CN86107859A - 取代酚稳定剂 - Google Patents
取代酚稳定剂 Download PDFInfo
- Publication number
- CN86107859A CN86107859A CN86107859.4A CN86107859A CN86107859A CN 86107859 A CN86107859 A CN 86107859A CN 86107859 A CN86107859 A CN 86107859A CN 86107859 A CN86107859 A CN 86107859A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- compound
- tertiary butyl
- methyl
- chemical formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000003381 stabilizer Substances 0.000 title abstract description 4
- 150000002989 phenols Chemical class 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 40
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 239000011347 resin Substances 0.000 claims abstract description 23
- 229920005989 resin Polymers 0.000 claims abstract description 23
- 239000000314 lubricant Substances 0.000 claims abstract description 17
- 239000000126 substance Substances 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000004814 polyurethane Substances 0.000 claims description 5
- 229920002635 polyurethane Polymers 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 2
- 125000005466 alkylenyl group Chemical group 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 4
- 229920001971 elastomer Polymers 0.000 abstract description 2
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 239000000806 elastomer Substances 0.000 abstract 1
- -1 1,1-dimethylbutyl Chemical group 0.000 description 102
- 239000002585 base Substances 0.000 description 31
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 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 13
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 11
- 239000000654 additive Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 8
- 239000000499 gel Substances 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 7
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
- 230000032683 aging Effects 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000001939 inductive effect Effects 0.000 description 6
- 229910052759 nickel Inorganic materials 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- JEFSTMHERNSDBC-UHFFFAOYSA-N 1,2-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC=CCC1(C)O JEFSTMHERNSDBC-UHFFFAOYSA-N 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000010705 motor oil Substances 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 4
- FEXBEKLLSUWSIM-UHFFFAOYSA-N 2-Butyl-4-methylphenol Chemical group CCCCC1=CC(C)=CC=C1O FEXBEKLLSUWSIM-UHFFFAOYSA-N 0.000 description 4
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 4
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229940059574 pentaerithrityl Drugs 0.000 description 4
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 230000006641 stabilisation Effects 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 4
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 4
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 244000043261 Hevea brasiliensis Species 0.000 description 3
- 239000013032 Hydrocarbon resin Substances 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- LOEUCBBZEHMJQN-UHFFFAOYSA-N hydrazine;oxalic acid Chemical class NN.OC(=O)C(O)=O LOEUCBBZEHMJQN-UHFFFAOYSA-N 0.000 description 3
- 229920006270 hydrocarbon resin Polymers 0.000 description 3
- 239000004816 latex Substances 0.000 description 3
- 229920000126 latex Polymers 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 229920003052 natural elastomer Polymers 0.000 description 3
- 229920001194 natural rubber Polymers 0.000 description 3
- 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 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 150000003008 phosphonic acid esters Chemical class 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
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 3
- 229940117958 vinyl acetate Drugs 0.000 description 3
- HQEPZWYPQQKFLU-UHFFFAOYSA-N (2,6-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC(O)=C1C(=O)C1=CC=CC=C1 HQEPZWYPQQKFLU-UHFFFAOYSA-N 0.000 description 2
- GOZHNJTXLALKRL-UHFFFAOYSA-N (5-benzoyl-2,4-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(O)=C(C(=O)C=2C=CC=CC=2)C=C1C(=O)C1=CC=CC=C1 GOZHNJTXLALKRL-UHFFFAOYSA-N 0.000 description 2
- MQQKTNDBASEZSD-UHFFFAOYSA-N 1-(octadecyldisulfanyl)octadecane Chemical compound CCCCCCCCCCCCCCCCCCSSCCCCCCCCCCCCCCCCCC MQQKTNDBASEZSD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- STHGLRYNMROMHZ-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)-11-methyl-3-(8-methylnonyl)dodecane-1,3-diol Chemical compound C(CCCCCCC(C)C)C(O)(C(CO)(CO)CO)CCCCCCCC(C)C STHGLRYNMROMHZ-UHFFFAOYSA-N 0.000 description 2
- OCSIKZYSDOXRPA-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)-3-octadecylhenicosane-1,3-diol dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O.C(CCCCCCCCCCCCCCCCC)C(O)(C(CO)(CO)CO)CCCCCCCCCCCCCCCCCC OCSIKZYSDOXRPA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 2
- ZELZXAOKZAWHME-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-2-oxoacetic acid Chemical compound OCCOC(=O)C(O)=O ZELZXAOKZAWHME-UHFFFAOYSA-N 0.000 description 2
- PMRTXCQELXDQEH-UHFFFAOYSA-N 2-[carboxymethyl-[2-oxo-2-(2,2,6,6-tetramethylpiperidin-4-yl)oxyethyl]amino]acetic acid Chemical compound CC1(C)CC(OC(=O)CN(CC(O)=O)CC(O)=O)CC(C)(C)N1 PMRTXCQELXDQEH-UHFFFAOYSA-N 0.000 description 2
- HHPDFYDITNAMAM-UHFFFAOYSA-N 2-[cyclohexyl(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(CCO)C1CCCCC1 HHPDFYDITNAMAM-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- WBJWXIQDBDZMAW-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(O)=CC=C21 WBJWXIQDBDZMAW-UHFFFAOYSA-N 0.000 description 2
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical class CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 2
- BKZXZGWHTRCFPX-UHFFFAOYSA-N 2-tert-butyl-6-methylphenol Chemical class CC1=CC=CC(C(C)(C)C)=C1O BKZXZGWHTRCFPX-UHFFFAOYSA-N 0.000 description 2
- JJNGVLXTDWITLL-UHFFFAOYSA-N 5-(N-hydroxy-C-undecylcarbonimidoyl)-2-methylphenol Chemical compound C(CCCCCCCCCCC)(C1=CC(=C(C=C1)C)O)=NO JJNGVLXTDWITLL-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- OGBVRMYSNSKIEF-UHFFFAOYSA-N Benzylphosphonic acid Chemical compound OP(O)(=O)CC1=CC=CC=C1 OGBVRMYSNSKIEF-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- YHOKOCFZNYBCKX-UHFFFAOYSA-N C(CCCCCCCCCCC)P(O)(O)O Chemical class C(CCCCCCCCCCC)P(O)(O)O YHOKOCFZNYBCKX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- 239000004594 Masterbatch (MB) Substances 0.000 description 2
- IWGBGUINMSOOKP-UHFFFAOYSA-N OC1=C(C(=O)CCCCCCCCCCC)C=NN1C1=CC=CC=C1 Chemical class OC1=C(C(=O)CCCCCCCCCCC)C=NN1C1=CC=CC=C1 IWGBGUINMSOOKP-UHFFFAOYSA-N 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- DJSTVBDVHQIQFO-UHFFFAOYSA-N P1(OC2=C(C=CC=C2)OP(OC2=C(C=CC=C2)O1)=O)=O Chemical class P1(OC2=C(C=CC=C2)OP(OC2=C(C=CC=C2)O1)=O)=O DJSTVBDVHQIQFO-UHFFFAOYSA-N 0.000 description 2
- 239000004902 Softening Agent Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- YSFVDVZOGIPGEU-UHFFFAOYSA-N [Sb].OC1=CC=CC=C1O Chemical compound [Sb].OC1=CC=CC=C1O YSFVDVZOGIPGEU-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- PYHXGXCGESYPCW-UHFFFAOYSA-N alpha-phenylbenzeneacetic acid Natural products C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- 239000010425 asbestos Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- IRSWRCCZAUZIMU-UHFFFAOYSA-N benzene-1,2-diol;tin Chemical compound [Sn].OC1=CC=CC=C1O IRSWRCCZAUZIMU-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 125000006487 butyl benzyl group Chemical group 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- CCRCUPLGCSFEDV-UHFFFAOYSA-N cinnamic acid methyl ester Natural products COC(=O)C=CC1=CC=CC=C1 CCRCUPLGCSFEDV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000010586 diagram Methods 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 229960000452 diethylstilbestrol Drugs 0.000 description 2
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000007323 disproportionation reaction Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
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- 229910052725 zinc Inorganic materials 0.000 description 1
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Abstract
新的组合物,该组合物含有高弹体或粘性树脂及至少一种化学式I的化合物
式中R1,R2和R3的定义见权利要求1,化学式I的某些化合物是新的并且适合作为润滑剂的稳定剂。新的组合物适宜制备胶片或粘合剂。
Description
本发明涉及了含有取代的双(烷基硫代甲基)酚作为稳定的组合物,并涉及了新的双(烷基硫代甲基)酚。
含有烷基硫代甲基的酚作为稳定剂是众所周知的,例如,美国专利说明书3660352描述了2,4,6-三烷基-双(3,5-烷基硫代甲基)酚在聚合物和高弹体中作为抗氧化剂的应用。另外,在美国专利说明书3227667中也指出了2,6-双(烷氧基羰基亚烷基硫代甲基)-4-烷基酚作为聚烯烃的抗氧化剂。
根据英国专利说明书1184533,3,4-双(烷基硫代甲基)-3,6-二烷基酚能够作为有机聚合物以及合成油的稳定剂使用。
有些物质是需要有效稳定剂的,这些物质对热、氧化或诱导光线降解是敏感的。
因此,本发明涉及了一种含有高弹体或粘性树脂及至少一种化学式Ⅰ化合物的组合物
式中
R1是C1~C8烷基或C5~C12环烷基,
彼此独立的两个R2基是由1个或2个羟基或由-OCO-R4,-CO-OR5或-CO-NR5R6未取代或取代的C1~C18烷基,或是苯基或苄基,
R3是氢或甲基,但须当R1不是甲基时,R3才是甲基,
R4是C1~C17烷基,C2~C8链烯基或化学式为Ⅰa的基
m是0,1或2,
彼此独立的两个基R1和R1所表明的基团相同,
R5是能够被-O-,-S-或-NR′-所间断的C1~C20烷基,和R6是氢或是R5表明基团的一种。
作为C1~C8烷基的R1和R′的例子有甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基,正戊基,异戊基、正己基、1,1-二甲基丁基,正庚基,正辛基或2-乙基己基。优选的R1和R′是C1~C4烷基,特别是甲基、乙基,异丙基或叔丁基,最好是甲基或叔丁基。
作为C5~C12环烷基的R1和R′的例子有环戊基、环己基、环庚基、环辛基或环十二烷基。优选的R1和R′是C5~C8环烷基,最好是环己基。
作为C1~C18烷基R2的例子,除R1所表明的基团之外还有正壬基,正癸基,1,1,3,3-四甲基丁基、1,1,3,3-四甲基己基,正十一烷基、正十二烷基,1,1,3,3,5,5-六甲基己基,正十四烷基、正十六烷基或正十八烷基,优选的R2是C4~C18烷基,最好是C8~C18烷基,例如正辛基或正十二烷基。
作为C1~C18烷基的R2可用1个或2个羟基取代。这种R2基的例子有:2-羟乙基、2-羟丙基、2-羟丁基、2-羟十二烷基,2-羟十六烷基,2-羟十八烷基或2,3-二羟丙基,优选的R2基是2-羟乙基。
作为C1~C17烷基的R4的例子是R2所表示基团的一种或甲基,而C1~C12烷基,例如甲基,乙基、正丙基、异丙基,正丁基、叔丁基,正己基,正辛基、2-乙基己基或正十二烷基是优选的基团。
作为C2~C8链烯基的R4的例子有:乙烯基,丙烯基、甲代烯丙基,3-丁烯基,4-戊基烯基、5-己烯基,7-辛烯基,9-癸烯基或11-十二碳烯基,R4最好是乙烯基或丙烯基。
作为化学式Ⅰa基的R4可以是4-羟基-3,5-二甲基苯基、4-羟基-3,5-二叔丁基苯基,4-羟基-3,5-二甲基苄基、4-羟基-3,5-二-叔丁基苄基或4-羟基-3,5-二甲基苯乙基,而4-羟基-3,5-二-叔丁基苄基是优选基。
作为C1~C20烷基的R5或R6的例子是R2所表示基团的一种或甲基、十八烷基或二十烷基,而甲基、乙基、正己基、正辛基或正十二烷基是优选的基。
作为用-O-,-S-,或-NR′-间断的C1~C20烷基的R5或R6的例子是3-氧杂丁基、3-氧杂戊基,3,6-二氧杂庚基,3,6,9-三氧杂癸基,3,6,9,12-四氧杂十三烷基、3,6,9,12,15-五氧杂十六烷基,3,6,9,12,15,18-六氧杂十九基、3-硫杂丁基,3-氮杂丁基,3-甲基-3-氮杂戊基、3-乙基-3-氮杂戊基,3-甲基-3-氮杂-6-氧杂庚基,而3-氧杂戊基或3-氮杂丁基是优选基。
优选的组合物是那些含有高弹体和至少一种化学式Ⅰ化合物的组合物。
特别优选的组合物是含有高弹体和至少一种化学式Ⅰ化合物的组合物,其中化学式Ⅰ中彼此独立的两个R2基是C2~C18烷基,这些烷基是由1个或2个羟基或-OCO-R4,-CO-OR5或-CO-NR5R6所未取代或取代的基,并且R4、R5和R6的定义同上。
更优先选用的组合物是那些含有高弹体或粘性树脂及化学式Ⅰ中的R是C1~C4烷基,最好是甲基或叔丁基的组合物。
最优先选用的组合物是那些含有高弹体或粘性树脂以及化学式Ⅰ中的R2是C4~C18烷基,-CH2CH2-OH,-CH2CH2-O-CO-R4,-CH2-CO-R5或-CH2CH2-CO-R5的组合物,同时R4和R5的定义同上。特别优选的R2是C4~C18烷基或-CH2-COO-R6,同时R6的定义同上。最佳的R2是C4~C18烷基。
有代表性的化学式Ⅰ化合物的例子是下面所列的物质:
2,4-双(2′-羟基乙基硫代甲基)-6-甲酚,
2,4-双(2′,3′-二羟丙基硫代甲基)-3,6-二甲酚,
2,4-双(2′-乙酰基氧代乙基硫代甲基)-3,6-二甲酚,
2,4-双(2′-正癸酰基氧代乙基硫代甲基)-6-甲酚,
2,4-双(正-辛基硫代甲基)-6-甲酚,
2,4-双(叔-辛基硫代甲基)-6-甲酚*1,
2,4-双(叔十二烷基硫代甲基)-6-甲酚*2,
2,4-双(苄基硫代甲基)-6-甲酚,
2,4-双(苯基硫代甲基)-3-甲基-6-叔-丁基酚,
2,4-双(2′-乙基己基氧代羰基甲基硫代甲基)-6-甲酚,
2,4-双(正-十八烷基氧代羰基甲基硫代甲基)-3,6-二甲酚,
2,4-双(2′-(2″-乙基己基氧代羰基)乙基硫代甲基]-3-甲基-6-叔丁基酚。
*1:叔-辛基是1,1,3,3-四甲基丁基
*2:叔-十二烷基是含有1,1,3,3,5,5-六甲基己基和1,1,4,6,6-五甲基庚-4-基的混合物。
本发明的组合物可含高弹体物质的例子有:
1.聚二烯,例如聚丁二烯,聚异戊二烯或氯丁橡胶;嵌段共聚物,例如苯乙烯/丁二烯/苯乙烯,苯乙烯/异戊二烯/苯乙烯或丙烯腈/丁二烯共聚物。
2.单烯属烃和二烯属烃相互聚合或与其它乙烯型单体聚合的共聚物,例如,乙烯/烷基丙烯酸酯共聚物,乙烯/烷基异丁烯酸酯共聚物,乙烯/乙烯基乙酸酯共聚物和乙烯与丙烯和二烯的三元共聚物,例如,己二烯、二聚环戊二烯或亚乙基-降冰片烯。
3.含囟聚合物,例如氯丁橡胶,氯化橡胶,氯化聚乙烯或氯磺化聚乙烯,表氯醇均聚物和表氯醇共聚物、三氟氯乙烯共聚物,含囟乙烯系化合物的聚合物,例如,聚偏二氯乙烯,聚偏氟乙烯,及其它们的共聚物,例如乙烯基氯/亚乙烯基二氯,乙烯基氯/乙烯基乙酸酯或亚乙烯二氯/乙烯基乙酸酯。
4.由聚醚,聚酯和具有末端羟基在一侧,脂族或芳族聚异氰酸酯在另一侧的聚丁二烯衍生的聚氨基甲酸乙酯、和它们的母体。
5.天然橡胶。
6.上述聚合物的混合物(高聚混合物)
7.天然橡胶或合成橡胶的水乳浊液,例如天然橡胶乳或羧化的苯乙烯/丁二烯共聚物的胶乳。
这些高弹体可呈胶乳的形式存在并能够呈胶乳的形式稳定。
较佳的组合物是那些含有作为高弹体的聚二烯的组合物,例如聚丁二烯橡胶,含囟聚合物例如聚偏氟乙烯,或聚氨基甲酸乙酯。
本发明的组合物以高弹体的重量为准,通常含有0.01~10%(重),最好含有0.05~5.0%(重)的化学式Ⅰ稳定剂。化学式Ⅰ稳定剂的混合物也可以使用。
无论有或没有溶剂的后续蒸发作用,用工艺中常用的方法,在模制前或模制期间,把化学式Ⅰ的物质和其它可选择的添加剂掺入到高弹体中是能够实施的,也可以使用向聚合物中溶解或分散化合物的方法。化学式Ⅰ的化合物还可以加入到呈母炼胶形式的将被稳定的塑料中,该母炼胶中含有所说的化合物浓度为2.5-25%(重)。
本发明组合物可以含有粘性树脂物质的例子有:
-天然松香树脂(松脂)例如松香、木松香、浮油松香;
-松香树脂的衍生物,例如丙三醇酯、季戊四醇酯,每中酯均可以氢化或非氢化、歧化或非歧化;
-合成的C5-或C9-烃类树脂;
-茚树脂、甲基茚树脂、苯并呋喃-茚树脂;
-萜烯树脂;
-甲基苯乙烯树脂;
-酚树脂;
-其它粘合剂如石油沥青或沥青;
-上述树脂的混合物;
-上述树脂的水乳浊液。
较佳的组合物是那些含有合成的C5-或C9-烃类树脂,松香树脂或松香树脂衍生物的组合物。
基于粘性树脂,粘性树脂的组合物通常含有0.01~10%(重),最好为0.03~3.0%(重)的化学式Ⅰ稳定剂,化学式Ⅰ稳定剂的混合物也可以使用。
用本工艺中常用的方法,在制造或改型之前、之中、之后把化学式Ⅰ的化合物掺入粘性树脂中是可以实施的。
本发明的组合物能够呈各种形式应用。例如,薄膜,纤丝,螺条,模制组合物、型材(profile),或作为漆、粘合剂或油灰的粘合剂。
化学式Ⅰ的某些化合物是已知的。
而化学式Ⅰ的新化合物便构成了本发明的一个目的。所说的新化合物具有化学式Ⅱ的结构。
所以本发明还涉及了化学式Ⅱ的化合物:
其中两个彼此独立的R7基是C8~C18烷基,该C8~C18烷基是由1个或2个羟基或由-OCO-R4,-CO-OR5或-CO-NR5R6所未取代或取代的基,而R4和R5和R6定义同上。
上面化学式Ⅰ中R2所表明的典型基和优选基也适用于化学式Ⅱ中的R7。上面关于R4、R5和R6表明的基团也同样适于于化学式Ⅱ中的R4、R5和R6。
那些含有两个互相独立的R7基,并且R7基是未被取代的C8~C18烷基的化学式Ⅱ的化合物是优选化合物。
化学式Ⅱ的最佳化合物是式中两个彼此独立的R7基相同并且是C8~C12烷基。
化学式Ⅰ和Ⅱ的已知化合物和新化合物可用已知的方法制备,例如英国专利说明书1184533和美国专利说明书3227677中叙述的制备方法。所有原材料都是已知化合物并且能够用已知方法制备。某些原材料是市场上买得到的。
另外,本发明还涉及一种制备化学式Ⅱ化合物的方法,该方法包括用化学式为R7-SH的硫醇与2,4-双(二甲基氨甲基)-6-甲酚反应。
本发明化学式Ⅱ的酚除了适合稳定高弹体和粘性树脂外,还适合于稳定基于矿物油或合成油的润滑剂。特别是车用机油。
适宜的润滑剂对本专业技术人员来说是熟知的,并且在《润滑剂手册》(Huthig Verlag,Heidelberg,1974)中有叙述。
因此,本发明还涉及了化学式Ⅱ化合物的应用,即用于稳定润滑剂,使润滑剂具有抗氧、热、光和高能辐射的能力。
此外,本发明涉及了含有润滑剂和至少一种化学式Ⅱ化合物的组合物。
基于润滑剂,本发明化学式Ⅱ的酚通常添加浓度为0.01~10%(重),基于润滑剂较佳的添加量为0.05~5.0%(重量),最佳量为0.1~2.0%(重)。
化学式Ⅱ酚的混合物也可以使用。
含有化学式Ⅱ酚的本发明润滑剂组成还可以含有其它添加剂,这些添加剂的加入可以改善润滑剂的某些工作特性,例如,其它的抗氧化剂、金属钝化剂、防锈剂、粘度指数增进剂、降凝剂、分散剂/表面活性剂和抗磨添加剂。
在润滑剂中可以和化学式Ⅱ酚一起使用的其它添加剂例子有:
1.抗氧化剂:
1.1.烷基化的一元酚,例如
2.6-二-叔丁基-4-甲酚
2-叔丁基-4,6-二甲酚
2.6-二-叔丁基-4-乙酚
2.6-二-叔丁基-4-正丁酚
2.6-二-叔丁基-4-异丁酚
2.6-二环戊基-4-甲酚
2-(α-甲基环己基-4,6-二甲酚
2.6-二(十八烷基)-4-甲酚
2,4,6-三环己基苯酚
2,6-二-叔丁基-4-甲氧基甲酚
1.2烷基化的对苯二酚,例如
2.6-二-叔丁基-4-甲氧基苯酚
2.5-二-叔丁基对苯二酚
2.5-二-叔戊基对苯二酚
2.6-二苯基-4-十八烷基氧代苯酚
1.3,羟基化硫代二苯基醚
2,2′-硫代双(6-叔丁基-4-甲酚)
2.2′-硫代双(4-辛基苯酚)
4,4′-硫代双(6-叔丁基-3-甲酚)
4.4-硫代双(6-叔丁基-2-甲酚)
1.4,亚烷基双酚,例如
2.2′-亚甲基双(6-叔丁基-4-甲酚)
2.2′-亚甲基双(6-叔丁基-4-乙酚)
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-甲酚)
2.2′-亚乙基双(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-甲苄基)-4-壬基酚]
2.2′-亚甲基双[6-(α,α-二甲苄基)-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-甲酚)
1.1-双(5-叔丁基-4-羟基-2-甲苯基)丁烷.
2.6-双(3-叔丁基-5-甲基-2-羟苄基)-4-甲酚
1.1.3-三(5-叔丁基-4-羟基-2-甲苯基)丁烷
1.1-双(5-叔丁基-4-羟基-2-甲苯基)-3-正十二烷巯基丁烷
乙二醇双[3,3-双(3′-叔丁基-4′-羟基苯基)丁酸]
双(3-叔丁基-4-羟基-5-甲苯基)二聚环戊二烯
双[2-(3′-叔丁基-2′-羟基-5′-甲苄基)-6-叔丁基-4-甲苯基]对苯二酸酯
1.5.苄基化合物,例如
1.3,5三(3.5-二-叔丁基-4-羟基苄基)-2,4,6-三甲苯
双(3,5-二叔丁基-4-羟基苄基)硫醚.
异辛基3,5-二-叔丁基-4-羟苄基巯基乙酸酯。
双(4-叔丁基-3-羟基-2.6-二甲苄基)二硫酚对苯二酸酯。
1,3,5-三[3,5-二-叔丁基-4-羟苄基)异氰脲酸酯
1,3,5-三(4-叔丁基-3-羟基-2,6-二甲苄基)异氰脲酸酯
二(十八烷基)-3,5-二-叔丁基-4-羟苄基基膦酸酯
单乙基3,5-二-叔丁基-4-羟基苄基膦酸钙盐
1.6.酰氨基酚,例如
4-羟基月桂酸的酰苯胺
4-羟基硬脂酸的酰苯胺
2.4-双(辛基巯基)-6-(3,5-二-叔丁基-4-羟基苯胺基)-均-三嗪
辛基N-(3,5-二-叔丁基-4-羟苯基)氨基甲酸酯.
1.7β-(3.5-二叔丁基-4-羟苯基)丙酸与一元醇或多元醇形成的酯,一元醇与多元醇的例子有:
甲醇 二甘醇
十八醇 三甘醇
1.6-己二醇 季戊四醇
新戊二醇 三(羟乙基)异氰脲酸酯
硫代二甘醇 双(羟乙基)草酸
肼
1.8β-(5-叔丁基-4-羟基-3-甲苯基)丙酸与-元醇或多元醇形成的酯,一元醇或多元醇的例子有:
甲醇 二甘醇
十八醇 三甘醇
1,6-己二醇 季戊四醇
新戊二醇 三(羟乙基)异氰脲酸酯
硫代二甘醇 双(羟乙基)草酸
肼
1,9,β-(3,5-二-叔丁基-4-羟苯基)丙酸的酰胺,例如
N,N′-双(3,5-二-叔丁基-4-羟苯基丙酰)六亚甲基二胺
N,N′-双(3,5-二-叔丁基-4-羟苯基丙酰)亚丙基二胺
N,N′-双(3,5-二叔丁基-4-羟苯基丙酰)肼
2.紫外吸收剂和光稳定剂:
2.1 2-(2′羟苯基)苯并***,例如5′-甲基、3′,5′-二-叔丁基、5′-(1,1,3,3-四甲基丁基),5-氯代-3′,5′-二-叔丁基、5-氯-3′-叔丁基-5′-甲基、3′-仲丁基-5′-叔丁基、4′-辛氧基、3′,5′-二-叔戊基和3′,5′-双(α,α-二甲苄基)的衍生物。
2.2 2-羟基二苯酮,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 取代的或者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、联苯甲酰间苯二酚,双(4-叔丁基苯甲酰)间苯二酚、苯甲酰间苯二酚、2,4-二-叔丁基苯基3,5-二-叔丁基-4-羟基苯甲酸酯和十六烷基3,5-二-叔丁基-4-羟基苯甲酸酯。
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-甲酯基肉桂酸甲酯、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-甲酯基-对-甲氧基肉桂酸甲酯和N-(β-甲酯基-β-氰基乙烯基)-2-甲基二氢吲哚。
2.5 镍化合物,例如2,2′-硫代双〔4-(1,1,3,3-四甲基丁基)酚〕的镍配合物,这种配合物可以1∶1或1∶2比例与或不与其它附加配位体,如正丁胺,三乙胺或N-环己基二乙醇胺配合,二丁基二硫代氨基甲酸 镍,4-羟基-3,5-二-叔丁苄基膦酸一元烷基酯如甲基或乙基酯的镍盐,酮肟如2-羟基-4-甲苯基十一烷基酮肟的镍配合物,可与或不与附加配位体配合的1-苯基-4-月桂酰-5-羟基吡唑的镍配合物。
2.6 空间位阻胺,例如双(2,2,6,6-四甲基哌啶基)癸二酸酯,双(1,2,2,6,6-五甲基哌啶基)癸二酸酯,双(1,2,2,6,6-五甲基哌啶基)正丁基-3,5-二-叔丁基-4-羟苄基丙二酸酯,1-羟乙基-2,2,6,6-四甲基-4-羟基哌啶和丁二酸的缩合产物,N,N′-(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-叔辛基氨基-2,6-二氯-1,3,5-均-三嗪的缩合产物,三重(2,2,6,6-四甲基-4-哌啶基)次氮基三乙酸酯。四重(2,2,6,6-四甲基-4-哌啶基)-1,2,3,4-丁烷四羧酸酯,1,1′-(1,2-乙烷二基)双(3,3,5,5-四甲基哌嗪酮)。
2,7 草酸肼,例如4,4′-二辛基氧代N,N′-草酰二苯胺,2,2′-二辛基氧代-5,5′-二-叔丁基N,N′-草酰二苯胺,2,2′-二(十二烷基)氧代-5,5′-二叔丁j3N,N′-草酰二苯胺,2-乙氧基-2′-乙基N,N′-草酰二苯胺,N,N′-双(3-二甲基氨丙基)草酰胺,2-乙氧基-5-叔丁基-2′-乙基N,N′-草酰二苯胺和它与2-乙氧基-2′-乙基-5,4′-二-叔丁基N,N′-草酰二苯胺及邻位和对位甲氧基双取代N,N′-草酰二苯胺混合物和邻位-和对-乙氧基双取代N,N′-草酰二苯胺混合物。
3.金属钝化剂,例如N,N′-二苯基草酸肼,N-水杨醛-N′-水杨酰肼,N,N′-双(水杨酰)肼,N,N′-双(3,5-二-叔丁基-4-羟基苯丙酰)肼,3-水杨酰氨基-1,2,4-***,双(亚苄基)草酸二酰肼。
4.亚磷酸酯和膦酸酯,例如三苯基磷酸酯,二苯基烷基亚磷酸酯,苯基二烷基亚磷酸酯,三(壬基苯基)亚磷酸酯,三月桂基亚磷酸酯,三(十八烷基)亚磷酸酯,二硬脂酰季戊四醇二亚磷酸酯,三(2,4-二-叔丁苯基)亚磷酸酯,二异癸基季戊四醇二亚磷酸酯,双(2,4-二-叔丁苯基)季戊四醇二亚磷酸酯,三硬脂酰山梨糖醇三亚磷酸酯,四(2,4-二-叔丁基苯基)4,4′-二亚苯基二膦酸酯,3,9-双(2,4-二-叔丁基苯氧基)-2,4,8,10-四噁-3,9-二磷杂螺〔5,5〕十一烷。
5.过氧化物清除剂,例如β-硫代二丙酸的酯,例如月桂基,硬脂酰,十四烷基或十三烷基酯,硫基苯并咪唑或2-巯基苯并咪唑的锌盐,二丁基二硫代氨基甲酸锌,二(十八烷基)二硫化物,季戊四醇四(β-十二烷基巯基)丙酸酯。
6.酰胺稳定剂,例如与碘化物和/或磷化合物结合的铜盐和二价锰的盐。
7.碱性共稳定剂,例如,三聚氰胺,聚乙烯吡咯烷酮,双氰胺,三烯丙基氰尿酸酯,尿素衍生物,肼衍生物,胺,酰胺,聚氨基甲酸乙酯,高级脂肪酸的碱金属盐和土金属盐,例如,硬脂酸钙,硬脂酸锌,硬脂酸镁,蓖麻醇酸酯钠和棕榈酸钾,邻苯二酚锑或邻苯二酚锡。
8.成核剂,例如4-叔丁基苯甲酸,己二酸,二苯基乙酸。
9.填料和增强剂,例如碳酸钙,硅酸盐,玻璃纤维,石棉,滑石,高岭土,云母,硫酸钡,金属氧化物和金属氢氧化物,炭黑,石墨。
10.其它添加剂,例如增塑剂,润滑剂,乳化剂,颜料,荧光增白剂,阻燃剂,抗静电剂,发泡剂。
实际上,包含有高弹体或粘性树脂和化学式Ⅰ酚的本发明组合物也可以含有其它的添加剂,这些添加剂的例子有:
1.抗氧化剂:
抗氧化剂的例子在上面所列的润滑剂的附加添加剂中可以找到。
2.紫外吸收剂和光稳定剂:
2.1 2-(2′-羟苯基)苯并***,例如5′-甲基、3′,5′-叔丁基、5′-叔丁基、5′-(1,1,3,3-四甲基丁基)、5-氯-3′,5′-二-叔丁基、5-氯-3′-叔丁基-5′-甲基、3′-仲丁基-5′-叔丁基、4′-辛氧基、3′,5′-二-叔戊基和3′,5′-双(α,α-二甲苄基)的衍生物。
2.2 2-羟基二苯酮,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 取代的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,联苯甲酰间苯二酚,双(4-叔丁基苯甲酰)间苯二酚,苯甲酰间苯二酚,2,4-二-叔丁基苯基3,5-二-叔丁基-4-羟基苯甲酸酯和十六烷基3,5-二-叔丁基-4-羟基苯甲酸酯。
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-甲酯基肉桂酸甲酯,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-酯基-对-甲氧基肉桂酸甲酯和N-(β-甲酯基-β-氰基乙烯基)-2-甲基二氢吲哚。
2.5 镍化合物,例如2,2′-硫代双〔4-(1,1,3,3-四甲基丁基)酚〕的镍配合物,这种配合物可以1∶1或1∶2比例与或不与其它附加配位体,如正丁胺,三乙胺或N-环己基二乙醇胺配合,二丁基二氨荒酸镍,4-羟基-3,5-二-叔丁苄基膦酸一元烷基酯如甲基或乙基酯的镍盐,酮肟如2-羟基-4-甲苯基十一烷基酮肟的镍配合物,可与或不与附加配位体配合的1-苯基-4-月桂酰-5-羟基吡唑的镍配合物。
2.6 空间位阻胺,例如双〔2,2,6,6-四甲基哌啶基)癸二酸酯,双(1,2,2,6,6-五甲基哌啶基)癸二酸酯,双(1,2,2,6,6-五甲基哌啶基)正丁基-3,5-二-叔丁基-4-羟苄基丙二酸酯,1-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′-(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-叔辛基氨基-2,6-二氯-1,3,5-均-三嗪的缩合产物,三(2,2,6,6-四甲基-4-哌啶基)次氮基三乙酸酯,四(2,2,6,6,6-四甲基-4-哌啶基)-1,2,3,4-丁烷四羧酸酯,1,1′-(1,2-乙烷二基)双(3,3,5,5-四甲基哌嗪酮)。
2.7 草酸肼,例如4,4′-二辛基氧代N,N′-草酰二苯胺,2,2′-二辛基氧代-5,5′-二-叔丁基N,N′-草酰二苯胺,2,2′-二(十二烷基)氧代-5,5′-二-叔丁基N,N′-草酰二苯胺,2-乙氧基-2′-乙基N,N′-草酰二苯胺,N,N′-双(3-二甲基氨丙基)草酰胺,2-乙氧基-5-叔丁基-2′-乙基N,N′-草酰二苯胺和它与2-乙氧基-2′乙基-5,4′-二-叔丁基N,N′-草酰二苯胺及邻位和对位甲氧基双取代N,N′-草酰二苯胺混合物和邻位一和对一乙氧基双取代N,N′-草酰二苯胺混合物的混合物。
3.亚磷酸酯和膦酸酯,例如三苯基亚磷酸酯,二苯基烷基亚磷酸酯,苯基二烷基亚磷酸酯,三(壬基苯基)亚磷酸酯,三月桂基亚磷酸酯,三(十八烷基)亚磷酸酯,二硬脂酰季戊四醇二亚磷酸酯,三(2,4-二-叔丁苯基)亚磷酸酯,二异癸基季戊四醇二亚磷酸酯,双(2,4-二-叔丁苯基)季戊四醇二亚磷酸酯,三硬脂酰山梨糖醇三亚磷酸酯,四(2,4)-二-叔丁基苯基)4,4′-二亚苯基二膦酸酯,3,9-双(2,4-二-叔丁基苯氧基)-2,4,8,10-四噁-3,9-二磷杂螺〔5,5〕十一烷。
4.过氧化物清除剂,例如β-硫代二丙酸的酯,例如月桂基,硬脂酰,十四烷基或十三烷基酯,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,三(十八烷基)二硫化物,季戊四醇四(β-十二烷基巯基)丙酸酯。
5.酰胺稳定剂,例如与碘化物和/或磷化合物结合的铜盐和二价锰的盐。
6.碱性共稳定剂,例如,三聚氰胺,聚乙烯吡咯烷酮,双氰胺,三烯丙基氰尿酸酯,尿素衍生物,肼衍生物,胺,酰胺,聚氨基甲酸乙酯,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,硬脂酸镁,蓖麻醇酸酯钠和棕榈酸钾,邻苯二酚锑或邻苯二酚锡。
7.成核剂,例如4-叔丁基苯甲酸,己二酸,二苯基乙酸。
8.填料和增强剂,例如碳酸钙,硅酸盐,玻璃纤维,石棉,滑石,高岭土,云母,硫酸钡,金属氧化物和金属氢氧化物,炭黑,石墨。
9.其它添加剂,例如增塑剂,润滑剂,乳化剂,颜料,荧光增白剂,阻燃剂,抗静电剂,发泡剂,蜡,油,有机溶剂。
本发明将用下列实施例加以详细说明。在这些实施例中、即在说明书的剩余部分和在权利要求书中,份数和百分比都以重量计。
准备例
例1:
2,4-双(正-辛基硫代甲基)-6-甲酚(化合物Ⅰ)的制备:
将160.74克(0.72摩尔)2,4-双(二甲基氨乙基)-6-甲酚和210.65克(1.44摩尔)正辛烷硫醇在装有搅拌器和多级蛇管冷凝器的仪器中在150℃下混合36小时,然后在53.2巴压力下用二甲基胺连续抽取。得到291.6克(95%)的黄色油,粗产品通过硅胶柱进行柱色谱法分离得到无色细状形式的钝2,4-双(正辛基硫代甲基)-6-甲酚。
分析值:
计算:C:70.69%,实测:C:70.85%
H:10.44% H:10.42%
S:15.09% S:15.11%
H核磁共振(CDCl3;100MH2;基于TMS=0,S=单峰的输入数据δ〔ppm〕:对Ar-CH2S在3.77(S)和3.6(S)有特征信号。
化学式(Ⅰ)的下列化合物可以类似的方法制备。
化合物 R1R2R 物理数据
化合物2 CH3n-C12H25H 熔点28℃
化合物3 CH3n-C12H25CH3熔点43℃
化合物4 C(CH3)3n-C12H25CH3熔点40℃
化合物5 CH3n-C8H17CH3液体
90-100℃
化合物7 CH3 H 液体
化合物9 CH3-CH2CH2-OH H 液体
化合物10 CH3-C(CH3)2-CH2-C(CH3)2- H 液体
-CH2-C(CH3)3
化合物11 CH3-C(CH3)2-CH2-C(CH3)3H 液体
应用例
对例1的化合物1~4做它们的稳定作用试验。
例2:
聚丁二烯橡胶的稳定作用(加热老化)
用0.4%的2,6-二-叔丁基-对-甲酚预先稳定过的聚丁二烯100克同0.25%的将被试验的稳定剂一起在两辊轧制机上在50℃时均匀混合6分钟。在80℃时由轧制成的薄板压制成10毫米厚的试样。其它的试样用同样的方式制备只是不加稳定剂。
把试样放到80℃的循环空气炉中进行加热老化处理来试验本发明的组合物。确定试样稳定性的标准是在加热老化期间所形成的不希望凝胶的含量。凝胶含量按下列方式测定:
在室温下将1克的聚丁二烯溶解于100毫升的甲苯中,放置一夜。溶液通过玻璃过滤漏斗(微孔孔径00)过滤,然后将滤液蒸发至干。
凝胶含量使用下面公式计算:
凝胶= (E-A)/(E) ×100(%)
E=重量-总重量(1克)
A=蒸发后残余物的重量
诱导期后凝胶含量迅速增加。试样显示凝胶含量为2%的时间被认为是诱导期的适宜定义。为测量这个诱导期,应周期地测定凝胶含量。
结果见表1
表1
稳定剂 直到凝胶含量为2%的诱导期
(以天为单位)
无 21
化合物2 77
化合物3 84
化合物4 56
例3:
聚丁二烯橡胶的稳定作用〔布雷本登(Brabender)〕
用0.4%的2.6-二-叔丁基-对-甲酚预先稳定的聚丁二烯100份和0.25%的将被试验的稳定剂一起在布雷本登塑性计上在160℃时以60转/分的转速捏和30分钟。由流体的转矩测量诱导期,即最小转矩后转矩在数分钟内增长到100毫泊(mp)时的捏和时间。
结果见表2
表2
稳定剂 诱导期(以分钟为单位)
无 8
化合物1 >30
化合物2 23
化合物3 23.5
化合物4 26
例4
TFOUT试验(薄膜氧气摄取试验)
这个试验是对矿物油(ASTM D2272)的旋转弹内氧化试验的一种改良方案,C.S.KU和S.M.HSU在《润滑工程》卷40(2),第75~83页,(1984)上发表的关于车用曲轴箱润滑剂评价的薄膜氧气摄取试验对TFOUT试验有一个精确的描述。该试验油是以矿物油为基础的车用机油。该车用机油中二硫代磷酸锌(0.75%,锌含量0.06%,以车用机油为基准)的含量为常用量的一半;这个变化使得将要试验的稳定剂的潜在效应能被观察到。
例1的化合物1在上面描述的车用机油中是在有2%的水、并且有液态氧化物及作为催化剂的硝化汽油馏分(4%浓度)和作为附加催化剂的液态环烷酸金属盐(4%浓度)的存在下进行试验的。所使用的水和两种液态催化剂用国家标准局(NBS)的标准参考物第1817号分析鉴定。当在压力/时间图中出现向下倾斜特征时便完成了该试验。列在下表中的结果表明了直到在压力/时间图中有一向下倾斜时的时间(以分钟计)。
时间长的周期表示稳定剂的活性好。
稳定剂的浓度(以油为基准):0.5%。
表3
稳定剂 直到压力有一下降特征的时间
(以分钟计)
无 85
化合物1 134
例5
氢化的C5-烃类树脂的稳定作用(加热老化)
预先用0.15%-二-叔丁基-对-甲酚稳定的树脂50克在170℃的玻璃烧瓶中熔化并且搅拌,然后与0.1%的化合物1混合15分钟。将热熔体注入铝皿和陪替氏培养皿中,凝固树脂状物的厚度层在铝皿中大约是15毫米,在陪替氏培养皿中是1毫米。通过把试样(树脂状物质)放到170℃的循环空气炉中加热老化试验本发明的组合物。确定试样稳定性的标准是在加热老化期间出现不希望的变色作用。用下面方法测定变色作用:
a)对1毫米试样的情况:泛黄度指数(Yellowness Index)按照ASTDM1925-70和
b)对15毫米试样的情况:加纳尔颜色值(Gardner Colour value)按照DIN6161。
值越高表明变色作用越大(这对泛黄度指数和加纳尔颜色值均适用)。
结果见表4
表4
稳定剂 170℃时,数小时后 170℃,数小时后的
的泛黄度,指数 加纳尔颜色值
0 12 30 0 12 30
无 3 86 126 1 5 9
化合物1 3 6 12 1 1-2 3-4
Claims (12)
2、根据权利要求1的方法,该方法包括把至少一种化学式Ⅰ的化合物掺入高弹体中。
3、根据权利要求2的方法,其中两个彼此独立的R2基是被或未被1个或2个羟基或-OCO-R4,-CO-OR5或-CO-NR5R6取代的C2~C18烷基,或它们是苄基或苯基,而R4、R5和R6与它们在权利要求1中的定义相同。
4、根据权利要求1的方法,其中R1是C1~C4烷基。
5、根据权利要求2的方法,其中R是甲基或叔丁基。
6、根据权利要求1的方法,其中R2是C4~C18烷基,-CH2-CH2-OH,-CH2CH3-O-CO-R4,-CH2-CO-R5或-CH2CH2-COR5基团或苄基或苯基,同时R4和R5的定义同它们在权利要求1中定义相同。
7、根据权利要求6的方法,其中R2是C4~C18烷基。
8、根据权利要求1的方法,其中高弹体是聚二烯,含囟聚合物或聚氨基甲酸乙酯。
9、根据权利要求1的方法,该方法包括把基于高弹体或粘性树脂为0.05~5.0%重量的化学式Ⅰ的稳定剂掺入高弹体或粘性树脂中。
11、根据权利要求10的方法,其中彼此独立的两个R7基是未取代的C8~C18烷基。
12、制备稳定组合物的方法,该方法包括把至少一种根据权利要求11所述的化学式Ⅱ的化合物掺入到润滑剂中。
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-
1986
- 1986-11-07 DE DE8686810511T patent/DE3671241D1/de not_active Expired - Lifetime
- 1986-11-07 EP EP86810511A patent/EP0224442B1/de not_active Expired - Lifetime
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- 1986-11-10 CA CA000522557A patent/CA1289147C/en not_active Expired - Lifetime
- 1986-11-11 KR KR1019860009485A patent/KR910005429B1/ko not_active IP Right Cessation
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- 1986-11-13 JP JP61270830A patent/JPH0825990B2/ja not_active Expired - Lifetime
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KR870005035A (ko) | 1987-06-04 |
AU6517186A (en) | 1987-05-21 |
CS816386A2 (en) | 1990-07-12 |
ES2014433B3 (es) | 1990-07-16 |
BR8605596A (pt) | 1987-08-18 |
CN1023123C (zh) | 1993-12-15 |
MX9202733A (es) | 1992-06-30 |
EP0224442A1 (de) | 1987-06-03 |
CA1289147C (en) | 1991-09-17 |
JPS62114955A (ja) | 1987-05-26 |
AU599059B2 (en) | 1990-07-12 |
EP0224442B1 (de) | 1990-05-16 |
US4857572A (en) | 1989-08-15 |
CN1040364A (zh) | 1990-03-14 |
CN1026107C (zh) | 1994-10-05 |
CS273623B2 (en) | 1991-03-12 |
SU1526582A3 (ru) | 1989-11-30 |
DE3671241D1 (de) | 1990-06-21 |
HK13794A (en) | 1994-03-04 |
SG95092G (en) | 1992-12-04 |
KR910005429B1 (ko) | 1991-07-29 |
JPH0825990B2 (ja) | 1996-03-13 |
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