NO304075B1 - Fremgangsmåte for reduksjon av misfarvingen av en plastformmasse, formmasse inneholdende en polymer av et mono-eller et diolefin samt anvendelse av ditrimetyolpropan for desaktivering av katalysatorrester i en organisk polymer - Google Patents
Fremgangsmåte for reduksjon av misfarvingen av en plastformmasse, formmasse inneholdende en polymer av et mono-eller et diolefin samt anvendelse av ditrimetyolpropan for desaktivering av katalysatorrester i en organisk polymer Download PDFInfo
- Publication number
- NO304075B1 NO304075B1 NO914461A NO914461A NO304075B1 NO 304075 B1 NO304075 B1 NO 304075B1 NO 914461 A NO914461 A NO 914461A NO 914461 A NO914461 A NO 914461A NO 304075 B1 NO304075 B1 NO 304075B1
- Authority
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- Norway
- Prior art keywords
- polymer
- butyl
- mono
- diolefin
- bis
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- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
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- IXHMTDIIQNIVBN-UHFFFAOYSA-N n'-(2,2-dihydroxyethyl)oxamide Chemical compound NC(=O)C(=O)NCC(O)O IXHMTDIIQNIVBN-UHFFFAOYSA-N 0.000 description 2
- UKJARPDLRWBRAX-UHFFFAOYSA-N n,n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine Chemical compound C1C(C)(C)NC(C)(C)CC1NCCCCCCNC1CC(C)(C)NC(C)(C)C1 UKJARPDLRWBRAX-UHFFFAOYSA-N 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
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- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F6/00—Post-polymerisation treatments
- C08F6/02—Neutralisation of the polymerisation mass, e.g. killing the catalyst also removal of catalyst residues
-
- 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
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
Description
Foreliggende oppfinnelse angår anvendelsen av og ditrimetylolpropan for å redusere misfarving av plastformmasser som inneholder fenoliske stabilisatorer og metallioner som katalysatorrester og som bearbeides ved høyere temperaturer.
Oppfinnelsen angår også en plastform-masse inneholdende en polymer av et mono- eller et diolefin, en kopolymer av et mono- eller diolefin med en annen vinylmonomer, en polyester eller et polykarbonat, en fenolisk forbindelse som stabilisator og tungmetall ioner som katalysatorrester.
Oppfinnelsen angår til slutt anvendelse av de trimetylol-propan for desaktivering av katalysatorrester.
Ved fremstilling av en rekke polymerer blir det for polymeri-seringen anvendt metallholdige katalysatorer, spesielt slike på basis av overgangsmetaller. Da restene av disse katalysatorer blant annet virker som katalysatorer for den termisk oksydative eller lysinduserte nedbrytning av polymerene, må andel i polymerene allerede av denne grunn holdes så lav som mulig. Videre kan restene av disse katalysatorene danne farvede komplekser som fenoliske antioksydanter som tilsettes til polymerene, noe som kan føre til uønsket misfarving i polymerene. I tillegg kan virkningen av antioksydantene og lysbeskyttelsesmidlene påvirkes.
Det er kjent at polyolefiner kan beskyttes med misfarving av den nevnte type hvis det tilsettes et ikke-ionisk overflate-aktivt stoff som for eksempel en polyglykol, polyalkohol eller et kondensasjonsprodukt av alkoholer med etylenoksyd, se GB 961480. Det har imidlertid vist seg at de nevnte forbindelser ikke alltid er virkningsfulle nok.
Videre er det kjent stabiliserte polyolefiner som inneholder polypentaerytritt, spesielt dipentaerytritt eller tripentaerytritt, se US-PS 3 337 495. Det vises i sammenlignings-forsøk at begge de to ovenfor nevnte polypentaerytritter har en bedre virkning enn polyglykoler eller polyalkoholer. Allikevel er virkningen ennu ikke tilfredsstillende.
Det forelå derfor en oppgave å finne forbindelser som ennu mer virksom måte med de kjente forbindelser kan redusere misfarvingen av plastformmasser.
Det er funnet at ditrimetylolpropan fyller denne oppgave.
I henhold til dette angår foreliggende oppfinnelse en fremgangsmåte for reduksjon av misfarvingen av en plast-formmasse inneholdende en polymer av et mono- eller diolefin, en kopolymer av et mono- eller diolefin med en annen vinylmonomer, en polyester eller et polykarbonat og en fenolisk forbindelse som stabilisator og tungmetall ioner som katalysatorrester, ved bearbeidingstemperaturen ved tilsetning av en polyhydroksyforbindelse, og denne fremgangsmåte karakteriseres ved at det til formmassen settes 0,001 til 1 vekt-#, beregnet på polymeren, av ditrimetylolpropan.
Oppfinnelsen angår som nevnt innledningsvis også en plastform-masse inneholdende en polymer av et mono- eller et diolefin, en kopolymer av et mono- eller diolefin med en annen vinylmonomer, en polyester eller et polykarbonat, en fenolisk forbindelse som stabilisator og tungmetall ioner som katalysatorrester, og denne masse karakteriseres ved et innhold på 0,001 til 1 vekt-#, beregnet på polymeren, av ditrimetylolpropan.
Til slutt angår oppfinnelsen anvendelsen av de trimetylol-propan for desaktivering av katalysator-rester i en organisk polymer som er en polymer av mono- eller diolefin eller en kopolymer av et mono- eller diolefin med en annen vinylmonomer, en polyester eller et polykarbonat.
Oppfinnelsens fremgangsmåte kan anvendes på formmasser som baserer seg på de nedenfor oppførte polymerer:
1. Polymerer av mono- og diolefiner, for eksempel polyetylen med høyere, midlere eller lavere densitet (som eventuelt kan være fornettet), polypropylen, polyisobutylen, polybuten—1, polymetylpenten—1, polyisopren eller polybutadien samt polymerisater av cykloolefiner som for eksempel cyklopenten eller norbornen. 2. Blandinger av de under 1) nevnte polymerer, for eksempel blandinger av polypropylen med polyetylen eller med polyisobutylen. 3. Kopolymerer av mono- og diolefiner seg imellom eller med andre vinylmonomerer som for eksempel etylen-propylen-kopolymerer, propylen-buten-l-kopolymerer, propylen-Isobutylen-kopolymerer, etylen-buten—1-kopolymerer, propylen-butadien-kopolymerer, isobutylen-isopren-kopolymerer, etylen-alkylakrylat-kopolymerer, etylen-alkylmetakrylat-kopolymerer, etylen-vinylacetat-kopolymerer eller etylen-akrylsyre-kopolymerer eller salter derav (ionomerer), samt terpolymerer av etylen med propylen og et dien som heksadien, dicyklopentadien eller etylidennorbornen. 4. Blandinger av kopolymerer ifølge punkt 3) med polymerer ifølge punktene 1) eller 2). 5. Polyestere som avledes fra dikarboksylsyrer og dioler og/eller fra hydroksykarboksylsyrer eller de tilsvarende laktoner som for eksempel polyetylentereftalat, poly-butylenteref talat, poly-1,4-dimetylolcykloheksan-tereftalat, poly-(2,2-bis(4-hydroksyfenyl)-propan)-tereftalat, polyhydroksybenzoat samt blokk-polyeterestere som avledes fra polyetere med hydroksyendegrupper, dialkoholer og i karboksylsyrer.
6. Polykarbonater.
Foretrukne polymerer er polyetylen og polypropylen.
De for oppfinnelsens fremgangsmåte anvendte katalysatordesaktivator er ditrimetylolpropan.
Ditrimetylolpropan er et stoff som i det vesentlige består av forbindelsen med formelen
Dette er et hvitt krystallinsk produkt med et smeltepunkt på ca. 109° C, et kokepunkt ved ca. 5 mbar på ca. 215° C og en densitet på 1,18 g/cm3 . Produktet er oppløselig i vann og alkoholer.
Katalysatordesaktivatoren ditrimetylolpropan settes til polymeren i en mengde på ca. 0,001 til 1 vekt-#, beregnet på polymeren. Derved er den tilsatte mengde avhengig av mengden av metallisk katalysatorrest som fremdeles befinner seg i polymeren.
Katalysatordesaktivatoren innarbeides generelt i henhold til vanlige metoder i de organiske polymerer. En innarbeidelse kan for eksempel skje ved innblanding eller påføring av forbindelsen og eventuelt ytterligere additiver i eller på polymeren umiddelbart efter polymerisering eller i smeiten før eller under formgivningen. Videre kan tilsetningen skje ved påføring av den oppløste eller dispergerte forbindelse direkte på polymeren eller innblanding i en oppløsning, suspensjon eller emulsjon av polymeren, eventuelt under efterfølgende fordamping av oppløsningsmidlet. Forbindelsene er også virksomme når de innarbeides efterpå i en allerede granulert polymer i et spesielt bearbeidingstrinn. Forbindelsen som anvendes ifølge oppfinnelsen kan også tilsettes i form av en mastersats som inneholder disse forbindelser for eksempel i en konsentrasjon på 1 til 75, og fortrinnsvis 2,5 til 30 vekt-#, som så settes til polymerene som skal stabiliseres.
I tillegg kan de organiske polymerer som skal stabiliseres også inneholde følgende antioksydanter: 1. Alkylerte monofenoler, for eksempel
2,6-di-t-butyl-4-metylfenol,
2-t-butyl-4,6-dimetylfenol,
2,6-di-t-butyl-4-etylfenol,
2,6-di-t-butyl-4-n-butylfenol,
2,6-di-t-butyl-4-i-butylfenol,
2 ,6-di-cyklopentyl-4-metylfenol, 2-(cx-metylcykloheksyl )-4 ,6-dimetylf enol, 2,6-di-oktadecyl-4-metylfenol, 2 ,4 ,6-tri-cykloheksylfenol,
2 ,6-di-t-butyl-4-metoksymetylfenol.
2. Alkylerte hydrokinoner, for eksempel
2,6-di-t-butyl-4-metoksyfenol,
2,5-di-t-butyl-hydrokinon,
2.5- di-t-amyl-hydrokinon,
2.6- difenyl-4-oktadecyloksyfenol.
3. Hydroksylerte tiodifenyletere, for eksempel 2,2'-tio-bis-(6-t-butyl-4-metylfenol), 2 ,2 '-tio-bis-(4-oktylfenol), 4 ,4 '-tio-bis-(6-t-butyl-3-metylfenol),
4 ,4 '-tio-bis-(6-t-butyl-2-metylfenol).
4. Alkyliden-bisfenoler, for eksempel
2,2'-metylen-bis-(6-t-butyl-4-metylfenol), 2,2' -metylen-bis-(6-z-b"utyl-4-etylfenol),
2,2'-metylen-bis-[4-metyl-6-(a-metylcykloheksyl)-fenol], 2,2'-metylen-bis-(4-metyl-6-cykloheksylfenol), 2,2'-metylen-bis-(6-nonyl-4-metylfenol), 2,2'-metylen-bis-(4,6-di-t-butylfenol), 2,2'-etyliden-bis-(4,6-di-t-butylfenol), 2,2'-etyliden-bis(6-t-butyl-4-isobutylfenol), 2,2'-metylen-bis-[6-(a-metylbenzyl)-4-nonylfenol] , 2,2'-metylen-bis-[6-(a,a-dimetylbenzyl)-4-nonylfenol], 4,4'-metylen-bis-(2,6-di-t-butylfenol), 4,4'-metylen-bis-(6-t-butyl-2-metylfenol), 1,l-bis-(5-t-butyl-4-hydroksy-2-metylfenyl)-butan, 2,6-di-(3-t-butyl-5-metyl-2-hydroksybenzyl)-4-metylfenol, 1,1,3-tris-(5-t-butyl-4-hydroksy-2-metylfenyl)-butan, 1 , l-bis-( 5-t-butyl-4-hydroksy-2-metylfenyl )-3-n-dodecyl-merkaptobutan, di-( 3-t-butyl-4-hydroksy-5-metylfenyl)-dicyklopentadien,
di - [2 - ( 3-t-butyl-2 ' -hydroksy-5 '-metylbenzyl )-6-t-butyl-4-metylfenyl]-tereftalat, etylenglykol-bis[3 , 3-bis-( 3 ' -t-butyl-4 '-hydroksyfenyl )-butyrat, 5. Benzylforbindelser, for eksempel
1,3,5-tri-(3,5-di-t-butyl-4-hydroksybenzyl)-2,4,6-trimetylbenzen, di-(3,5-di-t-butyl-4-hydroksybenzyl)-sulf id, 3 , 5 -d i-1-butyl-4-hydroksybenzyl-merkaptoeddiksyreiso-oktylester,
bis-(4-t-butyl-3-hydroksy-2,6-dimetylbenzyl)-ditiol-tereftalat, l,3,5-tris-(3 , 5-di-t-butyl-4-hydroksybenzyl)-isocyanurat, 1,3,5-tris-(4-t-butyl-3-hydroksy-2,6-dimetylbenzyl)-i socyanurat, 3 , 5 - di - t-butyl -4 -hydroksybenzy 1 - f os f onsyre-dioktacecyl-ester ,
kalsiumsalt av 3,5-di-t-butyl-4-hydroksybenzyl-fosfonsyre-mono-etylestere. 6. Acylaminofenoler, for eksempel
4-hydroksy-laurinsyreanilid,
4-hydroksy-starinsyreanilid, 2 , 4-bis-oktylmerkapto-6-( 3 , 5-di -t- butyl-4-hydroksy-anilino )-s-triazin,
N-( 3 ,5-di-t-butyl-4-hydroksyfenyl )-karbanrinsyre-oktyl-ester. 7. Estere av p<->(3,5-di-t-butyl-4-hydroksyfenyl)-propionsyre med en- eller flerverdige alkoholer, for eksempel med metanol, dietylenglykol,
oktadecanol, trietylenglykol,
1,6-heksandiol, pentaerytritol,
neopentylglykol, tris-hydroksyetyl-isocyanurat, tiodietylenglykol, di-hydroksyetyl-oksalsyrediamid. 8. Estere av p-(5-t-butyl-4-hydroksy-3-metylfenyl)-propion-syre med en- eller flerverdige alkoholer, for eksempel med metanol, dietylenglykol,
oktadecanol, trietylenglykol,
1,6-heksandiol, pentaerytritt,
neopentylglykol, tris-hydroksyetyl-isocyanurat, tiodietylenglykol, di-hydroksyetyl-oksalsyrediamid.
9. Amider av p<->(3,5-di-t-butyl-4-hydroksyfenyl)-propionsyre, som for eksempel
N ,N ' - di-( 3 , 5-di-t-butyl-4-hydroksyf enylpropionyl )heksa-metylendiamin,
N ,N-di-(3,5-di-t-butyl-4-hydroksyfenylpropionyl) - trimetylendiamin,
N,N'-di-(3,5-di-t-butyl-4-hydroksyfenylpropionyl)-hydrazin.
I tillegg kan polymerene som skal stabiliseres også inneholde ytterligere additiver som for eksempel:
1. UV-adsorbere og lysbeskyttelsesmidler.
1.1 2-(2'-hydroksyfenyl )-benztriazoler , som for eksempel 5'-metyl-, 3',5'-di-t-butyl-, 5'-t-butyl-, 5'-(1,1,3,3-tetrametylbutyl)-, 5-klor-3',5'-di-t-butyl, 5-klor-3'-t-butyl-5'-metyl, 3'-sek-butyl-5'-t-butyl, 4'-oktoksy-, 3',5'-di-t-amyl-, 3',5'-bis(a,a-dimetylbenzyl)-derivatet.
1.2 2-hydroksybenzofenoner, for eksempel
4-hydroksy-, 4—metoksy, 4-oktoksy, 4-decyloksy-, 4—dodecyloksy-, 4—benzyloksy-, 4,2',4'-trihydroksy-, 2'-hydroksy-4,4'-dimetoksy-derivatet.
1.3 Estere av eventuelt substituerte benzosyrer, for eksempel
4-t-butyl-fenylsalicylat, fenylsalicylat, oktylfenyl-salicylat, dibenzoylresorcin, bis-(4-t-butylbenzoyl)-resorcin, benzoylresorcin, 3,5-di-t-butyl-4-hydroksy-benzosyre-2 ,4-di-t-butylfenylester, 3,5-di-t-butyl-4-hydroksybenzosyreheksadecylester.
1.4 Akrylater, for eksempel
a-cyan-P,<p->difenylakrylsyre-etylester henholdsvis —isooktylester, a-karbometoksykanelsyremetylester, a—cyano-p<->metyl-p-metoksy-kanelsyremetylester henholdsvis —butylester, a-karbometoksy-p-metoksy-kanelsyremetylester, N-(p<->karbometoksy-9-cyano-vinyl )-2-metyl-indolin.
1.5 Nikkelforbindelser, for eksempel
Nikkelkomplekser av 2,2-tio-bis[4-(1,1,3,3-tetra-metyl- butyl )-fenol] som 1:1- eller 1:2-komplekset, eventuelt med ytterligere ligander som n-butylamin, trietanolamin eller N-cykloheksyl-dietanolamin, nikkelalkylditiokarbamater, nikkelsalter av 4—hydroksy-3,5-di-t-butyl-benzylfosfonsyre-mono- alkylestere som av metyl- eller etylester, nikkelkomplekser av ketoksimer som av 2-hydroksy-4-metyl-fenylundecylketoksim, nikkelkomplekser av l-fenyl-4-lauroyl-5-hydroksy-pyrazoler, eventuelt med ytterligere ligander, nikkelsalter av 2-hydroksy-4-alkoksybenzofenoner.
1.6 Sterisk hindrede aminer, for eksempel
1.6.1. bis-(2,2,6,6-tetrametylpiperidyl)-sebacat,
bis-(l,2,2,6,6-pentametylpiperidyl)-sebacat, bis-(2,2,6,6,-tetrametylpiperidyl)-glutarat, bis-(l,2,2,6 ,6-pentametylpiperidyl)-glutarat, bis-(2,2,6,6-tetrametylpiperidyl)-succinat, bis-(l,2,2,6,6-pentametylpiperidyl)-succinat, 4-stearyloksy-2,2,6,6-tetrametylpiperidin, 4-stearyloksy-l,2,6,6-pentametylpiperidin, 4-stearoyloksy-2,2,6,6-tetrametylpiperidin, 4-stearoyloksy-l,2,2,6,6-pentametylpiperidin, 2,2,6,6-tetrametylpiperidylbehenat, 1,2,2,6,6-tetrametyl-7-oksa-3,20-diazadispiro-[5,1,11,2]-heneicosan-21-on,
2 ,2 ,3 ,4 ,4-penta-metyl-7-oksa-3,20-diazadispiro-[5,1,11,2]-heneicosan-21-on, 2,2,4,4-tetrametyl-3-acetyl-7-oksa-3,20-diazadispiro-[5,1,11,2]-heneicosan-21-on, 2,2,4 , 4-tetrametyl-7-oksa-3 , 2 0-diaza-20-(p-lauryl-oksykarbonyletyl )-21-oksodispiro-[5 ,1 ,11 ,2] -heneicosan, 2,2,3,4 , 4-pentametyl-7-oksa-3,20-diaza-20-(e-lauryl-oksykarbonyletyl )-21-okso-dispiro-[5,1,11,2]-heneicosan, 2,2,4 , 4-tetrametyl-3-acetyl-7-oksa-3 , 20-diaza-20-((3-lauryloksykarbonyletyl )-21-okso-dispiro-[5 ,1,11,2]-heneicosan, 1,1' ,3,3' ,5,5'-heksahydro-2,2',4 , 4 ' , 6 ,6'-heksaaza- 2 , 2 ' , 6 , 6 ' -bismetano-7 ,8-diokso-4 ,4'-bis-(l,2,2,6,6-pentametyl-4-piperidyl)bifenyl, NN ' N ' 'N ' ' '-tetrakis-[2,4-bis-[N-(2,2,6,6-tetrametyl-4-piperidyl)-butylamino]-l,3,5-triazin-6-yl]-4,7-dlazadecan-1,10-diamin, NN'N''N'<»>'-tetrakis-[2,4-bis-[N-(l,2,2,6,6-penta-metyl-4-piperidyl ) -butyl amino] -1,3 ,5-triazin-6-yl]-4 ,7-diazadecan-l,10-diamin, NN'N' 'N' ' '-tetrakis-[2 ,4-bis-[-(2 ,2 ,6 , å-tetrametyl^-piperidyl )-metoksypropylamin] -1,3, 5 -triazin-6-yl]-4 ,7-diazadecan-l,10-diamin, NN'N''N'''-tetrakis-[2,4-bis-[-(l,2,2,6,6-pentametyl-4-piperidyl)-metoksypropylamino]-1,3,5-triazin-6-yl]-4 ,7-diazadecan-l,10-diamin, bis-(l,2,2,6,6-pentametyl-piperidyl)-n-butyl-3,5-di-t-butyl -4 -hydroksy-benzylmalonat , tris-(2,2,6,6-tetrametyl-4-piperidyl)-nitrilotri-acetat, tetrakis-(2,2,6,6-tetråmetyl-4-piper idyl)-l,2 ,3 ,4-butantetrakarboksylsyre, 1 , 1 ' - ( 1 ,2-etandiyl )-b i s-(3 , 3,5,5 -1etr ame ty1-piperazinon), 1.6.2. Poly-N,N'-bis-(2,2,6 , 6-tet rame ty 1-4-piper idyl )-l ,8-diazadecylen, kondensasjonsprodukter av 1 - ( 2-hydroksyetyl)-2,2,6,6-tetrametyl-4-hydroksy-piperidin og ravsyre,
kondensasjonsproduktet av N,N'-bis-(2,2,6,6-tetra-metyl-4-piperidyl)-heksametylendiamin og 4-t-oktylamino-2,6-diklor-l,3,5-triazin, kondensasjonsproduktet av N,N'-bis-(2,2,6,6-tetra-metyl-4-piperidyl)-heksametylendiamin og 4-morfolino-2 ,6-diklor-l,3,5-triazin. 1.7 Oksalsyrediamider, for eksempel 4 ,4 '-di-oktyloksy-oksanilid, 2,2'-di-oktyloksy-5,5'-di-t-butyl-oksanilid, 2,2'-didodecyloksy-5,5'-di-t- butyloksanilid, 2-etoksy-2'-etyl-oksanilid, N,N'-bis-(3-dimetylaminopropyl)oksalamid, 2-etoksy-5-t-butyl-2'-etyloksanilid og dennes blanding med 2-etoksy-2'-etyl-5,4-di-t-butyl-oksanilid, blandinger av o- og p—metoksy- samt av o- og p-etoksy-di-substituerte oksanilider. 2. Metalldesaktivatorer, for eksempel N ,N'-difenyloksalsyrediamid, N-salicylal-N'-sali-cyloyl-hydrazin , N,N'-bis-salicyloyl-hydrazin, N,H'-bis-(3,5-di-t-butyl-4-hydroksyfenylpropionyl )-hydrazin, 3-salicyloylamino-1,2,3-triazol, bis-benzyliden-oksalsyredihydrazid. 3. Fosfitter og fosfonitter, for eksempel trifenylfosfitt, difenylalkylfosfitt, fenyldialkyl-fosfitt, trisnonylfenylfosfitt, trilaurylfosfitt, trioktadecylfosf itt, distearylpentaerytrityl-difosfitt, tris-(2,4-di-t-butylfenyl)fosfitt, diisodecyl-pentaerytrityl-difosfitt, bis-(2,4-di-t-butylf enyl)-pentaerytrityl-difosf itt, tristearyl-sorbityltrifosfitt, tetrakis-(2,4-di-t-butylfenyl)-4,4-bifenylen-difosfonitt, 3,9-bis-(2,4-di-t-butylf enoksy)-2, 4 ,8,10-tetraoksa-3 , 9-disfosfaspiro-(5,5 )-undecan, tris-(2-t-butyl-4-tio-(2 *-meteny1-4'-hydroksy-5'-t-butyl)-fenyl-5-metenyl )-fenylfosfitt, 4. Peroksydødeleggende forbindelser, for eksempel estere av p-tio-dipropionsyre, som for eksempel lauryl-, stearyl-, myristyl- eller tridecylester, merkaptobenzimidazol, sinksaltet av 2-merkaptobenzimidazol, sink-alkyl-ditiokarbamat, dioktadecyl-sulfid, dioktadecyldisulfid, penerytritt-tetrakis-(p<->dodecylmerkapto)-propionat. 5. Basiske ko-stabilisatorer, for eksempel melamin, polyvinylpyrrolidon, dicyandiamid, triallyl-cyanurat, urinstoff-derivater, hydrazin-derivater, amin, polyamin, polyuretan, alkali- og jordalkali-metallsalter av høyere fettsyrer eller fenolater, for eksempel Ca-stearat, Zn-stearat, Mg-stearat, Na-ricinoleat, K-palmitat, antimonbrenzkatekinat eller tinnbrenzkatekinat, hydroksyder og oksyder av jordalkalimetaller eller aluminium, for eksempel CaO, MgO, ZnO. 6. Kjernedannelsesmidler, for eksempel
4-t-butylbenzosyre, adipinsyre, difenyleddiksyre, dibenzylidensorbitol. 7. Fyllstoffer for forsterkningsmidler, for eksempel kalsiumkarbonat, silikater, glassfibre, asbest, talkum, kaolin, glimmer, bariumsulfat, metalloksyder og —hydroksyder, sot, grafitt. 8. Ytterligere tilsetninger, for eksempel myknere, smøremidler, emulgatorer, pigmenter, optiske lysgjørere, flammebeskyttelsesmidler, antistatika eller drivmidler.
De forskjellige ytterligere additiver fra de ovenfor nevnte grupper 1 til 6 settes til polymerene som skal stabiliseres i en mengde på 0,01 til 10, fortrinnsvis 0,01 til 5 vekt-#, beregnet på den totale vekt av formmassen. Mengdeandelen av additivene fra gruppene 7 og 8 er 1 til 80, og fortrinnsvis 10 til 50 vekt-#, beregnet på den totale formmasse.
Oppfinnelsens stabiliserte organiske polymerer kan anvendes i forskjellige former, for eksempel som folier, fibre, bånd, profiler, som belegningsmasser eller som bindemidler for lakker, adhesiver eller kitt.
Derved har ditrimetylolpropan ("di-TMP") ved siden av sin utmerkede virkning som katalysatordesaktivator også fordelen av en så å si optimal påsmeltingsoppførsel med et smeltepunkt på 108 til 111°C. Denne fysikalske egenskap muliggjør en optimal "behandling" av di-TMP, både ved lagring, doseringen eller ved blandingen med polymeren i hvilken den skal innføres. Smeltepunktet er for det første så høyt at det ikke oppstår problemer som sammenklumping eller lignende ved lagring, og di-TMP kan optimalt doseres til polymeren i form av et pulver og blandes med denne (den nøyaktige dosering og den homogene innblanding av viskøse væsker som for eksempel glycerol eller polyetylenglykol 400 gir betydelige vanskelig-heter ).
For det andre er smeltepunktet på 108 til 111°C imidlertid så lavt at det sikres en homogen fordeling i den smeltede polymer (ved forarbeidingen) (den homogene fordeling av for eksempel tripentaerytritt med et smeltepunkt på 245<0>C i polyetylen er ikke garantert ved en bearbeidingstemperatur på ca. 200°C).
De efterfølgende eksempler skal forklare oppfinnelsen nærmere.
Eksempel 1
500 g polypropylen (densitet ved 20°C ca. 0,88 g/cm<3>, smeltepunkt ca. 158°C, viskositet ved 170"C ca. 1500 mPa.s) ble smeltet ved 160°C og derefter blandet med 2,5 g (2,13 mmol) pentaerytrityl-tetrakis-[3-(3,5-di-t-butyl-4-hydroksyfenyl)-propionat] (antioksydant 1) (fenolisk antioksydant) og omrørt i 15 minutter ved 160°C. Derefter ble det tilsatt 2,5 cm<5>(0,5 mmol) trietylaluminium (oppløsning i Esso-varsol) og blandingen omrørt ytterligere i 15 minutter ved 160°C. Ved
tilsetning av trietylaluminium ble nærvær av metalliske katalysatorrester simulert (aluminiumforbindelser er en bestanddel av Ziegler-Natta-polymeriseringskatalysatorer ).
Man oppnådde et intenst rødfiolett farvet polypropylen. Fra dette rødfiolettfarvede polypropylen ble porsjoner på 100 g ( inneholdende 1,0 mmol Et3Al) oppvarmet til 200°C under Ng-atmosfaere og av katalysatordesaktivatoren som skulle under-søkes ble det porsjonsvis tilsatt så mye at det ikke engang efter lengre tids omrøring ved 200°C ga noen farveendring i polypropylenet. I tabell 1 oppsummeres "sluttfarven" for polypropylen og den for oppnåelse av denne "sluttfarve" tilsatte mengde av den undersøkte forbindelse.
Eksempel 2
Man gjentok eksempel 1, men benyttet som fenolisk antioksydant 2,5 g (3,14 mmol) bis-[3,3-bis-(4'-hydroksy-3'-t-butylfenyl)-butansyre]-glykolester (antioksydant 2). Man oppnådde et fiolett polypropylen.
Eksempel 3
Man gjentok eksempel 1, men i stedet for 2,5 cm<3>trietyl-aluminiumoppløsning tilsatte man 0,6 cm<3>(5,47 mmol) titan(IV)klorid (titanforbindelser inneholdes i Ziegler-Natta-katalysatorer). Man oppnådde med dette (sammen med den fenoliske antioksydant) et rødbrunt polypropylen.
Eksempel 4
Man gjentok eksempel 3, men benyttet som fenolisk antioksydant 2,5 g (3,14 mmol) bis-[3,3-bis-(4'-hydroksy-3 '-t-butylfenyl)-butansyre]-glykolester. Man oppnådde et rødbrunt polypropylen.
Eksempel 5
Til 100 deler polyetylen (densitet ved 23°C 0,955 g/cm3 ; MFI 0/5 0,28 g/10 min.; MF I 190/21,6 9 g/10 min. ustabil) ble det satt 0,1 del kalsiumstearat og x deler additiv.
Blandingene ble knadd i 10 minutter i en åpen målekna-apparatur ved 200°C og 20 omdr./min. Av dette prøvematerialet fremstilte man derefter en 1 mm pressplate ved 180° C og på denne ble gulhetsindeksen målt.
Eksempel 6
Man gjentok eksempel 5, men her ble virkningen i forskjellige polymerer undersøkt.
Eksempel 7
Avfarving av forskjellige fenoliske antioksydanter.
100 deler polyetylen som i eksempel 5 ble blandet med 0,1 deler kalsiumstearat og x deler additiv og granulert flere ganger (måleekstruder T = 200/250/3000C) . Efter hver granulering ble gulhetsindeksen målt på granulatet.
Claims (4)
1.
Fremgangsmåte for reduksjon av misfarvingen av en plast-formmasse inneholdende en polymer av et mono- eller diolefin, en kopolymer av et mono- eller diolefin med en annen vinylmonomer, en polyester eller et polykarbonat og en fenolisk forbindelse som stabilisator og tungmetall ioner som katalysatorrester, ved bearbeidingstemperaturen ved tilsetning av en polyhydroksyforbindelse,karakterisert vedat det til formmassen settes 0,001 til 1 vekt-#, beregnet på polymeren, av ditrimetylolpropan.
2.
Plastform-masse inneholdende en polymer av et mono- eller et diolefin, en kopolymer av et mono- eller diolefin med en annen vinylmonomer, en polyester eller et polykarbonat, en fenolisk forbindelse som stabilisator og tungmetall ioner som katalysatorrester,karakterisert vedet innhold på 0,001 til 1 vekt-#, beregnet på polymeren, av ditrimetylolpropan.
3.
Masse ifølge krav 2,karakterisert vedat polymeren er en polymer av et mono- eller diolefin eller en kopolymer av et mono- eller diolefin med en annen vinylmonomer .
4.
Anvendelse av ditrimetylolpropan for desaktivering av katalysator-rester i en organisk polymer som er en polymer av mono- eller diolefin eller en kopolymer av et mono- eller diolefin med en annen vinylmonomer, en polyester eller et polykarbonat.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4036359A DE4036359A1 (de) | 1990-11-15 | 1990-11-15 | Verfahren zur verminderung der verfaerbung einer kunststoff-formmasse bei der verarbeitungstemperatur |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO914461D0 NO914461D0 (no) | 1991-11-14 |
| NO914461L NO914461L (no) | 1992-05-18 |
| NO304075B1 true NO304075B1 (no) | 1998-10-19 |
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ID=6418293
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO914461A NO304075B1 (no) | 1990-11-15 | 1991-11-14 | Fremgangsmåte for reduksjon av misfarvingen av en plastformmasse, formmasse inneholdende en polymer av et mono-eller et diolefin samt anvendelse av ditrimetyolpropan for desaktivering av katalysatorrester i en organisk polymer |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US5331034A (no) |
| EP (1) | EP0485891B1 (no) |
| JP (1) | JPH04268349A (no) |
| KR (1) | KR920009929A (no) |
| AT (1) | ATE152469T1 (no) |
| AU (1) | AU640061B2 (no) |
| BR (1) | BR9104964A (no) |
| CA (1) | CA2055528A1 (no) |
| CS (1) | CS345691A3 (no) |
| DE (2) | DE4036359A1 (no) |
| DK (1) | DK0485891T3 (no) |
| ES (1) | ES2103765T3 (no) |
| FI (1) | FI915352A (no) |
| HU (1) | HU209722B (no) |
| IE (1) | IE913973A1 (no) |
| MX (1) | MX9102052A (no) |
| MY (1) | MY109712A (no) |
| NO (1) | NO304075B1 (no) |
| TW (1) | TW203068B (no) |
| ZA (1) | ZA919019B (no) |
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| US5852086A (en) * | 1996-09-30 | 1998-12-22 | The Goodyear Tire & Rubber Company | Polyamide-acrylonitrile butadiene blends with reduced gel and antigel agent |
| US5886073A (en) * | 1997-11-03 | 1999-03-23 | General Electric Company | Polycarbonate redistribution method with catalyst decomposition |
| US7781562B2 (en) | 2005-06-17 | 2010-08-24 | Eastman Chemical Company | Polyester compositions containing cyclobutanediol having a certain combination of inherent viscosity and moderate glass transition temperature and articles made therefrom |
| US20100184940A1 (en) * | 2005-03-02 | 2010-07-22 | Eastman Chemical Company | Polyester Compositions Which Comprise Cyclobutanediol and Certain Thermal Stabilizers, and/or Reaction Products Thereof |
| US7704605B2 (en) | 2006-03-28 | 2010-04-27 | Eastman Chemical Company | Thermoplastic articles comprising cyclobutanediol having a decorative material embedded therein |
| US8586701B2 (en) | 2005-10-28 | 2013-11-19 | Eastman Chemical Company | Process for the preparation of copolyesters based on 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 1,4-cyclohexanedimethanol |
| KR101410145B1 (ko) * | 2005-10-28 | 2014-06-19 | 이스트만 케미칼 컴파니 | 고유 점도와 적절한 유리전이온도의 특정 조합을 갖는사이클로뷰테인다이올을 포함하는 폴리에스터 조성물, 및이로부터 제조된 제품 |
| US20070106054A1 (en) * | 2005-10-28 | 2007-05-10 | Crawford Emmett D | Polyester compositions containing cyclobutanediol having a certain combination of inherent viscosity and high glass transition temperature and articles made therefrom |
| US8193302B2 (en) | 2005-10-28 | 2012-06-05 | Eastman Chemical Company | Polyester compositions which comprise cyclobutanediol and certain phosphate thermal stabilizers, and/or reaction products thereof |
| EP1940909B1 (en) * | 2005-10-28 | 2009-10-07 | Eastman Chemical Company | Restaurant smallware comprising polyester compositions formed from 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 1,4-cyclohexanedimethanol |
| US9598533B2 (en) | 2005-11-22 | 2017-03-21 | Eastman Chemical Company | Polyester compositions containing cyclobutanediol having a certain combination of inherent viscosity and moderate glass transition temperature and articles made therefrom |
| US7737246B2 (en) | 2005-12-15 | 2010-06-15 | Eastman Chemical Company | Polyester compositions which comprise cyclobutanediol, cyclohexanedimethanol, and ethylene glycol and manufacturing processes therefor |
| US9169388B2 (en) | 2006-03-28 | 2015-10-27 | Eastman Chemical Company | Polyester compositions which comprise cyclobutanediol and certain thermal stabilizers, and/or reaction products thereof |
| US8501287B2 (en) | 2007-11-21 | 2013-08-06 | Eastman Chemical Company | Plastic baby bottles, other blow molded articles, and processes for their manufacture |
| CN101868340B (zh) | 2007-11-21 | 2016-04-20 | 伊士曼化工公司 | 塑料乳瓶、其它吹塑物品及其制备方法 |
| US8198371B2 (en) | 2008-06-27 | 2012-06-12 | Eastman Chemical Company | Blends of polyesters and ABS copolymers |
| KR101025401B1 (ko) * | 2008-08-29 | 2011-03-28 | 앰코 테크놀로지 코리아 주식회사 | 디캡 장치 및 이를 이용한 반도체 패키지의 디캡 방법 |
| US20100099828A1 (en) * | 2008-10-21 | 2010-04-22 | Eastman Chemical Company | Clear Binary Blends of Aliphatic Polyesters and Aliphatic-Aromatic Polyesters |
| US8895654B2 (en) * | 2008-12-18 | 2014-11-25 | Eastman Chemical Company | Polyester compositions which comprise spiro-glycol, cyclohexanedimethanol, and terephthalic acid |
| US8420868B2 (en) | 2010-12-09 | 2013-04-16 | Eastman Chemical Company | Process for the preparation of 2,2,4,4-tetraalkylcyclobutane-1,3-diols |
| US8394997B2 (en) | 2010-12-09 | 2013-03-12 | Eastman Chemical Company | Process for the isomerization of 2,2,4,4-tetraalkylcyclobutane-1,3-diols |
| US8420869B2 (en) | 2010-12-09 | 2013-04-16 | Eastman Chemical Company | Process for the preparation of 2,2,4,4-tetraalkylcyclobutane-1,3-diols |
| US20130217830A1 (en) | 2012-02-16 | 2013-08-22 | Eastman Chemical Company | Clear Semi-Crystalline Articles with Improved Heat Resistance |
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| US2394306A (en) * | 1938-09-20 | 1946-02-05 | Hentrich Winfrid | Process of producing nitrogenous condensation products |
| BE655915A (no) * | 1963-11-18 | |||
| BE754871A (fr) * | 1969-08-19 | 1971-01-18 | Gen Electric | Resine de polycarbonate stabilisee et pigmentee |
| US4159261A (en) * | 1977-01-26 | 1979-06-26 | Dart Industries Inc. | Stabilization of vinyl halide resins |
| US4504615A (en) * | 1979-12-21 | 1985-03-12 | Phillips Petroleum Company | Treating polymers of ethylene |
| EP0058447A1 (en) * | 1981-02-13 | 1982-08-25 | Akzo N.V. | Stabilizer composition for polymers or copolymers of vinyl chloride, polymer composition comprising such a stabilizer composition and shaped articles prepared therefrom |
| US4374352A (en) * | 1981-07-21 | 1983-02-15 | Veeco/Macronetics Inc. | AC Induction motor braking system |
| JPS61174270A (ja) * | 1985-01-29 | 1986-08-05 | Kyowa Chem Ind Co Ltd | 耐発錆性ないし耐着色性賦与剤 |
| JPS62129329A (ja) * | 1985-11-30 | 1987-06-11 | Mitsui Petrochem Ind Ltd | 着色の少ないポリオレフイン組成物 |
| US4963606A (en) * | 1989-09-06 | 1990-10-16 | Ethyl Corporation | Thermally stabilized styrenic polymer-based thermoplastic formulations |
-
1990
- 1990-11-15 DE DE4036359A patent/DE4036359A1/de not_active Withdrawn
-
1991
- 1991-11-05 TW TW080108719A patent/TW203068B/zh active
- 1991-11-07 ES ES91119003T patent/ES2103765T3/es not_active Expired - Lifetime
- 1991-11-07 AT AT91119003T patent/ATE152469T1/de not_active IP Right Cessation
- 1991-11-07 DE DE59108691T patent/DE59108691D1/de not_active Expired - Fee Related
- 1991-11-07 DK DK91119003.1T patent/DK0485891T3/da active
- 1991-11-07 EP EP91119003A patent/EP0485891B1/de not_active Expired - Lifetime
- 1991-11-13 FI FI915352A patent/FI915352A/fi unknown
- 1991-11-13 HU HU913548A patent/HU209722B/hu not_active IP Right Cessation
- 1991-11-13 MX MX9102052A patent/MX9102052A/es not_active IP Right Cessation
- 1991-11-13 JP JP3297430A patent/JPH04268349A/ja not_active Withdrawn
- 1991-11-13 MY MYPI91002094A patent/MY109712A/en unknown
- 1991-11-13 US US07/791,448 patent/US5331034A/en not_active Expired - Fee Related
- 1991-11-14 IE IE397391A patent/IE913973A1/en unknown
- 1991-11-14 ZA ZA919019A patent/ZA919019B/xx unknown
- 1991-11-14 CS CS913456A patent/CS345691A3/cs unknown
- 1991-11-14 BR BR919104964A patent/BR9104964A/pt not_active Application Discontinuation
- 1991-11-14 CA CA002055528A patent/CA2055528A1/en not_active Abandoned
- 1991-11-14 AU AU87822/91A patent/AU640061B2/en not_active Ceased
- 1991-11-14 NO NO914461A patent/NO304075B1/no not_active IP Right Cessation
- 1991-11-15 KR KR1019910020339A patent/KR920009929A/ko not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU640061B2 (en) | 1993-08-12 |
| HU209722B (en) | 1994-10-28 |
| BR9104964A (pt) | 1992-06-23 |
| DE4036359A1 (de) | 1992-05-21 |
| US5331034A (en) | 1994-07-19 |
| IE913973A1 (en) | 1992-05-20 |
| CS345691A3 (en) | 1992-06-17 |
| CA2055528A1 (en) | 1992-05-16 |
| HUT59434A (en) | 1992-05-28 |
| ES2103765T3 (es) | 1997-10-01 |
| DE59108691D1 (de) | 1997-06-05 |
| JPH04268349A (ja) | 1992-09-24 |
| EP0485891A2 (de) | 1992-05-20 |
| KR920009929A (ko) | 1992-06-25 |
| NO914461L (no) | 1992-05-18 |
| MY109712A (en) | 1997-04-30 |
| HU913548D0 (en) | 1992-01-28 |
| DK0485891T3 (da) | 1997-10-27 |
| FI915352A (fi) | 1992-05-16 |
| FI915352A0 (fi) | 1991-11-13 |
| ZA919019B (en) | 1992-07-29 |
| EP0485891B1 (de) | 1997-05-02 |
| EP0485891A3 (en) | 1993-03-10 |
| ATE152469T1 (de) | 1997-05-15 |
| NO914461D0 (no) | 1991-11-14 |
| MX9102052A (es) | 1993-01-01 |
| TW203068B (no) | 1993-04-01 |
| AU8782291A (en) | 1992-05-21 |
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