WO2001046310A1 - Mischungen aus phosphanen und chroman-derivaten - Google Patents
Mischungen aus phosphanen und chroman-derivaten Download PDFInfo
- Publication number
- WO2001046310A1 WO2001046310A1 PCT/IB2000/001897 IB0001897W WO0146310A1 WO 2001046310 A1 WO2001046310 A1 WO 2001046310A1 IB 0001897 W IB0001897 W IB 0001897W WO 0146310 A1 WO0146310 A1 WO 0146310A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- branched
- linear
- alkyl
- cycloalkyl
- groups
- Prior art date
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
- C08K5/49—Phosphorus-containing compounds
- C08K5/50—Phosphorus bound to carbon only
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1545—Six-membered rings
-
- 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
- C08K5/20—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/10—Homopolymers or copolymers of propene
Definitions
- the invention relates to synergistic mixtures containing phosphines, (D ⁇ / Ol ⁇ go) phosphanes, cyclophosphanes as component 1 and 6-hydroxy-Chromander ⁇ vate as component 2 and a method for stabilizing polymers against degradation caused by heat or mechanical stress with such mixtures
- the polymers When processing polymers into the end products, the polymers are exposed, among other things, to high temperatures. This can have an adverse effect on the melt viscosity and physical properties of the polymers and on the appearance of the end products produced therefrom. Suitable stabilizers or stabilizer systems are therefore necessary to prevent oxidation, chain breakage or discoloration to minimize
- synergistic stabilizer mixture according to the invention which, since it prevents the heat-related harmful reactions even in small amounts, is an improved processing stabilizer for polymers
- the invention relates to a mixture containing
- component 2 at least one compound of the general formula (V) [hereinafter referred to as component 2]
- Ri C L2 alkyl (linear or branched, possibly also containing heteroatoms N, O, P, S), C 5 . 30 cycloalkyl (possibly also containing heteroatoms N, O, P, S), C ⁇ . 30 alkylaryl, C 6 24 aryl, C 4 . 4 heteroaryl, C 6 2 aryl or C 4 2 heteroaryl (mono- or polysubstituted by groups d.-i ⁇ alkyl (linear or branched), C 5 12 cycloalkyl or d 18 alkoxy), R 2 C 4 . 2 alkyl (linear or branched, possibly also containing heteroatoms N, O, P, S), C 5 .
- cycloalkyl possibly also containing heteroatoms N, O, P, S
- d. 30 alkylaryl C 6 . 2 aryl, C 24 heteroaryl, C 6 24 aryl or C 4 . 24 heteroaryl (mono- or polysubstituted by groups d 18 alkyl (linear or branched), C 5, 12 cycloalkyl or d.i ⁇ alkoxy),
- R 3 is hydrogen, d 24 alkyl (linear or branched), C 3 12 cycloalkyl, d 24 alkenyl
- R 8 is hydrogen, d_ 20 alkyl (linear or branched), C 4 12 cycloalkyl or
- D d. 30 alkylene (linear, branched, possibly also containing heteroatoms N, O, P, S), C 2 . 30 alkyl idens (possibly also containing heteroatoms N, O, P, S), C 5 12 cycloalkylene (optionally also containing heteroatoms N, O, P, S), or C 6 . 2 arylene / C 4 . 24 heteroarylene (possibly also mono- or polysubstituted by d.-isalkyl (linear or branched), C 5 12 cycloalkyl or C, 18 alkoxy), -O-, -S-, r 3 to 6, the groups PRi in the formula (IV) being part of a
- Phosphacyclus are, indicated by * on the bonds originating from P,
- R / C 8 24 alkyl (linear or branched, possibly also containing heteroatoms N, O, P, S), C 6 12 cycloalkyl (optionally also containing heteroatoms N, O, P, S) C 2 24 alkylaryl, C 6 24 aryl or C 4 18 heteroaryl, C 6 24 aryl or heteroaryl (mono- or polysubstituted by groups 12 alkyl (linear or branched), C 5 8 cycloalkyl or C 1 12 alkoxy),
- R 2 'C 6 18 alkyl (linear or branched, possibly also containing heteroatoms N, O, P, S), C 5 12 cycloalkyl (optionally also containing heteroatoms NO, P, S) d isalkylaryl, C 6 2 aryl, C 4 18 heteroaryl, C 6 2 aryl / C 4 18 heteroaryl (one or polysubstituted by groups C 1-12 alkyl (linear or branched), C 5 . 8 cycloalkyl or d. 12 alkoxy),
- R 3 'C 1-2 oalkyl linear or branched
- C 4 . 8 cycloalkyl i.e. 20 alkenyl (mono- or polyunsaturated, linear or branched)
- R 8 ' is hydrogen, C 1-12 alkyl (linear or branched), C 4 . 8 cycloalkyl or
- Phosphacyclus are indicated by * on the bonds originating from P.
- R 1 "C 6. 2 aryl or C 4. 8 heteroaryl, C 6. 2 aryl / C 4. 8 heteroarylene (mono- or polysubstituted by groups Ci 12 alkyl (linear or branched), C 5 ⁇ cycloalkyl or 12 alkoxy )
- R 2 "C ⁇ i ⁇ alkyl (linear or branched), C 5 8 cycloalkyl, C n-18 alkylaryl, C 6 ⁇ 2 aryl,
- R 3 "d 1 e alkyl (linear or branched), C 5. 8 cycloalkyl, d 16 alkenyl (mono- or polyunsaturated, linear or branched),
- R “, R5", Re “, R7” hydrogen, Ci 16 alkyl (linear or branched), C 5 ⁇ cycloalkyl, i ⁇ alkenyl (mono- or polyunsaturated, linear or branched), carboxyl groups -COOR 8 ", succinyl groups -CH (COOR 8 ”) -CH 2 -COOR 8 ",
- R 8 is hydrogen, d salkyl (linear or branched) C 5 8 cycloalkyl or
- Phosphacyclus are indicated by * on the bonds originating from P.
- component 1 is t ⁇ phenylphosphane and component 2 is ⁇ -tocopherol
- component 1 is phenylphosphine and component 2 is 3,4-dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol,
- component 1 is tris (4-methylphenyl) phosphane and component 2 is 3,4-dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol,
- component 1 is T ⁇ s (4-methoxyphenyl) phosphane and component 2 is ⁇ -tocopherol
- component 1 is T ⁇ s (4-methoxyphenyl) phosphane and component 2 is 3,4-dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol,
- component 1 in which component 1 is tris (2-methylphenyl) phosphane and component 2 is 3,4-dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol
- component 1 in which component 1 is T ⁇ s (2-methoxyphenyl) phosphane and component 2 is ⁇ -tocopherol
- J in which component 1 is T ⁇ s (2-methoxyphenyl) phosphane and component 2 is 3,4-dihydro-
- component 1 is 1,3-bis (d ⁇ phenylphosph ⁇ no) propane and component 2 is ⁇ -tocopherol
- P in which component 1 1,3-b ⁇ s (d ⁇ phenylphosph ⁇ no) propane and component 2 is 3,4-di-hydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol
- Q in which component 11 is 1, 3- B ⁇ s (d ⁇ phenylphosph ⁇ no) -2,2-dimethyl-propane and
- Component 2 is ⁇ -tocopherol, R) in which component 1 is 1, 3-bis (d ⁇ phenylphosph ⁇ no) -2,2-dimethyl-propane and
- Component 2 is 3,4-dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol, S) in which component 1 is 1, 1, 1-tr ⁇ s (diphenylphosphinomethyl) and component 2 is ⁇ -tocopherol, T) in which component 1 is 1, 1, 1-tr ⁇ s (d ⁇ phenylphosph ⁇ nomethyl) ethane and component 2
- component 1 is 1, 1, 1-tr ⁇ s (d ⁇ phenylphosph ⁇ nomethyl) propane and component 2 ⁇ - Tocopherol is, V) in which component 1 1, 1, 1 -tr ⁇ s (d ⁇ phenylphosph ⁇ nomethyl) propane and component 2
- the quantitative ratios of component 1 to component 2 in the mixture according to the invention preferably comprise 50: 1 to 2: 1, preferably from 20 ' to 1, 5.1, particularly preferably from 15 1 to 1: 1.
- Components 1 and 2 can each consist of one or more compounds of the same component group
- the amounts of the mixtures of components 1 and 2 are, based on the polymeric material to be stabilized, 0.001 to 2% by weight, preferably 0.005 to 1% by weight, particularly preferably 0.0075 to 0.75% by weight.
- the mixtures of components 1 and 2 can be obtained by simple mixing, by mixing in the melt, by dissolving or dispersing one component in the liquid or melted other component, by mixing two melts or by melting together, if necessary, each followed by a cooling step getting produced.
- Mixtures according to the invention are likewise obtained by mixing and concentrating solutions of the components in suitable solvents.
- the mixtures can be prepared both as a batch process in suitable apparatuses, such as various mixers or reactors, etc., or continuously, e.g. in extruders, continuous mixers, kneaders or roller mills, then - if it is still necessary - a suitable commercial form can be produced, for example, by compacting, pelleting, pressing, extruding or in some other way
- a method for stabilizing polymeric materials against thermo-oxidative degradation comprises the addition and incorporation of a stabilizing amount of the mixture according to the invention in solid or molten form, in solution (preferably as a liquid concentrate), in a mixture with others Additives in the form of powder blends, extrudates or other commercial forms, as a compound (mixture of a polymer and a mixture according to the invention and further additives, such as acid scavengers (eg metal soaps, dihydrotalcites, etc.) or hindered phenols, in the form of powder blends, Extrudates or other Commercial forms) or as a solid masterbatch composition in amounts such that a stabilizer concentration of 0.001 to 2% by weight, preferably 0.005 to 1% by weight, particularly preferably 0.0075 to 0.75% by weight, based on that to be stabilized polymeric material is achieved
- a stabilizer concentration of 0.001 to 2% by weight preferably 0.005 to 1% by weight, particularly preferably 0.0075 to
- Such a liquid concentrate comprises 10 to 80% by weight of a mixture according to the invention and 90 to 20% by weight of a solvent
- Such a masterbatch composition (also called a solid basic mixture) comprises 5 to 80% by weight, preferably 10 to 70% by weight, particularly preferably 15 to 40% by weight of a mixture according to the invention and 95 to 20% by weight, preferably 90 to 30 % By weight, particularly preferably 85 to 60% by weight, of a polymeric material which is identical or compatible with the polymeric material to be stabilized.
- a corresponding compound contains the same amounts by weight of the mixture according to the invention as a masterbatch composition, but the amount by weight of the polymeric material is reduced according to the amount of other additives
- mixtures according to the invention of components 1 and 2 can be used as processing stabilizers for polymeric materials, preferably for
- Polymers of mono- and diolefins for example polypropylene, polyisobutylene, polybutene-1, poly-4-methylpentene-1, polyisoprene or polybutadiene as well as polymers of cycloolefins such as cyclopentene or norbornene, and also polyethylene (which may optionally be crosslinked), for B High-density polyethylene (HDPE), low-density polyethylene (LDPE), linear low-density polyethylene (LLDPE), branched low-density polyethylene (VLDPE).
- Polyolefins, ie polymers of monoolefins, in particular polyethylene and polypropylene can be produced by various processes, in particular by the following methods
- a) radical (usually at high pressure and temperature) b) by means of a catalyst the catalyst usually containing one or more metals from group IVb, Vb, Vlb or VIII.
- These metals usually have one or more ligands such as oxides, halides, alcoholates, esters, ethers, amines, alkyls, alkenyls and / or Aryls, which can be either - ⁇ - or ⁇ -coordinated.
- These metal complexes can be free or fixed on supports such as activated magnesium chloride, titanium chloride, aluminum oxide or silicon oxide.
- These catalysts can be soluble or insoluble in the polymerization medium.
- the catalysts as such can be in the Polymerization be active, or other activators can be used, such as metal alkyls, metal hydrides, metal alkyl halides,
- Metal alkyl oxides or metal alkyl oxanes where the metals are elements of groups la, Ha and / or purple.
- the activators can be modified, for example, with further ester, ether, amine or silyl ether groups.
- These catalyst systems are commonly known as Phillips, Standard Oil Indiana, Ziegler (Natta), TNZ (DuPont), metallocene or single site catalysts (SSC)
- Mixtures of the polymers mentioned under 1) for example mixtures of polypropylene with polyisobutylene, polypropylene with polyethylene (for example PP / HDPE, PP / LDPE, PP / LLDPE) and mixtures of different types of polyethylene (for example LDPE / HDPE)
- Copolymers of mono- and diolefins with one another or with other vinyl monomers such as, for example, ethylene-propylene copolymers, linear low-density polyethylene (LLDPE) and mixtures thereof with low-density polyethylene (LDPE), propylene-butene-1 copolymers, propylene-isobutylene Copolymers, ethylene-butene-1 copolymers, ethylene-hexene copolymers, ethylene-methylpentene copolymers, ethylene-heptene copolymers, ethylene-octene copolymers, propylene-butadiene copolymers, isobutylene and isoprene copolymers, ethylene Alkyl acrylate copolymers, ethylene-alkyl methacrylate copolymers, ethylene-vinyl acetate copolymers and their copolymers with carbon monoxide, or ethylene-acrylic acid copolymers and their salts (
- Hydrocarbon resins e.g. BC 5 9
- hydrogenated modifications thereof e.g. tackifier resins
- Polystyrene poly- (p-methylstyrene), poly- ( ⁇ -methylstyrene)
- Copolymers of styrene or .alpha.-methylstyrene with dienes or acrylate derivatives such as, for example, styrene-butadiene, styrene-acrylonitrile, styrene-alkyl methacrylate, styrene-butadiene-alkyl acrylate and methacrylate, styrene-maleic anhydride, styrene-acrylonitrile methacrylate, mixtures of high impact from styrene copolymers and another polymer, such as a polyacrylate, a diene polymer or an ethylene-propylene-diene terpolymer, and also block copolymers of styrene, such as styrene-butadiene-styrene, styrene-isoprene-styrene , Styrene-ethylene / butylene-sty
- Graft copolymers of styrene or .alpha.-methylstyrene such as, for example, styrene on polybutadiene, styrene on polybutadiene-styrene or polybutadiene-acrylonitrile copolymers, styrene and acrylonitrile (or methacrylonitrile) on polybutadiene, styrene, acrylonitrile and methylmethane acrylate on polybutadiene on polybutadiene, styrene, acrylonitrile and maleic anhydride or maleimide on polybutadiene, styrene and maleic acid imide on polybutadiene, styrene and alkyl acrylates or alkyl methacrylates on polybutadiene, styrene and acrylonitrile on ethylene-propylene diene terpolymers, styrene and acryl
- Halogen-containing polymers such as, for example, polychloroprene, chlorinated rubber, chlorinated or chlorosulfonated polyethylene, copolymers of ethylene and chlorinated ethylene, epichlorohydrin and copolymers, in particular polymers of halogen-containing vinyl compounds, such as, for example, polyvinyl chloride, polyvinylidene chloride, polyvinylfluoride, polyvinylidene fluoride and vinyl copolymers such as vinyl chloride and vinyl chloride such as vinyl chloride Vinylidenchlo ⁇ d acetate Polymers derived from ⁇ , ⁇ -unsaturated acids and their derivatives, such as polyacrylates and polymethacrylates, impact-modified polymethyl methacrylates, polyacrylamides and polyacrylonitriles with butyl acrylate
- Copolymers of the monomers mentioned under 9) with one another or with other unsaturated monomers such as, for example, acrylonitrile-butadiene copolymers, acrylonitrile-alkyl acrylate copolymers, acrylonitrile-alkoxyalkylacrylate copolymers, acrylonitrile-vinyl halide copolymers or acrylonitrile-teralkylene-acrylate methacrylate
- Polymers derived from unsaturated alcohols and amines or their acyl derivatives or acetals such as polyvinyl alcohol, polymer acetate, stearate, benzoate, maleate, polyvinyl butyral, polyallyl phthalate, polyallyl melamine, and their copolymers with olefins mentioned in point 1
- cyclic ethers such as polyalkylene glycols, polyethylene oxide, polypropylene oxide or their copolymers with bisglycidyl ethers
- Polyacetals such as polyoxymethylene, and those polyoxymethylenes which contain comonomers, such as, for example, ethylene oxide, polyacetals which have been modified with thermoplastic polyurethanes, acrylates or MBS
- Polyamides and copolyamides derived from diamines and dicarboxylic acids and / or from aminocarboxylic acids or the corresponding lactams such as polyamide 4, polyamide 6, polyamide 6/6, 6/10, 6/9, 6/12, 4/6, 12 / 12, polyamide 1 1, polyamide 12, aromatic polyamides starting from m-xylene, diamine and adipic acid, polyamides made from hexamethylene diamine and iso- and / or terephthalic acid and optionally an elastomer as a modifier, for example poly-2 4 4- t ⁇ methylhexamethylene terephthalamide or Poly-m-pheny-isophthalamide block copolymers of the above-mentioned polyamides with polyolefins olefin Copolymers, ionomeric or chemically bonded or grafted elastomers, or with polyethers, such as with polyethylene glycol, polypropylene glycol or polytetramethylene glycol,
- Polyesters derived from dicarboxylic acids and dialcohols and / or from hydroxycarboxylic acids or the corresponding lactones such as polyethylene terephthalate, polybutylene terephthalate, poly-1, 4-dimethylolcyclohexane terephthalate, polyhydroxybenzoates, and block polyether esters derived from polyethers with hydroxyl end groups furthermore polyesters modified with polycarbonates or MBS
- Crosslinkable acrylic resins derived from substituted acrylic acid esters such as epoxy acrylates, urethane acrylates or polyester acrylates
- Natural polymers such as cellulose, natural rubber, gelatin, and their polymer-homologously chemically modified derivatives, such as cellulose acetates, propionates and butyrates, or the cellulose ethers, such as methyl cellulose, as well as rosins and derivatives
- polyblends of the aforementioned polymers, such as PP / EPDM, polyamide / EPDM or ABS, PVC / EVA, PVC / ABS, PVC / MBS, PC / ABS, PBTP / ABS, PC / ASA, PC / PBT, PVC / CPE, PVC / acrylates, POM / thermoplastic PUR, PC / thermoplastic PUR, POM / acrylate, POM / MBS, PPO / HIPS, PPO / PA 6 6 and copolymers, PA / HDPE, PA / PP, PA / PPO
- Natural and synthetic organic substances which are pure monomeric compounds or mixtures thereof, for example mineral oils, animal or vegetable fats, oils and waxes, or oils, waxes and fats based on synthetic esters (e.g. phthalates, adipates, phosphates or tmellitates) , as well as mixtures of synthetic esters with mineral oils in any weight ratios, such as those used as spin finishes, and their aqueous emulsions
- Particularly preferred polymers to be stabilized are polyolefins, polyurethanes and polycarbonates
- additives such as antioxidants, light stabilizers (UV absorbers and / or HALS compounds and / or UV quenchers), metal deactivators, peroxide-destroying compounds, polyamide stabilizers, basic co-stabilizers, nucleating agents, fillers, reinforcing agents, plasticizers, Lubricants, emulsifiers, pigments and dyes, optical brighteners, flame retardants, antistatic agents, blowing agents, peroxides, hydroxylam e, polyalcohols, nitrones, color improvers, thiosynergists, rheology-additive dispersants, etc.
- additives can be added to the polymers before, together with or after addition of the mixture according to the invention. Both these additives and the mixture according to the invention can be metered in as a solid, in solution or melt and also in the form of solid or liquid mixtures or masterbatches / concentrates in batch mode or continuously
- the invention also encompasses all products, obtained by a molding process, from the above-mentioned polymers, which contain a mixture according to the invention and at least one of the above-mentioned further additives.
- ⁇ -tocopherol (Ronotec 201, from Hoffman-La Röche) (component 2)
- component 2 0.01 parts of ⁇ -tocopherol (Ronotec 201, from Hoffman-La Röche) (component 2) are mixed in a Kenwood mixer and then by gentle extrusion on a single-screw extruder (from Collm, 210 ° C., 80 revolutions / min, Compression ratio 1 3, nozzle 4 mm) homogenized and the polymer strand obtained in this way granulated
- the stabilized polymers are subjected to a five-fold extrusion at 270 ° C.
- melt flow index (MFI, Melt Flow Index) is determined according to ASTM 1238 Cond L (230 ° C7 2 16 kg)
- a further polymer stabilized according to the invention is made from 100.00 parts of polypropylene (Eltex P HL 001 PF, Solvay)
- Hostanox O-10 hindered phenol, Cla ⁇ ant AG
- a further polymer stabilized according to the invention is made from 100.00 parts of polypropylene (Eltex P HL 001 PF, Solvay)
- Hostanox 0-10 hindered phenol, Cla ⁇ ant AG
- Example 2 Analogously to Example 1, a polymer stabilized according to the prior art and made from 100.00 parts of polypropylene (Eltex P HL 001 PF, Solvay) is used for comparison purposes.
- Hostanox 0-10 hindered phenol Fa Cla ⁇ ant AG
- Example 2 Analogously to Example 1, a polymer stabilized according to the prior art and made from 100.00 parts of polypropylene (Eltex P HL 001 PF, Solvay) is used for comparison purposes.
- Hostanox O-10 hindered phenol, Cla ⁇ ant AG
- Example 2 Analogously to Example 1, a polymer stabilized according to the prior art and made from 100.00 parts of polypropylene (Eltex P HL 001 PF, Solvay) is used for comparison purposes.
- Hostanox 0-10 hindered phenol, Cla ⁇ ant AG
- Example 2 Analogously to Example 1, a polymer stabilized according to the prior art and made from 100.00 parts of polypropylene (Eltex P HL 001 PF, Solvay) is used for comparison purposes.
- Hostanox 0-10 hindered phenol, Cla ⁇ ant AG
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)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Abstract
Description
Claims
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU0204025A HU224557B1 (hu) | 1999-12-20 | 2000-12-18 | Foszfán(oka)t és krománszármazéko(ka)t tartalmazó elegyek, valamint eljárás polimerek stabilizálására |
AT00983432T ATE264884T1 (de) | 1999-12-20 | 2000-12-18 | Mischungen aus phosphanen und chroman-derivaten |
CA002392152A CA2392152A1 (en) | 1999-12-20 | 2000-12-18 | Mixtures of phosphanes and chromane derivatives |
JP2001547214A JP2003518184A (ja) | 1999-12-20 | 2000-12-18 | ホスファン及びクロマン誘導体の混合物 |
DE50006192T DE50006192D1 (de) | 1999-12-20 | 2000-12-18 | Mischungen aus phosphanen und chroman-derivaten |
MXPA02005730A MXPA02005730A (es) | 1999-12-20 | 2000-12-18 | Mezclas de fosfanos y derivados de cromano. |
DK00983432T DK1268646T3 (da) | 1999-12-20 | 2000-12-18 | Blandinger af phosphaner og chromanderivater |
US10/149,682 US7083743B2 (en) | 1999-12-20 | 2000-12-18 | Mixture of phosphanes and chromane derivatives |
EP00983432A EP1268646B1 (de) | 1999-12-20 | 2000-12-18 | Mischungen aus phosphanen und chroman-derivaten |
BR0016519-0A BR0016519A (pt) | 1999-12-20 | 2000-12-18 | Mistura de fosfanos e derivados de cromano |
AU20186/01A AU2018601A (en) | 1999-12-20 | 2000-12-18 | Mixtures of phosphanes and chromane derivatives |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19961464.4 | 1999-12-20 | ||
DE19961464A DE19961464A1 (de) | 1999-12-20 | 1999-12-20 | Mischungen aus Phosphanen und Chroman-Derivaten |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001046310A1 true WO2001046310A1 (de) | 2001-06-28 |
Family
ID=7933431
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IB2000/001897 WO2001046310A1 (de) | 1999-12-20 | 2000-12-18 | Mischungen aus phosphanen und chroman-derivaten |
Country Status (14)
Country | Link |
---|---|
EP (1) | EP1268646B1 (de) |
JP (1) | JP2003518184A (de) |
KR (1) | KR100705154B1 (de) |
AT (1) | ATE264884T1 (de) |
AU (1) | AU2018601A (de) |
BR (1) | BR0016519A (de) |
CA (1) | CA2392152A1 (de) |
DE (2) | DE19961464A1 (de) |
DK (1) | DK1268646T3 (de) |
ES (1) | ES2219424T3 (de) |
HU (1) | HU224557B1 (de) |
MX (1) | MXPA02005730A (de) |
PT (1) | PT1268646E (de) |
WO (1) | WO2001046310A1 (de) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102013215441A1 (de) | 2013-08-06 | 2015-02-12 | Henkel Ag & Co. Kgaa | Metallvorbehandlungszusammensetzungen umfassend Silane und Organophosphonsäuren |
DE102013215440A1 (de) | 2013-08-06 | 2015-02-12 | Henkel Ag & Co. Kgaa | Metallvorbehandlung mit sauren wasserhaltigen Zusammensetzungen umfassend Silane |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI240734B (en) * | 2001-06-19 | 2005-10-01 | Clariant Int Ltd | Phosphorus compounds as stabilizers |
KR100531042B1 (ko) * | 2004-01-26 | 2005-11-25 | 주식회사 효성 | 의료용 폴리프로필렌 수지 조성물 |
DE102004000058A1 (de) * | 2004-12-01 | 2006-06-08 | Kuraray Specialities Europe Gmbh | Organophosphin-stabilisierte Polymermischungen |
ATE552290T1 (de) * | 2007-09-04 | 2012-04-15 | Basf Se | Cyclische phosphine als flammhemmer |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3637907A (en) * | 1969-02-26 | 1972-01-25 | Phillips Petroleum Co | Polyolefins stabilized with diphosphines |
US5488079A (en) * | 1993-03-25 | 1996-01-30 | Sandoz Ltd. | Polyolefin stabilization |
WO1997049758A1 (en) * | 1996-06-27 | 1997-12-31 | Clariant International Limited | Stabilizer compositions |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3010505A1 (de) * | 1980-03-19 | 1981-10-01 | Basf Ag, 6700 Ludwigshafen | Chromanderivate, verfahren zu ihrer herstellung, ihre verwendung als stabilisatoren von organischen materialien sowie diese stabilisatoren enthaltende organische materialien |
DE3855842D1 (de) * | 1987-12-18 | 1997-04-30 | Bayer Ag | Verwendung von Phosphanen und/oder Diphosphanen bei der Herstellung von Kunststoffen auf Isocyanatbasis |
GB9121575D0 (en) * | 1991-10-11 | 1991-11-27 | Sandoz Ltd | Improvements in or relating to organic compounds |
DE4445786A1 (de) * | 1994-12-21 | 1996-06-27 | Bayer Ag | Arylphosphin-haltige Polycarbonate |
DE19526471A1 (de) * | 1995-07-20 | 1997-01-23 | Basf Ag | Chromanderivate |
DE19638924A1 (de) * | 1995-09-28 | 1997-04-03 | Sandoz Ag | Phosphorverbindungen |
DE19627809A1 (de) * | 1996-07-11 | 1998-01-15 | Henkel Kgaa | Verfahren zur Herstellung von oxidationsstabilen Waschmittelkomponenten, so erhaltene Waschmittel sowie deren Verwendung |
DE19629691A1 (de) * | 1996-07-23 | 1998-01-29 | Bayer Ag | Verarbeitungsstabilisierung von ABS mit Arylphosphiten |
ES2149678B1 (es) * | 1997-03-06 | 2001-05-16 | Ciba Sc Holding Ag | Estabilizacion de policarbonatos, poliesteres y policetonas. |
-
1999
- 1999-12-20 DE DE19961464A patent/DE19961464A1/de not_active Withdrawn
-
2000
- 2000-12-18 AT AT00983432T patent/ATE264884T1/de not_active IP Right Cessation
- 2000-12-18 BR BR0016519-0A patent/BR0016519A/pt not_active Application Discontinuation
- 2000-12-18 JP JP2001547214A patent/JP2003518184A/ja not_active Withdrawn
- 2000-12-18 KR KR1020027007878A patent/KR100705154B1/ko not_active IP Right Cessation
- 2000-12-18 PT PT00983432T patent/PT1268646E/pt unknown
- 2000-12-18 ES ES00983432T patent/ES2219424T3/es not_active Expired - Lifetime
- 2000-12-18 MX MXPA02005730A patent/MXPA02005730A/es active IP Right Grant
- 2000-12-18 DE DE50006192T patent/DE50006192D1/de not_active Expired - Fee Related
- 2000-12-18 HU HU0204025A patent/HU224557B1/hu not_active IP Right Cessation
- 2000-12-18 DK DK00983432T patent/DK1268646T3/da active
- 2000-12-18 AU AU20186/01A patent/AU2018601A/en not_active Abandoned
- 2000-12-18 CA CA002392152A patent/CA2392152A1/en not_active Abandoned
- 2000-12-18 EP EP00983432A patent/EP1268646B1/de not_active Expired - Lifetime
- 2000-12-18 WO PCT/IB2000/001897 patent/WO2001046310A1/de active Search and Examination
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3637907A (en) * | 1969-02-26 | 1972-01-25 | Phillips Petroleum Co | Polyolefins stabilized with diphosphines |
US5488079A (en) * | 1993-03-25 | 1996-01-30 | Sandoz Ltd. | Polyolefin stabilization |
WO1997049758A1 (en) * | 1996-06-27 | 1997-12-31 | Clariant International Limited | Stabilizer compositions |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102013215441A1 (de) | 2013-08-06 | 2015-02-12 | Henkel Ag & Co. Kgaa | Metallvorbehandlungszusammensetzungen umfassend Silane und Organophosphonsäuren |
DE102013215440A1 (de) | 2013-08-06 | 2015-02-12 | Henkel Ag & Co. Kgaa | Metallvorbehandlung mit sauren wasserhaltigen Zusammensetzungen umfassend Silane |
Also Published As
Publication number | Publication date |
---|---|
BR0016519A (pt) | 2002-09-17 |
KR100705154B1 (ko) | 2007-04-10 |
EP1268646B1 (de) | 2004-04-21 |
HUP0204025A2 (hu) | 2003-04-28 |
MXPA02005730A (es) | 2003-01-28 |
AU2018601A (en) | 2001-07-03 |
EP1268646A1 (de) | 2003-01-02 |
KR20020063241A (ko) | 2002-08-01 |
DK1268646T3 (da) | 2004-08-02 |
HU224557B1 (hu) | 2005-10-28 |
DE50006192D1 (de) | 2004-05-27 |
ES2219424T3 (es) | 2004-12-01 |
JP2003518184A (ja) | 2003-06-03 |
ATE264884T1 (de) | 2004-05-15 |
HUP0204025A3 (en) | 2004-08-30 |
PT1268646E (pt) | 2004-08-31 |
DE19961464A1 (de) | 2001-06-21 |
CA2392152A1 (en) | 2001-06-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE60119509T2 (de) | Verfahren zur Reduzierung des Moleculargewichts von Polypropylen unter Verwendung von Hydroxylaminestern | |
DE69929242T2 (de) | Stabilisierte thermoplastische zusammensetzungen | |
JP4340985B2 (ja) | N,N’,N’’’−トリス{2,4−ビス[(1−ヒドロカルビルオキシ−2,2,6,6−テトラメチルピペリジン−4−イル)アルキルアミノ]−s−トリアジン−6−イル}−3,3’−エチレンジイミノジプロピルアミン、その異性体および架橋型誘導物ならびにそれにより安定化されたポリマー組成物 | |
DE60009036T2 (de) | Synthetische polymere enthaltend additivmischungen mit erhöhtem effekt | |
EP0905180B1 (de) | Staubfreie epoxidhaltige Stabilisatorgranulate und Verfahren zur Herstellung | |
JP4787160B2 (ja) | 難燃性組成物 | |
EP0905181B1 (de) | Stabilisatorgemisch für organische Materialien | |
EP0723990A1 (de) | Synergistisches Stabilisatorgemisch | |
EP0745646B1 (de) | Auf Trägermittel fixierte Antioxidantien und Lichtschutzmittel als Füllstoffe und Stabilisatoren | |
DE19882401B3 (de) | Blockoligomere, enthaltend 1-Kohlenwasserstoffoxy-2,2,6,6-tetramethyl-4-piperidyl-Gruppen als Stabilisatoren für organische Materialien | |
EP0981530B1 (de) | Verbindungen auf basis von polyalkyl-1-oxa-diazaspirodecan-verbindungen | |
EP0878502A2 (de) | Formulierungen von Vitamin E zur Stabilisierung von polymeren organischen Materialien | |
DE19735255A1 (de) | Synergistisches Stabilisatorgemisch auf Basis von Polyalkyl-1-oxa-diazaspirodecan-Verbindungen | |
DE69307734T2 (de) | Amorphe feste modifikation von 2,2', 2"-nitrilo(triäthyl-tris-(3,3, 5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl)phosphit | |
EP0727410A1 (de) | Bisphenolesterderivate | |
EP0244362B1 (de) | Mit Aminoxysilanen stabilisierte Zusammensetzungen | |
DE60114626T2 (de) | Mischungen aus phosphor-enthaltenden verbindungen zur verwendung als polymerstabilsatoren | |
WO2001046310A1 (de) | Mischungen aus phosphanen und chroman-derivaten | |
DE19703047A1 (de) | Synergistisches Gemisch aus einem 2,4-Dimethyl-6-s-alkylphenol und einem sterisch gehinderten Phenol | |
DE19959619B4 (de) | Sterisch gehinderte Aminverbindungen und damit stabilisierte organische Materialien | |
DE19882402B9 (de) | Blockoligomere, enthaltend 1-Kohlenwasserstoffoxy-2,2,6,6-tetramethyl-4-piperidyl-Gruppen als Stabilisatoren für organische Materialien | |
DE10004158A1 (de) | Stabilisatorzusammensetzung | |
EP0707035B1 (de) | HALS-Phosphorinane als Stabilisatoren | |
US7083743B2 (en) | Mixture of phosphanes and chromane derivatives | |
DE69821261T2 (de) | Morpholin-endständige, gehinderte amin-substituierte aminotriazine und deren verwendung als lichtstabillisatoren |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AU BR CA HU JP KR MX US ZA |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2392152 Country of ref document: CA |
|
WWE | Wipo information: entry into national phase |
Ref document number: PA/a/2002/005730 Country of ref document: MX |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2000983432 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 10149682 Country of ref document: US |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1020027007878 Country of ref document: KR |
|
ENP | Entry into the national phase |
Ref country code: JP Ref document number: 2001 547214 Kind code of ref document: A Format of ref document f/p: F |
|
WWP | Wipo information: published in national office |
Ref document number: 1020027007878 Country of ref document: KR |
|
WWP | Wipo information: published in national office |
Ref document number: 2000983432 Country of ref document: EP |
|
WWG | Wipo information: grant in national office |
Ref document number: 2000983432 Country of ref document: EP |
|
DPE2 | Request for preliminary examination filed before expiration of 19th month from priority date (pct application filed from 20040101) |