KR100274361B1 - 디티오인산 유도체, 이를 함유하는 조성물 및 윤활 첨가제로서의 용도 - Google Patents
디티오인산 유도체, 이를 함유하는 조성물 및 윤활 첨가제로서의 용도 Download PDFInfo
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- KR100274361B1 KR100274361B1 KR1019930009979A KR930009979A KR100274361B1 KR 100274361 B1 KR100274361 B1 KR 100274361B1 KR 1019930009979 A KR1019930009979 A KR 1019930009979A KR 930009979 A KR930009979 A KR 930009979A KR 100274361 B1 KR100274361 B1 KR 100274361B1
- Authority
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- South Korea
- Prior art keywords
- tert
- butyl
- bis
- compounds
- general formula
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- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 title description 5
- 239000003879 lubricant additive Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 239000000203 mixture Substances 0.000 claims abstract description 31
- 239000012530 fluid Substances 0.000 claims abstract description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 230000001050 lubricating effect Effects 0.000 claims abstract description 7
- 125000005037 alkyl phenyl group Chemical group 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
- 239000000314 lubricant Substances 0.000 claims description 27
- 239000007788 liquid Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 5
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 239000006078 metal deactivator Substances 0.000 claims description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
- 239000005069 Extreme pressure additive Substances 0.000 claims description 2
- 239000007866 anti-wear additive Substances 0.000 claims description 2
- 239000010705 motor oil Substances 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 abstract description 10
- -1 3-heptyl Chemical group 0.000 description 45
- 150000002148 esters Chemical class 0.000 description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 7
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 229910019142 PO4 Inorganic materials 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
- 235000021317 phosphate Nutrition 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 4
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 4
- LRUDIIUSNGCQKF-UHFFFAOYSA-N 5-methyl-1H-benzotriazole Chemical compound C1=C(C)C=CC2=NNN=C21 LRUDIIUSNGCQKF-UHFFFAOYSA-N 0.000 description 4
- CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- XUQNLOIVFHUMTR-UHFFFAOYSA-N 2-[[2-hydroxy-5-nonyl-3-(1-phenylethyl)phenyl]methyl]-4-nonyl-6-(1-phenylethyl)phenol Chemical compound OC=1C(C(C)C=2C=CC=CC=2)=CC(CCCCCCCCC)=CC=1CC(C=1O)=CC(CCCCCCCCC)=CC=1C(C)C1=CC=CC=C1 XUQNLOIVFHUMTR-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 150000001408 amides Chemical class 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
- 239000003925 fat Substances 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- FPQJEXTVQZHURJ-UHFFFAOYSA-N n,n'-bis(2-hydroxyethyl)oxamide Chemical compound OCCNC(=O)C(=O)NCCO FPQJEXTVQZHURJ-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZQMPWXFHAUDENN-UHFFFAOYSA-N 1,2-bis[(2-methylphenyl)amino]ethane Natural products CC1=CC=CC=C1NCCNC1=CC=CC=C1C ZQMPWXFHAUDENN-UHFFFAOYSA-N 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 2
- WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 description 2
- QSZMLDPPGQRTQY-UHFFFAOYSA-N 3-[(3,5-ditert-butyl-4-hydroxyphenyl)methoxy]-3-oxopropanoic acid Chemical compound CC(C)(C)C1=CC(COC(=O)CC(O)=O)=CC(C(C)(C)C)=C1O QSZMLDPPGQRTQY-UHFFFAOYSA-N 0.000 description 2
- VAMBUGIXOVLJEA-UHFFFAOYSA-N 4-(butylamino)phenol Chemical compound CCCCNC1=CC=C(O)C=C1 VAMBUGIXOVLJEA-UHFFFAOYSA-N 0.000 description 2
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 2
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetonamine Chemical compound CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000010775 animal oil Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical compound C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
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- 229920001577 copolymer Polymers 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- 229920000193 polymethacrylate Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- FKFOHTUAFNQANW-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl) octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FKFOHTUAFNQANW-UHFFFAOYSA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- 150000000178 1,2,4-triazoles Chemical class 0.000 description 1
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- NRKKTPXKEYHVCZ-UHFFFAOYSA-N 1-(1-butoxyethyl)-1,2,4-triazole Chemical compound CCCCOC(C)N1C=NC=N1 NRKKTPXKEYHVCZ-UHFFFAOYSA-N 0.000 description 1
- KJGWDJYJHOBAHB-UHFFFAOYSA-N 1-(1-butoxyethyl)benzotriazole Chemical compound C1=CC=C2N(C(C)OCCCC)N=NC2=C1 KJGWDJYJHOBAHB-UHFFFAOYSA-N 0.000 description 1
- KTTREBBQQKBBPI-UHFFFAOYSA-N 1-(3,5-ditert-butyl-4-hydroxyphenyl)nonadecylphosphonic acid Chemical compound CCCCCCCCCCCCCCCCCCC(P(O)(O)=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 KTTREBBQQKBBPI-UHFFFAOYSA-N 0.000 description 1
- KSYAJTVGOSTFLK-UHFFFAOYSA-N 1-(nonoxymethyl)benzotriazole Chemical compound C1=CC=C2N(COCCCCCCCCC)N=NC2=C1 KSYAJTVGOSTFLK-UHFFFAOYSA-N 0.000 description 1
- VMDYMJSKWCVEEB-UHFFFAOYSA-N 1-[3,5-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyl]-1,3,5-triazinan-1-yl]-3-(3,5-ditert-butyl-4-hydroxyphenyl)propan-1-one Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)N2CN(CN(C2)C(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 VMDYMJSKWCVEEB-UHFFFAOYSA-N 0.000 description 1
- IQYDSMJRFWLGKA-UHFFFAOYSA-N 1-[bis(2-hydroxyethyl)amino]-3-(4-nonylphenoxy)propan-2-ol Chemical compound CCCCCCCCCC1=CC=C(OCC(O)CN(CCO)CCO)C=C1 IQYDSMJRFWLGKA-UHFFFAOYSA-N 0.000 description 1
- PIDRVLYMNGNSPO-UHFFFAOYSA-N 1-methyl-2-[(1-methylimidazol-2-yl)-octoxymethyl]imidazole Chemical compound N=1C=CN(C)C=1C(OCCCCCCCC)C1=NC=CN1C PIDRVLYMNGNSPO-UHFFFAOYSA-N 0.000 description 1
- BBRHQNMMUUMVDE-UHFFFAOYSA-N 1-n,2-n-diphenylpropane-1,2-diamine Chemical compound C=1C=CC=CC=1NC(C)CNC1=CC=CC=C1 BBRHQNMMUUMVDE-UHFFFAOYSA-N 0.000 description 1
- HRURMTZJRSHLAV-UHFFFAOYSA-N 1-n,4-n-bis(1,4-dimethylcyclohexa-2,4-dien-1-yl)benzene-1,4-diamine Chemical compound C1=CC(C)=CCC1(C)NC(C=C1)=CC=C1NC1(C)C=CC(C)=CC1 HRURMTZJRSHLAV-UHFFFAOYSA-N 0.000 description 1
- KDLIPGJLQQTGKY-UHFFFAOYSA-N 1-n,4-n-bis(2-methylpropyl)benzene-1,4-diamine Chemical compound CC(C)CNC1=CC=C(NCC(C)C)C=C1 KDLIPGJLQQTGKY-UHFFFAOYSA-N 0.000 description 1
- JUHXTONDLXIGGK-UHFFFAOYSA-N 1-n,4-n-bis(5-methylheptan-3-yl)benzene-1,4-diamine Chemical compound CCC(C)CC(CC)NC1=CC=C(NC(CC)CC(C)CC)C=C1 JUHXTONDLXIGGK-UHFFFAOYSA-N 0.000 description 1
- APTGHASZJUAUCP-UHFFFAOYSA-N 1-n,4-n-di(octan-2-yl)benzene-1,4-diamine Chemical compound CCCCCCC(C)NC1=CC=C(NC(C)CCCCCC)C=C1 APTGHASZJUAUCP-UHFFFAOYSA-N 0.000 description 1
- PWNBRRGFUVBTQG-UHFFFAOYSA-N 1-n,4-n-di(propan-2-yl)benzene-1,4-diamine Chemical compound CC(C)NC1=CC=C(NC(C)C)C=C1 PWNBRRGFUVBTQG-UHFFFAOYSA-N 0.000 description 1
- AIMXDOGPMWDCDF-UHFFFAOYSA-N 1-n,4-n-dicyclohexylbenzene-1,4-diamine Chemical compound C1CCCCC1NC(C=C1)=CC=C1NC1CCCCC1 AIMXDOGPMWDCDF-UHFFFAOYSA-N 0.000 description 1
- VETPHHXZEJAYOB-UHFFFAOYSA-N 1-n,4-n-dinaphthalen-2-ylbenzene-1,4-diamine Chemical compound C1=CC=CC2=CC(NC=3C=CC(NC=4C=C5C=CC=CC5=CC=4)=CC=3)=CC=C21 VETPHHXZEJAYOB-UHFFFAOYSA-N 0.000 description 1
- ZRMMVODKVLXCBB-UHFFFAOYSA-N 1-n-cyclohexyl-4-n-phenylbenzene-1,4-diamine Chemical compound C1CCCCC1NC(C=C1)=CC=C1NC1=CC=CC=C1 ZRMMVODKVLXCBB-UHFFFAOYSA-N 0.000 description 1
- KEXRSLVRFLEMHJ-UHFFFAOYSA-N 1-o,4-o-bis[(4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)methyl] benzene-1,4-dicarbothioate Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1COC(=S)C1=CC=C(C(=S)OCC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C=C1 KEXRSLVRFLEMHJ-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- GOWRNPDLTMZRBO-UHFFFAOYSA-N 1-tert-butylsulfanyl-3-(3-tert-butylsulfanyl-2-hydroxypropyl)sulfanylpropan-2-ol Chemical class CC(C)(C)SCC(O)CSCC(O)CSC(C)(C)C GOWRNPDLTMZRBO-UHFFFAOYSA-N 0.000 description 1
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- 239000010466 nut oil Substances 0.000 description 1
- 235000019488 nut oil Nutrition 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- NTTIENRNNNJCHQ-UHFFFAOYSA-N octyl n-(3,5-ditert-butyl-4-hydroxyphenyl)carbamate Chemical compound CCCCCCCCOC(=O)NC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NTTIENRNNNJCHQ-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- OTYNBGDFCPCPOU-UHFFFAOYSA-N phosphane sulfane Chemical compound S.P[H] OTYNBGDFCPCPOU-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000005642 phosphothioate group Chemical group 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008171 pumpkin seed oil Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 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 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical class C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008170 walnut oil Substances 0.000 description 1
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Abstract
하기 일반식(Ⅰ)의 화합물이 기재되어 있다.
상기식에서,
R1및 R2는 서로 독립해서 C3-C18알킬, C5-C12시클로알킬, C5-C6시클로알킬메틸, C9-C10비시클로알킬메틸, C9-C10트리시클로알킬메틸, 페닐, C7-C24알킬페닐이거나 또는 서로 합쳐져서이며,
R3은 수소 또는 메틸이고,
A는이고,
R4는 수소 또는 C1-C6알킬이며, 또
R5는 5- 또는 6-원 포화 헤테로고리이고,
R6은 수소 또는 메틸이며,
n은 1 내지 11의 정수이고 또
m은 0 내지 4의 정수임.
이들 화합물은 윤활 조성물, 작동액 및 가공액에 대한 첨가제로 사용하는데 특히 적합하다.
Description
본 발명은 디티오인산 유도체, 그의 윤활제 첨가제로서의 용도 및 이들을 함유하는 윤활 조성물, 작동액 및 가공액에 관한 것이다.
흑연과 같은 고체 윤활제와 조합하여 (티오)포스페이트를 사용하는 것은 알려져 있었다(EPO-A-O 214 434호).
고온 윤활 첨가제도 또한 공지되어 있고, 즉 하기 일반식의 화합물이 공지되어 있다(EP-A-O 267 875호):
(RIVX)nP(=Y)(ZRV)3-n
상기식에서, X, Y 및 Z는 서로 독립해서 0 또는 S이고 또 RIV및 RV는 중간에 -O-, -S- 또는 -CO-O-를 포함할 수 있는 C1-C12알킬이다.
윤활제에 대한 인-황 첨가제는 현재 아연 디알킬 디티오포스페이트가 널리 퍼져 있다. 그러나 연소 엔진의 상태는 바람직하게는 재 함량이 적은, 즉 금속 함량이 가능한한 적은 윤활 첨가제를 필요로 한다.
놀랍게도 하기 일반식(Ⅰ)의 화합물은 저온에서 매우 양호한 내마모 보호 특성을 부여한다는 것이 밝혀졌다. 이 화합물은 아연을 전혀 함유하지 않는데, 즉 이들은 현재의 요건을 만족하고, 액체이므로 윤활 조성물과 관련하여 취급하기 용이하다.
따라서, 본 발명은 하기 일반식(Ⅰ)의 화합물에 관한 것이다.
상기식에서,
R1및 R2는 서로 독립해서 C3-C18알킬, C5-C12시클로알킬, C5-C6시클로알킬메틸, C9-C10비시클로알킬메틸, C9-C10트리시클로알킬메틸, 페닐, C7-C24알킬페닐이거나 또는 서로 합쳐져서이며,
R3은 수소 또는 메틸이고,
A는또는 -CH2[CH(OH)]mCH2OH, 이고,
R4는 수소 또는 C1-C6알킬이며, 또
R5는 5- 또는 6-원 포화 헤테로고리이고,
R6은 수소 또는 메틸이며,
n은 1 내지 11의 정수이고 또
m은 0 내지 4의 정수임.
상기 일반식에서 C3-C18알킬로 정의된 R1및 R2는 측쇄 또는 직쇄 라디칼이다. 상세한 예는 프로필, 이소프로필, n-부틸, 이소부틸, 삼차부틸, 펜틸, 이소펜틸, 헥실, 헵틸, 3-헵틸, 옥틸, 2-에틸헥실, 노닐, 데실, 운데실, 도데실, 트리데실, 테트라데실, 펜타데실, 헥사데실, 헵타데실, 옥타데실, 2-에틸부틸, 1-메틸펜틸, 1,3-디메틸부틸, 1,1,3,3-테트라메틸부틸, 1-메틸헥실, 이소헵틸, 1-메틸헵틸, 1,1,3-트리메틸헥실 또는 1-메틸운데실이다.
C5-C12시클로알킬로 정의된 R1및 R2는 전형적으로 시클로펜틸, 시클로헥실, 시클로헵틸, 시클로옥틸 또는 시클로도데실이다. 시클로펜틸 및 시클로헥실이 바람직하다. 시클로헥실이 가장 바람직하다.
C5-C6시클로알킬메틸로 정의된 R1및 R2는 시클로펜틸메틸을 의미하는 것으로 보고, 바람직하게는 시클로헥실메틸이다.
C9-C10비시클로알킬메틸로 정의된 R1및 R2는 전형적으로 데칼리닐메틸이다. C9-C10트리시클로알킬메틸로 정의된 R1및 R2는 바람직하게는 하기 구조식의 기가 바람직하다.
5- 또는 6-원 헤테로고리로 정의된 R5는 피페리디노, 피롤리디노, 피페라지노, 모르폴리노, 피리미디노 또는 테트라히드로푸릴, 바람직하게는 2-테트라히드로푸릴이다.
R1및 R2가 서로 독립해서 C3-C18알킬, C5-C6시클로알킬 또는 C7-C18알킬페닐이고, R5는 테트라히드로푸릴이며, n은 1 내지 6이고 또 m이 0 내지 2인 화합물이 바람직하다.
R1및 R2는 가장 바람직하게는 동일하다. R3은 바람직하게는 수소이다.
본 발명은 또한
a) 윤활제, 가공액 또는 작동액, 및
b) 바람직한 조성물을 형성하는 바람직한 상기 인용 화합물인 한개 이상의 일반식(Ⅰ)의 화합물을 포함하는 조성물에 관한 것이다.
본 발명의 조성물에 함유된 윤활제, 가공액 또는 작동액은 열, 기계적 응력(특히 전단력에 의해 유도됨) 또는 화학적 시약(특히 대기 산소)의 작용하에서 용이하게 다소 분해될 수 있다.
일반식(Ⅰ)의 화합물은 그러한 영향으로 부터 보호하는 작용을 하며 또 0.01 내지 10중량%, 전형적으로 0.05 내지 5중량%, 바람직하게는 0.05 내지 3중량%, 가장 바람직하게는 0.1 내지 2중량%의 양으로 신규 조성물에 존재하는 것이 편리하다. 신규 조성물은 한개 또는 그 이상의 이들 화합물을 함유하며, 또 중량%는 상기 화합물의 전체량에 기준한 것이다. 이론치의 기준은 일반식(Ⅰ)의 화합물을 제외한 윤활제, 가공액 또는 작동액의 전체 중량이다.
본 발명은 또한 윤활제, 작동액 및 가공액에 대한 첨가제, 특히 극압 및 내마모보조제로서 뿐만 아니라 마찰 개질제로서 일반식(Ⅰ)의 화합물의 용도에 관한 것이다.
이러한 용도는 윤활제, 작동액 및 가공액의 성능 특성을 향상시키는 방법을 포함한다. 신규 용도는 윤활될 금속 부분을 기계적 마모로 부터 보호(내마모 보호작용)하는 것을 포함한다.
적합한 윤활제, 작동액 및 가공액은 광물유 또는 합성유 또는 그의 혼합물에 기초로한다. 윤활제는 당해 업자에게 공지되어 있고 또 관련 문헌, 그중에서도 Dieter Klamann, "Schmierstoffe und verwandte Produkte"(Lubricants and Related Products)(Verlag Chemie, Weinheim, 1982), in Schewe-kobek, "Das Schmiermittel-Taschenbuch"(Handbook of Lubricants)(Dr. Alfred Hthig-Verlag, Heidelberg, 1974) 및 "Ullmanns Enzyklodie der technischen Chemie"(Ullmann's Encyclopedia of Industrial Chemisthy), Vol. 13, 85 내지 94페이지(Verlag Chemie, Weinheim, 1977)에 기재되어 있다.
윤활제는 바람직하게는 오일 및 광물유로 부터 전형적으로 유도된 지방이다. 오일이 바람직하다.
본 발명을 실행하는데 사용하기 적합한 윤활제 그룹은 식물유 또는 동물유, 지방, 탤로우 및 왁스 또는 이들의 상호 혼합물 또는 이들과 상기 언급한 광물유 또는 합성유와의 혼합물을 포함한다. 식물유 및 동물유, 지방, 탤로우 및 왁스는 전형적으로 야자너트유, 야자유, 올리브유, 사탕수수 오일, 평지유, 아마인유, 땅콩유, 간장콩유, 목화씨 기름, 해바라기씨 기름, 호박씨 기름, 코코넛유, 옥수수 기름, 피마자유, 호두 기름 및 이들의 혼합물, 어유, 죽인 동물의 탤로우, 예컨대 소고기 탤로우, 우족 및 뼈 기름 뿐만 아니라 그의 개질, 에폭시화 및 술폭시화된 형태, 전형적으로 에폭시화된 간장콩 오일을 포함한다.
광물유는 특히 탄화수소 화합물을 기준한다.
합성 윤활제는 전형적으로 지방족 또는 방향족 카르복실레이트, 중합체성 에스테르, 폴리알킬렌 옥사이드, 포스페이트, 폴리-α-올레핀 또는 실리콘에 기본하거나, 이가 산과 일가 알코올의 디에스테르, 전형적으로 디옥틸 세바케이트 또는 디노닐 아디페이트를 기본하거나, 트리메틸올프로판과 일가 산 또는 산 혼합물과의 트리에스테르, 예컨대 트리메틸올프로판 트리펠라고네이트, 트리메틸올프로판 트리카프릴레이트 또는 그의 혼합물을 기본하거나, 펜타에리트리톨과 일가산 또는 이러한 산 혼합물과의 테트라에스테르, 전형적으로 펜타에리트리톨 테트라카프릴레이트를 기본하거나 또는 일가 또는 이가 산과 다가 알코올과의 복합 에스테르, 예컨대 트리메틸올프로판과 카프닐산 및 세바신산 또는 이들의 혼합물과의 복합 에스테르를 기본한다. 특히 적합한 윤활제는 광물유 이외에 전형적으로 폴리-α-올레핀, 에스테르 기제 윤활제, 포스페이트, 글리콜, 폴리글리콜 및 폴리알킬렌 클리콜 및 이들과 물의 혼합물이다.
가공액 및 작동액은 상술한 바와 같이 윤활제와 관련된 동일한 물질로 부터 제조될 수 있다. 흔히 이들은 물 또는 다른 액체중의 유제이다.
본 발명의 윤활제 조성물은 연소 엔진, 전형적으로 오토(Otto) 사이클, 디젤, 2행정, 반켈 또는 오비탈 유형의 엔진에 의해 구동되는 자동차에 대해 사용될 수 있다.
일반식(Ⅰ)의 화합물은 윤활제, 가공액 및 작동액에 쉽게 용해되므로 특히 윤활제, 가공액 및 작동액에 대한 첨가제로서 사용하기 적합하다. 놀랄만한 이들의 양호한 내마모 특성은 특히 언급할 만한 이점이다.
따라서 본 발명은 일반식(Ⅰ)의 화합물을 부가하는 것을 포함하는 윤활제, 가공액 및 작동액의 성능 특성 향상방법에 관한 것이다.
일반식(Ⅰ)의 화합물은 원래 공지된 방식으로 윤활 조성물과 혼합될 수 있다. 예컨대 이 화합물은 오일에 용이하게 용해될 수 있다. 소비됨에 따라서 적합한 윤활제에 의해 적합한 농도로 희석될 수 있는 마스터뱃치도 제조할 수 있다. 이러한 경우, 10중량%를 초과하는 농도도 또한 가능하다.
본 발명의 윤활제, 가공액 및 작동액은 기본적 특성을 향상시키기 위해 부가될 수 있는 다른 첨가제를 더 함유할 수 있다. 이들 다른 첨가제는 산화방지제, 금속 탈활성화제, 녹 방지제, 점도 향상제, 유동점 억제제, 세정제, 다른 극압 첨가제 및 내마모 첨가제를 포함한다.
이러한 추가의 첨가제의 상세한 예는 다음과 같다.
[페놀성 산화방지제]
1. 알킬화 모노페놀, 예를들어 2,6-디-삼차부틸-4-메틸페놀, 2-삼차부틸-4,6-디메틸페놀, 2,6-디-삼차부틸-4-에틸페놀, 2,6-디-삼차부틸-4-n-부틸페놀, 2,6-디-삼차부틸-4-이소부틸페놀, 2,6-디-시클로펜틸-4-메틸페놀, 2-(α-메틸시클로헥실)-4,6-디메틸페놀, 2,6-디-옥타데실-4-메틸페놀, 2,4,6-트리-시클로헥실페놀, 2,6-디-삼차부틸-4-메톡시메틸페놀, 2,6-디-노닐-4-메틸페놀, 2,4-디메틸-6-(1'-메틸-운데크-1'-일)-페놀, 2,4-디메틸-6-(1'-메틸-헵타데크-1'-일)-페놀, 2,4-디메틸-6-(1'-메틸-트리데크-1'-일)-페놀 및 이들의 혼합물.
2. 알킬티오메틸페놀, 예를들어 2,4-디-옥틸티오메틸-6-삼차부틸페놀, 2,4-디-옥틸티오메틸-6-메틸페놀, 2,4-디-옥틸티오메틸-6-에틸페놀 및 2,6-디-도데실티오메틸-4-노닐페놀.
3. 히드로퀴논 및 알킬화 히드로퀴논, 예컨대 2,6-디-삼차부틸-4-메톡시페놀, 2,5-디-삼차부틸-히드로퀴논, 2,5-디-삼차아밀-히드로퀴논, 2,6-디페닐-4-옥타데실옥시페놀, 2,6-디-삼차부틸-히드로퀴논, 2,5-디-삼차부틸-4-히드록시아니솔, 3,5-디-삼차부틸-4-히드록시아니솔, 3,5-디-삼차부틸-4-히드록시페닐 스테아레이트 및 비스(3,5-디-삼차부틸-4-히드록시페닐)아디페이트.
4. 히드록시화 티오디페닐 에테르, 예를들어 2,2'-티오-비스(6-삼차부틸-4-메틸페놀), 2,2'-티오-비스(4-옥틸페놀), 4,4'-티오-비스(6-삼차부틸-3-메틸페놀), 4,4'-티오-비스(6-삼차부틸-2-메틸페놀), 4,4'-티오-비스(3,6-디-2차아밀페놀) 및 4,4'-비스(2,6-디메틸-4-히드록시페닐)디술피드.
5. 알킬리덴 비스페놀, 예를들어 2,2'-메틸렌-비스(6-삼차부틸-4-메틸페놀), 2,2'-메틸렌-비스(6-삼차부틸-4-에틸페놀), 2,2'-메틸렌-비스[4-메틸-6-(α-메틸시클로헥실)-페놀], 2,2'-메틸렌-비스(4-메틸-6-시클로헥실페놀), 2,2'-메틸렌-비스(6-노닐-4-메틸페놀), 2,2'-메틸렌-비스(4,6-디-삼차부틸페놀), 2,2'-에틸리덴-비스(4,6-디-삼차부틸페놀), 2,2'-에틸리덴-비스(6-삼차부틸-4-이소부틸페놀), 2,2'-메틸렌-비스[6-(α-메틸벤질)-4-노닐페놀], 2,2'-메틸렌-비스[6-(α,α-디메틸벤질)-4-노닐페놀], 4,4'-메틸렌-비스(2,6-디-삼차부틸페놀), 4,4'-메틸렌-비스(6-삼차부틸-2-메틸페놀), 1,1-비스[5-삼차부틸-4-히드록시-2-메틸페닐)부탄, 2,6-비스(3-삼차부틸-5-메틸-2-히드록시벤질)-4-메틸페놀, 1,1,3-트리스-(5-삼차부틸-4-히드록시-2-메틸페닐)부탄, 1,1-비스(5-삼차부틸-4-히드록시-2-메틸페닐)-3-n-도데실머캅토부탄, 에틸렌 글리콜 비스[3,3-비스(3'-삼차부틸-4'-히드록시페닐)부티레이트], 비스(3-삼차부틸-4-히드록시-5-메틸페닐)디시클로펜타디엔, 비스[2-(3'-삼차부틸-2'-히드록시-5'-메틸벤질)-6-삼차부틸-4-메틸페닐]테레프탈레이트, 1,1-비스(3,5-디메틸-2-히드록시페닐)부탄, 2,2-비스(3,5-디-삼차부틸-4-히드록시페닐)-프로판, 2,2-비스(5-삼차부틸-4-히드록시-2-메틸페닐)-4-n-도데실머캅토부탄, 1,1,5,5-테트라(5-삼차부틸-4-히드록시-2-메틸페닐)펜탄.
6. O-, N- 및 S-벤질 화합물, 예를들어 3,5,3',5'-테트라-삼차부틸-4,4'-디히드록시-디벤질 에테르, 옥타데실-4-히드록시-3,5-디메틸벤질 머캅토아세테이트, 트리스(3,5-디-삼차부틸-4-히드록시벤질)아민, 비스(4-삼차부틸-3-히드록시-2,6-디메틸벤질)디티오테레프탈레이트, 비스(3,5-디-삼차부틸-4-히드록시벤질)술피드 및 이소옥틸-3,5-디-삼차부틸-4-히드록시벤질 머캅토아세테이트.
7. 히드록시벤질화 말로네이트, 예를 들어 디옥타데실-2,2-비스(3,5-디-삼차부틸-2-히드록시벤질)말로네이트, 디-옥타데실-2-(3-삼차부틸-4-히드록시-5-메틸벤질)-말로네이트, 디-도데실머캅토에틸-2,2-비스(3,5-디-삼차부틸-4-히드록시벤질)말로네이트, 비스-[4-(1,1,3,3-테트라메틸부틸)페닐]-2,2-비스(3,5-디-삼차부틸-4-히드록시벤질)말로네이트.
8. 방향족 히드록시벤질 화합물, 예를들어 1,3,5-트리스(3,5-디-삼차부틸-4-히드록시벤질)-2,4,6-트리메틸벤젠, 1,4-비스(3,5-디-삼차부틸-4-히드록시벤질)-2,3,5,6-테트라메틸벤젠 및 2,4,6-트리스(3,5-디-삼차부틸-4-히드록시벤질)페놀.
9. 트리아진 화합물, 예를들어 2,4-비스-옥틸머캅토-6-(3,5-디-삼차부틸-4-히드록시아닐리노)-1,3,5-트리스, 2-옥틸머캅토-4,6-비스(3,5-디-삼차부틸-4-히드록시아닐리노)-1,3,5-트리아진, 2-옥틸머캅토-4,6-비스(3,5-디-삼차부틸-4-히드록시페녹시)-1,3,5-트리아진, 2,4,6-트리스(3,5-디-삼차부틸-4-히드록시페녹시)-1,2,3-트리아진, 1,3,5-트리아진-(3,5-디-삼차부틸-4-히드록시벤질)이소시아누레이트, 1,3,5-트리스(4-삼차부틸-3-히드록시-2,6-디메틸벤질)이소시아누레이트, 2,4,6-트리스(3,5-디-삼차부틸-4-히드록시페닐에틸)-1,3,5-트리아진, 1,3,5-트리스(3,5-디-삼차부틸-4-히드록시페닐프로피온일)헥사히드로-1,3,5-트리아진 및 1,3,5-트리스(3,5-디시클로헥실-4-히드록시벤질)이소시아누레이트.
10. 벤질 포스포네이트, 예컨대 디메틸-2,5-디-삼차부틸-4-히드록시벤질 포스포네이트, 디에틸-3,5-디-삼차부틸-4-히드록시벤질포스포네이트, 디옥타데실-3,5-디-삼차부틸-4-히드록시벤질포스포네이트, 디옥타데실-5-삼차부틸-4-히드록시-3-메틸벤질 포스포네이트 및 모노에틸 3,5-디-삼차부틸-4-히드록시벤질포스포네이트의 칼슘 염.
11. 아실아미노페놀, 예컨대 4-히드록시라우르아닐리드, 4-히드록시스테아르아닐리드 및 옥틸 N-(3,5-디-삼차부틸-4-히드록시페닐)-카르바메이트.
12. 1가 또는 다가 알코올과 β-(3,5-디-삼차부틸-4-히드록시페닐)-프로피온산의 에스테르, 예컨대 메탄올, 에탄올, 옥타데칸올, 1,6-헥산디올, 1,9-노난디올, 에틸렌글리콜, 1,2-프로판디올, 네오펜틸 글리콜, 티오디에틸렌 글리콜, 디에틸렌 글리콜, 트리에틸렌 글리콜, 펜타에리트리톨, 트리스(히드록시에틸)이소시아누레이트, N,N'-비스(히드록시에틸)옥사미드, 3-티아운데칸올, 3-티아펜타데칸올, 트리메틸헥산디올, 트리메틸올프로판 및 4-히드록시메틸-1-포스파-2,6,7-트리옥사비시클로[2.2.2]-옥탄과의 에스테르.
13. 1가 또는 다가 알코올과 β-(5-삼차부틸-4-히드록시-3-메틸페닐)-프로피온산의 에스테르, 예를들어 메탄올, 에탄올, 옥타데칸올, 1,6-헥산디올, 1,9-노난디올, 에틸렌 글리콜, 1,2-프로판디올, 네오펜틸 글리콜, 티오디에틸렌 글리콜, 디에틸렌 글리콜, 트리에틸렌 글리콜, 펜타에리트리톨, 트리스(히드록시에틸)이소시아누레이트, N,N'-비스(히드록시에틸)옥사미드, 3-티아운데칸올, 3-티아펜타데칸올, 트리메틸헥산디올, 트리메틸올프로판 및 4-히드록시메틸-1-포스파-2,6,7-트리옥사비시클로-[2.2.2]옥탄과의 에스테르.
14. 1가 또는 다가 알코올과 β-(3,5-디시클로헥실-4-히드록시페닐)-프로피온산의 에스테르, 예를들어 메탄올, 에탄올, 옥타데칸올, 1,6-헥산디올, 1,9-노난디올, 에틸렌 글리콜, 1,2-프로판디올, 네오펜틸 글리콜, 티오디에틸렌 글리콜, 디에틸렌 글리콜, 트리에틸렌 글리콜, 펜타에리트리톨, 트리스(히드록시에틸)이소시아누레이트, N,N'-비스(히드록시에틸)옥사이드, 3-티아운데칸올, 3-티아펜타데칸올, 트리메틸헥산디올, 트리메틸올프로판 및 4-히드록시메틸-1-포스파-2,6,7-트리옥사비시클로[2.2.2]옥탄과의 에스테르.
15. 1가 또는 다가 알코올과 3,5-디-삼차부틸-4-히드록시페닐아세트산의 에스테르, 예를들어 메탄올, 에탄올, 옥타데칸올, 1,6-헥산디올, 1,9-노난디올, 에틸렌 글리콜, 1,2-프로판디올, 네오펜틸 글리콜, 티오디에틸렌 글리콜, 디에틸렌 글리콜, 트리에틸렌 글리콜, 펜타에리트리톨, 트리스(히드록시에틸)이소시아누레이트, N,N'-비스(히드록시에틸)옥사미드, 3-티아운데칸올, 3-티아펜타데칸올, 트리메틸헥산디올, 트리메틸올프로판 및 4-히드록시메틸-1-포스파-2,6,7-트리옥사비시클로[2.2.2]옥탄과의 에스테르.
16. β-(3,5-디-삼차부틸-4-히드록시페닐)-프로피온산의 아미드, 예를들어 N,N'-비스(3,5-디-삼차부틸-4-히드록시페닐프로피온일)헥사메틸렌디아민, N,N'-비스(3,5-디-삼차부틸-4-히드록시페닐프로피온일)트리메틸렌디아민 및 N,N'-비스(3,5-디-삼차부틸-4-히드록시페닐프로피온일)히드라진.
[아민 산화방지제의 예]
N,N'-디이소프로필-p-페닐렌디아민, N,N'-디이차부틸-p-페닐렌디아민, N,N'-비스(1,4-디메틸페닐)-p-페닐렌디아민, N,N'-비스(1-에틸-3-메틸펜틸)-p-페닐렌디아민, N,N'-비스(1-메틸헵틸)-p-페닐렌디아민, N,N'-디시클로헥실-p-페닐렌디아민, N,N'-디페닐-p-페닐렌디아민, N,N'-비스(2-나프틸)-p-페닐렌디아민, N-이소프로필-N'-페닐-p-페닐렌디아민, N-(1,3-디메틸-부틸)-N'-페닐-p-페닐렌디아민, N-(1-메틸헵틸)-N'-페닐-p-페닐렌디아민, N-시클로헥실-N'-페닐-p-페닐렌디아민, 4-(p-톨루엔술파모일)디페닐아민, N,N'-디메틸-N,N'-디이차부틸-p-페닐렌디아민, 디페닐아민, N-알릴디페닐아민, 4-이소프로폭시디페닐아민, N-페닐-1-나프틸아민, N-페닐-2-나프틸아민, 옥틸화 디페닐아민, 예컨대 p,p'-디삼차옥틸디페닐아민, 4-n-부틸아미노페놀, 4-부틸아미노페놀, 4-노난오일아미노페놀, 4-도데칸오일아미노페놀, 4-옥타데칸오일아미노페놀, 비스(4-메톡시페닐)아민, 2,6-디삼차부틸-4-디메틸아미노메틸페놀, 2,4'-디아미노디페닐메탄, 4,4'-디아미노디페닐메탄, N,N,N',N'-테트라메틸-4,4'-디아미노디페닐메탄, 1,2-비스[(2-메틸-페닐)아미노]에탄, 1,2-비스(페닐아미노)프로판, (o-톨릴)비구아나이드, 비스[4-(1',3'-디메틸부틸)페닐]아민, 삼차옥틸화 N-페닐-1-나프틸아민, 모노- 및 디알킬화 삼차 부틸/삼차 옥틸디페닐아민의 혼합물, 모노- 및 디알킬화 이소프로필/이소헥실디페닐아민의 혼합물, 모노- 및 디알킬화 삼차부틸디페닐아민의 혼합물, 2,3-디히드로-3,3-디메틸-4H-1,4-벤조티아진, 페노티아진, N-알릴페노티아진, N,N,N',N'-테트라페닐-1,4-다아미노부트-2-엔, N,N-비스(2,2,6,6-테트라메틸피페리드-4-일-헥사메틸렌디아민, 비스(2,2,6,6-테트라메틸피페리드-4-일)세바게이트, 2,2,6,6-테트라메틸피페리딘-4-온 및 2,2,6,6-테트라메틸피페리딘-4-올.
[다른 산화방지제의 예]
지방족 또는 방향족 포스파이트, 티오디프로피온산 또는 티오디아세트산의 에스테르, 또는 디티오카르밤산 또는 디티오인산의 염, 2,2,12,12-테트라메틸-5,9-디히드록시-3,7,11-트리티아트리데칸 및 2,2,15,15-테트라메틸-5,12-디히드록시-3,7,10,14-테트라티아헥사데칸.
[금속 탈활성화제, 예컨대 구리에 대한 탈활성화제의 예]
a) 벤조트리아졸 및 그의 유도체, 예컨대 4- 또는 5-알킬벤조트리아졸(예컨대 톨루트리아졸) 및 그의 유도체, 4,5,6,7-테트라히드로벤조트리아졸 및 5,5'-메틸렌비스벤조트리아졸; 벤조트리아졸 또는 톨루트리아졸의 만니히 염기, 예컨대 1-[비스(2-에틸헥실)아미노메틸)톨루트리아졸 및 1-[비스(2-에틸헥실)아미노메틸)벤조트리아졸; 및 1-(노닐옥시메틸)벤조트리아졸, 1-(1-부톡시에틸)벤조트리아졸 및 1-(1-시클로헥실옥시부틸)톨루트리아졸과 같은 알콕시알킬벤조트리아졸.
b) 1,2,4-트리아졸 및 그의 유도체, 예컨대 3-알킬(또는 아릴)-1,2,4-트리아졸, 및 1-[비스(2-에틸헥실)아미노메틸-1,2,4-트리아졸과 같은 1,2,4-트리아졸의 만니히 염기; 1-(1-부톡시에틸)-1,2,4-트리아졸과 같은 알콕시알킬-1,2,4-트리아졸; 및 아실화 3-아미노-1,2,4-트리아졸.
c) 이미다졸 유도체, 예컨대 4,4'-메틸렌비스(2-운데실-5-메틸이미다졸) 및 비스[(N-메틸)이미다졸-2-일]카르비놀 옥틸 에테르.
d) 황 함유 헤테로고리 화합물, 예컨대 2-머캅토벤조티아졸, 2,5-디머캅토-1,3,4-티아디아졸 및 그의 유도체; 및 3,5-비스[디(2-에틸헥실)아미노메틸]-1,3,4-티아디아졸린-2-온.
e) 아미노 화합물, 예컨대 살리실리덴프로필렌디아민, 살리실아미노구아니딘 및 그의 염.
[녹 방지제의 예]
a) 유기산, 이들의 에스테르, 금속 염, 아민염 및 무수물, 예컨대 알킬- 및 알켄일숙신산 및 이들과 알코올, 디올 또는 히드록시카르복시산과의 부분적 에스테르, 알킬-및 알켄일숙신산과의 부분적 아미드, 4-노닐페녹시아세트산, 알콕시- 및 알콕시에톡시카르복시산, 예컨대 도데실옥시아세트산, 도데실옥시(에톡시)아세트산 및 그의 아민염, 및 N-올레오일사르코신, 소르비탄 모노올레에이트, 납 나프테네이트, 무수 알켄일숙신산, 예컨대 도데센일숙신산 무수물, 2-(카르복시에틸)-1-도데실-3-메틸글리세롤 및 그의 아민염.
b) 질소 함유 화합물, 예컨대
Ⅰ. 일차, 이차 또는 삼차 지방족 또는 시클로지방족 아민 및 유기산 및 무기산의 아민염, 예컨대 지용성 알킬암모늄 카르복실레이트, 및 또한 1-[N,N-비스(2-히드록시에틸)아미노]-3-(4-노닐페녹시)프로판-2-올.
Ⅱ. 헤테로고리 화합물, 예컨대 치환된 이미다졸린 및 옥사졸린, 및 2-헵타데센일-1-(2-히드록시에틸)이미다졸린.
c) 인 함유 화합물, 예컨대 인산의 아민염, 부분적 에스테르 또는 포스폰산 부분적 에스테르, 및 아연 디알킬디티올포스페이트.
d) 황 함유 화합물, 예컨대 바륨 디노닐나프탈렌술포네이트, 칼슘 석유 술포네이트, 알킬티오-치환된 카르복시산, 지방족 2-술포카르복시산의 에스테르 및 그의 염.
e) 글리세롤 유도체, 예컨대 글리세롤 모노올레에이트, 1-(알킬페녹시)-3-(2-히드록시에틸)글리세롤, 1-(알킬페녹시)-3-(2,3-디히드록시프로필)글리세롤 및 2-카르복시알킬-1,3-디알킬글리세롤.
[점도지수 향상제의 예]
폴리아크릴레이트, 폴리메타크릴레이트, 비닐피롤리돈/메타크릴레이트 공중합체, 폴리비닐 피롤리돈, 폴리부텐, 올레핀 공중합체, 스티렌/아크릴레이트 공중합체 및 폴리에테르.
[유동점 억제제의 예]
폴리메타크릴레이트 및 알킬화 나프탈렌 유도체
[분산제/계면활성제의 예]
폴리부텐일숙신 아미드 또는 -이미드, 폴리부텐일인산 유도체 및 염기성 마그네슘, 칼슘 및 바륨 술포네이트 및 페놀레이트.
[내마모성 첨가제의 예]
황- 및/또는 인- 및/또는 할로겐-함유 화합물, 예컨대 황화 올레핀 및 식물유, 아연 디알킬디티오포스페이트, 알킬화 트리페닐 포스페이트, 트리톨릴 포스페이트, 트리크레실 포스페이트, 염소화 파라핀, 알킬 및 아릴 디- 및 트리술피드, 모노- 및 디알킬 포스페이트의 아민 염, 메틸포스폰산의 아민염, 디에탄올아미노메틸톨릴트리아졸, 비스(2-에틸헥실)아미노메틸톨릴트리아졸, 2,5-디머캅토-1,3,4-티아디아졸의 유도체, 에틸 3-[(디이소프로폭시포스피노티오일)티오]프로피오네이트, 트리페닐 티아포스페이트(트리페놀포스포로티오에이트), 트리스(알킬페닐)포스포로티오에이트 및 그의 혼합물(예컨대 트리스(이소노닐페실)포스포로티오에이트), 디페닐 모노노닐페닐 포스포로티오에이트, 이소부틸페닐 디페닐 포스포로티오에이트, 3-히드록시-1,3-티아포스페탄-3-옥사이드의 도데실아민 염, 트리티오포스폰산 5,5,5-트리스[이소옥틸 2-아세테이트], 2-머캅토벤조티아졸의 유도체, 예컨대 1-[N,N-비스(2-에틸헥실)아미노메틸]-2-머캅토-1H-1,3-벤조티아졸, 및 에톡시카르보닐-5-옥틸디티오카르바메이트.
본 발명의 화합물은 원래 공지된 방법에 의해, 유리하게는 하기 도식에 따라서 제조한다:
디티오인산을 아크릴산 또는 메타크릴산에 부가한 후, 생성한 치환된 카르복시산을 통상의 방법, 전형적으로 파라-톨루술폰산 또는 메탄술폰산을 촉매로 부가하고 또 경우에 따라 톨루엔을 연행제로 사용하는 것에 의해 알코올 A-OH를 사용하여 에스테르화시킨다.
상기 유형의 반응은 실시예 12에 예로 나타낸다.
이와 다르게, 영국 특허 1 569 730호에 기재된 바와 같이 디티오인산의 에스테르를 아크릴산 또는 메타크릴산과 반응시킬 수 있다.
상기 반응 도식에 포함된 공정을 실행하기 위한 특수한 변수는 하기 실시예로 부터 추측할 수 있다. 이들 실시예 및 용도 실시예는 본 발명을 보다 자세하게 설명하지만, 이에 한정되지 않는다. 특별히 지시하지 않는 한, 부 및 %는 중량기준이다.
[실시예 1: 0,0-디이소프로필-S-2-카르복시에틸 디티오포스페이트]
교반하면서, 15.15g(0.2몰)의 아크릴산 및 0.01 g의 히드로퀴논을 70℃에서 1.5시간에 걸쳐 44.78g(0.2몰)의 디이소프로필 디티오포스페이트에 부가한다. 70℃에서 6시간 동안 교반을 계속하고, 또 쉽게 휘발하는 성분을 감압(70℃/0.02밀리바아/0.5시간)하에서 제거한다. 수율: 담황색 액체 57.2g(95%), nD 20: 1.5050,31P-NMR: 91.4 ppm/H3PO4.
상기 실시예 1에 기재한 바에 따라서 하기 표 1에 수록한 실시예 2 내지 11의 화합물을 제조한다.
[실시예 12: O,O-디이소프로필-S-2-[카르보-2', 3'-디히드록시프로폭시]에틸 디티오포스페이트]
실시예 1에 따른 57.2g(0.2몰)의 O,O-디이소프로필-S-2-카르복시에틸 디티오포스페이트, 18.79g(0.2몰)의 글리세롤, 1.9g의 p-톨루엔술폰산 및 150ml의 톨루엔의 혼합물을 물 분리기상에서 1시간 동안 환류시킨다. 생성한 생성물을 50ml의 10% 황산나트륨 용액으로 세척한 다음 10% 황산 나트륨 용액/5% 탄산 나트륨 용액으로 2회 세척하고 또 무수 황산 나트륨상에서 건조시킨다.
회전 증발기상에서 증류하는 것에 의해 용매를 제거하고 잔류하는 용매를 진공하에서 스트립 제거한다(60℃/ 0.05 밀리바아/1시간).
수율: 64.7g(90%)의 무색 액체, nD 20: 1.5153,31P-NMR: 91.3 ppm/H3PO4.
실시예 7, 3, 8, 9, 5, 11 및 1의 화합물을 에스테르 성분으로 사용하여 실시예 12에 기재된 방법에 따라서 하기 표 2에 수록한 실시예 13 내지 19의 화합물을 제조한다.
표 3에 수록된 실시예 20 내지 27의 화합물은 글리세롤을 상이한 알코올 R'OH로 대체한 이외에는 실시예 12에 기재된 공정에 의해 제조한다.
[실시예 28: SRV 시험]
내마모성 및 마찰 감소 특성을 시험하기 위해, 신규한 디티오포스페이트를 도핑되지 않은 윤활유에 혼입시키고 또 SRV 장치(독일 뮨헨에 소재하는 옵티몰 게엠베하가 제조한 진동 마찰 장치; 윤활공학 39(11) 1982, Advert. Index. cover 3, 729 페이지)를 이용하여 100℃ 및 150℃에서 마찰 계수 μ를 측정한다.
이 방법에서, 시험 오일의 막이 있는 단단하게 고정된 금속 실린더에 대해 200N의 힘으로 진동볼(50Hz)을 압착시킨다. 전압변환기를 이용하여 수평력과 수직력을 측정한다. 이렇게 수득한 신호를 직접적으로 기록계로 전송한다. 시험의 결과, 금속 실린더상에 있는 마모 흔적의 횡단면을 프로필로미터(TALYSURF 10)을 이용하여 측정한다. 시험결과를 하기 표 4에 요약한다.
도핑되지 않은 베이스 오일에 대한 낮은 마모지수 및 마찰계수는 상기 화합물이 내마모 특성을 갖는다는 것을 나타낸다.
Claims (8)
- 하기 일반식(Ⅰ)의 화합물:상기식에서,R1및 R2는 서로 독립해서 C3-C18알킬, C5-C12시클로알킬, C5-C6시클로알킬메틸, C9-C10비시클로알킬메틸, C9-C10트리시클로알킬메틸, 페닐, C7-C24알킬페닐이거나 또는 서로 합쳐져서이며,R3은 수소 또는 메틸이고,A는이고,R4는 수소 또는 C1-C6알킬이며, 또R5는 5- 또는 6-원 포화 헤테로고리이고,R6은 수소 또는 메틸이며,n은 1 내지 11의 정수이고 또m은 0 내지 4의 정수임.
- 제1항에 있어서, R1및 R2가 서로 독립해서 C3-C18알킬, C5-C6시클로알킬 또는 C7-C18알킬페닐이고, R5는 테트라히드로푸릴이며, n은 1 내지 6이고 또 m이 0 내지 2인 화합물.
- a) 윤활제, 가공액 또는 작동액, 및b) 제1항에 따른 한개 이상의 일반식(Ⅰ)의 화합물을 포함하는 조성물.
- 제3항에 있어서, 성분 B)가 한개 이상의 제2항에 따른 일반식(Ⅰ)의 화합물인 조성물.
- 제3항에 있어서, 성분 A)가 윤활제인 조성물.
- 제5항에 있어서, 윤활제가 엔진 오일인 조성물.
- 제3항에 있어서, 산화방지제, 금속 탈활성화제, 극압 및 내마모 첨가제 및 유동점 억제제로 구성된 군으로 부터 선정된 안정화제를 추가로 더 포함하는 조성물.
- 제1항에 따른 한개 이상의 일반식(Ⅰ)의 화합물을 부가하는 것을 포함하는 윤활조성물, 작동액 및 가공액의 성능 특성을 향상시키는 방법.
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US3350348A (en) * | 1965-04-05 | 1967-10-31 | Mobil Oil Corp | Lubricating oil additives |
NL6700169A (ko) * | 1966-01-13 | 1967-07-14 | ||
US3629376A (en) * | 1967-05-26 | 1971-12-21 | Chemagro Corp | S-carboethoxymethyl-s-s-dialkyl-trithiophosphates |
SE371567B (ko) * | 1968-06-19 | 1974-11-25 | Montedison Spa | |
GB1287331A (en) * | 1970-01-29 | 1972-08-31 | Ciba Geigy Uk Ltd | Phosphorodithioic acid esters |
US3712878A (en) * | 1970-08-25 | 1973-01-23 | Uniroyal Inc | O,o,s-triesters of phosphorodithioic acid as accelerators in the sulfur vulcanization of epdm rubbers |
US4333841A (en) * | 1978-10-19 | 1982-06-08 | Ciba-Geigy Corporation | Dithiophosphate lubricant additives |
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US4435338A (en) * | 1980-09-29 | 1984-03-06 | Ciba-Geigy Corporation | Dithiophosphates |
US4544492A (en) * | 1983-05-09 | 1985-10-01 | Ciba-Geigy Corporation | Lubricant compositions |
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-
1993
- 1993-05-12 TW TW082103721A patent/TW279839B/zh active
- 1993-05-26 GB GB9310875A patent/GB2267495B/en not_active Expired - Lifetime
- 1993-05-27 US US08/068,375 patent/US5362419A/en not_active Expired - Lifetime
- 1993-05-28 DE DE4317943A patent/DE4317943B4/de not_active Expired - Lifetime
- 1993-05-31 CA CA002097384A patent/CA2097384C/en not_active Expired - Lifetime
- 1993-05-31 MX MX9303213A patent/MX9303213A/es unknown
- 1993-06-01 FR FR9306509A patent/FR2691707B1/fr not_active Expired - Lifetime
- 1993-06-01 KR KR1019930009979A patent/KR100274361B1/ko not_active IP Right Cessation
- 1993-06-01 JP JP15418293A patent/JP3687051B2/ja not_active Expired - Lifetime
- 1993-06-01 IT ITMI931151A patent/IT1270821B/it active IP Right Grant
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100702379B1 (ko) * | 2000-05-08 | 2007-04-02 | 스미또모 가가꾸 가부시끼가이샤 | 해충에 의한 섬유 제품의 식해를 방지하는 방법 및 조성물 |
Also Published As
Publication number | Publication date |
---|---|
FR2691707A1 (fr) | 1993-12-03 |
GB2267495A (en) | 1993-12-08 |
GB2267495B (en) | 1995-09-20 |
US5362419A (en) | 1994-11-08 |
MX9303213A (es) | 1994-01-31 |
KR940000469A (ko) | 1994-01-03 |
GB9310875D0 (en) | 1993-07-14 |
DE4317943A1 (de) | 1993-12-09 |
TW279839B (ko) | 1996-07-01 |
FR2691707B1 (fr) | 1996-10-04 |
ITMI931151A1 (it) | 1994-12-01 |
CA2097384C (en) | 2005-01-25 |
JPH0641161A (ja) | 1994-02-15 |
CA2097384A1 (en) | 1993-12-03 |
IT1270821B (it) | 1997-05-13 |
JP3687051B2 (ja) | 2005-08-24 |
DE4317943B4 (de) | 2006-08-10 |
ITMI931151A0 (it) | 1993-06-01 |
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