NO312895B1 - 5-substituerte 6-aminouraciler som stabilisatorer for halogenholdige polymerer, materialer omfattende slike forbindelserog anvendelse av slike forbindelser - Google Patents
5-substituerte 6-aminouraciler som stabilisatorer for halogenholdige polymerer, materialer omfattende slike forbindelserog anvendelse av slike forbindelser Download PDFInfo
- Publication number
- NO312895B1 NO312895B1 NO19993183A NO993183A NO312895B1 NO 312895 B1 NO312895 B1 NO 312895B1 NO 19993183 A NO19993183 A NO 19993183A NO 993183 A NO993183 A NO 993183A NO 312895 B1 NO312895 B1 NO 312895B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- substituted
- phenyl
- acid
- tert
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 69
- 229920000642 polymer Polymers 0.000 title claims abstract description 35
- 229910052736 halogen Inorganic materials 0.000 title claims abstract description 8
- 150000002367 halogens Chemical class 0.000 title claims abstract description 8
- 239000000463 material Substances 0.000 title claims description 26
- 239000003381 stabilizer Substances 0.000 title claims description 24
- -1 phenylcarbamoyl Chemical group 0.000 claims abstract description 119
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 239000000460 chlorine Substances 0.000 claims abstract description 24
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 13
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 230000000087 stabilizing effect Effects 0.000 claims abstract description 6
- 239000010457 zeolite Substances 0.000 claims description 56
- 229910021536 Zeolite Inorganic materials 0.000 claims description 40
- 239000011701 zinc Substances 0.000 claims description 20
- 229910052725 zinc Inorganic materials 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 239000004014 plasticizer Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 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
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000000049 pigment Substances 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- 239000003963 antioxidant agent Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000000945 filler Substances 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- 125000004169 (C1-C6) 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
- 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 3
- 229910001701 hydrotalcite Inorganic materials 0.000 claims description 3
- 229960001545 hydrotalcite Drugs 0.000 claims description 3
- 235000013539 calcium stearate Nutrition 0.000 claims description 2
- 239000008116 calcium stearate Substances 0.000 claims description 2
- 239000004408 titanium dioxide Substances 0.000 claims description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 4
- 150000002016 disaccharides Chemical class 0.000 claims 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims 1
- 229910001928 zirconium oxide Inorganic materials 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 48
- 125000003545 alkoxy group Chemical group 0.000 abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 6
- 230000006641 stabilisation Effects 0.000 abstract description 6
- 238000011105 stabilization Methods 0.000 abstract description 6
- 125000003884 phenylalkyl group Chemical group 0.000 abstract description 5
- 125000001624 naphthyl group Chemical group 0.000 abstract description 2
- 239000004800 polyvinyl chloride Substances 0.000 abstract description 2
- 229920000915 polyvinyl chloride Polymers 0.000 abstract description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical class O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 39
- 150000002148 esters Chemical class 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- 229920001577 copolymer Polymers 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- 229910052751 metal Inorganic materials 0.000 description 16
- 239000002184 metal Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 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 13
- 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
- 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
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 11
- 239000004593 Epoxy Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 10
- 239000000344 soap Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 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
- 239000007788 liquid Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 229910052700 potassium Inorganic materials 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
- 239000005038 ethylene vinyl acetate Substances 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 8
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
- 229910052788 barium Inorganic materials 0.000 description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 150000002170 ethers Chemical class 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
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-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
- 229960000583 acetic acid Drugs 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 150000001342 alkaline earth metals Chemical class 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-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
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 235000013772 propylene glycol Nutrition 0.000 description 6
- 229960004063 propylene glycol Drugs 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229910052712 strontium 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
- VFGRNTYELNYSKJ-UHFFFAOYSA-N 6-amino-1,3-dimethylpyrimidine-2,4-dione Chemical compound CN1C(N)=CC(=O)N(C)C1=O VFGRNTYELNYSKJ-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
- 239000007983 Tris buffer Substances 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
- 229910052681 coesite Inorganic materials 0.000 description 5
- 229910052906 cristobalite Inorganic materials 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 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
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 235000012239 silicon dioxide Nutrition 0.000 description 5
- 229910052682 stishovite Inorganic materials 0.000 description 5
- 229920000638 styrene acrylonitrile Polymers 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 229910052905 tridymite Inorganic materials 0.000 description 5
- 125000005591 trimellitate group Chemical group 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
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-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
- 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
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000004494 ethyl ester group Chemical group 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
- 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 4
- 229920001519 homopolymer Polymers 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
- 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
- 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
- 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
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920000647 polyepoxide Polymers 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
- 150000003254 radicals Chemical class 0.000 description 4
- 229910052761 rare earth metal Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000000600 sorbitol Substances 0.000 description 4
- 235000010356 sorbitol Nutrition 0.000 description 4
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
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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
- 150000003751 zinc Chemical class 0.000 description 1
- 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
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- 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
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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
-
- 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
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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
- C07D239/557—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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 with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. orotic acid
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3462—Six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Oppfinnelsen angår 6-aminouraciler, substituert i posisjon 5, med formel I gjengitt nedenfor, klorholdige polymermaterialer med slike aminouraciler som har formel II gjengitt nedenfor, og en fremgangsmåte for å stabilisere klorholdige polymerer. Disse aminouraciler kan anvendes som stabilisator for halogenholdige 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; 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 beskrevet i US 3 436 362, US 4 656 209, US 4 352 903 og EP-A-0 768 336, og de kan fremstilles ved kjente metoder i ett (eller flere) prosesstrinn.
Det er nå funnet at 5-substituerte 6-aminouraciler er særlig egnet for stabilisering av klorholdige polymerer, så som f.eks. PVC.
Med oppfinnelsen tilveiebringes således en forbindelse med generell formel I
hvor
Y er oksygen eller svovel,
Ri og R2 er, uavhengig av hverandre, Ci.ig-alkyl, C3.6-alkenyl eller C5.8-sykloalkyl, som eventuelt er substituert med CM-alkoksy, Cs.g-sykloalkyl, -OH og/eller Cl; C7.9-fenylalkyl hvor eventuelt fenylringen er substituert med CM-alkyl, Ci_4-alkoksy, C5_g-sykloalkyl, -OH og/eller Cl; eller fenyl,
R3 er H; Q.ig-alkyl som eventuelt er substituert med -OH; eller fenyl som eventuelt er substituert med -OH, og
R5 er H, Ci_i2-alkyl eller fenyl som eventuelt er substituert med -OH, Ci.4-alkyl, CM-alkoksy, -0=0(0^) og/eller-O-CORe, og
R<5 er rettkjedet eller forgrenet Ci.i2-alkyl, eller rettkjedet eller forgrenet C2_i2-alkenyl.
Oppfinnelsen angår også et materiale omfattende en klorholdig polymer og minst én forbindelse med generell formel II
hvor
n er 1 eller 2,
Y er oksygen eller svovel,
Ri og R2 er uavhengig av hverandre Ci.i8-alkyl, C3.6-alkenyl, C5.8-sykloalkyl som er usubstituert eller substituert med Ci_4-alkoksy, Cs.g-sykloalkyl, -OH og/eller Cl; C7.9-fenylalkyl som er usubstituert eller fenylringen er substituert med CM-alkyl, Ci_4-alkoksy, C5.g-sykloalkyl, -OH og/eller Cl; eller fenyl,
R3 er H, Ci.ig-alkyl som er usubstituert eller substituert med -OH; eller fenyl som usubstituert eller substituert med -OH, og
R4 er -CC=0)-CM2-alkyl, -C(=0)-0-CM2-alkyl, -(C=O)-C0-i2-alkylen-(C=O)OZ,
hvor Zer H eller Ci.6-alkyl, -(C=0)-fenyl, eller
og når
n er 2,
R4 er gruppen -CHR5, hvor
R5 er H, Ci.^-alkyl eller fenyl som er usubstituert eller substituert med -OH, Q.4-alkyl-, C].4-alkoksy, -C=0(OR6) og/eller -O-CORé, hvor R$ er rettkjedet eller forgrenet Ci_i2-alkyl, eller rettkjedet eller forgrenet C2-i2-alkenyl.
Videre angår oppfinnelsen en fremgangsmåte for å stabilisere klorholdige polymerer ved at det i polymerene innarbeides minst en forbindelse som har formel II angitt over.
En forbindelse med generell formel II angitt over er egnet for anvendelse som stabilisator for halogenholdige polymerer og resirkulerte materialer med slike.
For forbindelser med formel I og II vil
Ci_4-alkyl være for eksempel metyl, etyl, n-propyl, isopropyl, n-, i-, sek- eller t-butyl, C5_i8-alkyl være for eksempel pentyl, heksyl, heptyl, oktyl, 2-etylheksyl, i-oktyl, decyl, nonyl, undecyl, dodecyl, pentadecyl eller heksadecyl.
C3_6-alkenyl kan være allyl, 1-butenyl, 2-butenyl, 3-butenyl, isobutenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-heksenyl, 2-heksenyl, 3-heksenyl, 4-heksenyl, 5-heksenyl eller deres isomerer.
Ci_4-alkoksy kan være for eksempel metoksy, etoksy, n-propoksy eller n-butoksy, men også isopropoksy, isobutoksy eller tert-butoksy.
C5_8-sykloalkyl kan være for eksempel syklopentyl, sykloheksyl, sykloheptyl eller syklooktyl, fortrinnsvis sykloheksyl.
C7_]0-fenylalkyl kan være for eksempel benzyl, 1- eller 2-fenyletyl, 3-fenylpropyl, a,cc-dimetylbenzyl eller 2-fenylisopropyl, fortrinnsvis benzyl eller 2-fenetyl, særlig benzyl. Dersom det aromatiske radikal er substituert, så er det fortrinnsvis substituert med tre, to eller særlig én substituent, og substituentene er spesielt hydroksyl, klor, metyl, etyl, tert-butyl, metoksy eller etoksy. Særlig foretrukket er hydroksyl, metoksy og tert-butyl. Co-12-alkylen er enten en direkte binding eller for eksempel metylen, etylen, propylen, butylen, oktylen eller dodecenylen, og alle mulige isomerer av disse.
Det foretrekkes forbindelser med formel I hvor Y er oksygen og hvor n er 1 eller 2.
Det foretrekkes også forbindelser med generell formel I hvor Y er oksygen og Ri og R2 er uavhengig av hverandre Ci.g-alkyl, allyl eller C7_9-fenylalkyl, og R3, R5 og R$ er som definert over for formel I.
For å oppnå stabilisering av den klorholdige polymer, må forbindelsene med formel I eller II anvendes i en hensiktsmessig mengde fra 0,01 til 10 vekt%, f.eks. fra 0,05 til 5 vekt%, og særlig fra 0,1 til 3 vekt%.
Det er også mulig å benytte forbindelser med generell formel I eller II i kombinasjon med vanlige additiver og stabilisatorer, f.eks. sammen med polyoler og disakkaridalkoholer og/eller perkloratforbindelser og/eller glysidylforbindelser og/eller zeolittforbindelser og/eller lagoppbygde gitterforbindelser (hydrotalsitter), og også f.eks. 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 på f.eks. 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, f.eks. 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 glyserol-monotioetere. Ytterligere utførelsesformer er beskrevet i EP 0 394 547,
EP 0 457 471 og WO 94/24200.
Perkloratene kan benyttes i en mengde f.eks. 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 R! og R3 hydrogen og R2 er hydrogen eller metyl, og n er 0, eller R! 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 (5-metylglysidylestere kan fremstilles ved å omsette én forbindelse som har minst en karboksylgruppe i molekylet, med epiklorhydrin, glyseroldiklorhydrin eller P-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 f.eks. sykloheksankarboksylsyre, tetrahydroftalsyre, 4-metyltetrahydroftalsyre, heksahydroftalsyre eller 4-metylheksahydroftalsyre. Aromatiske karboksylsyrer kan også anvendes, f.eks. benzoinsyre, ftalinsyre, isofltalinsyre, trimellitinsyre og pyromellitinsyre. Det er likeledes mulig å gjøre bruk av karboksyl-terminerte addukter av f.eks. 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 P-metylglysidyletere som kan fremstilles 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^ter dannet f.eks. av asykliske alkoholer, så som etylenglykol, dietylenglykol og høyere poly(oksyetylen)glykoler, propan- 1,2-diol eller poly(oksy-propylen)glykoler, propan-1,3-diol, butan-1,4-diol, poly(oksytetrametylen)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 polyepiklorhydriner, butanol, amyl-alkohol, pentanol, og av monofunksjonelle alkoholer som isooktanol, 2-etylheksanol, isodekanol og også C7.9-alkanol og C9.n-alkanol-blandinger. De er imidlertid også dannet av f.eks. sykloalifatiske alkoholer som 1,3- eller 1,4-dihydroksysykloheksan, bis-(4-hyd-roksysykloheksyl)metan, 2,2-bis-(4-hydroksysykloheksyl)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 f.eks. fenol, resorsinol eller hydrokinon, eller de kan være basert på polynukleære fenoler, som f.eks. på bis-(4-hydroksyfenyl)-metan, 2,2-bis-(4-hydroksyfenyl)propan, 2,2-bis-(3,5-dibrom-4-hydroksyfenyl)propan, på 4,4'-dihydroksydifenylsulfon 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-epoksypropyl-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 f.eks. anilin, N-metylanilin, toluiden, n-butylamin, bis-(4-aminofenyl)-metan, m-xylylendiamin eller bis-(4-metylaminofenyl)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 f.eks. etan-1,2-ditiol eller bis-(4-merkaptometylfenyl)eter.
V) Epoksyforbindelser som har et radikal med formelen over hvor K\ og R3 sammen er -CH2-CH2- og n er 0, er bis-(2,3-epoksysyklopentyl)eter, 2,3-epoksysyklopentylglysi-dyleter eller l,2-bis-(2,3-epoksysyklopentyloksy)etan. Et epoksyharpiks som har et radikal med formel I hvor Rj og R3 sammen er -CH2-CH2- og n er 1, er f.eks. (3'4'-epoksy-6' -metylsykloheksyl)metyl-3,4-epoksy-6-metylsykloheksankarboksylat.
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-hydroksyfenyl)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, f.eks. 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 bl.a. fra patentene
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
M2+1.xM3+x(OH)2(Ab-U.dH20
hvor
M. = ett eller flere metaller valgt blant Mg, Ca, Sr, Zn og Sn,
M<3+> = Al eller B,
A" er et anion med valens n,
b er ettall fra 1-2,
0<x<0,5,
m er et tall fra 0 til 20.
Fortrinnsvis er
An = OH", C1CV, HCCV, CH3COO<->, C6H5COO", CO3<2>", (CHOHCOO)2<2->, (CH2COO)2<2>", CH3CHOHCOO", HP03<-> eller HP04<2>";
Eksempler på hydrotalsitter er
Al203.6MgO.C02.12H20 (i), Mg4>5Al2(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^KAlOzUSiQzJyJ.wHzO
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
Na12Al12Sii2048.27H20 [zeolitt A], Na6Al6Si6024.2 NaX.7,5H20, X=OH, halogen, CI04 [sodalitt]; Na6Al6Si3o072.24H20; Na8Al8Si4o096.24H20; Nai6Al16Si24O80.16H2O; Na16Al16Si32096.16H20; Na56Al56Si136O384.250H2O [zeolitt Y], Na86Al86Si106O384.264H2O [zeolitt X]; eller zeolittene som kan fremstilles ved hel eller delvis bytting av Na-atomene med Li-, K-, Mg-, Ca-, Sr- eller Zn-atomer, så som (Na,K)10Al10Si22O64.20H2O; Ca4,5Na3[(AlO2)12(SiO2)12].30H2O;K9Na3[(AlO2)12(SiO2)12].27H2O.
Foretrukne zeolitter er slike med formlene
Na12Al12Sii2048.27H20 [zeolitt A],
Na6Al6Si6024.2NaX.7,5H20, X = OH, Cl, C104, l/2C03[sodalitt]
Na6Al6Si30O72.24H2O,
Na8Al8Si40O96.24H2O,
Na16Al16Si24O80.16H2O,
Na16Al16Si32096.16H20,
Na56Al56Si136O384.250H2O [zeolitt Y],
Na86Al86Siio60384.264H20 [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 bytting av Na-atomene med Li-, K-, Mg-, Ca-, Sr-, Ba- eller Zn-atomer, så som (Na,K)i0Ali0Si22O64.20H2O; 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 zeolitter som er egnet 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 bytting av Na-atomene med Li-, K-, eller H-atomer, så som
(Li^K^oAljoSi^CW 20H2O.
K9Na3[(A102)12(Si02)i2]. 27H20
^AUSiA^HzOtzeolitt K-F]
Na8Al8Si4o096.24H20 [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, Na3oAl3oSi660]92. 98H20 [zeolitt ZX-5, zeolitt Q]
Særlig foretrukket ef 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 P^ 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 f.eks. 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 i materialene ifølge oppfinnelsen, så som stabilisatorer, hjelpestoffer og bearbeidingshjelpemidler, hvor eksempler er alkalimetall-forbindelser 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 f.eks. kalsiumkar-bonat, dolomitt, wollastonitt, magnesiumoksid, magnesiumhydroksid, 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, f.eks. 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 benzen-karboksylater 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.
Eksempler som kan nevnes er sink-, kalsium-, magnesium- eller barium-salter av énverdige 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-l,7-dikar-boksylsyre, oktan-1,8-dikarboksylsyre, ftalsyre, isoftalsyre, tereftalsyre og hydroksy-ftalsyre; og av di- eller triestrene av tre- eller fireverdige karboksylsyrer som hemimellitt-syre, trimellittsyre, pyromellittsyre og sitronsyre.
Det foretrekkes kalsium-, magnesium- og sink-karboksylater av karboksylsyrer som har 7-18 karbonatomer (metallsåper i snever betydning), så som f.eks. benzoater eller alkanoater, fortrinnsvis stearat, oleat, laurat, palmetat, behenat, hydroksystearater, risin-oleater, 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 organo-kalsium-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 også organiske forbindelser av sjeldne jordmetaller egnet, 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-, organo-cerium-, organo-alkalimetall-, organo-jordalkalimétall-, organolantan- eller organo-lantanoid-forbindelser, i denne forbindelse se også DE-A-4 031 818.
Metallsåpene og/eller blandinger av disse, kan benyttes i en mengde f.eks. fra 0,001 til 10 vektdeler, hensiktsmessig fra 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:
A) Ftalater: Eksempler på slike mykgjørere er dimetyl-, dietyl-, dibutyl-, diheksyl-, di-2-etylheksyl-, di-n-oktyl-, diisooktyl-, diisononyl-, disiodesyl-, diisotridesyl-, disyklo-heksyl-, 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, C6-io-n-alkylftalater og C8.io-n-alkylftalater. Av disse foretrekkes dibutyl-, diheksyl-, di-2-etylheksyl-, di-n-oktyl-, diisooktyl-, disononyl-, diisodesyl-, diisotridesyl- og benzylbutyl-ftalat, og den angitte blanding av alkylftalater. Særlig foretrukket er di-2-etylheksyl-, diisononyl- og diisodesyl-ftalat, hvilke også er kjent under de vanlige forkortelser DOP (dioktylftalat, di-2-etylheksylfitalat), DINP (diisononylftalat) og DIDP (diisodesylftalat). B) Estere av alifatiske dikarboksylsyrer, særlig estere av adipinsyre, acelainsyre og sebasinsyre: Eksempler på slike mykgjørere er di-2-etylheksyladipat, diisooktyladipat (blanding), diisononyladipat (blanding), diisodesyladipat (blanding), benzylbutyladipat, benzyloktyladipat, di-2-etylheksylacelat, di-2-etylheksylsebasat og diisododesylsebasat (blanding). Di-2-etylheksyladipat og diisooktyladipat er foretrukket. C) Trimellitater, eksempler er tri-2-etylheksyltrimellitat, triisodesyltrimellitat (blanding), triisotridesyltrimellitat, triisooktyltrimellitat (blanding), og også tri-C6.g-alkyl-, tri-C6-io-alkyl-, tri-C7_9-alkyl-,'og tri-C9.ii-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 (triisodesyltrimellitat) og TITDTM (triisodesyltrimellitat). 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. Maller, 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, fitalsyre, acelainsyre og sebasinsyre; dioler, så som 1,2-propandiol, 1,3-butandiol, 1,4-butandiol, 1,6-heksandiol, neopentylglykol ogdietylen-glykol. 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-etylheksyldi-fenylfosfat, 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, f.eks. butyloleat, fenoksyetyloleat, tetrahydrofurfuryloleat og alkylsulfon-syreestere.
J) Glykolestere, f.eks. 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 f.eks. 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 Ti02, zirkoniumoksid-baserte pigmenter, BaSC»4, sinkoksid (sinkhvitt) og litoponer (sinksulfid/bariumsulfat), sot, sot/titandioksid-blandinger, jernoksidpigmenter, Sb203, (Ti,Ba,Sb)02, Cr203, spineller som koboltblått og koboltgrønt, Cd(S,Se), ultra-marinblått. Organiske pigmenter er f.eks. 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, difenylalkyl-fosfitter, fenyldialkylfosfitter, tris(nonylfenyl)fosfitt, triaurylfosfitt, trioktadesylfosfitt, distearylpentaerytritoldifosfitt, tris(2,4-di-tert-butylfenyl)fosfitt, diisodesylpentaery-tritoldifosfitt, bis-(2,4-di-tert-butylfenyl)pentaerytritoldifosfitt, bis-(2,6-di-tert-butyl-4-metylfenyl)pentaerytritoldifosfitt, bis-isodesyloksy-pentaerytritoldifosfitt, bis-(2,4-di-tert-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; tridesyl; tridodesyl; tritetradesyl; tristearyl; trioleyl; trifenyl; trikresyl; tris-p-nonylfenyl- eller trisykloheksyl-fosfitt og særlig foretrukket er aryldialkyl- og alkyldiaryl-fosfitter, med eksempler fenyldidesyl; 2,4-di-tert-butylfenyldidodesyl- og 2,6-di-tert-butylfenyldidodesyl-fosfitt, og dialkyl- diaryl-pentaerytritoldifosfitter som distearylpentaerytritoldifosfitt, og også ikke-støkiometriske fosfitter f.eks. med sammensetning (Hi9C9C6H4)Oi)5P(OCi2ii3H25;27)li5 eller (H8C17-C6H4)02P(i-C8H170) eller (H19C9-C6H4)01,5P(OC9,iiH19>23)1;5 eller
Foretrukne organiske fosfitter er distearylpentaerytritol-difosfitt, trisnonylfenyl-fosfitt og fenyldidesyl-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 f.eks. 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, tritiofosforeyrling-tris(karbotri-metylsykloheksyloksy)metylester, tritiofosforsyre-S,S,S-tris(karbo-i-oktyloksy)metyl-ester, 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 tio-glykolsyre, 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 soyabørmeolje eller rapsfrøolje. Det er imidlertid også mulig å benytte syntetiske produkter, så som epoksidert butyloleat. Epoksidert polybuta-dien og polyisopren kan også anvendes ettersom de er i hydroksilert form eller i delvis hydroksilert form, og ellers kan det anvendes homopolymert eller kopolymert glysidyl-akrylat 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, f.eks., 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-desyl-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 '-metyltirdek-1 '-yl)fenol, oktylfenol, nonylfenol, dodesylfenol og blandinger derav.
Alkyltiometylfenoler, f.eks., 2,4-dioktyltiometyl-6-tert-butyl-fenol, 2,4-dioktyltiometyl-6-metylfenol, 2,4-dioktyltiometyl-6-etyl-fenol, 2,6-didodesyltiometyl-4-nonylfenol.
Alkylerte hydrokinoner, f.eks., 2,6-di-tert-butyl-4-metoksyfenol, 2,5-di-tert-butylhydrokinon, 2,5-di-tert-amylhydrokinon, 2,6-difenyl-4-oktadesyloksyfenol, 2,6-di-tert-butylhydrokinon, 2,5-di-tert-butyl-4-hydroksyanisol, 3,5-di-tert-butyl-4-hydroksy-anisol, 3,5-di-tetr-butyl-4-hydroksyfenylstearat, bis-(3,5-di-tert-butyl-4-hydroksyfenyl)-adipat.
Hydroksylerte tiodifenyletere, f.eks., 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, f.eks., 2,2'-metylenbis-(6-tert-butyl-4-metylfenol), 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), l,l-bis-(5-tert-butyl-4-hydroksy-2-metylfenyl)butan, 2,6-bis-(3-tert-butyl-5-metyl-2-hydroksyben2yl)-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-dodesylmerkaptobutan, etylenglykol bis[3,3-bis-(3 '-tert-butyl-4'-hydroksyfenyl)butyrat], bis-(3-tert-butyl-4-hydroksy-5-metyl-fenyl)disyklo-pentadien, bis[2-(3'-tert-butyl-2'-hydroksy-5'-m tereftalat, l,l-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-dodesylmerkaptobutan, 1,1,5,5-tetra(5-tert-butyl-4-hydroksy-2-metyl-fenyl)pentan.
Benzylforbindelser, f.eks., 3,5,3',5'-tetra-tert-butyl-4,4'-dihydroksy-di-benzyleter, oktadesyl 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, f.eks., dioktadesyl 2,2-bis-(3,5-di-tert-butyl-2-hydroksybenzyl)malonat, dioktadesyl 2-(3 -tert-butyl-4-hydroksy- 5 -metylbenzyl)-malonat, didodesyl- merkaptoetyl-2,2-bis-(3,5-di-tert-butyl-4-hydroksybenzyl)malonat, di[4-(l, 1,3,3-tetrametylbutyl)-fenyl]2,2-bis-(3,5-di-tert-butyl-4-hydroksybenzyl)malonat.
Aromatiske hydroksybenzylforbindelser, f.eks., l,3,5-tris(3,5-di-tert-butyl-4-hydroksybenzyl)-2,4,6-trimetylbenzen, l,4-bis-(3,5-di-tert-butyl-4-hydroksybenzyl)-2,3,5,6-tetrametylbenzen, 2,4,6-tris(3,5-di-tert-butyl-4-hydroksybenzyl)fenol.
Triazinforbindelser, f.eks., 2,4-bis-oktylmerkapto-6-(3,5-di-tert-butyl-4-hydroksyanilmo)-1,3,5-triazin, 2-oktylmerkapto-4,6-bis-(3,5-di-tert-butyl-4-hydroksy-anilino)-l,3,5-triazin, 2-oktylmerkapto-4,6-bis-(3,5-di-tert-butyl-4-hydroksyfenoksy)-1,3,5-triazin, 2,4,6-tris(3,5-di-tert-butyl-4-hydroksyfenoksy)-l,2,3-triazin, l,3,5-tris(3,5-di-tert-butyl-4-hydroksybenzyl)isocyanurat, l,3,5-tris(4-tert-butyl-3-hydroksy-2,6-di-metylbenzyl)isocyanurat, 2,4,6-tris(3,5-di-tert-butyl-4-hyd^oksyfenyletyl)-l,3,5-triazin, l,3,5-1ris(3,5-di-tert-butyl-4-hydroksyfenylpropi^^ 1,3,5-tris-(3,5-disykloheksyl-4-hydroksybenzyl)isocyanurat.
Fosfonater og fosfonitter, f.eks., dimetyl 2,5-di-tert-butyl-4-hydrokstbenzyl-fosfonat, dietyl 3,5-di-tert-butyl-4-hydroksy-benzyl-fosfonat, dioktadesyl 3,5-di-tert-butyl-4-hydroksybenzylfosfonat, dioktadesyl 5-tert-butyl-4-hydroksy-3-metylbenzyl-fosfonat, 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-tetr-butyl-12H-dibenz[d,g]-1,3,2-dioksafosfocin, 6-fluor-2,4,8,1O-tetra-tert-butyl- 12-metyl-dibenz[d,g]-1,3,2-dioksafosfosin.
Acylaminofenoler, f.eks., 4-hydroksylauranilid, 4-hydroksystearanilid, oktyl N-(3,5-di-tert-butyl-4-hydroksyfenyl)karbamat.
Estere av P-(3,5-di-tert-butyl-4-hydroksyfenyl)propionsyre med en- eller flerbasiske alkoholer, f.eks. med metanol, etanol, oktanol, oktadekanol, 1,6-heksandiol, 1,9-nonandiol, etylenglykol, 1,2-propandiol, neopentylglykol, tiodietylenglykol, trietylenglykol, pentaerytritol, dipentaerytritol, 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-(5-tert-butyl-4-hydroksy-3-metylfenyl)propionsyre med en-eller flerbasiske alkoholer, f.eks. med metanol, etanol, oktanol, oktadekanol, 1,6-heksandiol, 1,9-nonandiol, etylenglykol, 1,2-propandiol, neopentylglykol, tiodietylenglykol, trietylenglykol, pentaerytritol, tris(hydroksyetyl)isocyanurat, N,N'-bis-(hydroksy-etyl)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)propionsyre med en- eller flerbasiske alkoholer, f.eks. med metanol, etanol, oktanol, oktadekanol, 1,6-heksandiol, 1,9-nonandiol, etylenglykol, 1,2-propandiol, neopentylglykol, tiodietylenglykol, 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-tert-butyl-4-hydroksyfenyleddiksyre med en- eller fiere-basiske alkoholer, f.eks. med metanol, etanol, oktanol, oktadekanol, 1,6-heksandiol, 1,9-nonandiol, etylenglykol, 1,2-propandiol, neopentylglykol, tiodietylenglykol, 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-butyl-4-hydroksyfenyl)propionsyre, så som f.eks., N,N' -bis-(3,5-di-tert-butyl-4-hydroksy fenylpropionyl)heksametylendiamin, N,N' -bis-(3,5-di-tert-butyl-4-hydroksyfenylpropionyl)tirmetylen-diamin, 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 f.eks. 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'-hydroksyfenyl)benzotirazoler, så som f.eks. 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' -tert-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'-dodesyl-2'-hydroksy-5'-metylfenyl)benzotriazol og 2-(3'-tert-butyl-2'-hydroksy-5'-(2-iso-oktyloksykarbonyletyl)fenylbenzotriazol, 2,2'-metylen-bis[4-(l,l,3,3-tetrametylbutyl)-6-benzotriazol-2-ylfenol]; transforestirngsproduktet av 2-[3'-tert-butyl-5'-(2-metoksykar-bonyletyl)-2'-hydroksyfenyl]benzotriazol med polyetylenglykol 300; hvor R = 3'-tert-butyl-4' -hydroksy- 5' -2H-benzotriazol-2-yl-fenyl.
2-hydroksybenzofenoner, f.eks. 4-hydroksy-, 4-metok-sy-, 4-oktoksy-, 4-desyloksy-, 4-dodesyloksy-, 4-benzyloksy-, 4,2',4'-tirhydroksy-, 2'-hydroksy-4,4'-dimetoksy-derivatet.
Estere av substituerte eller usubstituerte benzosyrer, f.eks. 4-tert-butylfenyl-salisylat, fenylsalisylat, oktylfenylsalisylat, dibenzoylresorsinol, bis-(4-tert-butylbenzoyl)-resorsinol, benzoylresorsinol, 2-4-di-tert-butylfenyl 3,5-di-tert-butyl-4-hydroksybenzoat, heksadesyl 3,5-di-tert-butyl-4-hydroksybenzoat, oktadesyl-3,5-di-tert-butyl-4-hydroksy-benzoat, 2-metyl-4,6-di-tert-butylfenyl-3,5-di-tert-butyl-4-hydroksy-benzoat.
Akrylater, f.eks. 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, f.eks. nikkelkomplekser av 2,2'-tiobis[4-(l, 1,3,3-tetrametylbutyl)fenol], så som 1:1- eller 1:2-komplekset med eller uten ytterligere ligander som n-butylamin, trietanolamin eller N-sykloheksyldietanolamin, nikkeldibutyl-ditiokarbamat, nikkelsaker av monoalkylestere som metyl- eller etylesteren av 4-hydroksy-3,5-di-tert-butylbenzylfosfonsyre, nikkelkomplekser av ketoksimer, så som av 2-hydroksy-4-metylfenyl undesylketoksim, nikkelkomplekser av l-fenyl-4-lauroyl-5-hyd-roksypyrasol, med eller uten ytterligere ligander.
Oksalamider, f.eks. 4,4'-dioktyloksyanilid, 2,2'-dioktyloksy-5,5'-di-tert-butyl-oksanilid, 2,2'-didodesyloksy-5,5'-di-tert-butyloksanilid, 2-etoksy-2'-etyl-oksani-lid, N,N'-bis-(3-dimetylaminopropyl)oksalamid, 2-etoksy-5-tert-butyl-2'-etyloksanilid 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-hydroksyfenyl)-l,3,5-triaziner, f.eks. 2,4,6-tris(2-hydroksy-4-oktyl-oksyfenyl)-1,3,5-triazin, 2-(2-hydroksy-4-oktyloksyfenyl)-4,6-bis-(2,4-dimetylfenyl)-1,3,5-triazin, 2-(2,4-dihydroksyfenyl)-4,6-bis-(2,4-dimetyl-fenyl)-l,3,5-triazin, 2,4-bis-(2-hydroksy-4-propyloksyfenyl)-6-(2,4-dimetyl-fenyl)-1,3,5-triazin, 2-(2-hydroksy-4-oktyl-oksyfenyl)-4,6-bis-(4-metylfenyl)-1,3,5-triazin, 2-(2-hydroksy-4-dodesyloksyfenyl)-4,6-bis-(2,4-dimetylfenyl)-1,3,5-triazin, 2-[2-hydroksy-3-butyloksypropyloksy)fenyl]-4,6-bis-(2,4-dimetylfenyl)-l,3,5-triazin, 2-[2-hydroksy-4-(2-hydroksy-3-oktyloksypropyloksy)-fenyl]-4,6-bis-(2,4-dimetylfenyl)-1,3,5-triazin.
Sterisk hindrede aminer, f.eks. 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-pentametylpiperidin-4-yl)sebasat, bis-(l-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)heksame1ylendiamin og 4-tert-oktylamino-2,6-diklor-l,3,5-s-triazin, tris(2,2,6,6-tetrametyl-4-piperidyl) nitirlotriacetat, 1 J'-(l,2-etandiyl)-bis-(3,3,5,5-tetrametylpiperazinon),4-benzoyl-2,2,6,6-teto piperidin, 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-tetrametylpipeirdyl)sebasat, bis-(l-oktyloksy-2,2,6,6-tetrametylpipeirdyl)suksinat, lineært eller sykliske kondensater av N,N'-bis-(2,2,6,6-tetrametyl-4-piperidyl)heksametylendiamin og 4-morfolino-2,6-diklor-l,3,5-triazin, kondensatene av 2-klor-4,6-di-(4-n-butylamino-2,2,6,6-tetrametyl-piperidyl)-l,3,5-triazin og l,2-bis-(3-aminopropylamino)etan, kondensatene av 2-klor-4,6-di(4-n-butylamino-l,2,2,6,6-pentametylpiperidyl)-l,3,5-triazin og l,2-bis-(3-amino-propyl-amino)etan, 8-acetyl-3-dodesyl-7,7,9,9-tetrametyl-1,3,8-triasa-spiro[4.5]dekan-2,4-dion, 3-dodesyl-1 -(2,2,6,6-tetrametyl-4-piperidyl)pyrrolidin-2,5-dion, 3-dodesyl-1 -
(l,2,2,6,6-pentametyl-4-piperidyl)pyrrolidin-2,5-dion, blandinger av 4-heksadesyloksy-og 4-stearyloksy-2,2,6,6-tetrametylpiperidin, 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-dodesylsuksinimid, N-( 1,2,2,6,6-pentametyl-4-piperidyi)-n-dodesyl-suksinimid, 2-undesyl-7,7,9,9-tetrametyl-l-oksa-3,8-diasa-4-oksospiro-[4.5]dekan, omsetningsproduktet av 7,7,9,9-tetrametyl-2-sykloundesyl-l-oksa-3,8-diasa-4-oksospiro[4.5]dekan og epiklorhydrin, l,l-bis-(l,2,2,6,6-pentametyl-4-piperidylok-sykarbonyl)-2-(4-metoksyfenyl)etan, N,N'-bis-formyl-N,N'-bis-(2,2,6,6-tetrametyl-4-piperidyl)heksametylendiamin, diesteren av 4-metoksymetylenmalonsyre med 1,2,2,6,6-pentametyl-4-hydroksypiperidin, poly[metylpropyl-3-oksy-4-(2,2,6,6-tetrametyl-4-piperi-dyl)]-siloksan, omsetningsproduktet av maleinsyre anhydrid-a-olefinkopolymer og 2,2,6,6-tetrametyl-4-aminopiperidin eller 1,2,2,6,6-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 "Kunststoff-addivite", R. Gåchter/H. Muller, 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 «fe 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', er Ci.22-alkyl, C5.10-hydroksyalkyl, C2_ig-alkenyl, fenyl, OH-, Ci^-alkyl-, Cj^-alkoksy- eller halogen-substituert fenyl, C7.i0-fenylalkyl, Cs-^-sykloalkyl, Ci^-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.i2-alkenyl, fenyl, C7.i2-alkylfenyl, C7.i0-fenylalkyl eller en gruppe -CO-R'4, R'3 er som angitt for R'i eller er Q.ig-alkoksy, R'4 er Ci4-alkyl eller fenyl, R'5 er Q.io-alkylen og R'6 er CM2-alkyl, fenyl, C7.i8-alkylfenyl eller C7.i0-fenylalkyl. 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 CM8-alkyl, så som f.eks. metyl, etyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, heksyl, heptyl, oktyl, desyl, dodesyl eller oktandesyl. R' i og R'3 som hydroksyalkyl er særlig en gruppe -(CH2)n-OH hvor n er 5, 6 eller 7.
R'i og R'3 som alkenyl kan f.eks. 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 f.eks. være tolyl, xylyl, tert-butylfenyl, metoksyfenyl, etoksyfenyl, hydroksyfenyl, klorfenyl eller diklor-fenyl.
R'i og R'3 som fenylalkyl er særlig benzyl, R'2 og R'3 som sykloalkyl eller alkylsyklo-alkyl er særlig sykloheksyl eller metylsykloheksyl, R'2 som alkyl kan særlig være CM-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 f.eks. være metoksy, etoksy, butoksy, heksyloksy, oktyloksy, dodesyloksy, tridesyloksy, tetradesyloksy eller oktadesyloksy. R'5 som Ci.io-alkylen er særlig, CM-alkylen. R'6 som alkyl er særlig C4.i2-alkyl, så som f.eks. butyl, heksyl, oktyl, desyl eller dodesyl. 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, tribenzoyl-metan, 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-sykloheksanoyl-metan, di-pivaloylmetan, 2-acetylsyklopentanon, 2-benzosyklopentanon, metyl-, etyl-, og allyl-diacetoacetat, metyl- og etylbenzoyl-, propionyl- og butyrylacetoacetat, triacetyl-metan, metyl-, etyl-, heksyl-, oktyl-, dodesyl- eller oktadesyl-acetoacetat, metyl-, etyl-, butyl-, 2-etylheksyl-, dodesyl- eller oktadesyl-benzoylacetat, og også Ci.ig-alkylpropion-ylacetater og butyrylacetater; etyl-, propyl-, butyl-, heksyl- eller oktyl-stearoylacetat, og også polysykliske (3-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' j er Q.ig-alkyl, fenyl, OH-, metyl- eller metoksy-substituert fenyl, C7.i0-fenylalkyl eller sykloheksyl, R'2 er hydrogen og R'3 er som definert for R'].
1,3-diketoforbindelsene kan benyttes i en mengde f.eks. 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, vinyliso-butyleter 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, f.eks. diklorstyren; klorerte gummier; klorerte polymerer av etylen; polymerer og etterklorerte polymerer av klor-butadien 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 sub-strater 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. Forkortelsene anvendt for kopolymerene er velkjente for fagfolk på området og har følgende betydning-er: 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 polymerer som er egnet, 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 f.eks. 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 med forbindelsene ifølge oppfinnelsen er særlig fordelaktig for PVC-formu-leringer 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 tungmetall-stabilisatorer medfører også ofte problemer når det gjelder industriell hygiene. Likeledes er bearbeiding av malm som inneholder tungmetaller ofte forbundet med alvorlige inn-virkninger 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.
En fremgangsmåte for å stabilisere PVC omfatter å tilsette til PVC minst en av de ovennevnte stabilisatorkombinasjoner.
Stabilisatorene kan hensiktsmessig bli innlemmet gjennom følgende metoder: Som en emulsjon eller dispersjon (f.eks. i form av en pastalignende blanding, og med hensyn til dette er det en fordel at stabilisatorblandingen gir en stabil pasta); som tørrblanding ved innblanding av ytterligere komponenter eller polymerblandinger; som direkte tilsetning i bearbeidingsapparaturen (f.eks. 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 med forbindelsene ifølge oppfinnelsen kan fremstilles på kjent måte ved å anvende kjente innretninger, slik som den ovennevnte bearbeidingsapparatur, for å blande forbindelsen ifølge oppfinnelsen og eventuelt ytterligere additiver med PVC. I dette tilfelle kan stabilisatorene tilsettes hver for seg, som en blanding eller i form av såkalte kon-sentratblandinger.
PVC stabilisert i henhold til den foreliggende oppfinnelse, kan bringes over i ønsket form ved å benytte kjente metoder. Eksempler på slike metoder er oppmaling, kalandrering, ekstrudering, sprøytestøping eller spinning, og også ekstruderingsformblåsing. Stabilisert PVC kan også bearbeides til skummaterialer.
PVC stabilisert med forbindelser ifølge oppfinnelsen er f.eks. 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). Spesielt anvendes stabilisert PVC til stivt PVC-skum og PVC-rør for drikkevann eller avløpsvann, trykkrør, gassrør, kabelledningsrør og kabelbeskyttelsesrør, rør for indu-strielle 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 metoder [f.eks. 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, Berichte 99 3530 (1966) og CA 70 87727
(1969)].
Fremstilte forbindelser 1 til 22 er fremstilt som oppsummert i tabell 1.
Som i resten av beskrivelsen, så er deler og prosentandeler basert på vekt så sant annet ikke er angitt.
Eksemplene nedenfor viser tydelig at stabilisatorforbindelsene ifølge oppfinnelsen gir forbedrede resultater sammenlignet med kjent teknikk når det gjelder fargen til å begynne med, bibehold av farge (gjennomsnittsfarge) og langstidsstabilitet - YI-målinger.
Fremstillingseksempler
Eksempel 1
En blanding av 31,0 g (0,2 mol) 6-amino-l,3-dimetyluracil, 8,1 g (0,11 mol) av en 37% sterk formaldehydløsning, 120 ml toluen og 100 ml iseddik ble varmet under tilbakeløp inntil 15 ml av en blanding av vann/iseddik var blitt samlet opp i en vannseparator. Blandingen ble deretter avkjølt til 20 °C og den dannede utfelling ble filtrert fra med suging, vasket med toluen og tørket under redusert trykk ved 100 °C.
Utbytte: 30,6 g = 95% av teoretisk.
Eksempel 15
15,5 g (0,1 mol) 6-amino-l,3-dimetyluracil, 14,0 g (0,1 mol) benzoylklorid og 16 g pyridin ble varmet ved 116 °C under omrøring i 4 timer. Etter avkjøling til 20 °C ble reaksjonsblandingen rørt ut i 250 ml vann og den resulterende utfelling ble filtrert fra med suging etter 2 timer, vasket med vann og tørket i en vakuumtørkeovn ved 100 °C. Utbytte: 21,7 g = 84% av teoretisk.
Eksempel 18
I en 500 ml 2-halset kolbe med magnetrøret, termometer, vannseparator og tilbakeløpskjøler ble 34 g (0,22 mol) 6-amino-l,3-dimetyluracil, 45 g (0,3 mol) metyl-4-kloracetoacetat, 80 ml eddiksyre og 100 ml toluen oppvarmet under tilbakeløp og med omrøring i 3,5 timer. Under denne tid ble 10,2 ml vann/eddiksyre-blanding tatt ut. Deretter ble reaksjonsblandingen avkjølt til 30 °C (dannelse av utfelling) og deretter til 0 °C. Utfellingen ble isolert, vasket med vann og tørket.
Utbytte: 18,7 g = 35,8% av teoretisk.
Eksempel 19
15,5 g (0,1 mol) 6-amino-l,3-dimetyluracil, 26,4 g (0,1 mol) 4-(dimetylaminoetylen)-2,6-di-tert-butylfenol og 100 ml eddiksyre ble varmet ved 121 °C under omrøring i 2,5 timer. Etter avkjøling til 20 °C ble reaksjonsblandingen rørt ut i 500 ml vann, og den resulterende utfelling ble filtrert fra med suging, vasket med vann og tørket i en vakuumtørkeovn ved 100 °C.
Utbytte: 37,3 g = 100% av teoretisk.
Eksempel 20
31,0 g (0,2 mol) 6-amino-l,3-dimetyluracil, 25,0 (0,22 mol) glutarsyreanhydrid og 100 ml eddiksyre ble varmet ved 120 °C i 90 minutter, og deretter avkjølt til 20 °C. Reaksjonsblandingen ble rørt ut i 500 ml vann og den hvite utfelling ble filtrert fra med suging, vasket med vann og tørket til konstant vekt.
Utbytte: 31,2 g = 57,9% av teoretisk.
Eksempel 21
18,8 g (0,07 mol) av forbindelsen fra eksempel 20 ble omrørt ved koking under tilbakeløp med 100 ml etanol og 2 ml konsentrert svovelsyre i 3 timer, hvoretter reaksjonsløsningen ble avkjølt til 20 °C og deretter rørt ut i 500 ml vann. Dette ble nøytralisert med natriumkarbonat, og det utfelte reaksjonsprodukt ble filtrert av med suging, vasket med vann og tørket.
Utbytte: 16,0 g - 76,9% av teoretisk.
Eksempel 22
En smelte av 15,4 g (0,06 mol) 6-amino-l,3-di-n-butyluracil og 29,4 g (0,13 mol) benzosyreanhydrid ble omrørt ved 110-120 °C i 4 timer, og deretter avkjølt og oppløst i 20 ml metanol. Denne oppløsning ble rørt ut i en løsning av 250 ml vann og 8 g natriumhydroksid. Det rødbrune faste stoff ble filtrert fra med suging, tørket og rekrystallisert fra 30 ml etylacetat.
Utbytte: 8,3 g = 40,3% av teoretisk.
Statisk varmetest
En tørrblanding bestående av
100,0 deler Evipol SH 6030 = PVC K-tall 60
5,0 deler ESO = epoksidert soyabønneolje
0,4 del Loxiol G 71 S = multikomponent-ester med
høy molekylvekt
0,8 del Irgastab CH 300 = flytende diaryl-di-
alkyl-fosfitt
og i hvert tilfelle én av stabilisatorene angitt i tabeller 2 og 3 (korresponderende til eksemplene i tabell 1) ble valset på et sett blandevalser ved 180 °C i 5 minutter. Fra den resulterende valsede folie ble det tatt ut 0,3 mm tykke filmprøvestykker. Filmprøvene ble underkastet termisk belastning ved 190 °C i en ovn. Gulhetsindeksen (Yl) i henhold til ASTM D-1925-70 ble bestemt i intervaller på 5 minutter. Resultatene er gitt i tabell 2 (1,0 vektdel stabilisator) og tabell 3 (0,6 vektdel stabilisator) nedenfor. Lave YI-verdier angir god stabilisering.
Claims (18)
1. Forbindelse, karakterisert ved den generelle formel I
hvor
Y er oksygen eller svovel,
Ri og R2 er, uavhengig av hverandre, Ci_i8-alkyl, C3.6-alkenyl eller C5.8-sykloalkyl, som eventuelt er substituert med Ci.4-alkoksy, C5„8-sykloalkyl, -OH og/eller Cl; C7.9-fenylalkyl hvor eventuelt fenylringen er substituert med Ci^-alkyl, Ci_4-alkoksy, C5.8-sykloalkyl, -OH og/eller Cl; eller fenyl,
R3 er H; CM8-alkyl som eventuelt er substituert med -OH; eller fenyl som eventuelt er substituert med -OH, og
R5 er H, Ci.i2-alkyl eller fenyl som eventuelt er substituert med -OH, CM-alkyl, Ci^-alkoksy, -C=0(OR6) og/eller -O-COR*, og
R<5 er rettkjedet eller forgrenet Ci.i2-alkyl, eller rettkjedet eller forgrenet C2.J2-alkenyl.
2. Forbindelse med generell formel I ifølge krav 1, karakterisert ved at Y er oksygen.
3. Forbindelse med generell formel I ifølge krav 1, karakterisert ved at Y er oksygen og
Ri og R2 er uavhengig av hverandre Ci.8-alkyl, allyl eller C7.9-fenylalkyl, og R3 er H, Ci.i8-alkyl som er usubstituert eller substituert med -OH, eller fenyl som er usubstituert eller"substituert med -OH, og
R5 er H, Q.n-alkyl, eller fenyl som er usubstituert eller substituert med -OH, CM-alkyl, Ci_4-alkoksy, -C=0(OR6) og/eller -0-COR6, hvor R6 er rettkjedet eller forgrenet .Cr_i2-alkyl, eller rettkjedet eller forgrenet C2.i2-alkenyl.
4. Materiale, karakterisert ved at det omfatter en klorholdig polymer og minst én forbindelse med generell formel II
hvor
n er 1 eller 2,
Y er oksygen eller svovel,
Ri og R2 er uavhengig av hverandre CVi8-alkyl, C3.6-alkenyl, C5.8-sykloalkyl som er usubstituert eller substituert med C^-alkoksy, C5.8-sykloalkyl, -OH og/eller Cl; C7.9-fenylalkyl som er usubstituert eller fenylringen er substituert med Ci-4-alkyl, CM-alkoksy, C5.8-sykloalkyl, -OH og/eller Cl; eller fenyl,
R3 er H, Cj.is-alkyl som er usubstituert eller substituert med -OH; eller fenyl som usubstituert eller substituert med -OH, og
R4 er -(C=0)-CM2-alkyl, -C(=0)-0-CM2-alkyl, -(C=O)-C0-i2-alkylen-(C=O)OZ,
hvor Zer H eller Ci.6-alkyl, -(C=0)-fenyl, eller og når
n er 2,
R4 er gruppen -CHR5-, hvor
R5 er H, Ci.n-alkyl eller fenyl som er usubstituert eller substituert med -OH, CM-alkyl-, Ci.4-alkoksy, -C=0(ORe) og/eller -0-COR6, hvor R^ er rettkjedet eller forgrenet Ci.i2-alkyl, eller rettkjedet eller forgrenet C2-i2-alkenyl.
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, (3-dikarbonylforbindelser, mykgjørere, fyllstoffer, smøremidler og pigmenter.
8. Materiale ifølge krav 4, karakterisert ved at det som fyllstoff inneholder kritt.
9. Materiale ifølge krav 4, karakterisert ved at det som smøremiddel inneholder kalsiumstearat.
10. Materiale ifølge krav 4, karakterisert ved at det som pigment inneholder titandioksid og/eller zirkoniumoksid og/eller bariumsulfat.
11. Materiale ifølge krav 4, karakterisert ved at det inneholder minst en polyol og/eller en disakkaridalkohol.
12. Materiale ifølge krav 4, karakterisert ved at det iineholder minst en glysidylforbindelse.
13. Materiale ifølge krav 4, karakterisert ved at det inneholder minst en perkloratforbindelse.
14. Materiale ifølge krav 4, karakterisert ved at det inneholder minst en zeolittforbindelse.
15. Materiale ifølge krav 4, karakterisert ved at det inneholder minst en lagoppbygd gitterforbindelse.
16. Materiale ifølge krav 4, karakterisert ved at det inneholder minst ett hydrotalcitt. ^
17. Fremgangsmåte for å stabilisere klorholdige polymerer, karakterisert ved at det i polymerene innarbeides minst en forbindelse som har formel II ifølge krav 4.
18. Anvendelse av en forbindelse med generell formel II ifølge krav 4, som stabilisator for halogenholdige polymerer og resirkulerte materialer med slike.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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CH137198 | 1998-06-26 |
Publications (3)
Publication Number | Publication Date |
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NO993183D0 NO993183D0 (no) | 1999-06-25 |
NO993183L NO993183L (no) | 1999-12-27 |
NO312895B1 true NO312895B1 (no) | 2002-07-15 |
Family
ID=4208860
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Application Number | Title | Priority Date | Filing Date |
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NO19993183A NO312895B1 (no) | 1998-06-26 | 1999-06-25 | 5-substituerte 6-aminouraciler som stabilisatorer for halogenholdige polymerer, materialer omfattende slike forbindelserog anvendelse av slike forbindelser |
Country Status (9)
Country | Link |
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US (1) | US6156830A (no) |
EP (1) | EP0967208B1 (no) |
JP (1) | JP2000034282A (no) |
AT (1) | ATE222242T1 (no) |
CA (1) | CA2269877A1 (no) |
DE (1) | DE59902320D1 (no) |
DK (1) | DK0967208T3 (no) |
ES (1) | ES2182420T3 (no) |
NO (1) | NO312895B1 (no) |
Families Citing this family (21)
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BE1012673A3 (fr) * | 1999-05-10 | 2001-02-06 | Solvay | Nouveaux derives de 6-amino-uracile, leur preparation et leur utilisation. |
ITVA20000023A1 (it) | 2000-07-19 | 2002-01-19 | Lamberti Spa | Composizioni di pvc stabili al calore. |
US6835328B2 (en) * | 2002-07-08 | 2004-12-28 | Crompton Corporation | Overbased metal carbonate/carboxylate microemulsions and halogen-containing polymers containing same |
CN102134230B (zh) | 2004-03-15 | 2019-06-28 | 武田药品工业株式会社 | 二肽基肽酶抑制剂 |
DE602007005628D1 (de) * | 2006-05-02 | 2010-05-12 | Basf Se | Derivate von pyrimidinen als flammschutzmittel |
CN101437886B (zh) * | 2006-05-02 | 2011-11-09 | 西巴控股有限公司 | 作为阻燃剂的嘧啶衍生物 |
DE102007037795A1 (de) | 2007-08-10 | 2009-02-12 | Nabaltec Ag | Stabilisatorsysteme für halogenhaltige Polymere |
DE102008018872A1 (de) | 2008-04-14 | 2009-10-15 | Ika Innovative Kunststoffaufbereitung Gmbh & Co. Kg | Stabilisatorsystem für halogenhaltige Polymere |
DE102008020203A1 (de) | 2008-04-22 | 2009-10-29 | Catena Additives Gmbh & Co. Kg | Lösemittelfreie High Solids (One-Pack)-Stabilisatoren für halogenhaltige Polymere |
EP2123659A1 (en) * | 2008-05-15 | 2009-11-25 | Arkema France | High purity monoalkyltin compounds and uses thereof |
US8354462B2 (en) * | 2009-11-30 | 2013-01-15 | Chemson Polymer Additives AG | Heat stabilizers containing hydrotalcite particles with specific zeta potentials that demonstrate improved processing and performance in molded vinyl compounds |
DE102010020486A1 (de) | 2010-05-14 | 2011-11-17 | Catena Additives Gmbh & Co. Kg | Flammgeschützte halogenhaltige Polymere mit verbesserter Thermostabilität |
FR2986003B1 (fr) | 2012-01-24 | 2015-01-16 | Arkema France | Procede de preparation de polymeres halogenes |
CN107001697B (zh) | 2014-11-24 | 2019-06-28 | 路博润先进材料公司 | 用于氯乙烯聚合物树脂的新型偶联尿嘧啶化合物 |
CN104479257A (zh) * | 2014-12-31 | 2015-04-01 | 浙江工业大学 | 尿嘧啶类化合物作为透明聚乙烯制品的有机热稳定剂的应用 |
CN105315485B (zh) * | 2015-11-05 | 2018-08-24 | 浙江工业大学 | 一种有机透明复合热稳定剂及其制备方法与应用 |
CN108383800A (zh) * | 2018-03-02 | 2018-08-10 | 广东工业大学 | 氨基脲嘧啶马来酰胺酸盐及制备方法和聚氯乙烯热稳定剂 |
CN111072574B (zh) * | 2019-12-03 | 2023-03-14 | 广东工业大学 | 5,6-二氨基-1,3-二烃取代尿嘧啶及其制备方法 |
CN114014816A (zh) * | 2021-11-10 | 2022-02-08 | 山东慧科助剂股份有限公司 | 辛醛双脲嘧啶及其制备方法和应用 |
CN113912553A (zh) * | 2021-11-10 | 2022-01-11 | 山东慧科助剂股份有限公司 | 戊醛双脲嘧啶及其制备方法和应用 |
CN115073815B (zh) * | 2022-08-11 | 2022-11-18 | 山东浩纳新材料科技集团有限公司 | 一种环保型热稳定剂及其制备方法 |
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DE888167C (de) * | 1944-02-23 | 1953-08-31 | Cassella Farbwerke Mainkur Ag | Stabilisierungsmittel fuer halogenhaltige Verbindungen |
DE1694873C3 (de) * | 1966-02-12 | 1973-11-08 | Ciba-Geigy Marienberg Gmbh, 6140 Marienberg | Stabilisierung von Vinylchlorid polymerisaten |
US4105627A (en) * | 1976-09-20 | 1978-08-08 | Argus Chemical Corporation | Mercaptoheterocyclic resin stabilizers |
DE3162945D1 (en) * | 1980-06-02 | 1984-05-10 | Ciba Geigy Ag | Chlorine-containing thermoplastic polymers stabilized with amino-thiouracils |
DE3265213D1 (en) * | 1981-05-26 | 1985-09-12 | Ciba Geigy Ag | Chlorine-containing thermoplastic polymers stabilised with amino uracils |
US4656209A (en) * | 1982-05-26 | 1987-04-07 | Ciba-Geigy Corporation | Chlorinated thermoplastics stabilized with aminouracils |
JPS6323941A (ja) * | 1986-07-17 | 1988-02-01 | Bridgestone Corp | 低発熱性ゴム組成物 |
US4816585A (en) * | 1987-03-05 | 1989-03-28 | Olin Corporation | Tetraalkylpiperidinyl substituted uracil derivatives and their use as ultraviolet light stabilizers |
US4904714A (en) * | 1987-10-02 | 1990-02-27 | Olin Corporation | Synthetic resin composition and its method of use |
DE58908208D1 (de) * | 1988-07-29 | 1994-09-22 | Ciba Geigy Ag | Thiouracile als Stabilisatoren für chlorhaltige Polymerisate. |
KR0151811B1 (ko) * | 1993-12-21 | 1998-10-15 | 강박광 | 신규한 항바이러스성 2,4-피리미딘디온 유도체 및 그의 제조방법 |
ATE257163T1 (de) * | 1995-10-13 | 2004-01-15 | Crompton Vinyl Additives Gmbh | Stabilisatorkombinationen für chlorhaltige polymere |
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 DE DE59902320T patent/DE59902320D1/de not_active Expired - Lifetime
- 1999-03-17 EP EP99105429A patent/EP0967208B1/de not_active Expired - Lifetime
- 1999-03-17 AT AT99105429T patent/ATE222242T1/de not_active IP Right Cessation
- 1999-03-17 ES ES99105429T patent/ES2182420T3/es not_active Expired - Lifetime
- 1999-03-17 DK DK99105429T patent/DK0967208T3/da active
- 1999-04-22 CA CA002269877A patent/CA2269877A1/en not_active Abandoned
- 1999-06-01 US US09/323,778 patent/US6156830A/en not_active Expired - Fee Related
- 1999-06-24 JP JP11178646A patent/JP2000034282A/ja active Pending
- 1999-06-25 NO NO19993183A patent/NO312895B1/no not_active IP Right Cessation
Also Published As
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ES2182420T3 (es) | 2003-03-01 |
ATE222242T1 (de) | 2002-08-15 |
EP0967208B1 (de) | 2002-08-14 |
NO993183L (no) | 1999-12-27 |
EP0967208A1 (de) | 1999-12-29 |
DK0967208T3 (da) | 2002-11-18 |
DE59902320D1 (de) | 2002-09-19 |
CA2269877A1 (en) | 1999-12-26 |
JP2000034282A (ja) | 2000-02-02 |
US6156830A (en) | 2000-12-05 |
NO993183D0 (no) | 1999-06-25 |
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