JPWO2020013232A1 - パラミロン系樹脂、成形用材料および成形体、並びにパラミロン系樹脂の製造方法 - Google Patents
パラミロン系樹脂、成形用材料および成形体、並びにパラミロン系樹脂の製造方法 Download PDFInfo
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- JPWO2020013232A1 JPWO2020013232A1 JP2020530230A JP2020530230A JPWO2020013232A1 JP WO2020013232 A1 JPWO2020013232 A1 JP WO2020013232A1 JP 2020530230 A JP2020530230 A JP 2020530230A JP 2020530230 A JP2020530230 A JP 2020530230A JP WO2020013232 A1 JPWO2020013232 A1 JP WO2020013232A1
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- Prior art keywords
- paramylon
- based resin
- acid
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- chain
- Prior art date
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- 239000012778 molding material Substances 0.000 title claims description 12
- 238000000034 method Methods 0.000 title description 54
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 37
- 125000002252 acyl group Chemical group 0.000 claims abstract description 22
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 17
- 238000006467 substitution reaction Methods 0.000 claims abstract description 16
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 13
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 12
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- 125000001424 substituent group Chemical group 0.000 description 25
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- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 10
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- 230000003213 activating effect Effects 0.000 description 9
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- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
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- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- MYWGVEGHKGKUMM-UHFFFAOYSA-N carbonic acid;ethene Chemical compound C=C.C=C.OC(O)=O MYWGVEGHKGKUMM-UHFFFAOYSA-N 0.000 description 1
- PTFIPECGHSYQNR-UHFFFAOYSA-N cardanol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 description 1
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- 238000005119 centrifugation Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
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- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical compound C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical class OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 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
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 1
- PCYQQSKDZQTOQG-NXEZZACHSA-N dibutyl (2r,3r)-2,3-dihydroxybutanedioate Chemical compound CCCCOC(=O)[C@H](O)[C@@H](O)C(=O)OCCCC PCYQQSKDZQTOQG-NXEZZACHSA-N 0.000 description 1
- 229940100539 dibutyl adipate Drugs 0.000 description 1
- RISLXYINQFKFRL-UHFFFAOYSA-N dibutyl nonanedioate Chemical compound CCCCOC(=O)CCCCCCCC(=O)OCCCC RISLXYINQFKFRL-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 description 1
- XWVQUJDBOICHGH-UHFFFAOYSA-N dioctyl nonanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCC(=O)OCCCCCCCC XWVQUJDBOICHGH-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- CAEMOCUMMOVWCN-UHFFFAOYSA-N diphosphono hydrogen phosphate phosphoric acid Chemical class OP(O)(O)=O.OP(O)(=O)OP(O)(=O)OP(O)(O)=O CAEMOCUMMOVWCN-UHFFFAOYSA-N 0.000 description 1
- NJLLQSBAHIKGKF-UHFFFAOYSA-N dipotassium dioxido(oxo)titanium Chemical compound [K+].[K+].[O-][Ti]([O-])=O NJLLQSBAHIKGKF-UHFFFAOYSA-N 0.000 description 1
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- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 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
- 230000007613 environmental effect Effects 0.000 description 1
- CGWFVEFHQWJOKI-UHFFFAOYSA-N ethyl 2-benzoylbenzoate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 CGWFVEFHQWJOKI-UHFFFAOYSA-N 0.000 description 1
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 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
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229910001701 hydrotalcite Inorganic materials 0.000 description 1
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- 238000001746 injection moulding Methods 0.000 description 1
- 239000012784 inorganic fiber Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000005339 levitation Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000001247 metal acetylides Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
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- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910052914 metal silicate Inorganic materials 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral 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
- 125000001419 myristoyl group Chemical group O=C([*])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
- 125000001421 myristyl 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])[H] 0.000 description 1
- FGTVYMTUTYLLQR-UHFFFAOYSA-N n-ethyl-1-phenylmethanesulfonamide Chemical compound CCNS(=O)(=O)CC1=CC=CC=C1 FGTVYMTUTYLLQR-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- YAFOVCNAQTZDQB-UHFFFAOYSA-N octyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCCCC)OC1=CC=CC=C1 YAFOVCNAQTZDQB-UHFFFAOYSA-N 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
- 239000003960 organic solvent Substances 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])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
- 230000035515 penetration Effects 0.000 description 1
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002961 polybutylene succinate Polymers 0.000 description 1
- 239000004631 polybutylene succinate Substances 0.000 description 1
- 229920009537 polybutylene succinate adipate Polymers 0.000 description 1
- 239000004630 polybutylene succinate adipate Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000003763 resistance to breakage Effects 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 150000003899 tartaric acid esters Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000013306 transparent fiber Substances 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- WEAPVABOECTMGR-UHFFFAOYSA-N triethyl 2-acetyloxypropane-1,2,3-tricarboxylate Chemical compound CCOC(=O)CC(C(=O)OCC)(OC(C)=O)CC(=O)OCC WEAPVABOECTMGR-UHFFFAOYSA-N 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- MTPVUVINMAGMJL-UHFFFAOYSA-N trimethyl(1,1,2,2,2-pentafluoroethyl)silane Chemical compound C[Si](C)(C)C(F)(F)C(F)(F)F MTPVUVINMAGMJL-UHFFFAOYSA-N 0.000 description 1
- YZWRNSARCRTXDS-UHFFFAOYSA-N tripropionin Chemical compound CCC(=O)OCC(OC(=O)CC)COC(=O)CC YZWRNSARCRTXDS-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/02—Algae
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
前記長鎖成分による置換度(DSLo)と前記短鎖成分による置換度(DSSh)が、以下の条件式(1)及び(2)を満たし、
アイゾット衝撃強度が5.0kJ/m2以上であり、
MFR(210℃、荷重5kgにおけるメルトフローレート)が2g/10min以上である、パラミロン系樹脂が提供される。
2.2 ≦ DSLo+DSSh ≦ 2.8 (1)
5≦ DSSh/DSLo ≦ 25 (2)
酸捕捉成分の存在下、加温下で、
溶媒中に分散された重量平均分子量70000〜140000のパラミロンと、
塩化アセチル又は/及び塩化プロピオニルと、
前記長鎖成分を有する長鎖脂肪酸の酸塩化物である長鎖反応剤とを反応させて、該パラミロンを構成するパラミロンのヒドロキシ基をアシル化する工程と、
前記アシル化工程により得られたアシル化パラミロンを前記溶媒から分離する工程を含む、パラミロン系樹脂の製造方法が提供される。
2.2 ≦ DSLo+DSSh ≦ 2.8 (1)
5≦ DSSh/DSLo ≦ 25 (2)
カラム:PLgel20μmMIXED-A(製品名、アジレントテクノロジー(株)製)
溶離液:ジメチルアセトアミド(DMAc)溶液(0.1M LiCl)
流速:0.5mL/min
検出器:RI(示差屈折率)(東ソー(株)製RI-71)
温度:23.0℃
標準試料:Pullulan standard
カラム:SHIMPAC GPC-80MC×2本、GPC-8025C×1本(製品名、島津製作所(株)製)
溶離液:クロロホルム(CHCl3)
流速:1.0mL/min
検出器:RI(示差屈折率)(島津製作所製 RID-10A)
温度:40.0℃
標準試料:Polystyrene standard
パラミロンは、下記式(1)で示されるβ−D−グルコース分子(β−D−グルコピラノース)がβ(1→3)グリコシド結合により重合した直鎖状の高分子である。パラミロンを構成する各グルコース単位は三つのヒドロキシ基を有している(式中のnは自然数を示す)。本発明の実施形態では、このようなパラミロンに、これらのヒドロキシ基を利用して、短鎖有機基および長鎖有機基を導入することができる。
本発明の実施形態によるパラミロン系樹脂は、パラミロンのヒドロキシ基を利用して、前記短鎖成分に加えて前記長鎖成分が導入されたものである。
本発明の実施形態によるパラミロン系樹脂は、パラミロンのヒドロキシ基を利用して、前記長鎖成分に加えて、前記短鎖成分が導入されたものである。短鎖成分として、アセチル基又は/及びプロピオニル基が好ましく、少なくともプロピオニル基を含むことが好ましく、プロピオニル基が特に好ましい。
ヒドロキシ基の残存量が多いほど、パラミロン系樹脂の最大強度や耐熱性が大きくなる傾向がある一方で、吸水性が高くなる傾向がある。一方、ヒドロキシ基の変換率(置換度)が高いほど、吸水性が低下し、可塑性や破断歪みが増加する傾向がある一方で、最大強度や耐熱性が低下する傾向がある。これらの傾向等を考慮して、ヒドロキシ基の変換率を適宜設定することができる。
パラミロンに長鎖成分と短鎖成分を導入するための反応工程の前に、パラミロンの反応性を上げるために、活性化処理(前処理工程)を行うことができる。この活性化処理は、パラミロンのアセチル化の前に通常行われる活性化処理を適用できる。
本発明の実施形態によるパラミロン誘導体(パラミロン系樹脂)は、以下に示す方法によって製造することができる。
綿繊維製のろ紙(5B、40mmφ、含水率約2%)を各溶媒に室温下1hr浸漬する。浸漬前後の重量を測定し、下式に当てはめて保液率(vol%)を求める。浸漬後の試料から溶媒のしたたりがとまった時点で重量を測定した。
上記のアシル化の工程の後、アルカリ性水溶液を加えて、加温しながら保持(熟成)することが好ましい。この熟成時の温度は25〜75℃が好ましく、40〜70℃が好ましく、熟成の時間は1〜5時間の範囲に設定でき、1〜3時間の範囲が好ましい。
長鎖成分および短鎖成が導入されたパラミロン誘導体(生成物)は、通常の回収方法に従って反応溶液から回収することができ、その方法は限定されるものではないが、生成物が反応溶液に溶解していない場合は、反応溶液と生成物とを固液分離する回収方法が製造エネルギーの観点から好ましい。生成物が反応溶液に溶解ないし親和して固液分離が困難な場合は、反応溶液を留去し生成物を残留分として回収することができる。あるいは、反応溶液に、生成物に対する貧溶媒を添加することにより、析出した生成物を固液分離して回収してもよい。
アシル化剤として長鎖成分と短鎖成分を有する混合酸無水物を用い、固液不均一系でパラミロンをアシル化することで、パラミロン系樹脂を得ることができる。パラミロンは活性化処理することが好ましい。活性化処理は通常の方法で行うことができる。
本発明の実施形態によるパラミロン誘導体は、所望の特性に応じて添加剤を加え、成形用材料に好適な樹脂組成物を得ることができる。このパラミロン誘導体は、通常のパラミロン誘導体と相溶する添加剤と相溶させることができる。
(有機置換基の式量/有機置換基当量)×100 (I)
x×w/[(1−x)×74+x×(59+w)]×100 (II)
154×x/[74×(1−x)+198×x]×100 (III)
−(CO−R23−COO−R24−O−)− (21)
−(CO−R25−O−)− (22)
ここでベース樹脂とは、成形用材料中の主成分を意味し、この主成分の機能を妨げない範囲で他の成分を含有することを許容することを意味し、特にこの主成分の含有割合を特定するものではないが、この主成分が組成物中の50質量%以上、好ましくは70質量%以上、より好ましくは80質量%以上、特に好ましくは90質量%以上を占めることを包含するものである。
パラミロン及びパラミロン系樹脂の重量平均分子量はGPCにより以下の条件で測定して求めた。測定結果を表1〜3に示す。
カラム:PLgel20μmMIXED-A(製品名、アジレントテクノロジー(株)製)
溶離液:ジメチルアセトアミド(DMAc)溶液(0.1M LiCl)
流速:0.5mL/min
検出器:RI(示差屈折率)( 東ソー(株)製RI-71)
温度:23.0℃
標準試料:Pullulan standard
ポンプ:島津製作所製LC-20AD
オートサンプラ―:島津製作所製SIL-20ACHT
カラムオーブン:東ソー製CTO-20AC
カラム:SHIMPAC GPC-80MC×2本、GPC-8025C×1本(製品名、島津製作所(株)製)
溶離液:クロロホルム(CHCl3)
流速:1.0mL/min
検出器:RI(示差屈折率)(島津製作所製 RID-10A)
温度:40.0℃
標準試料:Polystyrene standard
ポンプ:島津製作所製LC-20AD
オートサンプラ―:島津製作所製SIL-20A
カラムオーブン:島津製作所製CTO-20A
原料パラミロンを塩酸水溶液で処理することで、分子量を調整したパラミロン1を得た。次に、パラミロン1を固液不均一系でアシル化することで、本実施例のパラミロン系樹脂を得た。具体的には、下記に従ってパラミロン系樹脂(パラミロンプロピオネートステアレート)を作製した。
ガラス転移点は、下記の条件で示差走査熱量測定(DSC:Differential scanning calorimetry)を行って求めた。測定装置は、セイコーインスツルメンツ社のEXSTAR2000,DSC6200を用いた。
パラミロン系樹脂を20℃から200℃まで10℃/minで昇温した後、200℃から−30℃まで50℃/minで急冷した。そして、−30℃から200℃まで20℃/minで昇温した時のガラス転移点(Tg)を測定した。
射出成形(Thermo Electron Corporation製、HAAKE MiniJet II)を使用して、上記で得たパラミロン系樹脂から下記形状の成形体を作製した。
成形体サイズ:厚み2.4mm、幅12.4mm、長さ80mm
その際、成形機のシリンダー温度を200℃、金型温度を65℃、射出圧力1200bar(120MPa)で5秒間、保圧600bar(60MPa)で20秒間の成形条件に設定した。
上記の成形体について、JIS K7171に基づいて曲げ試験を行い、最大曲げ応力、曲げ弾性率、曲げ破断伸びを測定した。
上記の成形体について、JIS K7110に記載の条件でノッチ付きアイゾット衝撃強度を測定した。
アイゾット衝撃強度の評価基準
○:5.0kJ/m2以上
×:5.0kJ/m2未満
高下式フローテスター(島津製作所株式会社製、製品名:CFT−500D)を用い、JIS7210:1990に基づいて、温度210℃、荷重5kg、ダイ2mmφ×10mm(穴の直径2mm、穴の長さ10mm)、余熱2分(試料をシリンダー充填してピストンを挿入した時点から荷重をかけるまでの時間)の条件でMFRを測定した。
MFRの評価基準
○:2g/10min以上
×:2g/10min未満
原料パラミロン(重量平均分子量242000)15g及び3%塩酸水溶液150gを反応器に投入し、100℃で4時間撹拌後、水で洗浄することで、分子量を調整したパラミロン2を得た。パラミロン2の重量平均分子量(Mw)は、83700であった。パラミロン1をパラミロン2に変更した以外は実施例1と同様の分量と方法に従って、パラミロン系樹脂(パラミロンプロピオネートステアレート)を作製した(収量9.3g、収率99%)。
原料パラミロン(重量平均分子量242000)15g及び3%塩酸水溶液150gを反応器に投入し、100℃で6時間撹拌後、水で洗浄することで、分子量を調整したパラミロン3を得た。パラミロン3の重量平均分子量(Mw)は、71200であった。パラミロン1をパラミロン3に変更した以外は実施例1と同様の分量と方法に従って、パラミロン系樹脂(パラミロンプロピオネートステアレート)を作製した(収量8.9g、収率93%)。
原料パラミロン(重量平均分子量242000)を塩酸水溶液で処理しないでアシル化した以外は実施例1と同様の分量と方法に従って、パラミロン系樹脂(パラミロンプロピオネートステアレート)を作製した(収量8.9g、収率93%)。
長鎖反応剤と短鎖反応剤の量をステアロイルクロリド3.36g(11.1mmol)と塩化プロピオニル7.70g(83.3mmol)へ変更した以外は実施例1と同じ方法に従って、パラミロン系樹脂(パラミロンプロピオネートステアレート)を作製した(収量8.3g、収率82%)。
長鎖反応剤と短鎖反応剤の量をステアロイルクロリド2.10g(6.90mmol)と塩化プロピオニル6.41g(69.4mmol)へ変更した以外は実施例1と同じ方法に従って、パラミロン系樹脂(パラミロンプロピオネートステアレート)を作製した(収量9.3g、収率96%)。
長鎖反応剤と短鎖反応剤の量をステアロイルクロリド0.84g(2.80mmol)と塩化プロピオニル7.70g(83.3mmol)へ変更した以外は実施例1と同じ方法に従って、パラミロン系樹脂(パラミロンプロピオネートステアレート)を作製した(収量9.3g、収率95%)。
パラミロン1に代えてパラミロン2を用い、長鎖反応剤と短鎖反応剤の量をステアロイルクロリド3.36g(11.1mmol)と塩化プロピオニル7.70g(83.3mmol)へ変更した以外は実施例1と同じ方法に従って、パラミロン系樹脂(パラミロンプロピオネートステアレート)を作製した(収量9.0g、収率89%)。
パラミロン1に代えてパラミロン3を用い、長鎖反応剤と短鎖反応剤の量をステアロイルクロリド3.36g(11.1mmol)と塩化プロピオニル7.70g(83.3mmol)へ変更した以外は実施例1と同じ方法に従って、パラミロン系樹脂(パラミロンプロピオネートステアレート)を作製した(収量9.5g、収率91%)。
原料パラミロンを塩酸水溶液で処理しないでアシル化を行い、長鎖反応剤と短鎖反応剤の量をステアロイルクロリド3.99g(13.2mmol)と塩化プロピオニル8.54g(92.3mmol)へ変更した以外は実施例1と同じ方法に従って、パラミロン系樹脂(パラミロンプロピオネートステアレート)を作製した(収量8.5g、収率83%)。
パラミロン1に代えてパラミロン2を用い、長鎖反応剤と短鎖反応剤の量をステアロイルクロリド6.73g(22.2mmol)と塩化プロピオニル7.70g(83.3mmol)へ変更した以外は実施例1と同じ方法に従って、パラミロン系樹脂(パラミロンプロピオネートステアレート)を作製した(収量11.4g、収率96%)。
パラミロン1に代えてパラミロン2を用い、長鎖反応剤と短鎖反応剤の量をステアロイルクロリド1.68g(5.60mmol)と塩化プロピオニル6.16g(66.6mmol)へ変更した以外は実施例1と同じ方法に従って、パラミロン系樹脂(パラミロンプロピオネートステアレート)を作製した(収量8.1g、収率92%)。
また、パラミロンの重量平均分子量が70000〜140000の範囲内であっても、比較例3のように長鎖の付加量(DSLo)が高すぎると柔軟性が高まるため、最大曲げ応力、曲げ弾性率および耐熱性(Tg)は低下することが分かる。
逆に、比較例4のように長鎖の付加量(DSLo)が低く、且つ長鎖と短鎖の付加量(DSLo+DSSh)が小さいと、耐衝撃性および熱可塑性(流動性:MFR)が低下することが分かる。
パラミロン1に代えてパラミロン3を用い、ステアロイルクロリドの量を4.20g(13.9mmol)へ変更し、さらに短鎖反応剤を塩化アセチル6.54g(83.3mmol)へ変更した以外は実施例1と同じ方法に従って、パラミロン系樹脂(パラミロンアセテートステアレート)を作製した(収量9.5g、収率97%)。
パラミロン1に代えてパラミロン3を用い、ステアロイルクロリドの量を4.20g(13.9mmol)へ変更し、さらに短鎖反応剤を塩化アセチル3.27g(41.6mmol)及び塩化プロピオニル3.85g(41.6mmol)へ変更した以外は実施例1と同じ方法に従って、パラミロン系樹脂(パラミロンアセテートプロピオネートステアレート)を作製した(収量10.2g、収率97%)。
原料パラミロンを塩酸水溶液で処理しないでアシル化を行い、ステアロイルクロリドの量を4.44g(14.6mmol)へ変更し、さらに短鎖反応剤を塩化アセチル6.90g(87.9mmol)へ変更した以外は実施例1と同じ方法に従って、パラミロン系樹脂(パラミロンアセテートステアレート)を作製した(収量8.5g、収率94%)。
原料パラミロンを塩酸水溶液で処理しないでアシル化を行い、ステアロイルクロリドの量を3.74g(12.3mmol)へ変更し、さらに短鎖反応剤を塩化アセチル2.90g(36.9mmol)及び塩化プロピオニル3.42g(37.0mmol)へ変更した以外は実施例1と同じ方法に従って、パラミロン系樹脂(パラミロンアセテートプロピオネートステアレート)を作製した(収量9.3g、収率96%)。
原料パラミロン(重量平均分子量242000)15g及び5%塩酸水溶液150gを反応器に投入し、90℃で4時間撹拌後、水で洗浄することで、分子量を調整したパラミロン4を得た。パラミロン4の重量平均分子量(Mw)は、96700であった。
パラミロン1をパラミロン4に変更し、混合液の量をN−メチルピロリドン51mLとピリジン7.1mLに変更し、長鎖反応剤としてミリストイルクロリド2.74g(11.1mmol)へ変更した以外は実施例1と同じ方法に従って、パラミロン系樹脂(パラミロンプロピオネートミリステート)を作製した(収量9.3g、収率95%)。
Claims (9)
- パラミロンの重量平均分子量が70000〜140000の範囲にあり、該パラミロンのヒドロキシ基の水素原子が、炭素数14以上の直鎖状飽和脂肪族アシル基である長鎖成分と、炭素数2又は3のアシル基(アセチル基又は/及びプロピオニル基)である短鎖成分で置換されたパラミロン系樹脂であって、
前記長鎖成分による置換度(DSLo)と前記短鎖成分による置換度(DSSh)が、以下の条件式(1)及び(2)を満たし、
アイゾット衝撃強度が5.0kJ/m2以上であり、
MFR(210℃、荷重5kgにおけるメルトフローレート)が2g/10min以上である、パラミロン系樹脂。
2.2 ≦ DSLo+DSSh ≦ 2.8 (1)
5≦ DSSh/DSLo ≦ 25 (2) - DSLoが0.1〜0.5の範囲にあり、DSShが2.0〜2.5の範囲にある、請求項1に記載のパラミロン系樹脂。
- 前記長鎖成分がミリスチン酸、パルミチン酸、ステアリン酸、アラキジン酸、ベヘン酸から選ばれる少なくとも一種の脂肪酸のアシル基部分である、請求項1又は2に記載のパラミロン系樹脂。
- 請求項1から3のいずれか一項に記載のパラミロン系樹脂を含む成形用材料。
- 請求項4に記載の成形用材料を用いて形成された成形体。
- 請求項1から3のいずれか一項に記載のパラミロン系樹脂を製造する方法であって、
酸捕捉成分の存在下、加温下で、
溶媒中に分散された重量平均分子量70000〜140000のパラミロンと、
塩化アセチル又は/及び塩化プロピオニルと、
前記長鎖成分を有する長鎖脂肪酸の酸塩化物である長鎖反応剤とを反応させて、該パラミロンのヒドロキシ基をアシル化する工程と、
前記アシル化工程により得られたアシル化パラミロンを前記溶媒から分離する工程を含む、パラミロン系樹脂の製造方法。 - 前記溶媒が、水、酢酸、ジオキサン、ピリジン、N−メチルピロリドン、N,N−ジメチルアセトアミド、N,N−ジメチルホルムアミド、ジメチルスルホキシドから選ばれる少なくとも1種である、請求項6又は7に記載のパラミロン系樹脂の製造方法。
- 前記酸捕捉成分は、トリエチルアミンまたはピリジンを含む、請求項6又は7に記載のパラミロン系樹脂の製造方法。
- 前記溶媒の量は、前記パラミロンの乾燥質量に対して10〜50倍量である、請求項6から8のいずれか一項に記載のパラミロン系樹脂の製造方法。
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JP2022003113A (ja) * | 2020-06-23 | 2022-01-11 | 株式会社リコー | 樹脂組成物、成形体、電子部品及び電子機器 |
WO2022255447A1 (ja) | 2021-06-03 | 2022-12-08 | 株式会社Lixil | βグルカンエステル誘導体 |
WO2023209790A1 (ja) * | 2022-04-26 | 2023-11-02 | 日本電気株式会社 | パラミロン系樹脂及びその製造方法、成形用樹脂組成物、並びに成形体 |
WO2023248911A1 (ja) * | 2022-06-22 | 2023-12-28 | 日東電工株式会社 | 粘着剤組成物、粘着シート、積層体、及びβ-1,3-グルカン誘導体の製造方法 |
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