EP1406962A1 - Utilisation d'amino-uraciles pour stabiliser des matieres synthetiques organiques contenant des halogenes et traitees antistatiques - Google Patents

Utilisation d'amino-uraciles pour stabiliser des matieres synthetiques organiques contenant des halogenes et traitees antistatiques

Info

Publication number
EP1406962A1
EP1406962A1 EP02754768A EP02754768A EP1406962A1 EP 1406962 A1 EP1406962 A1 EP 1406962A1 EP 02754768 A EP02754768 A EP 02754768A EP 02754768 A EP02754768 A EP 02754768A EP 1406962 A1 EP1406962 A1 EP 1406962A1
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
pvc
antistatic
radicals
halogen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP02754768A
Other languages
German (de)
English (en)
Inventor
Peter Daute
Peter Wedl
Jörg-Dieter KLAMANN
Ernst-Udo Brand
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Reagens Deutschland GmbH
Original Assignee
Cognis Deutschland GmbH and Co KG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Cognis Deutschland GmbH and Co KG filed Critical Cognis Deutschland GmbH and Co KG
Publication of EP1406962A1 publication Critical patent/EP1406962A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
    • C08K5/3462—Six-membered rings

Definitions

  • the invention relates to the use of aminouracils for the stabilization of antistatically treated halogen-containing organic plastics.
  • Halogen-containing plastics or molding materials made from them are known to tend to decomposition or decomposition reactions when they are exposed to thermal stress or come into contact with high-energy radiation, for example ultraviolet light.
  • Metal-containing stabilizers based on Pb, Ba, Cd, Sn, Ca and Zn are mostly used to stabilize PVC during processing.
  • Urea derivatives such as e.g. Diphenylthiourea proposed for stabilizing PVC (compare: Gumbleter / Müller, “Plastic Additives", Carl Hanser Verlag 1989, p. 312). These compounds are mostly used in combination with metal-containing stabilizers, since they generally do not result in sufficient long-term stabilization.
  • these substances should be able to ensure the thermal stability of PVC equipped with internal antistatic agents, in particular quaternary ammonium compounds and amine derivatives.
  • the present invention relates to the use of aminouracils for stabilizing antistatic halogen-containing organic plastics against thermal and / or photochemical degradation.
  • the compounds (I) are used to stabilize antistatic PVC against thermal and / or photochemical degradation.
  • Aminouracile (T) are represented by the formula (I)
  • radicals R 1 and R 2 are each independently
  • Dimethylaminouracil (I *) is very particularly preferred.
  • stabilizer compositions for stabilizing halogen-containing organic plastics, in particular PVC, which have antistatic properties, against thermal and / or photochemical degradation characterized in that these compositions contain one or more aminouracils (I).
  • the stabilizer compositions contain one or more perchlorates in addition to the compounds (I).
  • Perchlorates in the sense of the invention are understood to mean metal salts and ammonium salts of perchloric acid.
  • Examples of perchlorates suitable according to the invention are those of the formula M (C10 4 ) n , where M in particular represents ammonium, Li, Na, K, Mg, Ca, Sr, Zn, Al, La or Ce.
  • the index n corresponds to the valence of the cation M 1, 2 or 3.
  • the perchlorate salts can be complexed with alcohols, for example polyols, cyclodextrins, or ether alcohols or ester alcohols, or be dissolved therein.
  • the polyol partial esters are also to be counted among the ester alcohols.
  • polyhydric alcohols or polyols their dimers, trimers, oligomers and polymers, such as di-, tri-, tetra- and polyglycols, and also di-, tri- and Tetrapentaerythritol or polyvinyl alcohol in various degrees of polymerization. in the
  • EP-B-394 547 page 3, lines 37 to 56 of known types.
  • the perchlorate salts can be used in various common dosage forms, for example as a salt or solution in water or an organic solvent as such, or applied to a support material such as PVC, calcium silicate, zeolites or hydrotalcites, or incorporated into a hydrotalcite by chemical reaction or another layered grid connection.
  • a support material such as PVC, calcium silicate, zeolites or hydrotalcites, or incorporated into a hydrotalcite by chemical reaction or another layered grid connection.
  • Glycerol monoether and glycerol monothioether preferred.
  • the perchlorates can be used both individually and in a mixture with one another.
  • Another object of the invention is a method for stabilizing antistatically treated halogen-containing organic plastics, in particular PVC, against thermal and / or photochemical degradation, one or more aminouracils (I) being added to the plastics, which in particular contain internal (internal) antistatic agents.
  • the components, that is to say the antistatic PVC and the compounds (I) are preferably mixed intimately in suitable apparatus.
  • compositions according to the invention can expediently be incorporated by the following methods:
  • the invention further relates to a stabilized PVC which on the one hand contains one or more antistatic agents, in particular internal (internal) antistatic agents, and on the other hand contains one or more of the compounds (I).
  • a stabilized PVC which on the one hand contains one or more antistatic agents, in particular internal (internal) antistatic agents, and on the other hand contains one or more of the compounds (I).
  • Such stabilized and antistatic PVC can be produced in a manner known per se, for which purpose compounds (I) or a stabilizer combination according to the invention and antistatics and, if desired, other conventional plastic additives are mixed with PVC using devices known per se, such as the processing apparatus mentioned above.
  • the PVC additionally contains one or more perchlorates.
  • the stabilized PVC containing antistatic agents preferably contains the compounds (I) in an amount of 0.01 to 2.0 phr and in particular 0.01 to 0.5 phr.
  • the term phr (parts per hundred resin) familiar to the person skilled in the art indicates how many parts by weight of the component are present in PVC, based on 100 parts by weight of PVC.
  • the stabilized PVC containing antistatic agents preferably contains the perchlorates in an amount of 0.01 to 2.0 phr and in particular 0.01 to 0.5 phr.
  • the PVC stabilized according to the present invention can be brought into the desired shape in known ways. Such processes are, for example, calendering, extruding, injection molding, sintering or spinning, furthermore extrusion blowing or processing according to the plastisol process.
  • Plastisol processing, extrusion and calendering are particularly preferred as processes for processing the PVC stabilized according to the invention.
  • the PVC stabilized according to the invention is suitable for hard, semi-hard and soft formulations.
  • Halogen-containing organic plastics The antistatically treated halogen-containing organic plastics which are to be stabilized with the compounds (I) or the compositions according to the invention are, in particular, chlorine-containing polymers or their recyclates.
  • Examples of such chlorine-containing polymers or their recyclates to be stabilized are: polymers of vinyl chloride, vinyl resins containing vinyl chloride units in their structure, such as 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 and with acrylonitrile Copolymers of vinyl chloride with diene compounds and unsaturated dicarboxylic acids or their anhydrides, such as copolymers of vinyl chloride with diethyl maleate, diethyl fumarate or maleic anhydride, post-chlorinated polymers and copolymers of vinyl chloride, copolymers of vinyl chloride and vinylidene chloride with unsaturated aldehydes, ketones and others, such as acrolein, such as acrolein , Vinyl methyl ether, vinyl isobutyl ether and the like; Polymers of vinylidene chloride and copolymers thereof with
  • graft polymers of PVC with EVA, ABS and MBS are also included.
  • Preferred substrates are also mixtures of the homopolymers and copolymers mentioned above, in particular vinyl chloride homopolymers, with other thermoplastic and / or elastomeric polymers, in particular blends with ABS, MBS, NBR, SAN, EVA, CPE, MBAS, PMA, PMMA, EPDM and polylactones.
  • Suspension and bulk polymers and emulsion polymers are also preferred.
  • Polyvinyl chloride is particularly preferred as the chlorine-containing polymer, in particular suspension polymer and bulk polymer.
  • PVC is also understood to mean copolymers or graft polymers of PVC with polymerizable compounds such as acrylonitrile, vinyl acetate or ABS, which may be suspension, bulk or emulsion polymers. PVC homopolymer is also preferred in combination with polyacrylates.
  • Recyclates of chlorine-containing polymers are also suitable, these being the polymers described in more detail above, which have been damaged by processing, use or storage.
  • PVC recyclate is particularly preferred.
  • the recyclates may also contain small amounts of foreign substances, such as paper, pigments, adhesives, which are often difficult to remove. These foreign substances can also come from contact with various substances during use or refurbishment, such as fuel residues, paint components, metal traces and initiator residues.
  • Vestinol AH dioctyl phthalate (from BASF)
  • Kronoss 2220 titanium dioxide (Kronos Titan)
  • Dehydate 80 X antistatic: paraffin sulfonate, Na salt (Cognis / DE)
  • Na perchlorate 50% by weight solution of Na perchlorate in water
  • Table 1 the individual recipe components of the examined test recipes were given, on the one hand, and the determined test results, on the other hand.
  • the respective numbers of the examples are given in the first line of the table.
  • the proportions of the individual components are given in phr; phr means "part per hundred resin" and indicates how many parts by weight of the respective component are present in PVC after adding the composition - based on 100 parts by weight of PVC.
  • the recipes each contain 100 parts of PVC (sum of Norvinyl S 6260 and Vestolith E 6007).
  • Examples 4 and 5 and 7 to 8 are according to the invention. Examples 1, 2, 3 and 6 are used for comparison.

Landscapes

  • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des amino-uraciles de formule (I), dans laquelle les restes R1 et R2 signifient chacun indépendamment hydrogène ou un reste alkyle cyclique ou linéaire, ramifié ou non, avec 1 à 18 atomes C ou bien un reste aryle avec 6 à 18 atomes C pouvant être éventuellement substitué par un ou plusieurs restes alkyle ayant chacun 1 à 6 atomes C. Ces amino-uraciles s'avèrent utiles pour stabiliser des matières synthétiques organiques contenant des halogènes et traitées antistatiques et pour les protéger de la dégradation thermique et/ou photochimique.
EP02754768A 2001-07-06 2002-06-27 Utilisation d'amino-uraciles pour stabiliser des matieres synthetiques organiques contenant des halogenes et traitees antistatiques Withdrawn EP1406962A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10132836 2001-07-06
DE10132836A DE10132836A1 (de) 2001-07-06 2001-07-06 Verwendung von Aminouracilen zur Stabilisierung von antistatisch ausgerüsteten halogenhaltigen organischen Kunststoffen
PCT/EP2002/007105 WO2003004556A1 (fr) 2001-07-06 2002-06-27 Utilisation d'amino-uraciles pour stabiliser des matieres synthetiques organiques contenant des halogenes et traitees antistatiques

Publications (1)

Publication Number Publication Date
EP1406962A1 true EP1406962A1 (fr) 2004-04-14

Family

ID=7690864

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02754768A Withdrawn EP1406962A1 (fr) 2001-07-06 2002-06-27 Utilisation d'amino-uraciles pour stabiliser des matieres synthetiques organiques contenant des halogenes et traitees antistatiques

Country Status (6)

Country Link
US (1) US20040235991A1 (fr)
EP (1) EP1406962A1 (fr)
JP (1) JP2004533528A (fr)
BR (1) BR0210778A (fr)
DE (1) DE10132836A1 (fr)
WO (1) WO2003004556A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102007027371A1 (de) * 2007-06-11 2008-12-18 Cognis Oleochemicals Gmbh Verfahren zur Herstellung einer Verbindung aufweisend mindestens eine Ester-Gruppe
US10202500B2 (en) 2013-03-15 2019-02-12 Lubrizol Advanced Materials, Inc. Heavy metal free CPVC compounds
JP6702449B1 (ja) * 2019-01-18 2020-06-03 堺化学工業株式会社 塩素含有樹脂組成物及びその成形体
CN114835651B (zh) * 2022-05-05 2023-08-29 横店集团得邦工程塑料有限公司 一种高透明pvc热稳定剂的制备方法及其在软质透明pvc板中的应用

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3162945D1 (en) * 1980-06-02 1984-05-10 Ciba Geigy Ag Chlorine-containing thermoplastic polymers stabilized with amino-thiouracils
US4656209A (en) * 1982-05-26 1987-04-07 Ciba-Geigy Corporation Chlorinated thermoplastics stabilized with aminouracils
PT751179E (pt) * 1995-06-28 2006-09-29 Crompton Vinyl Additives Gmbh Polimeros contendo halogenio, com preparacao antiestatica
ATE302816T1 (de) * 1995-10-13 2005-09-15 Crompton Vinyl Additives Gmbh Stabilisatorkombinationen für chlorhaltige polymere
MY114466A (en) * 1996-09-25 2002-10-31 Crompton Vinyl Additives Gmbh Rigid pvc stabilised with n, n-dimethyl-6-aminouracils
US20020032259A1 (en) * 2000-07-14 2002-03-14 Harvey Heather Blue Stabliser system comprising hydroxyacids
WO2002006389A2 (fr) * 2000-07-14 2002-01-24 Akzo Nobel N.V. Systeme stabilisateur comprenant des hydroxyacides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO03004556A1 *

Also Published As

Publication number Publication date
US20040235991A1 (en) 2004-11-25
DE10132836A1 (de) 2003-01-16
JP2004533528A (ja) 2004-11-04
BR0210778A (pt) 2004-07-20
WO2003004556A1 (fr) 2003-01-16

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