WO2003004555A1 - Verwendung von cyanacetylharnstoffen zur stabilisierung von antistatisch ausgerüsteten halogenhaltigen organischen kunststoffen - Google Patents
Verwendung von cyanacetylharnstoffen zur stabilisierung von antistatisch ausgerüsteten halogenhaltigen organischen kunststoffen Download PDFInfo
- Publication number
- WO2003004555A1 WO2003004555A1 PCT/EP2002/007104 EP0207104W WO03004555A1 WO 2003004555 A1 WO2003004555 A1 WO 2003004555A1 EP 0207104 W EP0207104 W EP 0207104W WO 03004555 A1 WO03004555 A1 WO 03004555A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- pvc
- antistatic
- carbon atoms
- atoms
- radicals
- Prior art date
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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
- C08K5/315—Compounds containing carbon-to-nitrogen triple bonds
Definitions
- the invention relates to the use of cyanoacetylureas 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 / MüUer, "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 adequate 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
- Cyanoacetylureas for stabilizing antistatically treated 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.
- Cyanoacetylureas are substances known to the person skilled in the art and are characterized by the formula (I)
- radicals R and R independently of one another each have an unbranched or branched, linear or cyclic alkyl radical having 1 to 18 carbon atoms or an aryl radical having 6 to 18 carbon atoms, which may be one or more alkyl radicals can each be substituted with 1 to 6 carbon atoms.
- N, N'-dimethyl-N-cyanoacetylurea is particularly preferred; in this compound, the radicals R 1 and R 2 in the formula (I) each represent a methyl group.
- compositions for stabilizing antistatic halogen-containing organic plastics, in particular PVC, against thermal and / or photochemical degradation characterized in that these compositions contain one or more cyanoacetylureas (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 are also suitable.
- perchlorate-alcohol complexes the types known to the person skilled in the art from EP-B-394 547, page 3, lines 37 to 56 are expressly included.
- 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 mounted on a carrier material such as PVC, calcium silicate, zeolites or hydrotalcites, or incorporated by chemical reaction in a hydrotalcite or another layered lattice compound.
- a carrier material such as PVC, calcium silicate, zeolites or hydrotalcites, or incorporated by chemical reaction in a hydrotalcite or another layered lattice compound.
- PVC polyol partial ethers
- Glycerol monoether and glycerol monothioether preferred.
- the perchlorates can be used both individually and in a mixture with one another.
- Another subject matter of the invention is a method for stabilizing antistatic halogen-containing organic plastics, in particular PVC, against thermal and / or photochemical degradation, one or more cyanoacetylureas (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 and antistatic PVC can be known Be prepared by using compounds known per se, such as the processing apparatus mentioned above, to mix the compounds (I) or a stabilizer combination according to the invention and antistatic agents and, if desired, other conventional plastic additives with PVC.
- 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 In the case of antistatically treated halogen-containing organic plastics, the compounds (I) or the compositions according to the invention are used Stabilize applies, it is in particular chlorine-containing polymers or their recyclates.
- 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 aldeh
- PVC polystyrene resin
- ABS polystyrene resin
- MBS polystyrene resin
- SAN polystyrene resin
- EVA polystyrene resin
- CPE polystyrene resin
- MBAS polystyrene resin
- PMA polystyrene resin
- EPDM EPDM 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)
- Example 2 is according to the invention. Examples 1 are used for comparison.
- test recipes were. - partially or completely - the following measurements were carried out:
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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
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003510718A JP2004533527A (ja) | 2001-07-06 | 2002-06-27 | 帯電防止ハロゲン含有有機プラスチックを安定化させるためのシアノアセチル尿素の使用 |
EP02760198A EP1406961A1 (de) | 2001-07-06 | 2002-06-27 | Verwendung von cyanacetylharnstoffen zur stabilisierung von antistatisch ausgerüsteten halogenhaltigen organischen kunststoffen |
US10/483,031 US20040225043A1 (en) | 2001-07-06 | 2002-06-27 | Use of cyanogen acetylureas for stabilising antistatic organic plastics containing halogen |
BR0210825-9A BR0210825A (pt) | 2001-07-06 | 2002-06-27 | Uso de cianoacetil uréias para estabilizar plásticos orgânicos antiestáticos contendo halogênio |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2001132835 DE10132835A1 (de) | 2001-07-06 | 2001-07-06 | Verwendung von Cyanacetylharnstoffen zur Stabilisierung von antistatisch ausgerüsteten halogenhaltigen organischen Kunststoffen |
DE10132835.4 | 2001-07-06 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2003004555A1 true WO2003004555A1 (de) | 2003-01-16 |
Family
ID=7690863
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2002/007104 WO2003004555A1 (de) | 2001-07-06 | 2002-06-27 | Verwendung von cyanacetylharnstoffen zur stabilisierung von antistatisch ausgerüsteten halogenhaltigen organischen kunststoffen |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP1406961A1 (de) |
JP (1) | JP2004533527A (de) |
BR (1) | BR0210825A (de) |
DE (1) | DE10132835A1 (de) |
WO (1) | WO2003004555A1 (de) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0962491A1 (de) * | 1998-06-02 | 1999-12-08 | Witco Vinyl Additives GmbH | Cyanacetylharnstoffe zum Stabilisieren von halogenhaltigen Polymeren |
DE19947860A1 (de) * | 1999-10-05 | 2001-04-12 | Cognis Deutschland Gmbh | Verwendung von Harnstoffderivaten der Cyanessigsäure als Stabilisatoren für chlorhaltige thermoplastische Kunststoffe |
DE10056880A1 (de) * | 2000-11-16 | 2002-05-23 | Cognis Deutschland Gmbh | Stabilisator-Zusammensetzung für halogenhaltige organische Kunststoffe |
-
2001
- 2001-07-06 DE DE2001132835 patent/DE10132835A1/de not_active Withdrawn
-
2002
- 2002-06-27 BR BR0210825-9A patent/BR0210825A/pt active Pending
- 2002-06-27 EP EP02760198A patent/EP1406961A1/de not_active Withdrawn
- 2002-06-27 WO PCT/EP2002/007104 patent/WO2003004555A1/de not_active Application Discontinuation
- 2002-06-27 JP JP2003510718A patent/JP2004533527A/ja active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0962491A1 (de) * | 1998-06-02 | 1999-12-08 | Witco Vinyl Additives GmbH | Cyanacetylharnstoffe zum Stabilisieren von halogenhaltigen Polymeren |
DE19947860A1 (de) * | 1999-10-05 | 2001-04-12 | Cognis Deutschland Gmbh | Verwendung von Harnstoffderivaten der Cyanessigsäure als Stabilisatoren für chlorhaltige thermoplastische Kunststoffe |
DE10056880A1 (de) * | 2000-11-16 | 2002-05-23 | Cognis Deutschland Gmbh | Stabilisator-Zusammensetzung für halogenhaltige organische Kunststoffe |
Also Published As
Publication number | Publication date |
---|---|
JP2004533527A (ja) | 2004-11-04 |
BR0210825A (pt) | 2004-06-22 |
DE10132835A1 (de) | 2003-01-16 |
EP1406961A1 (de) | 2004-04-14 |
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