 | 1968-02-22 | Bayer Ag | Waermestabilisieren von Polyamiden |
| DE1694067A1 (de) * | 1966-04-28 | 1971-06-09 | Bayer Ag | Stabilisierte Polyamide |
-
1993
- 1993-01-20 TW TW82100351A patent/TW210368B/zh active
- 1993-01-21 JP JP5512827A patent/JPH06507215A/ja active Pending
- 1993-01-21 BR BR9303967A patent/BR9303967A/pt not_active Application Discontinuation
- 1993-01-21 EP EP19930901582 patent/EP0578794A1/de not_active Withdrawn
- 1993-01-21 WO PCT/CH1993/000015 patent/WO1993015138A1/de not_active Application Discontinuation
Non-Patent Citations (1)
| Title |
|---|
| See references of WO9315138A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| BR9303967A (pt) | 1994-12-13 |
| JPH06507215A (ja) | 1994-08-11 |
| WO1993015138A1 (de) | 1993-08-05 |
| TW210368B (enrdf_load_stackoverflow) | 1993-08-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
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| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): CH DE ES FR GB IT LI LU NL |
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| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
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| 18D | Application deemed to be withdrawn |
Effective date: 19940206 |