JPS6333789B2 - - Google Patents
Info
- Publication number
- JPS6333789B2 JPS6333789B2 JP58131671A JP13167183A JPS6333789B2 JP S6333789 B2 JPS6333789 B2 JP S6333789B2 JP 58131671 A JP58131671 A JP 58131671A JP 13167183 A JP13167183 A JP 13167183A JP S6333789 B2 JPS6333789 B2 JP S6333789B2
- Authority
- JP
- Japan
- Prior art keywords
- rubber
- glycidyl
- copolymer
- formula
- group
- 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
Links
- 229920001577 copolymer Polymers 0.000 claims description 48
- 229920001971 elastomer Polymers 0.000 claims description 30
- 239000005060 rubber Substances 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- -1 acryloxy group Chemical group 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000005336 allyloxy group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003921 oil Substances 0.000 description 19
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 8
- 239000000178 monomer Substances 0.000 description 6
- 150000002924 oxiranes Chemical class 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 229920000800 acrylic rubber Polymers 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 230000007797 corrosion Effects 0.000 description 5
- 238000005260 corrosion Methods 0.000 description 5
- 230000006866 deterioration Effects 0.000 description 5
- 229920005558 epichlorohydrin rubber Polymers 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical group 0.000 description 5
- 239000010687 lubricating oil Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229920000058 polyacrylate Polymers 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- HAZJTCQWIDBCCE-UHFFFAOYSA-N 1h-triazine-6-thione Chemical class SC1=CC=NN=N1 HAZJTCQWIDBCCE-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- 229920000459 Nitrile rubber Polymers 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000004073 vulcanization Methods 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229920001973 fluoroelastomer Polymers 0.000 description 3
- 239000000295 fuel oil Substances 0.000 description 3
- 150000001451 organic peroxides Chemical class 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 150000003464 sulfur compounds Chemical class 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- YRRFZZZGXWNUOS-UHFFFAOYSA-N oxiran-2-ylmethyl 2-chloroacetate Chemical compound ClCC(=O)OCC1CO1 YRRFZZZGXWNUOS-UHFFFAOYSA-N 0.000 description 2
- 229920001084 poly(chloroprene) Polymers 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 150000003585 thioureas Chemical class 0.000 description 2
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 1
- JZFMNFJEQDUBPL-UHFFFAOYSA-N 1-sulfanyl-4,5-dihydroimidazole Chemical class SN1CCN=C1 JZFMNFJEQDUBPL-UHFFFAOYSA-N 0.000 description 1
- XSQHUYDRSDBCHN-UHFFFAOYSA-N 2,3-dimethyl-2-propan-2-ylbutanenitrile Chemical compound CC(C)C(C)(C#N)C(C)C XSQHUYDRSDBCHN-UHFFFAOYSA-N 0.000 description 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical group CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 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
- 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
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 229920000181 Ethylene propylene rubber Polymers 0.000 description 1
- PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- KFFQABQEJATQAT-UHFFFAOYSA-N N,N'-dibutylthiourea Chemical compound CCCCNC(=S)NCCCC KFFQABQEJATQAT-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 229920005557 bromobutyl Polymers 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229920006235 chlorinated polyethylene elastomer Polymers 0.000 description 1
- 239000007859 condensation product Substances 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
- ZXSBDSGRQIWJPM-UHFFFAOYSA-N dimethylcarbamothioic s-acid Chemical compound CN(C)C(S)=O ZXSBDSGRQIWJPM-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229920005561 epichlorohydrin homopolymer Polymers 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical group CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229920005555 halobutyl Polymers 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 229920002681 hypalon Polymers 0.000 description 1
- 229920003049 isoprene rubber Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- DZCCLNYLUGNUKQ-UHFFFAOYSA-N n-(4-nitrosophenyl)hydroxylamine Chemical compound ONC1=CC=C(N=O)C=C1 DZCCLNYLUGNUKQ-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000006864 oxidative decomposition reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- AVNANMSIFNUHNY-MQQKCMAXSA-N oxiran-2-ylmethyl (2e,4e)-hexa-2,4-dienoate Chemical compound C\C=C\C=C\C(=O)OCC1CO1 AVNANMSIFNUHNY-MQQKCMAXSA-N 0.000 description 1
- JKXONPYJVWEAEL-UHFFFAOYSA-N oxiran-2-ylmethyl acetate Chemical compound CC(=O)OCC1CO1 JKXONPYJVWEAEL-UHFFFAOYSA-N 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical group C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- QNAJAJLBHMMOJB-UHFFFAOYSA-N oxiran-2-ylmethyl propanoate Chemical compound CCC(=O)OCC1CO1 QNAJAJLBHMMOJB-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QXAGOFURPWCGAT-UHFFFAOYSA-N tetrathionane Chemical compound C1CCSSSSCC1 QXAGOFURPWCGAT-UHFFFAOYSA-N 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- CDMIYIVDILNBIJ-UHFFFAOYSA-N triazinane-4,5,6-trithione Chemical compound SC1=NN=NC(S)=C1S CDMIYIVDILNBIJ-UHFFFAOYSA-N 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
- SZNCKQHFYDCMLZ-UHFFFAOYSA-L zinc;propan-2-yloxymethanedithioate Chemical compound [Zn+2].CC(C)OC([S-])=S.CC(C)OC([S-])=S SZNCKQHFYDCMLZ-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
Description
æ¬çºæã¯æ°èŠãªèæ²¹æ§ãŽã çµæç©ã«é¢ãããåŸ
æ¥ä»£è¡šçãªèæ²¹æ§ãŽã ãšããŠã¢ã¯ãªã«ãããªã«â
ãã¿ãžãšã³å
±éåäœãŽã ããšãã¯ãã«ãããªã³ç³»
ãŽã ãã¢ã¯ãªã«ãŽã çãããã䜿çšç°å¢ã«å¿ããŠ
䜿ãåããããŠããããããè¿å¹Žã§ã¯çææ²¹ã最
æ»æ²¹ã®æåãå€åããŠããŠããã®ã§çš®ã
ã®åé¡ç¹
ãçããŠããŠãããããšãã°çææ²¹ã«ãããŠã¯è³
éŠæçåæ°ŽçŽ å«æéãå¢å ãããŸã最æ»æ²¹ã«ãã
ãŠã¯å皮添å å€ã®çš®é¡ãéãå¢å€§ããŠããã®ã§ã
ãããã«æ¥è§Šãããã¯æµžæŒ¬ããããŽã é¡ã¯ç©æ§ã®
äœäžãããã¯æ·»å ç©ã®äœçšã«ããå£åãæ¥ãã¬ã
ãã§ããã ãèæ§ãåäžãããå¿
èŠãçããŠã
ããäžæ¹ç©ºæ°äžã«ãããé
žåã«ãã€ãŠå£åãã
æ²¹ãããããé
žææ²¹çã«ããå£åçŸè±¡ãèæ²¹ãŽã
補åã®å€§ããªåé¡ã§ããã
ãã®çš®ã®åé¡ã®å¯ŸçãšããŠã¯å€ãã®å ŽååŒçŽ ãŽ
ã ããã®åªããæ§èœã«ãã代æ¿åãšããŠäœ¿çšãã
ãŠãããããã®ãŽã ã¯éåžžã«é«äŸ¡ã§ããäžã«èå¯
æ§ãèããå£ããšããæ¬ ç¹ãæã€ãŠãããäžè¬ã«
ãŽã ã¯èæ²¹æ§ã®åäžã«ã€ããŠèå¯æ§ã®äœäžããã®
ãéåžžã§ãããé«åºŠã®èæ²¹æ§ãšèå¯æ§ãšãå
Œåã
ããŽã ãšããŠã¯ãšãã¯ãã«ãããªã³âãšãã¬ã³ãª
ãã·ãå
±éåäœãŽã é¡ãç¥ãããŠããããåé¢ã
ã®ãŽã ã¯äžèšã®æ²¹äžã®å皮添å å€ãããã¯é
žææ²¹
ã«ããå£åãåããããããã®ããã«ãšãã¯ãã«
ãããªã³ç³»ãŽã ã¯ãã®ååæ§é äžãããªãšãŒãã«
äž»éã®é
žåå解ïŒé
žåå£åïŒãå¡©çŽ ã®ååšã«ãã
最æ»æ²¹æ·»å å€ã®åœ±é¿ãåããããããŸãéå±ã«å¯Ÿ
ããè
é£ã®å¯èœæ§ãåé¡ãšãªãã
ä»ã«ãããªã«ãŽã ã¯äžé£œåçµåã®ååšã«èµ·å ã
ãŠèãªãŸã³æ§ãæªãèåæã«èåãæããããã«
èæ²¹æ§ãšèå¯æ§ãšã®ãã©ã³ã¹ãæªãã
ãŸãã¢ã¯ãªã«ãŽã ã¯è最æ»æ²¹æ§ã«åªããããç
ææ²¹ã«å¯ŸããŠèããèæ§ã«ä¹ããèå¯æ§ãéåžžã«
å£ã€ãŠããã
ãã®ãããªç¶æ³ããé«åºŠã®èæ²¹æ§ãšèå¯æ§ãšã
å
Œåãããšãšãã«ãäžèšã®ãããªæ·»å å€ãé
žææ²¹
çã«å¯Ÿããèæ§ãæ¹åãããå®äŸ¡ãªãŽã ã®åºçŸã
æãŸããŠããã
æ¬çºæè
ãã¯ãããã®æ¡ä»¶ãæºãã¹ãéæç 究
ã®çµææ¬çºæã«å°éãããã®ã§ãããªãã¡æ¬çºæ
ã®äž»éæ§é ãäžèšã®åŒïŒïŒã§è¡šããããæ§é å
äœ10ã¢ã«ïŒ
以äžãšåŒïŒïŒã§è¡šããããæ§é åäœ
ããã³ïŒãããã¯åŒïŒïŒã§è¡šããããæ§é åäœ
ïŒã¢ã«ïŒ
以äžãšãããªãã80âïŒ0.1ïŒ
ã®ã¢ãã¯
ãããã³ãŒã³æº¶æ¶²äžã§æž¬å®ããéå
ç²åºŠã0.8以
äžã§ããå
±éåäœãããã³è©²å
±éåäœã«å¯Ÿããå
ç¡«çšè¬å€ãå«ãããšãç¹åŸŽãšããèæ²¹æ§ãŽã çµæ
ç©ã§ããã
ïŒäœããïŒïŒåŒäžïŒ²ã¯ççŽ æ°ïŒãïŒã®é£œåã¢
ã«ãã«åºãè¡šããïŒã
ïŒäœããïŒïŒåŒäžïŒ¹ã¯ã¢ãªã«ãªãã·åºãã¢ã¯
ãªããã·åºãã¡ã¿ã¯ãªããã·åºåã¯ãœã«ããã·åº
ãè¡šããïŒã
ïŒäœããïŒïŒåŒäžïŒžã¯å¡©çŽ ååãèçŽ ååå
ã¯ã¯ããã¢ã»ããã·åºãè¡šããïŒã
æ¬çºæã®å
±éåäœã«ãããŠãäžèšåŒïŒïŒã§è¡š
ããããæ§é åäœã圢æããã¢ãããŒã¯äžèšäžè¬
åŒ
ïŒäœããã¯ççŽ æ°ïŒãïŒã®é£œåã¢ã«ãã«åºã
è¡šããïŒ
ã§è¡šãããã飜åèèªæã«ã«ãã³é
žã®ã°ãªã·ãžã«
ãšã¹ãã«ã§ãããå
·äœçã«ã¯ãã°ãªã·ãžã«ã¢ã»ã
ãŒããã°ãªã·ãžã«ããããªããŒããã°ãªã·ãžã«ã
ãã¬ãŒãçã®ïŒçš®ãŸãã¯ïŒçš®ä»¥äžã§ããç¹ã«ã°ãª
ã·ãžã«ã¢ã»ããŒããã°ãªã·ãžã«ããããªããŒãã
奜ãŸããã
æ¬çºæã®å
±éåäœã«ãããŠãäžèšåŒïŒïŒã§è¡š
ããããæ§é åäœã圢æããã¢ãããŒã¯ãäžèšäž
è¬åŒ
ïŒäœããã¯ã¢ãªã«ãªãã·åºãã¢ã¯ãªããã·
åºãã¡ã¿ã¯ãªããã·åºãåã¯ãœã«ããã·åºãè¡šã
ãïŒ
ã§è¡šãããããšãã¬ã³æ§äžé£œååºå«æãšããã·ã
ã§ãããå
·äœçã«ã¯ãã¢ãªã«ã°ãªã·ãžã«ãšãŒã
ã«ãã¢ã¯ãªã«é
žã°ãªã·ãžã«ãã¡ã¿ã¯ãªã«é
žã°ãªã·
ãžã«åã³ãœã«ãã³é
žã°ãªã·ãžã«ããéžã°ããã
æ¬çºæã®å
±éåäœã«ãããŠãäžèšåŒïŒïŒã§è¡š
ããããæ§é åäœã圢æããã¢ãããŒã¯ãäžèšäž
è¬åŒ
ïŒäœããã¯å¡©çŽ ååãèçŽ åååã¯ã¯ããã¢
ã»ããã·åºãè¡šããïŒ
ã§è¡šããããããã²ã³å«æãšããã·ãã§ãããå
·
äœçã«ã¯ããšãã¯ãã«ãããªã³ããšãããã ãã
ãªã³åã³ã¢ãã¯ãã«é
¢é
žã°ãªã·ãžã«ããéžã°ã
ãã
æ¬çºæã«ãããŠäœ¿çšãããåçš®å
±éåäœã®å
·äœ
äŸã瀺ããšäžèšã®åŠãã§ããã
ã°ãªã·ãžã«ã¢ã»ããŒãâã¢ãªã«ã°ãªã·ãžã«ãšãŒ
ãã«å
±éåäœ
ã°ãªã·ãžã«ããããªããŒãâã¢ãªã«ã°ãªã·ãžã«
ãšãŒãã«å
±éåäœ
ã°ãªã·ãžã«ããã¬ãŒãâã¢ãªã«ã°ãªã·ãžã«ãšãŒ
ãã«å
±éåäœ
ã°ãªã·ãžã«ã¢ã»ããŒãâã¢ã¯ãªã«é
žã°ãªã·ãžã«
å
±éåäœ
ã°ãªã·ãžã«ã¢ã»ããŒãâã¡ã¿ã¯ãªã«é
žã°ãªã·ãž
ã«å
±éåäœ
ã°ãªã·ãžã«ã¢ã»ããŒãâã¢ãã¯ãã«é
žã°ãªã·ãž
ã«å
±éåäœ
ã°ãªã·ãžã«ã¢ã»ããŒãâãšããããããªã³å
±é
åäœ
ã°ãªã·ãžã«ããããªããŒãâãšããããããªã³
å
±éåäœ
ã°ãªã·ãžã«ããã¬ãŒãâãšããããããªã³å
±é
åäœ
ã°ãªã·ãžã«ã¢ã»ããŒãâãšããããããªã³âã¢
ãªã«ã°ãªã·ãžã«ãšãŒãã«å
±éåäœ
ã°ãªã·ãžã«ã¢ã»ããŒãâãšããããããªã³âã¢
ã¯ãªã«é
žã°ãªã·ãžã«å
±éåäœ
ã°ãªã·ãžã«ã¢ã»ããŒãâãšããããããªã³âã¡
ã¿ã¯ãªã«é
žã°ãªã·ãžã«å
±éåäœ
ã°ãªã·ãžã«ã¢ã»ããŒãâãšããããããªã³âãœ
ã«ãã³é
žã°ãªã·ãžã«å
±éåäœ
ã°ãªã·ãžã«ã¢ã»ããŒãâã°ãªã·ãžã«ããããªã
ãŒãâã¢ãªã«ã°ãªã·ãžã«ãšãŒãã«å
±éåäœ
ã°ãªã·ãžã«ã¢ã»ããŒãâã°ãªã·ãžã«ããããªã
ãŒãâã¢ã¯ãªã«é
žã°ãªã·ãžã«å
±éåäœ
ã°ãªã·ãžã«ã¢ã»ããŒãâã°ãªã·ãžã«ããããªã
ãŒãâã¡ã¿ã¯ãªã«é
žã°ãªã·ãžã«å
±éåäœ
ã°ãªã·ãžã«ã¢ã»ããŒãâã°ãªã·ãžã«ããããªã
ãŒãâãœã«ãã³é
žã°ãªã·ãžã«å
±éåäœ
ã°ãªã·ãžã«ã¢ã»ããŒãâã°ãªã·ãžã«ããããªã
ãŒãâã¢ãã¯ãã«é
žã°ãªã·ãžã«å
±éåäœ
ã°ãªã·ãžã«ã¢ã»ããŒãâã°ãªã·ãžã«ããããªã
ãŒãâãšããããããªã³å
±éåäœ
ïŒäžèšã«ãããŠãšããããããªã³ã¯ãšãã¯ãã«
ãããªã³ããã³ïŒãŸãã¯ãšãããã ãããªã³ãè¡š
ããïŒã
ãããå
±éåäœã®ã³ã¢ãããŒæåãšããŠã«ã«ã
ã³é
žã°ãªã·ãžã«ãšã¹ãã«ã¯å°ããšã10ã¢ã«ïŒ
以äž
å«ããã®ã䜿çšããããäžèšæåã10ã¢ã«ïŒ
æªæº
ã§ãããšå ç¡«ãŽã ã®èæ²¹æ§ãäœäžããã®ã§å¥œãŸã
ããªãããŸãå ç¡«çšå®èœåºãšãªããšãã¬ã³æ§äžé£œ
ååºãæãããšããã·ããŸãã¯ããã²ã³å«æãšã
ãã·ãã¯å°ããšãïŒã¢ã«ïŒ
以äžå«ãŸããããšãå¿
èŠã§ããã
ããšãã°ã«ã«ãã³é
žã°ãªã·ãžã«ãšã¹ãã«âã¢ãª
ã«ã°ãªã·ãžã«ãšãŒãã«å
±éåäœã«ãããŠã¯åè
ã
80ã99ã¢ã«ïŒ
ãåŸè
ã20ãïŒã¢ã«ïŒ
ã®ç¯å²ã奜ãŸ
ãããã«ã«ãã³é
žã°ãªã·ãžã«ãšã¹ãã«âãšããã
ãããªã³å
±éåäœã«ãããŠã¯åè
ã20ã95ã¢ã«
ïŒ
ãåŸè
ãïŒã80ã¢ã«ïŒ
ã®ç¯å²ã奜ãŸããã
ãããã®å
±éåç©ã¯æ¬åºé¡äººã®åºé¡ã«ãããã
ç±³åœç¹èš±ç¬¬3773694å·ã«é瀺ãããïœïŒææ©é«å
åç©ããã³ïœïŒæ£ãªã³é
žãããã¯ããªãªã³é
žé¡ã®
ã¢ã«ãã«ãšã¹ãã«ã®ç±çž®åçæç©ã觊åªãšããŠå
ã¢ãããŒæåãéç°å
±éåããããšã«ããåŸãã
ããéååå¿ã¯æº¶åªã®ååšäžãããã¯äžååšäžã«
ãããŠéåžž10ã80âã®æž©åºŠç¯å²ã§è¡ããã觊åªã¯
ã¢ãããŒ100ïœã«å¯Ÿã0.01ã1.0ïœã®ç¯å²ãé©åœã§
ãããåå¿ç³»äžã®æ°Žåã¯å¯èœãªéãäœãããããš
ãæãŸããããã®ããã«ããŠåŸãããå
±éåäœã¯
80âã0.1ïŒ
ã®ã¢ãã¯ãããã³ãŒã³æº¶æ¶²äžã§æž¬å®
ããéå
ç²åºŠã0.8以äžã§ãããŽã ç¶ã®ã©ã³ãã
å
±éåäœã§ããã
æ¬çºæçµæç©ã¯ããªããŒæåãšããŠäžèšå
±éå
äœä»¥å€ã®ããªããŒãå«ãããšãã§ããããããã®
ããªããŒã¯ç¹ã«å¶éã¯ãªããäžèšå
±éåäœãšå
±é
ããå ç¡«ç³»ã§å ç¡«ããããã®ã奜ãŸããã
ããšãã°ã¢ãªã«ã°ãªã·ãžã«ãšãŒãã«ãããã¯ã¢
ã¯ãªã«é
žã°ãªã·ãžã«ãã¡ã¿ã¯ãªã«é
žã°ãªã·ãžã«ã®
ããšããšãã¬ã³æ§äžé£œååºãæããã¢ãããŒãšã®
å
±éåäœã«å¯ŸããŠå¥œãŸããããªããŒãšããŠã¯ã倩
ç¶ãŽã ãã€ãœãã¬ã³ãŽã ããã¿ãžãšã³ãŽã ãã¹ã
ã¬ã³âãã¿ãžãšã³ãŽã ããšãã¬ã³âãããã¬ã³â
ãã¿ãžãšã³ãŽã ãããã«ãŽã ãããã²ã³åããã«
ãŽã ãã¯ãããã¬ã³ãŽã ãã¢ã¯ãªã«ãããªã«âã
ã¿ãžãšã³ãŽã ããšãã¯ãã«ãããªã³âã¢ãªã«ã°ãª
ã·ãžã«ãšãŒãã«å
±éåäœãŽã ããšãã¯ãã«ãããª
ã³âãšãã¬ã³ãªããµã€ãâã¢ãªã«ã°ãªã·ãžã«ãšãŒ
ãã«å
±éåäœãŽã ãäžé£œååºå«æã¢ã¯ãªã«ãŽã ç
ãæããããšãã§ããã
ãŸããšããããããªã³ãã¢ãã¯ãã«é
¢é
žã°ãªã·
ãžã«ã®ããšãããã²ã³å«æã¢ãããŒãšã®å
±éåäœ
ã«å¯ŸããŠå¥œãŸããããªããŒãšããŠã¯ããšãã¯ãã«
ãããªã³åç¬éåäœãŽã ããšãã¯ãã«ãããªã³â
ã¢ãªã«ã°ãªã·ãžã«ãšãŒãã«å
±éåäœãŽã ããšãã¯
ãã«ãããªã³âãšãã¬ã³ãªãã·ãå
±éåäœãŽã ã
ãšãã¯ãã«ãããªã³âãšãã¬ã³ãªãã·ãâã¢ãªã«
ã°ãªã·ãžã«ãšãŒãã«å
±éåäœãŽã ãã¯ãããã¬ã³
ãŽã ãå¡©çŽ å«æã¢ã¯ãªã«ãŽã ãå¡©çŽ åããªãšãã¬
ã³ãŽã ãã¯ãã«ã¹ã«ãã³åããªãšãã¬ã³ãŽã ãåŒ
åãŽã ãèçŽ åããã«ãŽã çãæããããšãã§ã
ãã
ãããã®ããªããŒçµæãæããæ¬çºæçµæç©ã«
ãããŠäœ¿çšãããå ç¡«å€ã¯ãå
±éåäœã®ã³ã¢ãã
ãŒæåããšãã¬ã³æ§äžé£œåãšããã·ãã§ããå Žå
ã¯å
¬ç¥ã®äžé£œåãŽã ã®å ç¡«å€ãçšããããšãã§ã
ãã
ãã®ãããªå ç¡«å€ã®äŸãšããŠææ©ãã«ãªãã·
ããç¡«é»ãç¡«é»äŸäžæ§ååç©ãç¡«é»ååç©ç³»ä¿é²
å€ããããã¯ããããšåçš®ä¿é²å€ã®çµåããã¡ã«
ã«ããããªã¢ãžã³é¡çã®ã»ãããããæš¹èå ç¡«çš
è¬å€ããããããªãã·ã å ç¡«çšè¬å€çãæããã
ããææ©ãã«ãªãã·ããšããŠã¯ãžã¯ãã«ãã«ãªã
ã·ããããŠã¡ã³ãã€ãããã«ãªãã·ããïŒïŒïŒâ
ãžã¡ãã«âïŒïŒïŒâãžâïŒç¬¬äžããã«ãã«ãªã
ã·ïŒãããµã³ããžç¬¬äžããã«ãã«ãªãã·ãããã³
ãŸã€ã«ãã«ãªãã·ãçãæãããããç¡«é»äŸäžå
åç©ã®äŸãšããŠã¯ãããã©ã¡ãã«ããŠã©ã ãžã¹ã«
ãã€ãããã³ã¿ã¡ãã¬ã³ããã©ã¹ã«ãã€ããç¡«é»
ååç©ä¿é²å€ã®äŸãšããŠã¯ïŒâã¡ã«ã«ãããã³ãŸ
ãã¢ãŸãŒã«ããžãã³ãŸãã¢ãŸãŒã«çã®ãã¢ãŸãŒã«
é¡ãïŒâã·ã¯ãããã·ã«ãã³ãŸãã¢ãžã«ã¹ã«ããš
ã³ã¢ããã®ããšãã¡ã«ã«ããã€ãããŸãªã³é¡ããž
ã¡ãã«ããªã«ã«ããã³é
žã®ããšãããªã«ã«ããã³
é
žå¡©é¡ãã€ãœãããã«ããµã³ãã²ã³é
žäºéã®ããš
ãããµã³ãã²ã³é
žå¡©é¡çãæããããããŸãç¡«é»
ãããã¯ç¡«é»ç³»ååç©ãšçµåãããŠäœ¿çšããä¿é²
å€ã®äŸãšããŠã¯ãžããšãã«ã°ã¢ããžã³ã®ããšãã°
ã¢ããžã³é¡ããããµã¡ãã¬ã³ããã©ãã³ã®ããšã
ã¢ãã³é¡çãããããŸãã¡ã«ã«ããããªã¢ãžã³é¡
ã®äŸãšããŠã¯ãããšãã°ãžããã«ã¢ããâïŒïŒïŒ
âãžã¡ã«ã«ããããªã¢ãžã³ãæããããšãã§ã
ããæš¹èå ç¡«çšè¬å€ãšããŠã¯ã¢ã«ãã«ããšããŒã«
ãã«ã ã¢ã«ãããæš¹èé¡ããªãã·ã å ç¡«çšè¬å€ãš
ããŠã¯ïœâããã³ãžãªãã·ã ãppâ²âãžãã³ãžã«
ããã³ãžãªãã·ã çãæããããšãã§ããã
ãŸãæ¬çºæçµæç©ã«ãããå
±éåäœã®ã³ã¢ãã
ãŒæåãããã²ã³å«æãšããã·ãã§ããå Žåã®å
ç¡«å€ãšããŠã¯ããªã¢ãã³é¡ãããªãŠã¬ã¢é¡ãã¡ã«
ã«ããããªã¢ãžã³é¡ãããªããšããŒã«é¡çãæã
ããããããªã¢ãã³é¡å ç¡«å€ã®å
·äœäŸãšããŠã¯ã
ããµã¡ãã¬ã³ãžã¢ãã³ã«ãŒãã¡ãŒããããªãŠã¬ã¢
é¡ã®å
·äœäŸãšããŠã¯ãšãã¬ã³ããªãŠã¬ã¢ããžãã
ã«ããªãŠã¬ã¢ããŸãã¡ã«ã«ããããªã¢ãžã³é¡ã®å
·
äœäŸãšããŠã¯ããªã¡ã«ã«ããããªã¢ãžã³ããžãã
ã«ã¢ããâïŒïŒïŒâããªã¢ãžã³çãæããããã
äžèšã®ããšãå®èœåºãæããªããŽã é¡ããšãã°
ãšãã¬ã³âãããã¬ã³ãŽã ãã·ãªã³ã³ãŽã çãæ··
åããå Žåã¯ããšãã°ææ©ãã«ãªãã·ãã«ããå
ç¡«æ³ãæ¡çšããŠé©åã«ãã¬ã³ãããããšãã§ã
ãã
ãããã®å ç¡«å€ã¯åœè©²åéã®æ¢ç¥ã®æè¡ã«åŸã€
ãŠé©å®å ç¡«å©å€ãšçµåãããŠäœ¿çšããããæ¬çºæ
çµæç©ã«é
åããããããå ç¡«å€ãå ç¡«å©å€ã¯ã
ãªããŒæåã«å¯ŸããŠ0.01ã20ééïŒ
ãéåžž0.1ã
15ééïŒ
ã®ç¯å²ã§äœ¿çšãããããããã®éã®ããª
ããŒã®çµæãè¬å€ã®çš®é¡ãæååã®ç®ççã«ãã€
ãŠä»»æã«å®ããããã
ããã«æ¬çºæçµæç©ã¯å å·¥äžå¿
èŠãªãããã¯å®
çšäžã®è«žç©æ§ã®èª¿æŽã«å¿
èŠãªåçš®ã®è£åŒ·å€ãå
å¡«
å€ãå¯å¡å€ãå å·¥å©å€ãå®å®å€ãèåé²æ¢å€ãé¡
æãé£çå€çãä»»æã«é
åã§ããããŸãæ¬çºæçµ
æç©ã®è£œé å å·¥ã«ãããŠãåœè©²æè¡åéã§è¡ãã
ãŠããåçš®ã®å å·¥æ段ãå©çšã§ããã
æ¬çºæçµæç©ã¯ä»¥äžè¿°ã¹ãããã«éåžžã®å ç¡«å€
ã«ãã容æã«å ç¡«ããããšãšãã«ãåŸãããå ç¡«
ç©ã¯æ¬¡ã®ãããªç¹è²ãæããã
åçš®ãªã€ã«é¡ã«å¯ŸããããããŠè¯å¥œãªèæ²¹æ§
ãæãããšãšãã«èå¯æ§ãèç±æ§ãå
ŒåããŽã
ãšããŠã®æ§èœãã©ã³ã¹ãåªããŠããã
é
žææ²¹ã«å¯ŸããŠãåªããèæ§ãæããã
åŸæ¥ã®ããã²ã³å«æãŽã ã«æ¯èŒãéå±ã«å¯Ÿã
ãè
èæ§ãæ¹åãããã
åŒçŽ ãŽã ã«æ¯èŒããŠå¯Ÿæœ€æ»æ²¹æ§ãèãšã³ãžã³
ãªã€ã«æ§ã¯å¹æµããããã«èå¯æ§ãèããæ¹å
ããããã€çµæžçã«å®äŸ¡ãªå©ç¹ãæããã
以äžå®æœäŸãæ¯èŒäŸã«ããæ¬çºæçµæç©ã®å¹æ
ã説æããããªãè¡šäžã®é
åã¯éééšã§ããã
å®æœäŸïŒã14ãæ¯èŒäŸïŒãïŒ
第ïŒè¡šã«ç€ºãåé
åç©ãããŒã«æž©åºŠ60âã®ïŒã€
ã³ãããŒã«ã§æ··ç·Žãè¡ãã160âã§20åéå å§æ
åããåŸãããå ç¡«ç©ã®ç©æ§è©Šéšãè¡ã€ãããã®
çµæã第ïŒè¡šã«ç€ºãã
The present invention relates to a novel oil-resistant rubber composition. Acrylic nitrile is a typical oil-resistant rubber.
There are butadiene copolymer rubbers, epichlorohydrin rubbers, acrylic rubbers, etc., and they are used depending on the usage environment. However, in recent years, various problems have arisen as the components of fuel oil and lubricating oil have changed. For example, the aromatic hydrocarbon content of fuel oil is increasing, and the types and amounts of various additives are increasing in lubricating oil.
It has become necessary to improve the resistance of rubbers that come into contact with or be immersed in these materials as much as possible so as not to cause deterioration in physical properties or deterioration due to the effects of additives. On the other hand, deterioration caused by oil degraded by oxidation in the air, so-called rancid oil, is also a major problem for oil-resistant rubber products. As a countermeasure for this type of problem, fluororubber is often used as a substitute due to its excellent performance, but this rubber has the drawbacks of being very expensive and having significantly poor cold resistance. Generally speaking, as oil resistance improves, cold resistance of rubber decreases, and epichlorohydrin-ethylene oxide copolymer rubbers are known as rubbers that have both high oil resistance and cold resistance. Rubber is susceptible to deterioration due to various additives in the oil or rancid oil. As described above, due to its molecular structure, epichlorohydrin rubber is susceptible to the effects of lubricating oil additives due to oxidative decomposition (oxidative deterioration) of the polyether main chain and the presence of chlorine, and the possibility of corrosion to metals poses a problem. In addition, nitrile rubber has poor ozone resistance due to the presence of unsaturated bonds and is susceptible to embrittlement during aging. Furthermore, the balance between oil resistance and cold resistance is poor. Furthermore, although acrylic rubber has excellent lubricating oil resistance, it has extremely poor resistance to fuel oil and very poor cold resistance. Under these circumstances, there is a desire for an inexpensive rubber that has both high oil resistance and cold resistance, and has improved resistance to the above-mentioned additives, rancid oil, and the like. The present inventors have arrived at the present invention as a result of intensive research to satisfy these conditions, that is, the main chain structure of the present invention is composed of 10 mol% or more of structural units represented by the following formula () and the formula (). A copolymer consisting of 1 mol% or more of the structural unit represented by and/or the structural unit represented by the formula () and having a reduced viscosity of 0.8 or more when measured in a 0.1% monochlorobenzene solution at 80°C, and An oil-resistant rubber composition characterized by containing a vulcanizing agent for a copolymer. (However, in the formula (), R represents a saturated alkyl group having 1 to 4 carbon atoms). (However, in the formula (), Y represents an allyloxy group, an acryloxy group, a methacryloxy group, or a sorboxy group). (However, in the formula (), X represents a chlorine atom, a bromine atom, or a chloroacetoxy group). In the copolymer of the present invention, the monomer forming the structural unit represented by the above formula () has the following general formula: (However, R represents a saturated alkyl group having 1 to 4 carbon atoms.) It is a glycidyl ester of a saturated aliphatic carboxylic acid represented by One species or two or more species are particularly preferred, and glycidyl acetate and glycidyl propionate are particularly preferred. In the copolymer of the present invention, the monomer forming the structural unit represented by the above formula () has the following general formula: (However, Y represents an allyloxy group, an acryloxy group, a methacryloxy group, or a sorboxy group.) It is an ethylenically unsaturated group-containing epoxide represented by: Selected from glycidyl sorbate. In the copolymer of the present invention, the monomer forming the structural unit represented by the above formula () has the following general formula: (However, X represents a chlorine atom, a bromine atom, or a chloroacetoxy group.) It is a halogen-containing epoxide represented by the following formula, and is specifically selected from epichlorohydrin, epibromohydrin, and glycidyl monochloroacetate. Specific examples of various copolymers used in the present invention are as follows. Glycidyl acetate-allyl glycidyl ether copolymer Glycidyl propionate-allyl glycidyl ether copolymer Glycidyl butyrate-allyl glycidyl ether copolymer Glycidyl acetate-glycidyl acrylate copolymer Glycidyl acetate-glycidyl methacrylate copolymer Glycidyl acetate -Glycidyl monochlorate copolymer Glycidyl acetate-epihalohydrin copolymer Glycidyl propionate-epihalohydrin copolymer Glycidyl butyrate-epihalohydrin copolymer Glycidyl acetate-epihalohydrin-allyl glycidyl ether copolymer Glycidyl acetate-epihalohydrin-glycidyl acrylate Copolymer Glycidyl acetate-epihalohydrin-glycidyl methacrylate copolymer Glycidyl acetate-epihalohydrin-glycidyl sorbate copolymer Glycidyl acetate-glycidyl propionate-allyl glycidyl ether copolymer Glycidyl acetate-glycidyl propionate-glycidyl acrylate Copolymer Glycidyl acetate-glycidyl propionate-glycidyl methacrylate copolymer Glycidyl acetate-glycidyl propionate-glycidyl sorbate copolymer Glycidyl acetate-glycidyl propionate-glycidyl monochlorate copolymer Glycidyl acetate-glycidyl methacrylate copolymer Pionate-epihalohydrin copolymer (in the above epihalohydrin represents epichlorohydrin and/or epibromohydrin). These copolymers contain at least 10 mol% or more of carboxylic acid glycidyl ester as a comonomer component. If the content of the above components is less than 10 mol%, the oil resistance of the vulcanized rubber decreases, which is not preferable. Further, it is necessary that at least 1 mol % or more of an epoxide having an ethylenically unsaturated group or a halogen-containing epoxide serving as a vulcanizing functional group is contained. For example, in carboxylic acid glycidyl ester-allyl glycidyl ether copolymer, the former is
The latter is preferably in the range of 80 to 99 mol%, and the latter in the range of 20 to 1 mol%. In the carboxylic acid glycidyl ester-epihalohydrin copolymer, the former is preferably in the range of 20 to 95 mol%, and the latter is in the range of 5 to 80 mol%. These copolymers are prepared using a thermal condensation product of a) an organotin compound and b) an alkyl ester of orthophosphoric acid or polyphosphoric acids as a catalyst, which is disclosed in U.S. Pat. No. 3,773,694 filed by the present applicant. It can be obtained by ring-opening copolymerization. The polymerization reaction is usually carried out at a temperature range of 10 to 80°C in the presence or absence of a solvent, the appropriate amount of catalyst is 0.01 to 1.0 g per 100 g of monomer, and the moisture in the reaction system is kept as low as possible. It is desirable to keep it low. The copolymer thus obtained is
It is a rubbery random copolymer with a reduced viscosity of 0.8 or more when measured in a 0.1% monochlorobenzene solution at 80°C. The composition of the present invention can contain polymers other than the above copolymers as polymer components. There are no particular restrictions on these polymers, but those that can be vulcanized using the same vulcanization system as the above-mentioned copolymers are preferred. For example, preferred polymers for copolymers with monomers having ethylenically unsaturated groups such as allyl glycidyl ether, glycidyl acrylate, and glycidyl methacrylate include natural rubber, isoprene rubber, butadiene rubber, styrene-butadiene rubber, and ethylene rubber. -propylene-
Examples include butadiene rubber, butyl rubber, halogenated butyl rubber, chloroprene rubber, acrylonitrile-butadiene rubber, epichlorohydrin-allyl glycidyl ether copolymer rubber, epichlorohydrin-ethylene oxide-allyl glycidyl ether copolymer rubber, unsaturated group-containing acrylic rubber, etc. be able to. Preferred polymers for copolymers with halogen-containing monomers such as epihalohydrin and glycidyl monochloroacetate include epichlorohydrin homopolymer rubber, epichlorohydrin-
Allyl glycidyl ether copolymer rubber, epichlorohydrin-ethylene oxide copolymer rubber,
Examples include epichlorohydrin-ethylene oxide-allyl glycidyl ether copolymer rubber, chloroprene rubber, chlorine-containing acrylic rubber, chlorinated polyethylene rubber, chlorosulfonated polyethylene rubber, fluorinated rubber, and brominated butyl rubber. As the vulcanizing agent used in the composition of the present invention having these polymer compositions, when the comonomer component of the copolymer is an ethylenically unsaturated epoxide, a known vulcanizing agent for unsaturated rubber can be used. Examples of such vulcanizing agents include organic peroxides, sulfur, sulfur donating compounds, sulfur compound accelerators, combinations of these and various accelerators, mercaptotriazines, so-called resin vulcanizing agents, and oxime vulcanizing agents. Examples include sulfur chemicals. Examples of organic peroxides include dicumyl peroxide, kyumene hydroperoxide, 2,5-
Examples include dimethyl-2,5-di-(tert-butylperoxy)hexane, di-tert-butyl peroxide, benzoyl peroxide, and the like. Examples of sulfur donor compounds include tetramethylthiuram disulfide and pentamethylene tetrasulfide. Examples of sulfur compound promoters include thiazoles such as 2-mercaptobenzothiazole and dibenzothiazole, and 2-cyclohexylbenzothiazyl sulfide. Examples include mercaptoimidazolines such as phenamide, thiocarbamates such as dimethylthiocarbamic acid, and xanthates such as zinc isopropylxanthate. Examples of accelerators used in combination with sulfur or sulfur-based compounds include guanidines such as diphenylguanidine and amines such as hexamethylenetetramine. Examples of mercaptotriazines include dibutylamino-3,5
- Dimercaptotriazine may be mentioned. Examples of resin vulcanizing agents include alkylphenol formaldehyde resins, and oxime vulcanizing agents include p-quinone dioxime and pp'-dibenzylquinone dioxime. Further, when the comonomer component of the copolymer in the composition of the present invention is a halogen-containing epoxide, examples of the vulcanizing agent include polyamines, thioureas, mercaptotriazines, polyphenols, and the like. Specific examples of polyamine vulcanizing agents include hexamethylene diamine carbamate, specific examples of thioureas include ethylene thiourea, dibutylthiourea, and specific examples of mercaptotriazines include trimercaptotriazine, dibutylamino-3,5-triazine, etc. can be mentioned. When mixing rubbers that do not have the above-mentioned functional groups, such as ethylene-propylene rubber, silicone rubber, etc., a vulcanization method using an organic peroxide can be employed for appropriate blending. These vulcanizing agents are used in combination with vulcanization aids as appropriate according to known techniques in the art. These vulcanizing agents and vulcanization aids blended into the composition of the present invention are 0.01 to 20% by weight, usually 0.1 to 20% by weight, based on the polymer components.
Used in a range of 15% by weight. These amounts are arbitrarily determined depending on the composition of the polymer, the type of drug, the purpose of the molded product, etc. Furthermore, the composition of the present invention may optionally contain various reinforcing agents, fillers, plasticizers, processing aids, stabilizers, anti-aging agents, pigments, flame retardants, etc. necessary for processing or for adjusting various physical properties in practical use. Can be combined with Furthermore, various processing methods used in the technical field can be used in the production and processing of the composition of the present invention. As described above, the composition of the present invention can be easily vulcanized using a common vulcanizing agent, and the resulting vulcanizate has the following characteristics. It has extremely good oil resistance against various oils, as well as cold and heat resistance, giving it an excellent balance of performance as a rubber. It also has excellent resistance to rancid oils. Corrosion to metals is improved compared to conventional halogen-containing rubbers. Compared to fluororubber, it has comparable lubricating oil resistance and engine oil resistance, has significantly improved cold resistance, and is economically inexpensive. The effects of the composition of the present invention will be explained below using Examples and Comparative Examples. The formulations in the table are parts by weight. Examples 1 to 14, Comparative Examples 1 to 6 Each compound shown in Table 1 was kneaded with a 6-inch roll at a roll temperature of 60°C, and then pressure-molded at 160°C for 20 minutes. Physical property tests were conducted. The results are shown in Table 2.
ãè¡šããtableã
ãè¡šããtableã
ãè¡šããtableã
ãè¡šããtableã
ãè¡šã
以äžã®è©Šéšçµæããæ¬çºæå ç¡«çµæç©ã¯NBR
ïŒæ¯èŒäŸïŒïŒããšãã¯ãã«ãããªã³âãšãã¬ã³ãªã
ã·ãâã¢ãªã«ã°ãªã·ãžã«ãšãŒãã«å
±éåäœãŽã
ïŒæ¯èŒäŸïŒïŒããšãã¯ãã«ãããªã³âãšãã¬ã³ãªã
ã·ãå
±éåäœãŽã ïŒæ¯èŒäŸïŒïŒããšãã¯ãã«ãã
ãªã³ãŽã ïŒæ¯èŒäŸïŒïŒãã¢ã¯ãªã«ãŽã ïŒæ¯èŒäŸïŒïŒ
ã«æ¯èŒãèæ²¹æ§ã«åªããŠãããèå¯æ§ãèç±æ§ãš
ã®ãã©ã³ã¹ã®è¯ãããšãå€ããããçŽ ãŽã ïŒæ¯èŒ
äŸïŒïŒã¯ä»ã®è«žæ§è³ªã¯åªããŠãããèå¯æ§ãå£ã€
ãŠããããŸãå®æœäŸïŒïŒïŒãšæ¯èŒäŸïŒïŒïŒãšã®å¯Ÿ
ç
§ã«ããæ¬çºæåããããªã«ãŽã ããšãã¯ãã«ã
ããªã³ç³»ãŽã ã«æ··åãããšããããã®èæ²¹æ§ãæ¹
åãããããšãå€ãã
è
é£è©Šéš
å®æœäŸïŒïŒïŒã11ãæ¯èŒäŸïŒïŒïŒã®åå ç¡«ç©ã
ïŒæã®éå±æ¿ã«æŸã¿ãçžå¯Ÿæ¹¿åºŠ100ïŒ
ã50âã®é°
å²æ°ã§120æéé眮åŸãåãåºãããŽã çè·¡ã®é
å±æ¿ã®è
é£åºŠãäžèšã®ãããªã¯ã©ã¹ã§è©äŸ¡ããã
ãã®çµæã第ïŒè¡šã«ç€ºããäœãéŒæ¿ã¯JIS G314
ïŒSPCCïŒãã¢ã«ãæ¿ã¯JIS H4000ïŒA505 2pïŒã䜿
çšããã[Table] From the above test results, the vulcanized composition of the present invention is NBR
(Comparative example 1), epichlorohydrin-ethylene oxide-allyl glycidyl ether copolymer rubber (comparative example 2), epichlorohydrin-ethylene oxide copolymer rubber (comparative example 3), epichlorohydrin rubber (comparative example 4), acrylic rubber (comparative example 5) )
It has superior oil resistance compared to , and it can be seen that it has a good balance between cold resistance and heat resistance. Fluororubber (Comparative Example 6) is excellent in other properties, but poor in cold resistance. Further, a comparison between Examples 6 and 7 and Comparative Examples 1 and 2 shows that when the products of the present invention are mixed with nitrile rubber or epichlorohydrin rubber, the oil resistance of these rubbers is improved. Corrosion test Each of the vulcanizates of Examples 1, 8 to 11 and Comparative Examples 3 and 4 was sandwiched between two metal plates and left to stand in an atmosphere of 100% relative humidity and 50°C for 120 hours, then taken out and rubber pieces The degree of corrosion of the metal plate left behind was evaluated using the following classes.
The results are shown in Table 3. However, the steel plate is JIS G314
(SPCC), and the aluminum plate used was JIS H4000 (A505 2p).
ãè¡šããtableã
ãè¡šã
æ¬çºæå ç¡«çµæç©ã¯ãšãã¯ãã«ãããªã³ç³»ãŽã
ã«æ¯ã¹ãŠèéå±è
èæ§ãèããæ¹åãããŠããã[Table] The vulcanized composition of the present invention has significantly improved metal corrosion resistance compared to epichlorohydrin rubber.
Claims (1)
åäœ10ã¢ã«ïŒ 以äžãšåŒïŒïŒã§è¡šããããæ§é å
äœããã³ïŒãããã¯åŒïŒïŒã§è¡šããããæ§é å
äœïŒã¢ã«ïŒ 以äžãšãããªãã80âïŒ0.1ïŒ ã®ã¢ã
ã¯ãããã³ãŒã³æº¶æ¶²äžã§æž¬å®ããéå ç²åºŠã0.8
以äžã§ããå ±éåäœãããã³è©²å ±éåäœã«å¯Ÿãã
å ç¡«çšè¬å€ãå«ãããšãç¹åŸŽãšããèæ²¹æ§ãŽã çµ
æç©ã ïŒäœããïŒïŒåŒäžïŒ²ã¯ççŽ æ°ïŒãïŒã®é£œåã¢
ã«ãã«åºãè¡šããïŒã ïŒäœããïŒïŒåŒäžïŒ¹ã¯ã¢ãªã«ãªãã·åºãã¢ã¯
ãªããã·åºãã¡ã¿ã¯ãªããã·åºåã¯ãœã«ããã·åº
ãè¡šããïŒã ïŒäœããïŒïŒåŒäžïŒžã¯å¡©çŽ ååãèçŽ ååå
ã¯ã¯ããã¢ã»ããã·åºãè¡šããïŒã[Scope of Claims] 1 The main chain structure includes 10 mol% or more of the structural units represented by the following formula (), and 1 mol% or more of the structural units represented by the formula () and/or the structural units represented by the formula (). The reduced viscosity measured in 0.1% monochlorobenzene solution at 80â is 0.8.
An oil-resistant rubber composition comprising the copolymer described above and a vulcanizing agent for the copolymer. (However, in the formula (), R represents a saturated alkyl group having 1 to 4 carbon atoms). (However, in the formula (), Y represents an allyloxy group, an acryloxy group, a methacryloxy group, or a sorboxy group). (However, in the formula (), X represents a chlorine atom, a bromine atom, or a chloroacetoxy group).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP13167183A JPS6023412A (en) | 1983-07-18 | 1983-07-18 | Oil-resistant rubber composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP13167183A JPS6023412A (en) | 1983-07-18 | 1983-07-18 | Oil-resistant rubber composition |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP459388A Division JPS63225627A (en) | 1988-01-11 | 1988-01-11 | Oil-resistant rubber composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS6023412A JPS6023412A (en) | 1985-02-06 |
JPS6333789B2 true JPS6333789B2 (en) | 1988-07-06 |
Family
ID=15063500
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP13167183A Granted JPS6023412A (en) | 1983-07-18 | 1983-07-18 | Oil-resistant rubber composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6023412A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100806105B1 (en) * | 2002-03-07 | 2008-02-21 | 죌ìíì¬ ìì§ìŽììŽ | Apparatus for display |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63317527A (en) * | 1987-06-19 | 1988-12-26 | Osaka Soda Co Ltd | Epoxide copolymer |
JP5608956B2 (en) * | 2007-09-06 | 2014-10-22 | ãã€ãœãŒæ ªåŒäŒç€Ÿ | Polyether based multi-component copolymer and cross-linked product thereof |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5966451A (en) * | 1982-09-15 | 1984-04-14 | ãŒãªã³ãã±ãã«ã«ãºããŠãŒãšã¹ãšãŒïŒã€ã³ã³ãŒãã¬ã€ãã£ã | Epihalohydrine polymer |
-
1983
- 1983-07-18 JP JP13167183A patent/JPS6023412A/en active Granted
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5966451A (en) * | 1982-09-15 | 1984-04-14 | ãŒãªã³ãã±ãã«ã«ãºããŠãŒãšã¹ãšãŒïŒã€ã³ã³ãŒãã¬ã€ãã£ã | Epihalohydrine polymer |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100806105B1 (en) * | 2002-03-07 | 2008-02-21 | 죌ìíì¬ ìì§ìŽììŽ | Apparatus for display |
Also Published As
Publication number | Publication date |
---|---|
JPS6023412A (en) | 1985-02-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4048261A (en) | Vulcanizable compositions of a halogen-containing polymer and a diene-nitrile rubber having active halogen cure sites | |
EP0950078B1 (en) | Perfluoroether-containing fluoroelastomers with good low temperature characteristics | |
JPH08120146A (en) | Fluoroelastomer composition | |
US3026305A (en) | Vulcanization of polymers and copolymers of epichlorohydrin | |
JP2002060550A (en) | Halogen containg rubber composition | |
JP4595940B2 (en) | Ethylene-alkyl acrylate copolymer rubber composition | |
EP2837657B1 (en) | Acrylic rubber composition, and crosslinked product thereof | |
JPS6333789B2 (en) | ||
US4792581A (en) | Rubber composition | |
EP0044683B1 (en) | Blends of oil-resistant elastomers and grafted epdm-terpolymers | |
JPS62116634A (en) | Sulfur curable silicone rubber and its eleastomer blend | |
US20200040157A1 (en) | Nanosubstance-containing composition | |
EP0761749A1 (en) | Heat resistant butadiene/acrylonitrile-polyvinyl chloride blends | |
JPH034583B2 (en) | ||
KR910006035B1 (en) | Process for cross-linking halogenated polymers | |
KR100402518B1 (en) | A chlorosulfonated ethylene-alpha-olefin copolymer composition and a joint boot using the composition | |
JPS59217749A (en) | Fluorine-containing elastomer composition | |
JP4531204B2 (en) | Chloroprene-based rubber composition | |
US4530994A (en) | Rubbery solid polymer or copolymer of glycidyl carboxylate and composition thereof | |
JPS582321A (en) | Cis-1,4-polyisoprene rubber composition giving improved strength by vulcanization | |
JP2622693B2 (en) | Rubber mixture | |
JPH10245451A (en) | Composition of acrylic rubber or its blend rubber | |
JP2891036B2 (en) | Vulcanizable rubber composition | |
JP4285216B2 (en) | Polyether copolymer and cross-linked product thereof | |
JP5233988B2 (en) | Polyether-based multi-component copolymer, cross-linkable rubber composition containing the same, and automotive rubber parts comprising the cross-linked product |