JPH0244331B2 - - Google Patents
Info
- Publication number
- JPH0244331B2 JPH0244331B2 JP58137179A JP13717983A JPH0244331B2 JP H0244331 B2 JPH0244331 B2 JP H0244331B2 JP 58137179 A JP58137179 A JP 58137179A JP 13717983 A JP13717983 A JP 13717983A JP H0244331 B2 JPH0244331 B2 JP H0244331B2
- Authority
- JP
- Japan
- Prior art keywords
- rubber
- peroxide
- pigment
- organic
- present
- 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
- 229920001971 elastomer Polymers 0.000 claims description 34
- 239000005060 rubber Substances 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 20
- 239000000975 dye Substances 0.000 claims description 13
- 150000001451 organic peroxides Chemical class 0.000 claims description 6
- 239000012860 organic pigment Substances 0.000 claims description 6
- 239000001023 inorganic pigment Substances 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 239000003086 colorant Substances 0.000 claims description 4
- 238000010060 peroxide vulcanization Methods 0.000 claims description 4
- 239000000049 pigment Substances 0.000 description 16
- 239000012039 electrophile Substances 0.000 description 6
- 238000004073 vulcanization Methods 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- -1 t-butylperoxy Chemical group 0.000 description 4
- 235000014692 zinc oxide Nutrition 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- 229920002943 EPDM rubber Polymers 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920000181 Ethylene propylene rubber Polymers 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- 229920000459 Nitrile rubber Polymers 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 description 2
- 238000005562 fading Methods 0.000 description 2
- HTUMBQDCCIXGCV-UHFFFAOYSA-N lead oxide Chemical compound [O-2].[Pb+2] HTUMBQDCCIXGCV-UHFFFAOYSA-N 0.000 description 2
- YEXPOXQUZXUXJW-UHFFFAOYSA-N lead(II) oxide Inorganic materials [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229920001084 poly(chloroprene) Polymers 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 150000004053 quinones Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 239000005061 synthetic rubber Substances 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 1
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- HCXVPNKIBYLBIT-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 3,5,5-trimethylhexaneperoxoate Chemical compound CC(C)(C)CC(C)CC(=O)OOOC(C)(C)C HCXVPNKIBYLBIT-UHFFFAOYSA-N 0.000 description 1
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 1
- NLBJAOHLJABDAU-UHFFFAOYSA-N (3-methylbenzoyl) 3-methylbenzenecarboperoxoate Chemical compound CC1=CC=CC(C(=O)OOC(=O)C=2C=C(C)C=CC=2)=C1 NLBJAOHLJABDAU-UHFFFAOYSA-N 0.000 description 1
- RIPYNJLMMFGZSX-UHFFFAOYSA-N (5-benzoylperoxy-2,5-dimethylhexan-2-yl) benzenecarboperoxoate Chemical compound C=1C=CC=CC=1C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C1=CC=CC=C1 RIPYNJLMMFGZSX-UHFFFAOYSA-N 0.000 description 1
- BLKRGXCGFRXRNQ-SNAWJCMRSA-N (z)-3-carbonoperoxoyl-4,4-dimethylpent-2-enoic acid Chemical compound OC(=O)/C=C(C(C)(C)C)\C(=O)OO BLKRGXCGFRXRNQ-SNAWJCMRSA-N 0.000 description 1
- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 description 1
- HSLFISVKRDQEBY-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)cyclohexane Chemical compound CC(C)(C)OOC1(OOC(C)(C)C)CCCCC1 HSLFISVKRDQEBY-UHFFFAOYSA-N 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- SPTHWAJJMLCAQF-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene;hydrogen peroxide Chemical compound OO.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-N 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- AYMDJPGTQFHDSA-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-ethoxyethane Chemical compound CCOCCOCCOC=C AYMDJPGTQFHDSA-UHFFFAOYSA-N 0.000 description 1
- XSZYESUNPWGWFQ-UHFFFAOYSA-N 1-(2-hydroperoxypropan-2-yl)-4-methylcyclohexane Chemical compound CC1CCC(C(C)(C)OO)CC1 XSZYESUNPWGWFQ-UHFFFAOYSA-N 0.000 description 1
- DDNSSUJNMOQQKI-UHFFFAOYSA-N 1-prop-1-ynylperoxyprop-1-yne Chemical compound CC#COOC#CC DDNSSUJNMOQQKI-UHFFFAOYSA-N 0.000 description 1
- HQOVXPHOJANJBR-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)butane Chemical compound CC(C)(C)OOC(C)(CC)OOC(C)(C)C HQOVXPHOJANJBR-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
- JGBAASVQPMTVHO-UHFFFAOYSA-N 2,5-dihydroperoxy-2,5-dimethylhexane Chemical compound OOC(C)(C)CCC(C)(C)OO JGBAASVQPMTVHO-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
- XKBHBVFIWWDGQX-UHFFFAOYSA-N 2-bromo-3,3,4,4,5,5,5-heptafluoropent-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(Br)=C XKBHBVFIWWDGQX-UHFFFAOYSA-N 0.000 description 1
- VGZZAZYCLRYTNQ-UHFFFAOYSA-N 2-ethoxyethoxycarbonyloxy 2-ethoxyethyl carbonate Chemical compound CCOCCOC(=O)OOC(=O)OCCOCC VGZZAZYCLRYTNQ-UHFFFAOYSA-N 0.000 description 1
- ZACVGCNKGYYQHA-UHFFFAOYSA-N 2-ethylhexoxycarbonyloxy 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC(=O)OOC(=O)OCC(CC)CCCC ZACVGCNKGYYQHA-UHFFFAOYSA-N 0.000 description 1
- MIRQGKQPLPBZQM-UHFFFAOYSA-N 2-hydroperoxy-2,4,4-trimethylpentane Chemical compound CC(C)(C)CC(C)(C)OO MIRQGKQPLPBZQM-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- IISCRELTMNKFMH-UHFFFAOYSA-N 2-methoxypropan-2-yl 2-methoxypropan-2-yloxycarbonyloxy carbonate Chemical compound COC(C)(C)OC(=O)OOC(=O)OC(C)(C)OC IISCRELTMNKFMH-UHFFFAOYSA-N 0.000 description 1
- TVWBTVJBDFTVOW-UHFFFAOYSA-N 2-methyl-1-(2-methylpropylperoxy)propane Chemical compound CC(C)COOCC(C)C TVWBTVJBDFTVOW-UHFFFAOYSA-N 0.000 description 1
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 1
- KFGFVPMRLOQXNB-UHFFFAOYSA-N 3,5,5-trimethylhexanoyl 3,5,5-trimethylhexaneperoxoate Chemical compound CC(C)(C)CC(C)CC(=O)OOC(=O)CC(C)CC(C)(C)C KFGFVPMRLOQXNB-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- MKTOIPPVFPJEQO-UHFFFAOYSA-N 4-(3-carboxypropanoylperoxy)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)OOC(=O)CCC(O)=O MKTOIPPVFPJEQO-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
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- AUNAPVYQLLNFOI-UHFFFAOYSA-L [Pb++].[Pb++].[Pb++].[O-]S([O-])(=O)=O.[O-][Cr]([O-])(=O)=O.[O-][Mo]([O-])(=O)=O Chemical compound [Pb++].[Pb++].[Pb++].[O-]S([O-])(=O)=O.[O-][Cr]([O-])(=O)=O.[O-][Mo]([O-])(=O)=O AUNAPVYQLLNFOI-UHFFFAOYSA-L 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- BXIQXYOPGBXIEM-UHFFFAOYSA-N butyl 4,4-bis(tert-butylperoxy)pentanoate Chemical compound CCCCOC(=O)CCC(C)(OOC(C)(C)C)OOC(C)(C)C BXIQXYOPGBXIEM-UHFFFAOYSA-N 0.000 description 1
- CJOBVZJTOIVNNF-UHFFFAOYSA-N cadmium sulfide Chemical compound [Cd]=S CJOBVZJTOIVNNF-UHFFFAOYSA-N 0.000 description 1
- ONIOAEVPMYCHKX-UHFFFAOYSA-N carbonic acid;zinc Chemical compound [Zn].OC(O)=O ONIOAEVPMYCHKX-UHFFFAOYSA-N 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- BSVQJWUUZCXSOL-UHFFFAOYSA-N cyclohexylsulfonyl ethaneperoxoate Chemical compound CC(=O)OOS(=O)(=O)C1CCCCC1 BSVQJWUUZCXSOL-UHFFFAOYSA-N 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
- YMRYNEIBKUSWAJ-UHFFFAOYSA-N ditert-butyl benzene-1,3-dicarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC(C(=O)OOC(C)(C)C)=C1 YMRYNEIBKUSWAJ-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920002681 hypalon Polymers 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- XNTUJOTWIMFEQS-UHFFFAOYSA-N octadecanoyl octadecaneperoxoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCCCCCCCC XNTUJOTWIMFEQS-UHFFFAOYSA-N 0.000 description 1
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 239000010734 process oil Substances 0.000 description 1
- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Description
本発明は有機過酸化物加硫により着色ゴム組成
物を形成するための未加流ゴム組成物に関する。
従来黒以外の赤色、青色等に着色したゴムは、
未加流ゴムに単に顔料等を混合して、その後加硫
して製造されている。この場合、加流ゴム中にお
いて、顔料とゴム分子とが混合物の形をなしてい
る。しかしこのような顔料とゴム成分との混合物
が外的条件にさらされた時、水分で顔料が流れ出
たり、日光等の直射によつて顔料自体が分解した
り、ゴム分子自体の崩壊により、顔料自体の流出
が生じた。このような顔料の流出は、ゴム製品の
退色を意味する。したがつて従来において、黒以
外の着色ゴムの用途は主として室内に限られてい
た。又そのような着色ゴムは屋外に使用されたり
しても、１〜２月で交換しなければならないか、
又は退色したまま放置して使用しているのが現状
であつた。
本発明は、加熱により、有機過酸化物が分解し
当分解物の作用により生成する活性なゴム分子ラ
ジカルに着目し、退色又は変色しないゴムについ
て幅広い研究を行つた結果、顔料又は染料分子を
ゴム分子に結合させたと考えられる方法によつて
退色又は変色しないゴムの開発に成功し本発明に
至つた。
本発明は、有機過酸化物、１種又はそれ以上の
求電子試薬、有機顔料又は染料および無機顔料か
らなる群から選ばれた着色剤を混入したことを特
徴とする、有機過酸化物加硫により着色ゴム組成
物を形成するための未加流ゴム組成物に関する。
本発明組成物を加熱した時、過酸化物加硫が行
なわれると同時に有機顔料あるいは染料に存在し
ている変性され得る基又は無機顔料の金属原子が
活性なゴム分子ラジカルに結合して、退色又は変
色しない着色ゴム組成物が形成されると考えられ
る。
本発明において使用されるべきゴムとしては天
然ゴム（NR）および合成ゴムのようなすべての
ゴムが使用可能である。例えばスチレンブタジエ
ンゴム（SBR）アクリロニトリルブタジエンゴ
ム（NBR）、クロロプレンゴム（CR）、ポリイソ
プレンゴム（IR）、ポリブタジエンゴム（BR）、
エチレンプロピレンゴム（EPR）、およびエチレ
ン−プロピレン−ジエン三元共重合体ゴム
（EPDM）クロロスルホン化ポリエチレン
（CMS）、エチレン酢酸ビニル共重合体（EVA）
等その他公知の合成ゴムが使用できる。
求電子試薬は有機顔料又は染料の末端の極性基
又は無機顔料の金属原子から電子を取つて、これ
らをに荷電させる役割を果す。求電子試薬の例
は、キノン類、四塩化スズ、塩化アルミニウム、
およびZnO，PbO等の両性金属化物と、それらの
金属の弱酸塩との混合物等である。特に四塩化ス
ズ、ZnOとZnCO3との混合物、キノン類、AlCl3
が好ましい。この求電子試薬は未加流ゴム組成物
100部に対し、0.2−20重量部、好ましくは１〜12
重量部である。加流ゴム組成物の性質を害せず又
は加硫中に分解するものであればこれらの求電子
試薬をもつと多く使用できる。
有機顔料又は染料としては、求電子試薬によつ
て変性され得る基を有する公知のものがすべて使
用できる。特にベンゼン核上にNH2，NO2，
OCH3，OC2H5，CONH2，Cl，CF3等が存在す
る顔料又は染料が好ましい。
又は無機顔料はほとんどすべて金属原子を有す
るので、本発明において使用できる。例えば、亜
鉛華、アルミナ白、酸化チタン、ベンガラ、リサ
ージ、鉛丹、黄鉛、鉛臼、亜鉛黄、モリブデン
赤、カドミウム黄等である。
顔料又は染料の使用量は本発明のゴム組成物か
ら形成される加流ゴム組成物の用途による。
有機過酸化物の例は、アセチルシクロヘキシル
スルホニルパーオキシド、イソ−ブチルパーオキ
シド、ジ−イソプロイルパーオキシジカーボネー
ト、ジ−ｎ−プロピルパーオキシジカーボネー
ト、ジ（２−エトキシエチル）パーオキシジカー
ボネート、ジ（メトキシイソプロピル）パーオキ
シジカーボネート、ジ（２−エチルヘキシル）パ
ーオキシジカーボネート、ｔ−ブチルパーオキシ
ネオデカノネート、２，４−ジクロロベンゾイル
パーオキシド、ｔ−ブチルパーオキシピバレー
ト、３，５，５−トリメチルヘキサノイルパーオ
キシド、オクタノイルパーオキシド、デタノイル
パーオキシド、ラウロイルパーオキシド、ステア
ロイルパーオキシド、プロピニルパーオキシド、
コハク酸パーオキシド、アセチルパーオキシド、
ｔ−ブチルパーオキシ（２−エチルヘキサノエー
ト）、ｍ−トルオイルパーオキシド、ベンゾイル
パーオキシド、ｔ−ブチルパーオキシイソブチレ
ート、１，１−ビス（ｔ−ブチルパーオキシ）
３，５，５−トリメチルシクロヘキサン、１，１
−ビス（ｔ−ブチルパーオキシ）シクロヘキサ
ン、ｔ−ブチルパーオキシマレイン酸、ｔ−ブチ
ルパーオキシラウレート、ｔ−ブチルパーオキシ
３，５，５−トリメチルヘキサノエート、シクロ
ヘキサノニパーオキシド、ｔ−ブチルパーオキシ
イソプロピルカーボネート、２，５−シメチル−
２，５−ジ（ベンゾイルパーオキシ）ヘキサン、
ｔ−ブチルパーオキシアセテート、２，２−ビス
（ｔ−ブチルパーオキシ）ブタン、ｔ−ブチルパ
ーオキシベンゾエート、ｎ−ブチル−４，４−ビ
ス（ｔ−ブチルパーオキシ）バレレート、ジ−ｔ
−ブチルジパーオキシイソフタレート、メチルエ
チルケトンパーオキシド、α，α′−ビス（ｔ−ブ
チルパーオキシイソプロピル）ベンゼン、ジクミ
ルパーオキシド、２，５−ジメチル−２，５−ジ
（ｔ−ブチルパーオキシ）ヘキサン、ｔ−ブチル
クミルパーオキシド、ジ−イソプロピルベンゼン
ヒドロパーオキシド、ジ−ｔ−ブチルパーオキシ
ド、ｐ−メンタンヒドロパーオキシド、２，５−
ジメチル−２，５−ジ（ｔ−ブチルパーオキシ）
ヘキシン−３，１，１，３，３−テトラメチルブ
チルヒドロパーオキシド、２，５−ジメチルヘキ
サン−２，５−ジヒドロパーオキシド、クメンヒ
ドロパーオキシドおよびｔ−ブチルヒドロパーオ
キシドである。このような過酸化物の使用量は樹
脂100重量部に対し0.5〜５部程度である。
その他未加流ゴム組成物には通常のゴム成分に
添加される公知の他の加硫剤、加硫助剤、加工助
剤、補強剤、軟化剤、着色剤、増量剤、老化防止
剤および、紫外線吸収剤等が添加されていても良
い。
本発明では加硫前に求電子試薬および特定な顔
料又は染料をゴム組成物に加えるので、通常条件
の加硫工程中その顔料又は染料がゴム分子に結合
すると考えられる。
本発明の組成物を使用した場合、その顔料又は
染料分子が一部分又は全部がゴム成分に結合する
ので、従来のものより、退色又は変色が起りにく
い。又そのような顔料の作用によつて加流ゴムの
強度がさらに増加したという特徴を有する。
以下に本発明の実施例を示す。単位は重量によ
る。
実施例 １
EPDM 100部
ステアリン酸 １〃
パラフイン １〃
２−メルカプトベンツイミダゾール 0.5〃
プロセスオイル 10〃
ケイ酸 30〃
ピグメントイエロー83 １〃
トリメチロールプロパントリメタクリレート
３〃
ZnO 5.5〃
ZnCO3 5.5〃
２，５ジメチル２，５ジ（ターシヤルブチルペ
ルオキシ）ヘキサン ２〃
からなる未加硫ゴム組成物を175℃、10分間150
Kg／cm2の圧力で加硫した。その性質は第１表に示
す。
比較例 １
亜鉛の弱酸塩であるZnCO3を添加せずに実施例
１の操作を繰返した。その結果を第１表に示す。
比較例 ２
ピグメントイエロー83等の顔料又は染料を添加
せずに、実施例１の操作を繰返した。その結果を
第１表に示す。
実施例 ２−11
第１表に記載の成分を使用して、加硫操作を行
つた。その結果を第１表に示す。
The present invention relates to green rubber compositions for forming colored rubber compositions by organic peroxide vulcanization. Traditionally, rubber colored in colors other than black, such as red or blue,
It is manufactured by simply mixing pigments etc. with uncured rubber and then vulcanizing it. In this case, the pigment and rubber molecules are in the form of a mixture in the hot-flow rubber. However, when such a mixture of pigment and rubber components is exposed to external conditions, the pigment may flow out due to moisture, the pigment itself may decompose due to direct sunlight, or the rubber molecules themselves may disintegrate. A leak of its own occurred. Such pigment outflow means fading of the rubber product. Therefore, in the past, the use of colored rubber other than black was mainly limited to indoor use. Also, even if such colored rubber is used outdoors, it must be replaced every January or February.
Or, the current situation is that the color is left as it is and used. The present invention focused on the active rubber molecule radicals generated by the action of the decomposed product when organic peroxides are decomposed by heating, and as a result of extensive research into rubbers that do not fade or change color, pigment or dye molecules are added to the rubber. The present invention was achieved by successfully developing a rubber that does not fade or change color by a method thought to be bonded to molecules. The present invention relates to organic peroxide vulcanization, characterized in that it incorporates a coloring agent selected from the group consisting of an organic peroxide, one or more electrophiles, an organic pigment or dye, and an inorganic pigment. The present invention relates to an unwashed rubber composition for forming a colored rubber composition. When the composition of the present invention is heated, peroxide vulcanization takes place, and at the same time, the modifiable groups present in the organic pigment or dye or the metal atoms of the inorganic pigment bond to active rubber molecule radicals, resulting in discoloration. Alternatively, it is believed that a colored rubber composition that does not change color is formed. As the rubber to be used in the present invention, all rubbers can be used, such as natural rubber (NR) and synthetic rubber. For example, styrene butadiene rubber (SBR), acrylonitrile butadiene rubber (NBR), chloroprene rubber (CR), polyisoprene rubber (IR), polybutadiene rubber (BR),
Ethylene propylene rubber (EPR), ethylene-propylene-diene terpolymer rubber (EPDM), chlorosulfonated polyethylene (CMS), ethylene vinyl acetate copolymer (EVA)
Other known synthetic rubbers can be used. The electrophilic reagent plays the role of taking electrons from the terminal polar groups of organic pigments or dyes or the metal atoms of inorganic pigments and charging them. Examples of electrophiles are quinones, tin tetrachloride, aluminum chloride,
and mixtures of amphoteric metal compounds such as ZnO and PbO and weak acid salts of these metals. Especially tin tetrachloride, mixtures of ZnO and ZnCO3 , quinones, AlCl3
is preferred. This electrophile is an unwashed rubber composition.
0.2-20 parts by weight per 100 parts, preferably 1-12 parts by weight
Parts by weight. Many of these electrophilic reagents can be used as long as they do not impair the properties of the hot-flow rubber composition or are decomposed during vulcanization. As the organic pigment or dye, all known organic pigments or dyes having a group that can be modified with an electrophilic reagent can be used. In particular, NH 2 , NO 2 ,
Pigments or dyes in which OCH 3 , OC 2 H 5 , CONH 2 , Cl, CF 3 and the like are present are preferred. Alternatively, almost all inorganic pigments have metal atoms and can therefore be used in the present invention. Examples include zinc white, alumina white, titanium oxide, red iron oxide, litharge, red lead, yellow lead, lead mortar, zinc yellow, molybdenum red, and cadmium yellow. The amount of pigment or dye used depends on the use of the hot-wash rubber composition formed from the rubber composition of the present invention. Examples of organic peroxides are acetylcyclohexylsulfonyl peroxide, iso-butyl peroxide, di-isoproyl peroxydicarbonate, di-n-propyl peroxydicarbonate, di(2-ethoxyethyl)peroxydicarbonate. , di(methoxyisopropyl)peroxydicarbonate, di(2-ethylhexyl)peroxydicarbonate, t-butylperoxyneodecanonate, 2,4-dichlorobenzoyl peroxide, t-butylperoxypivalate, 3 , 5,5-trimethylhexanoyl peroxide, octanoyl peroxide, detanoyl peroxide, lauroyl peroxide, stearoyl peroxide, propynyl peroxide,
succinic acid peroxide, acetyl peroxide,
t-Butylperoxy (2-ethylhexanoate), m-toluoyl peroxide, benzoyl peroxide, t-butylperoxyisobutyrate, 1,1-bis(t-butylperoxy)
3,5,5-trimethylcyclohexane, 1,1
-Bis(t-butylperoxy)cyclohexane, t-butylperoxymaleic acid, t-butylperoxylaurate, t-butylperoxy 3,5,5-trimethylhexanoate, cyclohexanonyperoxide, t- Butyl peroxyisopropyl carbonate, 2,5-dimethyl-
2,5-di(benzoylperoxy)hexane,
t-Butylperoxyacetate, 2,2-bis(t-butylperoxy)butane, t-butylperoxybenzoate, n-butyl-4,4-bis(t-butylperoxy)valerate, di-t
-butyldiperoxyisophthalate, methyl ethyl ketone peroxide, α,α'-bis(t-butylperoxyisopropyl)benzene, dicumyl peroxide, 2,5-dimethyl-2,5-di(t-butylperoxy) ) Hexane, t-butylcumyl peroxide, di-isopropylbenzene hydroperoxide, di-t-butyl peroxide, p-menthane hydroperoxide, 2,5-
Dimethyl-2,5-di(t-butylperoxy)
They are hexyne-3,1,1,3,3-tetramethylbutyl hydroperoxide, 2,5-dimethylhexane-2,5-dihydroperoxide, cumene hydroperoxide and t-butyl hydroperoxide. The amount of such peroxide used is about 0.5 to 5 parts per 100 parts by weight of the resin. Other uncured rubber compositions include other known vulcanizing agents, vulcanization aids, processing aids, reinforcing agents, softeners, colorants, fillers, anti-aging agents, and , an ultraviolet absorber, etc. may be added. Since the present invention adds an electrophile and a specific pigment or dye to the rubber composition prior to vulcanization, it is believed that the pigment or dye becomes attached to the rubber molecules during the vulcanization process under normal conditions. When using the composition of the present invention, fading or discoloration is less likely to occur than with conventional compositions because the pigment or dye molecules are partially or fully bound to the rubber component. Furthermore, the strength of the hot-flow rubber is further increased due to the action of such pigments. Examples of the present invention are shown below. Units are based on weight. Example 1 EPDM 100 parts Stearic acid 1 Paraffin 1 2-mercaptobenzimidazole 0.5 Process oil 10 Silicic acid 30 Pigment Yellow 83 1 Trimethylolpropane trimethacrylate
3〃 ZnO 5.5〃 ZnCO 3 5.5〃 2,5 dimethyl 2,5 di(tert-butylperoxy)hexane 2
Vulcanization was carried out at a pressure of Kg/cm 2 . Its properties are shown in Table 1. Comparative Example 1 The operation of Example 1 was repeated without adding ZnCO 3 , a weak acid salt of zinc. The results are shown in Table 1. Comparative Example 2 The procedure of Example 1 was repeated without adding any pigment or dye, such as Pigment Yellow 83. The results are shown in Table 1. Example 2-11 A vulcanization operation was performed using the components listed in Table 1. The results are shown in Table 1.
【表】【table】
【表】【table】
【表】【table】
【表】
本発明において、有機求電子試薬も又使用でき
る。有機求電子試薬を使用した実施例は以下に示
す。Table: Organic electrophiles can also be used in the present invention. Examples using organic electrophiles are shown below.
【表】【table】
Claims (1)
は染料および無機顔料からなる群から選ばれた着
色剤と有機過酸化物とを混入したことを特徴とす
る、過酸化物加硫により着色ゴム組成物を形成す
るための未加硫ゴム組成物。1. Rubber colored by peroxide vulcanization, characterized in that it contains an organic peroxide and a coloring agent selected from the group consisting of one or more electrophilic reagents, organic pigments or dyes, and inorganic pigments. An unvulcanized rubber composition for forming a composition.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13717983A JPS6028441A (en) | 1983-07-27 | 1983-07-27 | Unvulcanized rubber composition for forming colored rubber composition by vulcanization with organic peroxide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13717983A JPS6028441A (en) | 1983-07-27 | 1983-07-27 | Unvulcanized rubber composition for forming colored rubber composition by vulcanization with organic peroxide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6028441A JPS6028441A (en) | 1985-02-13 |
| JPH0244331B2 true JPH0244331B2 (en) | 1990-10-03 |
Family
ID=15192655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13717983A Granted JPS6028441A (en) | 1983-07-27 | 1983-07-27 | Unvulcanized rubber composition for forming colored rubber composition by vulcanization with organic peroxide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6028441A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6047042A (en) * | 1983-08-25 | 1985-03-14 | Toa Gomme Kogyo Kk | Colored rubber composition |
| JP2007031507A (en) * | 2005-07-25 | 2007-02-08 | Nof Corp | Process for producing crosslinked rubber |
-
1983
- 1983-07-27 JP JP13717983A patent/JPS6028441A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6028441A (en) | 1985-02-13 |
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