JPH0329088B2 - - Google Patents
Info
- Publication number
- JPH0329088B2 JPH0329088B2 JP58217804A JP21780483A JPH0329088B2 JP H0329088 B2 JPH0329088 B2 JP H0329088B2 JP 58217804 A JP58217804 A JP 58217804A JP 21780483 A JP21780483 A JP 21780483A JP H0329088 B2 JPH0329088 B2 JP H0329088B2
- Authority
- JP
- Japan
- Prior art keywords
- elastomer
- polymer
- copolymer
- ethylene
- polystyrene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 51
- 229920001577 copolymer Polymers 0.000 claims description 27
- 229920001971 elastomer Polymers 0.000 claims description 26
- 239000000806 elastomer Substances 0.000 claims description 26
- -1 polyoxymethylene Polymers 0.000 claims description 24
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 13
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 claims description 13
- 150000004292 cyclic ethers Chemical class 0.000 claims description 12
- 229920001400 block copolymer Polymers 0.000 claims description 10
- 229920006324 polyoxymethylene Polymers 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 7
- 239000004793 Polystyrene Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229920002223 polystyrene Polymers 0.000 claims description 7
- 230000007704 transition Effects 0.000 claims description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 4
- 229920006124 polyolefin elastomer Polymers 0.000 claims description 4
- 229920001897 terpolymer Polymers 0.000 claims description 4
- 229920002725 thermoplastic elastomer Polymers 0.000 claims description 4
- AUAGGMPIKOZAJZ-UHFFFAOYSA-N 1,3,6-trioxocane Chemical compound C1COCOCCO1 AUAGGMPIKOZAJZ-UHFFFAOYSA-N 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000002685 polymerization catalyst Substances 0.000 description 14
- 238000006116 polymerization reaction Methods 0.000 description 13
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000000704 physical effect Effects 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
- 238000010538 cationic polymerization reaction Methods 0.000 description 6
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 5
- 229920001195 polyisoprene Polymers 0.000 description 5
- 229920002943 EPDM rubber Polymers 0.000 description 4
- 239000005062 Polybutadiene Substances 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- KQBSGRWMSNFIPG-UHFFFAOYSA-N trioxane Chemical compound C1COOOC1 KQBSGRWMSNFIPG-UHFFFAOYSA-N 0.000 description 4
- 229910015900 BF3 Inorganic materials 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- SFXNZFATUMWBHR-UHFFFAOYSA-N 2-morpholin-4-yl-2-pyridin-3-ylacetonitrile Chemical compound C=1C=CN=CC=1C(C#N)N1CCOCC1 SFXNZFATUMWBHR-UHFFFAOYSA-N 0.000 description 2
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 230000000397 acetylating effect Effects 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- LZTCQASULATCDM-UHFFFAOYSA-M dimethyl(dioctadecyl)azanium;acetate Chemical compound CC([O-])=O.CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC LZTCQASULATCDM-UHFFFAOYSA-M 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-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
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 1
- SYIUWAVTBADRJG-UHFFFAOYSA-N 2H-pyran-2,6(3H)-dione Chemical compound O=C1CC=CC(=O)O1 SYIUWAVTBADRJG-UHFFFAOYSA-N 0.000 description 1
- CXURGFRDGROIKG-UHFFFAOYSA-N 3,3-bis(chloromethyl)oxetane Chemical group ClCC1(CCl)COC1 CXURGFRDGROIKG-UHFFFAOYSA-N 0.000 description 1
- ZOIYTANKOJAEIM-UHFFFAOYSA-N 3,4-didehydrofuran-2,5-dione Chemical compound O=C1OC(=O)C#C1 ZOIYTANKOJAEIM-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 229920012196 Polyoxymethylene Copolymer Polymers 0.000 description 1
- 229920009382 Polyoxymethylene Homopolymer Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- 229910021623 Tin(IV) bromide Inorganic materials 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 229910021551 Vanadium(III) chloride Inorganic materials 0.000 description 1
- WPNRZVONKRBZDU-UHFFFAOYSA-L [dodecanoyloxy(diethyl)stannyl] dodecanoate Chemical compound CC[Sn+2]CC.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O WPNRZVONKRBZDU-UHFFFAOYSA-L 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940088990 ammonium stearate Drugs 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- KHPJLRRQWDDJDW-UHFFFAOYSA-N anthracene;potassium Chemical compound [K].C1=CC=CC2=CC3=CC=CC=C3C=C21 KHPJLRRQWDDJDW-UHFFFAOYSA-N 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- JPNZKPRONVOMLL-UHFFFAOYSA-N azane;octadecanoic acid Chemical compound [NH4+].CCCCCCCCCCCCCCCCCC([O-])=O JPNZKPRONVOMLL-UHFFFAOYSA-N 0.000 description 1
- GJOFTLVFRFBVTI-UHFFFAOYSA-N benzyl(trimethyl)phosphanium;ethanolate Chemical compound CC[O-].C[P+](C)(C)CC1=CC=CC=C1 GJOFTLVFRFBVTI-UHFFFAOYSA-N 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- ZXDVQYBUEVYUCG-UHFFFAOYSA-N dibutyltin(2+);methanolate Chemical compound CCCC[Sn](OC)(OC)CCCC ZXDVQYBUEVYUCG-UHFFFAOYSA-N 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical class C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 description 1
- FKZRUGSMXUERAD-UHFFFAOYSA-L magnesium;hexanoate Chemical compound [Mg+2].CCCCCC([O-])=O.CCCCCC([O-])=O FKZRUGSMXUERAD-UHFFFAOYSA-L 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- HPVRLMGCBINLBH-UHFFFAOYSA-N methanolate;tetrabutylazanium Chemical compound [O-]C.CCCC[N+](CCCC)(CCCC)CCCC HPVRLMGCBINLBH-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- JFNWATIZEGZGSY-UHFFFAOYSA-N n,n-diethylethanamine;trifluoroborane Chemical compound FB(F)F.CCN(CC)CC JFNWATIZEGZGSY-UHFFFAOYSA-N 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- URXNVXOMQQCBHS-UHFFFAOYSA-N naphthalene;sodium Chemical compound [Na].C1=CC=CC2=CC=CC=C21 URXNVXOMQQCBHS-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- UHHKSVZZTYJVEG-UHFFFAOYSA-N oxepane Chemical compound C1CCCOCC1 UHHKSVZZTYJVEG-UHFFFAOYSA-N 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- NAHIZHJHSUSESF-UHFFFAOYSA-N perchloryl acetate Chemical compound CC(=O)OCl(=O)(=O)=O NAHIZHJHSUSESF-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229940114930 potassium stearate Drugs 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
- OYNYQOJNEQMVMJ-UHFFFAOYSA-M propanoate;tetramethylphosphanium Chemical compound CCC([O-])=O.C[P+](C)(C)C OYNYQOJNEQMVMJ-UHFFFAOYSA-M 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- UDWXLZLRRVQONG-UHFFFAOYSA-M sodium hexanoate Chemical compound [Na+].CCCCCC([O-])=O UDWXLZLRRVQONG-UHFFFAOYSA-M 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- MCZDHTKJGDCTAE-UHFFFAOYSA-M tetrabutylazanium;acetate Chemical compound CC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MCZDHTKJGDCTAE-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- HQYCOEXWFMFWLR-UHFFFAOYSA-K vanadium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[V+3] HQYCOEXWFMFWLR-UHFFFAOYSA-K 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Description
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The present invention relates to a novel acetal copolymer, and particularly to a method for producing a novel acetal copolymer having unprecedentedly excellent impact resistance and fatigue resistance. Polyacetal is usually obtained by homopolymerizing formaldehyde or trioxane, or by copolymerizing formaldehyde or trioxane with a cyclic ether. Japanese Patent Publication No. 35-9435 states that the molecular weight of a formaldehyde polymer is determined by the amounts of trace amounts of water, methanol, and formic acid present in the polymerization system. Further, US Pat. No. 3,017,389 describes that formaldehyde is polymerized in the coexistence of a chain transfer agent such as an alcohol, ester, acid anhydride, amide, or imide. Furthermore, Japanese Patent Publication No. 35-2194 discloses that formaldehyde is polymerized in the presence of polymers such as polytetramethylene glycol, vinyl acetate copolymer, and methyl methacrylate/vinyloxymethylmethylamine copolymer. ing. The polyoxymethylene block copolymer produced using this method has slightly improved toughness, but has a significant decrease in strength. In other words, this copolymer has too much flexibility, resulting in a significant decrease in strength and rigidity. This will also become clear in the comparative examples later on. Acetal polymers are useful as engineering plastics due to their well-balanced physical properties. Attempts to improve toughness such as elongation and impact value even at the expense of strength and rigidity, as in the case of the copolymer of the present invention, cannot necessarily be said to be an advantageous direction. The present inventors extensively studied molecular weight regulators to be used during polymerization and found that a certain elastomer functions well as a molecular weight regulator. As a result, this is not found in conventional acetal polymers. We have discovered a new acetal copolymer that has both extremely excellent impact resistance and fatigue resistance. Moreover, this copolymer has improved toughness while maintaining high strength and rigidity. Therefore, the copolymers of the present invention can be appropriately called highly balanced polymers. That is, the present invention provides a thermoplastic elastomer having a soft segment and a hard segment, a second-order transition temperature (Tg, glass transition temperature) of -120 to +40°C, and at least one carboxylic anhydride group. This is a novel method for producing acetal copolymers, in which formaldehyde is homopolymerized or formaldehyde or polyoxymethylene is copolymerized with a cyclic ether. The present invention will be specifically explained below. In the present invention, a thermoplastic elastomer having at least one carboxylic anhydride group in the polymer is used as a molecular weight regulator in the homopolymerization of formaldehyde or the copolymerization of formaldehyde or polyoxymethylene with a cyclic ether. The elastomer that can be used in the present invention is a thermoplastic polymer, consisting of an amorphous segment with a low secondary transition temperature (soft segment) and a segment that creates a thermoreversible crosslinked/bonded structure (hard segment). It is a copolymer with -120 to +
It is a polymer with a second-order transition temperature of 40°C. Here, the second-order transition temperature of the elastomer is â120 to
It is necessary that the temperature be between +40â. An improvement in the impact resistance of the resulting acetal copolymers is observed only when using elastomers with secondary transition temperatures between -120 and +40°C. The elastomer functions as a molecular weight regulator during the polymerization reaction, and at the same time controls the molecular weight of the polymer.
It is incorporated into the polymer as a blocking macromer. The first elastomer that can be used in the present invention
This group includes polyolefin elastomers, such as unsaturated compound-modified ethylene-propylene copolymers and unsaturated compound-modified ethylene-propylene-diene terpolymers. The dienes copolymerized with ethylene and propylene as termonomers include dicyclopentadiene, ethylidene norbornene, methylene norbornene, 1,4
-Hexadiene, etc. Ethylene-propylene copolymers (EPM), ethylene-propylene-diene terpolymers (EPDM) can be prepared in the presence or absence of peroxides by maleic anhydride, methylmaleic anhydride, itaconic anhydride, citraconic anhydride, It is modified with unsaturated compounds such as glutaconic anhydride, muconic anhydride, acetylene dicarboxylic anhydride, and phthalic anhydride. In the present invention, ethylene-propylene copolymers and ethylene-propylene-diene terpolymers modified with unsaturated compounds are used. Specifically, maleic anhydride-modified ethylene-propylene copolymer (2 carboxylic anhydride groups), maleic anhydride-modified ethylene-propylene-ethylidene norbornene terpolymer (~10 carboxylic anhydride groups), itaconic anhydride-modified ethylene-propylene. There are copolymers (one carboxylic anhydride group), citraconic anhydride-modified ethylene-propylene-dicyclopentadiene terpolymers (five carboxylic anhydride groups), and the like. The second group of elastomers are polystyrene-based elastomers, which are unsaturated compound-modified elastomers that have polystyrene as a hard segment. Soft segments to be combined with polystyrene include diene polymers such as polybutadiene and polyisoprene, and hydrogenated diene polymers such as hydrogenated polybutadiene and hydrogenated polyisoprene. The unsaturated compound used to modify the polystyrene elastomer is the same as the compound used to modify the polyolefin elastomer. Specifically, maleic anhydride-modified polystyrene-polyisoprene block copolymer (2 carboxylic anhydride groups), maleic anhydride-modified hydrogenated polystyrene-polybutadiene block copolymer (~10 carboxylic anhydride groups), itaconic anhydride-modified polystyrene. -Polyisoprene block copolymer (5 carboxylic anhydride groups), citraconic anhydride-modified polystyrene-polybutadiene block copolymer (1 carboxylic anhydride group), and the like. Prior to polymerization, elastomers are washed, adsorbed,
It is preferable that it be purified by methods such as drying.
Further, these elastomers can be used alone, or two or more of them can be mixed and subjected to polymerization. In the polymerization of the present invention, sufficiently purified formaldehyde, polyoxymethylene, and cyclic ether are used as starting materials for the acetal copolymer. Here, polyoxymethyllene is a homopolymer of formaldehyde or trioxane,
For example, the number average molecular weight is preferably 10,000 to 500,000
30,000 to 150,000. The first group of cyclic ethers has the general formula (R 0 : selected from hydrogen, alkyl group, and aryl group, each of which may be the same or different. m
There are alkylene oxides represented by =2 to 6). For example, ethylene oxide, propylene oxide, butylene oxide, epichlorohydrin,
Examples include styrene oxide, oxetane, 3,3-bis(chloromethyl)oxetane, tetrahydrofuran, oxepane, and the like. Among these alkylene oxides, ethylene oxide is particularly preferred. The second group of cyclic ethers has the general formula There is a cyclic formal represented by For example, ethylene glycol formal, propylene glycol formal, diethylene glycol formal, triethylene glycol formal, 1,4
-butanediol formal, 1,5-pentanediol formal, and 1,6-hexanediol formal. Among these cyclic formals, ethylene glycol formal, diethylene glycol formal and 1,4-butanediol formal are particularly preferred. Cyclic ether, based on 100 parts by weight of starting materials,
0.03 to 100 parts by weight, more preferably 0.1 to 50 parts by weight are used. Generally, an anionic polymerization catalyst is used for the homopolymerization of formaldehyde in the present invention, and a cationic polymerization catalyst or an anionic polymerization catalyst and a cationic polymerization catalyst is used for the copolymerization of formaldehyde and a cyclic ether. Further, a cationic polymerization catalyst is usually used for copolymerization (reaction) of polyoxymethylene and cyclic ether. Anionic polymerization catalyst used in the polymerization of the present invention,
Cationic polymerization catalysts are the following compounds. Typical groups of anionic polymerization catalysts include alkali metals such as sodium and potassium, alkali metal complexes such as sodium-naphthalene and potassium-anthracene, alkali metal hydrides such as sodium hydride, and alkaline earths such as calcium hydride. metal hydrides, alkali metal alkoxides such as sodium methoxide and potassium t-butoxide, alkali metal carboxylates such as sodium caproate and potassium stearate, alkaline earth metal carboxylates such as magnesium caproate and calcium stearate, Amines such as n-butylamine, diethylamine, trioctylamine, pyridine, ammonium stearate,
Quaternary ammonium salts such as tetrabutylammonium methoxide and dimethyldistearylammonium acetate; phosphonium salts such as tetramethylphosphonium propionate and trimethylbenzylphosphonium ethoxide; quaternary ammonium salts such as tributyltin chloride, diethyltin dilaurate, and dibutyltin dimethoxide Examples include valent organic tin compounds, alkyl metals such as n-butyllithium, and ethylmagnesium chloride. Cationic polymerization catalysts include tin tetrachloride, tin tetrabromide, titanium tetrachloride, aluminum trichloride, zinc chloride, vanadium trichloride, antimony pentafluoride, boron trifluoride, boron trifluoride diethyl etherate,
So-called Friedel-Crafts type compounds such as boron trifluoride coordination compounds such as boron trifluoride acetic anhydrate and boron trifluoride triethylamine complex compounds, perchloric acid, acetyl perchlorate, hydroxyacetic acid, trichloroacetic acid, Inorganic and organic acids such as p-toluenesulfonic acid, complex salt compounds such as triethyloxonium tetrafluoroborate, triphenylmethylhexafluoroantimonate, allyldiazonium hexafluorophosphate, allyldiazonium tetrafluoroborate, diethylzinc, triethyl aluminum,
Examples include alkyl metals such as diethylaluminum chloride. These anionic polymerization catalysts and cationic polymerization catalysts are used in an amount of 0.0005 to 5 parts by weight based on 100 parts by weight of the starting material. Polymerization is carried out without a solvent or in an organic medium. Organic media that can be used in the present invention include aliphatic hydrocarbons such as n-pentane, n-hexane, n-heptane, n-octane, cyclohexane, and cyclopentane, benzene, toluene,
Examples include aromatic hydrocarbons such as xylene, halogenated aliphatic hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, and trichloroethylene, and halogenated aromatic hydrocarbons such as chlorobenzene and o-dichlorobenzene. These organic media may be used alone or in combination of two or more. The elastomer, which is a molecular weight regulator, is used after being uniformly dissolved or dispersed in the reaction system. The concentration of the molecular weight regulator in the system can be easily determined by experiment, depending on the molecular weight requirements of the desired acetal copolymer. The polymerization temperature is usually set between -20 and 230°C, but preferably between 20 and 210°C when using no solvent, and between -10 and 120°C when using an organic medium.
It is more preferable. There are no particular restrictions on polymerization time, but from 5 seconds to
Set between 300 minutes. After a predetermined period of time has elapsed, a terminator is added to the reaction system to complete the polymerization reaction. The obtained polymer is stabilized by removing unstable ends by hydrolysis or blocking unstable ends by a method such as esterification. The stabilized acetal copolymer is put into practical use with the addition of a stabilizer and the like. The features of the acetal copolymer of the present invention and its production method which have been described in detail above are listed below. (1) The acetal copolymer has extremely high impact resistance, fatigue resistance, toughness, strength, and rigidity. (2) By using a specific elastomer, it is possible to impart excellent performance to the acetal copolymer, and at the same time, the molecular weight of the polymer can be controlled arbitrarily. Measurement items in the following examples are as follows. MI: 2,2-methylene-bis(4-
methyl-6-tert-butylphenol) 0.25 parts,
0.50 part of nylon 6,6 was added and pelletized using a 50 mmÏ extruder. The MI of this pellet is
Measured according to ASTM-D1238-57T, MI is a measure of molecular weight. Izot impact value (notched): The above pellet was molded into a flat plate using an injection molding machine. A test piece was cut from this flat plate and measured according to ASTM-D256. The larger the Izot impact value, the better the impact resistance. Vibration fatigue characteristics: Cut a test piece from a flat plate,
Measured at 20°C and repeated vibration cycles of 1800 times/min in accordance with ASTM-D671. 10 The maximum stress that does not cause the specimen to break when subjected to repeated vibrations 6 times = fatigue strength is used as an index of fatigue resistance. The higher the fatigue strength, the better the fatigue resistance. Example 1 Formaldehyde gas with a purity of 99.9% was mixed at a rate of 100 parts (hereinafter, parts are by weight) per hour,
61.5 gr/maleic anhydride modified ethylene-propylene copolymer (~10 carboxylic anhydride groups) as a molecular weight regulator, 3.5 x 10 -4 mol/ as a polymerization catalyst
The mixture was continuously fed into 500 parts of toluene containing dimethyl distearyl ammonium acetate for 3 hours. Toluene containing the elastomer and polymerization catalyst at the above concentrations was also continuously fed at a rate of 500 parts/hr for 3 hours, and the polymerization temperature was maintained at 62° C. during this period. The polymer was separated from toluene, washed and dried to obtain 389 parts of polymer. After acetylating this polymer, it was extracted in benzyl alcohol at 160° C. for 5 hours, but no unreacted elastomer was extracted. From this, it became clear that all the elastomer was inserted into the polymer. The physical properties of this polymer were as follows. MI 1.6 (g/10 minutes) Izot impact value 32.4 (Kgã»cm/cm) Fatigue strength 283 (Kg/cm 2 ) This polymer has the desired molecular weight and has excellent impact resistance and fatigue resistance. It has performance. Example 2 Formaldehyde was used as a molecular weight regulator at a ratio of 100 parts/hr and ethylene oxide at a ratio of 2.2 parts/hr.
65.2 gr/maleic anhydride modified hydrogenated polystyrene-polyisoprene block copolymer was continuously fed into 500 parts of toluene for 5 hours. Toluene containing elastomer at the above concentration was also continuously fed at a rate of 500 parts/hr for 5 hours.
Additionally, as polymerization catalysts, tetrabutylammonium acetate and boron trifluoride dibutyl etherate were continuously supplied through separate conduits at a rate of 0.03 parts/hr and 0.08 parts/hr, respectively, for 5 hours, and the polymerization temperature was maintained at 60°C during this time. did. The polymer was separated from toluene, then washed and dried to obtain 692 parts of polymer. After acetylating this polymer, it was extracted in benzyl alcohol at 160° C. for 5 hours, but no unreacted elastomer was extracted. From this, it became clear that all the elastomer was inserted into the polymer. The physical properties of this polymer are as follows. MI 2.8 (g/10 minutes) Izot impact value 268 (Kgã»cm/cm) Fatigue strength 26.9 (Kg/cm 2 ) This polymer also has a specified molecular weight and at the same time has excellent impact resistance. . Example 3 Polyoxymethylene thoroughly dried under reduced pressure
5.08Kg, ethylene glycol formal 418gr,
A reaction tank was charged with 3.35 kg of maleic anhydride-modified ethylene-propylene-ethylidene nobornene terpolymer (3 carboxylic anhydride groups) and 50 kg of cyclohexane as molecular weight regulators. After charging, the contents of the reaction tank were heated to 70°C. The reaction was started by adding 1.25g of boron trifluoride dibutyl etherate to the reaction tank. After maintaining the internal temperature of the reaction tank at 70â for 32 minutes,
The reaction was stopped by adding 550 gr of cyclohexane containing 130 gr of tributylamine. After filtering off the polymer,
After washing with a large amount of methanol 5 times, 8.41 kg of polymer was recovered. Even by hot benzyl alcohol extraction of this polymer, no elastomer could be detected. From this, it became clear that all the elastomer was inserted into the polymer. The physical properties of this polymer are as follows. MI 12.3 (g/10 minutes) Izot impact value 28.4 (Kg·cm/cm) Fatigue strength 267 (Kg/cm 2 ) This polymer also has a desired molecular weight and excellent impact resistance. Examples 4 to 13 Using the starting materials and elastomers shown in Table 1, acetal copolymers having the physical properties shown in Table 1 were obtained. Both polymers have desired molecular weights and excellent impact resistance. Comparative Examples 1 to 4 Instead of the elastomer used in Example 1, the first
A block copolymer was obtained using a polymer having the active hydrogen shown in the table. The physical properties of these polymers are also shown in Table 1. A block copolymer of formaldehyde and a polymer having active hydrogen atoms shows almost no improvement in impact resistance.
At the same time, the fatigue strength also decreases significantly. The physical properties of the polyoxymethylene homopolymer are as follows. MI 12.2 (g/10 min) Izot impact value 6.8 (Kgã»cm/cm) Fatigue strength 330 (Kg/cm 2 ) Polyoxymethylene copolymer containing 1.5 mol% oxyethylene units obtained by copolymerization of trioxane and ethylene oxide The physical property values are as follows. MI 12.0 (g/10 minutes) Izot impact value 4.9 (Kgã»cm/cm) Fatigue strength 260 (Kg/cm 2 )
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Claims (1)
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ç©ã§ããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé èšèŒã®è£œæ³ã[Claims] 1. Formaldehyde alone in the presence of a thermoplastic elastomer that has soft segments and hard segments, has a secondary transition temperature of -120 to +40°C, and has at least one carboxylic anhydride group. A method for producing an acetal copolymer, which comprises polymerizing or copolymerizing formaldehyde or polyoxymethylene with a cyclic ether. 2. The manufacturing method according to claim 1, wherein the thermoplastic elastomer is a polyolefin elastomer or a polystyrene elastomer. 3. The manufacturing method according to claim 1 or 2, wherein the polyolefin elastomer is an unsaturated compound-modified ethylene-propylene copolymer or an unsaturated compound-modified ethylene-propylene-dien terpolymer. 4. The method according to claim 1 or 2, wherein the polystyrene elastomer is an unsaturated compound-modified polystyrene-polydiene block copolymer or an unsaturated compound-modified hydrogenated polystyrene-polydiene block copolymer. 5. The production method according to claim 1, wherein the cyclic ether is ethylene oxide. 6 The cyclic ether is ethylene glycol formal, diethylene glycol formal and 1,
The method according to claim 1, wherein the compound is selected from 4-butanediol formal.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP21780483A JPS60110714A (en) | 1983-11-21 | 1983-11-21 | Production of acetal copolymer |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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JP21780483A JPS60110714A (en) | 1983-11-21 | 1983-11-21 | Production of acetal copolymer |
Publications (2)
Publication Number | Publication Date |
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JPS60110714A JPS60110714A (en) | 1985-06-17 |
JPH0329088B2 true JPH0329088B2 (en) | 1991-04-23 |
Family
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Application Number | Title | Priority Date | Filing Date |
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JP21780483A Granted JPS60110714A (en) | 1983-11-21 | 1983-11-21 | Production of acetal copolymer |
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JP (1) | JPS60110714A (en) |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS60104116A (en) * | 1983-11-10 | 1985-06-08 | Asahi Chem Ind Co Ltd | Production of polyacetal |
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1983
- 1983-11-21 JP JP21780483A patent/JPS60110714A/en active Granted
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS60104116A (en) * | 1983-11-10 | 1985-06-08 | Asahi Chem Ind Co Ltd | Production of polyacetal |
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