WO1998036023A1 - Composition de matieres plastiques presentant une resistance accrue aux intemperies - Google Patents

Composition de matieres plastiques presentant une resistance accrue aux intemperies Download PDF

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Publication number
WO1998036023A1
WO1998036023A1 PCT/NL1998/000088 NL9800088W WO9836023A1 WO 1998036023 A1 WO1998036023 A1 WO 1998036023A1 NL 9800088 W NL9800088 W NL 9800088W WO 9836023 A1 WO9836023 A1 WO 9836023A1
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Prior art keywords
tetramethyl
plastics composition
bridgehead
bis
piperidinyl
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PCT/NL1998/000088
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English (en)
Dutch (nl)
Inventor
Pieter Gijsman
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Dsm N.V.
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Application filed by Dsm N.V. filed Critical Dsm N.V.
Priority to BR9807679-5A priority Critical patent/BR9807679A/pt
Priority to AU61231/98A priority patent/AU6123198A/en
Priority to IL13132598A priority patent/IL131325A0/xx
Priority to JP53561198A priority patent/JP2001511834A/ja
Priority to CA002280158A priority patent/CA2280158A1/fr
Priority to EP98905864A priority patent/EP0960160A1/fr
Publication of WO1998036023A1 publication Critical patent/WO1998036023A1/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
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432—Six-membered rings
    • C08K5/3435—Piperidines
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3477—Six-membered rings

Definitions

  • the invention relates to a plastics composition containing a polymer and at least one hindered-amine light stabilizer.
  • a hindered-amine light stabilizer will be referred to as a HALS compound.
  • a plastics composition containing a polymer and at least one HALS compound is disclosed in US-A- 3,904,581.
  • Patent Specification US-A-3 , 904 , 581 describes a plastics composition which contains a polymer and a 4-aminopiperidine compound, which is a HALS compound, as a result of which the plastics composition is stabilized against degradation caused by heat and light. It is generally known that the stabilization of a plastics composition against degradation caused by heat and light, in particular against degradation caused by UV radiation, improves the weather resistance of the plastics composition, as a result of which the plastics composition becomes suitable for particular applications, for example for outdoor applications.
  • the object of the invention is to provide a plastics composition which has such improved weather resistance.
  • the plastics composition according to the invention contains a polymer, at least one HALS compound and at least one bridged amine compound having at least one N-bridgehead.
  • a plastics composition which contains a polymer, at least one HALS compound and at least one bridged amine compound having at least one N-bridgehead has a weather resistance which is appreciably better than that of the known plastics composition which does not contain the bridged amine compound having at least one N-bridgehead. It has also been found that a plastics composition which contains a polymer, at least one HALS compound and at least one bridged amine compound having at least one N-bridgehead has a weather resistance that is better than would be expected on the basis of the sum of the contributions of the HALS compound and the bridged amine compound.
  • DE 2637193 describes that the aforementioned compounds (I) are also effective in the presence of the usual stabilizers such as antioxidants, UV absorbers, light stabilizers, phosphite stabilizers, metal compounds, epoxy stabilizers, polyhydric alcohols, antistatic agents, flame retardants and pigments. Sterically hindered piperidine compounds are mentioned as examples of the UV absorbers and/or light stabilizers. It is nowhere apparent from DE 2637193 that compounds having the general formula (I) would improve the effect of the usual stabilizers, let alone that there would be a synergistic effect between compounds having the general formula (I) and HALS stabilizers. Compounds having the general formula (I) are excluded from the plastics composition according to the invention.
  • the usual stabilizers such as antioxidants, UV absorbers, light stabilizers, phosphite stabilizers, metal compounds, epoxy stabilizers, polyhydric alcohols, antistatic agents, flame retardants and pigments. Sterically hindered piperidine compounds are mentioned as examples
  • a xenon test is employed as a measure of the weather resistance.
  • the xenon test determines a plastics composition's resistance to degradation when exposed to light from a filtered (borosilicate glass) xenon lamp at a black panel temperature of 62°C having an intensity of 0.35 W-m "2 -nm "1 , at a wavelength of 340 nm and a relative humidity of 55% by volume in a wet/dry cycle of 18 minutes wet and 102 minutes dry.
  • the degradation of the plastics composition is measured as the difference in the carbonyl absorption at 1713 cm “1 and the absorption at 1860 cm “1 as a function of the time for which the plastics composition is subjected to said combination of light, temperature and humidity.
  • the weather resistance is expressed as the time for which a plastics composition is subjected to said combination of light, temperature and humidity and at which the difference between the measured carbonyl absorptions is less than a certain value to be chosen beforehand. In the xenon test employed here, this value is 0.10 for the films and 0.50 for plates.
  • Ri up to and including R 5 are herein independent substituents; examples of suitable substituents are hydrogen, ether, ester, amine, amide, alkyl, alkenyl, alkynyl, aralkyl, cycloalkyl and aryl groups, which substituents may in turn contain functional groups; examples of functional groups are alcohols, ketones, anhydrides, imines, siloxanes, ethers, carboxyl groups, aldehydes, esters, amides, imides, amines, nitriles, ethers, urethanes and any combination thereof.
  • a hindered-amine light stabilizer may also form part of a polymer.
  • the HALS compound chosen is a compound derived from a substituted piperidine compound, in particular any compound which is derived from an alkyl-substituted piperidyl, piperidinyl or piperazinone compound and substituted alkoxypiperidinyl compounds .
  • a substituted piperidine compound in particular any compound which is derived from an alkyl-substituted piperidyl, piperidinyl or piperazinone compound and substituted alkoxypiperidinyl compounds . Examples of such compounds are :
  • N,N' -1, 6-hexanediylbis [N- (2 , 2 , 6 , 6- tetramethyl -4 -piperidinyl (Uvinul ⁇ 4050H) .
  • HALS PB-41 (Clariant Huningue S.A.)
  • Nylostab ® S-EED (Clariant Huningue S.A.) 3-dodecyl-l- (2,2,6, 6 -tetramethyl-4 -piperidyl) - pyrrolidin-2 , 5-dione
  • di- (2,2,6,6- tetra ethyl-4 -piperidyl) sebacate also known under the tradename of Tinuvin R 770
  • oligomer of N-(2- hydroxyethyl) -2 , 2, 6, 6-tetramethyl-4-piperidinol and succinic acid (Tinuvin ® 622); bis- (l-octyloxy-2 , 2 , 6 , 6- tetramethyl -4 -piperidinyl) sebacate (Tinuvin ® 123); bis - (1,2,2,6, 6 -pentamethyl -4 -piperidinyl ) sebacate (Tinuvin ® 765); N, N' -bis- (2 , 2 , 6 , 6 -tetramethyl-4 - piperidyl) -hexane-1, 6 -diamine (Chimassorb ® T5); poly ( (6-morpholine-S-tri
  • HALS 7 D-glucitol, 1, 3 :2 , 4-bis-O- (2, 2 , 6, 6 -tetramethyl -4- piperidinylidene) (HALS 7) - oligomer of 7-oxa-3,20- diazadispiro [5.1.11.2] heneicosan-21-one, 2,2,4,4- tetramethyl-20- (oxiranylmethyl) (Hostavin ® N30)
  • the bridged amine compound having at least one N-bridgehead that can be used within the scope of this invention is preferably a compound derived from a compound having the general formula 1 or 2 (see formula sheet) , where Mi to M 4 are bridgeheads and each bridgehead is chosen independently of one another from carbon, nitrogen, silicon or phosphorus, with the proviso that at least one bridgehead should always be a nitrogen atom and carbon and silicon may be substituted; an N-bridgehead is defined as a bridgehead which is a nitrogen atom; Di, D m , D__, D Q , D p and D q here each stand for a chain having a length of 1 to 20 atoms, the number of atoms of which the chains are made up being equal to 1, m, n, o, p and q, each number of atoms and type of atom to be chosen independently of one another, and the chains being capable of having different lengths and being capable of being made up of different types of atoms.
  • the chains may also contain side groups, the number of atoms in the side groups not being included in the number of atoms of the chain. Suitable choices for the atoms of which the chains are made up are carbon, nitrogen, oxygen, silicon and phosphorus. Preferably the chains are made up of 1 to 3 carbon atoms .
  • the bridged amine compound having at least one N-bridgehead is used with a HALS compound in a ratio, relative to the amount of HALS compound, of between approximately 1:20 (m.m) and approximately 20:1 (m.m), more preferably in a ratio of between approximately 1:10 (m.m) and approximately 10:1 (m:m) , most preferably in a ratio of between approximately 1:5 (m:m) and approximately 5:1 (m:m) .
  • the weather resistance is better than is expected on the basis of the amounts of the bridged amine compound having at least one N-bridgehead and the HALS compound present.
  • the amount of bridged amine compound having at least one N-bridgehead that can be used in the plastics composition may vary within a wide range, which can be easily determined by an average person skilled in the art.
  • the range may vary depending on for example the type of polymer, the type of HALS compound, the other additives in the additives package, the weather resistance to be realized or in general the type of plastics composition, its properties and its specific application.
  • the bridged amine compound having at least one N-bridgehead to be present in the plastics composition in an amount, relative to the amount of polymer in the plastics composition, of, preferably, between approximately 0.01% by weight and approximately 10.0% by weight, more preferably in an amount of between 0.05% by weight and 5% by weight, most preferably in an amount of between 0.1% by weight and 2.5% by weight.
  • the bridged amine compound having at least one N-bridgehead is chosen so that a plastics composition is obtained having a weather resistance measured with the aid of the xenon test which is higher than approximately 500 hours, more preferably higher than approximately 750 hours, and most preferably higher than approximately 1000 hours.
  • Suitable choices for the bridged amine compound having at least one N-bridgehead are:
  • R and R' are independent substituents; examples of suitable substituents are hydrogen, ether, ester, amine, amide, alkyl, alkenyl, alkynyl, aralkyl, cycloalkyl and aryl groups, which substituents may in turn contain functional groups; examples of functional groups are alcohols, ketones, anhydrides, imines, siloxanes, ethers, carboxyl groups, aldehydes, esters, amides, imides, amines, nitriles, ethers, urethanes and any combination thereof.
  • the substituent may moreover connect several of the I and/or II compounds to one another.
  • - derivatives obtained in a reaction of 7-amino-l, 3 5- triazadamantane with compounds containing one or more functional groups. Examples of these functional groups are: aldehydes, acids, esters, amides, ketones, anhydrides and isocyanates.
  • - triazadamantane derivatives that are bound to a polymer (preferably a polyolefin) with the aid of an imide functionality;
  • HMTA and DABCO are easy to obtain commercially or are easy to prepare using generally known processes .
  • HMTA for example, can easily be prepared from the cheap and easily obtainable basic raw materials ammonia and formaldehyde.
  • the bridged amine compound having at least one N-bridgehead is preferably used as a salt, more preferably as an ammonium salt.
  • a carboxylic acid is chosen as the salt-forming agent.
  • suitable carboxylic acids are aliphatic carboxylic acids, aliphatic dicarboxylic acids and aromatic carboxylic acids. Suitable choices are stearic acid, sebacic acid, cyclohexanedicarboxylic acid and benzenetricarboxylic acid.
  • the bridged amine compound having at least one N-bridgehead is not used as a salt if the salt-forming agent contains a halogen or sulphur, for it is generally known that halogen- containing or sulphur-containing compounds can reduce the effect of the HALS stabilizer.
  • the bridged amine compound having at least one N-bridgehead is preferably substituted with at least one substituent having a molecular weight of preferably at least 50, more preferably at least 100.
  • the plastics composition according to the invention preferably contains a thermoplastic polymer chosen from the group of polyolefins and styrene polymers. Suitable choices are, for example: - propylene polymers, such as propylene homopolymer, ethylene-propylene random copolymer, ethylene-propylene block copolymer and mixtures hereof. Also defined as propylene polymers within the scope of this invention are mixtures containing at least 50% by weight of one of the aforementioned propylene polymers with, for example, polyethylene or ethylene-propylene-diene copolymers ;
  • ethylene polymers such as low-density polyethylene (LDPE) , high-density polyethylene (HDPE) , very-low- density polyethylene (VLDPE) , linear-low-density polyethylene (LLDPE) or ultra-high-molecular-weight polyethylene (UHMWPE) ;
  • LDPE low-density polyethylene
  • HDPE high-density polyethylene
  • VLDPE very-low- density polyethylene
  • LLDPE linear-low-density polyethylene
  • UHMWPE ultra-high-molecular-weight polyethylene
  • styrene polymers such as poly (1-butylene) .
  • styrene polymers are, for example, polystyrene, high-impact-resistant polystyrene (HIPS) , styrene-acrylonitrile copolymer (SAN) , acrylonitrile- butadiene- styrene copolymer (ABS) , styrene-maleic anhydride copolymer (SMA) and styrene-maleimide copolymer (SMI) .
  • the polymer is a propylene polymer or an ABS, still more preferably a propylene polymer.
  • the bridged amine compound having at least one N-bridgehead can be introduced into the plastics composition with the aid of one of the many standard methods known to a person skilled in the art at any desired time before making a plastic article, for example a moulded part, sheet, film, fibre, coating, foam, tape, latex or powder, from the plastics composition.
  • the bridged amine compound having at least one N-bridgehead is mixed, for example in the form of a powder, solution, emulsion or suspension, with the other components of the plastics composition which are in the form of, for example, a powder or a melt.
  • the bridged amine compound having at least one N-bridgehead is first mixed with at least one HALS compound and optionally with other additives in a so-called additives package, for example in the form of a powder, solution, emulsion or suspension, and said package is then added to the plastic, for example in the form of a powder or as a melt.
  • the plastics composition containing a polymer, at least one HALS compound and at least one bridged amine compound having at least one N-bridgehead may also contain other additives, for example antioxidants, thermal and UV stabilizers, metal deactivators, fillers, pigments, flame retardants, optical whiteners and similar additives which are used in plastics compositions.
  • PP-MA-7-amino-l, 3 , 5 -triazadamantane 0.8 grams of 7 -amino-1, 3 , 5-triazadamantane in 75 ml of solvent was added, drop by drop, with constant stirring, at 160-165°C, to a solution of 10.0 grams of PP-MA (Hostaprime ,B HC5) (PP grafted with approximately 2.8% maleic anhydride) in 150 ml of inert solvent. After cooling to approx. 90°C, the product was precipitated using 100 ml of acetone. The separated product was dried in a vacuum drying stove, after which it was compressed to form a plate at 210°C. The latter was cryogenically ground to a powder.
  • a polymer powder (PP or ABS) was mixed with a solution containing an amount of a HALS compound. This mixture was dried in an oven (Hereaus Vacutherm) for 24 hours at a temperature of 28°C and a pressure of approximately 20 mm Hg . Then a solution of the bridged amine compound having at least one N-bridgehead was added to the plastics composition. This plastics composition was also dried in the same way as described above. Plastics compositions (blanks) in which the amount of HALS compound and/or bridged amine compound having at least one N-bridgehead in the solution was zero were also prepared using this process.
  • the PP composition was compressed to form a film using a Fontijne press (type TP200, 5 minutes pressureless preheating at 190°C, followed by the application of a pressure of 100 - 120 kNewton, followed by 10 minutes cooling at said pressure) .
  • the thickness was checked using a Heidenhain electronic meter. On average, thicknesses of 120 - 150 ⁇ m were obtained for the films and 1 mm for the plates.
  • the ABS composition was compressed to form a film using a Fontijne press (type TP200, 5 minutes preheating at a pressure of 50 kNewton and 210°C, followed by the application of a pressure of 100-120 kNewton, followed by 10 minutes cooling at said pressure) .
  • the thickness was checked using a Heidenhain electronic meter. On average, thicknesses of 120 - 150 ⁇ m were obtained for the films and 1 mm for the plates.
  • the PE compositions were produced by means of compounding at 160°C. Next, films with a thickness of 150 ⁇ m were blown at the same temperature. Determination of the weather resistance
  • the weather resistance of a plastics composition was determined in a weather-resistance test performed in an Atlas Material Testing Technology Weather-0 meter (type Ci65) according to the method described in the preceding description. The degradation was measured with the aid of FT-IR. The weather resistance is then expressed as the amount of time (the number of hours) for which a plastics composition is subjected to said combination of light, temperature and humidity and at which the difference between the measured carbonyl absorptions is less than 0.10 before and after ageing in the case of the films and less than 0.5 in the case of the plates. In some cases the change in colour as a result of ageing was characterized with the aid of a calorimeter according to ASTM standard 1925.
  • PE polyethylene
  • PP polypropylene
  • ABS acrylonitrile-butadiene- styrene copolymer
  • Tinuvin 770 * di- (2 , 2 , 6 , 6-tetramethyl-4 -piperidyl) sebacate
  • Tinuvin 'I 622 oligomer of N- (2 -hydroxyethyl) -2 , 2 , 6 , 6- tetramethyl-4-piperidinol and succinic acid
  • Tinuvin"' 123 bis- (l-octyloxy-2 , 2 , 6 , 6 -tetramethyl-4- piperidinyl) sebacate
  • Chimassorb 944 oligomer of cyanic acid and N,N- di (2 , 2 , 6 , 6-tetramethyl-4-piperidyl) -hexamethylene diamine
  • Hostavin N30 oligomer of 7-oxa-3 , 20-diazadispiro [5.1.11.2] -heneicosan-21-one, 2,2,4, 4- tetramethyl -20-
  • HMTA hexamethylenetetramine
  • DABCO stearate monosalt of stearic acid
  • DABCO DABCO distearate salt of DABCO containing two stearic acid molecules
  • DABCO sebacate salt of sebacic acid (diacid) containing two DABCO molecules
  • HMTA stearate monosalt of stearic acid and DABCO
  • Dodecylidene-atade 7-dodecylideneamino-l, 3,5- triazadamantane.
  • PP-MA-atade MA-grafted polypropylene modified with atade, synthesized according to the above specification.
  • a series of plastics compositions was prepared using the process described above. In this process, the composition of the plastics composition was varied. Di- (2 , 2 , 6 , 6-tetramethyl-4-piperidyl) sebacate (tradename: Tinuvin 770, Ciba-Geigy, Basel) was chosen as the HALS compound. PP (Stamylan " , type P83ml8, DSM, the Netherlands) was chosen as the polymer. Films were produced from the plastics compositions using the process described above. The films were subjected to a weather-resistance test and the weather resistance was determined as described above. The results are summarized in Table 1.
  • Examples III-VII and Comparative Experiments E and F Weather resistance of plastics compositions having various concentrations of HALS compound and bridged amine compound Example I was repeated, the concentrations of the HALS stabilizer chosen and the bridged amine compound having at least one N-bridgehead being varied. The results are summarized in Table 2. From this it can be concluded that a plastics composition containing amounts of 0.1% by weight to 0.5% by weight of a bridged amine compound exhibits improved weather resistance, which increases as more bridged amine compound is used. It was thus possible to more than double the weather resistance (Example F versus VII) .
  • Table 2 Weather resistance of plastics compositions having various concentrations of ⁇ HALS compound and bridged amine compound having at least one N-bridgehead
  • Example I was repeated using a plastics composition containing 0.2% of a HALS (Tinuvin 5 ' 770), the type of bridged amine compound having at least one N-bridgehead being varied.
  • HALS Tinuvin 5 ' 770
  • Example I was repeated using two plastics compositions, both composed of PE (LDPE, type 2304 ANOO, DSM, the Netherlands) and 0.05% by weight of HALS compound (Tinuvin" 770), with 0 and 0.06% by weight, respectively, of DABCO added thereto.
  • the plastics compositions were processed to form blown films 150 ⁇ m thick. The films were exposed to light in a Suntester.
  • the weather-resistance treatment was performed in a borosilicate glass vessel according to a method described in Polym. Peg. & Stab.. 39, 225-233 (1993) .
  • the weather resistance was determined as described above; however, in this case, a change in the carbonyl absorption of 0.05 units was employed as determining the weather resistance.
  • the weather resistance of the film without DABCO was 2700 hours and the degradation increased considerably from 2400 hours onwards; the weather resistance of the film containing DABCO was more than 3500 hours and the degradation showed a constant profile at 0.03 units.
  • a series of plastics compositions was prepared using the process described above. In this process the composition of the plastics composition was varied. Di- (2 , 2 , 6 , 6-tetramethyl-4-piperidyl) sebacate (tradename: Tinuvin * 770, Ciba-Geigy, Basel) was chosen as the HALS compound. ABS (Ronfalin", type 356**, DSM, the Netherlands) was chosen as the polymer. Plates were produced from the plastics compositions using the process described above.
  • the degradation was measured as a change in colour using a colorimeter and the weather resistance was determined according to ASTM standard 1925 as the amount of time (the number of hours) for which a plastics composition is subjected to said weather-resistance test and at which the measured change in colour is less than 5 units.
  • ASTM standard 1925 the amount of time (the number of hours) for which a plastics composition is subjected to said weather-resistance test and at which the measured change in colour is less than 5 units.
  • Table 6 Weather resistance of plastics compositions containing various types of bridged ⁇ CL. amine compounds having at least one N-bridgehead.
  • Table 7 Weather resistance of plastics compositions having various concentrations of HALS and 7-amino-l, 3 , 5-triazadamantane .
  • a series of plastics compositions was prepared using the process described above. In this process the composition of the plastics composition was varied. Di- (2 , 2 , 6 , 6 -tetramethyl- -piperidyl) sebacate (Tinuvin ® 770), oligomer of N- (2 -hydroxyethyl) -2 , 2 , 6 , 6- tetramethyl-4-piperidinol and succinic acid (Tinuvin ® 622), bis- (l-octyloxy-2,2, 6, 6-tetramethyl-4- piperidinyl) sebacate (Tinuvin ® 123) , oligomer of cyanic acid and N,N-di (2 , 2 , 6 , 6-tetramethyl-4-piperidyl) hexamethylene diamine (Chimassorb ® 944), 1,3,5- triazine-2 , 4, 6-triamine, N,N - [1, 2 -ethane- diylbis [ [ [4,
  • HMTA stearate, 7-dodecylideneamino- 1, 3 , 5 -triazadamantane and PP-MA-7-amino-l, 3 , 5- triazadamantane were chosen as the bridged amines .
  • PP Stamylan
  • Table 8 Weather resistance of plastics compositions containing various types of HALS
  • Table 9 Weather resistance of plastics compositions containing various types of bridged U 0. amines having at least one nitrogen as a bridgehead:
  • Table 10 Weather resistance of plastics compositions containing HMTA stearate
  • H U C various types of HALS:
  • Table 11 Weather resistance of plastics compositions containing dodecylidene-atade and various types of HALS:
  • Table 12 Weather resistance of plastics compositions containing PP-MA-atade and various ⁇ a. types of HALS:
  • H Table 13 Weather resistance of plastics compositions containing various amounts of HALS ⁇ a. (Tinuvin 770 or Chimassorb 944) :
  • Table 14 Weather resistance of plastics compositions containing various amounts of ⁇ bridged amines having at least one nitrogen as a bridgehead (HMTA stearate and dodecylidene-atade) :
  • Table 15 Weather resistance of plastics compositions containing various amounts of bridged amines having at least one nitrogen as a bridgehead (HMTA stearate and dodecylidene-atade) and with 0.05% HALS (Tinuvin 770):
  • H Table 16 Weather resistance of plastics compositions containing various amounts of ftU. bridged amines having at least one nitrogen as a bridgehead (HMTA stearate and dodecylidene-atade) and with 0.1% HALS (Tinuvin 770):
  • H Table 17 Weather resistance of plastics compositions containing various amounts of ftU. bridged amines having at least one nitrogen as a bridgehead (HMTA stearate and dodecylidene-atade) and with 0.2% HALS (Tinuvin 770):
  • Table 18 Weather resistance of plastics compositions containing various amounts of ft ⁇ . bridged amines having at least one nitrogen as a bridgehead (HMTA stearate and dodecylidene-atade) and with 0.05% HALS (Chimassorb 944):
  • H Table 19 Weather resistance of plastics compositions containing various amounts of Uft. bridged amines having at least one nitrogen as a bridgehead (HMTA stearate and dodecylidene-atade) and with 0.1% HALS (Chimassorb 944):
  • Table 20 Weather resistance of plastics compositions containing various amounts of ft. bridged amines having at least one nitrogen as a bridgehead (HMTA stearate and dodecylidene-atade) and with 0.2% HALS (Chimassorb 944):
  • a series of plastics compositions was prepared using the process described above. In this process the composition of the plastics composition was varied using various non-HALS stabilizers. 2-hydroxy-4- n-octoxy-benzophenone (Chimassorb 81), 2- (2 ' -hydroxy- 3 ' , 5 ' -di-tert-butyl-phenyl) -5-chloro-benzotriazol (Tinuvin 18 327) and octadecyl-3- (3 , 5-di-tert-butyl-4- hydroxy-phenyl) -propionate (Irganox 0 " 1076) were chosen as the non-HALS stabilizers.
  • DABCO stearate and HMTA stearate were chosen as the bridged amines having an N- bridgehead.
  • PP Stamylan R , type P83ml8, DSM, the Netherlands
  • Films were produced from the plastics compositions using the process described above. The films were subjected to a weather-resistance test and the weather resistance was determined as described above. The results are summarized in Table 21.
  • Table 21 Weather resistance of plastics compositions containing various non-HALS ⁇ ft. stabilizers and bridged amines having an N-bridgehead.

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Abstract

L'invention concerne une composition de matières plastiques renfermant un polymère, au moins un photostabilisant à amine entravée (composé HALS) et au moins un composé amine ponté présentant au moins une tête de pont N. De préférence, le composé amine ponté est l'hexaméthylènetétramine, le diazabicyclo[2. 2. 2]octane ou un dérivé de l'un de ces composés. De préférence, le polymère est un polymère propylène ou un copolymère acrylonitrile-butadiène styrène (ABS). La composition de matières plastiques de l'invention présente une résistance accrue aux intempéries.
PCT/NL1998/000088 1997-02-12 1998-02-12 Composition de matieres plastiques presentant une resistance accrue aux intemperies WO1998036023A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
BR9807679-5A BR9807679A (pt) 1997-02-12 1998-02-12 Composição plástica tendo resistência aperfeiçoada às intempéries
AU61231/98A AU6123198A (en) 1997-02-12 1998-02-12 Plastics composition having improved weather resistance
IL13132598A IL131325A0 (en) 1997-02-12 1998-02-12 Plastics composition having improved weather resistance
JP53561198A JP2001511834A (ja) 1997-02-12 1998-02-12 改善された耐候性を有するプラスチック組成物
CA002280158A CA2280158A1 (fr) 1997-02-12 1998-02-12 Composition de matieres plastiques presentant une resistance accrue aux intemperies
EP98905864A EP0960160A1 (fr) 1997-02-12 1998-02-12 Composition de matieres plastiques presentant une resistance accrue aux intemperies

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NL1005254 1997-02-12
NL1005254A NL1005254C2 (nl) 1997-02-12 1997-02-12 Kunststofsamenstelling met een verbeterde weersbestendigheid.

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WO1998036023A1 true WO1998036023A1 (fr) 1998-08-20

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JP (1) JP2001511834A (fr)
KR (1) KR20000071031A (fr)
CN (1) CN1252081A (fr)
AU (1) AU6123198A (fr)
BR (1) BR9807679A (fr)
CA (1) CA2280158A1 (fr)
IL (1) IL131325A0 (fr)
NL (1) NL1005254C2 (fr)
TR (1) TR199901924T2 (fr)
WO (1) WO1998036023A1 (fr)

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NL1009844C2 (nl) * 1998-08-12 2000-02-15 Dsm Nv Kunststofsamenstelling met een verbeterde weersbestendigheid.
JP2001288360A (ja) * 2000-04-04 2001-10-16 Unitika Ltd ポリアミド樹脂組成物及びその製造法
EP1571177A1 (fr) * 2004-03-03 2005-09-07 DSM IP Assets B.V. Elastomeres avec résistance aux intempéries ameliorée
WO2006002187A1 (fr) * 2004-06-22 2006-01-05 Invista Technologies S.A R.L. Composition d'additif solubilisee comprenant des constituants acides et basiques
WO2008033767A1 (fr) * 2006-09-15 2008-03-20 The Coca-Cola Company Outillage sous pression pour le moulage par injection et procédé d'utilisation correspondant

Families Citing this family (1)

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Publication number Priority date Publication date Assignee Title
CN110028784B (zh) * 2018-01-12 2022-03-08 天津利安隆新材料股份有限公司 用于尼龙的光稳定剂组合物

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL1009844C2 (nl) * 1998-08-12 2000-02-15 Dsm Nv Kunststofsamenstelling met een verbeterde weersbestendigheid.
WO2000009604A1 (fr) * 1998-08-12 2000-02-24 Dsm N.V. Composition de plastique a resistance aux intemperies accrue
JP2001288360A (ja) * 2000-04-04 2001-10-16 Unitika Ltd ポリアミド樹脂組成物及びその製造法
EP1571177A1 (fr) * 2004-03-03 2005-09-07 DSM IP Assets B.V. Elastomeres avec résistance aux intempéries ameliorée
WO2006002187A1 (fr) * 2004-06-22 2006-01-05 Invista Technologies S.A R.L. Composition d'additif solubilisee comprenant des constituants acides et basiques
WO2008033767A1 (fr) * 2006-09-15 2008-03-20 The Coca-Cola Company Outillage sous pression pour le moulage par injection et procédé d'utilisation correspondant
US7790077B2 (en) 2006-09-15 2010-09-07 The Coca-Cola Company Pressurized tooling for injection molding and method of using

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KR20000071031A (ko) 2000-11-25
CN1252081A (zh) 2000-05-03
CA2280158A1 (fr) 1998-08-20
BR9807679A (pt) 2000-02-15
NL1005254C2 (nl) 1998-08-13
TR199901924T2 (xx) 1999-12-21
AU6123198A (en) 1998-09-08
EP0960160A1 (fr) 1999-12-01
IL131325A0 (en) 2001-01-28
JP2001511834A (ja) 2001-08-14

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