DE2637193A1 - (7)-Amino-(1,3,5)-tri:aza-adamantane derivs. - used as stabilisers for organic polymer, esp. against UV irradiation and heat - Google Patents
(7)-Amino-(1,3,5)-tri:aza-adamantane derivs. - used as stabilisers for organic polymer, esp. against UV irradiation and heatInfo
- Publication number
- DE2637193A1 DE2637193A1 DE19762637193 DE2637193A DE2637193A1 DE 2637193 A1 DE2637193 A1 DE 2637193A1 DE 19762637193 DE19762637193 DE 19762637193 DE 2637193 A DE2637193 A DE 2637193A DE 2637193 A1 DE2637193 A1 DE 2637193A1
- Authority
- DE
- Germany
- Prior art keywords
- polymer
- carbon atoms
- group
- amino
- triazaadamantane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000003381 stabilizer Substances 0.000 title claims abstract description 15
- 229920000620 organic polymer Polymers 0.000 title claims abstract description 7
- WENISBCJPGSITQ-UHFFFAOYSA-N 1-azatricyclo[3.3.1.13,7]decane Chemical compound C1C(C2)CC3CC1CN2C3 WENISBCJPGSITQ-UHFFFAOYSA-N 0.000 title 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 title 1
- 229920000642 polymer Polymers 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- WXMJWQSOWLXJOA-UHFFFAOYSA-N 7-amino-1,3,5-triazaadamantane Chemical compound C1N(C2)CN3CN2CC1(N)C3 WXMJWQSOWLXJOA-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 229920000098 polyolefin Polymers 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 abstract description 3
- -1 7-pentylideneamino-1,3,5-triazaadamantane 7-iso-pentylideneamino-1,3,5-triazaadamantane 7-benzylideneamino-1,3,5-triazaadamantane Chemical compound 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- 239000004611 light stabiliser Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XZDLLQQBTVSJJR-UHFFFAOYSA-N 1,3,5-triazaadamantane Chemical compound C1N(C2)CN3CC1CN2C3 XZDLLQQBTVSJJR-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- HJVKQVTXROGXGE-UHFFFAOYSA-N 1,2,3-triazatricyclo[3.3.1.13,7]decane Chemical class C1N(N2)CC3CC1CN2C3 HJVKQVTXROGXGE-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 229920001059 synthetic polymer Polymers 0.000 description 3
- JIVGSHFYXPRRSZ-UHFFFAOYSA-N 2,3-dimethoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1OC JIVGSHFYXPRRSZ-UHFFFAOYSA-N 0.000 description 2
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 150000004002 naphthaldehydes Chemical class 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920013639 polyalphaolefin Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- ATLWFAZCZPSXII-UHFFFAOYSA-N (2-octylphenyl) 2-hydroxybenzoate Chemical compound CCCCCCCCC1=CC=CC=C1OC(=O)C1=CC=CC=C1O ATLWFAZCZPSXII-UHFFFAOYSA-N 0.000 description 1
- VQRWCUPUVWCWRI-UHFFFAOYSA-N 1,2,3-triazatricyclo[3.3.1.13,7]decan-2-amine Chemical compound NN1N2CC3CC(CN1C3)C2 VQRWCUPUVWCWRI-UHFFFAOYSA-N 0.000 description 1
- ZVBDUOPNQLWOGH-UHFFFAOYSA-N 1-methyl-4-oct-1-enylbenzene Chemical compound CCCCCCC=CC1=CC=C(C)C=C1 ZVBDUOPNQLWOGH-UHFFFAOYSA-N 0.000 description 1
- IHWDIGHWDQPQMQ-UHFFFAOYSA-N 1-octadecylsulfanyloctadecane Chemical compound CCCCCCCCCCCCCCCCCCSCCCCCCCCCCCCCCCCCC IHWDIGHWDQPQMQ-UHFFFAOYSA-N 0.000 description 1
- FLSKKFALEYBSJE-UHFFFAOYSA-N 2,6-ditert-butyl-4-[1-(3,5-ditert-butyl-4-hydroxyphenyl)butyl]phenol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1C(CCC)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FLSKKFALEYBSJE-UHFFFAOYSA-N 0.000 description 1
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 1
- UCMLFRCVHNLWOH-UHFFFAOYSA-N 2-methyl-1-(4-propan-2-ylphenyl)propan-2-ol Chemical compound CC(C)C1=CC=C(CC(C)(C)O)C=C1 UCMLFRCVHNLWOH-UHFFFAOYSA-N 0.000 description 1
- DTALCVXXATYTQJ-UHFFFAOYSA-N 2-propan-2-ylbenzaldehyde Chemical compound CC(C)C1=CC=CC=C1C=O DTALCVXXATYTQJ-UHFFFAOYSA-N 0.000 description 1
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 1
- ZCILGMFPJBRCNO-UHFFFAOYSA-N 4-phenyl-2H-benzotriazol-5-ol Chemical class OC1=CC=C2NN=NC2=C1C1=CC=CC=C1 ZCILGMFPJBRCNO-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 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 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical class NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 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 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- YNKMHABLMGIIFX-UHFFFAOYSA-N benzaldehyde;methane Chemical compound C.O=CC1=CC=CC=C1 YNKMHABLMGIIFX-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/18—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3495—Six-membered rings condensed with carbocyclic 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)
Abstract
Description
Neue Derivate des 7-Amino-1,3,5-triazaadamantans New derivatives of 7-amino-1,3,5-triazaadamantane
als Lichtschutzmittel Die Erfindung betrifft neue Triazaadamantanverbindungen, ein Verfahren zu ihrcr erstellung und ihre Verwendung als Lichtschutzmittel für synthetische Polymere. as light stabilizers The invention relates to new triazaadamantane compounds, a process for their creation and their use as a light stabilizer for synthetic polymers.
Die neuen Verbindungen entsprechen der Formel in der - wenn n für 1 steht - R eine Alkyl- oder Isoalkylgruppe mit 1 bis 17 C-Atomens eine Phenylalkylgruppe mit 1 bis 4 C-Atomen in der Alkylkette, oder eine Phenyl- oder Naphthylgruppe, die gegebenenfalls durch bis zu 2 Chloratome, durch eine ilydroxygruppe oder durch bis zu 3 Alkoxy- oder Alkylgruppen mit 1 bis 4 C-Atomen substituiert ist, bedeutet, oder einen heterocyclischen 5- oder 6-Ring mit einem N- oder 0-Atom darstellt, während bei n = 2 R die Bedeutung einer Alkylengruppe mit 2 bis 6 C-Atomen oder einer Phenylengruppe hat.The new compounds correspond to the formula in which - when n is 1 - R is an alkyl or isoalkyl group with 1 to 17 carbon atoms, a phenylalkyl group with 1 to 4 carbon atoms in the alkyl chain, or a phenyl or naphthyl group, which is optionally replaced by up to 2 chlorine atoms, is substituted by a hydroxy group or by up to 3 alkoxy or alkyl groups with 1 to 4 carbon atoms, or represents a heterocyclic 5- or 6-ring with one N or 0 atom, while when n = 2 R is the Has the meaning of an alkylene group with 2 to 6 carbon atoms or a phenylene group.
Repräsentative Vertreter der erfindungsgemäßen Verbindungen sind z. B.: 7-Pentylidenamino-1,3,5-triazaadamantan 7-iso-Pentylidenamino-1,3,5-triazaadamantan 7-Benzylidenamino-1,3,5-triazaadamantan 7-(4-IWIethy3benzylidenamino)-1,3,5-triazaadamantan 7-(4-iso-Propylbenzylidenamino)-1,3,5-triazaadamantan-7-Furfurylidenamino-1,3,5-triazaadamantan 7-Salizylidenamino-1 , 3,5-triazaadamantan -Bis-(1,3,5-triazaadamantylimino-7)-p-Xylol Die erfindungsgemäßen Triazaadamantanderivate lassen sich in einfacher Weise durch Kondensation des 7-Amino- 1 3, 5-triazaadamantans (hergestellt z. B. nach B.B. Ilodge, J. Org. Chem., 37 (1972), 5. 320-321), mit Mono- oder Dialdehyden, wie in der nachstehenden Reaktionsgleichung veranschaulicht, synthetisieren. Representative representatives of the compounds according to the invention are, for. E.g .: 7-pentylideneamino-1,3,5-triazaadamantane 7-iso-pentylideneamino-1,3,5-triazaadamantane 7-benzylideneamino-1,3,5-triazaadamantane 7- (4-IWIethy3benzylidenamino) -1,3, 5-triazaadamantane 7- (4-iso-propylbenzylideneamino) -1,3,5-triazaadamantane-7-furfurylideneamino-1,3,5-triazaadamantane 7-salicylideneamino-1,3,5-triazaadamantane -Bis- (1,3 , 5-triazaadamantylimino-7) -p-xylene The triazaadamantane derivatives according to the invention can be obtained in a simple manner by condensation of 7-amino-1 3, 5-triazaadamantane (prepared, for example, according to BB Ilodge, J. Org. Chem., 37 (1972), pp. 320-321), with mono- or dialdehydes, as illustrated in the reaction equation below.
Dic Reaktion wird in einem inerten organischen Lösungsmittel, z. B. in einem Alkohol oder in Toluol, bei einer Temperatur von 20 bis 120, vorzugsweise 80 bis 120 C° unter Zusatz katalytischer Mengen p-Toluolsulfonsäure oder Ammoniumacetat durchgeführt.The reaction is carried out in an inert organic solvent, e.g. B. in an alcohol or in toluene, at a temperature of 20 to 120, preferably 80 to 120 ° C with the addition of catalytic amounts of p-toluenesulfonic acid or ammonium acetate carried out.
Als Aldehyde kommen Mono- und Dialdehyde in Frage Bevorzugt geeignet sind aliphatische Monoaldehyde mit 2 bis 18, vorzugsweise-2 bis 12 und insbesondere 3 bis 7 C-Atomen, ferner durch einen Phenylrest substituierte aliphatische Monoaldehyde mit 2 bis 5 C-Atomen. Auch Benzaldehyd und die Naphthaldehyde, die gegebenenfalls durch bis zu 2 Ohloratome, durch eine hydroxygruppe oder durch bis zu 3 Allçyl- oder Alkoxygruppen mit 1 bis 4 C-Atomen substituiert sein können, sind einsetzbar. Es ist schließlich auch möglich, Monoaldehyde heterocyclischer 5- oder 6-Ringe mit N oder 0 als Heteroatom mit dem Aminotriazaadamantan zu kondensieren. Geeignete Dialdehyde sind aliphatische α,#-Dialdehyde mit 4 bis 8 C-Atomen, sowie bevorzugt Phenylen-Dialdehyde. Im einzelnen seien beispielsweise genannt: Propionaldehyd, Butyraldehyd, iso-Butyraldehyd, Valeraldehyd, iso-Valeraldehyd, Capronaldehyd, Benzaldehyd, Anisaldehyd, Chlorbenzaldehyd, Dimethoxybenzaldehyd, Tolylaldehyd, Naphthaldehyd, iso-Propylbenzaldel-Lyd , Salizylaldehyd, Furfurol, IIydrozir.ltaldehyd und Terephthalaldehyd.Suitable aldehydes are mono- and dialdehydes. Preferred suitable are aliphatic monoaldehydes with 2 to 18, preferably -2 to 12 and especially 3 to 7 carbon atoms, furthermore aliphatic monoaldehydes substituted by a phenyl radical with 2 to 5 carbon atoms. Also benzaldehyde and the naphthaldehydes that possibly by up to 2 chlorine atoms, by a hydroxy group or by up to 3 alkyl or alkoxy groups can be substituted with 1 to 4 carbon atoms. Finally, it is also possible to use monoaldehydes with heterocyclic 5- or 6-rings N or 0 to condense as a hetero atom with the aminotriazaadamantane. Suitable Dialdehydes are aliphatic α, # - dialdehydes with 4 to 8 carbon atoms, and preferred Phenylene dialdehydes. Examples include: propionaldehyde, Butyraldehyde, iso-butyraldehyde, valeraldehyde, iso-valeraldehyde, capronaldehyde, benzaldehyde, Anisaldehyde, chlorobenzaldehyde, dimethoxybenzaldehyde, tolylaldehyde, naphthaldehyde, iso-propylbenzaldehyde, salicylaldehyde, furfurol, IIydrozir.ltaldehyd and terephthalaldehyde.
Es wurde überraschenderweise gefunden, daß die erfindungsgemäßen Triazaadamantanverbindungen synthetische Polymermassen gegen die Zersetzung durch Wärme und insbesondere ultraviolette Strahlung hervorragend schützen. Dabei werden die Parbei.genschaften der Polyncrmassen nicht beeinträchtigt. Besonders gut geeignet sind die neuen Verbindungen als Lichtschutzmittel für Polyolefine, wie z. B. Polyisopren, Polybutadien, Polystyrol und insbesondere Polypropylen und Polyäthylen, ferner für Äthylen-Propylen-Copolymere, Äthylen-Buten-Copolymere, Äthylen-Vinylacetat-Copolymere, Styrol-Butadien-Copolymere und Acrylnitril-Styrol-Butadien-Copolymere.It has surprisingly been found that the triazaadamantane compounds according to the invention synthetic polymer compositions against decomposition by heat and especially ultraviolet Excellent protection from radiation. In doing so, the pairing properties of the polynomials not affected. The new compounds are particularly suitable as light stabilizers for polyolefins such as B. polyisoprene, polybutadiene, polystyrene and in particular Polypropylene and polyethylene, also for ethylene-propylene copolymers, ethylene-butene copolymers, Ethylene-vinyl acetate copolymers, styrene-butadiene copolymers and acrylonitrile-styrene-butadiene copolymers.
Der vorstehend genannte Begriff "synthetische Polymermassen" soll außerdem Polyvinylchlorid, Polyvinylidenchlorid und Oopolymere der entsprechenden Monomeren mit anderen olefinisch ungesättigten }-ionomeren, ferner Polymere, wie Polyacetale, Polyester, Polyamide, Polyacrylate, Polyurethane und Epoxyharze umfassen.The aforementioned term "synthetic polymer compositions" is intended to also polyvinyl chloride, polyvinylidene chloride and copolymers of the corresponding Monomers with other olefinically unsaturated} ionomers, and also polymers, such as Polyacetals, polyesters, polyamides, polyacrylates, polyurethanes, and epoxy resins include.
Die Menge der den organischen Polymeren zuzusetzenden neuen Verbindungen kann in Abhängigkeit voll der Art, den Eigenschaften und den speziellen Anwendungen des zu stabilisierenden Polymeren crheblich schwanken, Eur die meisten Anwendungen werden 0,01 bis 5 Gew.-Teile, vorzugsweise 0,05 bis 3 Gew.-Teile, insbesondere 0,1 bis 1,5 Gew.-Teile, bezogen auf die Menge des organischen Polymeren, eingesetzt. Es kann eine Verbindung allein oder eine Mischung aus mehreren Verbindungen verwendet werden.The amount of new compounds to be added to the organic polymers can be fully dependent on the type, the properties and the special Applications of the polymer to be stabilized vary considerably, Eur most Applications are 0.01 to 5 parts by weight, preferably 0.05 to 3 parts by weight, in particular 0.1 to 1.5 parts by weight, based on the amount of the organic polymer, are used. One compound can be used alone or a mixture of several compounds will.
Die erfindungsgemäßen Verbindungen werden nach allgemein üblichen Methoden in die Polymermassen eingearbeitet. Alternativ kann eine Lösung, Suspension oder Emulsion des Stabilisators in das Polymere direkt oder in eine Lösung, Suspension oder emulsion desselben eingemischt werden, wobei das Lösungsmittel anschliessend entfernt wird.The compounds according to the invention are generally customary Methods incorporated into the polymer masses. Alternatively, a solution, suspension or emulsion of the stabilizer in the polymer directly or in a solution, suspension or emulsion of the same are mixed in, with the solvent then Will get removed.
Die erfindungsgemäßen Stabilisatoren sind für sich allein oder im Gemisch mit einem oder mehreren üblichen Stabilisatoren, wie z. B. Antioxidantien auf Phenol- und Sulfidbasis, Uv-Absorbern und Lichtschutzmitteln, Phosphitstabilisatoren, Metallverbindungen, Epoxystabilisatoren, mehrwertigen Alkoholen und auch zusammen mit Antistatika, Flammschutzmitteln und Pigmenten wirksam.The stabilizers according to the invention are alone or in the Mixture with one or more conventional stabilizers, such as. B. Antioxidants based on phenol and sulfide, UV absorbers and light stabilizers, phosphite stabilizers, Metal compounds, epoxy stabilizers, polyhydric alcohols and also together effective with antistatic agents, flame retardants and pigments.
Beispiele für geeignete Antioxidantien sind solche vom Typ der sterisch gehinderten Phenole wie 22 6-Di-t-butyl-p-kresol, 2,6-Di-octadocyl-p-kresol, 4,4'-Butyliden-bis-(2,6-di-t-butyl-phenol), 4,4'-Thio-bis-(2-t-butyl-5-methylphenol), phenolisch Triazinverbindungen, Tiliodipropionsäureester von Fettalkoholen, Dioctadecylsulfid und -disulfid.Examples of suitable antioxidants are those of the steric type hindered phenols such as 22 6-di-t-butyl-p-cresol, 2,6-di-octadocyl-p-cresol, 4,4'-butylidene-bis- (2,6-di-t-butyl-phenol) , 4,4'-thio-bis- (2-t-butyl-5-methylphenol), phenolic triazine compounds, tiliodipropionic acid esters of fatty alcohols, dioctadecyl sulfide and disulfide.
Zu den UV-Absorbern und Lichtschutzmitteln gehören z. B. 2-(2'-Hydroxyphenyl)-benzetriazole wie 2-(2'-Hydroxy-5'-methyl-phenyl) benzotriazol, 2-Hydroxybenzophenone wie 2-IIydroxy-4-octoxy-benzophenon Stabilisatoren aus der Gruppe der Salizy.Late wie Octylphenylsalizylat, Nickelchelate, Oxalsäurediamide und sterisch gehinderte Piperidinverbindungen.The UV absorbers and light stabilizers include, for. B. 2- (2'-hydroxyphenyl) benzetriazoles such as 2- (2'-hydroxy-5'-methyl-phenyl) benzotriazole, 2-hydroxybenzophenones such as 2-II-hydroxy-4-octoxy-benzophenone Stabilizers from the Salizy.Late group such as octylphenyl salicylate, Nickel chelates, Oxalic acid diamides and sterically hindered piperidine compounds.
Als Phosphite sind Trisnonylphenylphosphit, Trislaurylphosphit oder auch Ester des Pentacrythritphosphite zu nennen.As phosphites are Trisnonylphenylphosphit, Trislaurylphosphit or also to mention esters of pentacrythritol phosphite.
Unter als 5 tabili satoren bekannten Metallverbindungen werden in diesem Zusammenhang verstnden: Calcium-, Barium-, Strontium-, Zink-, Cadmium-, Magnesium-, Aluminium- und Bleiseifen aliphatischer Carbonsäuren oder Oxycarbonsäuren mit etwa 12 bis 32 C-Atomen, Salze der genannten Metalle mit aromatischen Carbonsäuren wie Benzoate oder Salizylate sowie (Alkyl)Phenolate dieser Metalle, ferner Organozinnverbindungen, ie z. B. Dialkylzinnthioglykolate und Carboxylate.Metal compounds known as 5 stabilizers are used in understand this context: calcium, barium, strontium, zinc, cadmium, magnesium, Aluminum and lead soaps of aliphatic carboxylic acids or oxycarboxylic acids with about 12 to 32 carbon atoms, salts of the metals mentioned with aromatic carboxylic acids such as Benzoates or salicylates and (alkyl) phenates of these metals, also organotin compounds, ie z. B. Dialkyltin thioglycolates and carboxylates.
Bekannte Epoxystabilisatoren sind z, B. epoxidierte höhere Fettsäuren wie epoxidiertes Sojabohnenöl, Tallöl, Leinöl oder epoxidiertes Butyloleat sowie Epoxide langkettiger Olefine.Known epoxy stabilizers are, for example, epoxidized higher fatty acids such as epoxidized soybean oil, tall oil, linseed oil or epoxidized butyl oleate as well Long chain olefin epoxides.
Mehrwertige Alkohole können beispielweise Pentaerythrit, Trimethylolpropan, Sorbit oder Mannit sein, d.h. bevorzugt Alkohole mit 5 oder 6 C-Atomen und 3 bis 6 OH-Gruppen.Polyhydric alcohols can, for example, pentaerythritol, trimethylolpropane, Be sorbitol or mannitol, i.e. preferably alcohols with 5 or 6 carbon atoms and 3 to 6 OH groups.
Eine wirksame Stabilisatorkombination für Poly-α-Olefine, wie z. B. Hoch-, Mittel- und Niederdruckpolymerisate von C2- bis C4-α-Olefinen, insbesondere Polyäthylen und Polypropylen oder von Copolymerisaten derartiger α-Olefine beteht, bezogen auf 100 Gew.-Teile Polymer, beispielsweise aus 0,01 bis 5 Gew-Teilen einer der erfindungsgemäß zu verwendenden Verbindungen 0,05 bis 5 Gew.-Teilen eines phenolischen Stabilisators, gregebenenfalls 0,01 bis 5 Gew.-Teilen eines schwefelhaltigen Costabilisators sowie gegebenenfalls 0,01 bis 3 Gew.-Teilen einer basischen oder neutralen Metallseife, wie z. B, Calciumstearat oder Zinkstearat sowie gegebenenfalls 0,1 bis 5 Gew.-Teilen eines Phosphits und gegebenenfalls 0,01 bis 5 Gew.Teilen eines bekannten UV-Stabilisators aus der Gruppe der Alkoxyhydroxybenzophenone, Hydroxyphenylbenzotriazole, Benzylidenmelonsäuremononitrilester oder der sog. Quencher wie Nickelchelate.An effective stabilizer combination for poly-α-olefins such as z. B. High, medium and low pressure polymers of C2 to C4 α-olefins, in particular polyethylene and polypropylene or copolymers of such α-olefins relates, based on 100 parts by weight of polymer, for example from 0.01 to 5 parts by weight one of the compounds to be used according to the invention 0.05 to 5 parts by weight of a phenolic stabilizer, optionally 0.01 to 5 parts by weight of a sulfur-containing Costabilizers and optionally 0.01 to 3 parts by weight of a basic or neutral metal soap, such as B, calcium stearate or zinc stearate and optionally 0.1 to 5 parts by weight of a phosphite and optionally 0.01 to 5 parts by weight of a known UV stabilizer from the group of alkoxyhydroxybenzophenones, Hydroxyphenylbenzotriazoles, Benzylidenmelonsäuremononitrilester or the so-called. Quencher like nickel chelates.
Im folgenden sei anhand einige Beispiele das Verfahren zur Herstellung der neuen Verbindungen erläutert und die hervorragende Wirksamkeit derselben als Lichtschutzmittel für Kunststoffmassen aufgezeigt.In the following, the method of production is given by means of a few examples of the new compounds and the excellent effectiveness of the same as Light stabilizers for plastic masses shown.
Beispiel 1 7-Pentylidenamino- 1 , 3, 5-triazaadamantan 30,8 g (0,2 Mol) 7-Amino-1,3,5-triazaadamantan und 17,2 g (0,2 Mol) Valeraldehyd werden in 150 ml Toluol vorgelegt. Dazu gibt man 0,2 g p-Toluolsulfonsäure und kocht das Substanzgemisch unter Rühren am Wasserabscheider. Nach Beendigung der Wasserabscheidung läßt man abkülen, nutscht ab und kristallisiert aus Heptan um. Weiße Irristalle vom Fp. 122 °C. Ausbeute 60 % der Theorie.Example 1 7-Pentylideneamino-1, 3, 5-triazaadamantane 30.8 g (0.2 Mol) 7-amino-1,3,5-triazaadamantane and 17.2 g (0.2 mol) valeraldehyde are in 150 ml of toluene submitted. 0.2 g of p-toluenesulfonic acid are added and the mixture of substances is boiled while stirring on the water separator. After the separation of water has ended, the mixture is left Rinse, siphon and recrystallize from heptane. White irrystals of m.p. 122 ° C. Yield 60% of theory.
-Beispiele 2 bis 8 Analog Beispiel 1 wurden hergestellt:
100 Gew.-Teile Polypropylen mit einem Schmelzindex i5 von ca.100 parts by weight polypropylene with a melt index i5 of approx.
6 g/10 Min. (bestimmt nach ASTM D 1238-62 T) und einer Dichte von 0,96 wurden mit 0,10 Gew.-Teilen Pentacrythrityltetrakis [3-(3,5-di-tbutyl-4-hydroxyphenyl)-propionat] 0,20 Gew.-Teilen Calciumstearat und 0,30 Gew.-Teilen einer der erfindungsgemäßen Verbindungen vermischt und auf der Zweiwalze bei 200 °C fünf Minuten lang homogenisiert. Die Kunststoffschmelze wurde sodann bei 200 °C zu einer Platze von 1 mm Dicke gepreßt. Aus der erkalteten Platte wurden Prüfkörper nach DIN 53 455 ausgestanzt. Die als Vergleichsmuster benötigten Prüfkörper wurden analog, jedoch unter Fertlassen des zu testenden Stabilisators, herstellt.6 g / 10 min. (Determined according to ASTM D 1238-62 T) and a density of 0.96 were with 0.10 parts by weight of pentacrythrityl tetrakis [3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate] 0.20 part by weight of calcium stearate and 0.30 part by weight of one of the invention Compounds mixed and homogenized on the two-roller at 200 ° C for five minutes. The plastic melt was then pressed at 200 ° C. to form a square 1 mm thick. Test specimens in accordance with DIN 53 455 were punched out of the cooled plate. As Test specimens required for comparison samples were carried out in the same way, but with the stabilizer to be tested.
Zur Bestimmung der Lichtstabilität wurden die Proben in einer Nenotest-150-Apparatur der Firma Original Hanau Quarzlampen GmbH der Bestrahlung mit Wechsellicht unterworfen. Die Strahlungsintensität wurde durch 6 IR-Fenster und 1 UV-Fenster (DIN 53 387) moduliert. Gemessen wurde die Belichtungszeit in Stunden (= Standzeit), nach welcher die absolute Reißdehnung auf 10 % abgesunken war. Die Reßdehnung wurde auf einer Zugprüfmaschine der Firma Instron bei einer Abzugsgeschwindigkeit von 5 cm/Min. ermittelt.To determine the light stability, the samples were placed in a Nenotest 150 apparatus the company Original Hanau Quarzlampen GmbH subjected to irradiation with alternating light. The radiation intensity was determined by 6 IR windows and 1 UV window (DIN 53 387) modulated. The exposure time was measured in hours (= standing time) after which the absolute elongation at break had dropped to 10%. The elongation at break was on a Tensile testing machine from Instron at a take-off speed of 5 cm / min. determined.
Die Ausgangsreißdehnung betrug 950 %.The initial elongation at break was 950%.
Nach einer Belichtungszeit von 600 Stunden wurden folgende Reißdehnungswerte
gemessen:
Claims (7)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762637193 DE2637193A1 (en) | 1976-08-18 | 1976-08-18 | (7)-Amino-(1,3,5)-tri:aza-adamantane derivs. - used as stabilisers for organic polymer, esp. against UV irradiation and heat |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762637193 DE2637193A1 (en) | 1976-08-18 | 1976-08-18 | (7)-Amino-(1,3,5)-tri:aza-adamantane derivs. - used as stabilisers for organic polymer, esp. against UV irradiation and heat |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2637193A1 true DE2637193A1 (en) | 1978-02-23 |
Family
ID=5985751
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762637193 Withdrawn DE2637193A1 (en) | 1976-08-18 | 1976-08-18 | (7)-Amino-(1,3,5)-tri:aza-adamantane derivs. - used as stabilisers for organic polymer, esp. against UV irradiation and heat |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2637193A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL1009844C2 (en) * | 1998-08-12 | 2000-02-15 | Dsm Nv | Plastic composition with improved weather resistance. |
-
1976
- 1976-08-18 DE DE19762637193 patent/DE2637193A1/en not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL1009844C2 (en) * | 1998-08-12 | 2000-02-15 | Dsm Nv | Plastic composition with improved weather resistance. |
| WO2000009604A1 (en) * | 1998-08-12 | 2000-02-24 | Dsm N.V. | Plastic composition with improved weather resistance |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2606026C2 (en) | 1-Oxa-3,8-diaza-spiro- [4,5] -decanes, their preparation and their use as light stabilizers | |
| EP0024338B1 (en) | Triazine derivatives, their preparation and their use as stabilising agents for synthetic polymers | |
| EP0028318B1 (en) | Ethers based on polyalkyl-1-oxa-diazaspirodecanes, their preparation, their use and synthetic polymers stabilized therewith | |
| EP0029522B1 (en) | S-triazine derivatives, processes for their preparation from halotriazinylamines and polyamines, and their use as stabilizers | |
| DE2545292C3 (en) | Azaadamantane compounds as stabilizers for organic polymer compositions | |
| EP0057885B1 (en) | Substituted diazaspirodecanes, their preparation and their use for the stabilisation of organic polymers and these stabilised polymers | |
| EP0025867B1 (en) | Alkylated diazaspirodecanes, their preparation and their use as light stabilisers | |
| EP0044499B1 (en) | Triazinylaminotriazines, their preparation, their use in stabilising synthetic polymers and products realised with them | |
| DE2634957A1 (en) | NEW 1-OXA-4.8-DIAZA-SPIRO-ANGLE CLAMP ON 4.5-ANGLE CLAMP TO -DECANE, THEIR PRODUCTION AND THEIR USE AS LIGHT PROTECTION | |
| EP0008084B1 (en) | Novel urea derivatives, their preparation and their use as light stabilizer for polymers | |
| DE2742582C2 (en) | ||
| EP0001207B1 (en) | Urea derivatives, their preparation and their use as light stabilisers | |
| DE2637193A1 (en) | (7)-Amino-(1,3,5)-tri:aza-adamantane derivs. - used as stabilisers for organic polymer, esp. against UV irradiation and heat | |
| US4104251A (en) | Substituted tetraalkylpiperidone-4-oximes | |
| DE602005000555T2 (en) | Thermal stabilizer compositions for halogen-containing vinyl polymers | |
| DE2606819A1 (en) | 14 SUBSTITUTED 7.15 DIAZADISPIRO ANGULAR CLAMP ON 5.1.5.3 ANGULAR CLAMP FOR -HEXADECANES AS UV STABILIZERS | |
| DE2616799A1 (en) | SUBSTITUTED TRIAZAADAMANTANE COMPOUNDS, THEIR PRODUCTION AND USE | |
| EP0009161B1 (en) | Polyalkylpiperidine-formaldehyde polymers, process for their preparation and their use | |
| EP0253773B1 (en) | Stabilized synthetic polymer | |
| CH641465A5 (en) | 1-Oxa-4,8-diaza-spiro[4,5]decanes | |
| DE2602673A1 (en) | PIPERIDINE HYDROXYAMIDES, THEIR PRODUCTION AND USE | |
| DE2505152C2 (en) | ACETACETIC ACID PENTAERYTHRITE PHOSPHITESTER, METHOD FOR ITS MANUFACTURING AND ITS USE | |
| DE3800294A1 (en) | Urethane derivatives of hindered phenol alcohols and organic material stabilised therewith | |
| DE2920615A1 (en) | Poly:alkyl-piperidine carboxylate and carbamate ester cpds. - useful as synthetic polymer UV stabilisers |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |