JPH0132223B2 - - Google Patents
Info
- Publication number
- JPH0132223B2 JPH0132223B2 JP3631382A JP3631382A JPH0132223B2 JP H0132223 B2 JPH0132223 B2 JP H0132223B2 JP 3631382 A JP3631382 A JP 3631382A JP 3631382 A JP3631382 A JP 3631382A JP H0132223 B2 JPH0132223 B2 JP H0132223B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- bis
- copolymer
- hydroxyethyl
- tetramethyl
- 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.)
- Expired
Links
- -1 bis(2-hydroxyethyl)aminotriazine compound Chemical class 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 description 26
- 229920001577 copolymer Polymers 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000003381 stabilizer Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 229920003002 synthetic resin Polymers 0.000 description 7
- 239000000057 synthetic resin Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 239000004611 light stabiliser Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-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
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- 150000003918 triazines Chemical class 0.000 description 4
- VDVUCLWJZJHFAV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1 VDVUCLWJZJHFAV-UHFFFAOYSA-N 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- IHDBZCJYSHDCKF-UHFFFAOYSA-N 4,6-dichlorotriazine Chemical compound ClC1=CC(Cl)=NN=N1 IHDBZCJYSHDCKF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000004088 foaming agent Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 150000002605 large molecules Chemical class 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 2
- 229920003067 (meth)acrylic acid ester copolymer Polymers 0.000 description 1
- QKUFMUWMMWFBFB-UHFFFAOYSA-N 1,2,2,3,3-pentamethylpiperidin-4-amine Chemical compound CN1CCC(N)C(C)(C)C1(C)C QKUFMUWMMWFBFB-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- HIAUUZIAFGDOBJ-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-octylpiperidin-4-ol Chemical compound CCCCCCCCN1C(C)(C)CC(O)CC1(C)C HIAUUZIAFGDOBJ-UHFFFAOYSA-N 0.000 description 1
- RNLLZPURKGALKR-UHFFFAOYSA-N 2-[(4,6-dichloro-1h-triazin-2-yl)-(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(CCO)N1NC(Cl)=CC(Cl)=N1 RNLLZPURKGALKR-UHFFFAOYSA-N 0.000 description 1
- WQDBUDHEWXLHSA-UHFFFAOYSA-N 2-tert-butyl-4-[1-(3-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-3-methylphenol Chemical compound C=1C=C(O)C(C(C)(C)C)=C(C)C=1C(CCC)C1=CC=C(O)C(C(C)(C)C)=C1C WQDBUDHEWXLHSA-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical group CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- IVRFYNSETZKRSJ-UHFFFAOYSA-N ClC=C.N#CC=CC=CC1=CC=CC=C1 Chemical compound ClC=C.N#CC=CC=CC1=CC=CC=C1 IVRFYNSETZKRSJ-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 1
- 239000003508 Dilauryl thiodipropionate Substances 0.000 description 1
- 239000002656 Distearyl thiodipropionate Substances 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 229920012485 Plasticized Polyvinyl chloride Polymers 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 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
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- SXXILWLQSQDLDL-UHFFFAOYSA-N bis(8-methylnonyl) phenyl phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OC1=CC=CC=C1 SXXILWLQSQDLDL-UHFFFAOYSA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- ZJPJECQPVMSILT-UHFFFAOYSA-N chloroethene 3-(2-phenylethenyl)furan-2,5-dione Chemical compound ClC=C.O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 ZJPJECQPVMSILT-UHFFFAOYSA-N 0.000 description 1
- IEJNAGSUKYCWCR-UHFFFAOYSA-N chloroethene;1,1-dichloroethene;ethenyl acetate Chemical compound ClC=C.ClC(Cl)=C.CC(=O)OC=C IEJNAGSUKYCWCR-UHFFFAOYSA-N 0.000 description 1
- VSJDEWYENWWMAV-UHFFFAOYSA-N chloroethene;2-methylprop-2-enoic acid Chemical compound ClC=C.CC(=C)C(O)=O VSJDEWYENWWMAV-UHFFFAOYSA-N 0.000 description 1
- KRGNPJFAKZHQPS-UHFFFAOYSA-N chloroethene;ethene Chemical group C=C.ClC=C KRGNPJFAKZHQPS-UHFFFAOYSA-N 0.000 description 1
- SQNNHEYXAJPPKH-UHFFFAOYSA-N chloroethene;prop-2-enoic acid Chemical compound ClC=C.OC(=O)C=C SQNNHEYXAJPPKH-UHFFFAOYSA-N 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 229920003020 cross-linked polyethylene Polymers 0.000 description 1
- 239000004703 cross-linked polyethylene Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 235000019304 dilauryl thiodipropionate Nutrition 0.000 description 1
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
- 235000019305 distearyl thiodipropionate Nutrition 0.000 description 1
- 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 1
- 238000001035 drying Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 239000004794 expanded polystyrene Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 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 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229920003049 isoprene rubber Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920005671 poly(vinyl chloride-propylene) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 238000004262 preparative liquid chromatography Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
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The present invention relates to a bis(2-hydroxyethyl)aminotriazine compound having a 2,2,6,6-tetramethylpiperidyl group, which is useful as a light stabilizer for synthetic resins and an intermediate thereof. Triazine compounds having a 2,2,6,6-tetramethylpiperidyl group are useful compounds as light stabilizers for organic materials such as synthetic resins, and a large number of these compounds have been known. For example, Tokukai Akira
49-21389 describes that triazine compounds having a structure similar to the compound used in the present invention are useful as light stabilizers for organic materials. However, when these compounds are used as light stabilizers for synthetic resins, their effects are not sufficient, and they have the disadvantage that their effects are significantly reduced, especially after high-temperature processing, and further improvements are needed. It was hot. For this reason, various proposals have been made to increase the molecular weight of triazine compounds having a 2,2,6,6-tetramethylpiperidyl group. For example, JP-A-52-
No. 71786, JP-A-52-73886, JP-A-53-67749
No., JP-A-54-106483, JP-A-54-126249,
JP-A-55-98180, JP-A-55-102637, JP-A-55-104279, JP-A-56-4639, JP-A-56-
30974 and Japanese Patent Application Laid-open No. 56-75488,
A high molecular weight compound in which a triazine compound having a 2,2,6,6-tetramethylpiperidyl group is bonded with a polyamine, polyalcohol, or polyepoxy compound has been proposed. However, many of these high molecular weight compounds are difficult to manufacture and have poor compatibility with synthetic resins, causing bloom or bleed.
Moreover, the effect was not satisfactory. As a result of repeated studies on triazine compounds having a tetramethylpiperidyl group, the present inventors found that the compound represented by the following general formula () has particularly excellent effects as a stabilizer for synthetic resins, and also It has been found that the stabilizing ability does not decrease even when It has also been found that the compound represented by the following general formula () has two hydroxyl groups and is therefore extremely useful as a reactive stabilizer for polyurethane. (In the formula, R 1 represents a hydrogen atom, oxyl or an alkyl group, and X represents a group CHâO,
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ãžã¯ããâããªã¢ãžã³ãšã[Formula] is shown. R 2 represents a hydrogen atom or an alkyl group, and R 3 represents a lower alkyl group. ) The compound of the present invention represented by the above general formula () will be explained in detail below. In the above general formula (), the alkyl groups represented by R 1 and R 2 include methyl, ethyl, propyl, butyl, amyl, hexyl, octyl, 2
- Examples include those having 1 to 18 carbon atoms, such as ethylhexyl, decyl, dodecyl, octadecyl, 2-hydroxyethyl, 2-hydroxypropyl, 2-hydroxybutyl, and phenylmethyl. Examples of the lower alkyl group represented by R3 include those having 1 to 4 carbon atoms, such as methyl, ethyl, propyl, and butyl. The bis(2-hydroxyethyl)aminotriazine compound of the present invention is obtained, for example, by the reaction of cyanuric chloride with diethanolamine.
Bis(2-hydroxyethyl)amino-4,6-
dichloro-triazine and
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It can be easily produced by reacting a piperidine compound represented by the formula in the presence of a base. In addition, bis(2-hydroxyethyl) of the present invention
The aminotriazine compound can also be produced by reacting cyanuric chloride with 2 moles of a piperidine compound and then reacting with diethanolamine, or by simultaneously reacting 1 mole of diethanolamine with 2 moles of a piperidine compound. Representative examples of the compounds of the present invention represented by the general formula () are shown in Table 1 below. In addition, in the table,
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ãã®çµæãè¡šâïŒã«ç€ºãã[Formula] is shown. The present invention will be explained in more detail below with reference to Examples. Example 1 2-bis(2-hydroxyethyl)amino-
4,6-bis(2,2,6,6-tetramethyl-
4-piperidylamino)triazine (No. 1 in Table 1)
1 compound). 2-bis(2-hydroxyethyl)amino-
4,6-dichlorotriazine 5.4g, 2,2,6,
6-tetramethyl-4-aminopiperidine 7.0g,
Take 2.3g of sodium carbonate and 60ml of toluene,
The mixture was stirred under reflux in a nitrogen stream for 40 hours. The reaction mixture was filtered, and the filtered residue was added to 85 ml of a 2% NaOH aqueous solution and stirred for 30 minutes, followed by filtering, washing with water, and drying. The obtained product was dissolved in tetrahydrofuran, and insoluble materials were separated. The liquid was removed under reduced pressure to obtain a white powder product with a melting point of 115-120°C. Elemental analysis C% H% N% Calculated value 60.98 9.76 22.76 Actual value 60.83 9.77 22.85 Example 2 2-bis(2-hydroxyethyl)amino-
4,6-bis(N-butyl-N-2,2,6,6
-Tetramethyl-4-piperidylamino)-triazine (Compound No. 2 in Table 1). 2-bis(2-hydroxyethyl)amino-
Take 1.8 g of 4,6-dichlorotriazine, 3.2 g of N-butyl-N-2,2,6,6-tetramethyl-4-piperidylamine, 0.8 g of sodium carbonate, and 20 ml of toluene, and reflux in a nitrogen atmosphere. Stirred for 20 hours. Filter the reaction mixture and remove 2%
It was added to 30 ml of NaOH aqueous solution and stirred for 30 minutes. The obtained product was separated, washed with water, dried, and then recrystallized from a methanol/acetone mixed solvent to give a melting point of 280.
The product was obtained as a white powder with a temperature above .degree. Elemental analysis C% H% N% Calculated value 65.56 10.60 18.54 Actual value 65.70 10.55 18.43 Example 3 2-bis(2-hydroxyethyl)amino-
4,6-bis(1,2,2,6,6-pentamethyl-4-piperidylamino)triazine (Table 1
No. 3 compound). 1,2,2,6,6- instead of 7.0 g of 2,2,6,6-tetramethyl-4-aminopiperidine
The same procedure as in Example 1 was carried out except that 7.6 g of pentamethyl-4-aminopiperidine was used, and the melting point was 137 to 145.
The product was obtained as a white powder at . Elemental analysis C% H% N% Calculated value 62.31 10.00 21.54 Actual value 62.43 9.93 21.50 Example 4 2-bis(2-hydroxyethyl)amino-
4,6-bis(2,2,6,6-tetramethyl-
4-piperidyloxy)triazine (No. 1 in Table 1)
4 compound). Sodium 1.4g, 2,2,6,6-tetramethyl-4-piperidinol 6.3g and toluene 100g
ml was taken and stirred under reflux for 24 hours. Add 2-bis(2-hydroxyethyl)-4,6 to the cooled solution.
- 5.0 g of dichlorotriazine was added, and the mixture was stirred under reflux for 8 hours. After separating the reaction mixture, it was added to 90 ml of 2% aqueous sodium hydroxide solution and stirred for 30 minutes. The obtained product was separated, washed with water, dried, and then recrystallized from ethyl acetate to obtain a white powder product with a melting point of 103-107°C. Elemental analysis C% H% N% Calculated value 60.73 9.31 17.00 Actual value 60.79 9.33 16.87 Example 5 2-bis(2-hydroxyethyl)amino-
4,6-bis(1-oxyl-2,2,6,6-
Production of tetramethyl-4-piperidyloxy)triazine (Compound No. 5 in Table 1). Same as Example 4 except that 6.9 g of 2,2,6,6-tetramethyl-4-hydroxypiperidine-1-oxyl was used instead of 6.3 g of 2,2,6,6-tetramethyl-4-piperidinol. Similarly,
The product was obtained as a light orange powder with a melting point of 97-102°C. Elemental analysis C% H% N% Calculated value 57.25 8.40 16.03 Actual value 57.17 8.42 16.09 Example 6 2-bis(2-hydroxyethyl)amino-
4,6-bis(1-octyl-2,2,6,6-
Production of tetramethyl-4-piperidyloxy)triazine (Compound No. 6 in Table 1). Instead of 6.3 g of 2,2,6,6-tetramethyl-4-piperidinol, 1-octyl-2,2,
6,6-tetramethyl-4-piperidinol 10.8
A white waxy solid product was obtained in the same manner as in Example 4 except that g was used. Elemental analysis C% H% N% Calculated value 68.52 10.86 11.70 Actual value 68.40 10.84 11.75 Example 7 2-bis(2-hydroxyethyl)amino-
4,6-bis(9-aza-3-ethyl-8,8,
Production of 10,10-tetramethyl-1,5-dioxaspiro[5,5]-3-undecylmethoxy)triazine (Compound No. 7 in Table 1). Dianuric chloride 0.93g, 9-aza-3-ethyl-
3.4 g of 3-hydroxymethyl-8,8,10,10-tetramethyl-1,5-dioxaspiro[5.5]undecane, 0.44 g of sodium hydroxide and 30 ml of toluene were taken and stirred under reflux for 24 hours. After cooling, diethanolamine 0.58g and sodium hydroxide
0.22 g was added, and the mixture was further stirred under reflux for 15 hours. The reaction mixture was washed with water, dried, and the solvent was removed. The obtained product was purified by preparative liquid chromatography to obtain a glassy solid product. Elemental analysis C% H% N% Calculated value 61.50 9.14 11.63 Actual value 61.73 9.21 11.48 Example 8 2-bis(2-hydroxyethyl)amino-
4,6-bis(9-aza-3-ethyl-8,8,
Production of 9,10,10-pentamethyl-1,5-dioxaspiro[5.5]-3-undecylmethoxy)triazine (Compound No. 8 in Table 1). 9-aza-3-ethyl-3-hydroxymethyl-8,8,10,10-tetramethyl-1,5-dioxaspiro[5.5] instead of 3.4 g of undecane, 9
-Aza-3-ethyl-3-hydroxymethyl-
A glassy solid product was obtained in the same manner as in Example 7, except that 3.6 g of 8,8,9,10,10-pentamethyl-1,5-dioxaspiro[5,5]undecane was used. Elemental analysis C% H% N% Calculated value 62.40 9.33 11.20 Actual value 62.53 9.27 11.09 The compound of the present invention is extremely useful as a stabilizer for organic materials such as synthetic resins. Organic materials stabilized by the compounds of the present invention include, for example, α-olefin polymers such as low-density and high-density polyethylene, polypropylene, polybutene, poly-3-methylbutene, or ethylene-vinyl acetate copolymers. , polyolefins such as ethylene-propylene copolymer, ethylene-butene-1 copolymer, and copolymers thereof,
Polyvinyl chloride, polyvinyl bromide, polyvinyl fluoride, polyvinylidene chloride, chlorinated polyethylene, chlorinated polypropylene, polyvinylidene fluoride, brominated polyethylene, chlorinated rubber, vinyl chloride-vinyl acetate copolymer, vinyl chloride-ethylene copolymer Polymer, vinyl chloride-propylene copolymer, vinyl chloride-styrene copolymer, vinyl chloride-isobutylene copolymer, vinyl chloride-vinylidene chloride copolymer, vinyl chloride-styrene-maleic anhydride terpolymer, Vinyl chloride-styrene-acrylonitrile copolymer, vinyl chloride-butadiene copolymer, vinyl chloride-isoprene copolymer, vinyl chloride-chlorinated propylene copolymer, vinyl chloride-vinylidene chloride-vinyl acetate terpolymer, Vinyl chloride-acrylic acid ester copolymer, vinyl chloride-maleic acid ester copolymer, vinyl chloride-methacrylic acid ester copolymer, vinyl chloride-
Acrylonitrile copolymers, halogen-containing synthetic resins such as internally plasticized polyvinyl chloride, petroleum resins, coumaron resins, polystyrene, polyvinyl acetate, acrylic resins, styrene and other monomers (e.g. maleic anhydride, butadiene, acrylonitrile, etc.) ), acrylonitrile-butadiene-styrene copolymer, acrylic ester-butadiene-styrene copolymer, methacrylic ester-butadiene-styrene copolymer, methacrylate resin such as polymethyl methacrylate, polyvinyl alcohol, polyvinyl Formal, polyvinyl butyral, linear polyester, polyphenylene oxide, polyamide, polycarbonate, polyacetal, polyurethane, cellulose resin, phenol resin, urea resin, melamine resin, epoxy resin, unsaturated polyester resin, silicone resin, etc. be able to.
Furthermore, isoprene rubber, butadiene rubber, acrylonitrile-butadiene copolymer rubber, styrene-
Rubbers such as butadiene copolymer rubber or blends of these resins may also be used. Also included are crosslinked polymers such as crosslinked polyethylene crosslinked by peroxide or radiation, and foamed polymers such as expanded polystyrene foamed with a foaming agent. In addition, oils and fats, fragrances, mineral oil, soaps, creams,
Natural and synthetic waxes, synthetic ester-based oils are also stabilized by the addition of the compounds of the invention. When the compound of the present invention is added to an organic material, the amount added is 0.001 to 10% by weight, preferably 0.01 to 3% by weight, based on the organic material. In addition to the compound of the present invention, if necessary, a phenolic antioxidant, a thioether antioxidant, an organic phosphite compound, an ultraviolet absorber, a heavy metal deactivator, a nucleating agent, a metallic soap, an organic tin compound, and a plasticizer are added. , epoxy compounds, pigments, fillers,
Foaming agents, antistatic agents, flame retardants, lubricants, processing aids, etc. can be added in combination. Next, the effect of the compound of the present invention as a light stabilizer will be specifically explained with reference to the following examples. Example 9 Polypropylene 100 parts by weight Stearyl-β-3,5-di-tert-butyl-4
-Hydroxyphenylpropionate
0.2 Stabilizer (Table 2) 0.3 A press sheet with a thickness of 0.3 mm was prepared using the above formulation, and a light resistance test was conducted using a high-pressure mercury lamp. A light resistance test was also conducted on the sheet after being irradiated with light for 100 hours and immersed in hot water at 80°C for 15 hours.
The results are shown in Table-2.
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å®å®å€ïŒè¡šâïŒïŒ 0.2 [Table] Example 10 It is known that ordinary stabilizers lose their effectiveness significantly due to volatilization, decomposition, etc. during high-temperature processing of resins. In this example, the effect of high-temperature processing was confirmed by repeatedly performing extrusion processing. After mixing the resin and additives in a mixer for 5 minutes according to the following formulation, a compound was prepared using an extruder. After extrusion was repeated five times (cylinder temperature: 230°C, 240°C, head die temperature: 250°C, rotation speed: 20 rpm), a test piece was made using an injection molding machine using this compound. (Cylinder temperature
240° C., nozzle temperature 250° C., injection pressure 475 Kg/cm 2 ) Using the obtained test piece, a light resistance test was conducted using a high-pressure mercury lamp. In addition, the same test was conducted for a sample that had been extruded once. The results are shown in Table-3. <Composition> Ethylene-propylene copolymer resin 100 parts by weight Calcium stearate 0.2 parts by weight Stearyl-β-3,5-di-tert-butyl-4
-Hydroxyphenylpropionate
0.1 Dilaurylthiodipropionate 0.2 Stabilizer (Table-3) 0.2
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ã枬å®ããããã®çµæãè¡šâïŒã«ç€ºãã[Table] Example 11 Polyethylene 100 parts by weight Ca-stearate 1.0 Tetrakis [methylene-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] Methane 0.1 Distearylthiodipropionate 0.3 Stable Agent (Table 4) 0.2 The above mixture was kneaded and pressed to form a sheet with a thickness of 0.5 mm. Using this sheet, the light resistance was measured in a weatherometer, and the time until it became brittle was measured. The results are shown in Table 4.
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ãããã®çµæãè¡šâïŒã«ç€ºãã[Table] Example 12 ABS resin 100 parts by weight 4,4'-butylidene bis(2-tert-butyl-m
-Cresol) 0.1 Stabilizer (Table-5) 0.3 Roll knead the above mixture and press it to a thickness of 3 mm.
A sheet was created. Using this sheet, the residual tensile strength after 800 hours of irradiation was measured using a weatherometer. The results are shown in Table-5.
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0.1 Ca-stearate 0.1 Zn-stearate 0.1 Diisodecyl phenyl phosphite 0.2 Stabilizer (Table 6) 0.2 After kneading the above mixture on a roll at 130â, press it at 140â to form a sheet with a thickness of 0.4mm. Created. The residual tensile strength of this sheet was measured after 500 hours of irradiation in a weatherometer. The results are shown in Table-6.
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ïŒã«ç€ºãã[Table] Example 14 Polyvinyl chloride 100 parts by weight Dioctyl phthalate 48 Epoxidized soybean oil 2 Trisnonylphenyl phosphite 0.2 Ca-stearate 1.0 Zn-stearate 0.1 Stabilizer (Table 7) 0.3 Roll the above mixture A sheet with a thickness of 1 mm was prepared by kneading the mixture above. Using this sheet, a light resistance test was conducted in a weatherometer. Display the results.
7.
ãè¡šã
å®æœäŸ 15
ååé2000ã®ããªããã©ã¡ãã¬ã³ãšãŒãã«ã°ãª
ã³ãŒã«100.0ïœïŒ0.05ã¢ã«ïŒãã¯ãããã³ãŒã³150
mlã«æº¶è§£ãããžããšãã«ã¡ã¿ã³ãžã€ãœã·ã¢ããŒã
20.0ïœïŒ0.08ã¢ã«ïŒãå ãã120âã§30åéåå¿
ãããããã®åŸãïŒïŒïŒâããã¬ã³ã°ãªã³ãŒã«
2.25ïœïŒ0.025ã¢ã«ïŒåã³è¡šâïŒã«èšèŒã®å®å®å€
0.005ã¢ã«ãå ã110âã§ïŒæéåå¿ããããåŸã
ãã溶液ãéåžžã®æ¹æ³ã«ãã也åŒçŽ¡ç³žããŠã40ã
ããŒã«ã®åŒŸæ§ç³žãåŸããå°ãæ¯èŒäŸ15âïŒåã³15
âïŒã«ãããŠã¯ïŒïŒïŒâããã¬ã³ã°ãªã³ãŒã«2.7
ïœïŒ0.03ã¢ã«ïŒãçšãã玡糞åã«å®å®å€0.005ã¢
ã«ãæ·»å ããã
åŸããã匟æ§ç³žãçšããããšãŒãã¡ãŒã¿ãŒã§72
æéç
§å°åŸã®äŒžã³æ®çã枬å®ããããŸãåå¡©åç
çŽ ã§ïŒæéæœåºãã匟æ§ç³žã«ã€ããŠãåæ§ã«è©Šéš
ããããã®çµæã次ã®è¡šâïŒã«ç€ºãã[Table] Example 15 100.0 g (0.05 mol) of polytetramethylene ether glycol with a molecular weight of 2000 was mixed with 150 g of chlorobenzene.
Diphenylmethane diisocyanate dissolved in ml
20.0g (0.08mol) was added and reacted at 120°C for 30 minutes. Then 1,4-butylene glycol
2.25g (0.025mol) and the stabilizer listed in Table 8
0.005 mol was added and reacted at 110°C for 2 hours. The resulting solution was dry-spun using a conventional method to obtain a 40-denier elastic yarn. Furthermore, Comparative Examples 15-1 and 15
-2 is 1,4-butylene glycol 2.7
g (0.03 mol) and 0.005 mol of stabilizer was added before spinning. Using the obtained elastic yarn, 72 on the fade meter
The residual elongation rate after time irradiation was measured. Elastic threads extracted with carbon tetrachloride for 2 hours were also tested in the same manner. The results are shown in Table 8 below.
ãè¡šããtableã
Claims (1)
ãããã·ãšãã«ïŒã¢ããããªã¢ãžã³ååç©ã ïŒåŒäžãR1ã¯æ°ŽçŽ ååããªãã·ã«ãŸãã¯ã¢ã«
ãã«åºã瀺ããã¯åºCHââã
ãåŒããŸãã¯ãåŒãã 瀺ããR2ã¯æ°ŽçŽ ååãŸãã¯ã¢ã«ãã«åºã瀺ãã
R3ã¯äœçŽã¢ã«ãã«åºã瀺ããïŒ[Scope of Claims] 1. A bis(2-hydroxyethyl)aminotriazine compound represented by the following general formula (). (In the formula, R 1 represents a hydrogen atom, oxyl or an alkyl group, and X represents a group CHâOâ,
Indicates [formula] or [formula]. R 2 represents a hydrogen atom or an alkyl group,
R 3 represents a lower alkyl group. )
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3631382A JPS58152881A (en) | 1982-03-08 | 1982-03-08 | Bis(2-hydroxyethyl)aminotriazine compound |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3631382A JPS58152881A (en) | 1982-03-08 | 1982-03-08 | Bis(2-hydroxyethyl)aminotriazine compound |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS58152881A JPS58152881A (en) | 1983-09-10 |
JPH0132223B2 true JPH0132223B2 (en) | 1989-06-29 |
Family
ID=12466346
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP3631382A Granted JPS58152881A (en) | 1982-03-08 | 1982-03-08 | Bis(2-hydroxyethyl)aminotriazine compound |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS58152881A (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5216156A (en) * | 1992-05-05 | 1993-06-01 | Ciba-Geigy Corporation | Non-migrating 1-hydrocarbyloxy-2,2,6,6-tetramethylpiperidine 1,3,5-triazine derivatives |
IT201700078234A1 (en) | 2017-07-11 | 2019-01-11 | 3V Sigma Spa | IMPEDINE MINES |
-
1982
- 1982-03-08 JP JP3631382A patent/JPS58152881A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS58152881A (en) | 1983-09-10 |
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