JPH0262563B2 - - Google Patents
Info
- Publication number
- JPH0262563B2 JPH0262563B2 JP19580282A JP19580282A JPH0262563B2 JP H0262563 B2 JPH0262563 B2 JP H0262563B2 JP 19580282 A JP19580282 A JP 19580282A JP 19580282 A JP19580282 A JP 19580282A JP H0262563 B2 JPH0262563 B2 JP H0262563B2
- Authority
- JP
- Japan
- Prior art keywords
- samarium
- carbon atoms
- methacrylic resin
- resin composition
- saturated
- 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
- 239000000203 mixture Substances 0.000 claims description 33
- 239000000113 methacrylic resin Substances 0.000 claims description 22
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical group [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 claims description 20
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 19
- 150000003317 samarium compounds Chemical class 0.000 claims description 19
- 238000006116 polymerization reaction Methods 0.000 claims description 18
- 229910052772 Samarium Inorganic materials 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 239000011347 resin Substances 0.000 claims description 13
- 229920005989 resin Polymers 0.000 claims description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 229910001954 samarium oxide Inorganic materials 0.000 claims description 11
- FKTOIHSPIPYAPE-UHFFFAOYSA-N samarium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[Sm+3].[Sm+3] FKTOIHSPIPYAPE-UHFFFAOYSA-N 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 10
- 239000002994 raw material Substances 0.000 claims description 10
- 229940075630 samarium oxide Drugs 0.000 claims description 10
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 9
- 239000007983 Tris buffer Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- YZDZYSPAJSPJQJ-UHFFFAOYSA-N samarium(3+);trinitrate Chemical compound [Sm+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O YZDZYSPAJSPJQJ-UHFFFAOYSA-N 0.000 claims description 7
- OIUWEEPWAUVTRR-UHFFFAOYSA-K 2-methylprop-2-enoate samarium(3+) Chemical compound C(C(=C)C)(=O)[O-].[Sm+3].C(C(=C)C)(=O)[O-].C(C(=C)C)(=O)[O-] OIUWEEPWAUVTRR-UHFFFAOYSA-K 0.000 claims description 6
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 150000001216 Samarium Chemical class 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical group CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 4
- QCZFMLDHLOYOQJ-UHFFFAOYSA-H samarium(3+);tricarbonate Chemical compound [Sm+3].[Sm+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O QCZFMLDHLOYOQJ-UHFFFAOYSA-H 0.000 claims description 4
- BCYBEIXXOVNETJ-UHFFFAOYSA-K samarium(3+);trihydroxide Chemical compound [OH-].[OH-].[OH-].[Sm+3] BCYBEIXXOVNETJ-UHFFFAOYSA-K 0.000 claims description 4
- XSJMDIJOWQAYQH-UHFFFAOYSA-K C(C=C)(=O)[O-].[Sm+3].C(C=C)(=O)[O-].C(C=C)(=O)[O-] Chemical compound C(C=C)(=O)[O-].[Sm+3].C(C=C)(=O)[O-].C(C=C)(=O)[O-] XSJMDIJOWQAYQH-UHFFFAOYSA-K 0.000 claims description 3
- 239000003505 polymerization initiator Substances 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 6
- 125000005595 acetylacetonate group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 8
- 230000003287 optical effect Effects 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 239000011342 resin composition Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 6
- 230000005855 radiation Effects 0.000 description 6
- 239000006082 mold release agent Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 150000007522 mineralic acids Chemical class 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- -1 polyethylene Polymers 0.000 description 4
- 239000002685 polymerization catalyst Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 2
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 150000001639 boron compounds Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 150000002611 lead compounds Chemical class 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- PFHOSZAOXCYAGJ-UHFFFAOYSA-N 2-[(2-cyano-4-methoxy-4-methylpentan-2-yl)diazenyl]-4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)(C)OC PFHOSZAOXCYAGJ-UHFFFAOYSA-N 0.000 description 1
- QUASZQPLPKGIJY-UHFFFAOYSA-N 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound OCCOCCOCCOCCOC(=O)C=C QUASZQPLPKGIJY-UHFFFAOYSA-N 0.000 description 1
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- QXFADXLALKKHIZ-UHFFFAOYSA-N 2-octylbenzoic acid Chemical compound CCCCCCCCC1=CC=CC=C1C(O)=O QXFADXLALKKHIZ-UHFFFAOYSA-N 0.000 description 1
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- 229920005509 ACRYPET® VH Polymers 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 239000007779 soft material Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005341 toughened glass Substances 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
Landscapes
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
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The present invention relates to a methacrylic resin composition containing samarium and having excellent optical and mechanical properties, and a method for producing the same. Methacrylic resin is used in a variety of fields due to its excellent transparency, weather resistance, and mechanical properties. However, since methacrylic resin does not have radiation shielding ability, it cannot be used for these purposes. Ta. Therefore, in recent years, radiation shielding materials containing lead in methacrylic resin have been developed (Special Publications Publication No.
No. 2360, Japanese Patent Publication No. 53-9994, No. 53-9995, No. 53
-9996, and 53-63310, etc.). However, although the lead-containing radiation shielding materials described above effectively shield radiation from electromagnetic waves such as X-rays and γ-rays and charged particles such as α-rays and β-rays, they do not shield against neutron radiation. Not enough. On the other hand, it is also known to add a boron compound to polyethylene or methacrylic resin as a polymeric material for shielding neutron beams (Japanese Unexamined Patent Publication No. 144597-1987).
issue). However, although this method also has a large neutron beam absorption capacity, the helium and lithium produced in the neutron absorption reaction have almost no neutron absorption capacity, so their capacity tends to decrease as the amount of neutron absorption increases. However, the optical and mechanical properties have not yet reached a satisfactory level. In addition to the boron compounds mentioned above, samarium, a rare earth element with an atomic number of 64, is known as a substance that absorbs neutron beams, and has an even greater ability to absorb thermal neutron beams than boron. However, since samarium is a metallic solid, it has poor compatibility with methacrylic polymers, and methacrylic resins with excellent optical and mechanical properties have not yet been produced. The inventor of the present invention has arrived at the present invention as a result of various studies in view of the above circumstances. A methacrylic resin composition containing a samarium compound in an amount of 0.01 to 10% by weight based on the total composition. The resin composition of the present invention is achieved by incorporating a samarium compound into a methacrylic resin containing methyl methacrylate as a main component. Therefore, the method for obtaining the composition of the present invention is not particularly limited, and various manufacturing methods can be applied. For example, a method of blending a samarium compound and a methacrylic resin, a method of mixing and polymerizing a samarium compound with a monomer whose main component is methyl methacrylate or a partial polymer thereof, or a method of blending a samarium compound with a monomer whose main component is methyl methacrylate or a method of polymerizing a samarium compound with a monomer whose main component is methyl methacrylate. The polymer may be polymerized by mixing it with a partially polymerized product thereof and a solvent. The resin forming raw material used to constitute the resin composition of the present invention is a methyl methacrylate monomer, a monomer mixture containing methyl methacrylate as a main component, or a partial polymer thereof. The monomer mixture containing methyl methacrylate as a main component consists of methyl methacrylate and another vinyl monomer copolymerizable with methyl methacrylate. Other vinyl monomers copolymerizable with methyl methacrylate are not particularly limited, but include those having 1 to 4 carbon atoms.
alkyl acrylate, alkyl methacrylate having 2 to 4 carbon atoms, styrene, α-methylstyrene, ethylene glycol dimethacrylate, ethylene glycol diacrylate, diethylene glycol dimethacrylate, diethylene glycol diacrylate, tetraethylene glycol dimethacrylate, tetraethylene glycol acrylate, Examples include pentaerythritol tetramethacrylate, pentaerythritol tetraacrylate, allyl acrylate, allyl methacrylate, and the like. The amount of these used is 50% by weight or less in the monomer mixture. Further, it is desirable that the polymer content in the partially polymerized resin raw material used be as small as possible so as not to impair the optical properties of the finally obtained polymer. The samarium used in making up the compositions of the present invention may include samarium compounds such as samarium oxide, samarium carbonate, samarium hydroxide,
Alternatively, samarium salts of inorganic or organic acids such as samarium nitrate, samarium methacrylate, and samarium acrylate obtained by reacting samarium oxide with an inorganic or organic acid, or samarium oxide and acetylacetone, or benzoylacetone Examples include gadolinium complex compounds such as tris(acetylacetonato)samarium or tris(benzoylacetonato)samarium obtained by reacting with the like. The amount of these samarium compounds used is such that the weight concentration of samarium atoms is 0.01 to 10% by weight based on the total weight of the resin composition.
Preferably 1 to 5% by weight is desirable. 0.01% by weight
If it is less than 10% by weight, the resulting resin composition will have little neutron beam shielding effect, and if it exceeds 10% by weight, the optical properties or mechanical strength will deteriorate. These samarium compounds cannot be determined unconditionally depending on the application, but they can be blended with methacrylic resin, mixed with resin-forming raw materials and polymerized, or mixed with resin-forming raw materials and a solvent and polymerized to form methacrylic resin. It can be contained inside. Particularly, the method using the latter solvent is suitable for obtaining transparent resin products without scattering. When blended with a samarium compound or added to a resin forming raw material, preferred examples include those selected from samarium oxide, samarium carbonate, samarium hydroxide compounds, and samarium complex compounds. In addition, when using a samarium compound in a mixture with a resin-forming raw material and a solvent, samarium nitrate, samarium methacrylate, or samarium acrylate obtained by reacting samarium oxide with an inorganic or organic acid can be used. Tris(acetylacetonato)samarium or tris(benzoylacetonato)samarium obtained by reacting samarium salts of inorganic or organic acids such as samarium salts and their double salts, or samarium oxides with acetylacetone, benzoylacetone, etc. Preferred examples include samarium complex compounds such as . The solvent used when producing the resin composition of the present invention has the following general formula K0018 (where R 1 is a saturated carbon number of 1 to 20 or an unsaturated hydrocarbon residue) K0019 (wherein, R 2 is hydrogen or a saturated or unsaturated hydrocarbon residue having 1 to 9 carbon atoms, and R 3 is a saturated or unsaturated hydrocarbon residue having 1 to 9 carbon atoms)
K0020 (In the formula, R 4 is hydrogen or a methyl group, A 1 is an alkyl group having 2 to 6 carbon atoms, and n is 0 or an integer of 1 to 10. ) K0021 (In the formula, R 5 is hydrogen or a methyl group, R 6 is an alkylene group having 2 to 6 carbon atoms) R 7 âOH (5) or (In the formula, R 7 is a saturated group having 3 to 10 carbon atoms) or an unsaturated hydrocarbon residue) R 8 (-A 2 -O)- n H (6) (wherein, R 8 is a hydroxyl group or a saturated or unsaturated hydrocarbon residue having 1 to 10 carbon atoms) , A2 is an alkylene group having 2 to 4 carbon atoms, m is an integer of 2 to 10). The solvents represented by the general formulas (1), (2), (3), (4), (5) and (6) are co-solvents for uniformly dissolving the samarium compound in the resin forming raw material. , unsaturated carboxylic acids such as methacrylic acid and acrylic acid, saturated or unsaturated fatty acids such as propionic acid, octylic acid, isobutyric acid, hexanoic acid, octylbenzoic acid, stearic acid, palmitic acid, naphthenic acid, 2-hydroxyethyl Examples include unsaturated alcohols such as acrylate and 2-hydroxyethyl methacrylate, saturated aliphatic alcohols such as propyl alcohol and cyclohexyl alcohol, and glycols such as ethylene glycol, diethylene glycol and propylene glycol. Among these solvents, monomers copolymerizable with methyl methacrylate, such as methacrylic acid, acrylic acid, 2-hydroxyethyl methacrylate, and 2-hydroxyethyl acrylate, are preferred. These solvents can be used alone or in combination of two or more. The amount of the solvent used in the present invention cannot be determined unconditionally depending on the type and amount of the samarium compound used, but is preferably 40% by weight or less, and preferably 40% by weight or less.
It is 10% by weight or less. If the amount used exceeds 40% by weight, the mechanical and thermal properties of the resulting resin composition will deteriorate, which is not preferred. Examples of the polymerization initiator used in the present invention include peroxides such as benzoyl peroxide and lauroyl peroxide, 2,2'-azobisisobutyronitrile, 2,2'-azobis-(2,4
Known radical initiators such as azobis-based initiators such as -dimethylvaleronitrile) and 2,2'-azobis-(2,4-dimethyl-4-methoxy-valeronitrile) can be used. These polymerization initiators can be used alone or in combination of two or more, and the amount used is 0.001 to 0.1 per 100 parts by weight of resin raw material.
Parts by weight. The polymerization method used to obtain the resin composition of the present invention is not particularly limited, but cast polymerization is a preferred polymerization method. In the case of this cast polymerization, the polymerization mixture prepared from the above components (a), (b) and (c) is mixed with a soft material such as an inorganic glass plate, stainless steel plate, nickel chrome plate or aluminum plate. The mixture is injected into a mold consisting of a vinyl chloride gasket and allowed to polymerize. Cast polymerization is
0.3-15 hours at 45-95â, followed by 10 hours at 100-145â
Polymerization is completed over a period of minutes to 5 hours. In the present invention, if necessary, an ultraviolet absorber,
A mold release agent, a heat stabilizer, a coloring agent, a light diffusing agent, and other neutron shielding compounds, lead compounds, etc. can also be added. The samarium-containing methacrylic resin composition of the present invention, which has the structure described above and has excellent optical and mechanical properties, can be easily produced in the same manufacturing process as general acrylic resins, and is resistant to radiation mainly composed of neutrons. Can be used as a shielding material. Furthermore, when a lead compound is used in combination with the composition of the present invention, X-rays, γ-rays,
It becomes possible to shield from both neutron beams. Although the methacrylic resin composition of the present invention is particularly useful as a neutron shielding material, it can also be used in other applications such as optical filters, optical lenses, light conversion materials, lighting materials, and the like. EXAMPLES Next, the present invention will be explained in more detail with reference to examples, but the present invention is not limited thereto. Reference Example 1 Synthesis of samarium methacrylate 0.3 g of hydroquinone monomethyl ether as a polymerization inhibitor was uniformly dissolved in a mixture of 280 g of methacrylic acid and 1000 g of toluene, and after heating this to 60°C, 174 g of samarium oxide powder was added to this solution.
g over 20 minutes and continued stirring for 1 hour. The reaction solution was then allowed to stand for one day, and then filtered.
The liquid is removed to obtain samarium methacrylate. The yield was 370g. Reference Example 2 Synthesis of samarium nitrate A slight excess of samarium oxide is heated and dissolved in concentrated nitric acid and reacted. After 1 hour, the liquid was cooled to precipitate samarium nitrate crystals. The yield was 60%. Reference example 3 Synthesis of tris(acetylacetonato)samarium 100 c.c. of acetylacetone and 180 g of samarium oxide
was suspended in 3000 c.c. of anhydrous diethyl ether and refluxed for 2 hours, followed by distillation and removal of diethyl ether to obtain crystals of tris(acetylacetonato)samarium. The yield was 65%. Example 1 3 g of samarium nitrate synthesized in Reference Example 2 was mixed with 2-
It is dissolved in a mixed solution of 17 g of hydroxyethyl methacrylate and 2 g of propylene glycol, and 78 g of methyl methacrylate is added to this solution and mixed by stirring. This liquid mixture was a transparent liquid. Next, add 0.04g of 2 as a polymerization catalyst to this mixed solution.
After adding and dissolving 2'-azobis-(2,4-dimethylvaleronitrile) and 0.005 g of dioctyl sulfosuccinate sodium salt as a mold release agent, it was degassed and the plate thickness was set in advance to 3 mm. The mold was poured into a conventional inorganic glass mold, and the mold was immersed in warm water at 65°C for 180 minutes, and then kept in an air bath at 110°C for 120 minutes to complete polymerization. The resin plate taken out from the mold was transparent. Example 2 1.5 g of samarium nitrate synthesized in Reference Example 2 was
-Dissolve in 8.5 g of hydroxyethyl methacrylate, and then add this to 90 g of methyl methacrylate and mix with stirring. This mixture was transparent.
The same type and amount of polymerization catalyst and mold release agent as used in Example 1 were added to this mixed solution, and cast polymerization was carried out under the same conditions as in Example 1. The obtained resin plate was transparent. Example 3 1.5 g of tris(acetylacetonato)samarium synthesized in Reference Example 3 is dissolved in 8.5 g of methacrylic acid, and this solution is added to 90 g of methyl methacrylate and mixed by stirring. The same polymerization catalyst and mold release agent as in Example 1 were added to this mixed solution, and the same cast polymerization as in Example 1 was performed.
After the polymerization was completed, the resin plate peeled off from the mold was transparent although it had a very slight yellow color. Example 4 Samarium methacrylate 8 synthesized in Reference Example 1
g, n-octylic acid 2g, propylene glycol 1g, 2-hydroxyethyl methacrylate 1
g, 5 g of styrene and 83 g of methyl methacrylate
were mixed, and cast polymerization was repeated under the same polymerization conditions as in Example 1. The resulting resin plate was slightly yellow but transparent. Example 5 Partial polymer of methyl methacrylate (polymerization rate 18
%) 100 parts by weight, α,αâ²-azobis-(2,4-dimethylvaleronitrile) 0.04 as a polymerization catalyst
Parts by weight, 0.005 parts by weight of dioctyl sulfosuccinate sodium salt as a mold release agent, average particle size 2Ό
Add and mix 2.0 parts by weight of samarium oxide,
After degassing, it was poured into a mold made of tempered glass with a thickness of 3 mm and a soft vinyl chloride gasket, immersed in hot water at 70°C for 60 minutes, and then placed in an air bath at 130°C. The polymerization was completed after being left for 80 minutes to obtain a resin plate. Example 6 Average particle size per 100 parts by weight of methacrylic resin (manufactured by Mitsubishi Rayon Co., Ltd., trade name Acrypet VH)
Add 2.0 parts by weight of samarium hydroxide with a particle size of 0.5Ό and 1.0 parts by weight of samarium carbonate with an average particle size of 2Ό, mix thoroughly in a tumbler to make the mixture homogeneous, and then extrude it from an extruder using a conventional method to obtain a sheet with a thickness of 3 mm. Ta. The results of total light transmittance (%), haze value (%), bending fracture strength (Kg/cm 2 ), and neutron shielding ability (thermal neutron absorption cross section) of the methacrylic resin plates obtained in Examples 1 to 7 are shown below. It is shown in Table 1. In addition, total light transmittance and haze value are ASTM-D
-1003-61, bending fracture strength was measured according to ASTM-D-790. The thermal neutron absorption cross section was determined using the numerical values described in Experimental Chemistry Course (12) Radiochemistry (Maruzen) and the following formula. S = (W 1 /M 1 ÃS 1 +W 2 /M 2 ÃS 2 +... + Wn / Mn à Sn) à N However, S Thermal neutron absorption cross section per 100g of composition (cm 2 ) Mi i species Atomic weight of element Wi Abundance of i-type element Si Thermal neutron absorption cross section of i-type element (barns) N Avogadro's number (i=1...n)
ãè¡šããtableã
Claims (1)
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é èšèŒã®ã¡ã¿ã¯ãªã«æš¹èçµæç©ã®è£œé æ³ã[Scope of Claims] 1. A methacrylic resin composition containing a samarium compound in a methacrylic resin whose main component is methyl methacrylate so that the weight concentration of samarium atoms is 0.01 to 10% by weight based on the total composition. thing. 2 (a) Methyl methacrylate monomer or a monomer mixture containing methyl methacrylate as a main component,
or a resin-forming raw material selected from partial polymers thereof, (b) a samarium compound in an amount such that the weight concentration of samarium atoms is 0.01 to 10% by weight based on the total composition, and (c) a polymerization mixture consisting of a polymerization initiator. 1. A method for producing a methacrylic resin composition, which comprises polymerizing a methacrylic resin composition. 3. The method for producing a methacrylic resin composition according to claim 2, wherein the samarium compound is selected from samarium oxide, samarium carbonate, samarium hydroxide, and a complex compound of samarium. 4 The following general formula showing solubility in resin forming raw materials and samarium compounds K0014 (In the formula, R 1 is a saturated or unsaturated hydrocarbon residue having 1 to 20 carbon atoms) K0015 (In the formula, R 2 is hydrogen or a saturated or unsaturated hydrocarbon residue having 1 to 9 carbon atoms, R 3 is hydrogen or a saturated or unsaturated hydrocarbon residue having 1 to 9 carbon atoms;
4 saturated or unsaturated hydrocarbon residues. ) K0016 (In the formula, R 4 is hydrogen or a methyl group, A 1 is an alkyl group having 2 to 6 carbon atoms, and n is 0 or an integer of 1 to 10) K0017 (In the formula, R 5 is hydrogen or a methyl group , R 6 is an alkylene group having 2 to 6 carbon atoms) R 7 -OH (5) (wherein, R 7 is a saturated or unsaturated hydrocarbon residue having 3 to 10 carbon atoms) or R 8 (-A2 - O) -nH (6) (wherein, R8 is a hydroxyl group or a saturated or unsaturated hydrocarbon residue having 1 to 10 carbon atoms, A2 is an alkylene group having 2 to 4 carbon atoms, The method for producing a methacrylic resin composition according to claim 2, characterized in that the polymerization is carried out by adding at least one solvent selected from the following (m is an integer of 2 to 10). 5. The method for producing a methacrylic resin composition according to claim 4, wherein the samarium compound is selected from samarium nitrate, a samarium salt of an organic acid, or a samarium complex compound. 6 The samarium compound is selected from samarium methacrylate, samarium acrylate or samarium tris(acetylacetonato), and the solvent is octylic acid and propylene glycol and/or 2-hydroxyethyl methacrylate or 2-hydroxyethyl acrylate. The fourth claim characterized in that
A method for producing a methacrylic resin composition as described in Section 1.
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP19580282A JPS5986611A (en) | 1982-11-08 | 1982-11-08 | Methacrylate resin composition and its production |
DE8383306711T DE3375794D1 (en) | 1982-11-08 | 1983-11-03 | Synthetic resin composition and process for producing the same |
EP83306711A EP0108622B1 (en) | 1982-11-08 | 1983-11-03 | Synthetic resin composition and process for producing the same |
US06/548,444 US4563494A (en) | 1982-11-08 | 1983-11-03 | Synthetic resin composition and process for producing the same |
IT23617/83A IT1170240B (en) | 1982-11-08 | 1983-11-07 | COMPOSITION BASED ON SYNTHETIC RESIN AND PROCESS FOR ITS PRODUCTION |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP19580282A JPS5986611A (en) | 1982-11-08 | 1982-11-08 | Methacrylate resin composition and its production |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5986611A JPS5986611A (en) | 1984-05-18 |
JPH0262563B2 true JPH0262563B2 (en) | 1990-12-26 |
Family
ID=16347216
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP19580282A Granted JPS5986611A (en) | 1982-11-08 | 1982-11-08 | Methacrylate resin composition and its production |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5986611A (en) |
-
1982
- 1982-11-08 JP JP19580282A patent/JPS5986611A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS5986611A (en) | 1984-05-18 |
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