WO2009095440A1 - Matières de moulage à base de polyamide [5, 10] transparentes - Google Patents

Matières de moulage à base de polyamide [5, 10] transparentes Download PDF

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Publication number
WO2009095440A1
WO2009095440A1 PCT/EP2009/051006 EP2009051006W WO2009095440A1 WO 2009095440 A1 WO2009095440 A1 WO 2009095440A1 EP 2009051006 W EP2009051006 W EP 2009051006W WO 2009095440 A1 WO2009095440 A1 WO 2009095440A1
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WIPO (PCT)
Prior art keywords
polyamide
molding compositions
compositions according
weight
nucleating agent
Prior art date
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PCT/EP2009/051006
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German (de)
English (en)
Inventor
Motonori Yamamoto
Weol Kyu Jeong
Arnold Schneller
Rolf-Egbert GRÜTZNER
Freddy Gruber
Jürgen Deininger
Original Assignee
Basf Se
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Publication of WO2009095440A1 publication Critical patent/WO2009095440A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
    • C08G69/28—Preparatory processes
    • 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
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0083—Nucleating agents promoting the crystallisation of the polymer matrix
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C08L77/06—Polyamides derived from polyamines and polycarboxylic acids

Definitions

  • the present invention relates to polyamide [5,10] molding compositions having a transmission measured according to ASTM D1003 on 1 mm thick, injection-molded plates of greater than or equal to 80% and in particular comprising polyamide [5,10] molding compositions
  • the present invention relates to a method and masterbatches for producing such molding compositions, the use of such molding compositions for the production of moldings of any kind and the moldings obtainable in this case, preferably automotive body parts of any kind or electronic components, films and fibers.
  • polyamide [5,10] is little known in the literature.
  • Commercially available polyamides such as polyamide [6] or polyamide [6,10] can not always be completely satisfactory in terms of their transparency.
  • the aim of the present invention was to increase the transparency of polyamides without impairing the mechanical properties.
  • the polyamides [5, 10] according to the invention have a significantly higher transparency than comparable polyamide [6] and polyamide [6,10] molding compounds.
  • this property occurs in the case of molding compositions having a nucleating agent content of from 0.001 to 5% by weight;
  • the mechanical properties such as impact resistance are also improved.
  • the polyamides [5, 10] can be prepared as described in WO 2007/113127.
  • the polyamides [5, 10] in the fiber-reinforced case are generally in a proportion of from 40 to 96, preferably 45 to 92 and in particular 50 to 91% by weight and in the non-fiber-reinforced case usually in a proportion of 70 to 99.9, preferably 95 to 99.8 and in particular 97 to 99.8 wt .-%.
  • molding compositions according to the invention preferably sodium or calcium phenylphosphinate, calcium fluoride, finely divided polytetrafluoroethylene, polyamide [2,2], polyamide [4,6], boron compounds, alumina, silica or talc. Particularly preferred are talc and polyamide [2,2].
  • Talc which [(OH) 2 / Si4 ⁇ io] 3 or MgO ⁇ is a hydrated magnesium silicate having the composition Mg 3 SiO 2 4 ⁇ H 2 O, being particularly preferred.
  • These so-called three-layer phyllosilicates have a triclinic, monoclinic or rhombic crystal structure with a platelet-like appearance.
  • Mn, Ti, Cr, Ni, Na and K may be present, wherein the OH group may be partially replaced by fluoride.
  • talc the particle size of which is 99.5%.
  • the particle size distribution is usually determined by sedimentation analysis DIN 6616-1 and is preferably:
  • the nucleating agents A) are used in a concentration of 0.001 to 5, preferably 0.01 to 1, 0 and particularly preferably 0.05 to 0.2 wt .-%.
  • fiber-containing fillers B carbon fibers, glass fibers, called, in amounts of 1 to 60 wt .-%, in particular from 10 to 50, preferably from 20 to 40 wt .-% are used.
  • Preferred fibrous fillers are glass fibers, carbon fibers, aramid fibers, potassium titanate fibers and natural fibers, glass fibers being particularly preferred as E glass. These can be used as rovings or in particular as chopped glass in the commercial forms.
  • the fibers generally have a diameter of 3 to 30 microns, preferably 6 to 20 microns and more preferably from 8 to 15 microns.
  • the fiber length in the compound is generally 20 .mu.m to 1000 .mu.m, preferably 180 to 500 .mu.m and more preferably 200 to 400 .mu.m.
  • Natural fibers are understood as meaning cellulose fibers, hemp fibers, sisal or kenaf.
  • the fibrous fillers can be surface-pretreated with a silane compound.
  • Suitable silane compounds are those of the general formula
  • X is NH 2 -, CH 2 -CH-, HO-,
  • O n is an integer from 2 to 10, preferably 3 to 4 m, an integer from 1 to 5, preferably 1 to 2 k, an integer from 1 to 3, preferably 1
  • Preferred silane compounds are aminopropyltrimethoxysilane, aminobutyltrimethoxysilane, aminopropyltriethoxysilane, aminobutyltriethoxysilane and the corresponding silanes which contain a glycidyl group as substituent X.
  • the silane compounds are generally used in amounts of from 0.01 to 2, preferably from 0.025 to 1, 0 and in particular from 0.05 to 0.5% by weight (based on C) of the surface coating.
  • Suitable additives C) are also acicular mineral fillers C).
  • the term "needle-shaped mineral fillers” is understood to mean a mineral filler with a pronounced, needle-like character.
  • An example is acicular wollastonite.
  • the mineral has an L / D (length diameter) ratio of 8: 1 to 35: 1, preferably 8: 1 to 1: 1: 1.
  • the mineral filler may optionally be pretreated with the silane compounds mentioned above; however, pretreatment is not essential.
  • particulate fillers C which may be mentioned are kaolin, calcined kaolin, wollastonite and chalk, and additionally platelet or needle-shaped fillers, preferably in amounts of between 0.1 and 20% by weight.
  • Boehmite, bentonite, montmorillonite, vermicullite, hectorite, laponite, powdered quartz, mica, feldspar, calcium silicate and magnesium carbonate are preferably used for this purpose.
  • dyes such as nigrosine and pigments such as titanium dioxide, zinc sulfide, ultramarine blue, iron oxide, anthraquinones, quinacridones, phthalocyanines, perylenes or mixtures thereof have proven to be suitable fillers.
  • an electrically conductive additive can be added as component C).
  • Suitable electrically conductive additives are, for example, carbon nanotubes, graphite or conductive carbon black.
  • Carbon nanotubes in the context of the present invention are carbon-containing macromolecules in which the carbon has (mainly) graphite structure and the individual graphite layers are arranged in a tubular manner.
  • Nanotubes and their synthesis are already known in the literature (for example J. Hu et al., Acc. Chem. Res. 32 (1999), 435-445). In principle, any type of nanotube can be used in the context of the present invention.
  • the diameter of the individual tubular graphite layers is 4 to 12 nm, in particular 5 to 10 nm.
  • Nanotubes can be divided into so-called single-walled nanotubes (SWNTs) and multiwalled nanotubes (MWNTs). differ. Thus, in the MWNTs, several graphite tubes are superposed on each other.
  • the outer shape of the tubes may vary, this may have uniform diameter inside and outside, but there are also knot-shaped tubes and worm-like structures (vermicular) produced.
  • the aspect ratio (length of the respective graphite tube to its diameter) is at least> 10, preferably> 5.
  • the nanotubes have a length of at least 10 nm.
  • MWNTs are preferred as component E).
  • the MWNTs have an aspect ratio of about 1000: 1 and an average length of about 10,000 nm.
  • the BET specific surface area is generally from 50 to 2000 m 2 / g, preferably from 200 to 1200 m 2 / g.
  • the resulting in the catalytic preparation impurities are generally according to HRTEM from 0.1 to 12%, preferably from 0.2 to 10%.
  • Suitable nanotubes can be obtained under the name "multiwaH” from Hyperion Catalysis Int., Cambridge MA (USA) (see also EP 205 556, EP 969 128, EP 270 666, US Pat. No. 6,844,061).
  • any conventional form of carbon black can be used, suitable, for example, the commercial product Ketjenblack 300 Akzo.
  • Conductivity can also be used for conductivity modification. Due to graphitic layers embedded in amorphous carbon, soot conducts electrons (F. Camona, Ann. Chim., Fr., 13, 395 (1988)). The power line takes place within the aggregates of soot particles and between the aggregates, if the distances between the aggregates are small enough. In order to achieve conductivity with the lowest possible dosage, preference is given to using carbon blacks with anisotropic structure (G. Wehner, Advances in Plastics Technology, APT 2005, Paper 1, Katowice 2005).
  • the primary particles combine to form anisotropic structures, so that the distances of the soot particles necessary for achieving conductivity in compounds are achieved even at comparatively low loading (C. Van Bellingen, N. Probst, E. Grivei, Advances in Plastics Technology , APT 2005, Paper 13, Katowice 2005).
  • Suitable types of carbon black include, for example, an oil absorption (measured according to ASTM D 2414-01) of at least 60 ml / 100 g, preferably more than 90 ml / 100 g.
  • the BET surface area of suitable products is more than 50, preferably more than 60 m 2 / g (measured according to ASTM D 3037-89).
  • the Leitruße can be prepared by various methods (G. Wehner, Advances in Plastics Technology, APT 2005, Paper 1 1, Katowice 2005).
  • graphite can also be used as a conductivity additive.
  • Graphite is a modification of the carbon as described, for example, in AF Hollemann, E. Wieberg, N. Wieberg, "Lehrbuch der anorganischen Chemie," 91.-100th ed., Pp. 701-702
  • Graphite can be comminuted by milling
  • the particle size is in the range of 0.01 ⁇ m to 1 mm, preferably in the range of 1 to 250 ⁇ m.
  • the transparency of the mixtures according to the invention can be increased in many cases by adding 0.05 to 1.0% by weight of a phosphorus compound of the general structure
  • R and R ' are independently a C r C 8 alkyl, C r C 8 -Alkoky, aryl or substituted with C r C 6 -alkyl aryl group and Ar represents a 1, 4-phenylene, 1, 3-phenylene , 2,6-naphthylene, 2,7-naphthylene or a 4,4'-diphenylene radical or their Ci-Ce-alkyl-substituted derivatives mean are added.
  • a preferred phosphorus compound is commercially available under the designation Irgafos® P-EPQ (Ciba-Geigy).
  • component C it is possible to use further additives, such as stabilizers, oxidation inhibitors, flame retardants, agents against heat decomposition and decomposition by ultraviolet light, lubricants and mold release agents, colorants, such as dyes, plasticizers, etc.
  • additives such as stabilizers, oxidation inhibitors, flame retardants, agents against heat decomposition and decomposition by ultraviolet light, lubricants and mold release agents, colorants, such as dyes, plasticizers, etc.
  • flame retardants examples include red phosphorus, magnesium hydroxide and melamine cyanurate.
  • the stabilizers can be added to the polyamide [5,10] molding compositions at any stage in the preparation, but are preferably added as early as possible to prevent decomposition from starting already before the stabilizer is incorporated.
  • halides of metals of Group I of the Periodic Table e.g. Sodium, potassium, and / or lithium halides
  • copper (I) halides e.g. Chlorides, bromides, iodides, hindered phenols, hydroquinones, various substituted representatives of these groups and mixtures thereof in concentrations up to 1 wt .-%, based on the weight of the thermoplastic molding compositions called.
  • UV stabilizers which are generally used in amounts of up to 2% by weight, based on the molding composition, of various substituted resorcinols, salicylates, benzotriazoles and benzophenones may be mentioned.
  • Lubricants and mold release agents are usually used in quantities of max. 1 wt .-%, based on the total weight of the molding composition added. Examples of these are stearic acid, sterol alcohol and stearic acid amides.
  • the proportion of component C) in the novel molding materials is from 0 to 30% by weight, preferably from 1 to 15% by weight, particularly preferably from 1 to 5% by weight, based on the total weight the molding compound.
  • the proportion of component C) in the molding compositions according to the invention is from 0 to 10% by weight, preferably from 0.05 to 2% by weight, and particularly preferably from 0.08 to 1% by weight, with regard to stabilizer and lubricant.
  • the polyamide [5,10] molding compositions according to the invention can preferably be prepared in a three-stage process (steps i) to Ni)) by means of so-called masterbatches containing 5 to 15% by weight nucleating agent:
  • Polyamide [5,10] can be prepared by polycondensation of 1, 5 pentamethylenediamine and sebacic acid in a molar ratio of 0.95: 1, 05 to 1, 05: 0.95 by known methods.
  • the condensation can either be carried out batchwise in a batch process or else continuously.
  • a batchwise preparation of the polyamides for example, an aqueous solution of the monomers is introduced in an autoclave and heated to generally 240 to 300 ° C. A pressure of from 10 to 50 or rather 15 to 30 bar is established By relaxing excess water vapor can be kept constant for up to 4 hours.
  • the heating phase (up to the desired reaction temperature) usually takes 0.5 to 3 hours.
  • the stirring time during which the reaction mixture is maintained at 240 to 300 0 C, is usually 1 to 5 hours. Subsequently, it is depressurized to normal pressure during a period of 0.5 to 3 hours.
  • the autoclave discharge is granulated, for example in a water bath.
  • the continuous procedure can be carried out analogously to EP129195 or 129196.
  • the masterbatches and the molding compositions according to the invention can be prepared by processes known per se, by mixing the components polyamide [5.10], A) and, if appropriate, B) and C), in the melt at elevated temperatures or else by mixing Components in mixing devices. It is expedient to use extruders for this purpose, for example single-screw or twin-screw extruders or other conventional plasticizing devices, such as Brabender mills or Banbury mixers. After extrusion, the extrudate can be cooled and comminuted. It is also possible to premix individual components and then to add the remaining starting materials individually and / or likewise mixed. The mixing temperatures are usually 230 to 320 0 C.
  • the molecular weight (Mn) of the polyamides [5, 10] according to the invention is preferably in the range from 1000 to 100000, in particular in the range from 9000 to 75000 and particularly preferably in the range from 10 000 to 50 000 g / mol.
  • the molding compositions according to the invention have, in particular, excellent transparency or, in certain mixtures, a surprisingly high translucency.
  • the transmission was determined on a 1-mm-thick, injection-molded plate according to ASTM D1003 (MT / FT).
  • the ASTM D1003 defines the total transmission as the ratio of transmitted light to incident light - measured in percent.
  • the injection molding conditions for the production of plates melting temperature of 260 0 C, Mold temperature of 60 0 C.
  • the measurements were carried out on the device haze-gard plus from BYKGardner.
  • the polyamide [5,10] molding compounds show a transmission of over 80%.
  • Comparable literature known polyamides have a significantly lower transmission.
  • the transmission can be increased to over 90% according to ASTM D1003.
  • the molding compositions according to the invention are further distinguished by good notched impact toughness, improved flowability and surprisingly high ductility at -30 0C.
  • the molding compositions according to the invention have a higher heat resistance (HDT B).
  • Cylinder head covers are suitable for the production of fibers, films and moldings of any kind, especially for automotive and electronics applications.
  • dashboards Inside the car, there is use for dashboards, steering column switches, seat parts, headrests, center consoles, transmission components and door modules, in the car exterior door handles, exterior mirror components, windscreen wiper components, windscreen wiper housings, grilles, roof rails, sunroof frames, engine covers, cylinder head covers, intake manifolds , Windscreen wipers and bodywork exterior parts such as fenders, door trim, tailgates, spoilers, side panels, roof modules and hoods.
  • Suitable electronic components are e.g. Cell phone cases, laptop components, touch screen frames, navigator screen frames, calculator components, etc.
  • the molding compositions according to the invention are suitable for the production of spectacle frames and spectacle lenses.
  • the molding compositions according to the invention are also suitable for the production of films, for example for the packaging of foods.
  • films which have 0.01 to 1% by weight of polyamide [2.2] or, in particular, talc, have proved suitable here.
  • the molecular weight Mn of the polymers is determined as follows:
  • HFIP hexafluoroisopropanol
  • the viscosity number of the polyamides was measured according to EN ISO 1628-1 on 0.5% strength by weight solutions in 96% by weight sulfuric acid.
  • the polymers generally have a VZ of 10 to 400 ml / g, preferably 30 to 300 and particularly preferably 50 to 250 ml / g.
  • the MVR was measured according to ISO1133 (275 ° C, 5 kg load).
  • the polyamides according to the invention have an MVR of 5 to 500 ml / 10 min, preferably 10 to 400, particularly preferably 20 to 300.
  • the transmission was determined on a 1 mm thick plate according to ASTM D1003. The measurements were performed on the haze-gard plus instrument by BYKGardner. The injection molding conditions for the production of plates: melting temperature of 260 0 C, mold temperature of 60 0 C.
  • the impact strength was determined according to ISO179-2.
  • Pentylenediamine was prepared by fermentation with Corynebacterium glutamicum (see WO2007 / 113127).
  • Ultramid® B3 from BASF SE (VZ 151 ml / g) was used.
  • X10 1.7 ⁇ m.
  • X90 10.8 microns (measured by laser diffraction, wherein the minerals were homogenized in a suspension cell in a deionized water / 1% CV K8 surfactant mixture (distributor: CV-Chemievertrieb, Hannover) (magnetic stirrer, 60 rpm). Production of masterbatch and compounding
  • This masterbatch concentrate was treated with additional polyamide [5,10] in a ZSK25 to obtain the desired concentration (0.1%) of talc.
  • Example 4 PA [5.10] (Example 1) and 0.1% talc IT extra were compounded.
  • Comparative Example 5 PA [6,10] (Comparative Example 2) and 0.1% talc IT extra were compounded.
  • Comparative Example 6 PA 6 (Comparative Example 3) and 0.1% talc IT extra were compounded.
  • the polyamides according to the invention have, in comparison to commercially available polyamides [6, 10] and [6], a high transmission according to ASTM D1003, with simultaneously good impact strength (ISO 179-2) and heat resistance (ISO75-2).

Abstract

L'invention concerne des matières de moulage à base de polyamide [5, 10] transparentes, dont la transmission, mesurée selon ASTM D1003 sur des plaques moulées par injection de 1mm d'épaisseur, est supérieure ou égale à 80%, ainsi qu'un procédé et des mélanges-maîtres utilisés pour produire des matières de moulage de ce type. L'invention concerne également l'utilisation de ce type de matières de moulage pour produire des corps moulés de tout type, ainsi que les corps moulés ainsi obtenus, de préférence des éléments de carrosserie de véhicules automobiles de tout type ou des composants électroniques, des films et des fibres.
PCT/EP2009/051006 2008-01-31 2009-01-29 Matières de moulage à base de polyamide [5, 10] transparentes WO2009095440A1 (fr)

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EP08101121.5 2008-01-31

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2479405A (en) * 2010-04-09 2011-10-12 Lewis Banks Ltd Composition for protective articles for motorcycles
US8586662B2 (en) 2007-11-16 2013-11-19 Ems-Patent Ag Filled polyamide molding materials
EP2716716A1 (fr) * 2012-10-02 2014-04-09 Ems-Patent Ag Compositions de moulage à base de polyamide et leur utilisation dans la fabrication d'objets moulés
US8906653B2 (en) 2008-01-23 2014-12-09 Basf Se Method for fermentatively producing 1,5-diaminopentane
US9109115B2 (en) 2013-03-15 2015-08-18 Ems-Patent Ag Polyamide moulding compound and moulded articles produced herefrom
US9453106B2 (en) 2012-05-23 2016-09-27 Ems-Patent Ag Scratch-resistant, transparent and tough copolyamide moulding compounds, moulded articles produced therefrom and uses thereof
US9963591B2 (en) 2012-12-18 2018-05-08 Ems-Patent Ag Polyamide molding material and moldings manufactured from same
KR20200065849A (ko) * 2018-11-30 2020-06-09 롯데케미칼 주식회사 박육 제품 사출성형용 폴리아미드 수지 조성물 및 이의 성형품

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8586662B2 (en) 2007-11-16 2013-11-19 Ems-Patent Ag Filled polyamide molding materials
US8906653B2 (en) 2008-01-23 2014-12-09 Basf Se Method for fermentatively producing 1,5-diaminopentane
GB2479405A (en) * 2010-04-09 2011-10-12 Lewis Banks Ltd Composition for protective articles for motorcycles
EP2374845A3 (fr) * 2010-04-09 2012-01-04 Lewis Banks Ltd, t/a GBRacing Composition améliorée
GB2479405B (en) * 2010-04-09 2016-05-04 Lewis Banks Ltd Secondary engine covers
US9453106B2 (en) 2012-05-23 2016-09-27 Ems-Patent Ag Scratch-resistant, transparent and tough copolyamide moulding compounds, moulded articles produced therefrom and uses thereof
EP2716716A1 (fr) * 2012-10-02 2014-04-09 Ems-Patent Ag Compositions de moulage à base de polyamide et leur utilisation dans la fabrication d'objets moulés
US9133322B2 (en) 2012-10-02 2015-09-15 Ems-Patent Ag Polyamide moulding compounds and use thereof in the production of moulded articles
US9963591B2 (en) 2012-12-18 2018-05-08 Ems-Patent Ag Polyamide molding material and moldings manufactured from same
US9109115B2 (en) 2013-03-15 2015-08-18 Ems-Patent Ag Polyamide moulding compound and moulded articles produced herefrom
KR20200065849A (ko) * 2018-11-30 2020-06-09 롯데케미칼 주식회사 박육 제품 사출성형용 폴리아미드 수지 조성물 및 이의 성형품
KR102208253B1 (ko) * 2018-11-30 2021-01-27 롯데케미칼 주식회사 박육 제품 사출성형용 폴리아미드 수지 조성물 및 이의 성형품

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