CN101641403A - 用于橡胶配混的加工稳定剂 - Google Patents
用于橡胶配混的加工稳定剂 Download PDFInfo
- Publication number
- CN101641403A CN101641403A CN200880009201A CN200880009201A CN101641403A CN 101641403 A CN101641403 A CN 101641403A CN 200880009201 A CN200880009201 A CN 200880009201A CN 200880009201 A CN200880009201 A CN 200880009201A CN 101641403 A CN101641403 A CN 101641403A
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- CN
- China
- Prior art keywords
- phenyl
- alkyl
- tertiary butyl
- rubber
- hydroxyl
- 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.)
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- 239000003381 stabilizer Substances 0.000 title claims abstract description 25
- 238000010058 rubber compounding Methods 0.000 title claims description 6
- -1 C1-C20alkyl Chemical group 0.000 claims abstract description 124
- 229920001971 elastomer Polymers 0.000 claims abstract description 54
- 239000005060 rubber Substances 0.000 claims abstract description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 23
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 21
- 239000001301 oxygen Substances 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000013329 compounding Methods 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000003944 tolyl group Chemical group 0.000 claims abstract description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims abstract description 3
- 125000005504 styryl group Chemical group 0.000 claims abstract description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000003963 antioxidant agent Substances 0.000 claims description 6
- 239000000945 filler Substances 0.000 claims description 6
- 230000003078 antioxidant effect Effects 0.000 claims description 5
- 239000005864 Sulphur Substances 0.000 claims description 4
- 235000012424 soybean oil Nutrition 0.000 claims description 4
- 239000003549 soybean oil Substances 0.000 claims description 4
- 239000004902 Softening Agent Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 238000003780 insertion Methods 0.000 claims description 3
- 230000037431 insertion Effects 0.000 claims description 3
- 229910044991 metal oxide Inorganic materials 0.000 claims description 3
- 150000004706 metal oxides Chemical class 0.000 claims description 3
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 230000003068 static effect Effects 0.000 claims description 3
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 239000012752 auxiliary agent Substances 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims description 2
- 238000004073 vulcanization Methods 0.000 claims description 2
- 239000012936 vulcanization activator Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 abstract description 2
- 239000011593 sulfur Substances 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 101100439662 Arabidopsis thaliana CHR5 gene Proteins 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 description 33
- 239000000203 mixture Substances 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000002585 base Substances 0.000 description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- 238000002156 mixing Methods 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 9
- GAODDBNJCKQQDY-UHFFFAOYSA-N 2-methyl-4,6-bis(octylsulfanylmethyl)phenol Chemical compound CCCCCCCCSCC1=CC(C)=C(O)C(CSCCCCCCCC)=C1 GAODDBNJCKQQDY-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 239000012964 benzotriazole Substances 0.000 description 7
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 7
- 230000006698 induction Effects 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- 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 6
- 229920002943 EPDM rubber Polymers 0.000 description 6
- 239000004594 Masterbatch (MB) Substances 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 239000012190 activator Substances 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 6
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 6
- 229920003048 styrene butadiene rubber Polymers 0.000 description 6
- GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 description 5
- HTSVYUUXJSMGQC-UHFFFAOYSA-N 2-chloro-1,3,5-triazine Chemical class ClC1=NC=NC=N1 HTSVYUUXJSMGQC-UHFFFAOYSA-N 0.000 description 5
- PZBQVZFITSVHAW-UHFFFAOYSA-N 5-chloro-2h-benzotriazole Chemical compound C1=C(Cl)C=CC2=NNN=C21 PZBQVZFITSVHAW-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000006229 carbon black Substances 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 229940059574 pentaerithrityl Drugs 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 4
- GLDQAMYCGOIJDV-UHFFFAOYSA-N 2,3-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1O GLDQAMYCGOIJDV-UHFFFAOYSA-N 0.000 description 4
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- RHCPKXALNJKMQT-UHFFFAOYSA-N CC1(NC(CC(C1)C(CCCCC)(N)N)(C)C)C Chemical compound CC1(NC(CC(C1)C(CCCCC)(N)N)(C)C)C RHCPKXALNJKMQT-UHFFFAOYSA-N 0.000 description 4
- ICHKVCYUNCKCGL-UHFFFAOYSA-N CN(C)C.OCCCCCCO Chemical compound CN(C)C.OCCCCCCO ICHKVCYUNCKCGL-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 4
- 244000043261 Hevea brasiliensis Species 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 239000002174 Styrene-butadiene Substances 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- COVMBDWAODLWIB-UHFFFAOYSA-N n'-(2-hydroxyethyl)oxamide Chemical compound NC(=O)C(=O)NCCO COVMBDWAODLWIB-UHFFFAOYSA-N 0.000 description 4
- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 4
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 229920003052 natural elastomer Polymers 0.000 description 4
- 229920001194 natural rubber Polymers 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 description 3
- VHOQXEIFYTTXJU-UHFFFAOYSA-N Isobutylene-isoprene copolymer Chemical compound CC(C)=C.CC(=C)C=C VHOQXEIFYTTXJU-UHFFFAOYSA-N 0.000 description 3
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 241000282485 Vulpes vulpes Species 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 3
- 230000001771 impaired effect Effects 0.000 description 3
- ODGYWRBCQWKSSH-UHFFFAOYSA-N n'-ethylpropane-1,3-diamine Chemical compound CCNCCCN ODGYWRBCQWKSSH-UHFFFAOYSA-N 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- 150000002815 nickel Chemical class 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical group 0.000 description 2
- XURGPLKLBUMZTN-UHFFFAOYSA-N 2-butyl-3-methylbenzene-1,4-diol Chemical group CCCCC1=C(C)C(O)=CC=C1O XURGPLKLBUMZTN-UHFFFAOYSA-N 0.000 description 2
- LCQXXVFFJHBYME-UHFFFAOYSA-N 2-butyl-4-hydroxybenzoic acid Chemical group CCCCC1=CC(O)=CC=C1C(O)=O LCQXXVFFJHBYME-UHFFFAOYSA-N 0.000 description 2
- SXGXVOZDLWXVKM-UHFFFAOYSA-N 3-dodecylpyrrolidine-2,5-dione Chemical compound CCCCCCCCCCCCC1CC(=O)NC1=O SXGXVOZDLWXVKM-UHFFFAOYSA-N 0.000 description 2
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- MSGFMKMFGGXSTO-UHFFFAOYSA-N C(C)(C)(C)C=1C=C(C(=CC1O)CN)CCCC Chemical compound C(C)(C)(C)C=1C=C(C(=CC1O)CN)CCCC MSGFMKMFGGXSTO-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
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- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006487 butyl benzyl group Chemical group 0.000 description 2
- 238000004939 coking Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000008380 degradant Substances 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- SWRGUMCEJHQWEE-UHFFFAOYSA-N ethanedihydrazide Chemical compound NNC(=O)C(=O)NN SWRGUMCEJHQWEE-UHFFFAOYSA-N 0.000 description 2
- 229920005555 halobutyl Polymers 0.000 description 2
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Abstract
本发明描述了改进的制备混炼胶的方法,包括在基于橡胶重量的0.1至2%的式I的加工稳定剂存在下在125至200℃将橡胶和组分配混:其中R1是氢、C1-C20烷基、苯乙烯基、α-甲基-苯乙烯基或-CH2-S-R3;或被C2-C20链烯基、C3-C20炔基、C5-C9环烷基、苯基或甲苯基取代的C1-C20烷基;R2是C1-C20烷基或-CH2-S-R3,R3是C1-C20烷基;被苯基、羟基、氰基、甲酰基、乙酰基或-O-CO-R5取代的C1-C20烷基;C2-C20链烯基、C3-C20炔基、C5-C9环烷基;或被羟基、苯基、4-氯-苯基、2-甲氧基羰基苯基、对甲苯基、1,3-苯并噻唑-2-基、-(CHR5)nCOOR6或-(CHR5)nCONR7R8取代的C5-C9环烷基;R4是氢或甲基,R5是氢或C1-C6烷基,R6是C1-C20烷基;被氧或硫插入的C3-C20烷基;C5-C9环烷基、苯基、苄基或甲苯基,R7和R8彼此独立地为氢或C1-C6烷基,且n是1或2。
Description
本发明涉及改进的制备混炼胶的方法,包括在基于橡胶重量的0.1至2%的特定类别含硫加工稳定剂存在下在125至200℃将橡胶和组分配混。
尽管存在加工问题,但市场上没有用于橡胶配混的特定加工稳定剂。用于硫化产品稳定化的抗降解剂在一定程度上被认为提供了加工稳定性。但是,它们作为加工稳定剂的性能非常有限。
现已发现,非常特定类别的含硫稳定剂尤其有益于在125至200℃的橡胶配混。
本发明因此提供了改进的制备混炼胶的方法,包括在基于橡胶重量的0.1-2%的式I的加工稳定剂存在下在125至200℃将橡胶和组分配混:
其中
R1是氢、C1-C20烷基、苯乙烯基、α-甲基-苯乙烯基或-CH2-S-R3;或被C2-C20链烯基、C3-C20炔基、C5-C9环烷基、苯基或甲苯基取代的C1-C20烷基;
R3是C1-C20烷基;被苯基、羟基、氰基、甲酰基、乙酰基或-O-CO-R5取代的C1-C20烷基;C2-C20链烯基、C3-C20炔基、C5-C9环烷基;或被羟基、苯基、4-氯-苯基、2-甲氧基羰基苯基、对甲苯基、1,3-苯并噻唑-2-基、-(CHR5)nCOOR6或-(CHR5)nCONR7R8取代的C5-C9环烷基;
R4是氢或甲基,
R5是氢或C1-C6烷基,
R6是C1-C20烷基;被氧或硫插入的C3-C20烷基;C5-C9环烷基、苯基、苄基或甲苯基,
R7和R8彼此独立地为氢或C1-C6烷基,且
n是1或2。
具有最多20个碳原子的烷基是支链或直链基团,例如甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、2-乙基丁基、正戊基、异戊基、1-甲基戊基、1,3-二甲基丁基、正己基、1-甲基己基、正庚基、异庚基、1,1,3,3-四甲基丁基、1-甲基庚基、3-甲基庚基、正辛基、2-乙基己基、1,1,3-三甲基己基、1,1,3,3-四甲基戊基、壬基、癸基、十一烷基、1-甲基十一烷基、十二烷基、1,1,3,3,5,5-六甲基己基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基或十八烷基。
C2-C20链烯基是例如乙烯基、烯丙基(丙-2-烯基)、丁-3-烯基、戊-4-烯基、己-5-烯基、辛-7-烯基、癸-9-烯基或十二-11-烯基。
C3-C20炔基是例如丙炔基、丁-3-炔基、己-5-炔基、辛-7-炔基、癸-9-炔基、十二-11-炔基、十四-13-炔基、十六-15-炔基、十八-17-炔基或二十-19-炔基。
C5-C9环烷基是例如环戊基、环己基、环庚基、环辛基、环壬基,特别是环己基。
苯基取代的C1-C20烷基是例如苄基、苯乙基、α-甲基苄基、α,α-二甲基苄基、苯基丁基、苯基-α,α-二甲基丙基、苯基己基、苯基-α,α-二甲基丁基、苯基辛基或苯基-α,α-二甲基己基。
被一个或两个羟基取代的C1-C20烷基是例如2-羟乙基、2-羟丙基、2-羟丁基、2-羟己基、2-羟辛基、2-羟癸基、2-羟基十二烷基、2-羟基十四烷基、2-羟基十六烷基、2-羟基十八烷基、2-羟基二十烷基或2,3-二羟丙基。
被苯基和羟基取代的C1-C20烷基是例如1-苯基-2-羟乙基。
被氰基取代的C1-C20烷基是例如2-氰乙基。
被1至5个氧或硫插入的C3-C20烷基是例如3-氧杂丙基、3-硫杂-丙基、3-氧杂丁基、3-硫杂丁基、3-氧杂戊基、3-硫杂戊基、3,6-二氧杂庚基、3,6,9-三氧杂癸基或3,6,9,12,15,18-六氧杂十九烷基。
特别改进的制备混炼胶的方法包括其中R3为C6-C18烷基的式I的化合物。
优选的制备混炼胶的改进方法包括式I的化合物,其中:
R1是甲基,
R2是-CH2-S-R3,
R3是C8-C12烷基,且
R4是氢。
特别优选的是包括式A1或A2的化合物作为式I的化合物的改进的制备混炼胶的方法。
式A1和A2的化合物可例如作为Irganox 1520(RTM)和Irganox 1726(RTM)购得[可获自Ciba Specialty Chemicals Inc.]。
式I的化合物的制备例如公开在美国专利6,365,781B2中,并且可以通过如上述参考文献中公开的本领域已知方法制备。
橡胶被理解为是指在在室温下在小载荷下显著形变后迅速地大致恢复其原始形状的大分子材料。也参见Hans-Georg Elias,″An Introduction toPolymer Science″,Section 12.″Elastomers″,第388-393页,1997,VCHVerlagsgesellschaft mbH,Weinheim,Germany或″Ullmann′s Encyclopediaof Industrial Chemistry,第五完全修订版,第A23卷″,第221-440页(1993)。
本发明的方法中可存在的橡胶的实例是下列材料:
1.共轭二烯的聚合物,例如聚丁二烯或聚异戊二烯。
2.单-烯烃和二-烯烃与彼此或与其它乙烯基单体的共聚物,例如丙烯-异丁烯共聚物、丙烯-丁二烯共聚物、异丁烯-异戊二烯共聚物、乙烯-丙烯酸烷基酯共聚物、乙烯-甲基丙烯酸烷基酯共聚物、乙烯-乙酸乙烯酯共聚物、丙烯腈-丁二烯共聚物、以及乙烯与丙烯和与二烯(例如己二烯、二环戊二烯或亚乙基降冰片烯)的三元共聚物。
3.苯乙烯或α-甲基苯乙烯与二烯或与丙烯酸衍生物的共聚物,例如苯乙烯-丁二烯、苯乙烯-丁二烯-异戊二烯、苯乙烯-丁二烯-丙烯酸烷基酯和苯乙烯-丁二烯-甲基丙烯酸烷基酯;苯乙烯的嵌段共聚物,例如苯乙烯-丁二烯-苯乙烯、苯乙烯-异戊二烯-苯乙烯和苯乙烯-乙烯丁烯-苯乙烯。
4.含卤素的聚合物,例如聚氯丁二烯、氯化橡胶、异丁烯-异戊二烯的氯化或溴化共聚物(卤丁基橡胶)、异丁烯与对甲基苯乙烯的卤化共聚物。
5.天然橡胶。
6.天然或合成橡胶的水乳状液,例如天然橡胶胶乳或羧化苯乙烯-丁二烯共聚物的胶乳。
优选地,橡胶组分基于高度不饱和的橡胶,例如天然橡胶和/或苯乙烯-丁二烯橡胶和/或丁二烯橡胶。本发明实践中可用的高度不饱和聚合物的代表是二烯橡胶。这类橡胶通常具有大约20至大约450的碘值,但也可以使用具有更高或更低(例如50-100)碘值的高度不饱和橡胶。可用的二烯橡胶的实例是基于例如1,3-丁二烯;2-甲基-1,3-丁二烯;1,3-戊二烯;2,3-二甲基-1,3-丁二烯之类的共轭二烯的聚合物,以及这类共轭二烯与例如苯乙烯、α-甲基苯乙烯、乙炔(例如乙烯基乙炔)、丙烯腈、甲基丙烯酸酯、丙烯酸甲酯、丙烯酸乙酯、甲基丙烯酸甲酯、甲基丙烯酸乙酯、乙酸乙烯酯之类的单体的共聚物。优选的高度不饱和的橡胶包括天然橡胶、顺式-聚异戊二烯、聚丁二烯、聚(苯乙烯-丁二烯)、苯乙烯-异戊二烯共聚物、异戊二烯-丁二烯共聚物、苯乙烯-异戊二烯-丁二烯三聚体、聚氯丁二烯、氯异丁烯-异戊二烯、腈-氯丁二烯、苯乙烯-氯丁二烯和聚(丙烯腈-丁二烯)。此外,两种或多种高度不饱和橡胶与具有较低不饱和的弹性体(例如EPDM、EPR、丁基橡胶或卤化丁基橡胶)的混合物也在本发明的范围内。
基于要配混的橡胶的重量,式I的化合物通常以0.1至2%、例如0.1至1.5%、优选0.2至1.5%的量添加到要配混的橡胶中。
除了式I的化合物外,本发明的方法还可以包含其它添加剂,例如下述:
1.抗氧化剂
1.1.烷基化的单酚,例如2,6-二-叔丁基-4-甲基酚、2-叔丁基-4,6-二-甲基酚、2,6-二-叔丁基-4-乙基酚、2,6-二-叔丁基-4-正丁基酚、2,6-二-叔丁基-4-异丁基酚、2,6-二环戊基-4-甲基酚、2-(α-甲基环己基)-4,6-二甲基酚、2,6-双十八烷基-4-甲基酚、2,4,6-三环己基酚、2,6-二-叔丁基-4-甲氧基甲基酚、在侧链中是直链或支链的壬基酚,例如2,6-二-壬基-4-甲基酚、2,4-二甲基-6-(1′-甲基十一烷-1′-基)酚、2,4-二甲基-6-(1′-甲基十七烷-1′-基)酚、2,4-二甲基-6-(1′-甲基十三烷-1′-基)酚,及其混合物。
1.2.氢醌和烷基化的氢醌,例如2,6-二-叔丁基-4-甲氧基酚、2,5-二-叔丁基氢醌、2,5-二-叔戊基氢醌、2,6-二苯基-4-十八烷氧基酚、2,6-二-叔丁基氢醌、2,5-二-叔丁基-4-羟基苯甲醚、3,5-二-叔丁基-4-羟基苯甲醚、3,5-二-叔丁基-4-羟苯基硬脂酸酯、双(3,5-二-叔丁基-4-羟苯基)己二酸酯。
1.3.生育酚,例如α-生育酚、β-生育酚、γ-生育酚、δ-生育酚及其混合物(维生素E)。
1.4.羟基化的硫代二苯基醚,例如2,2′-硫代双(6-叔丁基-4-甲基酚)、2,2′-硫代双(4-辛基酚)、4,4′-硫代双(6-叔丁基-3-甲酚)、4,4′-硫代双(6-叔丁基-2-甲酚)、4,4′-硫代双(3,6-二-仲戊基酚)、4,4′-双(2,6-二甲基-4-羟苯基)二硫化物。
1.5.亚烷基双酚和多酚,例如2,2′-亚甲基双(6-叔丁基-4-甲基酚)、2,2′-亚甲基双(6-叔丁基-4-乙基酚)、2,2′-亚甲基双[4-甲基-6-(α-甲基-环己基)酚]、2,2′-亚甲基双(4-甲基-6-环己基酚)、2,2′-亚甲基双(6-壬基-4-甲基酚)、2,2′-亚甲基双(4,6-二-叔丁基酚)、2,2′-亚乙基双(4,6-二-叔丁基酚)、2,2′-亚乙基双(6-叔丁基-4-异丁基酚)、2,2′-亚甲基双[6-(α-甲基苄基)-4-壬基酚]、2,2′-亚甲基双[6-(α,α-二甲基苄基)-4-壬基酚]、4,4′-亚甲基双(2,6-二-叔丁基酚)、4,4′-亚甲基双(6-叔丁基-2-甲基酚)、1,1-双(5-叔丁基-4-羟基-2-甲基苯基)丁烷、2,6-双(3-叔丁基-5-甲基-2-羟基苄基)-4-甲基酚、1,1,3-三(5-叔丁基-4-羟基-2-甲基苯基)丁烷、1,1-双(5-叔丁基-4-羟基-2-甲基苯基)-3-正十二烷基巯基丁烷、乙二醇双[3,3-双(3′-叔丁基-4′-羟基苯基)丁酸酯]、双(3-叔丁基-4-羟基-5-甲基-苯基)二环戊二烯、双[2-(3′-叔丁基-2′-羟基-5′-甲基苄基)-6-叔丁基-4-甲基苯基]对苯二甲酸酯、1,1-双-(3,5-二甲基-2-羟基苯基)丁烷、2,2-双(3,5-二-叔丁基-4-羟基苯基)丙烷、2,2-双-(5-叔丁基-4-羟基2-甲基苯基)-4-正十二烷基巯基丁烷、1,1,5,5-四(5-叔丁基-4-羟基-2-甲基苯基)戊烷、对甲酚和二环戊二烯的丁基化反应产物。
1.6.O-苄基、N-苄基和S-苄基化合物,例如3,5,3′,5′-四-叔丁基-4,4′-二羟基二苄基醚、十八烷基-4-羟基-3,5-二甲基苄基巯基乙酸酯、十三烷基-4-羟基-3,5-二-叔丁基苄基巯基乙酸酯、三(3,5-二-叔丁基-4-羟基苄基)胺、双(4-叔丁基-3-羟基-2,6-二甲基苄基)二硫代对苯二甲酸酯、双(3,5-二-叔丁基-4-羟基-苄基)硫化物、异辛基-3,5-二-叔丁基-4-羟基苄基巯基乙酸酯。
1.7.羟基苄基化的丙二酸酯,例如双十八烷基-2,2-双(3,5-二-叔丁基-2-羟基苄基)丙二酸酯、双-十八烷基-2-(3-叔丁基-4-羟基-5-甲基苄基)丙二酸酯、双-十二烷基巯基乙基-2,2-双(3,5-二-叔丁基-4-羟基苄基)丙二酸酯、双[4-(1,1,3,3-四甲基丁基)苯基]-2,2-双(3,5-二-叔丁基-4-羟基苄基)丙二酸酯。
1.8.芳族羟基苄基化合物,例如1,3,5-三(3,5-二-叔丁基-4-羟基苄基)-2,4,6-三甲基苯、1,4-双(3,5-二-叔丁基-4-羟基苄基)-2,3,5,6-四甲基苯、2,4,6-三(3,5-二-叔丁基-4-羟基苄基)酚。
1.9.三嗪化合物,例如2,4-双(辛基巯基)-6-(3,5-二-叔丁基-4-羟基苯胺基)-1,3,5-三嗪、2-辛基巯基-4,6-双(3,5-二-叔丁基-4-羟基苯胺基)-1,3,5-三嗪、2-辛基巯基-4,6-双(3,5-二-叔丁基-4-羟基苯氧基)-1,3,5-三嗪、2,4,6-三(3,5-二-叔丁基-4-羟基苯氧基)-1,2,3-三嗪、1,3,5-三(3,5-二-叔丁基-4-羟基苄基)异氰脲酸酯、1,3,5-三(4-叔丁基-3-羟基-2,6-二甲基苄基)异氰脲酸酯、2,4,6-三(3,5-二-叔丁基-4-羟基苯基乙基)-1,3,5-三嗪、1,3,5-三(3,5-二-叔丁基-4-羟基苯基丙酰基)-六氢-1,3,5-三嗪、1,3,5-三(3,5-二环己基-4-羟基苄基)异氰脲酸酯。
1.10.苄基膦酸酯,例如二甲基-2,5-二-叔丁基-4-羟基苄基膦酸酯、二乙基-3,5-二-叔丁基-4-羟基苄基膦酸酯、双十八烷基3,5-二-叔丁基-4-羟基苄基膦酸酯、双十八烷基-5-叔丁基-4-羟基-3-甲基苄基膦酸酯、3,5-二-叔丁基-4-羟基苄基膦酸的单乙酯的钙盐。
1.11.酰氨基酚,例如4-羟基月桂酰苯胺、4-羟基硬脂酰苯胺、N-(3,5-二-叔丁基-4-羟基苯基)氨基甲酸辛酯。
1.12.β-(3,5-二-叔丁基-4-羟基苯基)丙酸与一元醇或多元醇的酯,例如与下述化合物的酯:甲醇、乙醇、正辛醇、异辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰脲酸酯、N,N′-双(羟乙基)草酰胺、3-硫杂十一烷醇、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷。
1.13.β-(5-叔丁基-4-羟基-3-甲基苯基)丙酸与一元醇或多元醇的酯,例如与下述化合物的酯:甲醇、乙醇、正辛醇、异辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰脲酸酯、N,N′-双(羟乙基)草酰胺、3-硫杂十一烷醇、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷;3,9-双[2-{3-(3-叔丁基-4-羟基-5-甲基苯基)丙酰氧基}-1,1-二甲基乙基]-2,4,8,10-四氧杂螺环[5.5]十一烷。
1.14.β-(3,5-二环己基-4-羟基苯基)丙酸与一元醇或多元醇的酯,例如与下述化合物的酯:甲醇、乙醇、辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰脲酸酯、N,N′-双(羟乙基)草酰胺、3-硫杂十一烷醇、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷。
1.15.3,5-二-叔丁基-4-羟基苯基乙酸与一元醇或多元醇的酯,例如与下述化合物的酯:甲醇、乙醇、辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰脲酸酯、N,N′-双(羟乙基)草酰胺、3-硫杂十一烷醇、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷的酯。
1.16.β-(3,5-二-叔丁基-4-羟基苯基)丙酸的酰胺,例如N,N′-双(3,5-二-叔丁基-4-羟基苯基丙酰基)己二胺、N,N′-双(3,5-二-叔丁基-4-羟基苯基丙酰基)丙二胺、N,N′-双(3,5-二-叔丁基-4-羟基苯基丙酰基)酰肼、N,N′-双[2-(3-[3,5-二-叔丁基-4-羟基苯基]丙酰氧基)乙基]草酰胺。
1.17.抗坏血酸(维生素C)
1.18.含氮抗氧化剂,例如N,N′-二-异丙基-对苯二胺、N,N′-二-仲丁基-对苯二胺、N,N′-双(1,4-二甲基戊基)-对苯二胺、N,N′-双(1-乙基-3-甲基戊基)-对苯二胺、N,N′-双(1-甲基庚基)-对苯二胺、N,N′-二环己基-对苯二胺、N,N′-二苯基-对苯二胺、N,N′-双(2-萘基)-对苯二胺、N-异丙基-N′-苯基-对苯二胺、N-(1,3-二甲基丁基)-N′-苯基-对苯二胺、N-(1-甲基庚基)-N′-苯基-对苯二胺、N-环己基-N′-苯基-对苯二胺、4-(对甲苯氨磺酰基)二苯胺、N,N′-二甲基-N,N′-二-仲丁基-对苯二胺、二苯胺、N-烯丙基二苯胺、4-异丙氧基-二苯胺、N-苯基-1-萘胺、N-(4-叔辛基苯基)-1-萘胺、N-苯基-2-萘胺、辛基化二苯胺,例如p,p′-二-叔辛基二苯胺、4-正丁基氨基酚、4-丁酰基氨基酚、4-壬酰基氨基酚、4-十二烷酰基氨基酚、4-十八烷酰基氨基酚、双(4-甲氧基苯基)胺、2,6-二-叔丁基-4-二甲基氨基甲基酚、2,4′-二氨基二苯甲烷、4,4′-二氨基二苯甲烷、N,N,N′,N′-四甲基-4,4′-二氨基二苯甲烷、1,2-双[(2-甲基苯基)氨基]乙烷、1,2-双(苯基氨基)丙烷、(邻甲苯基)双胍、双[4-(1′,3′-二甲基丁基)苯基]胺、叔辛基化N-苯基-1-萘胺、单-和二烷基化叔丁基/叔辛基二苯胺的混合物、单烷基和二烷基化壬基二苯胺的混合物、单烷基和二烷基化十二烷基二苯胺的混合物、单烷基和二烷基化异丙基/异己基二苯胺的混合物、单烷基和二烷基化叔丁基二苯胺的混合物、2,3-二氢-3,3-二甲基-4H-1,4-苯并噻嗪、吩噻嗪、单烷基和二烷基化叔丁基/叔辛基吩噻嗪的混合物、单烷基和二烷基化叔辛基吩噻嗪的混合物、N-烯丙基吩噻嗪、N,N,N′,N′-四苯基-1,4-二氨基丁-2-烯。
1.19.喹啉衍生物,例如聚合的2,2,4-三甲基-1,2-二氢喹啉、6-乙氧基-2,2,4-三甲基-1,2-二氢喹啉。
2.紫外线吸收剂和光稳定剂
2.1.2-(2′-羟基苯基)苯并三唑,例如2-(2′-羟基-5′-甲基苯基)苯并三唑、2-(3′,5′-二-叔丁基-2′-羟基苯基)苯并三唑、2-(5′-叔丁基-2′-羟基苯基)苯并三唑、2-(2′-羟基-5′-(1,1,3,3-四甲基丁基)苯基)苯并三唑、2-(3′,5′-二-叔丁基-2′-羟基苯基)-5-氯苯并三唑、2-(3′-叔丁基-2′-羟基-5′-甲基苯基)-5-氯苯并三唑、2-(3′-仲丁基-5′-叔丁基-2′-羟基苯基)苯并三唑、2-(2′-羟基-4′-辛氧基苯基)苯并三唑、2-(3′,5′-二-叔戊基-2′-羟基苯基)苯并三唑、2-(3′,5′-双(α,α-二甲基苄基)-2′-羟基苯基)苯并三唑、2-(3′-叔丁基-2′-羟基-5′-(2-辛氧基羰基乙基)苯基)-5-氯苯并三唑、2-(3′-叔丁基-5′-[2-(2-乙基己氧基)羰基乙基]-2′-羟基苯基)-5-氯苯并三唑、2-(3′-叔丁基-2′-羟基-5′-(2-甲氧基羰基乙基)苯基)-5-氯苯并三唑、2-(3′-叔丁基-2′-羟基-5′-(2-甲氧基羰基乙基)苯基)苯并三唑、2-(3′-叔丁基-2′-羟基-5′-(2-辛氧基羰基-乙基)苯基)苯并三唑、2-(3′-叔丁基-5′-[2-(2-乙基己氧基)羰基乙基]-2′-羟基-苯基)苯并三唑、2-(3′-十二烷基-2′-羟基-5′-甲基苯基)苯并三唑、2-(3′-叔丁基-2′-羟基-5′-(2-异辛氧基羰基乙基)苯基苯并三唑、2,2′-亚甲基双[4-(1,1,3,3-四甲基丁基)-6-苯并三唑-2-基酚];2-[3′-叔丁基-5′-(2-甲氧基羰基乙基)-2′-羟基苯基]-2H-苯并三唑与聚乙二醇300的酯交换产物;,其中R=3′-叔丁基-4′-羟基-5′-2H-苯并三唑-2-基苯基、2-[2′-羟基-3′-(α,α-二甲基苄基)-5′-(1,1,3,3-四甲基丁基)苯基]苯并三唑;2-[2′-羟基-3′-(1,1,3,3-四甲基丁基)-5′-(α,α-二甲基苄基)苯基]-苯并三唑。
2.2.2-羟基二苯甲酮,例如4-羟基、4-甲氧基、4-辛氧基、4-癸氧基、4-十二烷氧基、4-苄氧基、4,2′,4′-三羟基和2′-羟基-4,4′-二甲氧基衍生物。
2.3.取代和未取代的苯甲酸的酯,例如水杨酸4-叔丁基苯酯、水杨酸苯酯、水杨酸辛基苯酯、二苯甲酰间苯二酚、双(4-叔丁基苯甲酰基)间苯二酚、苯甲酰间苯二酚、3,5-二-叔丁基-4-羟基苯甲酸2,4-二-叔丁基苯酯、3,5-二-叔丁基-4-羟基苯甲酸十六烷基酯、3,5-二-叔丁基-4-羟基苯甲酸十八烷基酯、3,5-二-叔丁基-4-羟基苯甲酸2-甲基-4,6-二-叔丁基苯酯。
2.4.丙烯酸酯,例如α-氰基-β,β-二苯基丙烯酸乙酯、α-氰基-β,β-二苯基丙烯酸异辛酯、α-碳甲氧基肉桂酸甲酯、α-氰基-β-甲基-对甲氧基肉桂酸甲酯、α-氰基-β-甲基-对甲氧基肉桂酸丁酯、α-碳甲氧基-对甲氧基肉桂酸甲酯和N-(β-碳甲氧基-β-氰基乙烯基)-2-甲基二氢吲哚。
2.5.镍化合物,例如含或不含附加配体(如正丁基胺、三乙醇胺或N-环己基二乙醇胺)的2,2′-硫代双[4-(1,1,3,3-四甲基丁基)酚]的镍络合物,例如1∶1或1∶2络合物,二丁基二硫代氨基甲酸镍、单烷基酯的镍盐,例如甲基或乙基酯的镍盐,4-羟基-3,5-二-叔丁基苄基膦酸的镍盐,酮肟的镍络合物,例如2-羟基-4-甲基苯基十一烷基酮肟的镍络合物,1-苯基-4-月桂酰基-5-羟基吡唑的镍络合物,含或不含附加配体。
2.6.位阻胺,例如双(2,2,6,6-四甲基-4-哌啶基)癸二酸酯、双(2,2,6,6-四甲基-4-哌啶基)丁二酸酯、双(1,2,2,6,6-五甲基-4-哌啶基)癸二酸酯、双(1-辛氧基-2,2,6,6-四甲基-4-哌啶基)癸二酸酯、双(1,2,2,6,6-五甲基-4-哌啶基)正丁基-3,5-二-叔丁基-4-羟基苄基丙二酸酯、1-(2-羟乙基)-2,2,6,6-四甲基-4-羟基哌啶和丁二酸的缩合物、N,N′-双(2,2,6,6-四甲基-4-哌啶基)己二胺和4-叔辛基氨基-2,6-二氯-1,3,5-三嗪的线型或环状缩合物、三(2,2,6,6-四甲基-4-哌啶基)次氮基三乙酸酯、四(2,2,6,6-四甲基-4-哌啶基)-1,2,3,4-丁四羧酸酯、1,1′-(1,2-乙二基)-双(3,3,5,5-四甲基哌嗪酮)、4-苯甲酰基-2,2,6,6-四甲基哌啶、4-硬脂酰氧基-2,2,6,6-四甲基哌啶、双(1,2,2,6,6-五甲基哌啶基)-2-正丁基-2-(2-羟基-3,5-二-叔丁基苄基)丙二酸酯、3-正辛基-7,7,9,9-四甲基-1,3,8-三氮杂螺环[4.5]癸烷-2,4-二酮、双(1-辛氧基-2,2,6,6-四甲基哌啶基)癸二酸酯、双(1-辛氧基-2,2,6,6-四甲基哌啶基)丁二酸酯、N,N′-双(2,2,6,6-四甲基-4-哌啶基)己二胺和4-吗啉并-2,6-二氯-1,3,5-三嗪的线型或环状缩合物、2-氯-4,6-双(4-正丁基氨基-2,2,6,6-四甲基哌啶基)-1,3,5-三嗪和1,2-双(3-氨基丙基氨基)乙烷的缩合物、2-氯-4,6-二-(4-正丁基氨基-1,2,2,6,6-五甲基哌啶基)-1,3,5-三嗪和1,2-双(3-氨基丙基氨基)乙烷的缩合物、8-乙酰基-3-十二烷基-7,7,9,9-四甲基-1,3,8-三氮杂螺环[4.5]癸烷-2,4-二酮、3-十二烷基-1-(2,2,6,6-四甲基-4-哌啶基)吡咯烷-2,5-二酮、3-十二烷基-1-(1,2,2,6,6-五甲基-4-哌啶基)吡咯烷-2,5-二酮、4-十六烷氧基-和4-硬脂酰氧基-2,2,6,6-四甲基哌啶的混合物、N,N′-双(2,2,6,6-四甲基-4-哌啶基)己二胺和4-环己基氨基-2,6-二氯-1,3,5-三嗪的缩合物、1,2-双(3-氨基丙基氨基)乙烷和2,4,6-三氯-1,3,5-三嗪以及4-丁基氨基-2,2,6,6-四甲基哌啶的缩合物(CAS Reg.No.[136504-96-6]);1,6-己二胺和2,4,6-三氯-1,3,5-三嗪以及N,N-二丁胺和4-丁基氨基-2,2,6,6-四甲基哌啶的缩合物(CAS Reg.No.[192268-64-7]);N-(2,2,6,6-四甲基-4-哌啶基)-正十二烷基琥珀酰亚胺、N-(1,2,2,6,6-五甲基-4-哌啶基)-正十二烷基琥珀酰亚胺、2-十一烷基-7,7,9,9-四甲基-1-氧杂-3,8-二氮杂-4-氧代螺环[4,5]癸烷、7,7,9,9-四甲基-2-环十一烷基-1-氧杂-3,8-二氮杂-4-氧代螺环-[4,5]癸烷和表氯醇的反应产物、1,1-双(1,2,2,6,6-五甲基-4-哌啶氧基羰基)-2-(4-甲氧基苯基)乙烯、N,N′-双-甲酰基-N,N′-双(2,2,6,6-四甲基-4-哌啶基)己二胺、4-甲氧基亚甲基丙二酸与1,2,2,6,6-五甲基-4-羟基哌啶的二酯、聚[甲基丙基-3-氧基-4-(2,2,6,6-四甲基-4-哌啶基)]硅氧烷、马来酸酐-α-烯烃共聚物与2,2,6,6-四甲基-4-氨基哌啶或1,2,2,6,6-五甲基-4-氨基哌啶的反应产物、2,4-双[N-(1-环-己氧基-2,2,6,6-四甲基哌啶-4-基)-正丁基氨基]-6-(2-羟乙基)氨基-1,3,5-三嗪、1-(2-羟基-2-甲基丙氧基)-4-十八烷酰氧基-2,2,6,6-四甲基哌啶、5-(2-乙基己酰基)氧基甲基-3,3,5-三甲基-2-吗啉、Sanduvor(Clariant;CAS Reg.No.106917-31-1)、5-(2-乙基己酰基)氧基甲基-3,3,5-三甲基-2-吗啉、2,4-双[(1-环己氧基-2,2,6,6-哌啶-4-基)丁基氨基]-6-氯-s-三嗪与N,N′-双(3-氨基丙基)乙二胺)的反应产物、1,3,5-三(N-环己基-N-(2,2,6,6-四甲基哌嗪-3-酮-4-基)氨基)-s-三嗪、1,3,5-三(N-环己基-N-(1,2,2,6,6-五甲基哌嗪-3-酮-4-基)氨基)-s-三嗪。
2.7.草酰胺,例如4,4′-二辛氧基草酰替苯胺、2,2′-二乙氧基草酰替苯胺、2,2′-二辛氧基-5,5′-二-叔丁基草酰替苯胺、2,2′-双十二烷氧基-5,5′-二-叔丁基草酰替苯胺、2-乙氧基-2′-乙基草酰替苯胺、N,N′-双(3-二甲基氨基丙基)草酰胺、2-乙氧基-5-叔丁基-2′-乙基草酰替苯胺及其与2-乙氧基-2′-乙基-5,4′-二-叔丁基草酰替苯胺的混合物、邻-和对-甲氧基-二取代的草酰替苯胺的混合物和邻-和对-乙氧基二取代的草酰替苯胺的混合物。
2.8.2-(2-羟基苯基)-1,3,5-三嗪,例如2,4,6-三(2-羟基-4-辛氧基苯基)-1,3,5-三嗪、2-(2-羟基-4-辛氧基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-(2,4-二羟基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2,4-双(2-羟基-4-丙氧基苯基)-6-(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-辛氧基苯基)-4,6-双(4-甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-十二烷氧基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-十三烷氧基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-丁氧基丙氧基)苯基]-4,6-双(2,4-二甲基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-辛氧基丙氧基)苯基]-4,6-双(2,4-二甲基)-1,3,5-三嗪、2-[4-(十二烷氧基/十三烷氧基-2-羟基丙氧基)-2-羟基苯基]-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-十二烷氧基丙氧基)苯基]-4,6-双(2,4-二甲基-苯基)-1,3,5-三嗪、2-(2-羟基-4-己氧基)苯基-4,6-二苯基-1,3,5-三嗪、2-(2-羟基-4-甲氧基苯基)-4,6-二苯基-1,3,5-三嗪、2,4,6-三[2-羟基-4-(3-丁氧基-2-羟基丙氧基)苯基]-1,3,5-三嗪、2-(2-羟基苯基)-4-(4-甲氧基苯基)-6-苯基-1,3,5-三嗪、2-{2-羟基-4-[3-(2-乙基己-1-氧基)-2-羟丙氧基]苯基}-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪。
3.金属去活化剂,例如N,N′-二苯基草酰胺、N-水杨醛-N′-水杨酰肼、N,N′-双(水杨酰基)肼、N,N′-双(3,5-二-叔丁基-4-羟基苯基丙酰基)肼、3-水杨酰基氨基-1,2,4-三唑、双(亚苄基)草二酰肼、草酰替苯胺、间苯二酰肼、癸二酰双苯基酰肼、N,N′-二乙烯基己二酰肼、N,N′-双(水杨酰基)草二酰肼、N,N′-双(水杨酰基)硫代丙二酰肼。
4.亚磷酸酯和膦酸酯,例如亚磷酸三苯酯、亚磷酸二苯基烷基酯、亚磷酸苯基二烷基酯、亚磷酸三(壬基苯基)酯、亚磷酸三月桂酯、亚磷酸三(十八烷基)酯、二硬脂基季戊四醇二亚磷酸酯、亚磷酸三(2,4-二-叔丁基苯基)酯、二异癸基季戊四醇二亚磷酸酯、双(2,4-二-叔丁基苯基)季戊四醇二亚磷酸酯、双(2,4-二-枯基苯基)季戊四醇二亚磷酸酯、双(2,6-二-叔丁基-4-甲基苯基)季戊四醇二亚磷酸酯、二异癸氧基季戊四醇二亚磷酸酯、双(2,4-二-叔丁基-6-甲基苯基)季戊四醇二亚磷酸酯、双(2,4,6-三(叔丁基苯基)季戊四醇二亚磷酸酯、三硬脂基山梨糖醇三亚磷酸酯、四(2,4-二-叔丁基苯基)4,4′-亚联苯基二膦酸酯、6-异辛氧基-2,4,8,10-四-叔丁基-12H-二苯并[d,g]-1,3,2-二氧磷杂八环(dioxaphosphocin)、双(2,4-二-叔丁基-6-甲基苯基)甲基亚磷酸酯、双(2,4-二-叔丁基-6-甲基苯基)乙基亚磷酸酯、6-氟-2,4,8,10-四-叔丁基-12-甲基-二苯并[d,g]-1,3,2-二氧磷杂八环、2,2′,2″-次氮基[三乙基三(3,3′,5,5′-四-叔丁基-1,1′-联苯-2,2′-二基)亚磷酸酯]、2-乙基己基(3,3′,5,5′-四-叔丁基-1,1′-联苯-2,2′-二基)亚磷酸酯、5-丁基-5-乙基-2-(2,4,6-三-叔丁基苯氧基)-1,3,2-dioxaphosphirane。
5.羟胺,例如N,N-二苄基羟胺、N,N-二乙基羟胺、N,N-二辛基羟胺、N,N-二月桂基羟胺、N,N-双十四烷基羟胺、N,N-双十六烷基羟胺、N,N-双十八烷基羟胺、N-十六烷基-N-十八烷基羟胺、N-十七烷基-N-十八烷基羟胺、衍生自氢化牛脂胺的N,N-二烷基羟胺。
6.硝酮,例如N-苄基-α-苯基硝酮、N-乙基-α-甲基硝酮、正辛基-α-庚基硝酮、N-月桂基-α-十一烷基硝酮、N-十四烷基-α-十三烷基硝酮、N-十六烷基-α-十五烷基硝酮、N-十八烷基-α-十七烷基硝酮、N-十六烷基-α-十七烷基硝酮、N-十八烷基-α-十五烷基硝酮、N-十七烷基-α-十七烷基硝酮、N-十八烷基-α-十六烷基硝酮、由衍生自氢化牛脂胺的N,N-二烷基羟胺生成的硝酮。
7.硫代增效化合物,例如硫代二丙酸二月桂酯或硫代二丙酸二硬脂酰酯或式IV的化合物
其中
R1是氢、C1-C12烷基、环己基、苯基或苄基,
R2是氢或C1-C4烷基,
且n是0、1或2的数。
8.过氧化物清除剂,例如β-硫代二丙酸的酯,例如月桂基酯、硬脂酰基酯、十四烷基酯或十三烷基酯,巯基苯并咪唑或2-巯基苯并咪唑的锌盐、二丁基二硫代氨基甲酸锌、双十八烷基二硫化物、季戊四醇四(β-十二烷基巯基)丙酸酯。
9.碱性助稳定剂,例如甲胺、聚乙烯基吡咯烷酮、双氰胺、氰脲酸三烯丙酯、脲衍生物、肼衍生物、胺、聚酰胺、聚氨酯、高级脂肪酸的碱金属盐和碱土金属盐,例如硬脂酸钙、硬脂酸锌、山嵛酸镁、硬脂酸镁、蓖麻醇酸钠和棕榈酸钾、焦儿茶酸锑或焦儿茶酸锌。
10.填料和增强剂,例如碳酸钙、硅酸盐、玻璃纤维、玻璃球、滑石、高岭土、云母、硫酸钡、金属氧化物和氢氧化物、炭黑、石墨、木粉,和其它天然产品的粉或纤维,合成纤维。
11.其它添加剂,例如增塑剂、润滑剂、乳化剂、颜料、流变添加剂、催化剂、流动控制剂、荧光增白剂、阻燃剂、抗静电剂和发泡剂。
12.苯并呋喃酮和吲哚酮,例如U.S.4,325,863;U.S.4,338,244;U.S.5,175,312;U.S.5,216,052;U.S.5,252,643;DE-A-4316611;DE-A-4316622;DE-A-4316876;EP-A-0589839;EP-A-0591102或EP-A-1291384中公开的那些,或3-[4-(2-乙酰氧基乙氧基)苯基]-5,7-二-叔丁基苯并呋喃-2-酮、5,7-二-叔丁基-3-[4-(2-硬脂酰氧基乙氧基)苯基]苯并呋喃-2-酮、3,3′-双[5,7-二-叔丁基-3-(4-[2-羟基乙氧基]苯基)苯并呋喃-2-酮]、5,7-二-叔丁基-3-(4-乙氧基苯基)苯并呋喃-2-酮、3-(4-乙酰氧基-3,5-二甲基苯基)-5,7-二-叔丁基苯并呋喃-2-酮、3-(3,5-二甲基-4-新戊酰氧基苯基)-5,7-二-叔丁基苯并呋喃-2-酮、3-(3,4-二甲基苯基)-5,7-二-叔丁基苯并呋喃-2-酮、3-(2,3-二甲基苯基)-5,7-二-叔丁基苯并呋喃-2-酮或3-(2-actyl-5-异辛基苯基)-5-异辛基苯并呋喃-2-酮。
本发明的优选方法包含一种或多种选自由颜料、染料、填料、匀平助剂、分散剂、增塑剂、硫化活化剂、硫化促进剂、硫化剂、电荷控制剂、增粘剂、抗静电剂、金属氧化物、抗氧化剂和光稳定剂(例如酚式抗氧化剂,清单中的项目1.1至1.17,或含氮抗氧化剂,清单中的项目1.18)、有机亚磷酸酯或膦酸酯(清单中的项目4)、硫代增效剂(清单中的项目7)和/或苯并呋喃酮(清单中的项目12)组成的组的组分作为其它添加剂。
优选地,所述组分是环氧化的大豆油和/或2,2,6,6-四甲基哌啶-1-氧基(TEMPO)。后者是自由基。
优选地,式I的化合物与组分(例如环氧化的大豆油)的重量比为99.5∶0.5至10∶90。式I的化合物与2,2,6,6-四甲基哌啶-1-氧基(TEMPO)的重量比为2∶1至1∶2。
基于要配混的橡胶总重量,这些其它添加剂的添加浓度的实例是0.01至10%。
在硫化之前,例如在带有锤的内部混合机(Banbury)中、在混合辊上或在混合挤出机中混合的过程中,将式I的化合物和需要时的其它添加剂,在一步或多步中合并到橡胶中。在添加到橡胶中时,式I的化合物和需要时的其它添加剂也可以是例如以2.5至25重量%的浓度包含它们的母料形式。
所得配混橡胶可以以多种形式使用,例如条带、模制组合物、型材、传送带或轮胎。然后将最终形式硫化(橡胶的交联)。
优选地,橡胶与所述组分的配混在125至200℃、例如150至200℃、最优选在150至160℃进行。
本发明进一步的实施方案是式I化合物的用途,用作在125至200℃下的橡胶配混所用的加工稳定剂。
下述实施例进一步例证本发明。份数或百分比按重量计。
实施例1:二氧化硅填充的混炼胶的制备
配方(见表1):
表1:
橡胶/组分 | 重量份 | 化学类型 | 供应商 |
S-SBR Buna VSL 5025-0 | 75 | 橡胶 | Lanxess |
BR Buna CB 527 T | 25 | 橡胶 | Lanxess |
Ingralen 450 | 33 | 增量油 | Fuchs/Mannheim |
Ultrasil VN3 | 80 | 填料 | Degussa |
氧化锌 | 2.5 | 活化剂 | |
硬脂酸 | 1.0 | 活化剂 | |
Antilux 110 | 1.5 | 蜡 | Lanxess |
在Haake实验室混合器中使用450毫升混合头,以普通方式将这些成分混合。在根据本发明的实施例中,另外加入0.5重量份的加工稳定剂[Irganox 1520(RTM);实施例1b]。混合器温度为125℃,转子转速75rpm,填充系数70%,且总混合时间20分钟。根据相应的ASTM标准测量该基础混合物的门尼粘度MS1+4(100)。结果概括在表2中。较低门尼粘度表明由于较好的加工稳定性而实现的较低氧化交联。
表2
实施例 | 加工稳定剂 | 门尼粘度MS1+4(100) |
1aa) | 无 | 84 |
1bb) | 0.5份Irganox 1520c) | 62 |
参见表9后的脚注解释
实施例2:含硅烷偶联剂的二氧化硅填充的混炼胶的制备
在许多二氧化硅填充混炼胶中使用硅烷偶联剂以改变机械性质,特别是在胎面化合物中。良好的加工稳定性对避免氧化交联而言是必要的,所述氧化交联造成粘度提高和后续的升温。温度控制对避免不合意的“硅烷焦化”而言是非常重要的,所述“硅烷焦化”会由于在二氧化硅和橡胶链之间过早形成化学键而造成进一步的粘度提高。
配方(见表3):
表3:
橡胶/组分 | 重量份 | 化学类型 | 供应商 |
S-SBR Buna VSL 5025-0 | 75 | 橡胶 | Lanxess |
BR Buna CB 527 T | 25 | 橡胶 | Lanxess |
Ingralen 450 | 33 | 增量油 | Fuchs/Mannheim |
Ultrasil VN3 | 80 | 填料 | Degussa |
氧化锌 | 2.5 | 活化剂 | |
硬脂酸 | 1.0 | 活化剂 | |
Antilux 110 | 1.5 | 蜡 | Lanxess |
硅烷69 | 6.0 | 偶联剂 | Degussa |
在Haake实验室混合器中使用450毫升混合头以普通方式混合这些成分。在根据本发明的实施例中,另外加入0.5重量份加工稳定剂[Irganox1520(RTM)]。在对比例2b中,代替Irganox 1520,另外加入2.0重量份Vulkanox 4020(RTM)。混合器温度为125℃,转子转速为75rpm,填充系数为70%,且总混合时间为20分钟。根据相应的ASTM标准测量该基础混合物的门尼粘度MS1+4(100)。结果概括在表4中。较低门尼粘度表明由于较好的加工稳定性而实现的较低氧化交联。
表4:
实施例 | 加工稳定剂 | 门尼粘度MS1+4(100) |
2aa) | 2.0份Vulkanox 4020d) | 70 |
2bb) | 0.5份Irganox 1520c) | 44 |
参见表9后的脚注解释
实施例3:EPDM炭黑母料的制备
为了制造该母料,在带有凸轮叶片转子的Brabender实验室混合器中在180℃和45rpm下将100份EPDM与70份炭黑N 550混合。在混合过程开始时加入加工稳定剂。混合过程中的扭矩提高表明由剪切力、高温和氧造成的氧化交联。诱导时间(即在经过(massing)最小/平衡后直至扭矩升高一Nm的混合时间)是加工稳定性或加工稳定剂体系的性能的良好表征。较长的诱导时间表明较好的稳定性。结果概括在表5中。
表5:
实施例 | 加工稳定剂 | 诱导时间(分钟) |
3aa) | 无 | 0.5 |
3ba) | 1.0%Irganox HP 2225e) | 5.5 |
3cb) | 0.5%Irganox 1520c) | 8.5 |
3db) | 1.0%Irganox 1520c) | >30 |
参见表9后的脚注解释
实施例4:使用优化的加工稳定剂加工受损橡胶
通过后添加抗降解剂,不能大规模地使受损橡胶再生。因此,进行试验以确定在混合过程开始时添加抗老化剂是否可以防止受损橡胶的氧化交联。为此,首先在70℃将商业稳定化的低-顺式聚丁二烯老化最多达3周。通过在Brabender混合器中在150℃和45rpm转子转速下测量诱导时间,测定加工稳定性和加工稳定剂体系的性能。结果概括在表6中。较长的诱导时间表明较好的加工稳定性。
表6:
实施例 | 加工稳定剂 | 诱导时间(分钟) |
4aa) | 无 | 3 |
4ba) | 2.0%Vulkanox 4020d) | 6.6 |
4ca) | 0.3%Irganox 1076i)0.6%Irganox PS 800j) | 5.2 |
4db) | 0.2%Irganox 1520c) | >60 |
参见表9后的脚注解释
实施例5:EPDM炭黑母料的制备
为了制造该母料,在带有凸轮叶片转子的Brabender实验室混合器中在180℃和45rpm下将100份EPDM与70份炭黑N 550混合。在混合过程开始时加入加工稳定剂。在混合过程中由于剪切力、高温和氧而发生橡胶的氧化交联。这造成EPDM炭黑母料的粘度提高。以根据相应ASTM标准的门尼粘度单位MS1+4(100)表示的较低的粘度表明较好的稳定性。结果概括在表7中。
表7:
实施例 | 加工稳定剂 | 门尼粘度MA1+4(100) |
5aa) | 无 | >200 |
5ba) | 1.0%Flectol Hk) | >200 |
5ca) | 1.0%Vulkanox 4020d) | >200 |
5db) | 1.0%EB 51-677l) | 143 |
参见表9后的脚注解释
实施例6:在高混合温度下制备炭黑填充的混炼胶
如果在高温下混合混炼胶,良好的加工稳定性对避免氧化交联而言是必要的,这种氧化交联造成粘度提高和因此在后续制造步骤中造成问题。使用合适的加工稳定剂体系保护了橡胶并减少了粘度的提高。
配方(见表8):
表8:
橡胶/组分 | 重量份 | 化学类型 | 供应商 |
NR SMR CV 60 | 50 | 天然橡胶 | |
BR Buna CB 24 | 50 | 橡胶 | Lanxess |
Ingralen 450 | 5 | 增量油 | Fuchs/Mannheim |
炭黑N 550 | 50 | 填料 | |
氧化锌 | 3.0 | 活化剂 | |
硬脂酸 | 1.0 | 活化剂 |
在Brabender实验室混合器中使用凸轮叶片混合器以普通方式混合这些成分。在根据本发明的实施例中,另外加入1.0重量份加工稳定剂。混合器温度为180℃,转子转速为45rpm,且总混合时间为6分钟。根据相应的ASTM标准测量该基础混合物的门尼粘度MS1+4(100)。较低的门尼粘度表明由于较好的加工稳定性而实现的较低氧化交联。结果概括在表9中。
表9:
实施例 | 加工稳定剂 | 诱导时间(分钟) |
6aa) | 无 | 72 |
6aa) | 1.0%Vulkanox 4020d) | 72 |
6bb) | 1.0%EB 51-667l) | 67 |
6bb) | 0.5%EB 51-667l)0.5%TEMPOm) | 62 |
a)对比例。
b)本发明的实施例。
c)Irganox 1520(RTM)[Ciba Specialty Chemicals Inc.]是式A的化合物
d)Vulkanox 4020(RTM)[Bayer]是式B的4-[1,3-二甲基丁基]氨基二苯基胺
e)Irganox HP 2225(RTM)[Ciba Specialty Chemicals Inc.]是15%的HP 136f)和85%的Irganox B 225[50%的lrgafos 168g)和50%的Irganox1010h)的混合物]的混合物。
f)HP 136(RTM)是3-(3,4-二甲基苯基)-5,7-二-叔丁基苯并呋喃-2-酮和3-(2,3-二甲基苯基)-5,7-二-叔丁基苯并呋喃-2-酮的混合物。
g)lrgafos 168(RTM)是三(2,4-二-叔丁基苯基)亚磷酸酯。
h)Irganox 1010(RTM)是式C的化合物。
i)Irganox 1076(RTM)是式D的化合物。
j)Irganox PS 800(RTM)是式E的化合物。
k)Flectol H(RTM)是聚合的1,2-二氢-2,2,4-三甲基喹啉。
l)EB 51-677是98.25%的IRGANOX 1520(RTM)c)和1.75%的Irgaplast 392(RTM)(其是一种环氧化的大豆油)的混合物
m)TEMPO是2,2,6,6-四甲基哌啶-1-氧基(自由基)。
Claims (7)
1.改进的制备混炼胶的方法,包括在基于橡胶重量的0.1至2%的式I的加工稳定剂存在下在125至200℃将橡胶和组分配混:
其中
R1是氢、C1-C20烷基、苯乙烯基、α-甲基-苯乙烯基或-CH2-S-R3;或被C2-C20链烯基、C3-C20炔基、C5-C9环烷基、苯基或甲苯基取代的C1-C20烷基;
R2是C1-C20烷基或-CH2-S-R3,
R3是C1-C20烷基;被苯基、羟基、氰基、甲酰基、乙酰基或-O-CO-R5取代的C1-C20烷基;C2-C20链烯基、C3-C20炔基、C5-C9环烷基;或被羟基、苯基、4-氯-苯基、2-甲氧基羰基苯基、对甲苯基、1,3-苯并噻唑-2-基、-(CHR5)nCOOR6或-(CHR5)nCONR7R8取代的C5-C9环烷基;
R4是氢或甲基,
R5是氢或C1-C6烷基,
R6是C1-C20烷基;被氧或硫插入的C3-C20烷基;C5-C9环烷基、苯基、苄基或甲苯基,
R7和R8彼此独立地为氢或C1-C6烷基,且
n是1或2。
2.根据权利要求1的方法,其中R3是C6-C18烷基。
3.根据权利要求1的方法,其中
R1是甲基,
R2是-CH2-S-R3,
R3是C8-C12烷基,且
R4是氢。
4.根据权利要求1的方法,其中所述组分选自由颜料、染料、填料、匀平助剂、分散剂、增塑剂、硫化活化剂、硫化促进剂、硫化剂、电荷控制剂、增粘剂、抗静电剂、金属氧化物、抗氧化剂和光稳定剂组成的组。
5.根据权利要求4的方法,其中所述组分是环氧化的大豆油和/或2,2,6,6-四甲基哌啶-1-氧基。
6.根据权利要求1的方法,其中所述配混在150至200℃进行。
7.根据权利要求1的式I的化合物的用途,用作用于在125至200℃的橡胶配混的加工稳定剂。
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Cited By (4)
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CN102942718A (zh) * | 2012-11-29 | 2013-02-27 | 利安隆(天津)化工有限公司 | 用于丁二烯类合成橡胶生产中的复配抗氧化剂及应用 |
CN103030843A (zh) * | 2012-12-27 | 2013-04-10 | 利安隆(天津)化工有限公司 | 用于丁二烯合成橡胶生产用复配抗氧化剂及应用 |
CN103497376A (zh) * | 2013-09-13 | 2014-01-08 | 天津利安隆新材料股份有限公司 | 应用于丁腈胶乳和羧基丁腈胶乳的抗氧化剂及制备方法 |
CN106029765A (zh) * | 2014-02-28 | 2016-10-12 | 埃克森美孚化学专利公司 | 门尼粘度稳定的溴化弹性体 |
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US9309379B2 (en) * | 2008-05-15 | 2016-04-12 | Basf Se | Basic stabilisation systems for emulsion polymerised rubber |
US8980391B2 (en) | 2010-06-25 | 2015-03-17 | Allegiance Corporation | Vulcanization composition having reduced allergenic potential, and elastomeric articles formed therewith |
JP6119132B2 (ja) * | 2012-07-13 | 2017-04-26 | 横浜ゴム株式会社 | ゴム組成物および空気入りタイヤ |
CN106459484B (zh) * | 2014-02-03 | 2019-10-15 | 阿朗新科德国有限责任公司 | 稳定化的橡胶 |
WO2016105931A1 (en) | 2014-12-23 | 2016-06-30 | Bridgestone Americas Tire Operations, Llc | Oil-containing rubber compositions and related methods |
US10179479B2 (en) | 2015-05-19 | 2019-01-15 | Bridgestone Americas Tire Operations, Llc | Plant oil-containing rubber compositions, tread thereof and race tires containing the tread |
US20170029605A1 (en) * | 2015-07-27 | 2017-02-02 | Toyo Tire & Rubber Co., Ltd. | Rubber composition for tire and pneumatic tire |
DE102016213787A1 (de) * | 2016-07-27 | 2018-02-01 | Man Diesel & Turbo Se | Verfahren zum Betreiben eines Kühlsystems eines Schiffs |
CN109890890B (zh) * | 2016-10-26 | 2022-02-22 | 花王株式会社 | 橡胶组合物 |
WO2022146441A1 (en) * | 2020-12-31 | 2022-07-07 | Compagnie Generale Des Etablissements Michelin | Rubber composition with longer lasting antiozonation |
CN115651278B (zh) * | 2022-10-13 | 2023-09-22 | 泰凯英(青岛)专用轮胎技术研究开发有限公司 | 耐磨耐热工程轮胎胎面胶及其制备方法 |
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DE3671241D1 (de) * | 1985-11-13 | 1990-06-21 | Ciba Geigy Ag | Substituierte phenole als stabilisatoren. |
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TW222293B (zh) * | 1991-12-06 | 1994-04-11 | Ciba Geigy Ag | |
CA2194210A1 (en) | 1996-12-31 | 1998-06-30 | Bayer Inc. | Process for making stabilised non-coloured rubber |
TW491833B (en) | 2000-01-10 | 2002-06-21 | Ciba Sc Holding Ag | Improved process for the preparation of mercaptomethylphenols |
WO2005021637A1 (ja) | 2003-09-01 | 2005-03-10 | Zeon Corporation | 共役ジエン系ゴム組成物、その製造方法およびゴム架橋物 |
US7473724B2 (en) * | 2005-02-15 | 2009-01-06 | The Goodyear Tire & Rubber Company | Preparation of silica reinforced polyisoprene-rich rubber composition and tire with component thereof |
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2008
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Cited By (5)
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CN102942718A (zh) * | 2012-11-29 | 2013-02-27 | 利安隆(天津)化工有限公司 | 用于丁二烯类合成橡胶生产中的复配抗氧化剂及应用 |
CN103030843A (zh) * | 2012-12-27 | 2013-04-10 | 利安隆(天津)化工有限公司 | 用于丁二烯合成橡胶生产用复配抗氧化剂及应用 |
CN103497376A (zh) * | 2013-09-13 | 2014-01-08 | 天津利安隆新材料股份有限公司 | 应用于丁腈胶乳和羧基丁腈胶乳的抗氧化剂及制备方法 |
CN106029765A (zh) * | 2014-02-28 | 2016-10-12 | 埃克森美孚化学专利公司 | 门尼粘度稳定的溴化弹性体 |
CN106029765B (zh) * | 2014-02-28 | 2019-09-10 | 埃克森美孚化学专利公司 | 门尼粘度稳定的溴化弹性体 |
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BRPI0808813A2 (pt) | 2016-08-02 |
US8101679B2 (en) | 2012-01-24 |
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JP2010521576A (ja) | 2010-06-24 |
EP2125945A1 (en) | 2009-12-02 |
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