WO2004024818A1 - Compositions a base de polyoxymethylene contenant des pieges a formaldehyde selectionnes et utilisation de ceux-ci - Google Patents

Compositions a base de polyoxymethylene contenant des pieges a formaldehyde selectionnes et utilisation de ceux-ci Download PDF

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Publication number
WO2004024818A1
WO2004024818A1 PCT/EP2003/009076 EP0309076W WO2004024818A1 WO 2004024818 A1 WO2004024818 A1 WO 2004024818A1 EP 0309076 W EP0309076 W EP 0309076W WO 2004024818 A1 WO2004024818 A1 WO 2004024818A1
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formula
radical
compositions according
radicals
integer
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PCT/EP2003/009076
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German (de)
English (en)
Inventor
Stefan Wulf
Dirk Zierer
Klaus Kurz
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Ticona Gmbh
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Priority to AU2003264058A priority Critical patent/AU2003264058A1/en
Publication of WO2004024818A1 publication Critical patent/WO2004024818A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L59/00—Compositions of polyacetals; Compositions of derivatives of polyacetals
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3206—Polyhydroxy compounds aliphatic
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4833—Polyethers containing oxyethylene units
    • 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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3477—Six-membered rings
    • C08K5/3492—Triazines
    • C08K5/34922—Melamine; Derivatives thereof

Definitions

  • the present invention relates to new polyoxymethylene molding compositions and selected formaldehyde scavengers.
  • Polyoxymethylene compositions release small amounts of formaldehyde. This can be dissolved formaldehyde, which outgasses from the melt and the hot moldings, or it can be formaldehyde, which was formed when the composition was heated by being split off from the polymer.
  • Formaldehyde scavengers containing 2,4-diamothazinyl groups have also become known. Such compounds are described in EP-A-202,530. These include condensates of 4,6-diamino-1,3,5-triazine with short-chain polyaminoalkylenes. Other compounds containing amino groups have also already been used as formaldehyde scavengers in polyoxymethylene molding compositions, for example aminopyridines, guanamines or allantoin.
  • the efficiency of the formaldehyde scavengers depends, among other things, on the amount of additives that are mixed into the molding compositions. In principle, therefore, the highest possible amount of these additives is sought. However, high amounts of additives can impair the processing properties of the molding compositions or lead to a deterioration in the quality of the products produced, for example as a result of the increased formation of mold coatings.
  • the present invention provides amino functionalities with suitable basicities for polyoxymethylene molding compositions, so that the formaldehyde emission can be significantly reduced without other disadvantages for the polymer, such as yellowing, or for its processing, such as the formation of moldings, in purchase to have to take.
  • selected formaldehyde scavengers were reacted with and reacted with selected isocyanate group-containing reagents
  • compositions comprising at least one polyoxymethylene homo- and / or copolymer and at least one compound of the formula I.
  • R 1 is the divalent to hexavalent radical of an alcohol or amine
  • X is -O- or -NR 2 -
  • R 2 is hydrogen, alkyl, cycloalkyl, aryl or aralkyl
  • R 3 is alkylene, cycloalkylene, arylene or aralkylene
  • R 4 is a radical which is selected from the radicals of the formulas II, III, IV, V, VI and VII
  • R 5 is hydrogen, -CO-CH 3 or -CO-C 6 H 5 , o is an integer between 2 and 6 and p is 1 or 2. If any radicals are alkyl, these are generally saturated alkyl radicals having one to twenty carbon atoms. The alkyl radicals can be straight-chain or branched.
  • the alkyl radicals can also carry inert substituents, for example alkoxy radicals with preferably one to six carbon atoms, or halogen atoms, such as chlorine.
  • radicals are cycloalkyl, these are generally saturated cycloalkyl radicals having five to eight, preferably five or six, ring carbon atoms.
  • the cycloalkyl radicals can also carry inert substituents, for example alkyl or alkoxy radicals with preferably one to six carbon atoms, or halogen atoms, such as chlorine.
  • Cyclopentyl or cyclohexyl are preferred.
  • radicals are aryl, these are generally aromatic hydrocarbon radicals with one or two aromatic nuclei, which may also have one or two ring heteroatoms, such as nitrogen, sulfur or
  • the aryl radicals can also carry inert substituents, for example alkyl or alkoxy radicals having preferably one to six carbon atoms, or halogen atoms, such as chlorine.
  • Phenyl is preferred. If any radicals are aralkyl, these are generally aromatic hydrocarbon radicals with one or two aromatic nuclei which also have an alkylene chain.
  • the aralkyl radicals can also carry inert substituents, for example alkyl or alkoxy radicals with preferably one to six carbon atoms, or halogen atoms, such as chlorine.
  • Preferred radicals R 2 are methyl or preferably hydrogen.
  • alkylene these are generally saturated alkylene residues with two to twenty carbon atoms.
  • the alkylene radicals can be straight-chain or branched.
  • the alkylene radicals can also carry inert substituents, for example alkoxy radicals with preferably one to six carbon atoms, or halogen atoms, such as chlorine.
  • Alkylene radicals with two to six are preferred. Ethylene is particularly preferred.
  • Any cycloalkylene radicals are generally saturated cycloalkylene radicals having five to eight, preferably five or six
  • the cycloalkylene radicals can also carry inert substituents, for example alkyl or alkoxy radicals with preferably one to six carbon atoms, or halogen atoms, such as chlorine.
  • Cyclopentylene or cyclohexylene are preferred. If any radicals are arylene, these are generally aromatic hydrocarbon radicals having one or two aromatic nuclei, which may also have one or two ring heteroatoms, such as nitrogen, sulfur or oxygen.
  • the arylene radicals can also carry inert substituents, for example alkyl or alkoxy radicals with preferably one to six carbon atoms, or halogen atoms, such as chlorine.
  • phenylene especially 1, 3- and 1, 4-phenylene, biphen-4,4'-diyl,
  • radicals mean aralkylene, these are generally aromatic hydrocarbon radicals with one or two aromatic nuclei which also have an alkylene chain.
  • the aralkylene radicals can also carry inert substituents, for example alkyl or alkoxy radicals with preferably one to six carbon atoms, or halogen atoms, such as chlorine.
  • R 1 is the di- to hexavalent residue of an alcohol or amine after removal of the alcohol or amino groups. These can be low molecular weight or also oligomeric or polymeric compounds.
  • compositions in which R 1 is a radical of the formula —CnH 2 n-, in which n is an integer from 2 to 4, phenylene, trimethylolpropane without the three hydroxyl groups, pentaerythritol without the four hydroxyl groups, or a sugar without the six hydroxyl groups ,
  • oligomeric or polymeric residues R 1 are residues of a polyether, polyester, polyamide, polyacrylate, polyolefin, polysiloxane or polycarbonate having di- to tetravalent hydroxyl or amino end groups after the end groups have been removed.
  • radicals of a polyether or polyester which have di- to tetravalent hydroxyl or amino end groups after the end groups have been removed and which have the recurring structural units of the formulas VIII, IX, X or XI
  • R 6 , R 8 and R 9 independently of one another are alkylene, cycloalkylene, arylene or aralkylene,
  • R 7 and R 10 are residues of a di to tetravalent aliphatic, cycloaliphatic, aromatic or araliphatic alcohol, x and y are integers from 1 to 200, and p is an integer from 2 to 4.
  • R 6 and R 8 are very particularly preferably radicals of the formula -CH 2 -CH 2 -, -CH (CH 3 ) - CH- or -CH 2 -CH2-CH2-CH2-, R 9 is a radical of the formula -C m H 2 m-, where m is an integer from 2 to 6, or a phenylene radical, and R 7 and R 10 are radicals of
  • X is -NH- or in particular -O-.
  • compositions according to the invention contain structural units R 3 which are derived from a diisocyanate. Any diisocyanates can be used.
  • Preferred radicals are R 3 , the radicals of the formula -C P H2 P -, in which p is an integer from 2 to 18, or a divalent radical of a cycloalkylene having five to eight ring carbon atoms, a phenylene or naphthylene radical, where these radicals can have one to four substituents which are selected from the group consisting of alkyl, alkoxy, cycloalkyl, cycloalkyloxy, aryl and aryloxy.
  • compositions in which R 3 is a divalent one are very particularly preferred
  • Rest is derived from 4-methylpentane, 5-methylhexane, 1-methylcyclohexane, 6-methylheptane, 2,2,5-trimethylheptane, 3,7-dimethyloctane, 1, 2,2-trimethylcyclopentane, 1, 4- or 1, 3-Dimethylcyclohexane, toluene, biphenyl, diphenylmethane, dicyclohexyimethane, isophorone and hexane.
  • compositions in which R 4 is a radical of the formula V or in particular the formula II and which preferably have recurring structural units of the formulas VIII, IX, X or XI, in which x or y are integers from 8 to 15, are particularly preferred.
  • compositions in which o is 2 are further preferred.
  • the invention also relates to selected and new compounds of the formula I in which X, R 1 , R 2 , R 3 , R 4 , R 5 and o have the meanings defined above, with the proviso that when R 4 is a radical of the formula II, III, IV, VI or VII, R 1 is the radical of a polyether or polyester having di- to tetravalent hydroxyl or amino end groups after removal of the end groups, which is the repeating structural units of the formulas VIII, IX, X or XI defined above and where the indices x, y and p assume values such that the compound of the formula I has a molecular weight of at least 800, preferably at least 800 to 5,000, particularly preferably from 850 to 2,200.
  • the invention furthermore relates to the use of the compound of the formula I for reducing the formaldehyde emission of polyoxymethylene homo- or copolymers.
  • the compounds of the formula I used according to the invention can be obtained by processes known per se by reacting dihydric alcohols or amines of the formula XII with diisocyanates of the formula XIII and then capping the free isocyanate groups of the resulting adduct with amines of the formula XIV
  • R 1 , R 3 , R 4 , X and o have the meaning defined above.
  • the compounds of the formulas XII and XIII are used in such an amount that the free alcohol or amino groups of the compound of the formula XII are in each case blocked by an isocyanate group of the compound of the formula XIII and only one isocyanate group of the
  • Diisocyanate XIII reacted.
  • diisocyanate XIII and / or a diisocyanate XIII with two differently reactive isocyanate groups polymeric adducts can be prevented from forming.
  • the reaction is typically carried out in an organic solvent, for example in dipolar aprotic solvents, such as DMSO, or in aromatic hydrocarbons, such as toluene or xylene, which are liquid at reaction temperatures.
  • organic solvent for example in dipolar aprotic solvents, such as DMSO, or in aromatic hydrocarbons, such as toluene or xylene, which are liquid at reaction temperatures.
  • the reaction temperatures are usually 0 to 220 ° C, preferably 30 to 150 ° C.
  • the first stage of the reaction usually takes place at lower temperatures, for example at 0 to 50 ° C.
  • the second stage of the reaction usually takes place at higher temperatures, for example at 50 to 150 ° C. It is of course also possible to carry out both reaction stages at the same temperature.
  • adducts containing isocyanate groups are then reacted in a second step with an amine XIV or a mixture of such amines. This is advantageously done without isolating the intermediate of formula XV
  • R 1 , R 3 , X and o have the meaning defined above.
  • This reaction also takes place in an organic solvent. Examples of this are listed above.
  • the polyoxymethylenes (POM), as described, for example, in DE-A 29 47 490, are generally unbranched linear polymers, which are generally at least 80%, preferably at least 90%,
  • polyoxymethylene Contain oxymethylene units (-CH2-O-).
  • polyoxymethylene includes both homopolymers of formaldehyde or its cyclic oligomers, such as trioxane or tetroxane, as well as corresponding copolymers.
  • Homopolymers of formaldehyde or trioxane are those polymers whose
  • Hydroxyl end groups are chemically stabilized against degradation in a known manner, e.g. B. by esterification or by etherification.
  • Copolymers are polymers of formaldehyde or its cyclic oligomers, especially trioxane, and cyclic ethers, cyclic acetals and / or linear polyacetals.
  • these polymers have at least 50 mol% of recurring units -CH2-O- in the main polymer chain.
  • the homopolymers are generally prepared by polymerizing formaldehyde or trioxane, preferably in the presence of suitable catalysts.
  • POM copolymers are preferred, in particular those which, in addition to the repeating units -CH 2 -O-, also contain up to 50, preferably from 0.1 to 20 and in particular 0.5 to 10 mol% of repeating units
  • R to R independently of one another are a hydrogen atom, a Cr to C 4 alkyl group or a halogen-substituted alkyl group having 1 to 4 C atoms and R 15 is a -CH2-, -O-CH 2 -, ad- to C 4 alkyl or C 4 to C - represent 4-substituted methylene group or a corresponding oxymethylene group, and n has a value in the range of 0 has up. 3
  • cyclic ethers are those of the formula
  • Examples include ethylene oxide, 1,2-propylene oxide, 1,2-butylene oxide,
  • Copolymers of 99.5-95 mol% of trioxane and 0.5 to 5 mol% of one of the aforementioned comonomers are used particularly advantageously.
  • polyoxymethylenes are oxymethylene terpolymers which, for example, by reacting trioxane, one of the cyclic ethers described above and with a third monomer, preferably a bifunctional compound of the formula
  • Preferred monomers of this type are ethylene diglycide, diglycidyl ether and diether from glycidylene and formaldehyde, dioxane or trioxane in a molar ratio of 2: 1, and diether from 2 mol of glycidyl compound and 1 mol of an aliphatic diol having 2 to 8 carbon atoms, such as, for example, the diglycidyl ether of ethylene glycol , 1, 4-butanediol, 1,3-butanediol, cyclobutane-1,3-diol, 1,2-propanediol and cyclohexane-1,4-diol, to name just a few examples.
  • the preferred POM copolymers have melting points of at least 150 ° C. and molecular weights (weight average) M w in the range from 5,000 to 200,000, preferably from 7,000 to 150,000.
  • End-group stabilized POM polymers which have C-C bonds or the methoxy end groups at the chain ends are particularly preferred.
  • the used POM-polymers generally have a melt index (MVR value 190/2, 16) of 2 to 50 cm 3/10 min (ISO 1 133).
  • compositions according to the invention usually contain 75 to 99.99% by weight, preferably 80 to 99.8% by weight, of POM homo- or copolymer and 0.01 to 5% by weight, preferably 0.2 to 0.5% by weight. % of compounds of the formulas I, these details relating in each case to the overall composition.
  • compositions according to the invention also contain other additives known per se.
  • processing aids such as antioxidants, acid scavengers and others
  • Formaldehyde scavengers UV stabilizers, adhesion promoters, lubricants, nucleating agents or mold release agents; Fillers, such as glass balls, calcium carbonate, talc, wollastonite or silicon dioxide; Reinforcement materials such as carbon fibers, aramid fibers or glass fibers; Antistatic agents or additives which impart a desired property to the molding composition, such as dyes and / or pigments and / or
  • Impact modifiers and / or additives which impart electrical conductivity for example carbon black or metal particles, and mixtures of these additives, but without restricting the scope to the examples mentioned.
  • the proportion of these additives in the compositions according to the invention is usually 0.2 to 30% by weight, preferably 0.5 to 25% by weight, based on the total composition.
  • antioxidants are phenolic compounds, such as N, N'-bis-3- (3 ', 5'-di-tert-butyl-4 ' -hydroxyphenyl) propionylhydrazine, 1, 6-hexanediol-bis-3- (3rd ', 5' -di- tert-butyl-4 'hydroxyphenyl) propionate, 3,6-dioxaoctane-1, 8-diol-bis-3- [3' -t-butyl-4 '- hydroxy-5' - (methylphenyl)] propionate, N, N ' -hexamethylene-bis-3- (3 ' , 5 ' -di-tert.butyl- 4 ' -hydroxyphenyl) propionamide, tetrakis [methylene-3- (3 ' , 5 '-di-tert-butyl-4'-hydroxyphenyl) propionyl)] methane and 1, 3,5
  • lubricants are esters and amides of a long-chain aliphatic carboxylic acid and an aliphatic alcohol, or polyethylene waxes, preferably oxidized polyethylene waxes.
  • additives which give the molding composition a desired property are ultra-high molecular weight polyethylene (PE-UHMW), polytetrafluoroethylene (PTFE) and graft copolymers which are a product of a grafting reaction from an olefin
  • impact modifiers are polyurethanes with elastomeric properties or other elastomers.
  • the polyol was dissolved in DMSO.
  • a solution of isophorone diisocyanate in DMSO was added dropwise at room temperature. After the addition, 5-10 drops were left of dibutyltin dilaurate was added and the reaction solution was stirred at room temperature for about 6 hours. After this, melamine was added and the reaction was stirred at 150 ° C. overnight.
  • the DMSO was separated off by distillation, the product was dried to constant weight at 120 ° C. and then finely ground.
  • the stabilizers thus produced were mixed in different concentrations in a POM with an MVR of 9 ml / 10 min and compared against melamine in their acceptor properties.
  • other stabilizers were present (lubricants, oxidation stabilizers, acid scavengers), the type and amount of which were kept constant in all experiments.
  • the formaldehyde emission was measured using the VDA 275 test. The results are shown in the table below. table

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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)

Abstract

L'invention concerne des matières à mouler à base de polyoxyméthylène, ces matières contenant des composés de formule (I) R1-[X-CO-NH-R3-NH-CO-NR2-R4]o, dans laquelle R1 à R3, X et o ont les significations indiquées dans la revendication 1. Ces composés de formule (I) sont adaptés en tant que pièges à formaldéhyde dans des matières à mouler à base de polyoxyméthylène.
PCT/EP2003/009076 2002-08-29 2003-08-16 Compositions a base de polyoxymethylene contenant des pieges a formaldehyde selectionnes et utilisation de ceux-ci WO2004024818A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003264058A AU2003264058A1 (en) 2002-08-29 2003-08-16 Polyoxymethylene compositions containing selected formaldehyde scavengers and the use thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2002139697 DE10239697B4 (de) 2002-08-29 2002-08-29 Polyoxymethylen Formmassen mit ausgewählten Formaldheydfängern und deren Verwendung
DE10239697.3 2002-08-29

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Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102005022364A1 (de) * 2005-05-10 2006-11-23 Basf Ag Verwendung von Polyethyleniminen zur Verminderung des Formaldehyd-Restgehalts in Polyoxymethylenen

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4136092A (en) * 1975-06-09 1979-01-23 Thiokol Corporation Polyurethane curing agents
EP0350223A2 (fr) * 1988-07-04 1990-01-10 Polyplastics Co. Ltd. Composition de résine de polyacétal
EP0632097A1 (fr) * 1993-01-20 1995-01-04 Asahi Kasei Kogyo Kabushiki Kaisha Composition de resine polyoxymethylenique
EP0755973A1 (fr) * 1995-07-25 1997-01-29 Basf Aktiengesellschaft Composition de polyoxyméthylène résistant aux chocs
EP1031589A1 (fr) * 1999-02-25 2000-08-30 Dsm N.V. Composé supramoléculaire

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR940002986B1 (ko) * 1989-11-28 1994-04-09 아사히 가세이 고오교 가부시끼가이샤 내마모성 폴리옥시메틸렌 수지 조성물 및 이의 제조방법
DE4236465A1 (de) * 1992-10-24 1994-04-28 Degussa Polyoxymethylen mit verbesserter Stabilität gegen Säuren, Verfahren zu seiner Herstellung sowie Verwendung

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4136092A (en) * 1975-06-09 1979-01-23 Thiokol Corporation Polyurethane curing agents
EP0350223A2 (fr) * 1988-07-04 1990-01-10 Polyplastics Co. Ltd. Composition de résine de polyacétal
EP0632097A1 (fr) * 1993-01-20 1995-01-04 Asahi Kasei Kogyo Kabushiki Kaisha Composition de resine polyoxymethylenique
EP0755973A1 (fr) * 1995-07-25 1997-01-29 Basf Aktiengesellschaft Composition de polyoxyméthylène résistant aux chocs
EP1031589A1 (fr) * 1999-02-25 2000-08-30 Dsm N.V. Composé supramoléculaire

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DE10239697A1 (de) 2004-03-18
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