JP2007091861A - Resin composition and regenerated resin - Google Patents
Resin composition and regenerated resin Download PDFInfo
- Publication number
- JP2007091861A JP2007091861A JP2005282357A JP2005282357A JP2007091861A JP 2007091861 A JP2007091861 A JP 2007091861A JP 2005282357 A JP2005282357 A JP 2005282357A JP 2005282357 A JP2005282357 A JP 2005282357A JP 2007091861 A JP2007091861 A JP 2007091861A
- Authority
- JP
- Japan
- Prior art keywords
- resin
- urethane
- decomposition
- polyalkylsiloxane
- acid
- 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
- 229920005989 resin Polymers 0.000 title claims abstract description 48
- 239000011347 resin Substances 0.000 title claims abstract description 48
- 239000011342 resin composition Substances 0.000 title claims description 14
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims abstract description 57
- 239000012948 isocyanate Substances 0.000 claims abstract description 16
- 238000000354 decomposition reaction Methods 0.000 claims description 80
- 239000003795 chemical substances by application Substances 0.000 claims description 49
- 229920005862 polyol Polymers 0.000 claims description 31
- 150000003077 polyols Chemical class 0.000 claims description 27
- 239000000126 substance Substances 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000003700 epoxy group Chemical group 0.000 claims description 13
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 10
- 229920001971 elastomer Polymers 0.000 claims description 8
- 239000002994 raw material Substances 0.000 claims description 8
- 239000000806 elastomer Substances 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract description 37
- 150000002513 isocyanates Chemical class 0.000 abstract description 14
- 239000004593 Epoxy Substances 0.000 abstract description 11
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract 1
- 239000004848 polyfunctional curative Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 60
- 229920000647 polyepoxide Polymers 0.000 description 38
- 239000003822 epoxy resin Substances 0.000 description 37
- 238000000034 method Methods 0.000 description 27
- -1 amine compound Chemical class 0.000 description 18
- 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 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 8
- 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 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 229920003986 novolac Polymers 0.000 description 6
- 239000002699 waste material Substances 0.000 description 5
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 4
- 238000011069 regeneration method Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical group ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical group O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 230000001172 regenerating effect Effects 0.000 description 3
- 230000008929 regeneration Effects 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 2
- 239000005059 1,4-Cyclohexyldiisocyanate Substances 0.000 description 2
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 2
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
- PBLZLIFKVPJDCO-UHFFFAOYSA-N 12-aminododecanoic acid Chemical compound NCCCCCCCCCCCC(O)=O PBLZLIFKVPJDCO-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- QZWKEPYTBWZJJA-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine-4,4'-diisocyanate Chemical compound C1=C(N=C=O)C(OC)=CC(C=2C=C(OC)C(N=C=O)=CC=2)=C1 QZWKEPYTBWZJJA-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-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
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Chemical group 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229920005830 Polyurethane Foam Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 238000002144 chemical decomposition reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000012774 insulation material Substances 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
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- 239000003550 marker Substances 0.000 description 2
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- TXXWBTOATXBWDR-UHFFFAOYSA-N n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCN(C)C TXXWBTOATXBWDR-UHFFFAOYSA-N 0.000 description 2
- DMQSHEKGGUOYJS-UHFFFAOYSA-N n,n,n',n'-tetramethylpropane-1,3-diamine Chemical compound CN(C)CCCN(C)C DMQSHEKGGUOYJS-UHFFFAOYSA-N 0.000 description 2
- 239000004843 novolac epoxy resin Substances 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000011146 organic particle Substances 0.000 description 2
- 239000011242 organic-inorganic particle Substances 0.000 description 2
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
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- 108090000765 processed proteins & peptides Proteins 0.000 description 2
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- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
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- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- XGIKILRODBEJIL-UHFFFAOYSA-N 1-(ethylamino)ethanol Chemical compound CCNC(C)O XGIKILRODBEJIL-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
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- 125000000623 heterocyclic group Chemical group 0.000 description 1
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- 150000004992 toluidines Chemical class 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
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- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
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- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
- Epoxy Resins (AREA)
Abstract
Description
本発明は、ウレタン樹脂の分解物を用いた樹脂組成物およびこれを硬化して製造した再生樹脂に関する。
The present invention relates to a resin composition using a decomposition product of a urethane resin and a recycled resin produced by curing the resin composition.
ウレタン樹脂は一般に自動車のシート、家具、マットレスなどのクッション材、断熱材、構造材、舗装材として広く用いられているが、３次元の網目構造を有する熱硬化性樹脂であるためにリサイクルが困難であり、現状では埋め立てや焼却などの処分がされている。
しかしながら、このような廃棄樹脂の処分方法には空間的あるいは環境維持の面で限界があり、効率的な処理方法の開発が望まれている。
Urethane resins are generally used widely as cushioning materials for automobile seats, furniture, mattresses, etc., heat insulating materials, structural materials, and paving materials, but are difficult to recycle because they are thermosetting resins with a three-dimensional network structure. At present, disposal such as landfill and incineration is being carried out.
However, the disposal method of such a waste resin has a limit in terms of space or environmental maintenance, and development of an efficient treatment method is desired.
一方、ウレタン樹脂を化学的手法で液化する方法が古くから研究されている。例えば、アルカノールアミンなどのアミン化合物でポリウレタンフォームを分解して、その後分解生成物を分離回収し、ウレタンフォームとして再生する方法や、分解剤としてポリオール及びアミノエタノールを用いてポリウレタンフォームを分解し、接着剤として再生する方法、他にもケトン／アルデヒド分解法、イソシアネート分解方法、熱分解方法、加水分解方法、後段昇温加熱法等が知られている。 On the other hand, methods for liquefying urethane resins by chemical methods have been studied for a long time. For example, the polyurethane foam is decomposed with an amine compound such as alkanolamine, and then the decomposition products are separated and recovered and regenerated as urethane foam, or the polyurethane foam is decomposed and bonded using polyol and aminoethanol as the decomposing agent. In addition, a method of regenerating as an agent, a ketone / aldehyde decomposition method, an isocyanate decomposition method, a thermal decomposition method, a hydrolysis method, a post-stage heating method, and the like are known.
また、このようにして分解して得られた分解生成物中のポリオールと、イソシアネートとを反応させてウレタン樹脂を再生する方法がある（特許文献１参照）。
前述したような分解方法で得られた分解物を特許文献１記載の再生方法に従って樹脂に再生すると、再生樹脂の機械特性、特に切断時伸びが低下し、表面が粘着性を有してべとつき、実用的ではないことがわかった。
本発明は、ウレタン分解物を樹脂に再生する際に、引張り強度・切断時伸び共に向上し、表面のべたつきを緩和する樹脂組成物およびこれを用いて製造した再生樹脂を提供することを目的とする。
When the decomposition product obtained by the decomposition method as described above is regenerated into a resin according to the regeneration method described in Patent Document 1, the mechanical properties of the regenerated resin, particularly the elongation at the time of cutting, is reduced, and the surface is sticky and sticky. It turned out to be impractical.
An object of the present invention is to provide a resin composition that improves both tensile strength and elongation at break and relieves surface stickiness when regenerating a urethane decomposition product into a resin, and a regenerated resin produced using the resin composition. To do.
第１の本発明は、（１）ウレタン樹脂を化学分解した分解物、（２）イソシアネート基またはエポキシ基を２以上有する硬化剤、（３）ポリアルキルシロキサンを含有することを特徴とする樹脂組成物である。 The first invention of the present invention comprises (1) a decomposition product obtained by chemically decomposing a urethane resin, (2) a curing agent having two or more isocyanate groups or epoxy groups, and (3) a polyalkylsiloxane. It is a thing.
前記第１の本発明において、前記ウレタン樹脂は、水酸基価が２５０ｍｇＫＯＨ／ｇ以下のポリオールを原料とするものであることが好ましい。 In the first aspect of the present invention, the urethane resin is preferably made from a polyol having a hydroxyl value of 250 mgKOH / g or less as a raw material.
前記ポリアルキルシロキサンは、下記化学式３の構造を有するものであることが好ましい。
上記化学式３において、Ｒは以下の化学式４に示す官能基を表す。
In the above chemical formula 3, R represents a functional group represented by the following chemical formula 4.
前記第１の本発明において、前記ポリアルキルシロキサンの含有量が、１．０ｐｐｍ以上５０００ｐｐｍ未満であることが好ましい。 In the first aspect of the present invention, the content of the polyalkylsiloxane is preferably 1.0 ppm or more and less than 5000 ppm.
前記第１の本発明において、前記硬化剤が、イソシアネートプレポリマーであることが好ましい。 In the first aspect of the present invention, the curing agent is preferably an isocyanate prepolymer.
第２の本発明は、（１）ウレタン樹脂を化学分解した分解物、（２）イソシアネート基またはエポキシ基を２以上有する硬化剤化合物、（３）ポリアルキルシロキサンを少なくとも原料とした樹脂硬化物であることを特徴とする再生樹脂である。 The second aspect of the present invention is (1) a decomposition product obtained by chemically decomposing a urethane resin, (2) a curing agent compound having two or more isocyanate groups or epoxy groups, and (3) a resin cured product using at least a polyalkylsiloxane as a raw material. It is a recycled resin characterized by being.
前記第２の本発明において、前記再生樹脂が、発泡倍率２倍以下のゴム弾性を有するエラストマー状であることが好ましい。
In the second aspect of the present invention, the recycled resin is preferably in the form of an elastomer having rubber elasticity with an expansion ratio of 2 times or less.
本発明により、引張り強度、切断時伸びが向上し、かつ表面のべたつきが緩和された再生樹脂を提供することが可能となる。
According to the present invention, it is possible to provide a recycled resin with improved tensile strength and elongation at break and with reduced surface stickiness.
本実施の形態の樹脂組成物は、ウレタン樹脂を化学的に分解した分解物、イソシアネート基またはエポキシ基を２以上有する硬化剤、ポリアルキルシロキサンを少なくとも含有するものであり、以下、これらの各成分について説明する。 The resin composition of the present embodiment contains a decomposition product obtained by chemically decomposing a urethane resin, a curing agent having two or more isocyanate groups or epoxy groups, and at least a polyalkylsiloxane. Will be described.
［ウレタン分解物］
このウレタン分解物は、硬質、軟質、半硬質、ゴム、エラストマー、ＲＩＭ、塗料、接着剤など各種のウレタン樹脂を、分解剤を用いて化学的に分解したものである。
原料として用いるウレタン樹脂としては、水酸基価が、２５０ｍｇＫＯＨ／ｇ以下のポリオールを原料として製造されたものが好ましい。原料のポリオールの水酸基価がこの範囲を超えた樹脂を分解して得たウレタン分解物を再生樹脂の原料として用いると、得られる再生樹脂の剛性が高く、機械的強度が不十分で実用的な再生樹脂が得られない。
[Urethane decomposition product]
This urethane decomposition product is obtained by chemically decomposing various urethane resins such as hard, soft, semi-rigid, rubber, elastomer, RIM, paint, adhesive and the like using a decomposition agent.
As the urethane resin used as a raw material, those produced using a polyol having a hydroxyl value of 250 mgKOH / g or less as a raw material are preferable. When a urethane decomposition product obtained by decomposing a resin whose hydroxyl value of the raw material polyol exceeds this range is used as a raw material for the recycled resin, the resulting recycled resin has high rigidity and insufficient mechanical strength and is practical. A recycled resin cannot be obtained.
このような原料ウレタン樹脂としては、例えば、冷蔵庫の断熱材、建築の断熱材、車のシートのウレタン、椅子のクッション材、ベッドマット、工業用鉄工ロール、ソリッドタイヤ、床材、舗装材、自動車のバンパーなど、各種形態の成型物を用いることができる。
本発明において、ウレタン樹脂の化学的な分解方法としては、一般的に知られているいかなるものでもよく、例えば、ポリオール分解、アミン分解、加水分解、酸分解などが挙げられる。
Such raw material urethane resins include, for example, refrigerator insulation materials, architectural insulation materials, car seat urethane, chair cushion materials, bed mats, industrial iron rolls, solid tires, flooring materials, paving materials, automobiles, etc. Various types of moldings such as bumpers can be used.
In the present invention, the chemical decomposition method of the urethane resin may be any generally known method, and examples thereof include polyol decomposition, amine decomposition, hydrolysis, and acid decomposition.
（分解剤）
ウレタン樹脂の化学的分解において使用される分解剤としては、上記分解方法によって異なるが、例えば、ヒドロキシル基、アミノ基、水、カルボキシル基及びその誘導体、エポキシ基、イソシアネート基含有化合物などの分解剤を用いることができる。
(Decomposing agent)
The decomposing agent used in the chemical decomposition of the urethane resin varies depending on the decomposing method. For example, decomposing agents such as hydroxyl group, amino group, water, carboxyl group and derivatives thereof, epoxy group, and isocyanate group-containing compounds are used. Can be used.
以下に、分解剤について具体例を挙げる。
・ヒドロキシル基含有分解剤
ヒドロキシル基を含有する分解剤としては、例えばエチレングリコール、プロピレングリコール、ジエチレングリコール、ジプロピレングリコール、グリセリン、トリメチロールプロパン、１，２，６−ヘキサントリオール、トリエタノールアミン、ペンタエリスリトール、エチレンジアミン、トリレンジアミン、ジフェニルメタンジアミンテトラメチロールシクロヘキサン、メチルグルコシド等が挙げられる。
Specific examples of the decomposition agent are given below.
・ Hydroxyl group-containing decomposing agent Examples of the decomposing agent containing a hydroxyl group include ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, glycerin, trimethylolpropane, 1,2,6-hexanetriol, triethanolamine, and pentaerythritol. , Ethylenediamine, tolylenediamine, diphenylmethanediaminetetramethylolcyclohexane, methylglucoside and the like.
ヒドロキシル基含有分解剤を、被分解物であるウレタン樹脂１００重量部に対し５重量部以上、より好ましくは１０重量部以上用いることが望ましい。上限はウレタン樹脂１００重量部に対し１００重量部以下、より好ましくは４０重量部以下であることが望ましい。 It is desirable that the hydroxyl group-containing decomposing agent is used in an amount of 5 parts by weight or more, more preferably 10 parts by weight or more with respect to 100 parts by weight of the urethane resin that is a decomposition target. The upper limit is preferably 100 parts by weight or less, more preferably 40 parts by weight or less with respect to 100 parts by weight of the urethane resin.
・アミノ基含有分解剤
アミノ基を有する分解剤としては、モノエタノールアミン、ジエタノールアミン、トリエタノールアミン、エチレンジアミン、テトラメチレンジアミン、ヘキサメチレンジアミン、プロパンジアミン、２−エチルヘキシルアミン、イソプロパノールアミン、２−（２−アミノエチルアミノ）エタノール、２−アミノ−２−ヒドロキシメチル−１，３−プロパンジオール、エチルアミノエタノール、アミノブタノール、ｎ−プロピルアミン、ジ−ｎ−プロピルアミン、ｎ−アミルアミン、イソブチルアミン、メチルジエチルアミン、シクロヘキシルアミン、ピペラジン、ピペリジン、アニリン、トルイジン、ベンジルアミン、フェニレンジアミン、キシリレンジアミン、クロロアニリン、ピリジン、ピコリン、Ｎ−メチルモルフォリン、エチルモルフォリン、ピラゾール、１，４−ジアミノブタン、１２−アミノドデカン酸、２−ヒドロキシエチルアミノプロピルアミン、３−（２−エチルヘキシルオキシ）プロピルアミン、３−（ジエチルアミノ）プロピルアミン、３−（ジブチルアミノ）プロピルアミン、３−（ジメチルアミノ）プロピルアミン、３−（メチルアミノ）プロピルアミン、３，３’−イミノビス（プロピルアミン）、３−アミノ−１−プロパノール、３−アミノクロトン酸メチル、３−メトキシプロピルアミン、Ｎ−（２−アミノエチル）エタノールアミン、Ｎ，Ｎ，Ｎ’，Ｎ’−テトラメチル−１，６−ヘキサメチレンジアミン、Ｎ，Ｎ−ジイソプロピルエチルアミン、Ｎ，Ｎ−ジエチルエタノールアミン、Ｎ，Ｎ−ジメチルエタノールアミン、Ｎ，Ｎ−ブチルエタノールアミン、Ｎ−エチルエチレンジアミン、ｎ−ヘキシルアミン、Ｎ−メチル−３，３’−イミノビス（プロピルアミン）、Ｎ−メチルエタノールアミン、Ｎ−メチルジエタノールアミン、ｓｅｃ−ブチルアミン、ｔ−ブチルアミン、アリルアミン、イソプロピルアミン、エチルアミン、ジ−２−エチルヘキシルアミン、ジ−ｎ−オクチルアミン、ジアリルアミン、ジイソブチルアミン、ジイソプロパノールアミン、ジイソプロピルアミン、ジエチルアミン、ジエチルヒドロキシルアミン、ジエチレントリアミン、ジシクロヘキシルアミン、ジブチルアミン、ジメチルアミン、テトラエチレンペンタミン、テトラメチル−１，３−ジアミノプロパン、テトラメチルエチレンジアミン、トリ−ｎ−オクチルアミン、トリアリルアミン、トリイソプロパノールアミン、トリエチルアミン、トリエチレンテトラミン、トリブチルアミン、トリメチルアミン、ヘキサメチレンジアミン、ペンタエチレンヘキサミン、ペンタメチルジエチレントリアミン、モノブチルアミン、モノメチルアミンがあげられる。これらの化合物を混合して使用しても問題はない。
-Amino group-containing decomposition agent Examples of the decomposition agent having an amino group include monoethanolamine, diethanolamine, triethanolamine, ethylenediamine, tetramethylenediamine, hexamethylenediamine, propanediamine, 2-ethylhexylamine, isopropanolamine, 2- (2 -Aminoethylamino) ethanol, 2-amino-2-hydroxymethyl-1,3-propanediol, ethylaminoethanol, aminobutanol, n-propylamine, di-n-propylamine, n-amylamine, isobutylamine, methyl Diethylamine, cyclohexylamine, piperazine, piperidine, aniline, toluidine, benzylamine, phenylenediamine, xylylenediamine, chloroaniline, pyridine, picoline, N-methyl Morpholine, ethylmorpholine, pyrazole, 1,4-diaminobutane, 12-aminododecanoic acid, 2-hydroxyethylaminopropylamine, 3- (2-ethylhexyloxy) propylamine, 3- (diethylamino) propylamine, 3 -(Dibutylamino) propylamine, 3- (dimethylamino) propylamine, 3- (methylamino) propylamine, 3,3'-iminobis (propylamine), 3-amino-1-propanol, 3-aminocrotonic acid Methyl, 3-methoxypropylamine, N- (2-aminoethyl) ethanolamine, N, N, N ′, N′-tetramethyl-1,6-hexamethylenediamine, N, N-diisopropylethylamine, N, N -Diethylethanolamine, N, N-dimethylethanolamine N, N-butylethanolamine, N-ethylethylenediamine, n-hexylamine, N-methyl-3,3′-iminobis (propylamine), N-methylethanolamine, N-methyldiethanolamine, sec-butylamine, t- Butylamine, allylamine, isopropylamine, ethylamine, di-2-ethylhexylamine, di-n-octylamine, diallylamine, diisobutylamine, diisopropanolamine, diisopropylamine, diethylamine, diethylhydroxylamine, diethylenetriamine, dicyclohexylamine, dibutylamine, dimethyl Amine, tetraethylenepentamine, tetramethyl-1,3-diaminopropane, tetramethylethylenediamine, tri-n-octylamine, tria Triethanolamine, triisopropanolamine, triethylamine, triethylenetetramine, tributylamine, trimethylamine, hexamethylenediamine, pentaethylenehexamine, pentamethyl diethylenetriamine, mono-butyl amines, monomethyl amine. There is no problem even if these compounds are mixed and used.
アミン類分解剤を被分解物であるウレタン樹脂１００重量部に対し５重量部以上、より好ましくは１０重量部以上用いることが望ましい。上限はウレタン樹脂１００重量部に対し１００重量部以下、より好ましくは４０重量部以下であることが望ましい。 It is desirable to use 5 parts by weight or more, more preferably 10 parts by weight or more with respect to 100 parts by weight of the urethane resin as a decomposition target, for the amine decomposition agent. The upper limit is preferably 100 parts by weight or less, more preferably 40 parts by weight or less with respect to 100 parts by weight of the urethane resin.
・カルボキシル基及びその誘導体含有分解剤
カルボキシル基の誘導体とは、カルボキシル基の塩やエステル、又は酸無水物などを挙げることができる。
-Carboxyl group and its derivative containing decomposition agent The derivative of a carboxyl group can mention the salt and ester of a carboxyl group, or an acid anhydride.
カルボキシル基及びその誘導体を含有する分解剤としては、具体的には、蟻酸、酢酸、プロピオン酸、酪酸、イソ酪酸、イタコン酸、プロピオール酸、オレイン酸、アクリル酸、メタクリル酸、シュウ酸、マレイン酸、フマル酸、フタル酸、イタコン酸、マロン酸、琥珀酸、アジピン酸、安息香酸、シトラコン酸、クロトン酸、グルタル酸、ヘキサン酸、グリコール酸、乳酸、リンゴ酸、酒石酸、クエン酸、糖酸、グリセリン酸、グルコン酸、サリチル酸、トリメリット酸、シクロペンタンテトラカルボンメチルヘキサヒドロフタル酸、ヘキサヒドロフタル酸、およびこれらの酸無水物やラクトンなどの分子内脱水をしている有機酸などである。また、無水トリメリット酸のように、分子内にカルボキシル基と酸無水物を併せ持つ化合物であっても差し支えない。更にナトリウム塩、カリウム塩、カルシウム塩などに代表されるこれら有機酸の塩、及び酢酸メチル、酢酸エチル、酢酸プロピルなどに代表されるこれら有機酸と水酸基を有する物質とのエステルが挙げられる。さらには、グリシン、アラニン、バリン、ロイシン、イソロイシン、グルタミン、セリン、フェニルアラニン、グルタミン酸などのアミノ酸も利用できる。これらが複数結合しているものや、プロリンなどの分子内結合をしているイミノ酸などでも構わない。これらの化合物の光学異性体においても全く同様に使用することができる。 Specific examples of the decomposing agent containing a carboxyl group and derivatives thereof include formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, itaconic acid, propiolic acid, oleic acid, acrylic acid, methacrylic acid, oxalic acid, maleic acid , Fumaric acid, phthalic acid, itaconic acid, malonic acid, succinic acid, adipic acid, benzoic acid, citraconic acid, crotonic acid, glutaric acid, hexanoic acid, glycolic acid, lactic acid, malic acid, tartaric acid, citric acid, sugar acid, Examples thereof include glyceric acid, gluconic acid, salicylic acid, trimellitic acid, cyclopentanetetracarboxylicmethylhexahydrophthalic acid, hexahydrophthalic acid, and organic acids that have undergone intramolecular dehydration such as acid anhydrides and lactones thereof. Further, it may be a compound having both a carboxyl group and an acid anhydride in the molecule, such as trimellitic anhydride. Further, salts of these organic acids typified by sodium salt, potassium salt, calcium salt and the like, and esters of these organic acids typified by methyl acetate, ethyl acetate, propyl acetate and the like with a substance having a hydroxyl group can be mentioned. Furthermore, amino acids such as glycine, alanine, valine, leucine, isoleucine, glutamine, serine, phenylalanine, and glutamic acid can also be used. A plurality of these may be bonded, or an imino acid having an intramolecular bond such as proline may be used. These optical isomers of these compounds can be used in the same manner.
カルボキシル基およびその誘導体含有分解剤を、被分解物であるウレタン樹脂１００重量部に対し５重量部以上、より好ましくは１０重量部以上用いることが望ましい。上限はウレタン樹脂１００重量部に対し１００重量部以下、より好ましくは４０重量部以下であることが望ましい。 It is desirable to use the carboxyl group and its derivative-containing decomposing agent in an amount of 5 parts by weight or more, more preferably 10 parts by weight or more with respect to 100 parts by weight of the urethane resin that is a decomposition target. The upper limit is preferably 100 parts by weight or less, more preferably 40 parts by weight or less with respect to 100 parts by weight of the urethane resin.
・エポキシ基含有分解剤
エポキシ基を有する分解剤としては、エチレンオキサイド、プロピレンオキサイド、ブチルグリシジルエーテル、アリルグリシジルエーテル、アリル２，３−エポキシプロピルエーテル、ベンジルグリシジルエーテル、ブタンジオールジグリシジルエーテル、ブチル２，３−エポキシプロピルエーテル、エチレングリコールジグリシジルエーテル、フェニルグリシジルエーテル、１，２−エポキシエチルベンゼン、２，３−エポキシ−１−プロパノール、２，３−エポキシプロピルメチルエーテルなどのものから、一般にエポキシ樹脂として知られているビスフェノールＡ型エポキシ樹脂、ビスフェノールＦ型エポキシ樹脂、フェノールノボラック型エポキシ樹脂、クレゾールノボラック型エポキシ樹脂、ナフトール系のノボラック型エポキシ樹脂、ビスフェノールＡのノボラック型エポキシ樹脂、ナフタレンジオール型エポキシ樹脂、脂環式エポキシ樹脂、トリまたはテトラ（ヒドロキシフェニル）アルカンから誘導されるエポキシ樹脂、ビスヒドロキシビフェニル系エポキシ樹脂、フェノールアラルキル樹脂のエポキシ化物などが挙げられる。
-Epoxy group-containing decomposing agent As the decomposing agent having an epoxy group, ethylene oxide, propylene oxide, butyl glycidyl ether, allyl glycidyl ether, allyl 2,3-epoxypropyl ether, benzyl glycidyl ether, butanediol diglycidyl ether, butyl 2 , 3-epoxypropyl ether, ethylene glycol diglycidyl ether, phenyl glycidyl ether, 1,2-epoxyethylbenzene, 2,3-epoxy-1-propanol, 2,3-epoxypropyl methyl ether, etc. Bisphenol A type epoxy resin, bisphenol F type epoxy resin, phenol novolac type epoxy resin, cresol novolac type epoxy resin, naphthol Novolac epoxy resin, bisphenol A novolac epoxy resin, naphthalenediol epoxy resin, alicyclic epoxy resin, epoxy resin derived from tri- or tetra (hydroxyphenyl) alkane, bishydroxybiphenyl epoxy resin, phenol Examples include epoxidized aralkyl resins.
エポキシ基含有分解剤を被分解物であるウレタン樹脂１００重量部に対し５重量部以上、より好ましくは１０重量部以上用いることが望ましい。上限はウレタン樹脂１００重量部に対し１００重量部以下、より好ましくは４０重量部以下であることが望ましい。 It is desirable to use the epoxy group-containing decomposing agent in an amount of 5 parts by weight or more, more preferably 10 parts by weight or more with respect to 100 parts by weight of the urethane resin that is the decomposition target. The upper limit is preferably 100 parts by weight or less, more preferably 40 parts by weight or less with respect to 100 parts by weight of the urethane resin.
・イソシアネート基含有分解剤
イソシアネート基含有分解剤としては、フェニルイソシアネートなどのモノイソシアネート化合物や、ジフェニルメタンジイソシアネート（ＭＤＩ）、トリレンジイソシアネート（ＴＤＩ）、キシリレンジイソシアネート、テトラメチルキシリレンジイソシアネート、３−イソシアナトメチル−３，５，５−トリメチルシクロヘキシルイソシアネート、４，４’−メチレンビス（シクロヘキシルイソシアネート）、ビス（イソシアナトメチル）シクロヘキサン、ヘキサメチレンジイソシアネートなどのイソシアネート基を複数持つ化合物、またポリメリックＭＤＩなどの高分子化した化合物を用いることができる。
また、前述した各種の分解剤は単独、あるいは２種類以上混合して使用してもよい。
-Isocyanate group-containing decomposer As isocyanate group-containing decomposer, monoisocyanate compounds such as phenyl isocyanate, diphenylmethane diisocyanate (MDI), tolylene diisocyanate (TDI), xylylene diisocyanate, tetramethyl xylylene diisocyanate, 3-isocyanato Compounds having a plurality of isocyanate groups such as methyl-3,5,5-trimethylcyclohexyl isocyanate, 4,4′-methylenebis (cyclohexyl isocyanate), bis (isocyanatomethyl) cyclohexane, hexamethylene diisocyanate, and polymers such as polymeric MDI The compound can be used.
Moreover, you may use the various decomposition agent mentioned above individually or in mixture of 2 or more types.
イソシアネート含有分解剤を、被分解物であるウレタン樹脂１００重量部に対し５重量部以上、より好ましくは１０重量部以上用いることが望ましい。上限はウレタン樹脂１００重量部に対し１００重量部以下、より好ましくは４０重量部以下であることが望ましい。 It is desirable to use the isocyanate-containing decomposing agent in an amount of 5 parts by weight or more, more preferably 10 parts by weight or more with respect to 100 parts by weight of the urethane resin that is a decomposition target. The upper limit is preferably 100 parts by weight or less, more preferably 40 parts by weight or less with respect to 100 parts by weight of the urethane resin.
（分解触媒）
上記分解剤を使用する分解反応において、必要に応じて、上記ウレタン樹脂及び分解剤に分解触媒を添加し、分解速度を上げることができる。
(Decomposition catalyst)
In the decomposition reaction using the above decomposition agent, if necessary, a decomposition catalyst can be added to the urethane resin and the decomposition agent to increase the decomposition rate.
添加する触媒としては、ウレタンの生成時に使われるものが好ましく、例えば、トリエチルアミン、Ｎ，Ｎ−ジメチルシクロヘキシルアミン、Ｎ，Ｎ，Ｎ’，Ｎ’−テトラメチルエチレンジアミン、Ｎ，Ｎ，Ｎ’，Ｎ’−テトラメチルプロパン１，３−ジアミン、Ｎ，Ｎ，Ｎ’，Ｎ’−テトラメチルヘキサン１，６−ジアミン、Ｎ，Ｎ，Ｎ’，Ｎ”，Ｎ”−ペンタメチルジエチレントリアミン、Ｎ，Ｎ，Ｎ’，Ｎ”，Ｎ”−ペンタメチルジプロピレントリアミン、テトラメチルグアニジン、トリエチレンジアミン、Ｎ，Ｎ’−ジメチルピペラジン、Ｎ，−メチル，Ｎ’−（２−ジメチルアミノ）エチルピペラジン、Ｎ−メチルモルホリン、Ｎ−（Ｎ’，Ｎ’−ジメチルアミノエチル）−モルホリン、１，２−ジメチルイミダゾール、ヘキサメチレンテトラミン、ジメチルアミノエタノール、ジメチルアミノエトキシエタノール、Ｎ，Ｎ，Ｎ’−トリメチルアミノエチルエタノールアミン、Ｎ−メチル−Ｎ’−（２−ヒドロキシエチル）−ピペラジン、Ｎ−（２−ヒドロキシエチル）モルホリン、ビス（２−ジメチルアミノエチル）エーテル、エチレングリコールビス（３−ジメチル）−アミノプロピルエーテル、スタナスオクトエート、ジブチルチンジアセテート、ジブチルチンジラウレート、ジブチルチンマーカプチド、ジブチルチンチオカルボキシレート、ジブチルインジマレエート、ジオクチルチンマーカプチド、ジオクチルチンチオカルボキシレート、オクテン酸鉛、オクテン酸カリウムなどが挙げられる。 As the catalyst to be added, those used in the production of urethane are preferable. For example, triethylamine, N, N-dimethylcyclohexylamine, N, N, N ′, N′-tetramethylethylenediamine, N, N, N ′, N '-Tetramethylpropane 1,3-diamine, N, N, N', N'-tetramethylhexane 1,6-diamine, N, N, N ', N ", N" -pentamethyldiethylenetriamine, N, N , N ′, N ″, N ″ -pentamethyldipropylenetriamine, tetramethylguanidine, triethylenediamine, N, N′-dimethylpiperazine, N, -methyl, N ′-(2-dimethylamino) ethylpiperazine, N— Methylmorpholine, N- (N ′, N′-dimethylaminoethyl) -morpholine, 1,2-dimethylimidazole, hexame Lentetamine, dimethylaminoethanol, dimethylaminoethoxyethanol, N, N, N′-trimethylaminoethylethanolamine, N-methyl-N ′-(2-hydroxyethyl) -piperazine, N- (2-hydroxyethyl) morpholine , Bis (2-dimethylaminoethyl) ether, ethylene glycol bis (3-dimethyl) -aminopropyl ether, stannous octoate, dibutyltin diacetate, dibutyltin dilaurate, dibutyltin marker peptide, dibutyltin thiocarboxylate, dibutylindi Examples include maleate, dioctyltin marker peptide, dioctyltin thiocarboxylate, lead octenoate, and potassium octenoate.
分解触媒の添加量は分解剤１００重量部に対し０．０１重量部以上１０重量部以下が好ましく、さらに好ましくは０．１重量部以上５重量部以下がよい。１０重量部より分解剤の量が多いと、再生時に反応の制御が難しいので好ましくなく、０．０１重量部以下では十分に触媒の効果が得られないことがある。 The addition amount of the decomposition catalyst is preferably 0.01 parts by weight or more and 10 parts by weight or less, and more preferably 0.1 parts by weight or more and 5 parts by weight or less with respect to 100 parts by weight of the decomposition agent. When the amount of the decomposing agent is more than 10 parts by weight, it is not preferable because it is difficult to control the reaction at the time of regeneration.
（分解条件）
分解方法は、ウレタン樹脂と分解剤との混合物を加熱・攪拌する方法であれば特に限定するものではなく、バッチ式、連続式にかかわらず使用できる。
連続式の方法とは、加熱された流路にウレタン樹脂を流す手法であり、例えば円筒体中に、円筒と同軸の螺旋状の攪拌子を設置した押出機などの連続装置に分解剤と共にウレタン樹脂を投入し、円筒を加熱するとともに、螺旋状の攪拌子を回転させてウレタン樹脂（及び／又は分解物）を円筒中を移動させることで、ウレタン樹脂を混錬しながら連続的に分解処理することができる。連続式の分解方法においては、ウレタン樹脂や分解剤の種類によって多少異なるが、通常出口樹脂温度が８０℃〜３００℃、になるように、また滞留時間（円筒中の通過に要する時間）は１分以上となるように設定して行えばよい。ここで、出口樹脂温度とは、連続装置における出口での減容化物の温度である。なお、押出機を用いた分解は、樹脂が混錬されるため、微量の分解剤をウレタン樹脂に均一に接触でき、また、ウレタン樹脂の加熱も均一に行われるため、短時間で、均一な分解物を得ることが可能になる。
(Disassembly conditions)
The decomposition method is not particularly limited as long as it is a method of heating and stirring a mixture of a urethane resin and a decomposition agent, and can be used regardless of a batch type or a continuous type.
The continuous method is a method in which a urethane resin is caused to flow through a heated flow path. For example, urethane together with a decomposition agent is added to a continuous device such as an extruder in which a helical stirrer coaxial with a cylinder is installed in a cylindrical body. The resin is charged, the cylinder is heated, and the spiral stirrer is rotated to move the urethane resin (and / or decomposed product) through the cylinder, thereby continuously decomposing the urethane resin while kneading. can do. In the continuous decomposition method, although it differs somewhat depending on the type of the urethane resin and the decomposition agent, the outlet resin temperature is usually 80 ° C. to 300 ° C., and the residence time (time required for passage through the cylinder) is 1. What is necessary is just to set so that it may become more than minutes. Here, the outlet resin temperature is the temperature of the volume-reduced product at the outlet in the continuous device. In addition, since the resin is kneaded in the decomposition using an extruder, a small amount of a decomposing agent can be uniformly contacted with the urethane resin, and the urethane resin is also heated uniformly. A decomposition product can be obtained.
バッチ式の方法とは、反応容器内で分解剤とウレタン樹脂を所定時間攪拌しながら加熱処理する方法である。加熱温度は通常設定温度が８０〜３００℃とし、１０分〜３時間程加熱処理を行えばよい。 The batch method is a method in which a decomposition agent and a urethane resin are heated in a reaction vessel while stirring for a predetermined time. The heating temperature is usually set to 80 to 300 ° C., and the heat treatment may be performed for about 10 minutes to 3 hours.
［ポリアルキルシロキサン］
本発明の再生樹脂の製造に使用されるポリアルキルシロキサンは下記化学式５で示される構造を有するものである。
[Polyalkylsiloxane]
The polyalkylsiloxane used in the production of the recycled resin of the present invention has a structure represented by the following chemical formula 5.
ここで、Ｒは水素原子や、アルキル基、置換アルキル基、芳香族基などの官能基であればよく、具体的には下記化学式６で示される基が挙げられる。
Here, R may be a functional group such as a hydrogen atom, an alkyl group, a substituted alkyl group, or an aromatic group, and specifically includes a group represented by the following chemical formula 6.
前記Ｒは、より好ましくはメチル基あるいはフェニル基である。また、前記化学式５において、Ｒは全て同一であってもよいし、Ｒが異なる２種以上の基であってもよい。前記Ｒが異なる２種以上の基である場合には、そのポリアルキルシロキサンは、単独重合体であってもよいし、下記化学式７で示されるブロック共重合体であってもよい。
本実施の形態において、重合度、すなわち、前記化学式２におけるｎ、あるいは下記化学式におけるｎ＋ｍの値は、５０以下とすることができるが、好ましくは、重合度は１〜２０である。重合度が、この範囲を上回ると、常温で粘性が非常に高くなり、樹脂組成物への均一分散が困難となる。
R is more preferably a methyl group or a phenyl group. Moreover, in the said Chemical formula 5, all R may be the same and 2 or more types of groups from which R differs may be sufficient. When R is two or more groups different from each other, the polyalkylsiloxane may be a homopolymer or a block copolymer represented by the following chemical formula 7.
In the present embodiment, the degree of polymerization, that is, the value of n in the chemical formula 2 or the value of n + m in the following chemical formula can be 50 or less. When the degree of polymerization exceeds this range, the viscosity becomes very high at room temperature, and uniform dispersion in the resin composition becomes difficult.
上記ポリアルキルシロキサンとしては、具体的には、重合度１ないし２０のジメチルポリシロキサン、ジフェニルポリシロキサン、ポリメチルフェニルシロキサン、ポリメチルエポキプロピルシロキサン、ポリメチルアミノプロピルシロキサンなどが挙げられる。商品例としては、ＴＳＦ４５１，ＴＨＦ４５０，ＦＱＦ５０１，ＹＳＡ６４０３，ＴＳＡ７２０，ＹＳＡ０２，ＴＳＡ７５０，ＴＳＡ７５０Ｓ，ＹＳＡ６４０６，ＴＳＡ７８０，ＴＳＡ７３４１，ＴＳＡ７３９，ＴＳＡ７３２，ＴＳＡ７３２Ａ，ＴＳＡ７７２，ＴＳＡ７３０，ＴＳＡ７７０，ＴＳＡ７７５，ＹＭＡ６５０９，ＴＳＡ７３７Ｂ，ＴＳＡ７３７Ｓ，ＴＳＡ７３７Ｆ（以上ＧＥ東芝シリコーン社製），ＫＭ−７３，ＫＭ−７３Ａ，ＫＭ−７３Ｅ，ＫＭ−７０，ＫＭ−７１，ＫＭ−７５，ＫＭ−８５，ＫＭ−７２，ＫＭ−７２Ｆ，ＫＭ−７２Ｓ，ＫＭ−７２ＦＳ，ＫＭ−８９，ＫＭ−９０，ＫＭ−９８，ＫＭ−６８−１Ｆ，ＫＳ−５０８，ＫＳ−５３０，ＫＳ−５３１，ＫＳ−５３７，ＫＳ−５３８，ＫＳ−６６，ＫＳ−６９，ＫＦ−９６，ＫＳ−６０４，ＫＳ−６７０２，ＦＡ−６３０，ＫＳ−６０２Ａ，ＫＳ−６０３，ＦＡ−６００，ＫＭ−８８Ｐ，ＫＭ−９１Ｐ，ＫＭ−６０１Ｓ（以上、信越シリコーン社製），ＳＨ２００，ＳＨ２０３，ＦＳ１２６５，ＳＨ５５００，ＳＣ５５４０，ＢＹ２８−５０３，ＳＨ７ＰＡ，ＳＨ５５１０，ＳＨ５５６１，ＳＨ５５０７，ＳＨ８７３０，ＳＭ５５１１，ＳＭ５５７１，ＳＭ５５１５，ＳＭ５５１２，ＤＣ２００，ＦＳ１２６５，ＤＣ７１，ＤＣ７４，ＤＢ−１００，Ｆ−１６，ＤＣ７５，１２６６，１２８３，ＤＫＱ１−１１８３，ＤＫＱ１−１０８６，ＤＫＱ１−０７１，８０，５４４，ＥＰＬ，０２５，１２２４，１２３３，ＤＫＱ１−１２４７，０１３Ａ，１２７７，ＣＥ，Ｃ−Ｅｍｕｌｓｉｏｎ，ＡＦＥ，９２，９３，ＤＢ−１１０Ｎ，ＤＣ２−４２４８Ｓ（東レ・ダウコーニング社製）が挙げられる。また、前述した各種のポリアルキルシロキサンは単独、あるいは２種類以上混合して使用してもよい。
これらの内で、ポリメチルシロキサンが、入手が容易であることから最も好ましい。
Specific examples of the polyalkylsiloxane include dimethylpolysiloxane having a polymerization degree of 1 to 20, diphenylpolysiloxane, polymethylphenylsiloxane, polymethylepoxypropylsiloxane, polymethylaminopropylsiloxane, and the like. Examples of products include TSF451, THF450, FQF501, YSA6403, TSA720, YSA02, TSA750, TSA750S, YSA6406, TSA780, TSA7341, TSA739, TSA732, TSA732A, TSA772, TSA730, TSA770, ASA775, AMA7509, TS7775, AMA7509 GE Toshiba Silicone)), KM-73, KM-73A, KM-73E, KM-70, KM-71, KM-75, KM-85, KM-72, KM-72F, KM-72S, KM-72FS , KM-89, KM-90, KM-98, KM-68-1F, KS-508, KS-530, KS-531, KS-537, KS-538, KS-66, KS-69, KF 96, KS-604, KS-6702, FA-630, KS-602A, KS-603, FA-600, KM-88P, KM-91P, KM-601S (manufactured by Shin-Etsu Silicone), SH200, SH203, FS1265, SH5500, SC5540, BY28-503, SH7PA, SH5510, SH5561, SH5507, SH8730, SM5511, SM5571, SM5515, SM5512, DC200, FS1265, DC71, DC74, DB-100, F-16, DC75, 1266, 1283 DKQ1-1183, DKQ1-1068, DKQ1-071, 80, 544, EPL, 025, 1224, 1233, DKQ1-1247, 013A, 1277, CE, C-Emulsion, AFE, 92, 3, DB-110N, DC2-4248S (manufactured by Dow Corning Toray Co., Ltd.) and the like. The various polyalkylsiloxanes described above may be used alone or in combination of two or more.
Of these, polymethylsiloxane is most preferred because it is readily available.
［再生樹脂の合成］
本実施の形態の再生樹脂は、前記方法によって得たウレタン分解物と、イソシアネート基またはエポキシ基を２以上有する硬化剤と、前記ポリアルキルシロキサンとを硬化させて得られる。この再生樹脂の合成において、イソシアネート含有硬化剤を用いた場合には、ウレタン樹脂が合成され、エポキシ基を含有する硬化剤を用いた場合には、エポキシ樹脂が合成される。いずれの場合においても、反応系にポリアルキルシロキサンを添加することによって、再生樹脂の物性が改善される。
以下、ポリウレタン樹脂を再生樹脂として合成する第１の実施の形態と、エポキシ樹脂を再生樹脂として合成する第２の実施の形態に区分して説明する。
[Synthesis of recycled resin]
The recycled resin of the present embodiment is obtained by curing the urethane decomposition product obtained by the above method, a curing agent having two or more isocyanate groups or epoxy groups, and the polyalkylsiloxane. In the synthesis of this recycled resin, a urethane resin is synthesized when an isocyanate-containing curing agent is used, and an epoxy resin is synthesized when a curing agent containing an epoxy group is used. In either case, the physical properties of the recycled resin can be improved by adding polyalkylsiloxane to the reaction system.
The following description is divided into a first embodiment in which a polyurethane resin is synthesized as a recycled resin and a second embodiment in which an epoxy resin is synthesized as a recycled resin.
［第１の実施の形態］
本実施の形態において、ウレタン再生樹脂は、前述のウレタン分解物と２以上のイソシアネート基を有する硬化剤と、ポリアルキルシロキサンの少なくとも３成分を反応させて得られる。
この再生樹脂の合成において、ウレタン分解物と硬化剤との配合比率は、ＮＣＯ／ＯＨ比が０．８以上となるように配合することが好ましい。比率が、０．８以下であると、未反応の官能基（ＮＣＯ基、あるいはＯＨ基）が残留し、再生樹脂の機械的強度が低下して実用的な樹脂を得ることができない。
[First Embodiment]
In the present embodiment, the urethane recycled resin is obtained by reacting the aforementioned urethane decomposition product, a curing agent having two or more isocyanate groups, and at least three components of polyalkylsiloxane.
In the synthesis of this recycled resin, the blending ratio of the urethane decomposition product and the curing agent is preferably blended so that the NCO / OH ratio is 0.8 or more. When the ratio is 0.8 or less, an unreacted functional group (NCO group or OH group) remains, and the mechanical strength of the recycled resin is lowered, so that a practical resin cannot be obtained.
再生時にウレタン分解物と混合されるイソシアネート化合物硬化剤としては、一般的にウレタン樹脂を生成する際に使用されているイソシアネートであれば使用することができ、具体的には、トルエンジイソシアネート（ＴＤＩ）、ジフェニルメタンジイソシアネート（ＭＤＩ）、１，６−ヘキサメチレンジイソシアネート（ＨＤＩ）、２，２，４（２，４，４）−トリメチルヘキサメチレンジイソシアネート（ＴＭＤＩ）、ｐ−フェニレンジイソシアネート（ＰＰＤＩ）、４，４’−ジシクロヘキシルメタンジイソシアネート（ＨＭＤＩ）、３，３’−ジメチルジフェニル４，４’−ジイソシアネート（ＴＯＤＩ）、ジアニシジンジイソシアネート（ＤＡＤＩ）、ｍ−キシレンジイソシアネート（ＸＤＩ）、テトラメチルキシレンジイソシアネート（ＴＭＸＤＩ）、イソフォロンジイソシアネート（ＩＰＤＩ）、１，５−ナフタレンジイソシアネート（ＮＤＩ）、ｔｒａｎｓ−１，４−シクロヘキシルジイソシアネート（ＣＨＤＩ）、ジメチルトリフェニルメタンテトライソシアネート、トリフェニルメタントリイソシアネート、トリス（イソシアネートフェニル）チオホスフェート、変成ＴＤＩ、変成ＭＤＩなどが挙げられる。これらの物質は単独または２つ以上の物質を混合して用いても良い。 As the isocyanate compound curing agent mixed with the urethane decomposition product at the time of regeneration, any isocyanate that is generally used when producing a urethane resin can be used. Specifically, toluene diisocyanate (TDI) , Diphenylmethane diisocyanate (MDI), 1,6-hexamethylene diisocyanate (HDI), 2,2,4 (2,4,4) -trimethylhexamethylene diisocyanate (TMDI), p-phenylene diisocyanate (PPDI), 4,4 '-Dicyclohexylmethane diisocyanate (HMDI), 3,3'-dimethyldiphenyl 4,4'-diisocyanate (TODI), dianisidine diisocyanate (DADI), m-xylene diisocyanate (XDI), tetramethylxylene diisocyanate Nate (TMXDI), isophorone diisocyanate (IPDI), 1,5-naphthalene diisocyanate (NDI), trans-1,4-cyclohexyl diisocyanate (CHDI), dimethyltriphenylmethane tetraisocyanate, triphenylmethane triisocyanate, tris (isocyanate) Phenyl) thiophosphate, modified TDI, modified MDI and the like. These substances may be used alone or in admixture of two or more substances.
また、これらのイソシアネートを用いて合成されたイソシアネート末端プレポリマーを用いてもよい。イソシアネート硬化剤として、プレポリマーを用いることによって、伸び、及び、ゴム弾性の点で優れた再生樹脂を製造することができる。イソシアネート末端プレポリマーを製造するには、ポリオールに、過剰量のジイソシアネート化合物を反応させることによって製造することができる。 Moreover, you may use the isocyanate terminal prepolymer synthesize | combined using these isocyanate. By using a prepolymer as the isocyanate curing agent, a recycled resin excellent in elongation and rubber elasticity can be produced. An isocyanate-terminated prepolymer can be produced by reacting an excess amount of a diisocyanate compound with a polyol.
また、ウレタン分解物の粘度を調整するために、樹脂組成物にポリオールを混合してもよい。
具体例としては、このポリオールは、一般的にウレタン樹脂を生成する際に使用されるいずれのポリオールでもよく、例えば低分子量ポリオールや高分子量ポリオールなどが挙げられる。
Moreover, in order to adjust the viscosity of a urethane decomposition product, you may mix a polyol with a resin composition.
As a specific example, this polyol may be any polyol generally used when producing a urethane resin, and examples thereof include a low molecular weight polyol and a high molecular weight polyol.
低分子量ポリオールとしては、例えば、エチレングリコール、ジエチレングリコール、プロピレングリコール、ジプロピレングリコール、１，４−ブタンジオール、プロパンジオール、１，６−ヘキサンジオール、ネオペンチルグリコール、トリエチレングリコール、ビスフェノールＡ、水素化ビスフェノールＡ、キシレングリコールなどの低分子ジオール、例えば、グリセリン、トリメチロールプロパンなどの低分子量トリオール、例えば、Ｄ−ソルビトール、キシリトール、Ｄ−マンニトール、Ｄ−マンニットなどの水酸基を４個以上有する低分子量ポリオールなどが挙げられる。 Examples of the low molecular weight polyol include ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, 1,4-butanediol, propanediol, 1,6-hexanediol, neopentyl glycol, triethylene glycol, bisphenol A, hydrogenation Low molecular weight diols such as bisphenol A and xylene glycol, for example, low molecular weight triols such as glycerin and trimethylolpropane, and low molecular weights having 4 or more hydroxyl groups such as D-sorbitol, xylitol, D-mannitol, D-mannitol A polyol etc. are mentioned.
高分子量ポリオールとしては、例えば、ポリエーテルポリオール、ポリエステルポリオール、ポリカーボネートポリオール、アクリルポリオール、エポキシポリオール、天然油ポリオール、シリコンポリオール、フッ素ポリオール、ポリオレフィンポリオール、ポリエーテルエステルポリオール等が挙げられる。これらのポリオールを単独または２つ以上の物質を混合して用いてもよい。 Examples of the high molecular weight polyol include polyether polyol, polyester polyol, polycarbonate polyol, acrylic polyol, epoxy polyol, natural oil polyol, silicon polyol, fluorine polyol, polyolefin polyol, polyether ester polyol, and the like. These polyols may be used alone or in admixture of two or more substances.
これらのポリオールは、添加するウレタン分解物の粘度およびポリオールの分子量によって異なるが、おおむねウレタン分解物１００重量部に対して、０〜１５０重量部の範囲で用いることができる。ポリオールの量がこの範囲を超えた場合には、ウレタン分解物の利用を目的とする本発明の趣旨を損なうばかりでなく、ポリアルキルシロキサンを添加する効果も期待できない。 These polyols vary depending on the viscosity of the urethane decomposition product to be added and the molecular weight of the polyol, but can be used in the range of 0 to 150 parts by weight with respect to 100 parts by weight of the urethane decomposition product. When the amount of the polyol exceeds this range, not only does the purpose of the present invention aiming at utilization of the urethane decomposition product be impaired, but also the effect of adding polyalkylsiloxane cannot be expected.
本実施の形態の樹脂組成物には、前記ポリアルキルシロキサンを１．０〜５０００ｐｐｍの範囲で添加することが好ましい。ポリアルキルシロキサンの量がこの範囲を下回った場合、得られる再生樹脂の引っ張り強度および切断時伸びの特性の改善が十分に得られなくなるおそれがある。また、樹脂硬化物表面のべたつきが解消されず、実用性が低くなる。一方、ポリアルキルシロキサンの量を上記範囲を超えて添加しても、その量の増加に見合う効果の改善が見られず、不経済である。 It is preferable to add the polyalkylsiloxane in the range of 1.0 to 5000 ppm to the resin composition of the present embodiment. When the amount of the polyalkylsiloxane is below this range, there is a possibility that the improvement of the tensile strength and elongation characteristics at the time of cutting cannot be sufficiently obtained. Moreover, the stickiness of the resin cured product surface is not eliminated, and the practicality is lowered. On the other hand, even if the amount of polyalkylsiloxane exceeds the above range, the effect corresponding to the increase in the amount is not improved, which is uneconomical.
本実施の形態のウレタン再生樹脂を製造するには、前記ウレタン樹脂分解物とイソシアネート硬化剤とポリアルキルシロキサンとを万能攪拌機等を用いて混合し、混合物を室温〜５０℃の温度で成形型に流し込み、室温〜２５０℃にて数分〜一晩程度硬化させることによって成形体が得られる。混合の際に、有機物粒子または無機物粒子などを充填材として加えたり、可塑剤、カップリング剤等を配合してもよい。 In order to produce the urethane recycled resin of the present embodiment, the urethane resin decomposition product, the isocyanate curing agent and the polyalkylsiloxane are mixed using a universal stirrer or the like, and the mixture is formed into a mold at a temperature of room temperature to 50 ° C. The molded product is obtained by pouring and curing at room temperature to 250 ° C. for several minutes to overnight. In mixing, organic particles or inorganic particles may be added as a filler, or a plasticizer, a coupling agent, or the like may be blended.
本実施の形態の再生樹脂は、発泡成形物として再生することもできる。樹脂組成物を発泡させるには、イソシアネート硬化剤を、ウレタン分解物およびポリオールの水酸基に対して過剰量添加することによって水酸基と２当量のイソシアネート基が反応し、尿素結合を形成するとともに炭酸ガスを発生して発泡する。この場合、発泡倍率は２倍以下とすることが好ましい。発泡倍率を２倍以上とすると、再生樹脂の機械的強度が低下して実用的ではない。 The recycled resin of the present embodiment can also be recycled as a foam molded product. To foam the resin composition, an excess amount of an isocyanate curing agent is added to the urethane decomposition product and the hydroxyl group of the polyol, whereby the hydroxyl group reacts with 2 equivalents of the isocyanate group to form a urea bond and carbon dioxide gas. Generates and foams. In this case, the expansion ratio is preferably 2 times or less. If the expansion ratio is 2 times or more, the mechanical strength of the recycled resin is lowered, which is not practical.
本実施の形態における特徴は、再生ウレタン樹脂がエラストマー特性を有する組成で製造される時に顕著に発揮される。 The feature in the present embodiment is remarkably exhibited when the recycled urethane resin is produced with a composition having elastomer characteristics.
［第２の実施の形態］
本実施の形態において、エポキシ再生樹脂は、前述のウレタン分解物と２以上のエポキシ基を有する硬化剤と、ポリアルキルシロキサンの少なくとも３成分を反応させて得られる。
再生時にウレタン分解物に添加されるエポキシ化合物硬化剤としては、１分子中に２個以上のエポキシ基を有するものであればよく、特に限定されるものではない。その具体的例としては、ビスフェノールＡ型エポキシ樹脂、ビスフェノールＦ型エポキシ樹脂、ビフェニル型エポキシ樹脂、フェノールノボラック型エポキシ樹脂、オルソクレゾールノボラック型エポキシ樹脂、ジシクロペンタジエンノボラック型エポキシ樹脂、トリス−ヒドロキシフェニルメタン型エポキシ樹脂、その他の多官能型エポキシ樹脂のほか、脂環式エポキシ樹脂、トリグリシジールイソシアネートやヒダントインエポキシの如き含複素環エポキシ樹脂、水添ビスフェノールＡ型エポキシ樹脂、プロピレングリコールジグリシジルエーテルやペンタエリスリトール−ポリ−グリシジルエーテルなどの脂肪族系エポキシ樹脂、脂肪族もしくは芳香族カルボン酸とエピクロルヒドリンとの反応によって得られるエポキシ樹脂、スピロ環含有エポキシ樹脂、オルソ−アリル−フェノールノボラック化合物とエピクロルヒドリンとの反応生成物であるグリシジルエーテル型エポキシ樹脂、ビスフェノールＡのそれぞれの水酸基のオルソ位にアリル基を有するジアリルビスフェノール化合物とエピクロルヒドリンとの反応生成物であるグリシジルエーテル型エポキシ樹脂などである。さらに柔軟性を付与させる目的で、低極性結合基を導入させたオリゴマー型変性ビスフェノールＡ型エポキシ樹脂などがあり、さらに、難燃性を付与させる目的の臭素化したエポキシ樹脂なとも用いることができる。この中でも、室温における粘度が５００ポアズ以下、さらには３００ポアズ以下の室温で液状のエポキシ樹脂を用いると、取り扱いが容易で好ましい。液状エポキシ樹脂の具体例としては、たとえば、エピコート８２５，エピコート８２７，エピコート８２８，エピコート８２８ＥＬ，エピコート８２８ＸＡ，エピコート８３４，エピート８０１，エピコート８０１Ｐ，エピコート８０２，エピコート８０２ＸＡ，エピコート８１５，エピコート８１５ＸＡ，エピコート８１６Ａ，エピコート８１９，エピコート８０６，エピコート８０６Ｌ，エピコート８０７（以上ジャパンエポキシレジン株式会社）、ＥＰ−４１００，ＥＰ−４１００Ｇ，ＥＰ−４１００Ｅ，ＥＰ−４１００Ｗ，ＥＰ−４１００ＴＸ，ＥＰ−４３００Ｅ，ＥＰ−４３４０，ＥＰ−４２００，ＥＰ−４４００，ＥＰ−４５００Ａ，ＥＰ−４５１０，ＥＰ−４５２０，ＥＰ−４５２０Ｓ，ＥＰ−４５２０ＴＸ，ＥＰ−４５３０，ＥＰ−４９０１，ＥＰ−４９０１Ｅ，ＥＰ−４９５０，ＥＰ−４０００，ＥＰ−４００５，ＥＰ−１３０７，ＥＰ−４００４，Ｅｐ−４０８０Ｅ，ＥＰ−４０１２Ｍ，ＥＰ−４０００Ｓ，ＥＰ−４０００ＳＳ，ＥＰ−４００３Ｓ，ＥＰ−４０１０Ｓ，ＥＰ−４０８８Ｓ，ＥＰ−４０８５Ｓ（以上旭電化工業）、ＥＸＡ−４８５０−１５０，ＥＸＡ−４８５０−１０００，（以上大日本インキ化学工業、ＣＥＬ−２０２１Ｐ（３，４−エポキシシクロヘキシルメチル３’，４’−エポキシシクロヘキサンカルボキシレート、エポキシ当量１２８〜１４０、粘度２００〜３５０ｃＰ／２５℃）、ＣＥＬ−２０２１Ａ（３，４−エポキシシクロヘキシルメチル３’４’−エポキシシクロヘキサンカルボキシレート、エポキシ当量１３０〜１４５、粘度２００〜４５０ｃＰ／２５℃）、ＣＥＬ−２０００（１−ビニル−３，４−エポキシシクロヘキサン、１．５ｃＰ／２５℃）、ＣＥＬ−３０００（１，２，８，９−ジエポキシリモネン、エポキシ当量９３．５以下、粘度５〜２０ｃＰ／２５℃）（以上ダイセル化学工業製）や、デナコールＥＸ−４２１、２０１（レゾルシンジグリシジルエーテル）、２１１（ネオペンチルグリコールジグリシジルエーテル）、９１１（プロピレングリコールジグリシジルエーテル）、７０１（アジピン酸ジグリシジルエステル）（以上ナガセ化成工業製）等を用いることができる。これらのエポキシ樹脂は単独で用いても２種以上を混合して用いてもよい。
[Second Embodiment]
In the present embodiment, the epoxy regenerated resin is obtained by reacting the aforementioned urethane decomposition product, a curing agent having two or more epoxy groups, and at least three components of polyalkylsiloxane.
The epoxy compound curing agent added to the urethane decomposition product at the time of regeneration is not particularly limited as long as it has two or more epoxy groups in one molecule. Specific examples thereof include bisphenol A type epoxy resin, bisphenol F type epoxy resin, biphenyl type epoxy resin, phenol novolac type epoxy resin, orthocresol novolac type epoxy resin, dicyclopentadiene novolac type epoxy resin, tris-hydroxyphenylmethane. Type epoxy resins, other polyfunctional epoxy resins, alicyclic epoxy resins, heterocyclic epoxy resins such as triglycidyl isocyanate and hydantoin epoxy, hydrogenated bisphenol A type epoxy resins, propylene glycol diglycidyl ether and penta Aliphatic epoxy resins such as erythritol-poly-glycidyl ether, epoxy resins obtained by reaction of aliphatic or aromatic carboxylic acids with epichlorohydrin, spiro -Containing epoxy resin, reaction product of ortho-allyl-phenol novolak compound and epichlorohydrin, glycidyl ether type epoxy resin, reaction product of diallyl bisphenol compound having an allyl group at each hydroxyl position of bisphenol A and epichlorohydrin And glycidyl ether type epoxy resin. In addition, for the purpose of imparting flexibility, there are oligomer-type modified bisphenol A type epoxy resins into which a low-polarity linking group is introduced, and it can also be used as a brominated epoxy resin for the purpose of imparting flame retardancy. . Among them, it is preferable to use an epoxy resin that is liquid at room temperature with a viscosity at room temperature of 500 poise or less, and further 300 poise or less, because it is easy to handle. Specific examples of the liquid epoxy resin include, for example, Epicoat 825, Epicoat 827, Epicoat 828, Epicoat 828EL, Epicoat 828XA, Epicoat 834, Epitoe 801, Epicoat 801P, Epicoat 802, Epicoat 802XA, Epicoat 815, Epicoat 815XA, Epicoat 816A, Epicoat 819, Epicoat 806, Epicoat 806L, Epicoat 807 (above Japan Epoxy Resin Co., Ltd.), EP-4100, EP-4100G, EP-4100E, EP-4100W, EP-4100TX, EP-4300E, EP-4340, EP- 4200, EP-4400, EP-4500A, EP-4510, EP-4520, EP-4520S, EP-4520TX, EP-4530 EP-4901, EP-4901E, EP-4950, EP-4000, EP-4005, EP-1307, EP-4004, Ep-4080E, EP-4012M, EP-4000S, EP-4000SS, EP-4003S, EP- 4010S, EP-4088S, EP-4085S (Asahi Denka Kogyo), EXA-4850-150, EXA-4850-1000, (Dainippon Ink and Chemicals, CEL-2021P (3,4-epoxycyclohexylmethyl 3 ′, 4′-epoxycyclohexanecarboxylate, epoxy equivalent 128-140, viscosity 200-350 cP / 25 ° C., CEL-2021A (3,4-epoxycyclohexylmethyl 3′4′-epoxycyclohexanecarboxylate, epoxy equivalent 130-145, Viscosity 2 0-450 cP / 25 ° C.), CEL-2000 (1-vinyl-3,4-epoxycyclohexane, 1.5 cP / 25 ° C.), CEL-3000 (1,2,8,9-diepoxy limonene, epoxy equivalent 93) .5 or less, viscosity 5 to 20 cP / 25 ° C. (made by Daicel Chemical Industries), Denacol EX-421, 201 (resorcin diglycidyl ether), 211 (neopentyl glycol diglycidyl ether), 911 (propylene glycol diglycidyl) Ether), 701 (adipic acid diglycidyl ester) (manufactured by Nagase Kasei Kogyo Co., Ltd.), etc. These epoxy resins may be used alone or in combination of two or more.
エポキシ再生樹脂を製造する方法としては、ウレタン樹脂分解物と前記エポキシ樹脂とを万能攪拌機等を用いて混合し、混合物を室温〜２００℃の温度で成形型に流し込み、数分〜１晩程度加熱硬化させることによって成形体が得られる。混合の際に、有機物粒子又は無機物粒子などを充填材として加えたり、可塑剤、カップリング剤等を配合してもよい。硬化温度は使用するウレタン樹脂分解物、エポキシ樹脂の融点又は軟化点等によって異なるが、概して８０〜２００℃程度がよい。
As a method for producing an epoxy regenerated resin, a urethane resin decomposition product and the epoxy resin are mixed using a universal stirrer or the like, and the mixture is poured into a mold at a temperature of room temperature to 200 ° C. and heated for several minutes to overnight. A molded body is obtained by curing. In mixing, organic particles or inorganic particles may be added as a filler, or a plasticizer, a coupling agent, or the like may be blended. The curing temperature varies depending on the urethane resin decomposition product used, the melting point or softening point of the epoxy resin, and is generally preferably about 80 to 200 ° C.
以下、実施例および比較例により本発明を詳細に説明する。 Hereinafter, the present invention will be described in detail by way of examples and comparative examples.
［実施例１〜４、比較例１］
以下により、ウレタン分解物を用いて、ウレタン樹脂を製造する方法についての実施例を説明する。
まず、下記方法によってウレタン分解物Ａおよびウレタン分解物Ｂを製造した。
[Examples 1 to 4, Comparative Example 1]
Below, the Example about the method to manufacture a urethane resin using a urethane decomposition product is described.
First, urethane decomposition product A and urethane decomposition product B were produced by the following method.
（ウレタン分解物Ａの製造）
水酸基価２５のポリマーポリオールと等量のトルエンジイソシアネート（２，４−体／２，６−体＝８０／２０）から得られる軟質ウレタン樹脂の廃材を２ｍｍ程度に粉砕したものを被分解物として準備した。
(Manufacture of urethane decomposition product A)
Prepared as a material to be decomposed is a waste material of soft urethane resin obtained from an equivalent amount of toluene diisocyanate (2,4-isomer / 2,6-isomer = 80/20) with a polymer polyol having a hydroxyl value of 25 to about 2 mm. did.
上記ウレタン樹脂の廃材とジエタノールアミンを重量比で８／１になるように混合した。この混合物を押出機を用いて分解した。押出機のシリンダ部を２５０℃に加熱し、滞留時間が５分になるようにスクリューの回転を制御し、連続投入し分解した。排出口からは２層に分離した分解物が排出された。そのうち上層のみを分解物Ａとして用いた。この分解物のＯＨ価は１５７．９ｍｇＫＯＨ／ｇであった。 The waste material of urethane resin and diethanolamine were mixed so that the weight ratio was 8/1. This mixture was decomposed using an extruder. The cylinder part of the extruder was heated to 250 ° C., and the rotation of the screw was controlled so that the residence time was 5 minutes. The decomposition product separated into two layers was discharged from the discharge port. Of these, only the upper layer was used as decomposition product A. The decomposition product had an OH value of 157.9 mgKOH / g.
（ウレタン分解物Ｂの製造）
等量の水酸基価５６のポリエーテルトリオールとトルエンジイソシアネート（２，４−体／２，６−体＝８０／２０）から得られる軟質ウレタン樹脂の廃材を２ｍｍ程度に粉砕したものを被分解物として準備した。
(Manufacture of urethane decomposition product B)
A waste product of a soft urethane resin obtained from an equal amount of a polyether triol having a hydroxyl value of 56 and toluene diisocyanate (2,4-isomer / 2,6-isomer = 80/20) was crushed to about 2 mm as a material to be decomposed. Got ready.
上記ウレタン樹脂の廃材とジエタノールアミンを重量比で１０／１になるように混合した。この混合物を押出機を用いて分解した。押出機のシリンダ部を２７０℃に加熱し、滞留時間が５分になるようにスクリューの回転を制御し、連続投入し分解した。排出口からは２層に分離した分解物が排出された。そのうち上層のみを分解物Ｂとして用いた。この分解物のＯＨ価は１３１．７ｍｇＫＯＨ／ｇであった。 The waste material of the urethane resin and diethanolamine were mixed so that the weight ratio was 10/1. This mixture was decomposed using an extruder. The cylinder part of the extruder was heated to 270 ° C., and the rotation of the screw was controlled so that the residence time was 5 minutes. The decomposition product separated into two layers was discharged from the discharge port. Only the upper layer was used as the decomposition product B. The decomposition product had an OH value of 131.7 mgKOH / g.
（再生ウレタン樹脂の製造）
前記工程で製造したウレタン分解物を用いて、以下の方法でウレタン樹脂（再生ウレタン）を合成した。
平均分子量３０００のポリオキシプロピレントリオール（三井武田ケミカル社製、製品番号ＭＮ−３０５０）と過剰のトルエンジイソシアネート（２，４−体／２，６−体＝８０／２０；三井武田ケミカル社製、製品番号Ｔ−８０）とを混合し、８０℃で３時間反応させて、末端イソシアネート基含有率２．９％のプレポリマーを得た。
(Manufacture of recycled urethane resin)
A urethane resin (regenerated urethane) was synthesized by the following method using the urethane decomposition product produced in the above step.
Polyoxypropylene triol having an average molecular weight of 3000 (manufactured by Mitsui Takeda Chemical Co., product number MN-3050) and excess toluene diisocyanate (2,4-isomer / 2,6-isomer = 80/20; manufactured by Mitsui Takeda Chemical Co., Ltd., product No. T-80) was mixed and reacted at 80 ° C. for 3 hours to obtain a prepolymer having a terminal isocyanate group content of 2.9%.
前記ウレタン分解物Ａ１０ｇと平均分子量３０００のポリオキシプロピレントリオール（三井武田ケミカル社製、製品番号ＭＮ−３０５０）が重量比で１：１になるように混合し、更に下記表１に示す配合量となるようにポリアルキルシロキサンのトルエン９５％溶液（ＧＥ東芝シリコーン社製、製品番号ＴＳＡ７２０）０．０４〜７．５５ｇを添加した。その混合物と前記ウレタンプレポリマー５５．５ｇとを、ＮＣＯ／ＯＨ比が１．０になるように攪拌混合し、型に流し室温で成型したところ一日後に硬化した。これを脱型し、ウレタン樹脂を製造した。
この再生ウレタン樹脂について、引張り強度、および切断時伸びを測定し、また指触試験を行った。引っ張り強度、および切断時伸びは、ＪＩＳ−Ｋ−７３１２に規定されている方法によって行った。また、指触試験は、硬化物表面を乾燥した指で軽く触れ、指を離す際に抵抗を感じるときを、「×」、全く抵抗を感じないときを、「○」で表す。
その結果を表１に示す。
The urethane decomposition product A 10 g and polyoxypropylene triol having an average molecular weight of 3000 (product number MN-3050, manufactured by Mitsui Takeda Chemical Co., Ltd.) are mixed so as to have a weight ratio of 1: 1. To this, 0.04 to 7.55 g of a 95% toluene solution of polyalkylsiloxane (manufactured by GE Toshiba Silicone, product number TSA720) was added. The mixture and 55.5 g of the urethane prepolymer were stirred and mixed so that the NCO / OH ratio was 1.0, poured into a mold and molded at room temperature, and cured one day later. This was demolded to produce a urethane resin.
With respect to this recycled urethane resin, the tensile strength and elongation at break were measured, and a finger touch test was performed. The tensile strength and elongation at break were performed by the methods specified in JIS-K-7312. Further, in the finger touch test, when the surface of the cured product is lightly touched with a dry finger and a resistance is felt when the finger is released, “X” is indicated, and when no resistance is felt, “◯” is indicated.
The results are shown in Table 1.
［実施例５〜８、比較例２］
前記実施例１〜４におけるウレタン分解物Ａに変えてウレタン分解物Ｂを用いたこと以外は、前記実施例１〜４と同様にして、ウレタン樹脂を製造した。
得られたウレタン樹脂の引張り強度、および切断時伸びを測定し、また指触試験を行った。その結果を、表２に示す。
[Examples 5 to 8, Comparative Example 2]
A urethane resin was produced in the same manner as in Examples 1 to 4 except that urethane decomposition product B was used instead of urethane decomposition product A in Examples 1 to 4.
The obtained urethane resin was measured for tensile strength and elongation at break, and a finger touch test was performed. The results are shown in Table 2.
［比較例３〜７］
ポリオキシプロピレントリオール（ＭＮ−３０５０）１０ｇに対して、ポリアルキルシロキサン（ＴＳＡ７２０）０．０１〜２．４５ｇとジブチル酸ジラウリル錫０．０１ｇとを添加し混合した。その混合物とＮＣＯ／ＯＨ＝１．０になるように前記ウレタンプレポリマー１４．５ｇとを攪拌混合し、型に流し室温で成型したところ、一日後に硬化した。これを脱型し、ウレタン樹脂を製造した。
得られたウレタン樹脂の引張り強度、および切断時伸びを測定し、また指触試験を行った。その結果を、表３に示す。
[Comparative Examples 3 to 7]
To 10 g of polyoxypropylene triol (MN-3050), 0.01 to 2.45 g of polyalkylsiloxane (TSA720) and 0.01 g of dilauryltin dibutylate were added and mixed. The mixture was stirred and mixed with 14.5 g of the urethane prepolymer so that NCO / OH = 1.0, poured into a mold and molded at room temperature, and cured one day later. This was demolded to produce a urethane resin.
The obtained urethane resin was measured for tensile strength and elongation at break, and a finger touch test was performed. The results are shown in Table 3.
上記表１、表２および表３の結果から明らかなように、ポリアルキルシロキサンを添加せず、ウレタン分解物を用いて製造した再生ウレタン樹脂は、引っ張り強度が低く、切断時伸びも低かった。また、硬化物の表面はべたついて、粘着性を有していた。これに対して、ポリアルキルシロキサンを添加した樹脂は、引っ張り強さが３倍程度改善されており、また、切断時伸びも２倍以上改善されていた。
さらに、ウレタン分解物を用いない比較例３〜７の樹脂は、切断時伸びは高かったものの、引っ張り強度は本発明実施例のものには及ばなかった。
As is clear from the results of Table 1, Table 2 and Table 3, the recycled urethane resin produced by using the urethane decomposition product without adding polyalkylsiloxane had low tensile strength and low elongation at break. Further, the surface of the cured product was sticky and had tackiness. On the other hand, the resin to which polyalkylsiloxane was added had improved tensile strength by about 3 times, and elongation at break was improved by 2 times or more.
Furthermore, although the resins of Comparative Examples 3 to 7 that did not use the urethane decomposition product had high elongation at the time of cutting, the tensile strength did not reach that of the examples of the present invention.
[実施例９〜２１、比較例８]
（再生エポキシ樹脂の製造）
前述の実施例１〜４において説明したウレタン分解物を用いて、以下の方法で再生エポキシ樹脂を合成した。
前記ウレタン分解物Ａ５５ｇに下記表５に示す配合量となるようにポリアルキルシロキサンのトルエン９５％溶液（ＧＥ東芝シリコーン社製、製品番号ＴＳＡ７２０）０．０４〜７．５５ｇを添加した。その混合物とエポキシ樹脂：デナコールＥＸ−２１２（ナガセケムテックス製、エポキシ当量１１５）１８．７ｇとを、エポキシ基／ＯＨ比が１．０になるように攪拌混合し、型に流し室温で成型したところ一日後に硬化した。これを脱型し、エポキシ樹脂を製造した。
この再生エポキシ樹脂について、実施例１〜４と同様にして引っ張り強度および切断時伸びを測定し、また指触試験を行った。その結果を表４に示す。
[Examples 9 to 21, Comparative Example 8]
(Manufacture of recycled epoxy resin)
A recycled epoxy resin was synthesized by the following method using the urethane decomposition product described in Examples 1 to 4 above.
0.04 to 7.55 g of a toluene 95% polyalkylsiloxane solution (manufactured by GE Toshiba Silicone, product number TSA720) was added to 55 g of the urethane decomposed product A so as to have a blending amount shown in Table 5 below. 18.7 g of the mixture and epoxy resin: Denacol EX-212 (manufactured by Nagase ChemteX, epoxy equivalent 115) were stirred and mixed so that the epoxy group / OH ratio was 1.0, poured into a mold, and molded at room temperature. However, it hardened after a day. This was demolded to produce an epoxy resin.
With respect to this recycled epoxy resin, the tensile strength and elongation at break were measured in the same manner as in Examples 1 to 4, and a finger touch test was performed. The results are shown in Table 4.
上記表４の結果から明らかなように、エポキシ硬化剤を用いた再生エポキシ樹脂の合成においても、ポリアルキルシロキサンを所定の量で添加することによって引っ張り強度、切断時伸びが改善され、かつ指触試験の結果も良好であった。
As is clear from the results in Table 4 above, also in the synthesis of regenerated epoxy resin using an epoxy curing agent, the tensile strength and elongation at break were improved by adding a predetermined amount of polyalkylsiloxane, and finger touch The test results were also good.
Claims (7)
上記化学式１において、Ｒは、下記化学式２に示す官能基を表す。
In the above chemical formula 1, R represents a functional group represented by the following chemical formula 2.
The recycled resin according to claim 6, wherein the recycled resin is an elastomer having rubber elasticity with an expansion ratio of 2 times or less.
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| JP2004292661A (en) * | 2003-03-27 | 2004-10-21 | Toshiba Corp | Method of decomposition treatment of rigid urethane resin and method for producing regenerated resin |
| JP2005015526A (en) * | 2003-06-23 | 2005-01-20 | Toshiba Corp | Method for treating flexible urethane resin-containing waste |
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| JPH087254A (en) * | 1994-06-16 | 1996-01-12 | Sony Corp | Magnetic recording medium |
| JP2004292661A (en) * | 2003-03-27 | 2004-10-21 | Toshiba Corp | Method of decomposition treatment of rigid urethane resin and method for producing regenerated resin |
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