EP0000726A1 - Masses à mouler contenant une polyoléfine et un carbonate alcalino-terreux ainsi que leur préparation - Google Patents

Masses à mouler contenant une polyoléfine et un carbonate alcalino-terreux ainsi que leur préparation Download PDF

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Publication number
EP0000726A1
EP0000726A1 EP7878100497A EP78100497A EP0000726A1 EP 0000726 A1 EP0000726 A1 EP 0000726A1 EP 7878100497 A EP7878100497 A EP 7878100497A EP 78100497 A EP78100497 A EP 78100497A EP 0000726 A1 EP0000726 A1 EP 0000726A1
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EP
European Patent Office
Prior art keywords
carbon atoms
parts
radical
weight
acid
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.)
Granted
Application number
EP7878100497A
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German (de)
English (en)
Other versions
EP0000726B1 (fr
Inventor
Walter Dr. Lüders
Walter Dr. Herwig
Ulrich Dr. Van Spankeren
Karlheinz Dr. Burg
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Hoechst AG
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Hoechst AG
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Application filed by Hoechst AG filed Critical Hoechst AG
Publication of EP0000726A1 publication Critical patent/EP0000726A1/fr
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Publication of EP0000726B1 publication Critical patent/EP0000726B1/fr
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    • 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
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
    • C08K5/5333—Esters of phosphonic acids
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/24—Acids; Salts thereof
    • C08K3/26—Carbonates; Bicarbonates
    • 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
    • C08K9/00—Use of pretreated ingredients
    • C08K9/04—Ingredients treated with organic substances

Definitions

  • the organophosphorus compounds of the formula (I) to be used according to the invention are phosphonic acids and their esters.
  • R represents an aralkyl radical having 1 to 18, preferably 3 to 8, in particular 2 to 6 carbon atoms.
  • the alkyl radical can be straight-chain or branched or ring-shaped.
  • R 1 also denotes an alkenyl radical having 2 to 18, preferably 2 to 12 carbon atoms, or an aralkyl radical having 7 to 13, preferably 7 to 10, in particular 7 to 9 carbon atoms, the alkyl chain of which has 1 to 3, preferably 1 or 2, carbon atoms, or an aralkenyl radical having 8 to 13, preferably 8 to 10, in particular 8 to 9 carbon atoms, the alkenyl chain of which has 2 or 3 carbon atoms.
  • the aromatic radical is a carbocyclic nucleus with 6 or 10 ring carbon atoms, which optionally carries side chains.
  • R 2 and R 3 are the same or different and each represents hydrogen, an unbranched or branched or cyclic alkyl radical having 1 to 8, preferably 2 to 8 carbon atoms, an aryl radical having 6 to 10, preferably 6 to 8 carbon atoms, an aralkyl radical having 7 to 13, preferably 7 to 10 carbon atoms, the alkyl chain of which has 1 to 3, preferably 1 or 2 carbon atoms, or an alkenyl radical with 3 to 5, preferably 3 or 4 carbon atoms.
  • Aromatic residues are preferably carbocyclic nuclei with 6 or to ring carbon atoms, which can optionally carry side chains.
  • the phosphonic acids and phosphonic acid esters to be used according to the invention can be prepared by known methods.
  • the phosphonic acids can be prepared from their tetra- or dihalides by reaction with water, by saponification of the corresponding esters, by disproportionation of phosphonic acids or by addition of phosphorous acid to olefinic double bonds; the phosphonic acid esters by reacting the phosphonic acid tetra- or dihalides with alcohols or from esters of phosphorous acid with alkyl halides (Kosolapoff, Organophosphorus Compounds, Wiley and Sons, New York, 1950; Houben-Weyl, Vol. XII / 1, Thieme Verlag Stuttgart ).
  • Suitable phosphonic acids are, for example, methanephosphonic acid, ethanephosphonic acid, propanephosphonic acid, butanephosphonic acid, n-hexanephosphonic acid, cyclohexanephosphonic acid, 2,3-dimethylbutanephosphonic acid, octanephosphonic acid, decanephosphonic acid, dodecanephosphonic acid, octadecanephosphonic acid, phenylmethanephosphonic acid, 1-phenylphosphonic acid, 1-phthalophosphonic acid, 1-phthalylphosphonic acid, 1, 2-phenyl-vinylphosphonic acid-1, 2,4-dimethyl-4-methylpentane-phosphonic acid, dimethyl-2-methylpropane-phosphonic acid and 2,4-dimethyl-butane-phosphonic acid.
  • Vinylphosphonic acid, propanephosphonic acid, hexanephosphonic acid, octanephosphonic acid, dodecanephosphonic acid, 2,4-dimethyl-4-methylpentanephosphonic acid, dimethyl-2-methylpropanephosphonic acid and 2,4-dimethylbutanephosphonic acid are preferably used.
  • Suitable phosphonic acid esters are, for example, Methanphosphonklathylester, ethanephosphonic acid diethyl ester, ethanephosphonic acid dibutyl, Butanphosphonklare dibutyl, n-Hexanphosphonklathylester, n-hexanephosphonic diphenyl, Octanphosphonklathylester, dodecanephosphonic acid dimethyl ester, Octadecanphosphonklare acid diethyl ester, vinylphosphonic acid, vinylphosphonic acid diethyl ester, vinyl phosphonic acid-di- (2 -ethyl-hexyl) -ester, vinylphosphonic acid dioctyl ester, vinylphosphonic acid diallyl ester, allylphosphonic acid diallyl ester, allylphosphonic acid dimethallyl ester, phenylmethane-phosphonic acid monoethyl ester, methanephosphonic acid eth
  • the phosphonic acids and phosphonic acid esters to be used according to the invention are added to the molding composition in an amount of 0.1-10% by weight, preferably 0.5-2% by weight, based on the filler. Mixtures of different phosphonic acids or phosphonic acid esters, or mixtures of phosphonic acid with phosphonic acid esters can also be used.
  • the filler can be a natural or synthetic, i.e. precipitated alkaline earth carbonate.
  • Suitable carbonates are, for example, limestone powder, chalk, precipitated calcium carbonate, natural magnesite, natural hydromagnesite, synthetic basic magnesium carbonate, calcium magnesium carbonate, dolomite. Calcium carbonates are preferably used.
  • alkaline earth carbonates to be used have an average particle diameter of 0.1 to 50 ⁇ m, preferably 1 to 10 ⁇ m. Mixtures of different alkaline earth carbonates can also be used.
  • the phosphonic acid or the phosphonic acid ester can be introduced into the molding composition in various ways.
  • the filler in an organic solvent, alcohols such as methanol, ethanol, butanol, hydrocarbons such as hexane, benzene, toluene, ethers such as diethyl ether, di-isopropyl ether or ketones such as acetone, diethyl ketone serve as the solvent.
  • alcohols such as methanol, ethanol, butanol
  • hydrocarbons such as hexane, benzene, toluene
  • ethers such as diethyl ether, di-isopropyl ether or ketones such as acetone, diethyl ketone
  • ketones such as acetone, diethyl ketone
  • the adhesion promoter is liquid, it can be added directly to the filler or diluted with a suitable solvent in a high-speed mixer or sprayed onto the filler in the form of a mist in the form of a mist. In this way, solid adhesion promoters can also be applied to the filler dissolved in a suitable solvent.
  • the adhesion promoter can be mixed with the polymer in a mixer and then the untreated filler can be added, or all three components, namely the polymer, the filler and the adhesion promoter can be mixed at the same time.
  • This simultaneous mixing can take place in a premixer, but also in the granulating extruder.
  • the filler is preferably first treated with the adhesion promoter.
  • Suitable base polymers for the plastic molding compositions according to the invention are 1-olefin homo- and copolymers, for example high-density and low-density polyethylene, polypropylene, 1-polybutene, 1-poly- (4-methyl) -phthaline, 1-olefin copolymers, such as ethylene Propylene copolymers and ethylene-butene copolymers, mixtures of these polymers and mixtures of these polymers with Polymers used.
  • Polyethylene is particularly preferably used.
  • the polymer content of the molding compositions is 90 to 20, preferably up to 30% by weight.
  • the molding compositions according to the invention can have the usual properties which facilitate processing and the physical properties Contain additives. As such are too Light and heat stabilizers, antioxidants, etc. as well as color pigments, flame retardants.
  • the first group is in the molding compositions generally in an amount of 0.01 to 5 percent by weight, on the amount of polymer plus filler. Color pigments and flame retardants are used in an amount according to needs.
  • An effective Stabilisat combination of poly-1-n olefination e such as high, middle, and Niederchristpolymerisate of C2 - to C 4 -1-olefins, especially polyethylene and polypropylene, or of polymers such 1-olefins, for example, consist, in each case based on 100 parts by weight of polymer, 0.05 to 4 parts by weight of a phenolic stabilizer optionally 0.01 to 4 parts by weight of one containing costabilizer, and optionally 3 parts by weight of a basic or neutral such as calcium stearate or zinc stearate, and optionally 0.1 to 4 parts by weight of a phosphite and optionally 0.01 to 4 parts by weight of a known UV from the Group of the alkoxyhydroxybenzophenones, hydroxyphenylbenzotriazoles, benzylidene malonic acid monotrilesters or the so-called quencher (for example nickel chelates).
  • quencher for example nickel chelates
  • a polymerization initiator for example benzoyl peroxide, dicumyl peroxide, tert-butyl hydroperoxide, tert-butyl peroctoate, azobisisobutyronitrile in an amount of 0.01 to 1 percent by weight, based on the amount of unsaturated phosphonic acid or phosphonic acid esters can be added.
  • thermoplastic molding composition according to the invention have very good impact strength and impact strength, which makes them particularly suitable for the production of technical articles.
  • adhesion promoters to be used according to the invention are that they have a favorable influence on the flow behavior of the polymer melt during injection molding and, for example, facilitate the filling of the mold in the production of complicated injection molded parts.
  • test specimens are listed in Table I.
  • a 1/2 standard rod is used as a test specimen.
  • Elongation and tensile strength are determined according to DIN 53 455, impact strength according to DIN 53 453 (30 mm jaw spacing, transverse position) impact strength according to DIN 53 448, ball indentation hardness according to DIN 52 456 and the modulus of elasticity according to DIN 53 457.
  • Example 2 The same calcium carbonate as in Example 1 is treated with different phosphonic acids or phosphonic acid esters in different concentrations, based on the amounts of calcium carbonate. 300 parts of the calcium carbonate thus treated are mixed with 700 parts of the same polyethylene and the mixture is processed as described in Example 1. The properties of the test specimens are listed in Table II.
  • Example 15 is repeated, except that 3 parts of dodecanephosphonic acid are used instead of octanephosphonic acid to modify the calcium carbonate.
  • the properties of the test specimens are listed in Table III.
  • a solution of 5 parts of octadecanephosphonic acid in 50 parts of acetone is added in 30 minutes in a high-speed mixer from an atomizer to 500 parts of calcium carbonate of calcite type with an average particle diameter of 5 ⁇ m and a specific surface area (BET) of 1 m 2 / g 1,200 rpm sprayed.
  • BET specific surface area
  • Example 17 is repeated, except that 5 parts of vinylphosphonic acid bis (2-ethylhexyl) ester are used without solvent instead of octadecanephosphonic acid.
  • the mixture is further processed as described in Example 1.
  • the properties of the test specimens are listed in Table III.
  • Example 17 is repeated, except that 10 parts of vinylphosphonic acid are used instead of octadecanephosphonic acid become.
  • the mixture is further processed as described in Example 1.
  • the properties of the test specimens are listed in Table III.
  • a mixture of untreated calcium carbonate and polyethylene is produced in accordance with Example 15.
  • a comparison sample with unmodified, precipitated calcium carbonate is also produced here.
  • Example 21 is repeated with the proviso that instead of acetone, methanol is used as the solvent and octanephosphonic acid is used as the modifier for precipitated calcium carbonate instead of vinylphosphonic acid.
  • methanol is used as the solvent
  • octanephosphonic acid is used as the modifier for precipitated calcium carbonate instead of vinylphosphonic acid.
  • the mixture is further processed as described in Example 1.
  • the properties of the test specimens are listed in Table V.
  • Example 23 is repeated, an additional 0.04 part of tert-butylhydroxyperoxide being added in the high-speed mixer.
  • the mixture is further processed as described in Example 1.
  • the properties of the test specimens are listed in Table V.
  • 1,050 parts of the polyethylene treated in this way are mixed well in a plow blade mixer with 450 parts of calcium carbonate (average particle diameter 5 ⁇ m, specific surface area 1 m 2 / g).
  • the mixture is further processed as described in Example 1.
  • the properties of the test specimens are listed in Table V.
  • Example 25 is repeated with the change that dodecanephosphonic acid is used instead of octanephosphonic acid.
  • the properties of the test specimens are listed in Table V.
  • Example 1 1,050 parts of polyethylene (density 0.96 g / cm 3 , melt index 23 g / 10 min., Stabilized as in Example 1), 450 parts of calcium carbonate (average particle diameter 5 ⁇ m, specific surface area 1 m 2 / g) and 4.5 parts Oetanephosphonic acid are mixed at 80 ° C in a high-speed mixer for 30 minutes. The extrusion and testing are carried out as described in Example 1.
  • test specimens are examined for impact strength. The results are shown in Table VI.
  • test specimens are produced and tested as described in Example 1.
  • test specimens are produced and examined as described in Example 1.
  • the same polyethylene is mixed with further amounts of the same calcium carbonate, which was modified with 1 percent by weight octanephosphonic acid, based on the amount by weight of filler, and processed further.
  • mixtures with untreated calcium carbonate are produced as a comparison.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
EP78100497A 1977-08-04 1978-07-25 Masses à mouler contenant une polyoléfine et un carbonate alcalino-terreux ainsi que leur préparation Expired EP0000726B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19772735160 DE2735160A1 (de) 1977-08-04 1977-08-04 Fuellstoff enthaltende kunststoff- formmasse
DE2735160 1977-08-04

Publications (2)

Publication Number Publication Date
EP0000726A1 true EP0000726A1 (fr) 1979-02-21
EP0000726B1 EP0000726B1 (fr) 1981-07-22

Family

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EP78100497A Expired EP0000726B1 (fr) 1977-08-04 1978-07-25 Masses à mouler contenant une polyoléfine et un carbonate alcalino-terreux ainsi que leur préparation

Country Status (8)

Country Link
US (1) US4174340A (fr)
EP (1) EP0000726B1 (fr)
JP (1) JPS5428349A (fr)
AU (1) AU518651B2 (fr)
CA (1) CA1115444A (fr)
DE (2) DE2735160A1 (fr)
IT (1) IT1097922B (fr)
ZA (1) ZA784405B (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0013142A1 (fr) * 1978-12-29 1980-07-09 Stauffer Chemical Company Charge inorganique à base d'un pyrophosphate contenant des groupes hydrocarbyle saturés; compositions de polymères contenant une telle charge et procédé de préparation de ces compositions
EP0171513A1 (fr) * 1984-08-16 1986-02-19 QUANTUM CHEMICAL CORPORATION (a Virginia corp.) Compositions de poly-oléfines résistantes au choc
FR2602236A1 (fr) * 1986-07-30 1988-02-05 Pluss Stauffer Ag Compositions thermoplastiques a tres haute teneur en matieres minerales pulverulentes pour incorporation dans les polymeres
EP0290871A1 (fr) * 1987-05-11 1988-11-17 Tetra Alfa Holdings S.A. Résine thermoplastique modifiée comme couvercle, son procédé de préparation et un couvercle de bouteille
EP0707051A1 (fr) * 1994-10-14 1996-04-17 Tioxide Group Services Limited Particules inorganiques revêtues d'un acide alkylphosphonique ou d'un ester de celui-ci, leur préparation et leur utilisation

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4274995A (en) * 1979-12-31 1981-06-23 Stauffer Chemical Company Filled polyolefin compositions having improved thermal stability
US4309333A (en) * 1979-12-31 1982-01-05 Stauffer Chemical Company Filled polyolefin compositions and filler material
US4359343A (en) * 1979-12-31 1982-11-16 Stauffer Chemical Company Filled polyolefin compositions and filler material
US4294752A (en) * 1980-01-14 1981-10-13 Stauffer Chemical Company Filled vinyl chloride polymer composition
US4328041A (en) * 1980-06-09 1982-05-04 Milliken Research Corporation Comminuted inorganic materials
DE3151814A1 (de) * 1981-12-29 1983-07-07 Hoechst Ag, 6230 Frankfurt "fuellstoff enthaltende kunststoff-formmasse, verfahren zu ihrer herstellung sowie deren verwendung"
ZA88101B (en) * 1987-02-06 1989-09-27 Minnesota Mining & Mfg Organo-phosphorous energy transfer agents
JPH0354233A (ja) * 1989-04-19 1991-03-08 Furukawa Electric Co Ltd:The 複合難燃剤およびそれを含有する難燃性樹脂組成物
EP0492463B1 (fr) * 1990-12-21 1995-09-27 Sumitomo Chemical Company Limited Composition de résine polyoléfinique
FR2742446B1 (fr) 1995-12-14 1999-01-15 Coatex Sa Utilisation de copolymeres de styrene et d'anhydride maleique comme agents dispersants et/ou de traitement de charges minerales. compositions thermoplastiques les contenant
US5948492A (en) 1997-01-09 1999-09-07 Graham Packaging Company, L.P. Cost-effective environmentally-friendly blow-molded plastic container
US6765041B1 (en) * 2000-11-27 2004-07-20 Millenium Inorganic Chemicals, Inc. Organo-acid phosphate treated pigments
US20080127497A1 (en) * 2005-10-31 2008-06-05 Dennis Moss Blade assembly
US8631583B2 (en) 2005-10-31 2014-01-21 Dennis Moss Bagel slicer
US9556322B2 (en) 2013-08-13 2017-01-31 Colormatrix Holdings, Inc. Liquid pigment dispersions
JP7743538B2 (ja) * 2021-04-22 2025-09-24 ミリケン・アンド・カンパニー ポリプロピレンポリマー組成物およびそれから作製された物品
US12559609B2 (en) 2021-04-22 2026-02-24 Milliken & Company Polyethylene polymer compositions and articles made from the same

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2027141A1 (fr) * 1968-12-26 1970-09-25 Du Pont
FR2028542A1 (fr) * 1969-01-17 1970-10-09 Phillips Petroleum Co
FR2268048A1 (fr) * 1974-04-19 1975-11-14 Unifos Kemi Ab

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2516168A (en) * 1947-10-17 1950-07-25 Victor Chemical Works Aryl and alkyl alkenylphosphonates
US3023180A (en) * 1959-08-17 1962-02-27 Phillips Petroleum Co Vulcanizable halogenated polyethylene compositions containing phosphorus
NL282628A (fr) * 1961-03-15
US3362924A (en) * 1966-08-04 1968-01-09 Warren O. Eastman Curable compositions comprising polyethylene, peroxide and particulate calcium carbonate coated with calcium stearate
US3272772A (en) * 1961-08-30 1966-09-13 Dow Chemical Co Filled polymer compositions
US3370029A (en) * 1966-03-14 1968-02-20 American Cyanamid Co Flame-retardant compositions for plastics

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2027141A1 (fr) * 1968-12-26 1970-09-25 Du Pont
FR2028542A1 (fr) * 1969-01-17 1970-10-09 Phillips Petroleum Co
FR2268048A1 (fr) * 1974-04-19 1975-11-14 Unifos Kemi Ab

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0013142A1 (fr) * 1978-12-29 1980-07-09 Stauffer Chemical Company Charge inorganique à base d'un pyrophosphate contenant des groupes hydrocarbyle saturés; compositions de polymères contenant une telle charge et procédé de préparation de ces compositions
EP0171513A1 (fr) * 1984-08-16 1986-02-19 QUANTUM CHEMICAL CORPORATION (a Virginia corp.) Compositions de poly-oléfines résistantes au choc
FR2602236A1 (fr) * 1986-07-30 1988-02-05 Pluss Stauffer Ag Compositions thermoplastiques a tres haute teneur en matieres minerales pulverulentes pour incorporation dans les polymeres
EP0258154A1 (fr) * 1986-07-30 1988-03-02 Pluess Staufer Ag Compositions thermoplastiques à très haute teneur en matières minérales pulvérulentes pour incorporation dans les polymères
EP0290871A1 (fr) * 1987-05-11 1988-11-17 Tetra Alfa Holdings S.A. Résine thermoplastique modifiée comme couvercle, son procédé de préparation et un couvercle de bouteille
EP0707051A1 (fr) * 1994-10-14 1996-04-17 Tioxide Group Services Limited Particules inorganiques revêtues d'un acide alkylphosphonique ou d'un ester de celui-ci, leur préparation et leur utilisation

Also Published As

Publication number Publication date
EP0000726B1 (fr) 1981-07-22
IT1097922B (it) 1985-08-31
DE2735160A1 (de) 1979-02-22
ZA784405B (en) 1979-08-29
CA1115444A (fr) 1981-12-29
US4174340A (en) 1979-11-13
DE2860857D1 (en) 1981-10-29
IT7826423A0 (it) 1978-08-02
JPS5428349A (en) 1979-03-02
AU3861278A (en) 1980-02-07
AU518651B2 (en) 1981-10-15

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