JP2005290113A - 相溶化剤 - Google Patents
相溶化剤 Download PDFInfo
- Publication number
- JP2005290113A JP2005290113A JP2004104755A JP2004104755A JP2005290113A JP 2005290113 A JP2005290113 A JP 2005290113A JP 2004104755 A JP2004104755 A JP 2004104755A JP 2004104755 A JP2004104755 A JP 2004104755A JP 2005290113 A JP2005290113 A JP 2005290113A
- Authority
- JP
- Japan
- Prior art keywords
- group
- resin
- bis
- fluorene
- compound
- 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.)
- Granted
Links
- 229920000642 polymer Polymers 0.000 claims abstract description 109
- 229920003023 plastic Polymers 0.000 claims abstract description 85
- 239000004033 plastic Substances 0.000 claims abstract description 85
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 239000000463 material Substances 0.000 claims abstract description 60
- 229920005989 resin Polymers 0.000 claims description 105
- 239000011347 resin Substances 0.000 claims description 105
- 239000003795 chemical substances by application Substances 0.000 claims description 40
- 239000003063 flame retardant Substances 0.000 claims description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 30
- 229920000554 ionomer Polymers 0.000 claims description 29
- 125000003277 amino group Chemical group 0.000 claims description 26
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 239000000178 monomer Substances 0.000 claims description 21
- 229920001225 polyester resin Polymers 0.000 claims description 20
- 239000004645 polyester resin Substances 0.000 claims description 20
- 229920001187 thermosetting polymer Polymers 0.000 claims description 19
- 239000011256 inorganic filler Substances 0.000 claims description 17
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 17
- 229920001971 elastomer Polymers 0.000 claims description 15
- 239000000806 elastomer Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229920001721 polyimide Polymers 0.000 claims description 11
- 239000009719 polyimide resin Substances 0.000 claims description 10
- 229920005749 polyurethane resin Polymers 0.000 claims description 10
- 229920000178 Acrylic resin Polymers 0.000 claims description 9
- 239000004925 Acrylic resin Substances 0.000 claims description 9
- 125000000524 functional group Chemical group 0.000 claims description 9
- 229920005668 polycarbonate resin Polymers 0.000 claims description 8
- 239000004431 polycarbonate resin Substances 0.000 claims description 8
- 229920005992 thermoplastic resin Polymers 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 230000000704 physical effect Effects 0.000 abstract description 37
- 230000001172 regenerating effect Effects 0.000 abstract description 2
- 150000001336 alkenes Chemical group 0.000 abstract 1
- -1 polyethylene terephthalate Polymers 0.000 description 134
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical group C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 116
- 238000000034 method Methods 0.000 description 43
- 150000002009 diols Chemical class 0.000 description 40
- 125000002947 alkylene group Chemical group 0.000 description 36
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 27
- 229920001577 copolymer Polymers 0.000 description 22
- PTBCCLLVPOLXES-UHFFFAOYSA-N 2-[9-(2-hydroxyphenyl)fluoren-9-yl]phenol Chemical class OC1=CC=CC=C1C1(C=2C(=CC=CC=2)O)C2=CC=CC=C2C2=CC=CC=C21 PTBCCLLVPOLXES-UHFFFAOYSA-N 0.000 description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 19
- 125000003545 alkoxy group Chemical group 0.000 description 17
- 229920000139 polyethylene terephthalate Polymers 0.000 description 17
- 239000005020 polyethylene terephthalate Substances 0.000 description 17
- 229920005862 polyol Polymers 0.000 description 16
- 150000003077 polyols Chemical class 0.000 description 16
- 150000002220 fluorenes Chemical class 0.000 description 15
- 239000000835 fiber Substances 0.000 description 14
- YWFPGFJLYRKYJZ-UHFFFAOYSA-N 9,9-bis(4-hydroxyphenyl)fluorene Chemical class C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 YWFPGFJLYRKYJZ-UHFFFAOYSA-N 0.000 description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- 239000004698 Polyethylene Substances 0.000 description 13
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 13
- 229920000573 polyethylene Polymers 0.000 description 13
- 239000004793 Polystyrene Substances 0.000 description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 11
- 229920002223 polystyrene Polymers 0.000 description 11
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000000465 moulding Methods 0.000 description 10
- 239000004743 Polypropylene Substances 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 238000001125 extrusion Methods 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 238000005191 phase separation Methods 0.000 description 9
- 229920000515 polycarbonate Polymers 0.000 description 9
- 239000004417 polycarbonate Substances 0.000 description 9
- 229920001155 polypropylene Polymers 0.000 description 9
- 238000004064 recycling Methods 0.000 description 9
- 239000002699 waste material Substances 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 150000004985 diamines Chemical class 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 238000001746 injection moulding Methods 0.000 description 8
- 239000000155 melt Substances 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 8
- 238000006467 substitution reaction Methods 0.000 description 8
- QDMXRSFKPPVBDW-UHFFFAOYSA-N 2-[9-(2-aminophenyl)fluoren-9-yl]aniline Chemical class NC1=CC=CC=C1C1(C=2C(=CC=CC=2)N)C2=CC=CC=C2C2=CC=CC=C21 QDMXRSFKPPVBDW-UHFFFAOYSA-N 0.000 description 7
- 239000004952 Polyamide Substances 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 230000006866 deterioration Effects 0.000 description 7
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 7
- 229920002647 polyamide Polymers 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 229920002725 thermoplastic elastomer Polymers 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 6
- 125000005037 alkyl phenyl group Chemical group 0.000 description 6
- 239000003822 epoxy resin Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 229920000647 polyepoxide Polymers 0.000 description 6
- 229920000098 polyolefin Polymers 0.000 description 6
- 229920005672 polyolefin resin Polymers 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- KIFDSGGWDIVQGN-UHFFFAOYSA-N 4-[9-(4-aminophenyl)fluoren-9-yl]aniline Chemical class C1=CC(N)=CC=C1C1(C=2C=CC(N)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 KIFDSGGWDIVQGN-UHFFFAOYSA-N 0.000 description 5
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 229920000578 graft copolymer Polymers 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 229920002492 poly(sulfone) Polymers 0.000 description 5
- 229920006122 polyamide resin Polymers 0.000 description 5
- 229920000768 polyamine Polymers 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- 229920006337 unsaturated polyester resin Polymers 0.000 description 5
- LTMQZVLXCLQPCT-UHFFFAOYSA-N 1,1,6-trimethyltetralin Chemical compound C1CCC(C)(C)C=2C1=CC(C)=CC=2 LTMQZVLXCLQPCT-UHFFFAOYSA-N 0.000 description 4
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 4
- GYLHMFMJRFZBBW-UHFFFAOYSA-N 3-[9-(2,3-dihydroxyphenyl)fluoren-9-yl]benzene-1,2-diol Chemical class OC1=CC=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C(=C(O)C=CC=2)O)=C1O GYLHMFMJRFZBBW-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 125000005907 alkyl ester group Chemical group 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229920006351 engineering plastic Polymers 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 239000012796 inorganic flame retardant Substances 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 229920003192 poly(bis maleimide) Polymers 0.000 description 4
- 229920001643 poly(ether ketone) Polymers 0.000 description 4
- 229920001230 polyarylate Polymers 0.000 description 4
- 229920001955 polyphenylene ether Polymers 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000003856 thermoforming Methods 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- 229920001567 vinyl ester resin Polymers 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 3
- NQXNYVAALXGLQT-UHFFFAOYSA-N 2-[4-[9-[4-(2-hydroxyethoxy)phenyl]fluoren-9-yl]phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1C1(C=2C=CC(OCCO)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 NQXNYVAALXGLQT-UHFFFAOYSA-N 0.000 description 3
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 description 3
- 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 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 229920000459 Nitrile rubber Polymers 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 229930182556 Polyacetal Natural products 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- 239000004734 Polyphenylene sulfide Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
- 125000004036 acetal group Chemical group 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 3
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical compound OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 239000012765 fibrous filler Substances 0.000 description 3
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004898 kneading Methods 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 150000004767 nitrides Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000004745 nonwoven fabric Substances 0.000 description 3
- 229920006111 poly(hexamethylene terephthalamide) Polymers 0.000 description 3
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- 229920000069 polyphenylene sulfide Polymers 0.000 description 3
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- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000008929 regeneration Effects 0.000 description 3
- 238000011069 regeneration method Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
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- 239000004416 thermosoftening plastic Substances 0.000 description 3
- 229960000834 vinyl ether Drugs 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- RVHSTXJKKZWWDQ-UHFFFAOYSA-N 1,1,1,2-tetrabromoethane Chemical compound BrCC(Br)(Br)Br RVHSTXJKKZWWDQ-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 2
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 2
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- GGANEIOSDSVALY-UHFFFAOYSA-N 4-[9-(2,3,4-trihydroxyphenyl)fluoren-9-yl]benzene-1,2,3-triol Chemical class OC1=C(C=CC(=C1O)O)C1(C2=CC=CC=C2C=2C=CC=CC12)C1=C(C(=C(C=C1)O)O)O GGANEIOSDSVALY-UHFFFAOYSA-N 0.000 description 2
- NUDSREQIJYWLRA-UHFFFAOYSA-N 4-[9-(4-hydroxy-3-methylphenyl)fluoren-9-yl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C)C(O)=CC=2)=C1 NUDSREQIJYWLRA-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- 229920002943 EPDM rubber Polymers 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 description 2
- 229920002430 Fibre-reinforced plastic Polymers 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 229920003189 Nylon 4,6 Polymers 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 229920002302 Nylon 6,6 Polymers 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 239000004696 Poly ether ether ketone Substances 0.000 description 2
- 239000004962 Polyamide-imide Substances 0.000 description 2
- 239000004695 Polyether sulfone Substances 0.000 description 2
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Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Description
前記式(1)において、非反応性基は、例えば、アルキル基、アリール基、アラルキル基などであり、反応性基は、例えば、ヒドロキシル基、アミノ基、これらの活性水素から誘導される基などであってもよい。フルオレン骨格を有する化合物は、熱可塑性樹脂や熱硬化性樹脂などであってもよく、例えば、前記式(1)で表される化合物を単量体成分として重合した樹脂(例えば、ポリエステル系樹脂、ポリウレタン系樹脂、ポリカーボネート系樹脂、アクリル系樹脂、ポリイミド系樹脂など)であってもよい。前記相溶化剤は、さらに、アイオノマー系化合物、反応性基又は官能性基を含有する化合物、エラストマー系化合物などの相溶化剤を含んでいてもよい。
本発明の相溶化剤は、フルオレン骨格を有する化合物で構成されている。フルオレン骨格を有する化合物は、フルオレン骨格を有する限り特に限定されないが、通常、9,9−ビスフェニルフルオレン骨格を有する化合物が使用され、例えば、前記式(1)で表される化合物又はその誘導体が用いられる。
(1a)9,9−ビス(ヒドロキシフェニル)フルオレン類には、9,9−ビス(モノヒドロキシフェニル)フルオレン類、9,9−ビス(ジヒドロキシフェニル)フルオレン類、9,9−ビス(トリヒドロキシフェニル)フルオレン類などが含まれる。
9,9−ビス(ヒドロキシフェニル)フルオレン類のアルキレンオキシド付加体としては、前記例示のビス(モノ乃至トリヒドロキシフェニル)フルオレン類にアルキレンオキシド(C2-4アルキレンオキシド、特にC2-3アルキレンオキシド)が付加した化合物が挙げられる。アルキレンオキシド単位の付加数(前記式におけるk)は、前記と同様(例えば、1〜12、好ましくは1〜8、さらに好ましくは1〜6、特に1〜4程度)であり、特に限定されないが、以下に、一例として、kが1又は2の化合物を例示する。
9,9−ビス(アミノフェニル)フルオレン類としては、前記9,9−ビス(ヒドロキシフェニル)フルオレン類に対応する化合物、すなわち、9,9−ビス(ヒドロキシフェニル)フルオレン類のヒドロキシル基が、アミノ基又はN−置換アミノ基である化合物などが挙げられる。
フルオレン骨格を有する化合物を重合成分として含むポリエステル系樹脂(特に、フルオレン骨格を有する化合物を樹脂の単量体成分として重合したポリエステル系樹脂)は、少なくともヒドロキシル基を有するフルオレン化合物(前記9,9−ビス(ヒドロキシフェニル)フルオレン類又はそのアルキレンオキシド付加体などのポリオール成分、特に、9,9−ビス(モノヒドロキシフェニル)フルオレン類又はそのアルキレンオキシド付加体などのジオール成分)と、ジカルボン酸成分との反応により得ることができ、ポリエステル系樹脂には、飽和又は不飽和ポリエステル系樹脂の他、芳香族ジカルボン酸を重合成分として用いたポリアリレート系樹脂も含まれる。
フルオレン骨格を有する化合物を重合成分(単量体成分)として含むポリウレタン系樹脂を構成するポリオール成分(ジオール成分)は、前記ヒドロキシル基を有するフルオレン化合物(9,9−ビス(モノヒドロキシフェニル)フルオレン類又はそのアルキレンオキシド付加体など)単独で構成してもよく、前記ヒドロキシル基を有するフルオレン化合物と共に、前記ポリエステル系樹脂の項で例示のジオール類と併用してもよい。さらに、前記ヒドロキシル基を有するフルオレン化合物を構成単位として含むジオール成分、例えば、9,9−ビス(モノヒドロキシフェニル)フルオレン類で構成されたジオール成分とジカルボン酸成分との反応により生成するポリエステルジオール、9,9−ビス(モノヒドロキシフェニル)フルオレン類で構成されたジオール成分とアルキレンオキサイドとの反応により生成するポリエーテルジオールなども、ポリウレタン系樹脂のジオール成分として利用できる。ジオール成分も単独で又は二種以上組み合わせて使用できる。なお、必要であれば、ジオール成分は、トリオールなどのポリオール成分と併用してもよい。
フルオレン骨格を有する化合物を重合成分として含むポリカーボネート系樹脂としては、慣用の方法に従って、例えば、少なくとも前記ヒドロキシル基を有するフルオレン化合物(特に、9,9−ビス(モノヒドロキシフェニル)フルオレン類又はそのアルキレンオキシド付加体など)で構成されたポリオール成分(特に、ジオール成分)とホスゲンとの反応(ホスゲン法)、又は前記ヒドロキシル基を有するフルオレン化合物で構成されたポリオール成分(ジオール成分)と炭酸エステルとの反応(エステル交換法)により得られるポリカーボネート系樹脂が挙げられる。
アクリル系樹脂の単量体(フルオレン骨格を有する(メタ)アクリル系単量体)は、前記ヒドロキシル基を有するフルオレン化合物とカルボキシル基を有する重合性単量体との反応により得てもよい。カルボキシル基を有する重合性単量体としては、通常、不飽和モノカルボン酸、特に(メタ)アクリル酸が使用でき、桂皮酸、クロトン酸、ソルビン酸、マレイン酸モノアルキルエステル(モノメチルマレートなど)などを用いてもよい。さらに、不飽和カルボン酸に代えて、酸クロライド、C1-2アルキルエステルなどの反応性誘導体を使用してもよい。これらの単量体は、単独で又は二種以上組み合わせて使用してもよい。
ポリイミド系樹脂を構成するポリアミン成分(ジアミン成分)は、アミノ基を有するフルオレン化合物[前記9,9−ビス(アミノフェニル)フルオレン類など、特に、9,9−ビス(モノアミノフェニル)フルオレン類]を単独で用いてもよく、ジアミン成分(ジアミン類)と組み合わせて使用してもよい。ジアミン類としては、例えば、エチレンジアミン、ジエチレントリアミン、トリエチレンテトラミン、テトラエチレンペンタミン、ジプロピレンジアミン、ジエチルアミノプロピルアミン、ヘキサメチレンジアミン、ドデカンジアミンなどの鎖状C2-14脂肪族ポリアミン;メンセンジアミン、イソホロンジアミン、ジアミノジシクロヘキシルメタン、ビス(アミノメチル)シクロヘキサン、ビス(4−アミノ−3−メチルジシクロヘキシル)メタンなどの環状C6-14アミン;メタフェニレンジアミン、ジアミノジフェニルメタン、ジアミノジフェニルスルホン、ジアミノジエチルジフェニルメタンなどのC6-20芳香族ジアミン;m−キシリレンジアミンなどのC7-14芳香脂肪族ジアミン、ジアミノフェニルエーテル、2,2−ビス(3,4−ジアミノフェニル)プロパンなどのビス(ジアミノフェニル)アルカンなどが例示できる。ジアミン類は単独で又は二種以上組み合わせて使用できる。
本発明の相溶化剤は、混合する樹脂の種類に応じ、フルオレン骨格を有する化合物に加えて、さらに他の相溶化剤を含んでいてもよい。他の相溶化剤としては、(A)アイオノマー系化合物、(B)反応性基又は官能基を含有する化合物、(C)エラストマー系化合物などが挙げられる。これら他の相溶化剤は、単独で又は二種以上組み合わせて使用できる。これら他の相溶化剤と組み合わせると、樹脂の種類によっては、相溶化性及び得られるプラスチック材料の物性が向上する。
アイオノマー系化合物(A)としては、種々のタイプが含まれる。例えば、(a)ホスト高分子の主鎖に、部分的に側鎖イオン基が存在するタイプ(側鎖型)、(b)両末端にカルボン酸基などを有するホスト高分子又はオリゴマーに、金属イオンが中和することより高分子化したタイプ(テレケリック型)、(c)主鎖に陽イオンを有し、その陽イオンに陰イオンが結合したタイプ(アイオネン)などである。
反応性基又は官能基を含有する化合物(B)には、二重結合、カルボキシル基、エポキシ基、オキサゾリン基、アルコキシ基、アミノ基、メルカプト基、ビニル基、アセタール基、マレイン酸基、カルボキシル基などの反応性基又は官能基を有する化合物又はポリマーなどが含まれる。これらの化合物又はポリマーは、単独で又は二種以上組み合わせて使用できる。
エラストマー系相溶化剤(C)としては、例えば、スチレン系エラストマー(スチレン−ブタジエンブロック共重合体やスチレン−イソプレンブロック共重合体又はこれらの水添物など)などを好ましく使用できる。これらのエラストマー系相溶化剤(C)は、単独で又は二種以上組み合わせて使用できる。スチレン系エラストマーとしては、例えば、旭化成工業(株)製のタフテックなどが入手できる。
本発明の相溶化剤は、互いに相溶性のある複数種のポリマーに適用してもよいが、互いに非相溶な複数種のポリマーを相溶化するために用いるのが有効である。本発明の相溶化剤は、ポリマーの相溶化作用に優れ、例えば、難燃剤や無機フィラーが含まれていても、ポリマーアロイとしてのプラスチックの物性を低下させることなく、異種のポリマー同士を相溶化することができる。特に、少なくとも一種の使用済ポリマーを含む複数種のポリマーを用いてプラスチック材料を再生しても、実用的なプラスチック物性を確保できる。
このようなプラスチック材料は、各種成形体や、被覆又はコーティング剤、接着剤などとして利用できる。また、それぞれの用途に応じて、用いるポリマーの種類や配合量に応じて、前記相溶化剤の種類や量を、装置特性、生産性、要求される品質、物性に応じて適宜選択する必要がある。
廃PETフレーク(よのペットボトル(株)製)80重量部、PE製ガス管廃材ペレット(大阪樹脂工業(株)製)20重量部、及び相溶化剤として、フルオレン系ポリエステル(OKP4、大阪ガスケミカル(株)製)2重量部を、2軸押出機(BT−30−L、(株)プラスチック工学研究所製、L/D比=30)を用いて、以下の押出条件で溶融混練し、ストランド状に押し出し、チップを得た。
温度設定:フィード260℃、混練部300℃、ヘッド260℃
回転数:60rpm
得られたチップを射出成形機(N100BII、日本製鋼所(株)製、L/D比=22)を用いて、以下の成形条件で成形して、JIS K−6760に準拠した試験片(幅1/2インチ×長さ8.5インチ×厚み1/8インチ)を作製した。
温度設定:フィード 260℃、ノズル 280℃、金型 60℃
射出圧力:35〜40kg/cm2
この試験片について、JIS K−6760に準拠した機械的強度試験を行った結果、引張り降伏点強度は32MPaであった。
相溶化剤として、フルオレン系ポリエステル(OKP4、大阪ガスケミカル(株)製)1重量部及びエチレン−グリシジルメタクリレート共重合体(ボンドファーストE、住友化学(株)製)1重量部を用いた以外は、実施例1と同様にして試験片を作製した。引張り降伏点強度は36MPaであった。
相溶化剤として、フルオレン系ポリエステル(OKP4、大阪ガスケミカル(株)製)1重量部及びビスオキサゾリン−スチレン−無水マレイン酸共重合体(三国製薬(株)製)1重量部を用いた以外は、実施例1と同様にして試験片を作製した。引張り降伏点強度は34MPaであった。
相溶化剤として、フルオレン系ポリエステル(OKP4、大阪ガスケミカル(株)製)1重量部及びエチレン−(メタ)アクリル酸共重合体アイオノマー(ハイミラン1707Na、三井・デュポンポリケミカル(株)製)1重量部を用いた以外は、実施例1と同様にして試験片を作製した。引張り降伏点強度は34MPaであった。
相溶化剤を用いなかった以外は、実施例1と同様にして試験片を作製した。引張り降伏点強度は22MPaであった。
Claims (9)
- フルオレン骨格を有する化合物で構成された相溶化剤。
- 式(1)において、非反応性基が、アルキル基、アリール基又はアラルキル基であり、反応性基が、ヒドロキシル基、アミノ基、又はこれらの活性水素から誘導される基である請求項2記載の相溶化剤。
- フルオレン骨格を有する化合物が、熱可塑性樹脂又は熱硬化性樹脂である請求項1記載の相溶化剤。
- フルオレン骨格を有する化合物が、請求項2記載の式(1)で表される化合物を単量体成分として重合した樹脂であって、ポリエステル系樹脂、ポリウレタン系樹脂、ポリカーボネート系樹脂、アクリル系樹脂及びポリイミド系樹脂から選択された少なくとも一種の樹脂で構成されている請求項1記載の相溶化剤。
- さらに、アイオノマー系化合物、反応性基又は官能性基を有する化合物、及びエラストマー系化合物からなる群から選ばれる少なくとも1種の相溶化剤を含む請求項1記載の相溶化剤。
- 少なくとも一種の使用済ポリマーを含む複数種のポリマーと、請求項1記載の相溶化剤とで構成された再生プラスチック材料。
- さらに、難燃剤及び無機フィラーから選択された少なくとも一種を含む請求項7記載の再生プラスチック材料。
- 請求項7記載の再生プラスチック材料で形成された成形体。
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