JPH0216159A - Preparation of cyanato resin modified with polyetherimide - Google Patents
Preparation of cyanato resin modified with polyetherimideInfo
- Publication number
- JPH0216159A JPH0216159A JP16586788A JP16586788A JPH0216159A JP H0216159 A JPH0216159 A JP H0216159A JP 16586788 A JP16586788 A JP 16586788A JP 16586788 A JP16586788 A JP 16586788A JP H0216159 A JPH0216159 A JP H0216159A
- Authority
- JP
- Japan
- Prior art keywords
- resin
- polyetherimide
- cyanato
- kneaded
- thermoplastic polyester
- 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 35
- 239000011347 resin Substances 0.000 title claims abstract description 35
- 125000001651 cyanato group Chemical group [*]OC#N 0.000 title claims abstract description 26
- 239000004697 Polyetherimide Substances 0.000 title claims abstract description 11
- 229920001601 polyetherimide Polymers 0.000 title claims abstract description 11
- 229920000728 polyester Polymers 0.000 claims abstract description 17
- 238000002844 melting Methods 0.000 claims abstract description 7
- 230000008018 melting Effects 0.000 claims abstract description 7
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 7
- 229920006346 thermoplastic polyester elastomer Polymers 0.000 claims abstract description 7
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 7
- 238000004898 kneading Methods 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 4
- 150000001913 cyanates Polymers 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 18
- 239000002904 solvent Substances 0.000 abstract description 10
- AHZMUXQJTGRNHT-UHFFFAOYSA-N [4-[2-(4-cyanatophenyl)propan-2-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C)(C)C1=CC=C(OC#N)C=C1 AHZMUXQJTGRNHT-UHFFFAOYSA-N 0.000 abstract 1
- -1 4-cyanatophenyl Chemical group 0.000 description 10
- 238000000034 method Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000004643 cyanate ester Substances 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229920006015 heat resistant resin Polymers 0.000 description 3
- 229920001225 polyester resin Polymers 0.000 description 3
- 239000004645 polyester resin Substances 0.000 description 3
- 229920005992 thermoplastic resin Polymers 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical group CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920002492 poly(sulfone) Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- GGSRTHRSSCWGGK-UHFFFAOYSA-L 2,2-dibutyl-5-hydroxy-1,3,2-dioxastannepane-4,7-dione Chemical compound CCCC[Sn]1(CCCC)OC(=O)CC(O)C(=O)O1 GGSRTHRSSCWGGK-UHFFFAOYSA-L 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 239000004831 Hot glue Substances 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- 229920009204 Methacrylate-butadiene-styrene Polymers 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001665 Poly-4-vinylphenol Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229920004738 ULTEM® Polymers 0.000 description 1
- 229920004747 ULTEM® 1000 Polymers 0.000 description 1
- YKONYNBAMHVIMF-UHFFFAOYSA-N [2,6-dichloro-4-[2-(3,5-dichloro-4-cyanatophenyl)propan-2-yl]phenyl] cyanate Chemical compound C=1C(Cl)=C(OC#N)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(OC#N)C(Cl)=C1 YKONYNBAMHVIMF-UHFFFAOYSA-N 0.000 description 1
- SNYVZKMCGVGTKN-UHFFFAOYSA-N [4-(4-cyanatophenoxy)phenyl] cyanate Chemical compound C1=CC(OC#N)=CC=C1OC1=CC=C(OC#N)C=C1 SNYVZKMCGVGTKN-UHFFFAOYSA-N 0.000 description 1
- HEJGXMCFSSDPOA-UHFFFAOYSA-N [4-(4-cyanatophenyl)phenyl] cyanate Chemical group C1=CC(OC#N)=CC=C1C1=CC=C(OC#N)C=C1 HEJGXMCFSSDPOA-UHFFFAOYSA-N 0.000 description 1
- CNUHQZDDTLOZRY-UHFFFAOYSA-N [4-(4-cyanatophenyl)sulfanylphenyl] cyanate Chemical compound C1=CC(OC#N)=CC=C1SC1=CC=C(OC#N)C=C1 CNUHQZDDTLOZRY-UHFFFAOYSA-N 0.000 description 1
- AUYQDAWLRQFANO-UHFFFAOYSA-N [4-[(4-cyanatophenyl)methyl]phenyl] cyanate Chemical compound C1=CC(OC#N)=CC=C1CC1=CC=C(OC#N)C=C1 AUYQDAWLRQFANO-UHFFFAOYSA-N 0.000 description 1
- PPZSVSGWDQKBIW-UHFFFAOYSA-N [4-bis(4-cyanatophenoxy)phosphanyloxyphenyl] cyanate Chemical compound C1=CC(OC#N)=CC=C1OP(OC=1C=CC(OC#N)=CC=1)OC1=CC=C(OC#N)C=C1 PPZSVSGWDQKBIW-UHFFFAOYSA-N 0.000 description 1
- HYAOCWBXRFEHDV-UHFFFAOYSA-N [4-bis(4-cyanatophenoxy)phosphoryloxyphenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1OP(OC=1C=CC(OC#N)=CC=1)(=O)OC1=CC=C(OC#N)C=C1 HYAOCWBXRFEHDV-UHFFFAOYSA-N 0.000 description 1
- 239000011354 acetal resin Substances 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- SZKXDURZBIICCF-UHFFFAOYSA-N cobalt;pentane-2,4-dione Chemical compound [Co].CC(=O)CC(C)=O SZKXDURZBIICCF-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- QNZRVYCYEMYQMD-UHFFFAOYSA-N copper;pentane-2,4-dione Chemical compound [Cu].CC(=O)CC(C)=O QNZRVYCYEMYQMD-UHFFFAOYSA-N 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000011243 crosslinked material Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- UQLDLKMNUJERMK-UHFFFAOYSA-L di(octadecanoyloxy)lead Chemical compound [Pb+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O UQLDLKMNUJERMK-UHFFFAOYSA-L 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- LZKLAOYSENRNKR-LNTINUHCSA-N iron;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LZKLAOYSENRNKR-LNTINUHCSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 150000002825 nitriles Chemical group 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920003055 poly(ester-imide) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229920002102 polyvinyl toluene Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- YRSQDSCQMOUOKO-KVVVOXFISA-M silver;(z)-octadec-9-enoate Chemical compound [Ag+].CCCCCCCC\C=C/CCCCCCCC([O-])=O YRSQDSCQMOUOKO-KVVVOXFISA-M 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、高耐熱性の熱可塑性樹脂であるポリエーテル
イミドを均一に分散してなるポリエーテルイミド変性シ
アナト樹脂を、溶剤を使用せずに製造する方法であり、
本発明のポリエーテルイミド変性シアナト樹脂は、加熱
加圧成形し、必要に応じて後硬化して、耐熱性に優れ、
強度、伸びなどに優れた成形品を提供することができる
ものである。[Detailed Description of the Invention] [Field of Industrial Application] The present invention provides a polyetherimide-modified cyanato resin that is made by uniformly dispersing polyetherimide, which is a highly heat-resistant thermoplastic resin, without using a solvent. It is a method of manufacturing
The polyetherimide-modified cyanato resin of the present invention is molded under heat and pressure, and if necessary is post-cured, and has excellent heat resistance.
It is possible to provide molded products with excellent strength and elongation.
シアナト樹脂の伸びや強度を大きくする方法として低結
晶性乃至非結晶性ポリエステル樹脂を混練する方法は、
特開昭６０−２３３１７５号などにおいて知られている
が、強度の上昇が不充分で、かつ、耐熱性の低下が大き
い欠点があった。A method for increasing the elongation and strength of cyanato resin is to knead low-crystalline or non-crystalline polyester resin.
This method is known from Japanese Patent Application Laid-Open No. 60-233175, but it has the drawbacks of insufficient increase in strength and large decrease in heat resistance.
一方、特公昭６３−８１４２号においてはポリエステル
カーボネートとシアナト樹脂とを溶剤溶液とし、ついで
溶剤を除去す方法によりポリエステルカーボネート変性
シアナト樹脂を製造する方法が知られている。また、ポ
リエステルカーボネート以外にポリサルホン、ポリエー
テルサルホン、ポリエーテルイミドなどの耐熱性樹脂と
シアナト樹脂との組成物を同様に溶剤を使用して混合す
る方法が知られている。On the other hand, Japanese Patent Publication No. 63-8142 discloses a method of producing a polyester carbonate-modified cyanato resin by preparing a solvent solution of polyester carbonate and cyanato resin and then removing the solvent. Furthermore, a method is known in which a composition of a heat-resistant resin other than polyester carbonate, such as polysulfone, polyethersulfone, or polyetherimide, and cyanato resin is similarly mixed using a solvent.
溶剤を使用して混合する理由は、シアナト樹脂（プレポ
リマー）は、約７０℃以下で液体となり、２００℃以上
では数百センチポイズ程度の非常に低粘度の液体となり
、更に、シアナト樹脂は触媒や硬化剤を加える事なく、
加熱により重合する性質を有するので多量のシアナト樹
脂を例えば３００℃のような高温に加熱すると、重合反
応が起きて異常昇温し、次いで発煙を伴う分解が起きる
。一方、ポリスルフォンなどの耐熱性樹脂は、流動化可
能な温度が２６０℃以上であり、２６０℃以下の温度に
おいてシアナト樹脂と直接混合することは実質的に不可
能であったことによる。The reason for mixing using a solvent is that cyanato resin (prepolymer) becomes a liquid at temperatures below about 70°C, and becomes a very low viscosity liquid of several hundred centipoise at temperatures above 200°C. without adding hardening agent,
Since cyanato resin has the property of polymerizing when heated, when a large amount of cyanato resin is heated to a high temperature such as 300° C., a polymerization reaction occurs and the temperature rises abnormally, followed by decomposition accompanied by smoking. On the other hand, the temperature at which heat-resistant resins such as polysulfone can be fluidized is 260°C or higher, and it is virtually impossible to directly mix them with cyanato resins at temperatures below 260°C.
ところが、上記の溶剤溶液とする方法においては、これ
ら耐熱性樹脂を溶解するために特殊な高沸点溶剤を必要
とするために、溶剤の残存が避けられず、硬化物の特性
を低下させる欠点を有し、又、有機溶剤を使用すること
は工業的には極めて不利な困難な工程であった。However, in the above-mentioned method of making a solvent solution, a special high-boiling point solvent is required to dissolve these heat-resistant resins, so it is inevitable that the solvent will remain, which has the disadvantage of deteriorating the properties of the cured product. Furthermore, the use of organic solvents was a difficult process that was extremely disadvantageous industrially.
本発明は、上記の欠点を解決し、工業的に容易で経済的
にも著しく有利な方法について鋭意検討した結果、溶剤
を使用しない方法を見出し、完成させたものである。The present invention is the result of extensive research into methods that solve the above-mentioned drawbacks and are industrially easy and economically advantageous, and as a result, a method that does not use a solvent has been discovered and completed.
すなわち、本発明は、（ａ）、ポリエーテルイミドと（
ｂ）、結晶融点１９０〜２５０℃の熱可塑性ポリエステ
ルエラストマーを混練して混線物（Ａ１）とし、該混練
物（Ａｔ＞と（ｃ）、低結晶性乃至非結晶性の熱可塑性
ポリエステルを混練して混練物（Ａ２）とし、この混練
物（Ａ２）とシアナト樹脂（Ｂ）とを混練してなること
を特徴とするポリエーテルイミド変性シアナト樹脂の製
造法である。That is, the present invention provides (a), polyetherimide and (
b), a thermoplastic polyester elastomer with a crystal melting point of 190 to 250° C. is kneaded to obtain a mixed wire product (A1), and the kneaded product (At> and (c), a low-crystalline to amorphous thermoplastic polyester are kneaded). This is a method for producing a polyetherimide-modified cyanato resin, characterized in that the kneaded product (A2) is obtained by kneading the kneaded product (A2) and a cyanato resin (B).
以下、本発明について説明する。The present invention will be explained below.
本発明の（ａ）、ポリエーテルイミドとは、米国６０社
で開発された「ウルテム」に代表される耐熱性熱可塑性
樹脂であり、ビスフェノールＡをエーテル結合によりフ
タル酸無水物のｍ−位で結合させ、これをｍ−フ二二レ
ンジアミンと縮合させてイミド結合して連結したもので
ある。(a) of the present invention, polyetherimide, is a heat-resistant thermoplastic resin represented by "Ultem" developed by 60 companies in the United States, and bisphenol A is bonded to the m-position of phthalic anhydride through an ether bond. This is condensed with m-phenyl diamine and linked by an imide bond.
本発明の（ロ）、の結晶融点１９０〜２５０℃の熱可塑
性ポリエステルエラストマーとは、結晶性芳香族ポリエ
ステル部分であるバードセグメントと長鎖脂肪族ポリエ
ーテル或いは脂肪族ポリエーテルのソフトセグメント部
分よりなる公知の熱可塑性のポリエステルエラストマー
であり、例えば、東洋紡績■の商品名「ベルプレン」等
がある。The thermoplastic polyester elastomer (b) of the present invention having a crystalline melting point of 190 to 250°C is composed of a bird segment which is a crystalline aromatic polyester part and a long chain aliphatic polyether or a soft segment part of an aliphatic polyether. It is a known thermoplastic polyester elastomer, and for example, there is the trade name "Belprene" manufactured by Toyobo ■.
本発明の（ｃ）、の低結晶性乃至非結晶性の熱可塑性ポ
リエステルとは、カルボン酸及びアルコール成分を選択
して結晶性を出来るだけ無くしてなるポリエステル樹脂
であり、通常軟化温度４０〜１２０℃程度の範囲にある
ホットメルト接着剤用等として公知のポリエステルであ
り、例えば日本剛性化学四の商品名［ニチゴーポリエス
ター」、東洋紡績側の商品名「バイロン」等が例示され
る。The low crystallinity or non-crystalline thermoplastic polyester (c) of the present invention is a polyester resin made by selecting carboxylic acid and alcohol components to eliminate crystallinity as much as possible, and usually has a softening temperature of 40 to 120. It is a well-known polyester for use in hot-melt adhesives in the temperature range of about 100°C, and examples thereof include Nippon Goshu Kagaku 4's trade name "Nichigo Polyester" and Toyobo's trade name "Bylon".
本発明の（Ｂ）のシアナト樹脂とは下記一般式（１）で
表される多官能性シアン酸エステル或いは該シアン酸エ
ステルプレポリマー、又はこれらシアン酸エステルを必
須成分とする公知のシアナト樹脂である。The cyanato resin (B) of the present invention is a polyfunctional cyanate ester represented by the following general formula (1), the cyanate ester prepolymer, or a known cyanato resin containing these cyanate esters as an essential component. be.
一般式 ： Ｒ（ＯＣＮ） ｍ −−（１）（式
中のｍは２以上、通常５以下の整数であり、Ｒは芳香族
の有機基であって、上記シアナト基は該有機基の芳香環
に結合しているもの）
具体的に例示すれば、１．３−又は１．４−ジシアナト
ベンゼン、１．３．５− ）リシアナトベンゼン、１．
３−、１．４−、１．６−、１．８−、２．６−又は２
．７−ジシアナトナフタレン、１，３．６−）リシアナ
トナフタレン、４，４′−ジシアナトビフェニル、ビス
（４−シアナトフェニル）メタン、２．２−ビス（４−
シアナトフェニル）フロパン、２．２−ビス（３，５−
ジクロロ−４−シアナトフェニル）プロパン、２．２−
ビス（３，５−ジブロモ−４−シアナトフェニル）プロ
パン、ビス（４−シアナトフェニル）エーテル、ビス（
４−シアナトフェニル）チオエーテル、ビス（４−シア
ナトフェニル）スルホントリス（４−シアナトフェニル
）ホスファイト、トリス（４−シアナトフェニル）ホス
フェート、オよび末端ＯＨ基含有ポリカーボネートオリ
ゴマーとハロゲン化シアンとの反応によりえられるシア
ン酸エステル（ＬＩＳＰ−４０２６９１３） 、／ボラ
ックとハロゲン化シアンとの反応により得られるシアン
酸ｘｘｆル（ＬＩＳＰ−４０２２７５５、ｕｓＰ−３４
４８０７９）、及びヒドロキシベンザルアルデヒド類と
アルキル置換ピリジン類とを反応させてなるポリ−ヒド
ロキシ−スチリル−ピリジンとハロゲン化シアンとを反
応させて得られるスチリル−ピリジン−シアネート（Ｕ
ＳＰ−４５７８４３９）などである。これらのほかに特
公昭４１−１９２８ 、同４３−１８４６８、同４４−
４７９１ 、同４５−１１７１２、同４６−４１１１２
、同４７−２６８５３、特開昭５１−６３１４９、ＵＳ
Ｐ−３５５３２４４，３７５５４０２，３７４０３４８
，３５９５９００，３６９４４１０及び４１１６９４６
などに記載のシアン酸エステルも用いつる。General formula: R(OCN) m --(1) (m in the formula is an integer of 2 or more and usually 5 or less, R is an aromatic organic group, and the cyanato group is an aromatic group of the organic group. 1.3- or 1.4-dicyanatobenzene, 1.3.5-) lycyanatobenzene, 1.
3-, 1.4-, 1.6-, 1.8-, 2.6- or 2
．． 7-dicyanatonaphthalene, 1,3.6-) dicyanatonaphthalene, 4,4'-dicyanatobiphenyl, bis(4-cyanatophenyl)methane, 2,2-bis(4-
cyanatophenyl)furopane, 2,2-bis(3,5-
dichloro-4-cyanatophenyl)propane, 2.2-
Bis(3,5-dibromo-4-cyanatophenyl)propane, bis(4-cyanatophenyl)ether, bis(
4-cyanatophenyl) thioether, bis(4-cyanatophenyl) sulfonate, tris(4-cyanatophenyl) phosphite, tris(4-cyanatophenyl) phosphate, and polycarbonate oligomers containing terminal OH groups and cyanogen halides. Cyanic acid ester obtained by the reaction with (LISP-4026913) / Cyanic acid xxf obtained by the reaction of Borac with cyanogen halide (LISP-4022755, USP-34
48079), and styryl-pyridine-cyanate (U
SP-4578439). In addition to these, Tokuko Sho 41-1928, Sho 43-18468, Sho 44-
4791, 45-11712, 46-41112
, 47-26853, JP 51-63149, US
P-3553244, 3755402, 3740348
, 3595900, 3694410 and 4116946
Cyanic acid esters described in et al. can also be used.
また、上述した多官能性シアン酸エステルは、前記の多
官能シアン酸エステル化合物中のシアン基が三量化する
ことよって形成されるｓｙｍ −） ＩＪアジン環と未
反応のシアナト基とを一般に有したプレポリマーの状態
においても好適に使用出来るものである。Further, the above-mentioned polyfunctional cyanate ester generally has a sym-)IJ azine ring formed by trimerization of the cyanide group in the above-mentioned polyfunctional cyanate ester compound and an unreacted cyanato group. It can also be suitably used in the form of a prepolymer.
本発明は上記した成分を上記の記載の如く混練して本発
明のポリエーテルイミド変性シアナト樹脂を調製する。In the present invention, the polyetherimide-modified cyanato resin of the present invention is prepared by kneading the above-mentioned components as described above.
まず、第１段階の（ａ）、ポリエーテルイミドと（ｂ）
、結晶融点１９０〜２５０℃の熱可塑性ポリエステルエ
ラストマーを混練して混練物（Ａ１）とする条件は好適
には温度２８０〜３２０℃において画成分を混練して好
適には２４０℃以下の温度において溶融混練可能な混練
物（Ａ１）を調製するものである。ついで第２段階の該
混練物（Ａ１）と（ｃ）、低結晶性乃至非結晶性の熱可
塑性ポリエステルを混練して混練物（Ａ２）とするには
温度２００〜２４０℃において画成分を混練して好適に
は１４０℃以下の温度において溶融混練可能な混練物（
八２）を調製するものである。最終段階は上記で製造し
た混練物（Ａ２）とシアナト樹脂（Ｂ）とを好適には温
度１００〜１４０℃で混練することによって本発明のポ
リエーテルイミド変性シアナト樹脂を得る。ここに混練
は押出機、ニーダ、ロールなどが適宜使用されるもので
ある。First, in the first step (a), polyetherimide and (b)
The conditions for kneading a thermoplastic polyester elastomer with a crystal melting point of 190 to 250°C to obtain a kneaded product (A1) are preferably kneading the image components at a temperature of 280 to 320°C, and preferably melting at a temperature of 240°C or lower. A kneaded material (A1) that can be kneaded is prepared. Next, in the second step, the kneaded products (A1) and (c) and a low-crystalline to non-crystalline thermoplastic polyester are kneaded to obtain a kneaded product (A2), in which the image components are kneaded at a temperature of 200 to 240°C. A kneaded material that can be melt-kneaded (
82). In the final step, the kneaded product (A2) produced above and the cyanato resin (B) are kneaded preferably at a temperature of 100 to 140°C to obtain the polyetherimide-modified cyanato resin of the present invention. For kneading, an extruder, kneader, roll, etc. are used as appropriate.
また、組成比としては、第１段階の（ａ）、ポリエーテ
ルイミドと（ｂ）、結晶融点１９０〜２５０℃の熱可塑
性ポリエステルエラストマーとは（ａ）／（ｂ）−９／
１〜５１５、好適には８７２〜５１５であり、第２段階
の該混練物（Ａ１）と（ｃ）、低結晶性乃至非結晶性の
熱可塑性ポリエステルとは（Ａｌ）／（ｃ）−９／１〜
５１５、好適には８７２〜５１５である。更に混練物（
Ａ２）とシアナト樹脂（ロ）とは（Ａ２） ／ （Ｂ）
＝５／９５〜６０／４０、好適には１０／９０〜５０
１５０の範囲から選択する。In addition, the composition ratio of (a) in the first stage, polyetherimide (b), and thermoplastic polyester elastomer with a crystal melting point of 190 to 250°C is (a)/(b)-9/
1 to 515, preferably 872 to 515, and the kneaded product (A1) and (c) in the second stage, the low crystallinity to amorphous thermoplastic polyester are (Al)/(c)-9 /1～
515, preferably 872-515. Furthermore, the kneaded material (
What is A2) and cyanato resin (B)? (A2) / (B)
=5/95 to 60/40, preferably 10/90 to 50
Choose from a range of 150.
本発明は上記の如きものであるが上記の方法を損なわな
い範囲において、特に最終段階において、必要に応じて
、熱硬化性のモノマーもしくはプレポリマー、樹脂成分
を配合した組成物としても使用することが出来るし、更
にその他の繊維質補強材、充填材、染料、顔料、増粘剤
、滑剤、カップリング剤、難燃剤などの公知の各種添加
剤類を混合したものとしても当然に使用できる。Although the present invention is as described above, it may also be used as a composition containing a thermosetting monomer, prepolymer, or resin component, if necessary, especially in the final stage, as long as the above method is not impaired. Furthermore, it can also be used as a mixture with various known additives such as other fibrous reinforcing materials, fillers, dyes, pigments, thickeners, lubricants, coupling agents, and flame retardants.
ここに熱硬化性のモノマーもしくはプレポリマーとして
は、多官能性（メタ）アクリレート、アルキル（メタ）
アクリレート、エポキシ（メタ）アクリレートなどのポ
リ （メタ）アクリレート類；ジアリルフタレート、ジ
ビニルベンゼン、ジアリルベンゼン、トリアルケニルイ
ソシアヌレートなどのポリアリル化合物及びそのプレポ
リマー；ジシクロペンタジェン及びそのプレポリマー；
フェノール樹脂；キシレン樹脂；多官能性エポキシ化合
物；多官能性マレイミド化合物などの公知の樹脂類が例
示される。また、樹脂成分としては、ポリビニルホルマ
ール、ポリビニルアセタール、ポリビニルブチラールな
どのポリビニルアセタール樹脂；フェノキシ樹脂；Ｏ１
１基もしくはＣＯ叶基をもったアクリル樹脂；シリコン
樹脂；アルキッド樹脂；熱可塑性ポリウレタン樹脂；ポ
リブタジェン、ブタジェン−アクリロニトリル共重合体
、ポリクロロプレン、ブタジェン−スチレン共重合体、
ポリイソプレン、ブチルゴム、天然ゴムなどの無架橋（
無加硫）のゴム類；ポリエチレン、ポリプロピレン、ポ
リブテン、ポリ−４−メチルペンテン−１、ポリ塩化ビ
ニル、塩化ビニリデン樹脂、ポリスチレン、ポリビニル
トルエン、ポリビニルフェノール、ＡＳ樹脂、ＡＢＳ樹
脂、ＭＢＳ樹脂、ポリ−４−フッ化エチレン、フッ化エ
チレン−プロピレン共重合体、４−フッ化エチレン−６
−フッ化エチレン共重合体、フッ化ビニリデンなどのビ
ニル化合物重合体類；ポリカーボネート、ポリエステル
カーボネート、ポリフェニレンエーテル、ポリエステル
、ポリアミド、ポリアトイミド、ポリエステルイミド、
ポリフェニレンサルファイドなどの樹脂類並びにこれら
の熱可塑性樹脂の低重合物である分子量が１万以下、通
常、千〜数千の低分子量重合体（プレポリマー）を挙げ
らことかできる。又、本発明においてはシアナト樹脂の
公知の触媒を必要に応じて併用できるものである。この
ような触媒としては、過酸化ベンゾイル、ラウロイルパ
ーオキサイド、ジーｔｅｒｔ−ブチルーパーオキサイド
、ジクミルパーオキサイド、ジ−ｔ−ブチルパーフタレ
ートなどの有機過酸化物；２−メチルイミダゾール、２
−エチル−４−メチルイミダゾールなどのイミダゾール
類；トリエチルアミン、Ｎ−メチルピペリジンなどの第
三級アミン；フェノール、クレゾールなどのフェノール
類；ナフテン酸亜鉛、ステアリン酸鉛、ナフテン酸鉛、
オクチル酸亜鉛、オレイン酸銀、オクチル酸錫、ジブチ
ル錫マレート、ナフテン酸マンガン、テフテン酸コバル
トなどの有機金属塩類；アセチルアセトン鉄、アセチル
アセトン銅、アセチルアセトンコバルトなどの金属キレ
ート化合物；ジオルガノ錫オキサイドなどの有機スズ化
合物；無水トリメリット酸、無水フタル酸などの酸無水
物などが挙げられる。Examples of thermosetting monomers or prepolymers include polyfunctional (meth)acrylates and alkyl (meth)acrylates.
Poly(meth)acrylates such as acrylate and epoxy(meth)acrylate; polyallyl compounds and prepolymers thereof such as diallyl phthalate, divinylbenzene, diallylbenzene, and trialkenyl isocyanurate; dicyclopentadiene and prepolymers thereof;
Known resins such as phenol resin; xylene resin; polyfunctional epoxy compound; polyfunctional maleimide compound are exemplified. In addition, as a resin component, polyvinyl acetal resin such as polyvinyl formal, polyvinyl acetal, polyvinyl butyral; phenoxy resin; O1
Acrylic resin with one or CO group; silicone resin; alkyd resin; thermoplastic polyurethane resin; polybutadiene, butadiene-acrylonitrile copolymer, polychloroprene, butadiene-styrene copolymer,
Non-crosslinked materials such as polyisoprene, butyl rubber, and natural rubber (
(unvulcanized) rubber; polyethylene, polypropylene, polybutene, poly-4-methylpentene-1, polyvinyl chloride, vinylidene chloride resin, polystyrene, polyvinyltoluene, polyvinylphenol, AS resin, ABS resin, MBS resin, poly- 4-fluoroethylene, fluoroethylene-propylene copolymer, 4-fluoroethylene-6
-Vinyl compound polymers such as fluorinated ethylene copolymers and vinylidene fluoride; polycarbonate, polyester carbonate, polyphenylene ether, polyester, polyamide, polyaimide, polyester imide,
Examples include resins such as polyphenylene sulfide, and low molecular weight polymers (prepolymers) of thermoplastic resins having a molecular weight of 10,000 or less, usually 1,000 to several thousand. Further, in the present invention, a known catalyst for cyanato resin can be used in combination as required. Such catalysts include organic peroxides such as benzoyl peroxide, lauroyl peroxide, di-tert-butyl peroxide, dicumyl peroxide, and di-t-butyl perphthalate; 2-methylimidazole,
-Imidazoles such as ethyl-4-methylimidazole; Tertiary amines such as triethylamine and N-methylpiperidine; Phenols such as phenol and cresol; zinc naphthenate, lead stearate, lead naphthenate,
Organometallic salts such as zinc octylate, silver oleate, tin octylate, dibutyltin malate, manganese naphthenate, and cobalt tephthenate; metal chelate compounds such as iron acetylacetonate, copper acetylacetone, and cobalt acetylacetone; organotins such as diorganotin oxide Compounds include acid anhydrides such as trimellitic anhydride and phthalic anhydride.
以下、実施例等により本発明を説明する。尚、実施例等
中の部、％は重量基準である。The present invention will be explained below with reference to Examples. Note that parts and percentages in Examples and the like are based on weight.
実施例１
ポリエーテルイミド （商品名：ウルテム１０００、米
国ＧＥＥ社製、以下ｒ ｔｌＬｌｏｏｏＪと記す）を１
４０℃で４時間乾燥したものとポリエステルエラストマ
ー（商品名；ペルプレン５２００１ 、東洋紡績９１製
、以下ｒｓ２００１ Ｊと記す）を１２０℃で６時間乾
燥したものとを用い、第１表に記載した組成で混練して
混練物（Ａ１）を得た。なお、混練は２軸のＬ／Ｄ＝１
０．２； Ｄ＝２５ｍｍニーグーを用い温度２９０℃で
滞留時間１０分間とした。Example 1 Polyetherimide (trade name: Ultem 1000, manufactured by GEE, USA, hereinafter referred to as r tlLloooJ) was
Using polyester elastomer (trade name: Pelprene 52001, manufactured by Toyobo 91, hereinafter referred to as RS2001 J) dried at 40°C for 4 hours and dried at 120°C for 6 hours, the compositions listed in Table 1 were used. The mixture was kneaded to obtain a kneaded product (A1). In addition, the kneading is performed using two axes L/D = 1.
0.2; D = 25 mm Niegu was used at a temperature of 290° C. and a residence time of 10 minutes.
この混練物Ａ１と非結晶性ポリエステル樹脂（商品名；
ニチゴーポリエスターＬＰ−０３５、日本合成化学工業
■製、以下ｒ ＬＰ−０３５Ｊと記す）とを上記と同じ
ニーダ−を用い温度２２０℃、１０分間の条件で混練し
て混練物（Ａ２）を得た。This kneaded material A1 and amorphous polyester resin (trade name;
Nichigo Polyester LP-035 (manufactured by Nippon Gosei Kagaku Kogyo ■, hereinafter referred to as r LP-035J) was kneaded using the same kneader as above at a temperature of 220°C for 10 minutes to obtain a kneaded product (A2). Ta.
この混練物Ａ２２５０ｇに４０ｇの２．２−ビス（４−
シアナトフェニル）プロパンプレポリマー（ＭＷ＝１４
００゜Ｍｎ＝４００、以下「トリアジン」と記す）を混
合した後、２本ロール（１２ｃｍφ、長さ３０印）で１
２０℃。To 2250 g of this kneaded material A, 40 g of 2.2-bis(4-
cyanatophenyl) propane prepolymer (MW=14
00゜Mn=400, hereinafter referred to as "triazine"), and then rolled with two rolls (12 cmφ, length 30 marks).
20℃.
４０分間混練した。The mixture was kneaded for 40 minutes.
この混練物２９０ｇを取り出し、１１０℃に加熱した後
、１２０℃のリボン翼ニーグーに入れ、撹拌しつつ後、
トリアジンを少しづつ添加して合計１時間の混練を行い
冷却した。290g of this kneaded material was taken out and heated to 110°C, then placed in a ribbon-blade Nigu at 120°C, and while stirring,
Triazine was added little by little, kneading was carried out for a total of 1 hour, and the mixture was cooled.
上記の混練後の混合物は室温で粘凋な半固形樹脂であっ
た。The above-mentioned mixture after kneading was a semi-solid resin that was viscous at room temperature.
該樹脂をプレスして厚み３Ｉｎｆｆｌの平板とし、２４
０℃で２０時間加熱・硬化した。The resin was pressed into a flat plate with a thickness of 3 Inffl, and 24
It was heated and cured at 0°C for 20 hours.
この硬化物の試験結果を第１表に示した。The test results of this cured product are shown in Table 1.
尚、試験Ｎα６のＬＰ−０３５とトリアジンとの組成物
は２本ロール１２０℃、４０分の条件によるものである
。The composition of LP-035 and triazine in test Nα6 was prepared using two rolls at 120° C. for 40 minutes.
更に、ポリエーテルイミドとトリアジンとの組成物の調
製を５２００１又はＬＰ−０３５を除いて試みたがいず
れの場合も均一な組成物とはならなかった。Further, attempts were made to prepare compositions of polyetherimide and triazine except for 52001 or LP-035, but in no case did a uniform composition result.
第１表 注）＊：煮沸１００℃、８７時間後の測定値である。Table 1 Note) *: Measured value after boiling at 100°C for 87 hours.
第１表−２ 注）＊：煮沸１００℃、８７時間後の測定値である。Table 1-2 Note) *: Measured value after boiling at 100°C for 87 hours.
以上の如く、本発明の製造法による組成物は強度の増加
が著しく、かつ有機溶剤を全く使用せずに得られるもの
であることから、工業的に良いに実施できるものである
。As described above, the composition produced by the production method of the present invention has a remarkable increase in strength and can be obtained without using any organic solvent, so it can be easily implemented industrially.
Claims (1)
〜２５０℃の熱可塑性ポリエステルエラストマーを混練
して混練物（Ａ１）とし、該混練物（Ａ１）と（ｃ）、
低結晶性乃至非結晶性の熱可塑性ポリエステルを混練し
て混練物（Ａ２）とし、この混練物（Ａ２）とシアナト
樹脂（Ｂ）とを混練してなることを特徴とするポリエー
テルイミド変性シアナト樹脂の製造法。(a), polyetherimide and (b), crystal melting point 190
A thermoplastic polyester elastomer at ~250°C is kneaded to obtain a kneaded product (A1), and the kneaded product (A1) and (c),
A polyetherimide-modified cyanate characterized by kneading a low-crystalline to non-crystalline thermoplastic polyester to obtain a kneaded product (A2), and kneading this kneaded product (A2) with a cyanato resin (B). Method of manufacturing resin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16586788A JP2623714B2 (en) | 1988-07-05 | 1988-07-05 | Method for producing polyetherimide-modified cyanato resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16586788A JP2623714B2 (en) | 1988-07-05 | 1988-07-05 | Method for producing polyetherimide-modified cyanato resin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0216159A true JPH0216159A (en) | 1990-01-19 |
| JP2623714B2 JP2623714B2 (en) | 1997-06-25 |
Family
ID=15820492
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16586788A Expired - Lifetime JP2623714B2 (en) | 1988-07-05 | 1988-07-05 | Method for producing polyetherimide-modified cyanato resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2623714B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0685107A (en) * | 1992-03-10 | 1994-03-25 | Internatl Business Mach Corp <Ibm> | Electronic circuit package and its manufacture |
| WO2006101219A1 (en) * | 2005-03-23 | 2006-09-28 | Lintec Corporation | Adhesive sheet |
-
1988
- 1988-07-05 JP JP16586788A patent/JP2623714B2/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0685107A (en) * | 1992-03-10 | 1994-03-25 | Internatl Business Mach Corp <Ibm> | Electronic circuit package and its manufacture |
| WO2006101219A1 (en) * | 2005-03-23 | 2006-09-28 | Lintec Corporation | Adhesive sheet |
| US8282765B2 (en) | 2005-03-23 | 2012-10-09 | Lintec Corporation | Adhesive sheet |
| KR101249551B1 (en) * | 2005-03-23 | 2013-04-01 | 린텍 가부시키가이샤 | Adhesive sheet |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2623714B2 (en) | 1997-06-25 |
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