NO313412B1 - Nye NH2-modifiserte 6-aminouraciler som stabilisatorer for halogenholdige polymerer - Google Patents
Nye NH2-modifiserte 6-aminouraciler som stabilisatorer for halogenholdige polymerer Download PDFInfo
- Publication number
- NO313412B1 NO313412B1 NO19993181A NO993181A NO313412B1 NO 313412 B1 NO313412 B1 NO 313412B1 NO 19993181 A NO19993181 A NO 19993181A NO 993181 A NO993181 A NO 993181A NO 313412 B1 NO313412 B1 NO 313412B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- tert
- acid
- butyl
- substituted
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract description 31
- 229910052736 halogen Inorganic materials 0.000 title claims abstract description 8
- 150000002367 halogens Chemical class 0.000 title claims abstract description 8
- 239000003381 stabilizer Substances 0.000 title claims description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
- 239000000460 chlorine Substances 0.000 claims abstract description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 5
- -1 fatty acid ester Chemical class 0.000 claims description 105
- 239000010457 zeolite Substances 0.000 claims description 57
- 229910021536 Zeolite Inorganic materials 0.000 claims description 41
- 239000000463 material Substances 0.000 claims description 21
- 239000011701 zinc Substances 0.000 claims description 20
- 229910052725 zinc Inorganic materials 0.000 claims description 19
- 239000004014 plasticizer Substances 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 229920005862 polyol Polymers 0.000 claims description 11
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 10
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 10
- 150000003077 polyols Chemical class 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 229910052782 aluminium Inorganic materials 0.000 claims description 9
- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 8
- 239000000194 fatty acid Substances 0.000 claims description 8
- 229930195729 fatty acid Natural products 0.000 claims description 8
- 239000000314 lubricant Substances 0.000 claims description 8
- 239000000049 pigment Substances 0.000 claims description 7
- 239000003963 antioxidant agent Substances 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000000945 filler Substances 0.000 claims description 5
- 125000001624 naphthyl group Chemical class 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 4
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 claims description 4
- 229910001701 hydrotalcite Inorganic materials 0.000 claims description 4
- 229960001545 hydrotalcite Drugs 0.000 claims description 4
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 3
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 claims description 3
- 235000013539 calcium stearate Nutrition 0.000 claims description 2
- 239000008116 calcium stearate Substances 0.000 claims description 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004408 titanium dioxide Substances 0.000 claims description 2
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 2
- 150000002016 disaccharides Chemical class 0.000 claims 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 47
- 229910052717 sulfur Inorganic materials 0.000 abstract description 8
- 238000000034 method Methods 0.000 abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 abstract description 3
- 239000004800 polyvinyl chloride Substances 0.000 abstract description 2
- 229920000915 polyvinyl chloride Polymers 0.000 abstract description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 230000000087 stabilizing effect Effects 0.000 abstract 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical class O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 40
- 150000002148 esters Chemical class 0.000 description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 229920001577 copolymer Polymers 0.000 description 18
- 229910052751 metal Inorganic materials 0.000 description 16
- 239000002184 metal Substances 0.000 description 16
- 239000011575 calcium Substances 0.000 description 15
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 14
- 229910052791 calcium Inorganic materials 0.000 description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 12
- 229910052749 magnesium Inorganic materials 0.000 description 12
- 239000011777 magnesium Substances 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 239000004593 Epoxy Substances 0.000 description 11
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 10
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 10
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 10
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 10
- 239000000344 soap Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 9
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 9
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 9
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 9
- 150000007942 carboxylates Chemical class 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 9
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 150000001735 carboxylic acids Chemical class 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 239000005038 ethylene vinyl acetate Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 8
- 229910052700 potassium Inorganic materials 0.000 description 8
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- 239000007983 Tris buffer Substances 0.000 description 7
- 229910052788 barium Inorganic materials 0.000 description 7
- 150000002170 ethers Chemical class 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 7
- 230000006641 stabilisation Effects 0.000 description 7
- 238000011105 stabilization Methods 0.000 description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 150000001342 alkaline earth metals Chemical class 0.000 description 6
- 229910052681 coesite Inorganic materials 0.000 description 6
- 229910052906 cristobalite Inorganic materials 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 229910001385 heavy metal Inorganic materials 0.000 description 6
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- 235000013772 propylene glycol Nutrition 0.000 description 6
- 229960004063 propylene glycol Drugs 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 235000012239 silicon dioxide Nutrition 0.000 description 6
- 229910052682 stishovite Inorganic materials 0.000 description 6
- 229910052712 strontium Inorganic materials 0.000 description 6
- 229910052905 tridymite Inorganic materials 0.000 description 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 5
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 5
- YENQKAGAGMQTRZ-UHFFFAOYSA-N 1-cyanoethenyl prop-2-enoate Chemical compound C=CC(=O)OC(=C)C#N YENQKAGAGMQTRZ-UHFFFAOYSA-N 0.000 description 5
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 5
- 229910052684 Cerium Inorganic materials 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 235000006708 antioxidants Nutrition 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 5
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 5
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 5
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 5
- 229940117969 neopentyl glycol Drugs 0.000 description 5
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 5
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 5
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 5
- 235000019260 propionic acid Nutrition 0.000 description 5
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 229920000638 styrene acrylonitrile Polymers 0.000 description 5
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- YEWBOZCFGXOUQW-UHFFFAOYSA-N 2,6,7-trioxa-1-phosphabicyclo[2.2.2]octan-4-ylmethanol Chemical compound C1OP2OCC1(CO)CO2 YEWBOZCFGXOUQW-UHFFFAOYSA-N 0.000 description 4
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 4
- ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 4
- CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- KRADHMIOFJQKEZ-UHFFFAOYSA-N Tri-2-ethylhexyl trimellitate Chemical compound CCCCC(CC)COC(=O)C1=CC=C(C(=O)OCC(CC)CCCC)C(C(=O)OCC(CC)CCCC)=C1 KRADHMIOFJQKEZ-UHFFFAOYSA-N 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 4
- 235000011037 adipic acid Nutrition 0.000 description 4
- 125000001931 aliphatic group Chemical class 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical group CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 4
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 229910052593 corundum Inorganic materials 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- 229940093476 ethylene glycol Drugs 0.000 description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 229910052746 lanthanum Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- FPQJEXTVQZHURJ-UHFFFAOYSA-N n,n'-bis(2-hydroxyethyl)oxamide Chemical compound OCCNC(=O)C(=O)NCCO FPQJEXTVQZHURJ-UHFFFAOYSA-N 0.000 description 4
- 150000002815 nickel Chemical class 0.000 description 4
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 150000003014 phosphoric acid esters Chemical class 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 4
- 229910052761 rare earth metal Inorganic materials 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- 125000005591 trimellitate group Chemical group 0.000 description 4
- 229910001845 yogo sapphire Inorganic materials 0.000 description 4
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- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
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- JNXDCMUUZNIWPQ-UHFFFAOYSA-N trioctyl benzene-1,2,4-tricarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC)C(C(=O)OCCCCCCCC)=C1 JNXDCMUUZNIWPQ-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- IGQFKXMQIMEIJV-UHFFFAOYSA-N tris(11-methyldodecyl) benzene-1,2,4-tricarboxylate Chemical compound CC(C)CCCCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCCCCC(C)C)C(C(=O)OCCCCCCCCCCC(C)C)=C1 IGQFKXMQIMEIJV-UHFFFAOYSA-N 0.000 description 1
- KOWVWXQNQNCRRS-UHFFFAOYSA-N tris(2,4-dimethylphenyl) phosphate Chemical compound CC1=CC(C)=CC=C1OP(=O)(OC=1C(=CC(C)=CC=1)C)OC1=CC=C(C)C=C1C KOWVWXQNQNCRRS-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- WDRCVXGINNJWPH-UHFFFAOYSA-N tris(6-methylheptyl) benzene-1,2,4-tricarboxylate Chemical compound CC(C)CCCCCOC(=O)C1=CC=C(C(=O)OCCCCCC(C)C)C(C(=O)OCCCCCC(C)C)=C1 WDRCVXGINNJWPH-UHFFFAOYSA-N 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
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- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
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- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
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- 239000004711 α-olefin Substances 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
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- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
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Abstract
Forbindelse med generell formel. hvor. Y er oksygen eller svovel,. Ri °9 Ruavhengig av hverandre er C.-alkyl, C.-alkenyl, usubstituert eller. C-alkoksy-, C.-sykloalkyl-, -0H- og/eller Cl-substituert C-alkyl, C_-sykloalkyl, fenyl eller C7_9-f enylalkyl. som er usubstituert eller substituert. på fenylringen med C-alkyl, C-alkoksy, C.-sykloalkyl, -0H og/eller . Cl,. Rer usubstituert C,.-alkyl eller C.-alkyl substituert opp tilganger med. -0H, C.-alkoksy, fenoksy, C.-alkyl-fenoksy, C.-alkoksyfenyl, -C=0(ORJ. og/eller -0-COR, eller C.-alkenyl, C_. -sykloalkyl eller mono- til tri-OH-,. C-alkyl, -C^-alkoksy, -C=0(OR4) -. og/eller -0-COR-substituert fenyl eller naftyl,og Rer Cj.u-alkyl.Forbindelsene er egnet som stabilisatorer for halogenholdige polymerer.
Description
Oppfinnelsen angår 1,3-disubstituerte 6-aminouraciler med formel I angitt nedenfor, og som er ment for stabilisering av klorholdige polymerer, særlig PVC.
PVC kan stabiliseres med en rekke additiver. Bly-, barium- og kadmium-forbindelser er særlig egnet for dette formål, men de er i dag kontroversielle av økologiske grunner eller på grunn av innholdet av tungmetaller (jf. "Kunststoffadditive", R. Gåchter/H. Muller, Carl Hanser Verlag, 3. utg., 1989, p. 303-311, og "Kunststoff Handbuch PVC", volum 2/1, W. Becker/D. Braun, Carl Hanser Verlag, 2. utg., 1985, p. 531-538; og også Kirk-Othmer: "Encyclopedia of Chemical Technology", 4. utg., 1994, vol. 12, Heat Stabilizers p. 1071-1091). Søkingen etter effektive stabilisatorer og stabilisatorkombinasjoner som er fri for bly, barium og kadmium fortsetter derfor.
1,3-disubstituerte aminouraciler er allerede beskrevet i US 3 436 362, US 4 656 209, US 4 352 903 og EP-A-0 768 336, og kan fremstilles ved kjente fremgangsmåter i ett (eller flere) prosesstrinn.
Med den foreliggende oppfinnelse er det nå funnet 1,3-disubstituerte 6-aminouraciler med den generelle formel I
hvor
Y er oksygen, og
Ri og R2 er uavhengig av hverandre Q.ig-alkyl, og
R3 er Ci_i8-alkyl substituert med -OH, C5.8-sykloalkyl, eller mono-, di- eller tri-OH-, -CM-alkyl-, -CM-alkoksy-, -C=0(OR4)- og/eller -0-COR4-substituert fenyl eller naftyl eller benzyl, hvor R4 er Ci.]2-alkyl.
Med oppfinnelsen tilveiebringes også et materiale som er kjennetegnet ved at det omfatter en klorholdig polymer og minst én forbindelse med generell formel I.
Oppfinnelsen angår også anvendelse av en forbindelse med generell formel I som stabilisator for halogenholdige polymerer.
For forbindelser med formel I:
Ci^-alkyl er for eksempel metyl, etyl, n-propyl, isopropyl, n-, i-, sek- eller t-butyl, C5_i8-alkyl er for eksempel pentyl, heksyl, heptyl, oktyl, 2-etylheksyl, i-oktyl, decyl, nonyl, undecyl, dodecyl, pentadecyl eller heksadecyl.
Det foretrekkes metyl, etyl, propyl og butyl, særlig metyl.
Ci_4-alkoksy er for eksempel metoksy, etoksy, propoksy, n-, i- og tert-butoksy. Metoksy og etoksy er foretrukket.
C5.8-sykloalkyl er for eksempel syklopentyl, sykloheksyl, sykloheptyl eller syklooktyl, fortrinnsvis sykloheksyl.
Dersom det aromatiske radikal er substituert, så er det fortrinnsvis substituert med tre, to eller fortrinnsvis én substituent, og særlig er substituentene hydroksyl, metyl, etyl, tert-butyl, metoksy eller etoksy.
Det foretrekkes forbindelser med formel I hvor Y er oksygen, og slike hvor radikalene Ri og R2 uavhengig av hverandre er Q.g-alkyl.
Det foretrekkes også forbindelser med formel I hvor R3 er -OH-substituert Ci-n-alkyl, sykloheksyl, -OH-, Ci.4-alkyl-, C^-alkoksy-, -C=0(OR4)- og/eller -0-COR4-substituert fenyl eller naftyl. Særlig foretrukket er forbindelser med formel I hvor Ri og R2 er CM-alkyl og R3 er -OH-substituert CM-alkyl, benzyl, fenyl, -OH-substituert fenyl, eller fenyl som er substituert med -OH og 1 til 3 ganger med Ci_4-alkyl.
For å oppnå stabilisering av den klorholdige polymer, må forbindelsene med formel I anvendes i en hensiktsmessig mengde fra 0,01 til 10 vekt%, fortrinnsvis fra 0,05 til 5 vekt%, og særlig fra 0,1 til 3 vekt%.
Det er også mulig å benytte forbindelser med den generelle formel I i kombinasjon med vanlige additiver og stabilisatorer, for eksempel sammen med polyoler og disakkaridalkoholer og/eller perkloratforbindelser og/eller glysidylforbindelser og/eller zeolittforbindelser og/eller lagoppbygde gitterforbindelser (hydrotalsitter), og også for eksempel lysstabilisatorer. Eksempler på slike ytterligere forbindelser er listet opp og belyst nedenfor.
Polyoler og disakkaridalkoholer
Eksempler på egnede forbindelser av denne type er:
pentaerytritol, dipentaerytritol, tripentaerytritol, trimetyloletan, bis-trimetylolpropan, inositol (syklitoler), polyvinylalkohol, bis-trimetyloletan, trimetylolpropan, sorbitol (heksitoler), maltitol, isomaltitol, cellobiitol, laktitol, lycazin, mannitol, laktose, leukrose, tris(hydroksyetyl) isocyanurat, tris(hydroksypropyl)isocyanurat, palatinitol, tetrametylol-sykloheksanol, tetrametylolsyklopentanol, tetrametylolsyklopyranol, xylitol, arabinitol (pentitoler), tetritoler, glyserol, diglyserol, polyglyserol, tiodiglyserol og 1-O-a-D-glyco-pyranosyl-D-mannitol-dihydrat.
Av disse foretrekkes disakkaridalkoholer.
Det er også mulig å anvende polyolsiruper, så som sorbitol-, mannitol- og maltitol-sirup. Polyolene kan benyttes i en mengde for eksempel fra 0,01 til 20, hensiktsmessig fra 0,1 til 20, og særlig fra 0,1 til 10 vektdeler per 100 vektdeler PVC.
Perkloratforbindelser
Eksempler er slike som har formel M(C104)n, hvor M er Li, Na, K, Mg, Ca, Sr, Ba, Zn, Al, La eller Ce. Avhengig av valensen på M, vil indeksen n være 1, 2 eller 3. Perkloratsaltene kan være til stede som løsninger, eller de kan være komplekser med alkholer (polyoler, syklodekstriner), eteralkoholer eller esteralkoholer. Esteralkoholene innbefatter også polyol-partialestere. I tilfelle flerverdige alkoholer eller polyoler, vil deres dimerer, trimerer, oligomerer og polymerer også være egnet, så som di-, tri-, tetra-og polyglykoler, og også di-, tri- og tetrapentaerytritol eller polyvinylalkohol i forskjellige polymerisasjonsgrader. Andre egnede løsningsmidler er fosfatestere og også sykliske og asykliske karbonater.
I denne sammenheng kan perkloratsaltene benyttes i forskjellige, vanlig forekommende former, for eksempel som et salt eller som en løsning i vann eller et organisk løsningsmiddel som sådan, eller absorbert på et bærermateriale, så som PVC, Ca-silikat, zeolitter eller hydrotalsitter, eller bundet ved en kjemisk reaksjon i et hydrotalsitt eller i en annen lagoppbygd gitterforbindelse. Som polyol-partialestere foretrekkes glyserolmonoetere og glyserolmonotioetere.
Ytterligere utførelsesformer er beskrevet i EP 0 394 547,
EP 0 457 471 og WO 94/24200.
Perkloratene kan benyttes i en mengde for eksempel fra 0,001 til 5, hensiktsmessig fra 0,01 til 3, og særlig foretrukket fra 0,01 til 2 vektdeler per 100 vektdeler PVC.
Glysidylforbindelser
Disse inneholder glysidylgruppen
bundet direkte til karbon-, oksygen-, nitrogen- eller svovelatomer, og i slike forbindelser er enten både Ri og R3 hydrogen og R2 er hydrogen eller metyl, og n er 0, eller Rj og R3 er sammen -CH2-CH2- eller -CH2-CH2-CH2-, og i dette tilfellet er R2 hydrogen og n er 0 eller 1.
I) Glysidylestere og (3-metylglysidylestere kan fremstilles ved å omsette en forbindelse som har minst en karboksylgruppe i molekylet med epiklorhydrin, glyseroldiklorhydrin eller (3-metylepiklorhydrin. Reaksjonen finner hensiktsmessig sted i nærvær av baser.
Som forbindelser med minst en karboksylgruppe i molekylet, er det mulig å anvende alifatiske karboksylsyrer. Eksempler på slike karboksylsyrer er glutarsyre, adipinsyre, pimelinsyre, suberinsyre, acelainsyre og sebasinsyre, eller dimerisert eller trimerisert linoleinsyre, akrylsyre og metakrylsyre, kaproinsyre, kaprylsyre, laurinsyre, myrestinsyre, palmitinsyre, stearinsyre og pelargonsyre, og også syrene nevnt i forbindelse med organosink-forbindelsene.
Det er imidlertid også mulig å benytte sykloalifatiske karboksylsyrer, som for eksempel sykloheksankarboksylsyre, tetrahydroftalsyre, 4-metyltetrahydroftalsyre, heksahydroftal-syre eller 4-metylheksahydroftalsyre.
Aromatiske karboksylsyrer kan også anvendes, for eksempel benzoinsyre, ftalinsyre, isoftalinsyre, trimellitinsyre og pyromellitinsyre.
Det er likeledes mulig å gjøre bruk av karboksyl-terminerte addukter av for eksempel trimellitinsyre med polyoler, så som glyserol eller 2,2-bis-(4-hydroksy-sykloheksyl)propan.
Andre epoksidforbindelser som kan anvendes i forbindelse med denne oppfinnelse, er gitt i EP 0 506 617.
II) Glysidyletere eller (i-metylglysidyletere fremstilt ved å omsette en forbindelse som har minst en fri alkoholisk hydroksylgruppe og/eller fenolisk hydroksylgruppe med et passende substituert epiklorhydrin under alkaliske betingelser eller i nærvær av en sur katalysator med etterfølgende alkalibehandling.
Etere av denne type er dannet for eksempel av asykliske alkoholer, så som etylenglykol, dietylenglykol og høyere poly(oksyetylen)glykoler, propan-1,2-diol eller poly(oksypropylen)glykoler, propan-1,3-diol, butan-1,4-diol, poly(oksytetra-metylen)glykoler, pentan-l,5-diol, heksan-l,6-diol, heksan-2,4,6-triol, glyserol, 1,1,1-trimetylolpropan, bis-(trimetylolpropan, pentaerytritol, sorbitol, og av polyepi-klorhydriner, butanol, amylalkohol, pentanol, og av monorunksjonelle alkoholer som isooktanol, 2-etylheksanol, isodekanol og også C7.9-alkanol og C^n-alkanol- blandinger. De er imidlertid også dannet av for eksempel sykloalifatiske alkoholer som 1,3- eller 1,4-dihydroksysykloheksan, bis-(4-hydroksysykloheksyl)metan, 2,2-bis-(4-hydroksysyklo-heksyl)propan eller l,l-bis-(hydroksymetyl)sykloheks-3-en, eller de har aromatiske kjerner så som N,N-bis-(2-hydroksyetyl)anilin eller p,p'-bis-(2-hydroksyetylamino)-defenylmetan.
Epoksidforbindelsen kan også være dannet av mononukleære fenoler, så som for eksempel fenol, resorsinol eller hydrokinon, eller de kan være basert på polynukleære fenoler, som for eksempel på bis-(4-hydroksyfenyl)metan, 2,2-bis-(4-hydroksyfenyl)propan, 2,2-bis-(3,5-dibrom-4-hydroksyfenyl)propan, på 4,4'-dihydroksy-difenylsulfon eller på kondensater av fenoler og formaldehyd fremstilt under sure betingelser, så som fenol-novolaker.
Eksempler på ytterligere mulige terminale epoksider er: glysidyl-l-naftyleter, glysidyl-2-fenylfenyleter, 2-bifenylyl-glysidyleter, N-(2,3-epoksypropyl)ftalimid og 2,3-epoksy-propyl-4-metoksyfenyleter.
III) N-glysidylforbindelser som kan fremstilles ved dehydroklorering av omsetningsproduktet av epiklorhydrid med aminer som inneholder minst ett amin-hydrogenatom. Disse aminer er for eksempel anilin, N-metylanilin, toluiden, n-butylamin, bis-(4-aminofenyl)metan, m-xylylendiamin eller bis-(4-metylamino-fenyl)metan, og også N,N,0-triglysidyl-m-aminofenol eller N,N,0-triglysidyl-p-aminofenol.
N-glysidylforbindelsene kan imidlertid også innbefatte N,N'-di-, N,N',N"-tri- og N,N',N",N"'-tetraglysidyl-derivater av sykloalkylenureaer, så som etylenurea eller 1,3-propylenurea og N,N'-diglysidyl-derivater av hydantoiner, så som 5,5-dimetylhydantoin eller glykoluril og triglysidylisocyanurat.
IV) S-glysidylforbindelser som di-S-glysidyl-derivater av ditioler, så som for eksempel etan-l,2-ditiol eller bis-(4-merkaptometylfenyl)eter. . V) Epoksyforbindelser som har et radikal med formelen over hvor Ri og R3 sammen er - CH2-CH2- og n er 0, er bis-(2,3-epoksysyklopentyl)eter, 2,3-epoksysyklo-pentylglysidyleter eller l,2-bis-(2,3-epoksysyklopentyloksy)etan. Et epoksyharpiks som har et radikal med formel I hvor Ri og R3 sammen er —CH2-CH2- og n er 1, er for eksempel (3'4'-epoksy-6'-metylsykloheksyl)metyl-3,4-epoksy-6-metylsykloheksan-karboksylat.
Eksempler på egnede terminal-epoksider er:
a) flytende bisfenol A-diglysidyletere, så som Araldit®GY 240, Araldit®GY 250, Araldit®GY 260, Araldit®GY 266, Araldit®GY 2600, Araldit®MY 790; b) faste bisfenol A-diglysidyletere, så som Araldit®GT 6071, Araldit®GT 7071, Araldit®GT 7072, Araldit®GT 6063, Araldit®GT 7203, Araldit®GT 6064, Araldit®GT 7304, Araldit®GT 7004, Araldit®GT 6084, Araldit®GT 1999, Araldit®GT 7077, Araldit®GT 6097, Araldit®GT 7097, Araldit®GT 7008, Araldit®GT 6099, Araldit®GT 6608, Araldit®GT 6609, Araldit®GT 6610; c) flytende bisfenol F-diglysidyletere, så som Araldit®GY 281, Araldit®PY 302, Araldit®PY 306; d) faste polyglysidyletere av tetrafenyletan, så som CG Epoxy Resin®0163; e) faste og flytende polyglysidyletere av fenol-formaldehyd-novalak, så som EPN 1138, EPN 1139, GY 1180, PY 307; f) faste og flytende polyglysidyletere av o-kresol-formaldehyd-novolak, så som ECN 1235, ECN 1273, ECN 1280, ECN 1299; g) flytende glysidyletere av alkoholer så som Shell® Glycidyl ether 162, Araldit®DY 0390, Araldit®DY 0391; h) flytende glysidyletere av karboksylsyrer så som Shell®Cardura E tereftalsyre-ester, trimellitilsyre-ester, Araldit®PY 284; i) faste heterosykliske epoksyharpikser (triglysidylisocyanurat), så som Araldit®PT 810; j) flytende sykloalifatiske epoksyharpikser, så som Araldit®CY 179;
k)flytende N,N,0-triglysidyletere av p-aminofenol, så som Araldit®MY 0510; 1) tetraglysidyl-4,4'-metylenbenzamin eller N,N,N',N'-tetraglysidylamino-fenylmetan, så som Araldit®MY 720, Araldit®MY 721.
Det foretrekkes å anvende epoksyforbindelser som har to funksjonelle grupper. I prinsippet er det imidlertid også mulig å benytte epoksyforbindelser som har en, tre eller flere funksjonelle grupper.
Det anvendes overveiende epoksyforbindelser, særlig diglysidylforbindelser, som har aromatiske grupper.
Om ønsket, så er det også mulig å benytte en blanding av forskjellige epoksyforbindelser. Som terminale epoksyforbindelser er det særlig foretrukket diglysidyletere basert på bisfenoler, så som på 2,2-bis-(4-hydroksyfenyl)propan (bisfenol A), bis-(4-hydroksyfenyi)metan eller blandinger av bis-(orto/para-hydroksyfenyl)metan (bisfenol
F).
De terminale epoksyforbindelser kan benyttes i en mengde på fortrinnsvis minst 0,1 del, for eksempel fra 0,1 til 50, hensiktsmessig fra 1 til 30, og særlig fra 1 til 25 vektdeler per 100 vektdeler PVC.
Hydrotalsitter
Den kjemiske sammensetning av disse forbindelser er kjent av fagfolk på området, for eksempel fra patenter DE 3 843 581, US 4 000 100, EP 0 062 813 og WO 93/20135. Forbindelser i serien av hydrotalsitter kan beskrives med den følgende generelle formel M2YxM^(OH)2(AbU*dH20
hvor
M<2+> = ett eller flere metaller valgt blant Mg, Ca, Sr, Zn og Sn,
M<3+> = Al eller B,
A" er et anion med valens n,
ber et tall fra 1-2,
0<x<0,5,
m er et tall fra 0 til 20.
Fortrinnsvis
An = Off, C104', HCO3<->, CH3COO<->, C6H5COO\ C03<2>-, (CHOHCOO)2<2->, (CH2COO)2<2->, CH3CHOHCOO<->, HPO3<-> eller HP042";
Eksempler på hydrotalsitter er
Al203.6MgO.C02.12H20 (i), Mg4j5Al2(OH)13.C03.3,5H20 (ii),
4MgO.Al203.C02.9H20 (iii), 4MgO.Al203.C02.6H20,
Zn0.3MgO.Al203.C02.8-9H20 og Zn0.3MgO.Al203.C02.5-6H20.
Det foretrekkes spesielt typer i, ii og iii.
Zeolitter (alkalimetall- og jordalkalimetall-alumosilikater)
Disse kan beskrives med den følgende generelle formel
M^n[(A102)x(Si02)y].wH20
hvor n er ladningen på kationet M,
M er et grunnstoff fra den første eller andre hovedgruppe, så som Li, Na, K, Mg, Ca, Sr eller Ba,
y:x er et tall fra 0,8 til 15, fortrinnsvis fra 0,8 til 1,2, og
w er et tall fra 0 til 300, fortrinnsvis fra 0,5 til 30..
Eksempler på zeolitter er natriumaluminosilikater med formlene
Na12Al,2Si12048.27H20 [zeolitt A], Na6Al6Si6024.2 NaX.7,5H20, XOH, halogen, CI04 [sodalitt]; Na6Al6Si3o072.24H20; Na8Al8Si40O96.24H2O; Na16Al16Si24O80.16H2O; Na16Al16Si32096.16H20; Na56Al56Si136O384.250H2O [zeolitt Y], Na86Al86Si106O384.264H2O [zeolitt X];
eller zeolittene som kan fremstilles ved hel eller delvis utbytting av Na-atomene med Li-, K-, Mg-, Ca-, Sr- eller Zn-atomer, så som (Na^ioAl^Si^Ow^O^O; Ca4>5Na3[(AlO2)12(SiO2)12].30H2O;K9Na3[(AlO2)12(SiO2)12].27H2O.
Foretrukne zeolitter er slike med formlene
Nai2Al12Sii2048.27H20 [zeolitt A],
Na6Al6Si6024.2NaX.7,5H20, X = OH, Cl, C104, l/2C03[sodalitt] Na6Al6Si3o072.24H20,
Na8AlgSi4o096.24H20,
Na,6Al16Si24O80.16H2O,
Na,6Al16Si32096.16H20,
Na56Al56Si136O384.250H2O [zeolitt Y],
Na86Al86Si106O384.264H2O [zeolitt X]
og de X- og Y-zeolitter som har Al/Si-forhold på ca. 1:1,
eller zeolittene som kan fremstilles ved hel eller delvis utbytting av Na-atomene med Li-, K-, Mg-, Ca-, Sr-, Ba- eller Zn-atomer, så som (Na,K)i0Al10Si22O64.20H2O; Ca4,5Na3[(AlO2)12(SiO2)12].30H2O;K9Na3[(AlO2)12(SiO2)12].27H2O.
De angitte zeolitter kan også ha lavere vanninnhold eller være vannfrie. Ytterligere egnede zeolitter er: Na2OAl203 (2 til 5)Si02-(3,5 til 10)H2O [zeolitt P]
Na2OAl203-2Si02(3,5 til 10)H2O [zeolitt MAP]
eller zeolittene som kan fremstilles ved hel eller delvis utbytting av Na-atomene med Li-, K-, eller H-atomer, så som
(LiNa^H^oMoSi^Oé,. 20H2O.
K9Na3[(A102)12(Si02)12]. 27H20
K4Al4Si4Oi6-6H20[zeolitt K-F]
Na8Al8Si40O96.24H2O [zeolitt D], som beskrevet av Barrer et al., J. Chem. Soc. 1952, 1561-71, og i US 2 950 952;
Også egnet er de følgende zeolitter;
K-offretitt, som beskrevet i EP-A-400 961;
zeolitt R, som beskrevet i GB 841 812;
zeolitt LZ-217, som beskrevet i US 4 503 023;
Ca-fri zeolitt LZ-218, som beskrevet i US 4 333 859;
zeolitt T, zeolitt LZ-220, som beskrevet i US 4 503 023; Na3K6Al9Si27072. 21H20 [zeolitt L];
zeolitt LZ-211, som beskrevet i US 4 503 023;
zeolitt LZ-212, som beskrevet i US 4 503 023;
zeolitt O, zeolitt LZ-217, som beskrevet i US 4 503 023;
zeolitt LZ-219 som beskrevet i US 4 503 023;
zeolitt Rho, zeolitt LZ-214, som beskrevet i US 4 503 023;
zeolitt ZK-19, som beskrevet i Am. Mineral. 54 1607 (1969);
zeolitt W(K-M), som beskrevet i Barrer et al., J. Chem. Soc. 1956, 2882, Na30Al30Si66Oi92. 98H20 [zeolitt ZX-5, zeolitt Q]
Særlig foretrukket er zeolitt P-kvalitetene med formelen over hvor x er fra 2 til 5 og y fra 3,5 til 10, og særlig foretrukket er zeolitt MAP med den angitte formel hvor x er 2 og y er fra 3,5 til 10. Særlig aktuell er zeolitten Na-P, dvs. M er Na. Denne zeolitt forekommer vanligvis i variantene Na-P-1, Na-P-2 og Na-P-3, som er ulike ved at de har forskjellig kubisk, tetragonal eller ortorombisk struktur (R. M. Barrer, B. M. Munday, J. Chem. Soc. A 1971, 2909 - 14). I denne litteraturreferanse beskrives også fremstilling av zeolitt P-l og P-2. Ifølge referansen er zeolitt P-3 svært sjelden og derfor i realiteten uten praktisk interesse. Strukturen for zeolitt P-l tilsvarer gismonditt-strukturen kjent fra det ovennevnte atlas over zeolittstrukturer. I senere litteratur (EP-A-384 070) er det skilt mellom kubiske (zeolitt B eller Pc) og tetragonale (zeolitt Pj) zeolitter av P-typen. Det nevnes der også forholdsvis nye zeolitter av P-typen som har Si:Al-forhold på under 1,07:1. Disse er zeolitter med betegnelsen MAP eller MA-P, som står for "Maximum Aluminium P". Avhengig av fremstillingsprosessen kan zeolitt P også inneholde små fraksjoner av andre zeolitter. Høyrent zeolitt P er beskrevet i WO 94/26662.
Innen rammen for oppfinnelsen er det også mulig å anvende de findelte, vann-uløselige natriumaluminosilikater som er blitt utfelt og krystallisert i nærvær av vannløselige organiske eller uorganiske dispergeringsmidler. Disse kan tilsettes til reaksjonsblandingen på enhver ønsket måte, før eller under utfellingen og krystalliseringen.
Spesielt foretrukket er Na-zeolitt A og Na-zeolitt P.
Hydrotalsittene og/eller zeolittene kan benyttes i mengder for eksempel fra 0,1 til 20, hensiktsmessig fra 0,1 til 10 og særlig fra 0,1 til 5 vektdeler per 100 vektdeler halogenholdig polymer.
Andre vanlig additiver kan også tilsettes til blandingene ifølge oppfinnelsen, så som stabilisatorer, hjelpestoffer og bearbeidingshjelpemidler, hvor eksempler er alkalimetallforbindelser og jordalkalimetallforbindelser, smøremidler, mykgjørere, pigmenter, fyllstoffer, fosfitter, tiofosfitter, og tiofosfater, merkaptokarboksylsyreestere, epoksiderte fettsyreestere, antioksidanter, UV-absorbere og lysstabilisatorer, optiske klaringsmidler, slagfasthetsmodifiserende midler og bearbeidingshjelpemidler, gelingsmidler, antistatika, biosider, metall-passivatorer, flammehemmende midler og esemidler, antidugg-midler, kompatibilisatorer og midler mot utsvetting (jf. "Handbook of PVC Formulating" by E. J. Wickson, John Wiley & Sons, New York 1993).Eksempler på slike additiver er som følger: I. Fyllstoffer: Fyllstoffer (Handbook of PVC Formulating E. J. Wickson, John Wiley & Sons, Inc., 1993, p. 393-449) og forsterkende midler (Taschenbuch der Kunststoffadditive, R. Gåchter & H. Muller, Carl Hanser, 1990, p. 549-615) er for eksempel kalsiumkarbonat, dolomitt, wollastonitt, magnesiumoksid, magnes-iumhydroksid, silikater, kaolin, talk, glassfibre, glassperler, tremel, mika og metalloksider, eller metallhydroksider, sot, grafitt, stenmel, tungspat, glassfibrer, talk, kaolin og kritt. Kritt foretrekkes. Fyllstoffene kan anvendes i en mengde på fortrinnsvis minst 1 del,, for eksempel fra 5 til 200, hensiktsmessig fra 10 til 150, og særlig fra 15 til 100 vektdeler per 100 vektdeler PVC. II. Metallsåper: Metallsåper er først og fremst metallkarboksylater av fortrinnsvis forholdsvis langkjedete karboksylsyrer. Velkjente eksempler er stearater og laurater, men også oleater og salter av mer kortkjedete alkankarboksylsyrer. Alkylbenzosyrer er også sagt å være innbefattet blant metallsåpene. Metaller som kan nevnes, er Li, Na, K, Mg, Ca, Sr, Ba, Zn, Al, La, Ce og sjeldne jordmetaller. Det gjøres ofte bruk av det som er kjent som synergistiske blandinger, så som barium/sink-, magnesium/sink-, kalsium/sink-eller kalsium/magnesium/sink-stabilisatorer. Metallsåpene kan benyttes alene eller i blandinger. En oversikt over vanlige metallsåper er gitt i Ullmanns Encyclopedia of Industrial Chemistry, 5. utg., vol, A16 (1985), p. 361 ff.). Det er hensiktsmessig å anvende organiske metallsåper fra serien av alifatisk mettede C2-22-karboksylater, alifatisk umettede C3.22-karboksylater, alifatisk C2-22-karboksylater substituert med minst en OH-gruppe, sykliske og bisykliske karboksylater som har 5-22 karbonatomer, usubstituerte benzenkarboksylater som er substituert med minst en OH-gruppe og/eller med Ci_i6-alkyl, usubstituerte naftalenkarboksylater som er substituert med minst en OH-gruppe og/eller med Ci_i6-alkyl, fenyl-Ci.i6-alkylkarbokyater, naftyl Ci.i6-alkylkarboksylater eller usubstituerte eller Ci.n-alkyl-substituerte fenolater, talater og resinater.
Bestemte eksempler som kan nevnes er sink-, kalsium-, magnesium- eller barium-salter av enverdige karboksylsyrer som eddiksyre, propionsyre, smørsyre, valeriansyre, heksansyre, enantinsyre, oktansyre, neodekansyre, 2-etylheksansyre, pelargonsyre, dekansyre, undekansyre, dodekansyre, tridekansyre, myristinsyre, palmitinsyre, isostearinsyre, stearinsyre, 12-hydroksystearinsyre, behensyre, benzosyre, p-tert-butylbenzosyre, N,N-dimetylhydroksybenzosyre, 3,5-di-tert-butyl-4-hydroksybenzosyre, toluensyre, dimetylbenzosyre, etylbenzosyre, n-propylbenzosyre, salisylsyre, p-tert-oktylsalisylsyre og sorbinsyre; kalsium-, magnesium- og sink-saltene av monoestrene av toverdige karboksylsyrer som oksalsyre, malonsyre, ravsyre, glutarsyre, adipinsyre, fumarsyre, pentan-l,5-dikarboksylsyre, heksan-l,6-dikarboksylsyre, heptan-1,7-dikarboksylsyre, oktan-1,8-dikarboksylsyre, ftalsyre, isoftalsyre, tereftalsyre og hydrok-syftalsyre; og av di- eller triestrene av tre- eller fireverdige karboksylsyrer som hemimellittsyre, trimellittsyre, pyromellittsyre og sitronsyre.
Det foretrekkes kalsium-, magnesium- og sink-karboksylater av karboksylsyrer som har 7-18 karbonatomer (metallsåper i snever betydning), så som for eksempel benzoater eller alkanoater, fortrinnsvis stearat, oleat, laurat, palmetat, behenat, hydroksystearater, risinoleater, dihydroksystearater eller 2-etylheksanoat. Særlig foretrukket er stearat, oleat og p-tert-butylbenzoat. Overbasede karboksylater, så som overbaset sinkoktoat, er også foretrukket. Det foretrekkes likeledes overbasede kalsiumsåper.
Om ønsket, er det også mulig å benytte en blanding av karboksylater med forskjellige strukturer.
Det foretrekkes blandinger, som beskrevet, omfattende en organosink- og/eller organokalsium-forbindelse.
I tillegg til de nevnte forbindelser, er også organoaluminium-forbindelser egnet, likeså vel som forbindelser som er analoge med dem nevnt over, særlig aluminiumtristearat, aluminiumdistearat og aluminiummonostearat, og også aluminiuacetat og basiske derivater av disse.
Ytterligere informasjon angående aluminiumforbindelsene som kan anvendes og som er foretrukket, er gitt i US 4 060 512 og US 3 243 394.
I tillegg til de allerede nevnte forbindelser er det også egnet organiske forbindelser av sjeldne jordmetaller, særlig forbindelser som er analoge dem nevnt over. Betegnelsen forbindelse av sjeldent jordmetall betyr særlig forbindelser av grunnstoffene cerium, praseodymium, neodymium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, lutetium, lantanum og yttrium, idet blandinger, særlig med cerium, er foretrukket. Flere foretrukne forbindelser av sjeldne jordmetaller kan finnes i EP-A-0 108 023.
Om ønsket er det mulig å benytte en blanding av sink-, alkalimetall-, jordalkalimetall-, aluminium-, cerium-, lantan- eller lantanoid-forbindelser med ulik struktur. Det er også mulig å belegge en alumosalt-forbindelse med organosink-, organoaluminium-, organocerium-, organo-alkalimetall-, organo-jordalkalimetall-, organolantan- eller organolantanoid-forbindelser, i denne forbindelse se også DE-A-4 031 818.
Metallsåpene og/eller blandinger av disse, kan benyttes i en mengde for eksempel fra 0,001 til 10 vektdeler, hensiktsmessig fira 0,01 til 8 vektdeler og særlig foretrukket fra 0,05 til 5 vektdeler per 100 vektdeler PVC. det samme gjelder de ytterligere metallstabilisatorer: III. Ytterligere metallstabilisatorer: Her kan særlig nevnes organotinn-stabilisatorene. Spesielt kan disse være karboksylater, merkaptider og sulfider. Eksempler på egnede forbindelser er beskrevet i US 4 743 640. IV. Alkalimetall- og jordalkalimetall-forbindelser: Med disse menes prinsipielt karboksylatene av de ovenfor beskrevne syrer, men også korresponderende oksider og/eller hydroksider eller karbonater. Også egnet er blandinger av disse med organiske syrer. Eksempler er LiOH, NaOH, KOH, CaO, Ca(OH2), MgO, Mg(OH)2, Sr(OH)2, Al(OH)3, CaC03 og MgCo3 (også basiske karbonater så som magnesia alba og huntitt), og også Na- og K-salter av fettsyrer. I tilfelle jordalkalimetall og Zn-karboksylater, så er det også mulig å benytte adduktene av disse med MO eller M(OH)2(M = Ca, Mg, S eller Zn), kjent som "overbasede" forbindelser. I tillegg til stabilisatorkombinasjonen ifølge oppfinnelsen, foretrekkes det å benytte alkalimetallkarboksylater, jordalkalimetallkarbok-sylater og/eller alumuniumkarboksylater. V. Smøremidler: Eksempler på egnede smøremidler er montanvoks, fettsyreestere, PE-vokser, amidvokser, klorerte parafiner, glyserolestere eller jordalkalimetallsåper. Smøremidler som kan anvendes, er også beskrevet i "Kunststoffadditive", R. Gåchter/H. Muller, Carl Hanser Verlag, 3. utg., 1989, p. 478-488). Det kan også nevnes fettketoner (som beskrevet i DE 4 204 887) og silikon-baserte smøremidler (som beskrevet i EP 0 225 261), eller kombinasjoner av disse, som angitt i EP 0 259 783. Kalsiumstearat er foretrukket. Smøremidlene kan også anvendes sammen med en alumosalt-forbindelse, i denne forbindelse se også DE-A-4 031 818. VI. Mykgjørere: Eksempler på egnede organiske mykgjørere finnes i følgende grupper: A) Ftalater: Eksempler på slike mykgjørere er dimetyl-, dietyl-, dibutyl-, diheksyl-, di-2-etylheksyl-, di-n-oktyl-, diisooktyl-, diisononyl-, disiodecyl-, diisotridecyl-, disykloheksyl-, dimetylsykloheksyl-, dimetylglykol-, dibutylglykol-, benzylbutyl- og difenyl-ftalat, og også blandinger av ftalater, så som C7.9- og C9_n-alkylftalater fremstilt av overveiende lineære alkholer, Cé-io-n-alkylftalater og C8.i0-n-alkylftalater. Av disse foretrekkes dibutyl-, diheksyl-, di-2-etylheksyl-, di-n-oktyl-, diisooktyl-, disononyl-, diisodecyl-, diisotridecyl- og benzylbutyl-ftalat, og den angitte blanding av alkylftalater. Særlig foretrukket er di-2-etylheksyl-, diisononyl- og diisodecyl-ftalat, hvilke også er kjent under de vanlige forkortelser DOP (dioktylftalat, di-2-etylheksylftalat), DINP (diisononylftalat) og DIDP (diisodecylftalat). B) Estere av alifatiske dikarboksylsyrer, særlig estere av adipinsyre, acelainsyre og sebasinsyre: Eksempler på slike mykgjørere er di-2-etylheksyladipat, diisooktyladipat (blanding), diisononyladipat (blanding), diisodecyladipat (blanding), benzylbutyladipat, benzyloktyladipat, di-2-etylheksylacelat, di-2-etylheksylsebasat og diisododecylsebasat (blanding). Di-2-etylheksyladipat og diisooktyladipat er foretrukket. C) Trimellitater, eksempler er tri-2-etylheksyltrimellitat, triisodecyltrimellitat (blanding), triisotridecyltrimellitat, triisooktyltrimellitat (blanding), og også tri-C6.8-alkyl-, tri-C6-io-alkyl-, tri-C7.9-alkyl-, og tri-C9.n-alkyl-trimellitater. De sistnevnte trimellitater er dannet ved forestring av trimellitinsyre med de korresponderende alkanolblandinger. Foretrukne trimellitater er tri-2-etylheksyltrimellitat og de ovennevnte trimellitater av alkanolblandinger. Vanlige forkortelser er TOTM (trioktyltrimellitat, tri-2-etyl-heksyltrimellitat), TIDTM (triisodecyltrimellitat) og TITDTM (triisodecyltrimellitat). D) Epoksy-mykgjørere: Disse er først og fremst epoksiderte umettede fettsyrer, så som epoksidert soyabønneolje. E) Polymere mykgjørere: En definisjon av disse mykgjørere og eksempler på dem er gitt i "Kunststoffadditive", R. Gåchter/H. Muller, Carl Hanser Verlag, 3. utg. 1989, kap. 5.9.6, p. 412-415, og også i "PVC Technology", W. V. Titow, 4. utg., Elsevier Publ., 1984, p. 165-170. De vanligste startmaterialer ved fremstilling av polyester-mykgjørere er dikarboksylsyrer, så som adipinsyre, ftalsyre, acelainsyre og sebasinsyre; dioler, så som 1,2-propandiol, 1,3-butandiol, 1,4-butandiol, 1,6-heksandiol, neopentylglykol og dietylenglykol. F) Fosforsyreestere: En definisjon av disse estere er gitt i den ovennevnte "Taschenbuch der Kunststoffadditive" kap. 5.9.5, p. 408-412. Eksempler på slike fosforsyreestere er tributylfosfat, tri-2-etylbutylfosfat, tri-2-etylheksylfosfat, trikloretylfosfat, 2-etylheksyl-difenylfosfat, kresyldifenylfosfat, trifenylfosfat, trikresylfosfat og trixylenylfosfat. Det foretrekkes tri-2-etylheksylfosfat og ®Reofos 50 og 95 (Ciba Spezialitatenchemie).
G) Klorerte hydrokarboner (parafiner).
H) Hydrokarboner.
I) Monoestere, for eksempel butyloleat, fenoksyetyloleat, tetrahydrofurfuryloleat og alkylsulfonsyreestere.
J) Glykolestere, for eksempel diglykolbenzoater.
Definisjoner og eksempler på mykgjørere i grupper G)-J) er gitt i de følgende håndbøker: "Kunststoffadditive", R. Gåchter/H. Muller, Carl Hanser Verlag, 3.utg., 1989, kap. 5.9.14.2, p. 422-425, (gruppe G), og kap. 5.9.14.1, p. 422, (gruppe H).
"PVC Technology", W. V. Titow, 4. utg., Elsevier Publ., 1984, kap. 6.10.2, p. 171-173, (gruppe G), kap. 6.10.5, p. 174 (gruppe H), kap. 6.10.3, p. 173 (gruppe I) og kap. 6.10.4, p. 173-174 (gruppe J).
Det er også mulig å anvende blandinger av forskjellige mykgjørere. Mykgjørerne kan benyttes i en mengde for eksempel fra 5 til 20 vektdeler, hensiktsmessig fra 10 til 20 vektdeler per 100 vektdeler PVC. Stiv eller halvstiv PVC inneholder fortrinnsvis opp til 10 %, særlig foretrukket opp til 5 % mykgjører, eller ikke noe mykgjører.
VII. Pigmenter: Egnede stoffer er kjent for fagfolk på området. Eksempler på uorganiske pigmenter er TiC>2, zirkoniumoksid-baserte pigmenter, BaSC>4, sinkoksid (sinkhvitt) og litoponer (sinksulfid/bariumsulfat), sot, sot/titandioksid-blandinger, jern-oksidpigmenter, Sb203, (Ti,Ba,Sb)02, Cr203, spineller som koboltblått og koboltgrønt, Cd(S,Se), ultramarinblått. Organiske pigmenter er for eksempel azo-, ftalocyanin-, kinakridon-, perylen-, diketopyrolpyrol- og antrakinon-pigmenter. Det foretrekkes også
Ti02 i mikronisert form. En definisjon og ytterligere beskrivelse er gitt i "Handbook of PVC Formulating", E. J. Wickson, John Wiley & Sons, New York, 1993.
VIII. Fosfitter (fosforsyrling-triestere): Eksempler er trifenylfosfitt, difenylalkylfosfitter, fenyldialkylfosfitter, tris(nonylfenyl)fosfitt, triaurylfosfitt, trioktadecylfosfitt, distearylpentaeiytritoldifosfitt, tris(2,4-di-tert-butylfenyl)fosfitt, diisodecylpentaerytritoldifosfitt, bis-(2,4-di-tert-butylfenyl)pentaerytritoldifosfitt, bis-(2,6-di-tert-butyl-4-metylfenyl)pentaerytritoldifosfitt, bis-isodecyloksy-pentaery-tritoldifosfitt, bis-(2,4-di-teit-butyl-6-metylfenyl)pentaerytritoldifosfitt, bis-(2,4,6-tri-tert-butylfenyl)pentaerytritoldifosfitt, tristearylsorbitoltrifosfitt, bis-(2,4-di-tert-butyl-6-metylfenyl)metylfosfitt, bis-(2,4-di-tert-butyl-6-metylfenyl)etylfosfitt. Særlig egnet er trioktyl; tridecyl; tridodecyl; tritetradecyl; tristearyl; trioleyl; trifenyl; trikresyl; tris-p-nonylfenyl- eller trisykloheksyl-fosfitt og særlig foretrukket er aryldialkyl- og alkyldiaryl-fosfitter, med eksempler fenyldidecyl; 2,4-di-tert-butylfenyldidodecyl- og 2,6-di-tert-butylfenyldidodecyl-fosfitt, og dialkyl- diaryl-pentaerytirtoldifosfitter som disteaiylpentaerytritoldifosfitt, og også ikke-støkiometriske fosfitter for eksempel med sammensetning (H^CgQH^O^PCOCn.n^s^Vs eller (H8Ci7-C6H4)02P(i-C8H170) eller (H19C9-C6H4)01,5P(OC9,11H19)23)1,5 eller
Foretrukne organiske fosfitter er distearylpentaerytritol-difosfitt, trisnonylfenyl-fosfitt og fenyldidecyl-fosfitt. Andre egnede fosfitter er fosforsyrling-diestere (med de ovennevnte radikaler) og fosforsyrling-monoestere (med de ovennevnte radikaler), eventuelt i form av alkalimetall-, jordalkalimetall-, sink- eller aluminiumsaltene. Det er også mulig å anvende disse fosforsyrling-estere sammen med en alumosaltforbindelse, se også i denne forbindelse DE-A-4 031 818.
De organiske fosfitter kan benyttes i en mengde på for eksempel fra 0,01 til 10, hensiktsmessig fra 0,05 til 5, og særlig fra 0,1 til 3 vektdeler per 100 vektdeler PVC.
IX. Tiofosfitter og tiofosfater: Med tiofosfitter og tiofosfater menes forbindelser av den generelle type henholdsvis (RS)3P, (RS)3P=0 og (RS)3P=S, som beskrevet blant annet i patentskriftene DE 2 809 492, EP 0 090 770 og EP 0 573 394. Eksempler på disse forbindelser er tritioheksylfosfitt, tritiooktylfosfitt, tritiolaurylfosfitt, tritiobenzylfosfitt, tritiofosforsyrling-tris(karbo-i-oktyloksy)metylester, tritiofosforsyrling-tris(karbotrimetylsykloheksyloksy)metylester, tritiofosforsyre-S,S,S-tris(karbo-i-oktyloksy)metylester, tritiofosforsyre-S,S,S-tris(karbo-2-etylheksyloksy)metylester, tritiofosforsyre-S,S,S-tris-1 -(karboheksyloksy)etylester, tritiofosforsyre-S,S,S-tris-1 -
(karbo-2-etylheksyloksy)etylester og tritiofosforsyre-S,S,S-tris-2(karbo-2-etylheksyloksy)etylester.
X. Merkaptokarboksylsyreestere: Eksempler på disse forbindelser er estere av tioglykolsyre, tiomalinsyre, merkaptopropionsyre, merkaptobenzosyre og tiomelkesyre, merkaptoetylstearat og merkaptoetyloleat, som beskrevet i patentskriftene FR 2 459 816, EP 0 090 748, FR 2 552 440 og EP 0 365 483. De generiske merkaptokarboksylsyreestere innbefatter også polyolestere og partielle estere derav, og også tioetere dannet av disse.
XI. Epoksiderte fettsyreestere og andre epoksyforbindelser: Stabilisatorkombinasjonen ifølge oppfinnelsen kan i tillegg omfatte fortrinnsvis minst en epoksidert fettsyreester. Særlig egnede slike estere er estere av fettsyrer fra naturlige kilder (fettsyreglyserider), så som soyabønneolje eller rapsfrøolje. Det er imidlertid også mulig å benytte syntetiske produkter, så som epoksidert butyloleat. Epoksidert polybutadien og polyisopren kan også anvendes ettersom de er i hydroksilert form eller i delvis hydroksilert form, og ellers kan det anvendes homopolymert eller kopolymert glysidylakrylat og glysidylmetakrylat. Disse epoksyforbindelser kan også anvendes sammen med en alumosaltforbindelse, se også i denne forbindelse DE-A-4 031 818.
XII. Antioksidanter: Eksempler på slike egnede forbindelser er:
Alkylerte monofenoler, for eksempel, 2,6-di-tert-butyl-4-metylfenol, 2-tert-butyl-4,6-dimetylfenol, 2,6-di-tert-butyl-4-etylfenol, 2,6-di-tert-butyl-4-n-butylfenol, 2,6-di-tert-butyl-4-iso-butylfenol, 2,6-di-syklopentyl-4-metylfenol, 2-(a-metylsykloheksyl)-4,6-dimetylfenol, 2,6-di-okta-decyl-4-metylfenol, 2,4,6-trisykloheksylfenol, 2,6-di-tert-butyl-4-metoksy-metylfenol, 2,6-dinonyl-4-metylfenol, 2,4-dimetyl-6-(l '-metylundek-1 '-yl)fenol, 2,4-dimetyl-6-(l '-metylheptadek-1 '-yl)fenol, 2,4-dimetyl-6-(l '-metyltridek-l'-yl)fenol, oktylfenol, nonylfenol, dodecylfenol og blandinger derav.
Alkyltiometylfenoler, for eksempel, 2,4-dioktyltiometyl-6-tert-butyl-fenol, 2.4- dioktyltiometyl-6-metylfenol, 2,4-dioktyltiometyl-6-etyl-fenol, 2,6-didodecyltiometyl-4-nonylfenol.
Alkylerte hydrokinoner, for eksempel, 2,6-di-tert-butyl-4-metoksyfenol, 2.5- di-tert-butylhydrokinon, 2,5-di-tert-amylhydrokinon, 2,6-difenyl-4-oktadecyloksy-fenol, 2,6-di-tert-butylhydrokinon, 2,5-di-tert-butyl-4-hydroksyanisol, 3,5-di-tert-butyl-4-hydroksyanisol, 3,5-di-tert-butyl-4-hydroksyfenylstearat, bis-(3,5-di-tetr-butyl-4-hydroksyfenyl)adipat.
Hydroksylerte tiodifenyletere, for eksempel, 2,2'-tiobis-(6-tert-butyl-4-metylfenol), 2,2'-tiobis-(4-oktylfenol), 4,4'-tiobis-(6-tert-butyl-3-metyl-fenol), 4,4'-tiobis-(6-tert-butyl-2-metylfenol), 4,4'-tiobis-(3,6-di-sek-amylfenol), 4,4'-bis-(2,6-dimetyl-4-hydroksyfenyl)disulfid.
Alkylidenbisfenoler, for eksempel, 2,2'-metylenbis-(6-tert-butyl-4-metyl-fenol), 2,2'-metylenbis-(6-tert-butyl-4-etylfenol), 2,2'-metylen-bis[4-metyl-6-(a-metylsykloheksyl)fenol], 2,2'-metylenbis-(4-metyl-6-sykloheksylfenol), 2,2'-metylenbis-(6-nonyl-4-metylfenol), 2,2' -metylenbis-(4,6-di-tert-butylfenol), 2,2' -etylidenbis-(4,6-di-tert-butyl-fenol), 2,2' -etylidenbis-(6-tert-butyl-4-isobutylfenol), 2,2' -metylenbis[6-(a-metylbenzyl)-4-nonylfenol], 2,2'-metylenbis[6-(a,a-di-metylbenzyl)-4-nonylfenol], 4,4'-metylenbis-(2,6-di-tert-butylfenol), 4,4'-metylenbis-(6-tert-butyl-2-metylfenol), 1,1-bis-(5-tert-butyl-4-hydroksy-2-metylfenyl)butan, 2,6-bis-(3-tert-butyl-5-metyl-2-hydr-oksybenzyl)-4-metylfenol, 1,1,3-tris(5-tert-butyl-4-hydroksy-2-metyl-fenyl)butan, 1,1-bis-(5-tert-butyl-4-hydroksy-2-metylfenyl)-3-n-dodecylmerkaptobutan, etylenglykol bis [3,3 -bis-(3' -tert-butyl-4' -hydroksyfenyl)butyrat], bis-(3 -tert-butyl-4-hydroksy-5 - metyl-fenyl)disyklopentadien, bis[2-(3'-tert-butyl-2'-hydroksy-5'-metylbenzyl)-6-tert-butyl-4-metylfenyl]tereftalat, 1,1 -bis-(3,5-dimetyl-2-hydroksyfenyl)butan, 2,2-bis-(3,5-di-tert-butyl-4-hydroksyfenyl)propan, 2,2-bis-(4-hydroksy-fenyl)propan, 2,2-bis-(5-tert-butyl-4-hydroksy-2-metyl-fenyl)-4-n-dodecylmerkaptobutan, 1,1,5,5-tetra(5-tert-butyl-4-hydroksy-2-metylfenyl)pentan.
Benzylforbindelser, for eksempel, 3,5,3',5'-tetra-tert-butyl-4,4'-dihydroksy-dibenzyleter, oktadecyl 4-hydroksy-3,5-dimetylbenzyl-merkaptoacetat, tris-(3,5-di-tert-butyl-4-hydroksybenzyl)amin, bis-(4-tert-butyl-3-hydroksy-2,6-dimetylbenzyl)ditio-tereftalat, bis-(3,5-di-tert-butyl-4-hydroksybenzyl)sulfid, isooktyl, 3,5-di-tert-butyl-4-hydroksybenzyl-merkaptoacetat.
Hydroksybenzylerte malonater, for eksempel, dioktadecyl 2,2-bis-(3,5-di-tert-butyl-2-hydroksybenzyl)malonat, dioktadecyl 2-(3-tert-butyl-4-hydroksy-5-metyl-benzyl)malonat, didodecyl- merkaptoetyl-2,2-bis-(3,5-di-tert-butyl-4-hydroksybenz-yl)malonat, di[4-(l,l,3,3-tetrametylbutyl)-fenyl]2,2-bis-(3,5-di-tert-butyl-4-hydroksy-benzyl)malonat.
Aromatiske hydroksybenzylforbindelser, for eksempel, l,3,5-tris(3,5-di-tert-butyl-4-hydroksybenzyl)-2,4,6-trimetylbenzen, 1,4-bis-(3,5-di-tert-butyl-4-hydroksy-benzyl)-2,3,5,6-tetrametylbenzen, 2,4,6-tris(3,5-di-tert-butyl-4-hydroksybenzyl)fenol.
Triazinforbindelser, for eksempel, 2,4-bis-oktylmerkapto-6-(3,5-di-tert-butyl-4-hydroksyanilino)-1,3,5-triazin, 2-oktylmerkapto-4,6-bis-(3,5-di-tert-butyl-4-hydroksyanilino)-l,3,5-triazin, 2-oktylmerkapto-4,6-bis-(3,5-di-tert-butyl-4-hydroksyfen-oksy)-1,3,5-triazin, 2,4,6-tris(3,5-di-tert-butyl-4-hydroksyfenoksy)-1,2,3-triazin, 1,3,5-tris(3,5-di-tert-butyl-4-hydroksybenzyl)isocyanurat, 1,3,5-tris(4-tert-butyl-3-hydroksy-2,6-dimetylbenzyl)isocyanurat, 2,4,6-tris(3,5-di-tert-butyl-4-hydroksyfenyletyl)-l,3,5-triazin, l,3,5-tris(3,5-di-tert-butyl-4-hydroksyfenylpropionyl)heksahydro-l,3,5-tri^ l,3,5-tris-(3,5-disykloheksyl-4-hydroksybenzyl)isocyanurat.
Fosfonater og fosfonitter. for eksempel, dimetyl 2,5-di-tert-butyl-4-hydrokstbenzylfosfonat, dietyl 3,5-di-tert-butyl-4-hydroksy-benzyl-fosfonat, dioktadecyl 3,5-di-tert-butyl-4-hydroksybenzylfosfonat, dioktadecyl 5-tert-butyl-4-hydroksy-3-metylbenzylfosfonat, Ca-salt av monoetyl-3,5-di-tert-butyl-4-hydroksybenzylfosfonat, tetrakis(2,4-di-tert-butylfenyl)-4,4'-bifenylendifosfonit, 6-isooktyloksy-2,4,8,10-tetra-tert-butyl-12H-dibenz[d,g]-1,3,2-dioksafosfocin, 6-fluor-2,4,8,10-tetra-tert-butyl-12-metyl-dibenz[d,g]-1,3,2-dioksafosfosin.
Acylaminofenoler. for eksempel, 4-hydroksylauranilid, 4-hydroksy-stearanilid, oktyl N-(3,5-di-tert-butyl-4-hydroksyfenyl)karbamat.
Estere av P-( 3. 5- di- tert- butvl- 4- hvdroksvfenyl') propionsvre med en- eller flerbasiske alkoholer, for eksempel med metanol, etanol, oktanol, oktadekanol, 1,6-heksandiol, 1,9-nonandiol, etylenglykol, 1,2-propandiol, neopentylglykol, tiodi-etylenglykol, trietylenglykol, pentaerytritol, dipentaerytritol, tris(hydroksyetyl)isocyanurat, N,N'-bis-(hydroksyetyl)oksalamid, 3-tiaundekanol, 3-tiapentadekanol, trimetyl-heksandiol, trimetylolpropan, ditrimetylolpropan, 4-hydroksymetyl-l-fosfa-2,6,7-trioksabisyklo[2,2,2]oktan.
Estere av P-( 5- tert- butyl- 4- hvdroksy- 3- metylfenvl) propionsyre med en-eller flerbasiske alkoholer, for eksempel med metanol, etanol, oktanol, oktadekanol, 1,6-heksandiol, 1,9-nonandiol, etylenglykol, 1,2-propandiol, neopentylglykol, tio-dietylenglykol, trietylenglykol, pentaerytritol, tris(hydroksyetyl)isocyanurat, N,N'-bis-(hydroksyetyl)oksalamid, 3-tiaundekanol, 3-tiapentadekanol, trimetyl-heksandiol, trimetylolpropan, ditrimetylolpropan, 4-hydroksymetyl-1 -fosfa-2,6,7-trioksabisyklo-[2,2,2]oktan.
Estere av P-( 3. 5- disykloheksyl- 4- hydroksyfenyl) propionsvre med en- eller flerbasiske alkoholer, for eksempel med metanol, etanol, oktanol, oktadekanol, 1,6-heksandiol, 1,9-nonandiol, etylenglykol, 1,2-propandiol, neopentylglykol, tiodietyl-englykol, trietylenglykol, pentaerytritol, tris(hydroksyetyl)isocyanurat, N,N'-bis-(hydroksyetyl)oksalamid, 3-tiaundekanol, 3-tiapentadekanol, trimetyl-heksandiol, trimetylolpropan, ditrimetylolpropan, 4-hydroksymetyl-1 -fosfa-2,6,7-trioksabisyklo-[2,2,2]oktan.
Estere av 3, 5- di- tetr- butvl- 4- hydroksyfenyleddiksvre med en- eller flerbasiske alkoholer, for eksempel med metanol, etanol, oktanol, oktadekanol, 1,6-heksandiol, 1,9-nonandiol, etylenglykol, 1,2-propandiol, neopentylglykol, tiodi-etylenglykol, trietylenglykol, pentaerytritol, tris(hydroksyetyl)isocyanurat, N,N'-bis-(hydroksyetyl)oksalamid, 3-tiaundekanol, 3-tiapentadekanol, trimetyl-heksandiol, trimetylolpropan, ditrimetylolpropan, 4-hydroksymetyl-1 -fosfa-2,6,7-trioksabisyklo-[2,2,2]oktan.
Amider av P-(, 3, 5- di- tert- butvl- 4- hydroksyfenyl) propionsvre, så som for eksempel, N,N'-bis-(3,5-di-tert-butyl-4-hydroksyfenylpropionyl)heksametylendiamin, N,N' -bis-(3,5-di-tert-butyl-4-hydroksyfenylpropionyl)trimetylen-diam N,N' -bis-(3,5-di-tert-butyl-4-hydroksyfenylpropionyl)hydrasin.
Vitamin E (tokoferol) og derivater.
Det foretrekkes antioksidanter fra grupper 1-5, 10 og 12, særlig 2,2-bis-(4-hydroksyfenyl)propan, estere av 3,5-di-tert-butyl-4-hydroksyfenyl-propionsyre med oktanol, oktadekanol eller pentaerytritol eller tris(2,4-di-tert-butylfenyl)fosfitt.
Om ønskelig er det også mulig å benytte en blanding av antioksidanter med forskjellige strukturer.
Antioksidantene kan benyttes i en mengde for eksempel fra 0,01 til 10 vektdeler, hensiktsmessig fra 0,1 til 10 vektdeler, og særlig fra 0,1 til 5 vektdeler per 100 vektdeler
PVC.
XIII. UV-absorbere og lysstabilisatorer: Eksempler på disse er: 2-( 2' - hvdroksyfenyDbenzotirazoler. så som for eksempel 2-(2'-hydroksy-5 '-metylfenyl)benzotriazol, 2-(3',5 '-di-tert-butyl-2'-hydroksyfenyl)benzo-triazol, 2-(5'-tert-butyl-2' -hydroksyfenol)benzotriazol, 2-(2 '-hydroksy-5 '-(1,1,3,3-tetrametylbutyl)-fenyl)benzotriazol, 2-(3',5'-di-tert-butyl-2'-hydroksy-fenyl)-5-klorbenzotriazol, 2-(3'tert-butyl-2'-hydroksy-5'-metylfenyl)-5-klor-benzotriazol, 2-(3'-sek-butyl-5'-tert-butyl-2'-hydroksyfenyl)-benzotriazol, 2-(3' -sek-butyl-5' -tert-butyl-2' -hydroksyfenyl)-benzo-triazol, 2-(2'-hydroksy-4'-oktoksyfenyl)benzotriazol, 2-(3' ,5'-di-tert-amyl-2'-hydroksyfenyl)benzotriazol, 2-(3' ,5 '-bis-(a,a-dimetylbenzyl)-2' -hydroksyfenyl)benzotriazol, blandinger av 2-(3 '-tert-butyl-2-hydroksy-5 '-(2-oktyloksykarbonyletyl)fenyl)-5-klor-benzotriazol, 2-(3'-tert-butyl-5'-[2-(2-etylheksyloksy)karbonyletyl]-2'-hydroksyfenyl)-5-klorbenzotri-azol, 2-(3 '-tert-butyl-2'-hydroksy-5'-(2-metoksykarbonyletyl)fenyl)-5-klor-benzotriazol, 2-(3'-tetr-butyl-2'-hydroksy-5'-(2-metoksykarbonyletyl)fenyl)benzotriazol, 2-(3' -tert-butyl-2' -hydroksy-5 '-(2-oktyloksykarbonyletyl)fenyl)benzotriazol, 2-(3' -tert-butyl-5 ' - [2-(2-etylheksyloksy)karbonyletyl]-2' -hydroksyfenyl)benzotriazol, 2-(3' - dodecyl-2'-hydroksy-5'-metylfenyl)benzotriazol og 2-(3 '-tert-butyl-2'-hydroksy-5'-(2-isooktyloksykarbonyletyl)fenylbenzotriazol, 2,2'-metylen-bis[4-(l,l,3,3-tetrametyl-butyl)-6-benzotriazol-2-ylfenol]; transforestringsproduktet av 2-[3'-tert-butyl-5'-(2-metoksykarbonyletyl)-2'-hydroksyfenyl]benzotriazol med polyetylenglykol 300; hvor R = 3 '-tert-butyl-4'-hydroksy-5 '-2H-benzotriazol-2-yl-fenyl.
2- hvdroksybenzofenoner, for eksempel 4-hydroksy-, 4-metok-sy-, 4-oktoksy-, 4-decyloksy-, 4-dodecyloksy-, 4-benzyloksy-, 4,2',4'-tirhydroksy-, 2'-hydroksy-4,4'-dimetoksy-derivatet.
Estere av substituerte eller usubstituerte benzosyrer, for eksempel 4-tert-butylfenylsalisylat, fenylsalisylat, oktylfenylsalisylat, dibenzoylresorsinol, bis-(4-tert-butylbenzoyl)resorsinol, benzoylresorsinol, 2-4-di-tert-butylfenyl 3,5-di-tert-butyl-4-hyd-roksybenzoat, heksadecyl 3,5-di-tetr-butyl-4-hydroksybenzoat, oktadecyl-3,5-di-tert-butyl-4-hydroksybenzoat, 2-metyl-4,6-di-tert-butylfenyl-3,5-di-tert-butyl-4-hydroksy-benzoat.
Akrylater. for eksempel etyl-a-cyano-P,P-difenylakrylat eller isooktyl-etyl-a-cyano-P,p-difenylakrylat, metyl-a-karbo-metoksycinnamat, metyl-a-cyano-P-metyl-p-metoksycinnamat eller butyl-a-cyano-P-metyl-p-metoksycinnamat, metyl-a-karbo-metoksy-p-metoksycinnamat, N-(P-karbometoksy-b-cyanovinyl)-2-metyl-indolin.
Nikkelforbindelser, for eksempel nikkelkomplekser av 2,2'-tiobis[4-(l,l,3,3-tetrametylbutyl)fenol], så som 1:1- eller 1:2-komplekset med eller uten ytterligere ligander som n-butylamin, trietanolamin eller N-sykloheksyldietanolamin, nikkeldibutylditiokarbamat, nikkelsalter av monoalkylestere som metyl- eller etylesteren av 4-hydroksy-3,5-di-tert-butylbenzylfosfonsyre, nikkelkomplekser av ketoksimer, så som av 2-hydroksy-4-metylfenyl undecylketoksim, nikkelkomplekser av l-fenyl-4-lauroyl-5-hydroksypyrasol, med eller uten ytterligere ligander.
Oksalamider. for eksempel 4,4'-dioktyloksyanilid, 2,2'-dioktyloksy-5,5'-di-tert-butyl-oksanilid, 2,2'-didodecyloksy-5,5'-di-tert-butyloksanilid, 2-etoksy-2'-etyl-oksanilid, N,N'-bis-(3-dimetylaminopropyl)oksalamid, 2-etoksy-5-tert-butyl-2'-etyl-oksanilid og dens blanding med 2-etoksy-2'-etyl-5,4'-di-tert-butyl-oksanilid, blandinger av o- og p-metoksy- og av o- og p-etoksy-di-substituerte oksanilider.
2-( 2- hvdroksyfenvlVl , 3, 5- triaziner. for eksempel 2,4,6-tris(2-hydroksy-4-oktyloksyfenyl)-1,3,5-triazin, 2-(2-hydroksy-4-oktyloksyfenyl)-4,6-bis-(2,4-dimetyl-fenyl)-1,3,5-triazin, 2-(2,4-dihydroksyfenyl)-4,6-bis-(2,4-dimetyl-fenyl)-1,3,5-triazin, 2,4-bis-(2-hydroksy-4-propyloksyfenyl)-6-(2,4-dimetyl-fenyl)-l,3,5-triazin, 2-(2-hydroksy-4-oktyloksyfenyl)-4,6-bis-(4-metylfenyl)-1,3,5-triazin, 2-(2-hydroksy-4-dodecyl-oksyfenyl)-4,6-bis-(2,4-dimetylfenyl)-1,3,5-triazin, 2-[2-hydroksy-3-butyloksypropylok-sy)fenyl]-4,6-bis-(2,4-dimetylfenyl)-l,3,5-triazin, 2-[2-hydroksy-4-(2-hydroksy-3-oktyl-oksypropyloksy)fenyl]-4,6-bis-(2,4-dimetylfenyl)-1,3,5-triazin.
Sterisk hindrede aminer, for eksempel bis-(2,2,6,6-tetrametyl-piperidin-4-yl)sebasat, bis-(2,2,6,6-tetrametylpiperidin-4-yl)suksinat, bis-( 1,2,2,6,6-pentametyl-piperidin-4-yl)sebasat, bis-( 1 -oktyloksy-2,2,6,6-tetrametyl-piperidin-4-yl)sebasat, bis-(l,2,2,6,6-pentametylpiperidyl)n-butyl-3,5-di-tert-butyl-4-hydroksybenzylmalonat, kondensatet av l-hydroksyetyl-2,2,6,6-tetrametyl-4-hydroksypiperidn og ravsyre, lineære eller sykliske kondensater av N,N'-bis-(2,2,6,6-tetrametyl-4-piperidyl)heksametylen-diamin og 4-tert-oktylamino-2,6-diklor-l,3,5-s-triazin, tris(2,2,6,6-tetrametyl-4-piperi-dyl) nitrilotriacetat, 1,1 '-(l,2-etandiyl)-bis-(3,3,5,5-tetrametylpiperazinon),4-benzoyl-2,2,6,6-tetrametylpiperidin, 4-stearyloksy-2,2,6,6-tetrametylpiperidin, bis-(l ,2,2,6,6-pentametylpiperidyl)2-n-butyl-2-(2-hydroksy-3,5-di-tert-butylbenzyl)malonat, 3-n-oktyl-7,7,9,9-tetrametyl-l,3,8-triasaspirl[4.5]dekan-2,4-dion, bis-(l-oktyloksy-2,2,6,6-tetra-metylpiperidyl)sebasat, bis-( 1 -oktyloksy-2,2,6,6-tetrametylpiperidyl)suksinat, lineært eller sykliske kondensater av N,N'-bis-(2,2,6,6-tetrametyl-4-piperidyl)heksa-metylendiamin og 4-morfolino-2,6-diklor-l,3,5-triazin, kondensatene av 2-klor-4,6-di-(4-n-butylamino-2,2,6,6-tetrametylpiperidyl)-1,3,5-triazin og 1,2-bis-(3-aminopropyl-amino)etan, kondensatene av 2-klor-4,6-di(4-n-butylamino-l,2,2,6,6-pentametyl-piperidyl)-l,3,5-triazin og l,2-bis-(3-aminopropyl-amino)etan, 8-acetyl-3-dodecyl-7,7,9,9-tetrametyl-l,3,8-triasa-spiro[4.5]dekan-2,4-dion, 3-dodecyl-l-(2,2,6,6-tetrametyl-4-piperidyl)pyrrolidin-2,5-dion, 3-dodecyl-1 -(1,2,2,6,6-pentametyl-4-piperidyl)pyrro-lidin-2,5-dion, blandinger av 4-heksadecyloksy- og 4-stearyloksy-2,2,6,6-tetrametyl-piperidin, kondensatet av N,N'-bis-(2,2,6,6-tetrametyl-4-piperidyl)heksametylendiamin og 4-sykloheksylamino-2,6-diklor-l,3,5-triazin, kondensatet av l,2-bis-(3-aminopropylamino)etan og 2,4,6-triklor-l,3,5-triazin, og også 4-butylamino-2,2,6,6-tetrametylpiperidin (CAS reg. nr. [136504-96-6]); N-(2,2,6,6-tetrametyl-4-piperidyl)-n-dodecylsuksinimid, N-(l ,2,2,6,6-pentametyl-4-piperidyl)-n-dodecyl-suksinimid, 2-undecyl-7,7,9,9-tetrametyl-l-oksa-3,8-diasa-4-oksospiro[4.5]dekan, omsetningsproduktet av 7,7,9,9-tetrametyl-2-sykloundecyl-l-oksa-3,8-diasa-4-oksospiro[4.5]dekan og epiklorhydrin, 1,1 -bis-( 1,2,2,6,6-pentametyl-4-piperidyloksykarbonyl)-2-(4-metoksyfenyl)etan, N,N'-bis-formyl-N,N'-bis-(2,2,6,6-tetrametyl-4-piperidyl)heksametylendiamin, diesteren av 4-metoksymetylenmalonsyre med l,2,2,6,6-pentametyl-4-hydroksypiperidin, poly-[metylpropyl-3-oksy-4—(2,2,6,6-tetrametyl-4-pipeirdyl)]-siloksan, omsetningsproduktet av maleinsyre anhydrid-a-olefinkopolymer og 2,2,6,6-tetrametyl-4-aminopiperidin eller l,2,2,6,6-pentametyl-4-aminopiperidin.
XIV. Esemidler: Eksempler på esemidler er organiske azo- og hydrazo-forbindelser, tetrazoler, oksaziner, isatoinsyreanhydrid og også natriumkarbonat og natriumbikarbonat. Det foretrekkes azodikarboksamid og natriumbikarbonat, og blandinger derav. Definisjoner og eksempler på slagfast modifiserende midler og bearbeidingshjelpemidler, gelingsmidler, antistatika, biosider, metallpassivatorer, optiske klaringsmidler, flammehemmende midler, antidugg-midler og kompatibilisatorer, er beskrevet i "Kunststoffaddivite", R. Gåchter/H. Maller, Carl Hanser Verlag, 3. utg., 1989, og i "Handbook of Polyvinyl Chloride Formulating" E. J. Wickson, J. Wiley & Sons, 1993, og i "Plastics Additives" G. Pritchard, Chapman & Hall, London, 1. utg., 1998. Slagfastmodifiserende midler er også detaljert beskrevet i "Impact Modifiers for PVC", J. T. Lutz/D. L. Dunkelberger, John Wiley & Sons, 1992.
XV. P-Diketoner, P-ketoestere: 1,3-dikarbonylforbindelser som kan anvendes, kan være lineære eller sykliske dikarbonylforbindelser. Det foretrekkes å anvende dikarbonylforbindelser med følgende formel: R',CO CHR'2-COR'3 hvor R'i er Ci_22-alkyl, Cs.io-hydroksyalkyl, C2.i8-alkenyl, fenyl, OH-, Ci^-alkyl-, Ci^-alkoksy- eller halogen-substituert fenyl, C7.i0-fenylalkyl, C5.i2-sykloalkyl, CM-alkyl-substituert C5.i2-sykloalkyl eller en gruppe -R'5-S-R'6 eller R'5-0-R'6, R'2 er hydrogen, Ci_8-alkyl, C2-12-alkenyl, fenyl, C7.i2-alkylfenyl, C7.io-fenylalkyl eller en gruppe -CO-R'4, R'3 er som angitt for R'! eller er Cu8-alkoksy, R'4 er Cj^-alkyl eller fenyl, R'5 er Q.io-alkylen og R'6 er Ci.i2-alkyl, fenyl, C7-ig-alkylfenyl eller C7.i0-<f>enylalkyl.
Disse innbefatter de hydroksylholdige diketoner i EP 0 346 279 og oksa- og tia-diketonene i EP 0 307 358, samt ketoestrene basert på isocyansyre i US 4 339 383.
R'i og R'3 som alkyl kan særlig være Ci.i8-alkyl, så som for eksempel metyl, etyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, heksyl, heptyl, oktyl, decyl, dodecyl eller oktandecyl.
R'i og R'3 som hydroksyalkyl er særlig en gruppe -(CH^n-OH hvor n er 5, 6 eller 7.
R'i og R'3 som alkenyl kan for eksempel være vinyl, allyl, metallyl, 1-butenyl, 1-heksenyl eller oleyl, fortrinnsvis allyl.
R'i og R'3 som OH-, alkyl-, alkoksy- eller halogen-substituert fenyl kan for eksempel være tolyl, xylyl, tert-butylfenyl, metoksyfenyl, etoksyfenyl, hydroksyfenyl, klorfenyl eller diklorfenyl.
R'i og R'3 som fenylalkyl er særlig benzyl, R'2 og R'3 som sykloalkyl eller alkylsykloalkyl er særlig sykloheksyl eller metylsykloheksyl, R'2 som alkyl kan særlig være Ci^-alkyl, R'2 som C2.i2-alkenyl kan særlig være allyl.
R'2 som alkylfenyl kan særlig vare tolyl. R'2 som fenylalkyl kan særlig vare benzyl. Fortrinnsvis er R'2 hydrogen. R'3 som alkoksy kan for eksempel være metoksy, etoksy, butoksy, heksyloksy, oktyloksy, dodecyloksy, tridecyloksy, tetradecyloksy eller oktadecyloksy. R'5 som Q.io-alkylen er særlig, C2-4-alkylen. R'6 som alkyl er særlig C4. 12-alkyl, så som for eksempel butyl, heksyl, oktyl, decyl eller dodecyl. R'6 som alkylfenyl er særlig tolyl. R'6 som fenylalkyl er særlig benzyl.
Eksempler på 1,3-dikarbonylforbindelser med formelen over og deres alkalimetall-, jordalkalimetall-, sink- og aluminiumgelater er acetylaceton, butanoylaceton, heptan-oylaceton, steroylaceton, palmitoylaceton, lauroylaceton, 7-tert-nonyltio-2,4-heptandion, benzoylaceton, dibenzoylmetan, lauroylbenzoylmetan, palmitoylbenzoylmetan, stearoyl-benzoylmetan, isooktylbenzoylmetan, 5-hydroksykapronyl-benzoylmetan, tribenz-oylmetan, bis-(4-metylbenzoyl)metan, benzoyl-p-klorbenzoylmetan, bis-(2-hydroksyben-zoyl)metan, 4-metoksybenzoyl,benzoylmetan, bis-(4-metoksybenzoyl)metan, 1-benzoyl-1-acetylnonan, benzoylacetylfenylmetan, stearoyl-4-metoksybenzoylmetan, bis-(4-tert-butylbenzoyl)metan, benzoylformylmetan, benzoylfenylacetylmetan, bis-sykloheks-anoylmetan, di-pivaloylmetan, 2-acetylsyklopentanon, 2-benzosyklopentanon, metyl-, etyl-, og allyl-diacetoacetat, metyl- og etylbenzoyl-, propionyl- og butyrylacetoacetat, triacetylmetan, metyl-, etyl-, heksyl-, oktyl-, dodecyl- eller oktadecyl-acetoacetat, metyl-, etyl-, butyl-, 2-etylheksyl-, dodecyl- eller oktadecyl-benzoylacetat, og også Ci.ig-alkyl-propionylacetater og butyrylacetater; etyl-, propyl-, butyl-, heksyl- eller oktyl-stearoyl-acetat, og også polysykliske P-ketoestere som beskrevet i EP 0 433 230 og dehydraeddiksyre, og aluminium-, sink-, alkalimetall- og jordalkalimetall-saltene derav. Det foretrekkes 1,3-diketoforbindelser med formelen over hvor R\ er Q.ig-alkyl, fenyl, OH-, metyl- eller metoksy-substituert fenyl, Cy.io-fenylalkyl eller sykloheksyl, R'2 er hydrogen og R'3 er som definert for R'!.
1,3-diketoforbindelsene kan benyttes i en mengde for eksempel 0,01 til 10, hensiktsmessig fra 0,01 til 3, og særlig fra 0,01 til 2 vektdeler per 100 vektdeler PVC.
Eksempler på klorholdige polymerer som må stabiliseres er: polymerer av vinylklorid og av vinylidenklorid, vinylpolymerer som har vinylkloridenheter i strukturen, så som kopolymerer av vinylklorid, og vinylestere av alifatiske syrer, særlig vinylacetat, kopolymerer av vinylklorid med estere av akrylsyre og metakrylsyre og med akrylonitril, kopolymerer av vinylklorid med dienforbindelser og umettede dikarboksylsyrer eller deres anhydrider, så som kopolymerer av vinylklorid med dietylmaleat, dietylfumarat eller maleinsyreanhydrid, etterklorerte polymerer og kopolymerer av vinylklorid, kopolymerer av vinylklorid og vinylidenklorid med umettede aldehyder, ketoner og andre forbindelser som akreloin, krotonaldehyd, vinylmetylketon, vinylmetyleter, vinylisobutyleter og lignende; polymerer av vinylidenklorid og kopolymerer av vinylidenklorid med vinylklorid og andre polymeriserbare forbindelser; polymerer av vinylkloracetat og diklordivenyleter; klorerte polymerer av vinylacetat, klorerte polymere estere av akrylsyre og av a-substituert akrylsyre; polymerer av klorerte styrener, for eksempel diklorstyren; klorerte gummier; klorerte polymerer av etylen; polymerer og etterklorerte polymerer av klorbutadien og kopolymerer derav med vinylklorid, klorerte naturlige og syntetiske gummier, og også blandinger av disse polymerer med hverandre eller med andre polymeriserbare forbindelser. Når det gjelder denne oppfinnelse, så omfatter PVC også kopolymerer med polymeriserbare forbindelser som akrylnitril, vinylacetat eller ABS, som kan være suspensjon-, masse- eller emulsjonspolymerer. Preferanse gis til en PVC-homopolymer, alene eller i kombinasjon med polyakrylater. Også innbefattet er podepolymerer av PVC med EVA, ABS og MBS. Foretrukne substrater er også blandinger av de ovennevnte homo- og kopolymerer, særlig vinylklorid-homopolymerer med andre termoplastiske og/eller elastomere polymerer, særlig blandinger med ABS, MBS, NBR, SAN, EVA, CPE, MB AS, PMA, PMMA, EPDM og polylaktoner.
Eksempler på slike komponenter er materialer av (i) 20-80 vektdeler vinylklorid-homopolymer (PVC) og (ii) 80-20 vektdeler av minst en termoplastisk kopolymer basert på styren og akrylnitril, særlig fra gruppene ABS, NBR, NAR, SAN og EVA. Forkor-telsene anvendt for kopolymerene er velkjente for fagfolk på området og har følgende betydninger: ABS: akrylnitril-butadien-styren, SAN: styren-akrylnitril, NBR: akrylnitril-butadien, NAR: akrylnitril-akrylat, EVA: etylen-vinylacetat. Særlig egnet er også akrylat-baserte styren-akrylnitril-kopolymerer (ASA). Foretrukne komponenter i denne sammenheng er polymermaterialer omfattende som komponenter (i) og (ii) en blanding av 25-75 vekt% PVC og 75-25 vekt% av de ovennevnte kopolymerer. Eksempler på slike materialer er: 25-50 vekt% PVC og 75-50 vekt% kopolymerer, eller 40-75 vekt% PVC og 60-25 vekt% kopolymerer. Foretrukne kopolymerer er ABS, SAN og modifisert EVA, særlig ABS. NBR, NAR og EVA er også særlig egnet. En eller flere av den ovennevnte kopolymerer kan være til stede i materialet ifølge oppfinnelsen. Særlig viktige komponenter er materialer omfattende (i) 100 vektdeler PVC og (ii) 0-300 vektdeler ABS og/eller SAN-modifisert ABS, og 0-80 vektdeler av kopolymerene NBR, NAR og/eller EVA, men særlig EVA.
Med hensyn til stabilisering innen rammen for denne oppfinnelse, er ytterligere egnede polymerer særlig resirkulerte klorholdige polymerer. Disse polymerer er polymerene nærmere beskrevet over og som også er påført skade under bearbeiding, bruk eller lagring. Resirkulert PVC er særlig foretrukket. Resirkulerte materialer kan inneholde små mengder fremmedstoffer, så som for eksempel papir, pigmenter og adhesiver, som ofte er vanskelige å fjerne. Disse fremmedstoffer kan komme fra kontakt med forskjellige materialer under bruk eller resirkulering, eksempler er rester av drivstoff, fraksjoner av beleggingsmateriale, spor av metaller og initiatorrester.
Stabilisering ifølge oppfinnelsen er særlig fordelaktig for PVC-formuleringer som er vanlige for rør og profiler. Stabilisering kan skje uten tungmetallforbindelser (Sn-, Pb-, Cd-og Zn-stabilisatorer). Dette trekk medfører fordeler på visse områder fordi tungmetaller - med unntak av sink i beste fall - ofte er uønskede både under produksjon og under bruk av visse PVC-artikler, av økologiske årsaker. Produksjonen av tung-metallstabilisatorer medfører også ofte problemer når det gjelder industriell hygiene. Likeledes er bearbeiding av malm som inneholder tungmetaller ofte forbundet med alvorlige innvirkninger på miljøet. Miljøet innbefatter her biosystemet for mennesker, dyr (fisk), planter, luft og jord. Av disse årsaker er det også betenkelig med forbrenning av, og landfyllinger med, plast som inneholder tungmetaller.
Stabilisatorene kan hensiktsmessig bli innlemmet gjennom følgende metoder: Som en emulsjon eller dispersjon (en mulighet er for eksempel i form av en pastalignende blanding, og med hensyn til dette er det en fordel at forbindelsene ifølge oppfinnelsen gir en stabil pasta); som tørrblanding ved innblanding av ytterligere komponenter eller polymerblandinger; som direkte tilsetning i bearbeidingsapparaturen (for eksempel kalandere, blandere, kompoundere, ekstrudere og lignende), eller i form av en løsning eller en smelte, eller som flak eller granulater i støvfri form som et énkomponent-produkt.
PVC stabilisert i henhold til oppfinnelsen kan fremstilles på i og for seg kjent måte ved å anvende i og for seg kjente innretninger, slik som den ovennevnte bearbeidingsapparatur, for å blande stabilisatoren ifølge oppfinnelsen og eventuelt ytterligere additiver med PVC. I dette tilfellet kan stabilisatorene tilsettes hver for seg, som en blanding eller i form av såkalte konsentratblandinger.
PVC stabilisert i henhold til den foreliggende oppfinnelse, kan bringes over i ønsket form ved å benytte kjente metoder. Eksempler på slike metoder er maling, kalandrering, eks-trudering, sprøytestøping eller spinning, og også ekstruderingsformblåsing. Stabilisert PVC kan også bearbeides til skummaterialer.
PVC stabilisert i henhold til oppfinnelsen er for eksempel egnet for hule gjenstander (flasker), forpakningsfilmer (folier for termoforming), blåste filmer, rør, skummaterialer, tunge profiler (vindusrammer), transparente veggprofiler, bygningsprofiler, veggplater, rørkoplinger, kontorfilmer og apparaturhus (datamaskiner, husholdningsmaskiner).
Det foretrekkes gjenstander av stivt PVC-skum og PVC-rør for drikkevann eller avløpsvann, trykkrør, gassrør, kabelledningsrør og kabelbeskyttelsesrør, rør for industrielle rørledninger, utløpsrør, avrenningsrør, nedløpsrør og dreneringsrør. For ytterligere detaljer angående dette, se "Kunststoffhandbuch PVC", Vol. 2/2, W. Becker/H. Braun, 2.utg., 1985, Carl Hanser Verlag, p. 1236-1277.
6-aminouraciler er fremstilt ved kjente fremgangsmåter [for eksempel US patent nr. 2 598 936, WO 96/04280, J.Org.Chem. 16, 1879-1890 (1951), J.Org.Chem. 30, 656
(1965), JACS 82, 3973(1960) og Synthesis 1996, p. 459, ff].
Fremstilte forbindelser 1 til 25 er oppsummert i tabell 1.
Som i det gjenværende av teksten, er deler og prosentandeler basert på vekt så sant annet ikke er angitt.
Eksempel 4
I en 1 14-halset kolbe med KPG-rører, luftkjøler, termometer og bobleteller ble det under nitrogen fylt 155,2 g (1,0 mol) 6-amino-l,3-dimetyluracil, 160 g (1,1 mol) 2-aminofenol-hydrogenklorid og 300 g dietylenglykoldimetyleter, og denne startsats ble omrørt ved 145-155 °C i 75 minutter. Deretter fikk reaksjonsblandingen avkjøle til 10 °C, de utfelte krystaller ble filtrert fra på et sugefilter, og filterproduktet ble vasket to ganger med 100 ml i-propanol hver gang. Krystallene ble tørket i et vakuumtørkekabinett ved 80 °C. Denne tørkede rest på 244,1 g ble deretter omrørt med 300 g vann i 30 minutter, og reaksjonsproduktet ble filtrert fra med suging, vasket med 100 g vann og tørket.
Utbytte: 188,6 g («76,3% av teoretisk) hvitt, krystallinsk pulver (smp. 228-230 °C).
Eksempel 13
En blanding av 43,5 g (0,357 mol) p-anisidin, 27,3 g (0,176 mol) 6-amino-l,3-dimetyluracil og 20 g av en 32% sterk saltsyre ble oppvarmet til 150 °C under omrøring i løpet av 1,5 timer. Under oppvarmingsfasen destillerte vannet av. Reaksjonsblandingen ble omrørt ved 150 °C i ytterligere 1,5 timer, og deretter avkjølt til 90 °C, 100 ml metanol ble tilsatt og blandingen oppvarmet under tilbakeløp i 30 minutter og deretter avkjølt til 5 °C. Den krystallinske utfelling ble filtrert fra med suging og deretter rekrystallisert fra en blanding av 200 ml n-propanol/60 ml vann.
Utbytte: 18,3 g («40% av teoretisk) hvite krystaller (smp. 167-168 °C).
Eksempel 18
26,2 g (0,15 mol) 6-klor-l,3-dimetyluracil, 20 g etanolamin og 50 ml vann ble varmet ved 20 °C under omrøring i 3 timer. Etter avkjøling til romtemperatur ble de utfelte krystaller filtrert fra med suging, vasket med THF og deretter tørket. Dette ga et utbytte av råprodukt på 28,8 g lysebrune krystaller. For ytterligere rensing ble disse brunaktige krystaller oppvarmet sammen med en løsning av 100 ml metanol/n-propanol (1:1) og 1 g natriumhydroksid, den grumsete bestanddel ble fjernet ved filtrering, filtratet ble avkjølt og utfelte hvite krystaller ble filtrert fra med suging og tørket.
Utbytte: 22,4 g («75% av teoretisk) hvite krystaller (smp. 179-181 °C).
Statisk varmetest
Hver av blandingene i henhold til de følgende tabeller med forklaringer, ble mykgjort på et sett blandevalser i 5 minutter ved 180 °C eller 190 °C. Prøvestrimler ble kuttet ut fra de resulterende filmer (tykkelse 0,3 mm), og disse strimler ble underkastet termisk spenning ved 190 °C i en "Mathis Thermo-Takter" i den tidsperiode som er angitt i tabellen nedenfor. Deretter ble gulhetsindeksen (Yl) bestemt i henhold til ASTM-1925-70.
Jo lavere Yl er, jo mer effektiv er stabilisatorsystemet.
Eksempel I
Resultatene er vist i tabell 2 nedenfor. Lave Yl-verdier betegner god stabilisering.
Eksempel II
Resultatene er vist i tabell 3 nedenfor. Lave Yl-verdier betegner god stabilisering.
Eksemplene viser tydelig at forbindelsene ifølge oppfinnelsen gir resultater, ikke bare når
det gjelder fargen til å begynne med og bibehold av farge (gjennomsnittlig farge), men også når det gjelder langtidsstabilitet - YI-måling -, som er forbedret i forhold til kjent teknikk.
Claims (18)
1. Forbindelse, karakterisert ved at den har generell formel I
hvor Y er oksygen, og Ri og R2 er uavhengig av hverandre Q.ig-alkyl, og R3 er Ci.ig-alkyl substituert med -OH, C5.8-sykloalkyl, eller mono-, di- eller
tri-OH-, -d^-alkyl-, -CM-alkoksy-, -C=0(OR4)- og/eller-0-COR4-substituert fenyl eller naftyl eller benzyl, hvor R4 er C\.\2-alkyl.
2. Forbindelse ifølge krav 1, karakterisert ved at
R3 er-OH-substituert Ci.]2-alkyl, sykloheksyl, allyl eller Cy.g-fenylalkyl.
3. Forbindelse ifølge krav 1, karakterisert ved at
Ri og R2 er Ci_4-alkyl, og
R3 er -OH-substituert Ci_4-alkyl, benzyl, fenyl, eller fenyl som er substituert med -OH og 1 til 3 ganger med Ci_4-alkyl.
4. Materiale, karakterisert ved at det omfatter en klorholdig polymer og minst én forbindelse med generell formel I ifølge krav 1.
5. Materiale ifølge krav 4, karakterisert ved at det omfatter minst en epoksidert fettsyreester.
6. Materiale ifølge krav 4, karakterisert ved at det omfatter minst ett sinkkarboksylat og/eller alkalimetallkarboksylat og/eller jordalkalimetallkarboksylat og/eller aluminiumkarboksylat.
7. Materiale ifølge krav 4, karakterisert ved at det omfatter minst et ytterligere stoff valgt blant fosfitter, antioksydanter, P-dikarbonylforbindelser, mykgjørere, fyllstoffer, smøremidler og pigmenter.
8. Materiale ifølge krav 4, karakterisert ved at det omfatter fyllstoff i form av kritt.
9. Materiale ifølge krav 4, karakterisert ved at det omfatter smøremiddel i form av kalsiumstearat.
10. Materiale ifølge krav 4, karakterisert ved at det omfatter pigment i form av titandioksid og/eller zirkoniumoksid og/eller bariumsulfat.
11. Materiale ifølge krav 4, karakterisert ved at det omfatter minst en polyol og/eller en disakkaridalkohol.
12. Materiale ifølge krav 4, karakterisert ved at det omfatter minst en glysidylforbindelse.
13. Materiale ifølge krav 4, karakterisert ved at det omfatter minst en perkloratforbindelse.
14. Materiale ifølge krav 4, karakterisert ved at det omfatter minst en zeolittforbindelse.
15. Materiale ifølge krav 4, karakterisert ved at det omfatter minst en lagoppbygd gitterforbindelse (hydrotalsitter).
16. Materiale ifølge krav 4, karakterisert ved at det omfatter minst ett hydrotalcitt.
17. Anvendelse av en forbindelse med generell formel hvor Y er oksygen, og Ri og R2 er uavhengig av hverandre Ci.i8-alkyl, og R3 er Ci.ig-alkyl substituert med -OH, C5.g-sykloalkyl, eller mono-, di- eller
tri-OH-, -Ci_4-alkyl-, -CM-alkoksy-, -C=0(OR4)- og/eller-0-COR4-substituert fenyl eller naftyl eller benzyl, hvor R4 er Ci.i2-alkyl. som stabilisator for halogenholdige polymerer.
18. Anvendelse ifølge krav 17, hvor de halogenholdige polymerer er resirkulerte halogenholdige polymerer.
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MY114466A (en) * | 1996-09-25 | 2002-10-31 | Crompton Vinyl Additives Gmbh | Rigid pvc stabilised with n, n-dimethyl-6-aminouracils |
-
1999
- 1999-03-17 AT AT99105458T patent/ATE230733T1/de active
- 1999-03-17 DK DK99105458T patent/DK0967209T3/da active
- 1999-03-17 DE DE59903953T patent/DE59903953D1/de not_active Expired - Lifetime
- 1999-03-17 ES ES99105458T patent/ES2189300T3/es not_active Expired - Lifetime
- 1999-03-17 EP EP99105458A patent/EP0967209B1/de not_active Expired - Lifetime
- 1999-04-22 CA CA002269747A patent/CA2269747A1/en not_active Abandoned
- 1999-06-18 US US09/336,079 patent/US6174941B1/en not_active Expired - Fee Related
- 1999-06-24 JP JP11178647A patent/JP2000026433A/ja active Pending
- 1999-06-25 NO NO19993181A patent/NO313412B1/no unknown
Also Published As
Publication number | Publication date |
---|---|
DK0967209T3 (da) | 2003-03-24 |
US6174941B1 (en) | 2001-01-16 |
ES2189300T3 (es) | 2003-07-01 |
NO993181L (no) | 1999-12-27 |
JP2000026433A (ja) | 2000-01-25 |
NO993181D0 (no) | 1999-06-25 |
ATE230733T1 (de) | 2003-01-15 |
DE59903953D1 (de) | 2003-02-13 |
EP0967209A1 (de) | 1999-12-29 |
CA2269747A1 (en) | 1999-12-26 |
EP0967209B1 (de) | 2003-01-08 |
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