EP1836248A1 - Composition polymere a equipement antistatique, son mode de production et son utilisation - Google Patents

Composition polymere a equipement antistatique, son mode de production et son utilisation

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Publication number
EP1836248A1
EP1836248A1 EP05846583A EP05846583A EP1836248A1 EP 1836248 A1 EP1836248 A1 EP 1836248A1 EP 05846583 A EP05846583 A EP 05846583A EP 05846583 A EP05846583 A EP 05846583A EP 1836248 A1 EP1836248 A1 EP 1836248A1
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EP
European Patent Office
Prior art keywords
polymer composition
acid
composition according
mixture
aminoalcohol
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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.)
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EP05846583A
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German (de)
English (en)
Inventor
Stefan Fokken
Hans-Jürgen Sander
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Baerlocher GmbH
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Baerlocher GmbH
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Publication of EP1836248A1 publication Critical patent/EP1836248A1/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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/16—Halogen-containing compounds
    • 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
    • C08K5/17—Amines; Quaternary ammonium compounds
    • 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
    • C08K5/0075—Antistatics

Definitions

  • Antistatic polymer composition their preparation and
  • the present invention relates to an antistatic polymer composition, its preparation and its use.
  • halogen-containing plastics tend to undergo undesired decomposition and degradation reactions during thermal stress during processing or in long-term use.
  • hydrochloric acid is formed, which is eliminated from the polymer strand, resulting in a discolored, unsaturated plastic with coloring Polyensequenzen.
  • a particular problematic aspect is that halogen-containing polymers only have the theological conditions required for processing at a relatively high processing temperature. At such temperatures, however, a noticeable decomposition of the polymer already occurs in the case of unstabilized polymers, which leads to both the undesired color change described above and to a change in the material properties.
  • the hydrochloric acid released from unstabilized halogen-containing polymers at such a processing temperature can lead to significant corrosion of the processing equipment.
  • This process plays a role in particular when production interruptions occur during the processing of such halogenated polymers into shaped articles, for example by extrusion, and the polymer composition lingers in the extruder for a relatively long period of time. During this time, the above-mentioned decomposition reactions may occur, making the batch in the extruder unusable, and possibly damaging the extruder.
  • polymers that undergo such decomposition tend to form cling to the processing equipment that is difficult to remove.
  • halogen-containing polymers for processing are usually added as so-called stabilizers compounds which should as far as possible prevent the abovementioned decomposition reactions.
  • stabilizers are solids which are added to the polymer to be processed before it is processed.
  • the moldings may have electrostatically unfavorable properties.
  • antistatics are therefore often added to the polymers. With the help of such antistatic agents, the tendency of polymers to load under mechanical stress, in particular friction, counteracted, or the rapid flow of the charge is ensured.
  • polymers are therefore frequently added with carbon blacks, PEG esters, glycerol mono- or distearates or, for example, also inorganic perchlorate compounds. While the former compounds often lacked in their antistatic effect, the perchlorates were usually intended for use in polymer compositions which serve to stabilize plastics.
  • a further object of the present invention is to provide a polymer composition which leads to an improvement in the discharge behavior.
  • a further object of the present invention is to provide a polymer composition which has a suitable discharge behavior of the polymeric end product and which has little or no turbidity in the case of transparent end products, for example of hard or soft PVC.
  • a further object of the invention was to provide a polymer composition which, on the one hand, gives the end product a good discharge characteristic and, moreover, has better heat stability.
  • a first subject of the invention is therefore a polymer composition
  • a polymer composition comprising the following components: a) at least one halogen-containing polymer, b) at least one organic ammonium salt of a perchlorate or a mixture of two or more organic ammonium salts of perchlorates and c) at least one aminoalcohol with 2 to 12 C atoms in the alcohol radical, wherein the melting point of the amino alcohol 80 0 C or less.
  • a "polymer composition” is understood as meaning a composition which contains at least one stabilizer composition which is suitable for stabilizing halogen-containing polymers and moreover positively influences the discharge behavior of these halogen-containing polymers.
  • a corresponding stabilizer composition is generally mixed with a halogen-containing polymer intended for stabilization and then processed to give a polymer composition.
  • a stabilizer composition it is also possible to add a stabilizer composition to the halogen-containing polymer to be stabilized during processing. In either case, the improved discharge characteristic from the addition occurs, it continues to act in the processed polymer.
  • liquid in the context of the present invention, the physical state of a stabilizer composition of the invention at least over a temperature range of about 45 to 100 0 C, preferably over a temperature range of about 30 to about 12O 0 C, more preferably over a temperature range of about 15 to about 15O 0 C or more preferably over a temperature range of about 0 to about 200 0 C understood.
  • ammonium salt is an organic ammonium salt. This means that the ammonium group of the onium salt carries at least one organic radical.
  • An ammonium salt according to the present invention may, depending on the nature of the ammonium group, carry 1, 2, 3 or 4 organic radicals.
  • An ammonium perchlorate which can be used in the context of the present invention has at least one positively charged N atom or two or more such positively charged N atoms.
  • ammonium perchlorates used are compounds which have at least one organic radical on the N atom and
  • an ammonium perchlorate which can be used according to the invention carries fewer organic radicals than necessary for the formation of a positively charged ammonium ion, the positive charge is generated in a conventional manner known to those skilled in the art by protonation by means of a suitable acid, such that the corresponding ammonium perchlorate is present in this case organic residue still carries at least one proton.
  • compounds can therefore be used as ammonium perchlorates which have a positive charge due to protonation reactions.
  • ammonium perchlorates which have a positive charge due to a peralkylation reaction.
  • examples of such compounds are tetraalkylammonium perchlorates.
  • a peralkylated ammonium perchlorate which can be used according to the invention has an aryl, alkaryl, cycloalkyl, alkenyl, alkynyl or cycloalkenyl radical.
  • an ammonium salt which can be used in the context of a polymer composition according to the invention has two or optionally more different substituent types, for example an alkyl and a cycloalkyl radical or an alkyl radical and an aryl radical.
  • an ammonium salt which can be used in the context of a polymer composition according to the invention has substituents which in turn are substituted by one or more functional groups.
  • functional groups are meant groups which improve the properties of the polymer composition in terms of antistatic behavior and stabilization against heat during processing or in long-term use, or at least not or worsen only insignificantly.
  • Corresponding functional groups can be, for example, NH groups, NH 2 groups, OH groups, SH groups, ester groups, ether groups, thioether groups, isocyanurate groups or keto groups or mixtures of two or more thereof.
  • ammonium perchlorates it is possible in principle to use all compounds which lead to an ammonium perchlorate by appropriate reaction of suitable reactants.
  • ammonium perchlorates which can be used according to the invention can be obtained, for example, by appropriate reaction of amines or amides, such as alkylmonoamines, alkylenediamines, alkylpolyamines, secondary or tertiary amines or dialkylamines.
  • Suitable ammonium perchlorates are therefore derived, for example, from primary mono- or polyamino compounds having from 2 to about 40, for example from 6 to about 20, carbon atoms.
  • these are ethylamine, n-propylamine, i-propylamine, n-butylamine, sec-butylamine, tert-butylamine, substituted amines having 2 to about 20 C atoms, such as 2- (N, N-dimethylamino) -1 - aminoethane.
  • Suitable diamines have, for example, two primary, two secondary, two tertiary or one primary and one secondary or one primary and one tertiary or one secondary and one tertiary amino group.
  • diaminoethane the isomeric diaminopropanes, the isomeric diaminobutanes, the isomeric diaminohexanes, piperazine, 2,5-dimethylpiperazine, amino-3-aminomethyl-3,5,5-trimethylcyclohexane (isophoronediamine, IPDA), 4,4'-diamino dicyclohexylmethane, 1,4-diaminocyclohexane, aminoethylethanolamine, hydrazine, hydrazine hydrate or triamines, such as the diethylenetriamine or 1,8-diamino-4-aminomethyloctane or tertiary amines, such as triethylamine, tribut
  • ammonium perchlorate used is triethylammonium perchlorate or triisopropylammonium perchlorate or a mixture thereof.
  • At least one alkyl radical of an ammonium perchlorate used according to the invention has a polar substituent.
  • all polar substituents which, in the sense of the "functional groups" already mentioned above, improve or at least do not or only insignificantly impair the properties of the polymer composition with regard to antistatic behavior and heat stabilization during processing or long-term use are suitable.
  • Corresponding polar substituents may be, for example, NH groups, NH 2 groups, OH groups, SH groups, ester groups, ether groups, thioether groups, isocyanurate groups or keto groups or mixtures of two or more thereof.
  • ammonium perchlorates are used as constituent of a polymer composition according to the invention which have at least one OH group.
  • Suitable for preparing such ammonium perchlorates are, for example, aliphatic amino alcohols containing 2 to about 40, preferably 6 to about 20, carbon atoms, for example ethanolamine, propanolamine, butanolamine, diethanolamine, dipropanolamine, dibutanolamine, triethanolamine, tripropanolamine, tributanolamine, tripentanolamine, 1 -Amino-3,3-dimethyl-pentan-5-ol, 2-aminohexane 2 ', 2 "-diethanolamine, 1-amino-2,5-dimethylcyclohexan-4-ol, 2-aminopropanol, 2-aminobutanol, 3-aminopropanol, 1-amino-2-propanol, 2-amino-2-methyl -l-propanol, 5-aminopentanol, 3-aminomethyl-3,5,5-trimethylcyclohexanol, 1-amin
  • Amino-3-phenyl-l-propanol, 2-amino-1-phenylethanol, 2-phenylglycinol or 2-amino-l-phenyl-l, 3-propanediol and mixtures of two or more such compounds are used.
  • the perchlorates of heterocyclic compounds which have a cyclic ring system containing amino groups are used as ammonium perchlorates.
  • the perchlorates of heterocyclic amino alcohols are used which have at least 2, preferably at least 3, amino groups in the ring.
  • the trimerization products of isocyanates are particularly suitable as the central ring constituent of the ammonium perchlorates which can be used according to the invention.
  • Suitable examples include hydroxyl-containing isocyanurates of the general formula I.
  • Y and the indices m are each the same or different and m is an integer from 0 to 20 and Y is a hydrogen atom or a linear or branched, saturated or unsaturated alkyl group having 1 to about 10 C atoms.
  • TCEIC tris (hydroxymethyl) isocyanurate
  • ammonium perchlorates are, for example, compounds in which the amino group is bonded to a substituted aromatic or heteroaromatic system, for example aminobenzoic acid, aminosalicylic acid or aminopyridinecarboxylic acid and suitable derivatives thereof.
  • ammonium perchlorates for example, 2-Ethylcarboxypyridiniumperchlorat, Formamidiniumperchlorat, the perchlorate salt of Trishydroxyethylisocyanurats, the perchlorate salt of 2- (diethylamino) ethanol, N- (2-hydroxyethyl) - mo ⁇ holiniumperchlorat or Trioctylammoniumperchlorat or mixtures of two or more used.
  • ammonium perchlorates for example, 2-Ethylcarboxypyridiniumperchlorat, Formamidiniumperchlorat, the perchlorate salt of Trishydroxyethylisocyanurats, the perchlorate salt of 2- (diethylamino) ethanol, N- (2-hydroxyethyl) - mo ⁇ holiniumperchlorat or Trioctylammoniumperchlorat or mixtures of two or more used.
  • a polymer composition according to the invention may in the context of the present invention, for example, only one of the above Ammoniumperch- lorate included. It is also possible within the scope of the present invention and also provided for a polymer composition according to the invention to comprise a mixture of two or more of the abovementioned ammonium perchlorates. It may be a mixture of two or more different types of ammonium perchlorates.
  • a polymer composition according to the invention contains a mixture of two or more ammonium perchlorates, these two or more ammonium perchlorates may in principle be present in any desired ratio in the polymer composition according to the invention. It is preferred if at least one ammonium perchlorate has at least one alkyl radical having a polar substituent, for example an OH group. It is very particularly preferred if such an ammonium perchlorate makes up the largest amount of the ammonium perchlorates present in a polymer composition according to the invention in terms of quantity.
  • a polymer composition according to the invention contains 0.01 to about 5% by weight, for example about 0.05 to about 3% by weight, of an organic ammonium salt of a perchlorate or a mixture of two, based on the total composition or more organic ammonium salts of perchlorates.
  • a polymer composition according to the invention also contains at least one aminoalcohol having 2 to 12 C atoms in the alcohol radical, the melting point of the aminoalcohol being 80 ° C. or less.
  • the alcohol radical can basically have an aliphatic, cycloaliphatic or aromatic skeleton. If an amino alcohol present in accordance with the invention has two or more alcohol radicals, the corresponding alcohol radicals can be, for example, exclusively aliphatic or exclusively cycloaliphatic or exclusively aromatic. However, it is also possible according to the invention that corresponding alcohol residues are of mixed construction. For example, it is possible for an aminoalcohol usable in the context of the present invention to comprise a mixture of aliphatic and cycloaliphatic or a mixture of aliphatic and aromatic or a mixture of cycloaliphatic and aromatic alcohol radicals.
  • an amino alcohol which can be used according to the invention has three alcohol radicals, these may be, for example, of aliphatic, cycloaliphatic and aromatic nature. If an alcohol radical is an aliphatic alcohol radical, this may be linear or branched, saturated or unsaturated, but preferably saturated. Cycloaliphatic and aromatic alcohol radicals can be mono- or polycyclic and optionally have substituents such as alkyl groups, halogens or, in addition to an existing OH group or in addition to the OH groups present, other polar substituents.
  • Suitable amino alcohols have alcohol radicals having from 2 to about 12 carbon atoms. Suitable examples are amino alcohol with alcohol radicals having 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11 carbon atoms, for example from 2 to about 8 or 3 to about 6 carbon atoms.
  • a combination of a perchlorate and an aminoalcohol having a number of 2 to 12 carbon atoms in the alcohol radical and a melting point of less than 80 0 C in the processing of a polymer composition according to the invention allows an excellent distribution of the active ingredients within the polymer so that an unexpected increase in antistatic effect is achieved along with an improvement in heat stabilization.
  • suitable amino alcohols may have a melting point of up to about 70 or up to about 60 or up to about 50 ° C.
  • amino alcohols having a melting point below these values for example amino alcohols having a melting point of up to about 40, up to about 30, up to about 20 or up to about 10 ° C. or less, for example up to about 0, to about -10 or up to about -20 ° C.
  • a polymer composition according to the invention contains at least one aminoalcohol which is an alkanolamine.
  • Suitable amino alcohols are in principle aminomonoalcohols or aminodialcohols or aminotrialcohols or mixtures of two or more thereof, a polymer composition according to the invention being able to comprise, for example, an aminomonoalcohol or aminodialcohol or aminotrialcohol or a mixture of two or more thereof.
  • all amino alcohols are suitable as constituents of a polymer composition according to the invention which fulfill the abovementioned conditions with regard to the number of carbon atoms in the alcohol radical and of the melting point.
  • the aminoalcohol is a monoaminoalcohol.
  • Suitable alkanolamines are, for example, ethanolamine, propanolamine, butanolamine, diethanolamine, dipropanolamine, dibutanolamine, triethanolamine, tri-n-propanolamine, triisopropanolamine, tributanolamine, tripentanolamine, 1-amino-3,3-dimethylpentan-5-ol, 2 -Aminohexane-2 ', 2 "-diethanolamine, 1-amino-2,5-dimethylcyclohexan-4-ol, 2-aminopropanol, 2-aminobutanol, 3-aminopropanol, 1-amino-2-propanol, 2-amino 2-methyl-1-propanol, 5-aminopentanol, 3-aminomethyl-3,5,5-trimethylcyclohexanol, 1-amino-1-cyclopentan-methanol, 2-amino-2-ethyl-1,3
  • a composition according to the invention contains the abovementioned organic ammonium perchlorates and the abovementioned amino alcohols, for example in a ratio of about 100: 1 to about 1: 100. It is particularly advantageous in the context of the present invention, if the content of amino alcohol is only slightly lower than the content of organic perchlorate, about the same size as the content of organic perchlorate or even slightly or significantly exceeds this content. This is reflected, for example, in appropriate Ratios of ammonium perchlorate to aminoalcohol of from about 2: 1 to about 1:30 or about, 5: 1 to about 1:20, or about 1: 1 to about 1:10.
  • a polymer composition of the invention may further contain one or more solvents.
  • a “solvent” is understood as meaning a compound or a mixture of two or more compounds which is liquid within a certain temperature range and capable of producing an ammonium perchlorate present in a composition according to the invention or a mixture of two or more to dissolve such ammonium perchlorates.
  • a suitable solvent in the context of the present invention is at least within a temperature range of about 45 to about 100 0 C, preferably within a temperature range of about 30 to about 120 0 C or within a temperature range of about 15 to about 150 0 C and in particular within a Temperature range from about 0 to about 200 0 C liquid.
  • the term "within a temperature range of” refers in the context of the present text to the physical state of the solvent within the entire temperature range.
  • the solvents used are compounds or mixtures of two or more compounds which are suitable as plasticizers for halogen-containing polymers.
  • Suitable solvents for the purposes of the present text are therefore, for example, compounds from the group of phthalic esters such as dimethyl, diethyl, dibutyl, dihexyl, di-2-ethylhexyl, di-n-octyl, di-iso-octyl , Di-iso-nonyl, di-iso-decyl, dicyclohexyl, dimethylcyclohexyl, dimethyl glycol, dibutyl glycol, benzyl butyl or diphenyl phthalate and mixtures of phthalates, for example mixtures of alkyl phthalates having 7 to 9 or 9 to 11 C atoms in the ester alcohol or mixtures of alkyl phthalates having 6 to 10 and 8 to 10 C atoms in the ester alcohol.
  • Particularly suitable for the purposes of the present invention are dibutyl, dihexyl, di-2-ethylhexyl, di-n-octyl, di-iso-octyl, diiso-nonyl, di-iso-decyl, Di-iso-tridecyl- and Benzylbutylphthalat and the said mixtures of alkyl phthalates.
  • esters of aliphatic dicarboxylic acids in particular the esters of adipic, azelaic or sebacic acid or mixtures of two or more thereof.
  • examples of such solvents are di-2-ethylhexyl adipate, diisooctyl adipate, di-iso-nonyl adipate, diisodecyl adipate, benzyl butyl adipate, benzyloctyl adipate, di-2-ethylhexyl azelate, di-2-ethylhexyl sebacate and diisodecyl sebacate , Within the scope of a further embodiment of the present invention, preference is given to di-2-ethylhexyl acetate and diisoctyl adipate.
  • trimellitic esters such as tri-2-ethylhexyl trimellitate, triisopropyltrimellitate, triisoctyl trimellitate and trimellitic acid esters having 6 to 8, 6 to 10, 7 to 9 or 9 to 11 C atoms in the ester group or mixtures of two or more of said compounds.
  • solvents are, for example, polymer plasticizers, as described in "Kunststoffadditive", R. Gumbleter / H. Müller, Carl Hanser Verlag, 3rd Edition, 1989, Chapter 5.9.6, pages 342-489, or "PVC Technology", WV Titow, 4th Edition, Elsevier Publishers, 1984, pp. 165-170.
  • polymer plasticizers listed in the context of the first mentioned reference (R. Gumbleter / H. Müller) and suitable as solvents in the context of the invention, in particular those shown in Tables 9a (pp. 388-392), 10 (p 396), 11 (400), 12a (pp. 402-404), 13a (pp. 408-410), 13b (p.412), 14 (p.413), 16 (p.418), 3 (p 479) and 4 (p 486-488) are considered part of the disclosure of the present text.
  • polyester plasticizers are, for example, dicarboxylic acids such as adipic, phthalic, azelaic or sebacic acid and diols such as 1, 2-propanediol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol , Neopentyl glycol or diethylene glycol or mixtures of two or more thereof.
  • dicarboxylic acids such as adipic, phthalic, azelaic or sebacic acid
  • diols such as 1, 2-propanediol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol , Neopentyl glycol or diethylene glycol or mixtures of two or more thereof.
  • phosphoric esters are also suitable as plasticizers.
  • suitable phosphoric acid esters are tributyl phosphate, tri-2-ethylbutyl phosphate, tri-2-ethylhexyl phosphate, trichloroethyl phosphate, 2-ethylhexyl di-phenyl phosphate, triphenyl phosphate, tricresyl phosphate or trixyl nyl phosphate, or mixtures of two or more thereof.
  • a polymer composition according to the invention contains at least one phosphoric acid ester. Suitable amounts of phosphoric ester are, for example, within a range of 0.01 to about 50 wt .-%.
  • solvents in the context of the present invention are the following enumerated compounds: 2-hydroxy-5-methyl-benzoic acid methyl ester, 2-ethoxybenzyl alcohol, N-ethyl-2,3-dimethylaniline, 2-hydroxy-3-methyl-benzoic acid methyl ester, bicyclic acid benzyl ester , 3, 4,5- Trimethoxybenzyl alcohol, 3,5-dimethylbenzyl alcohol, 3-methylbenzophenone, 2-methoxyactetophenone, 3-cyclohexylpropionic acid, cyclopentanecarboxylic acid, 2,5-dimethylbenzonitrile, 4- (4-methoxyphenyl) -butan-2-one, formic acid cinnamate, triethyl citrate, dibutyl decandiate, heptaethylene glycol decanedioic diethy lester, adipic acid dibutyl ester, 1,2-bis (2-acetoxy-ethoxy)
  • a polymer composition according to the invention can be present in a polymer composition according to the invention either alone or as a mixture of two or more thereof.
  • a polymer composition according to the present invention is a liquid polymer composition containing two or more of the above-mentioned compounds as a solvent, one or more of the compounds other than the above definition may be used the term "liquid", provided that the entire solvent mixture is within this definition.
  • a polymer composition according to the invention contains solvent or solvent mixture in an amount of about 0.01 to about 50 weight percent.
  • a polymer composition according to the invention may contain one or more further additives in an amount of up to about 70% by weight.
  • additives which are suitable in principle for use in a polymer composition according to the invention alone or as a mixture of two or more thereof are listed below.
  • Suitable as additives in the context of the present invention are the amino nouracil compounds of the general formula II
  • radicals R 1 and R 2 are each independently of one another hydrogen, an optionally substituted linear or branched, saturated or unsaturated aliphatic alkyl radical having 1 to 44 carbon atoms, an optionally substituted saturated or unsaturated cycloalkyl radical having 6 to 44 carbon atoms or an optionally substituted aryl radical having 6 to 44 carbon atoms or an optionally substituted aralkyl radical having 7 to 44 carbon atoms or the radical R 1 is an optionally substituted acyl radical having 2 to 44 carbon atoms, and the radical R 3 is hydrogen, an optionally substituted linear or branched, saturated or unsaturated aliphatic hydrocarbon radical having 1 to 44 carbon atoms, an optionally substituted saturated or unsaturated cycloaliphatic hydrocarbon radical having 6 to 44 carbon atoms or an optionally substituted aromatic hydrocarbon radical having 6 to 44 carbon atoms.
  • n is a number from 1 to 100,000
  • the radicals R a , R b , R 4 and R 5 are each independently hydrogen, an optionally substituted linear or branched, saturated or unsaturated aliphatic alkyl radical having 1 to 44 carbon atoms , an optionally substituted saturated or unsaturated cycloalkyl radical having 6 to 44 carbon atoms or an optionally substituted aryl radical having 6 to 44 carbon atoms or an optionally substituted aralkyl radical having 7 to 44 carbon atoms or the radical R 4 is an optionally substituted acyl radical having 2 to 44 carbon atoms or the radicals R 4 and R 5 to an aromatic or heterocyclic system and in which the radical R 6 represents hydrogen, an optionally substituted, linear or branched, saturated or unsaturated aliphatic alkyl or alkylene radical or oxyalkyl or oxyalkylene radical or mercaptoalkyl or mercaptoalkylene radical or aminoalkyl or aminoalkylene radical 1 to
  • the compound of general formula I used is an ⁇ , ⁇ -unsaturated ⁇ -aminocarboxylic acid, in particular a compound based on ⁇ -aminocrotonic acid.
  • Particularly suitable in this case are the esters or thioesters of the corresponding aminocarboxylic acids with monohydric or polyhydric alcohols or mercaptans, where X in the cases mentioned is in each case O or S.
  • radical R 6 together with X is an alcohol or mercaptan radical
  • a radical can be selected, for example, from methanol, ethanol, propanol, isopropanol, butanol, 2-ethylhexanol, isooctanol, isononanol, decanol, lauryl alcohol, myristyl alcohol , Palmityl alcohol, stearyl alcohol, ethylene glycol, propylene glycol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, 1,10-decanediol, diethylene glycol, thio-diethanol, trimethylolpropane, glycerol, tris ( 2-hydroxymethyl) - isocyanurate, triethanolamine, pentaerythritol, di-trimethylolpropane, diglycerol, sorbitol, mannitol, xylit
  • the compound of general formula III used is a compound in which R 4 is a linear alkyl radical having 1 to 4 C atoms, R 5 is hydrogen and R 6 is a linear or branched, saturated , mono- to hexahydric alkyl or alkylene radical having 2 to 12 C atoms or a linear, branched or cyclic 2- to 6-valent ether alcohol radical or thioether alcohol radical.
  • Suitable compounds of general formula III include, for example, ⁇ -aminocrotonic acid stearyl ester, 1,4-butanediol-di ( ⁇ -aminocrotonic acid) ester, thiodiethanol- ⁇ -aminocrotonic acid ester, trimethylolpropane tri- ⁇ -aminocrotonic acid ester, pentaerythritol tetra- ⁇ - aminocrotonic acid ester, dipentaerythritol hexa-beta-amino crotonic acid ester and the like.
  • the compounds mentioned may each be contained in a polymer composition of the invention alone or as a mixture of two or more thereof.
  • compounds of the general formula III are, for example, compounds in which the radicals R 4 and R 5 are bonded to form an aromatic or heteroaromatic system, for example aminobenzoic acid, aminosalicylic acid or aminopyridinecarboxylic acid and suitable derivatives thereof.
  • Suitable additives are, for example, compounds which have a mercaptofunctional sp 2 -hybridized carbon atom, carbazoles, carbazole derivatives or 2,4-pyrrolidinedione or 2,4-pyrrolidinedione derivatives.
  • Z stands in principle for any structural element which is capable of forming a corresponding tautomeric compound, that is to say having at least one displaceable H atom.
  • the sp 2 -hybridised carbon atom may be part of an optionally substituted aliphatic compound or a constituent of an aromatic system.
  • suitable compound types are thiocarbamic acid derivatives, thiocarbamates, thiocarboxylic acids, thiobenzoic acid derivatives, thioacetone derivatives or thiourea or thiourea derivatives.
  • thiourea or a thiourea derivative is used as additive with at least one mercapto-functional, sp 2 -hybridized C atom.
  • epoxy compounds are epoxidized soybean oil, epoxidized olive oil, epoxidized linseed oil, epoxidized castor oil, epoxidized peanut oil, epoxidized corn oil, epoxidized cottonseed oil and glycidyl compounds.
  • 1,3-dicarbonyl compounds in particular the ⁇ -diketones and ⁇ -keto esters.
  • Dicarbonyl compounds of the general formula RC (O) CHR -C (O) R are particularly suitable for the purposes of the present invention, to which particular reference to the radicals R ', R "and R '", and the disclosure of which is considered to be part of the disclosure of the present text.
  • Particularly suitable here are, for example, acetylacetone, butanoylacetone, heptanoylacetone, stearoylacetone, palmitoylacetone, lauroylacetone, 7-tert-nonylthioheptanedione-2,4, benzoylacetone, dibenzoylmethane, lauroylbenzoylmethane, palmitoylbenzoylmethane, stearoylbenzoylmethane, isooctylbenzoylmethane, 5-hydroxycapronylbenzoylmethane, tribenzoylmethane , Bis (4-methylbenzoyl) methane, benzoyl-p-chlorobenzoylmethane, bis (2-hydroxybenzoyl) methane, 4-
  • Methoxybenzoylbenzoylmethane bis (4-methoxybenzoyl) methane, benzoylformylmethane, benzoylacetylphenylmethane, 1-benzoyl-1-acetylnonane, stearoyl-4-methoxybenzoylmethane, bis (4-tert-butylbenzoyl) methane, benzoylphenylacetylmethane, bis (cyclohexanoyl) methane, Dipivaloylmethane, 2-acetylcyclopentanone, 2-benzoylcyclopentanone, methyl, ethyl, butyl, 2-ethylhexyl, dodecyl or octadecyl, propionyl or Butyrylessigklaer with 1 to 18 carbon atoms and Stearoylessigkladreethyl-, -propyl -, -butyl
  • 1, 3 -Diketo compounds may be contained in a polymer composition according to the invention in an amount of up to about 20 wt .-%, for example up to about 10 wt .-%. Also suitable as additives in the context of the polymer composition according to the invention are polyols.
  • Suitable polyols are, for example, pentaerythritol, dipentaerythritol, tripentaerythritol, bistrimethylolpropane, inositol, polyvinyl alcohol, bistrimetalolethane, trimethylolpropane, sorbitol, maltitol, isomaltitol, lactitol, lycasin, mannitol, lactose, leucrose, tris (hydroxymethyl) isocyanurate, palatinite, tetramethylolcyclohexanol , Tetramethylolcyclopentanol, Tetramethylolcyclohep- tanol, glycerol, diglycerol, polyglycerol, thiodiglycerol or 1-0- ⁇ -D-glycopyranosyl-D-mannitol dihydrate.
  • the polyols suitable as additives may be contained in a polymer composition according to the invention in an amount of up to about 30% by weight, for example up to about 10% by weight.
  • additives are, for example, hindered amines as they are mentioned in EP-A 1 046 668 on pages 7 to 27.
  • the sterically hindered amines disclosed there are expressly incorporated by reference, the compounds mentioned there are considered as part of the disclosure of the present text.
  • the sterically hindered amines useful as additives may be contained in a polymer composition according to the invention in an amount of up to about 30% by weight, for example up to about 10% by weight.
  • a polymer composition of the present invention may further contain as an additive an organotin compound or a mixture of two or more organotin compounds.
  • organotin compounds are, for example, methyltin tris (isooctyl thioglycolate), methyltin tris (isooctyl-3-mercaptopropionate), methyltin tris-cisodecyl thioglycolate), dimethyltin bis (isooctyl thioglycolate), dibutyltin bis ( isooctyl-thioglycolate), monobutyltin tris (isooctyl thioglycolate), dioctyltin bis (isooctyl thioglycolate), monooctyltin tris (isooctyl thioglycolate), dioctyltin bis (isooctyl thiogly
  • organotin compounds mentioned in EP-A 0 742 259 on pages 18 to 29 and described in their preparation can be used.
  • the above-mentioned disclosure is expressly incorporated by reference, the compounds mentioned there and their preparation being understood as part of the disclosure of the present text.
  • a polymer composition according to the invention may contain the described organotin compounds in an amount of up to about 40% by weight, in particular up to about 20% by weight.
  • a polymer composition according to the invention may contain organic phosphite esters having 1 to 3 identical, pairwise identical or different organic radicals.
  • Suitable organic radicals are, for example, linear or branched, saturated or unsaturated alkyl radicals having 1 to 24 C atoms, optionally substituted alkyl radicals having 6 to 20 C atoms or optionally substituted aralkyl radicals having 7 to 20 C atoms.
  • organic phosphite esters are tris (nonylphenyl), trilauryl, tributyl, trioctyl, tridecyl, tridodecyl, triphenyl, octyldiphenyl, dioctylphenyl, tri (octylphenyl), tri-benzyl, butyldikresyl , Octyl-di (octylphenyl), tris (2-ethylhexyl), tritolyl, tris (2-cyclohexylphenyl), tri- ⁇ -naphthyl, tris (phenylphenyl), tris (2) phenylethyl), tris (dimethylphenyl), tricresyl or tris (p-nonylphenyl) phosphite or tristearyl sorbitol triphosphite or mixtures of two or more thereof.
  • a polymer composition according to the invention may furthermore contain, as additives, mercaptans blocked, as are mentioned on pages 4 to 18 in EP-A 0 742 259.
  • the disclosure in the indicated specification is expressly incorporated, it is understood as part of the disclosure of the present.
  • a polymer composition according to the invention may contain the described blocked mercaptans in an amount of up to about 30% by weight, in particular up to about 10% by weight.
  • a polymer composition according to the invention may furthermore contain lubricants such as montan wax, fatty acid esters, purified or hydrogenated natural or synthetic triglycerides or partial esters, polyethylene waxes, amide waxes, chloroparaffins, glycerol esters or alkaline earth metal soaps, if these lubricants do not fall under the term "solvent" within the meaning of the present text Lubricants which can be used as additives are moreover also described in "Kunststoffadditive", R. Gumbleter / H. Müller, Carl Hanser Verlag, 3rd edition, 1989, pages 478 - 488.
  • lubricants such as montan wax, fatty acid esters, purified or hydrogenated natural or synthetic triglycerides or partial esters, polyethylene waxes, amide waxes, chloroparaffins, glycerol esters or alkaline earth metal soaps, if these lubricants do not fall under the term "solvent” within the meaning
  • a polymer composition according to the invention may contain the described lubricants in an amount of up to about 70% by weight, in particular up to about 40% by weight.
  • additives for polymer composition according to the present invention are organic plasticizers, provided that these plasticizers are not already covered by the term "solvent" within the meaning of the present text.
  • Suitable plasticizers are, for example, polymer plasticizers, as described in "Kunststoffadditive”, R. Gumbleter / H. Müller, Carl Hanser Verlag, 3rd Edition, 1989, Chapter 5.9.6, pages 412-415, or "PVC Technology”, W.V. Titov, 4th Edition, Elsevier Publishers, 1984, pp. 165-170.
  • polyester plasticizers are, for example, dicarboxylic acids such as adipic, phthalic, azelaic or sebacic acid and diols such as 1,2-propanediol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol , Neopentyl glycol or diethylene glycol or mixtures of two or more thereof.
  • dicarboxylic acids such as adipic, phthalic, azelaic or sebacic acid
  • diols such as 1,2-propanediol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol , Neopentyl glycol or diethylene glycol or mixtures of two or more thereof.
  • phosphoric esters are also suitable as plasticizers, as can be found in the "pocket book of the plastic additives", Chapter 5.9.5, pp. 408-412.
  • suitable phosphoric acid esters are tributyl phosphate, tri-2-ethylbutyl phosphate, tri-2-ethylhexyl phosphate, trichloroethyl phosphate, 2-ethylhexyl di-phenyl phosphate, triphenyl phosphate, tricresyl phosphate or trixyl nyl phosphate, or mixtures of two or more thereof.
  • plasticizers are chlorinated hydrocarbons (paraffins) or hydrocarbons as described in "Kunststoffadditive", R. Gumbleter / H. Müller, Carl Hanser Verlag, 3rd edition, 1989, chapter 5.9.14.2, pp. 422-425 and chapter 5.9.14.1, p. 422.
  • a polymer composition according to the invention may contain the plasticizers described in an amount of up to about 99.5% by weight, in particular up to about 30% by weight, up to about 20% by weight or up to about 10% by weight ,
  • the lower limit for the described plasticizers as a constituent of the polymer compositions according to the invention is about 0.1% by weight or more, for example about 0.5% by weight, 1% by weight, 2 Wt .-% or 5 wt .-%.
  • the polymer compositions according to the invention may contain antioxidants, UV absorbers or light stabilizers.
  • Suitable antioxidants are described, for example, in EP-A 1 046 668 on pages 33 to 35.
  • Suitable UV absorbers and light stabilizers are mentioned on pages 35 and 36 there. Both disclosures are hereby incorporated by reference, the disclosures being considered as part of this text.
  • a polymer composition according to the invention may contain further additives which are not soluble in the polymer compositions according to the invention.
  • all additives are suitable, for example those which do not or do not substantially influence the transparency of a polymer composition produced with the aid of such a polymer composition.
  • hydrotalcites hydrocalumites, zeolites and alkali metal aluminocarbonates.
  • Suitable hydrotalcites, hydrocalumites, zeolites and alkali metal aluminocarbonates are described, for example, in EP-A 1 046 668 on pages 27 to 29, EP-A 256 872 on pages 3, 5 and 7, of DE-C 41 06 411 on page 2 and 3 or DE-C 41 06 404 on page 2 and 3 or DE-C 198 60 798.
  • EP-A 1 046 668 on pages 27 to 29, EP-A 256 872 on pages 3, 5 and 7, of DE-C 41 06 411 on page 2 and 3 or DE-C 41 06 404 on page 2 and 3 or DE-C 198 60 798.
  • hydrotalcites, hydrocalumites, zeolites and alkali metal thiocarbonates suitable as additives may be present in a polymer composition according to the invention in an amount of up to about 5% by weight, for example from 0 to about 3% by weight.
  • the metal oxides, metal hydroxides or metal soaps suitable as additives preferably have a divalent cation, particularly suitable are the cations of calcium or zinc or mixtures thereof.
  • suitable carboxylic acid anions include anions of monovalent carboxylic acids such as acetic acid, propionic acid, butyric acid, valeric acid, hexanoic acid, enanthic acid, octanoic acid, neodecanoic acid, 2-ethylhexanoic acid, pelargonic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, myristylic acid, p-mitic acid, lauric acid, Isostearic acid, stearic acid, 12-hydroxystearic acid, 9,10-dihydroxystearic acid, oleic acid, 3,6-dioxaheptanoic acid, 3,6,9-trioxadecanoic acid, behenic acid, benzoic acid, p-tert-butylbenzoic acid, dimethylhydroxybenzoic acid, 3,5-dicarboxylic acid.
  • monovalent carboxylic acids such as
  • tert-butyl-4-hydroxybenzoic acid toluic acid, dimethylbenzoic acid, ethylbenzoic acid, n-propylbenzoic acid, salicylic acid, p-tert-octylsalicylic acid, sorbic acid, anions of divalent carboxylic acids or their monoesters, such as oxalic acid, malonic acid, maleic acid, tartaric acid, cinnamic acid, Mandelic acid, malic acid, glycolic acid, oxalic acid, salicylic acid, Polyglykoldicar- bonklaren having a degree of polymerization of about 10 to about 12, phthalic acid, isophthalic acid, terephthalic acid or hydroxyphthalic acid, anions of tri- or tetravalent carboxylic acids or their mono-, di- or triesters as they in mimellitic acid, trimellitic acid, pyromellitic acid or citric acid and furthermore so-called overbased carboxylates
  • metal soaps are preferably used whose anions are derived from saturated or unsaturated carboxylic acids or hydroxycarboxylic acids having about 8 to about 20 C atoms. Particular preference is given here to stearates, oleates, laurates, palmitates, behenates, versatates, hydroxystearates, dihydroxystearates, p-tert-butylbenzoates or (iso) octanoates of calcium or zinc or mixtures of two or more thereof.
  • a polymer composition according to the invention comprises calcium stearate or zinc stearate or a mixture thereof.
  • a polymer composition according to the invention may contain said metal oxides, metal hydroxides or metal soaps or a mixture of two or more thereof in an amount of up to about 5% by weight, for example in an amount of from 0 to about 3% by weight.
  • a polymer composition according to the invention may further comprise fillers as described in Handbook of PVC Forming, EJ Wickson, John Wiley & Sons, Inc., 1993, at pages 393-449, or reinforcing agents as described in U.S. Pat "Taschenbuch der Kunststoffadditive", R. Gumbleter / H. Müller, Carl Hanser Verlag, 1990, pages 549-615, or pigments.
  • a polymer composition according to the invention may additionally contain impact modifiers and processing aids, gelling agents, further antistatic agents, biocides, metal deactivators, optical brighteners, flame retardants and antifogging compounds.
  • impact modifiers and processing aids gelling agents, further antistatic agents, biocides, metal deactivators, optical brighteners, flame retardants and antifogging compounds.
  • Suitable compounds of these classes of compounds are described, for example, in "Kunststoff Additive”, R. Keßler / H. Müller, Carl Hanser Verlag, 3rd edition, 1989 and in the "Handbook of PVC Formulating", EJ. Wilson, J. Wiley & Sons, 1993.
  • halogen-containing organic polymers which are suitable as part of a polymer composition according to the invention are polymers of vinyl chloride, vinyl resins containing vinyl chloride units in the polymer backbone, copolymers of vinyl chloride and vinyl esters of aliphatic acids, in particular vinyl acetate, copolymers of vinyl chloride with esters of acrylic and methacrylic acid or acrylonitrile or Mixtures of two or more thereof, copolymers of vinyl chloride with diene compounds or unsaturated dicarboxylic acids or their anhydrides, for example copolymers of vinyl chloride with diethyl maleate, diethyl fumarate or maleic anhydride, postchlorinated polymers and copolymers of vinyl chloride, copolymers of vinyl chloride and vinylidene chloride with unsaturated aldehydes, ketones and other compounds such as acrolein, crotonaldehyde, vinyl methyl ketone, vinyl methyl ether, vinyl isobutyl ether
  • graft polymers of PVC with EVA, ABS or MBS are also suitable as a constituent of the polymer compositions according to the invention.
  • Preferred substrates for such graft copolymers are also the abovementioned homopolymers and copolymers, in particular mixtures of vinyl chloride homopolymers with other thermoplastic or elastomeric polymers, in particular blends with ABS, MBS, NBR, SAN, EVA, CPE, MBAS, PAA (Polyalkyl acrylate), PAMA (polyalkyl methacrylate), EPDM, polyamides or polylactones.
  • halogenated and non-halogenated polymers for example mixtures of the abovementioned non-halogenated polymers with PVC, in particular mixtures of polyurethanes and PVC.
  • PVC polyurethanes
  • PVC polyurethanes
  • recyclates of chlorine-containing polymers can also be stabilized and improved in their discharge properties, with basically all recyclates of the abovementioned halogenated polymers being suitable for this purpose.
  • Suitable in the context of the present invention for example, PVC recycled material.
  • the present invention also relates to a stabilizer composition which contains at least one organic ammonium perchlorate, at least one aminoalcohol having from 2 to 12 carbon atoms in the alcohol radical and at least one additive.
  • Suitable additives are those in the mentioned in the present text and expressly designated as such.
  • a stabilizer composition for a stabilizer composition according to the invention, the amounts given above apply with regard to their contents, the amounts given in each case being adjusted by the proportion of polymer to be stabilized. Insofar as the present text therefore refers to a "polymer composition", the statements made in this context with regard to the constituents (stabilizer composition) which are not to be stabilized also apply fully to the present stabilizer composition, unless expressly stated otherwise.
  • a polymer composition according to the invention contains the stabilizer composition, which usually contribute to an improvement in the properties of a polymer during or after processing in an amount of 0.1 to 20 phr, in particular about 0.5 to about 15 phr or about 1 to about 12 phr. Values of at least 0.3 phr, such as at least about 0.4 or at least about 0.75 phr, are preferred.
  • the unit phr stands for "per hundred resin" and thus relates to parts by weight per 100 parts by weight of polymer.
  • a polymer composition according to the invention as a halogenated polymer at least partially contains PVC, wherein the PVC content is in particular at least about 20, preferably at least about 50 wt .-%, for example at least about 80 or at least about 90 wt .-%.
  • the mixing of polymers or polymers and the stabilizer composition according to the invention can in principle be carried out at any time before or during the processing of the polymer.
  • the polymer additive composition for example, be added to the present in powder or granular polymer before processing.
  • a polymer composition according to the invention can be brought into a desired form in a known manner. Suitable methods are, for example, calendering, extrusion, injection molding, sintering, extrusion blow molding or the plastisol process. A polymer composition according to the invention can also be used, for example, for the production of foams. In principle, the polymer composition according to the invention are suitable for the production of hard or in particular soft PVC.
  • a polymer composition according to the invention can be processed into shaped bodies.
  • the present invention therefore also relates to shaped bodies, at least comprising a polymer composition according to the invention or a polymer composition according to the invention.
  • the term "shaped body” basically encompasses all three-dimensional structures that can be produced from a polymer composition according to the invention.
  • the term “shaped body” includes, for example, wire sheathings, automobile components, for example automobile components used in the interior of the automobile, in the engine compartment or on the outer surfaces, cable insulation, decorative foils, agricultural foils, hoses, sealing profiles, office foils, hollow bodies ( Bottles), packaging films (thermoformed films), blown films, pipes, foams, heavy profiles (window frames), light wall profiles, building profiles, sidings, fittings, sheets, foam sheets, recycled core or coextrudates Housing for electrical equipment or machines, such as computers or household appliances.
  • Further examples of moldings which can be produced from a polymer composition according to the invention are artificial leather, floor coverings, textile coatings, wallpaper, coil coatings or underbody protection for motor vehicles.
  • the amino alcohol is an alkanolamine in the context of the use according to the invention.
  • the aminoalcohol is an aminomonoalcohol or an aminodialcohol or an aminotrialcohol or a mixture of two or more thereof.
  • the aminoalcohol is a monoaminoalcohol in the context of the use according to the invention.
  • a polymer composition according to the invention for the production of polymeric moldings or surface coating compositions.
  • films having compositions as shown in Table 1 were first prepared. In this case, film 1 was produced entirely without stabilizer composition. Films 2 and 3 contained known sodium perchlorate-based stabilizer compositions, and Films 4, 5 and 6 of the invention each contained a different polymer composition according to the invention identified in Table 1. Of the samples 1 to 6 thus prepared, three specimens each having a mass of 50 ⁇ 5 mg at a test temperature of 200 ⁇ 0.5 0 C were subjected to a thermal stability test according to DIN VDE 0472 part 614 in a metal block thermostat from Liebisch , The mean values calculated from the three individual values are also given in Table 1.
  • samples 1 to 6 The discharge behavior of samples 1 to 6 was carried out with the aid of an EMF 20 from the manufacturer Eltex.
  • EMF 20 from the manufacturer Eltex.
  • the 210 ⁇ 210 mm PVC rolled sheets conditioned for one day at room temperature were clamped in the measuring apparatus and provided with a static charge of 10 kV.

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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 une composition polymère contenant au moins un perchlorate d'ammonium et au moins un solvant organique, pour polymères de préférence halogénés.
EP05846583A 2004-12-17 2005-12-16 Composition polymere a equipement antistatique, son mode de production et son utilisation Withdrawn EP1836248A1 (fr)

Applications Claiming Priority (2)

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DE102004060928A DE102004060928A1 (de) 2004-12-17 2004-12-17 Antistatisch ausgerüstete Polymerzusammensetzung, deren Herstellung und Verwendung
PCT/EP2005/013608 WO2006066834A1 (fr) 2004-12-17 2005-12-16 Composition polymere a equipement antistatique, son mode de production et son utilisation

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CN103422352B (zh) * 2013-07-31 2015-07-29 天津新纶科技有限公司 一种多羟基聚醚链段季铵盐抗静电剂、制备方法和由其制备的抗静电整理剂
CN109735025B (zh) * 2019-01-14 2021-04-27 固德电材系统（苏州）股份有限公司 一种抗静电pvc板材材料及其制备方法和应用

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US3892610A (en) * 1973-01-08 1975-07-01 Hercules Inc Freeze drying process of making ultra-fine ammonium perchlorate and product
EP0079646B1 (fr) * 1981-11-16 1986-05-21 Unilever N.V. Composition détergente liquide
JPH0621211B2 (ja) * 1985-08-13 1994-03-23 旭電化工業株式会社 塩化ビニル樹脂組成物
DE3630783A1 (de) * 1986-09-10 1988-03-24 Neynaber Chemie Gmbh Gleitmittel fuer thermoplastische kunststoffe
EP0755969B1 (fr) * 1989-12-11 2000-03-01 Witco Vinyl Additives GmbH Esters bêta-cétoniques comme stabilisateurs pour polymères chlorés
DE4002988A1 (de) * 1990-02-01 1991-08-14 Baerlocher Chem Basische calcium-aluminium-hydroxid-dicarboxylate, verfahren zu deren herstellung und deren verwendung
DE4106411C2 (de) * 1991-02-28 1994-09-01 Baerlocher Gmbh Basische Calcium-Aluminium-Hydroxy-Phosphite, Verfahren zu deren Herstellung und deren Verwendung
DE4106404C2 (de) * 1991-02-28 1995-05-18 Baerlocher Gmbh Calcium-Aluminium-Hydroxid-Dicarboxylate, Verfahren zu deren Herstellung und deren Verwendung
DE59610885D1 (de) * 1995-10-13 2004-02-05 Crompton Vinyl Additives Gmbh Stabilisatorkombinationen für chlorhaltige Polymere
DE10124734A1 (de) * 2001-05-21 2002-12-05 Baerlocher Gmbh Fein verteilte Stabilisatorzusammensetzung für halogenhaltige Polymere

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