DE4317943B4 - Dithiophosphorsäurederivate als Schmiermitteladditive - Google Patents
Dithiophosphorsäurederivate als Schmiermitteladditive Download PDFInfo
- Publication number
- DE4317943B4 DE4317943B4 DE4317943A DE4317943A DE4317943B4 DE 4317943 B4 DE4317943 B4 DE 4317943B4 DE 4317943 A DE4317943 A DE 4317943A DE 4317943 A DE4317943 A DE 4317943A DE 4317943 B4 DE4317943 B4 DE 4317943B4
- Authority
- DE
- Germany
- Prior art keywords
- tert
- butyl
- methyl
- bis
- compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 title description 6
- 239000003879 lubricant additive Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 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 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 26
- 239000000314 lubricant Substances 0.000 claims description 25
- 239000012530 fluid Substances 0.000 claims description 14
- 238000005555 metalworking Methods 0.000 claims description 10
- 239000000654 additive Substances 0.000 claims description 7
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
- 239000006078 metal deactivator Substances 0.000 claims description 2
- 239000010705 motor oil Substances 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract description 3
- -1 3-heptyl Chemical group 0.000 description 39
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 19
- 150000002148 esters Chemical class 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 9
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 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
- 229910052717 sulfur Inorganic materials 0.000 description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- YEWBOZCFGXOUQW-UHFFFAOYSA-N 2,6,7-trioxa-1-phosphabicyclo[2.2.2]octan-4-ylmethanol Chemical compound C1OP2OCC1(CO)CO2 YEWBOZCFGXOUQW-UHFFFAOYSA-N 0.000 description 4
- KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-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
- 125000000217 alkyl group Chemical group 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- FPQJEXTVQZHURJ-UHFFFAOYSA-N n,n'-bis(2-hydroxyethyl)oxamide Chemical compound OCCNC(=O)C(=O)NCCO FPQJEXTVQZHURJ-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 239000003760 tallow Substances 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
- 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 239000011575 calcium Substances 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
- 239000007788 liquid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- 150000000178 1,2,4-triazoles Chemical class 0.000 description 2
- 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
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-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
- SLUKQUGVTITNSY-UHFFFAOYSA-N 2,6-di-tert-butyl-4-methoxyphenol Chemical compound COC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SLUKQUGVTITNSY-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-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
- WTWGHNZAQVTLSQ-UHFFFAOYSA-N 4-butyl-2,6-ditert-butylphenol Chemical compound CCCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 WTWGHNZAQVTLSQ-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
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- 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
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 235000019484 Rapeseed oil Nutrition 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
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-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
- 238000007792 addition Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000010775 animal oil Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 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
- 230000000694 effects Effects 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 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
- 239000000243 solution Substances 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
- 239000000126 substance Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- ZEBMSMUPGIOANU-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methylphosphonic acid Chemical compound CC(C)(C)C1=CC(CP(O)(O)=O)=CC(C(C)(C)C)=C1O ZEBMSMUPGIOANU-UHFFFAOYSA-N 0.000 description 1
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-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
- 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
- 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
- ZJNLYGOUHDJHMG-UHFFFAOYSA-N 1-n,4-n-bis(5-methylhexan-2-yl)benzene-1,4-diamine Chemical compound CC(C)CCC(C)NC1=CC=C(NC(C)CCC(C)C)C=C1 ZJNLYGOUHDJHMG-UHFFFAOYSA-N 0.000 description 1
- BJLNXEQCTFMBTH-UHFFFAOYSA-N 1-n,4-n-di(butan-2-yl)-1-n,4-n-dimethylbenzene-1,4-diamine Chemical compound CCC(C)N(C)C1=CC=C(N(C)C(C)CC)C=C1 BJLNXEQCTFMBTH-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
- 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
- GFVSLJXVNAYUJE-UHFFFAOYSA-N 10-prop-2-enylphenothiazine Chemical compound C1=CC=C2N(CC=C)C3=CC=CC=C3SC2=C1 GFVSLJXVNAYUJE-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- TUYBEVLJKZQJPO-UHFFFAOYSA-N 19-(3,5-ditert-butyl-4-hydroxyphenyl)heptatriacontan-19-ylphosphonic acid Chemical compound CCCCCCCCCCCCCCCCCCC(CCCCCCCCCCCCCCCCCC)(P(O)(O)=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 TUYBEVLJKZQJPO-UHFFFAOYSA-N 0.000 description 1
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- FSWDLYNGJBGFJH-UHFFFAOYSA-N n,n'-di-2-butyl-1,4-phenylenediamine Chemical compound CCC(C)NC1=CC=C(NC(C)CC)C=C1 FSWDLYNGJBGFJH-UHFFFAOYSA-N 0.000 description 1
- XRXMSAXBKVILLN-UHFFFAOYSA-N n,n,n',n'-tetraphenylbut-2-ene-1,4-diamine Chemical compound C=1C=CC=CC=1N(C=1C=CC=CC=1)CC=CCN(C=1C=CC=CC=1)C1=CC=CC=C1 XRXMSAXBKVILLN-UHFFFAOYSA-N 0.000 description 1
- KEZPMZSDLBJCHH-UHFFFAOYSA-N n-(4-anilinophenyl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(C=C1)=CC=C1NC1=CC=CC=C1 KEZPMZSDLBJCHH-UHFFFAOYSA-N 0.000 description 1
- KESXDDATSRRGAH-UHFFFAOYSA-N n-(4-hydroxyphenyl)butanamide Chemical compound CCCC(=O)NC1=CC=C(O)C=C1 KESXDDATSRRGAH-UHFFFAOYSA-N 0.000 description 1
- JVKWTDRHWOSRFT-UHFFFAOYSA-N n-(4-hydroxyphenyl)dodecanamide Chemical compound CCCCCCCCCCCC(=O)NC1=CC=C(O)C=C1 JVKWTDRHWOSRFT-UHFFFAOYSA-N 0.000 description 1
- VQLURHRLTDWRLX-UHFFFAOYSA-N n-(4-hydroxyphenyl)nonanamide Chemical compound CCCCCCCCC(=O)NC1=CC=C(O)C=C1 VQLURHRLTDWRLX-UHFFFAOYSA-N 0.000 description 1
- YASWBJXTHOXPGK-UHFFFAOYSA-N n-(4-hydroxyphenyl)octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC1=CC=C(O)C=C1 YASWBJXTHOXPGK-UHFFFAOYSA-N 0.000 description 1
- SAVBPLYIBMOJIH-UHFFFAOYSA-N n-(4-methylpentyl)-n-phenylaniline Chemical class C=1C=CC=CC=1N(CCCC(C)C)C1=CC=CC=C1 SAVBPLYIBMOJIH-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- CVVFFUKULYKOJR-UHFFFAOYSA-N n-phenyl-4-propan-2-yloxyaniline Chemical compound C1=CC(OC(C)C)=CC=C1NC1=CC=CC=C1 CVVFFUKULYKOJR-UHFFFAOYSA-N 0.000 description 1
- IMXRBCGZTVENAC-UHFFFAOYSA-N n-phenyl-n-(2,4,4-trimethylpentan-2-yl)aniline Chemical class C=1C=CC=CC=1N(C(C)(C)CC(C)(C)C)C1=CC=CC=C1 IMXRBCGZTVENAC-UHFFFAOYSA-N 0.000 description 1
- NYLGUNUDTDWXQE-UHFFFAOYSA-N n-phenyl-n-prop-2-enylaniline Chemical compound C=1C=CC=CC=1N(CC=C)C1=CC=CC=C1 NYLGUNUDTDWXQE-UHFFFAOYSA-N 0.000 description 1
- MHJCZOMOUCUAOI-UHFFFAOYSA-N n-tert-butyl-n-phenylaniline Chemical class C=1C=CC=CC=1N(C(C)(C)C)C1=CC=CC=C1 MHJCZOMOUCUAOI-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 235000019488 nut oil Nutrition 0.000 description 1
- 239000010466 nut oil Substances 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
- IXVLEAZXSJJKFR-UHFFFAOYSA-N octadecyl 2-[(4-hydroxy-3,5-dimethylphenyl)methylsulfanyl]acetate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CSCC1=CC(C)=C(O)C(C)=C1 IXVLEAZXSJJKFR-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 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
- 235000014593 oils and fats Nutrition 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
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 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
- 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
- 150000003014 phosphoric acid esters Chemical class 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
- 229920013639 polyalphaolefin 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
- 238000002360 preparation method Methods 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
- 230000001603 reducing effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003307 slaughter Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 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
- 238000003756 stirring Methods 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000004094 surface-active agent Substances 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
- 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 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
- SMVBWTKCDCPTQG-UHFFFAOYSA-N tris[2-(7-methyloctyl)phenoxy]-sulfanylidene-$l^{5}-phosphane Chemical compound CC(C)CCCCCCC1=CC=CC=C1OP(=S)(OC=1C(=CC=CC=1)CCCCCCC(C)C)OC1=CC=CC=C1CCCCCCC(C)C SMVBWTKCDCPTQG-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
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M167/00—Lubricating compositions characterised by the additive being a mixture of a macromolecular compound, a non-macromolecular compound and a compound of unknown or incompletely defined constitution, each of these compounds being essential
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/6551—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/10—Thio derivatives
- C10M137/105—Thio derivatives not containing metal
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/047—Thioderivatives not containing metallic elements
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2225/02—Macromolecular compounds from phosphorus-containg monomers, obtained by reactions involving only carbon-to-carbon unsaturated bonds
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/252—Diesel engines
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/252—Diesel engines
- C10N2040/253—Small diesel engines
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
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Abstract
Verbindungen
der Formel I R1 und
R2 unabhängig
voneinander C3-C18-Alkyl, C5-C12-Cycloalkyl,
C5-C6-Cycloalkyl-methyl,
C9-C10-Bicycloalkyl-methyl,
C9-C10-Tricycloalkyl-methyl,
Phenyl, C7-C24-Alkylphenyl oder zusammenbedeuten,
R3 Wasserstoff oder Methyl ist,
A für-CH2[CH(OH)]mCH2OH steht,
R4 Wasserstoff oder C1-C6-Alkyl ist und
R5 einen 5-6-gliedrigen, gesättigten heterozyklischen Ring darstellt,
R6 Wasserstoff oder Methyl ist,
n eine Zahl von 1 bis 11 und m eine Zahl von 0 bis 4 bedeuten.
Phenyl, C7-C24-Alkylphenyl oder zusammenbedeuten,
R3 Wasserstoff oder Methyl ist,
A für-CH2[CH(OH)]mCH2OH steht,
R4 Wasserstoff oder C1-C6-Alkyl ist und
R5 einen 5-6-gliedrigen, gesättigten heterozyklischen Ring darstellt,
R6 Wasserstoff oder Methyl ist,
n eine Zahl von 1 bis 11 und m eine Zahl von 0 bis 4 bedeuten.
Description
- Die vorliegende Erfindung betrifft Dithiophosphorsäurederivate sowie diese enthaltende Schmiermittel, Hydraulik- und Metallbearbeitungsflüssigkeiten.
- (Thio-)Phosphorsäureester sind in Kombination mit Festschmierstoffen wie Graphit empfohlen worden (EP-A-0 214 434).
- Es sind ferner Hochtemperaturschmiermitteladditve bekannt, die Verbindungen der Formel (RIVX)nP(=Y)(ZRV)3-n, wobei X, Y und Z unabhängig voneinander O oder S bedeuten und RIV und RV C1-C12-Alkyl ist, das durch -O-, -S- oder -CO-O- unterbrochen sein kann (EP-A-0 267 875).
- Die zur Zeit vorherrschenden Phosphor-Schwefel-Additive für Schmiermittel sind Zinkdialkyldithiophosphate. Moderne Verbrennungskraftmaschinen erfordern allerdings immer häufiger möglichst aschearme Schmierstoffadditive, d.h. der Metallgehalt sollte möglichst gering sein.
- Überraschenderweise wurde nun gefunden, daß die unten beschriebenen Verbindungen der Formel I insbesondere bei höheren Temperaturen einen sehr guten Verschleißschutz bewirken. Die Verbindungen enthalten kein Zink, genügen also modernen Anforderungen, und sind flüssig und damit im Zusammenhang mit Schmiermitteln vorteilhaft zu handhaben.
- Die Erfidung betrifft daher Verbindungen der Formel I R1 und R2 unabhängig voneinander C3-C18-Alkyl, C5-C12-Cycloalkyl, C5-C6-Cycloalkyl-methyl, C9-C10-Bicycloalkyl-methyl, C9-C10-Tricycloalkyl-methyl,
Phenyl, C7-C24-Alkylphenyl oder zusammenbedeuten,
R3 Wasserstoff oder Methyl ist,
A für-CH2-CO-OR4, -CH2-R5 oder -CH2[CH(OH)]mCH2OH steht,
R4 Wasserstoff oder C1-C6-Alkyl ist und
R5 einen 5-6-gliedrigen, gesättigten heterozyklischen Ring darstellt,
R6 Wasserstoff oder Methyl ist,
n eine Zahl von 1 bis 11 und m eine Zahl von 0 bis 4 bedeuten. - Stellen in obigen Formeln R1 und R2 C3-C18-Alkyl dar, so handelt es sich dabei um verzweigte oder unverzweigte Reste. Beispiele hierfür sind Propyl, Isopropyl, n-Butyl, Isobutyl, t-Butyl, Pentyl, Isopentyl, Hexyl, Heptyl, 3-Heptyl, Octyl, 2-Ethylhexyl, Nonyl, Decyl, Undecyl, Dodecyl, Tridecyl, Tetradecyl, Pentadecyl, Hexadecyl, Heptadecyl, Octadecyl, 2-Ethylbutyl, 1-Methylpentyl, 1,3-Dimethylbutyl, 1,1,3,3-Tetramethylbutyl, 1-Methylhexyl, Isoheptyl, 1-Methylheptyl, 1,1,3-Trimethylhexyl oder 1-Methylundecyl.
- R1 und R2 als C5-C12-Cycloalkyl können z.B. Cyclopentyl, Cyclohexyl, Cycloheptyl, Cyclooctyl oder Cyclododecyl sein. Cyclopentyl und Cyclohexyl ist bevorzugt, insbesondere Cyclohexyl.
- Sind R1 und R2 C5-C6-Cycloalkyl-methyl, so ist darunter Cyclopentylmethyl und vor allem Cyclohexylmethyl zu verstehen.
- Als C9-C10-Bicycloalkyl-methyl sind R1 und R2 z.B. Decalinylmethyl. Als C9-C10-Tricycloalkyl-methyl haben R1 und R2 vorzugsweise die Bedeutung einer Gruppe der FormelR5 als 5-6-gliedriger heterozyklischer Ring kann z.B. Piperidino, Pyrrolidino, Piperazino, Morpholino, Pyrimidino oder Tetrahydrofuryl, insbesondere 2-Tetrahydrofuryl, sein.
- Bevorzugt sind Verbindungen, worin R1 und R2 unabhängig voneinander C3-C18-Alkyl, C5-C6-Cycloalkyl oder C7-C18-Alkylphenyl bedeuten,
R5 Tetrahydrofuryl darstellt,
n 1 bis 6 ist und m für 0 bis 2 steht. - Besonders bevorzugt sind R1 und R2 gleich. R3 ist insbesondere Wasserstoff.
- Die Erfindung betrifft ferner Zusammensetzungen enthaltend
- a) einen Schmierstoff, eine Metallbearbeitungs- oder Hydraulikflüssigkeit und
- b)mindestens eine Verbindung der Formel I, wobei die oben als bevorzugt genannten
- Verbindungen zu bevorzugten Zusammensetzungen führen.
- Die in den erfindungsgemäßen Zusammensetzungen enthaltenen Schmierstoffe, Hydraulik- und Metallbearbeitungsflüssigkeiten können sich mehr oder weniger leicht unter Einfluß von Wärme, mechanischer Belastung (insbesondere durch Scherkräfte) und chemischen Reagentien (besonders Luftsauerstoff) zersetzen.
- Dem Schutz vor solchen Einflüssen dienen die Verbindungen der Formel I, die in den erfindungsgemäßen Zusammensetzungen zweckmäßig zu 0.01 bis 10, beispielsweise zu 0.05 bis 5, vorzugsweise zu 0.05 bis 3, insbesondere jedoch zu 0.1 bis 2 Gew.-% vorliegen sollen. Es kann sich dabei um eine oder mehrere dieser Verbindungen handeln, und die Gewichtsprozentangaben beziehen sich auf die gesamte Menge dieser Verbindungen. Berechnungsgrundlage ist dabei das Gesamtgewicht des Schmierstoffes bzw. der Metallbearbeitungs- oder Hydraulikflüssigkeit ohne die Verbindungen der Formel I.
- Die in Frage kommenden Schmierstoffe, Metallbearbeitungs- und Hydraulikflüssigkeiten basieren beispielsweise auf mineralischen oder synthetischen Ölen oder Mischungen davon. Die Schmierstoffe sind dem Fachmann geläufig und in der einschlägigen Fachliteratur, wie beispielsweise in Dieter Klamann, "Schmierstoffe und verwandte Produkte" (Verlag Chemie, Weinheim, 1982), in Schewe-Kobek, "Das Schmiermittel-Taschenbuch" (Dr. Alfred Hüthig-Verlag, Heidelberg, 1974) und in "Ullmanns Enzyklopädie der technischen Chemie", Bd. 13, Seiten 85-94 (Verlag Chemie, Weinheim, 1977) beschrieben.
- Die Schmierstoffe sind insbesondere Öle und Fette, beispielsweise basierend auf einem Mineralöl. Bevorzugt sind Öle.
- Eine weitere Gruppe von Schmierstoffen, die zur Anwendung. gelangen können, sind pflanzliche oder tierische Öle, Fette, Talge und Wachse oder deren Gemische untereinander oder Gemische mit den erwähnten mineralischen oder synthetischen Ölen. Pflanzliche und tierische Öle, Fette, Talge und Wachse sind beispielsweise Palmkernöl, Palmöl, Olivenöl, Rüböl, Rapsöl, Leinöl, Erdnußöl, Sojabohnenöl, Baumwollöl, Sonnenblumenöl, Kürbiskernöl, Kokosnußöl, Maisöl, Rizinusöl, Baumnußöl und Mischungen davon, Fischöle, Talge von Schlachttieren wie Rindertalg, Klauenfett und Knochenöl sowie deren modifizierte, epoxidierte und sulfoxidierte Formen, beispielsweise epoxidiertes Sojabohnenöl.
- Die Mineralöle basieren insbesondere auf Kohlenwasserstoffverbindungen.
- Beispiele von synthetischen Schmierstoffen umfassen Schmierstoffe auf der Basis der aliphatischen oder aromatischen Carboxylester, der polymeren Ester, der Polyalkylenoxide, der Phosphorsäureester, der Poly-α-olefme oder der Silicone, eines Diesters einer zweiwertigen Säure mit einem einwertgen Alkohol, wie z.B. Dioctylsebacat oder Dinonyladipat, eines Triesters von Trimethylolpropan mit einer einwertigen Säure oder mit einem Gemisch solcher Säuren, wie z.B. Trimethylolpropantripelargonat, Trimethylolpropan-tricaprylat oder Gemische davon, eines Tetraesters von Pentaerythrit mit einer einwertigen Säure oder mit einem Gemisch solcher Säuren, wie z.B. Pentaerythrit-tetra caprylat, oder eines komplexen Esters von einwertigen und zweiwertigen Säuren mit mehrwertigen Alkoholen, z.B. ein komplexer Ester von Trimethylolpropan mit Capryl- und Sebacinsäure oder von einem Gemisch davon. Besonders geeignet sind neben Mineralölen z.B. Poly-α-Olefine, Schmierstoffe auf Esterbasis, Phosphate, Glykole, Polyglykole und Polyalkylenglykole, sowie deren Mischungen mit Wasser.
- Metallbearbeitungsflüssigkeiten und Hydraulikflüssigkeiten können auf Basis der gleichen Substanzen hergestellt werden wie vorstehend für die Schmiermittel beschrieben. Häufig handelt es sich dabei auch um Emulsionen solcher Substanzen in Wasser oder anderen Flüssigkeiten.
- Erfindungsgemäße Schmierstoffzusammensetzungen finden z.B. Verwendung in Verbrennungsmotoren, z.B. in Kraftfahrzeugen, ausgerüstet z.B. mit Motoren des Otto-, Diesel-, Zweitakt-, Wankel- oder Orbitaltyps.
- Die Verbindungen der Formel I sind gut in Schmierstoffen, Metallbearbeitungs- und Hydraulikflüssigkeiten löslich und sind deshalb als Zusätze zu Schmierstoffen, Metallbearbeitungs- und Hydraulikflüssigkeiten besonders geeignet, und es ist besonders auf ihre überrachend gute verschleißhemmende Wirkung hinzuweisen.
- Die Verbindungen der Formel I können den Schmierstoffen auf an sich bekannte Weise beigemischt werden. Die Verbindungen sind beispielsweise in Ölen gut löslich. Es ist auch möglich, einen sogenannten Masterbatch herzustellen, der nach Maßgabe des Verbrauchs auf Einsatzkonzentrationen mit dem entsprechenden Schmierstoff verdünnt werden kann. In solchen Fällen sind auch Konzentrationen über 10 Gew.% möglich.
- Die erfindungsgemäßen Schmierstoffe, Metallbearbeitungs- und Hydraulikflüssigkeiten können zusätzlich andere Additive enthalten, die zugegeben werden, um ihre Grundeigenschaften noch weiter zu verbessern; dazu gehören: weitere Antioxidantien, Metallpassivatoren, Rosinhibitoren, Viskositätsindex-Verbesserer, Stockpunkterniedriger, Dispergienmittel, Detergentien, weitere Hochdruck-Zusätze und Antiverschleiß-Additive.
- Es folgen Beispiele solcher weiteren Zusatzstoffe:
- Beispiele für phenolische Antioxidantien
-
- 1. Alkylierte Monophenole, z.B. 2,6-Di-tert.butyl-4-methylphenol, 2-Tert.butyl-4,6-dimethylphenol, 2,6-Di-tert.butyl-4-ethylphenol, 2,6-Di-tert.butyl-4-n-butylphenol, 2,6-Di-tert.butyl-4-i-butylphenol, 2,6-Di-cyclopentyl-4-methylphenol, 2-(α-Methylcyclohexyl)-4,6-dimethylphenol, 2,6-Di-octadecyl-4-methylphenol, 2,4,6-Tri-cyclohexylphenol, 2,6-Di-tert.butyl-4-methoxymethylphenol, 2,6-Di-nonyl-4-methylphenol, 2,4-Dimethyl-6-(1'-methyl-undec-1'-yl)-phenol, 2,4-Dimethyl-6-(1'-methyl-heptadec-1'-yl)-phenol, 2,4-Dimethyl-6-(1'-methyl-tridec-1'-yl)-phenol und Mischungen davon.
- 2. Alkylthiomethylphenole, z.B. 2,4-Di-octylthiomethyl-6-tert.-butylphenol, 2,4-Di-octylthiomethyl-6-methylphenol, 2,4-Di-octylthiomethyl-6-ethylphenol, 2,6-Di-dodecylthiomethyl-4-nonylphenol.
- 3. Hydrochinone und alkylierte Hydrochinone, z.B. 2,6-Di-tert.butyl-4-methoxyphenol, 2,5-Di-tert.butyl-hydrochinon, 2,5-Di-tert.amyl-hydrochinon, 2,6-Diphenyl-4-octadecyloxyphenol, 2,6-Di-tert.-butyl-hydrochinon, 2,5-Di-tert.-butyl-4-hydroxyanisol, 3,5-Di-tert.-butyl-4-hydroxyanisol, 3,5-Di-tert.-butyl-4-hydroxyphenyl-stearat, Bis-(3,5-di-tert.-butyl-4-hydroxyphenyl)adipat.
- 4. Hydroxylierte Thiodiphenylether, z.B. 2,2'-Thio-bis-(6-tert.-butyl-4-methylphenol), 2,2'-Thio-bis-(4-outylphenol), 4,4'-Thio-bis-(6-tert.butyl-3-methylphenol), 4,4'-Thio-bis-(6-tert.butyl-2-methylphenol), 4,4'-Thio-bis-(3,6-di-sec.-amylphenol), 4,4'-Bis-(2,6-dimethyl-4-hydroxyphenyl)-disulfid.
- 5. Alkyliden-Bisphenole, z.B. 2,2'-Methylen-bis-(6-tert.butyl-4-methylphenol), 2,2'-Methylen-bis-(6-tert.butyl-4-ethylphenol), 2,2'-Methylen-bis-[4-methyl-6-(α-methylcyclohexyl)-phenol], 2,2'-Methylen-bis-(4-methyl-6-cyclohexylphenol), 2,2'-Methylenbis-(6-nonyl-4-methylphenol), 2,2'-Methylen-bis-(4,6-di-tert.butylphenol), 2,2'-Ethyliden-bis-(4,6-di-tert.butylphenol), 2,2'-Ethyliden-bis-(6-tert.butyl-4-isobutylphenol), 2,2'-Methylen-bis-[6-(α-methylbenzyl)-4-nonylphenol], 2,2'-Methylen-bis-[6-(α,α-dimethylbenzyl)-4-nonylphenol], 4,4'-Methylen-bis-(2,6-di-tert.-butylphenol), 4,4'-Methylen-bis-(6-tert.butyl-2-methylphenol), 1,1-Bis-(5-tert.butyl-4-hydroxy-2-methylphenyl)-butan, 2,6-Bis-(3-tent.butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol, 1,1,3- Tris-(5-tert.butyl-4-hydroxy-2-methylphenyl)-butan, 1,1-Bis-(5-tert.butyl-4-hydroxy-2-methyl-phenyl)-3-n-dodecyhnercaptobutan, Ethylenglycol-bis-[3,3-bis-(3'-tert.-butyl-4'-hydroxyphenyl)-butyrat], Bis-(3-tert.butyl-4-hydroxy-5-methyl-phenyl)-dicyclopentadien, Bis-[2-(3'-tert.butyl-2'-hydroxy-5'-methyl-benzyl)-6-tert.butyl-4-methyl-phenyl]-terephthalat, 1,1-Bis-(3,5-dimethyl-2-hydroxyphenyl)-butan, 2,2-Bis-(3,5-di-tert.-butyl-4-hydroxyphenyl)-Propan, 2,2-Bis-(5-tert.-butyl-4-hydroxy-2-methylphenyl)-4-n-dodecylmercapto-butan, 1,1,5,5-Tetra-(5-tert.-butyl-4-hydroxy-2-methylphenyl)-pentan.
- 6. O-, N- und S-Benzylverbindungen, z.B. 3,5,3',5'-Tetra-tert.-butyl-4,4'-dihydroxydibenzylether, Octadecyl-4-hydroxy-3,5-dimethylbenzyl-mercaptoacetat, Tris-(3,5-di-tert.-butyl-4-hydroxybenzyl)-amin, Bis-(4-tert.-butyl-3-hydroxy-2,6-dimethylbenzyl)-dithioterephthalat, Bis-(3,5-di-tert.-butyl-4-hydroxybenzyl)-sulfid, Isooctyl-3,5-di-tert.-butyl-4-hydroxybenzyl-mercaptoacetat.
- 7. Hydroxybenzylierte Malonate, z.B. Dioctadecyl-2,2-bis-(3,5-di-tert.-butyl-2-hydroxybenzyl)-malonat, Di-octadecyl-2-(3-tert.-butyl-4-hydroxy-5-methylbenzyl)-malonat, Didodecylmercaptoethyl-2,2-bis-(3,5-di-tert.-butyl-4-hydroxybenzyl)-malonat, Di-[4-(1,1,3,3-tetramethylbutyl)-phenyl]-2,2-bis-(3,5-di-tert.-butyl-4-hydroxybenzyl)-malonat.
- 8. Hydroxybenzyl-Aromaten, z.B. 1,3,5-Tris-(3,5-di-tert.-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzol, 1,4-Bis-(3,5-di-tert.-butyl-4-hydroxybenzyl)-2,3,5,6-tetramethylbenzol, 2,4,6-Tris-(3,5-di-tert.-butyl-4-hydroxybenzyl)-phenol.
- 9. Triazinverbindungen, z.B. 2,4-Bis-octylmercapto-6-(3,5-di-tert.-butyl-4-hydroxyanilino)-1,3,5-triazin, 2-Octylmercapto-4,6-bis-(3,5-di-tert.-butyl-4-hydroxyanilino)-1,3,5-triazin, 2-Octylmercapto-4,6-bis-(3,5-di-tert.-butyl-4-hydroxyphenoxy) -1,3,5-triazin, 2,4,6-Tris-(3,5-di-tert.-butyl-4-hydroxyphenoxy)-1,2,3-triazi n, 1,3,5-Tris-(3,5-di-tert.-butyl-4-hydroxybenzyl)-isocyanurat, 1,3,5-Tris-(4-tert.-butyl-3-hydroxy-2,6-dimethylbenzyl)-isocyanurat, 2,4,6-Tris-(3,5-di-tert.-butyl-4-hydroxyphenylethyl)-1,3,5-triazin, 1,3,5-Tris-(3,5-di-tert.butyl-4-hydroxyphenylpropionyl)-hexah ydro-1,3,5-triazin, 1,3,5-Tris-(3,5-dicyclohexyl-4-hydroxybenzyl)-isocyanurat.
- 10. Benzylphosphonate, z.B. Dimethyl-2,5-di-tert.-butyl-4-hydroxybenzylphosphonat, Diethyl-3,5-di-tert.-butyl-4-hydroxybenzylphosphonat, Dioctadecyl-3,5-di-tert.-butyl-4-hydroxybenzylphosphonat, Dioctadecyl-5-tert.-butyl-4-hydroxy-3-methylbenzylphos phonat, Ca-Salz des 3,5-Di-tert.-butyl-4-hydroxybenzyl-phosphonsäure-monothylesters.
- 11. Acylaminophenole, z.B. 4-Hydroxy-laurinsäureanilid, 4-Hydroxystearinsäüreanilid, N-(3,5-di-tert.butyl-4-hydroxyphenyl)-carbaminsäureoctylester.
- 12. Ester der β-(3,5-Di-tert.butyl-4-hydroxyphenyl)-propionsäure mit ein- oder mehrwertigen Alkoholen, wie z.B. mit Methanol, Methanol, Octadecanol, 1,6-Hexandiol, 1,9-Nonandiol, Ethylenglycol, 1,2-Propandiol, Neopentylglycol, Thioliethylenglycol, Diethylenglycol, Triethylenglycol, Pentaerythrit, Tris-(hydroxyethyl)-isocyanurat, N,N'-Bis-(hydroxyethyl)-oxalsäurediamid, 3-Thiaundecanol, 3-Thiapentadecanol, Trimethylhexandiol, Trimethylolpropan, 4-Hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]-octan.
- 13. Ester der β-(5-tert.Butyl-4-hydroxy-3-methylphenyl)-propionsäure mit ein- oder mehrwertigen Alkoholen, wie z.B. mit Methanol, Ethanol, Octadecanol, 1,6-Hexandiol, 1,9-Nonandiol, Ethylenglycol, 1,2-Propandiol, Neopentylglycol, Thiodiethylenglycol, Diethylenglycol, Triethylenglycol, Pentaerythrit, Tris-(hydroxy)ethyl-isocyanurat, N,N'-Bis-(hydroxyethyl)-oxalsäurediamid, 3-Thiaundecanol, 3-Thiapentadecanol, Trimethylhexandiol, Trimethylolpropan, 4-Hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]-octan.
- 14. Ester der β-(3,5-Dicyclohexyl-4-hydroxyphenyl)-propionsäure mit ein- oder mehrwertigen Alkoholen, wie z.B. mit Methanol, Ethanol, Octadecanol, 1,6-Hexandiol, 1,9-Nonandiol, Ethylenglycol, 1,2-Propandiol, Neopentylglycol, Thiodiethylenglycol, Diethylenglycol, Triethylenglycol, Pentaerythrit, Tris-(hydroxy)ethyl-isocyanurat, N,N'-Bis-(hydroxyethyl)-oxalsäurediamid, 3-Thiaundecanol, 3-Thiapentadecanol, Trimethylhexandiol, Trimethylolpropan, 4-Hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]-octan.
- 15. Ester der 3,5-Di-tert.-butyl-4-hydroxyphenylessigsäure mit ein- oder mehrwertigen Alkoholen, wie z.B. mit Methanol, Ethanol, Octadecanol, 1,6-Hexandiol, 1,9-Nonandiol, Ethylenglycol, 1,2-Propandiol, Neopentylglycol, Thiodiethylenglycol, Diethylenglycol, Triethylenglycol, Pentaerythrit, Tris-(hydroxy)ethyl-isocyanurat, N,N'-Bis-(hydroxyethyl)-oxalsäurediamid, 3-Thiaundecanol, 3-Thiapentadecanol, Trimethylhexandiol, Trimethylolpropan, 4-Hydroxymethyl-1-phospha-2,6,7-trioxabicyclo-[2.2.2]-octan.
- 16. Amide der β-(3,5-Di-tert.butyl-4-hydroxyphenyl)-propionsäure, wie z.B. N,N'-Bis-(3,5-di-tert.butyl-4-hydroxyphenylpropionyl)-hexamethylendiamin, N,N'-Bis-(3,5-di-tert.-butyl-4-hydroxyphenylpropionyl)-trimethylendiamin, N,N'-Bis-(3,5-di-tert.butyl-4-hydroxyphenylpropionyl)-hydrazin.
- Beispiele für aminische Antioxidantien:
- N,N'-Di-isopropyl-p-phenylendiamin, N,N'-Di-sec-butyl-p-phenylendiamin, N,N'-Bis-(1,4-dimethyl-pentyl)-p-phenylendiamin, N,N'-Bis(1-ethyl-3-methyl-pentyl)-p-phenylendiamin, N,N'-Bis(1-methyl-heptyl)-p-phenylendiamin, N,N'-Dicyclohexyl-p-phenylendiamin, N,N'-Diphenyl-p-phenylendiamin, N,N'-Di-(naphthyl-2)-p-phenylendiamin, N-Isopropyl-N'-phenyl-p-phenylendiamin, N-(1,3-Dimethyl-butyl)-N'-phenyl-p-phenylendiamin, N-(1-Methyl-heptyl)-N'-phenyl-p-phenylendiamin, N-Cyclohexyl-N'-phenyl-p-phenylendiamin, 4-(p-Toluol-sulfonamido)-diphenylamin, N,N'-Dimethyl-N,N'-di-sec-butyl-p-phenylendiamin, Diphenylamin, N-Allyldiphenylamin, 4-Isopropoxy-diphenylamin, N-Phenyl-1-naphthylamin, N-Phenyl-2-naphthylamin, octyliertes Diphenylamin, z.B. p,p'-Di-tert-octyldiphenylamin, 4-n-Butylaminophenol, 4-Butyrylamino-phenol, 4-Nonanoylamino-phenol, 4-Dodecanoylamino-phenol, 4-Octadecanoylamino-phenol, Di-(4-methoxyphenyl)-amin, 2,6-Di-tert-butyl-4-dimethylamino-methylphenol, 2,4'-Diamino-diphenylmethan, 4,4'-Diamino-diphenylmethan, N,N,N',N'-Tetramethyl-4,4'-diamino-diphenylmethan, 1,2-Di-[(2-methyl-phenyl)-amino]-ethan, 1,2-Di(phenylamino)-propan, (o-Tolyl)-biguanid, Di-[4-(1',3'-dimethyl-butyl)-phenyl]amin, tert-octyliertes N-Phenyl-1-naphthylamin, Gemisch aus mono- und dialkylierten tert-Butyl/tert-Octyldiphenylaminen, Gemisch aus mono- und dialkylierten Isopropyl/Isohexyl-diphenylaminen, Gemische aus mono- und dialkylierten tert.-Butyldiphenylaminen, 2,3-Dihydro-3,3-dimethyl-4H-1,4-benzothiazin, Phenothiazin, N-Allylphenothiazin, N,N,N',N'-Tetraphenyl-1,4-diaminobut-2-en, N,N-Bis-(2,2,6,6-tetramethyl-piperidin-4-yl-hexamethylendiamin, Bis-(2,2,6,6-tetramethylpiperidin-4-yl)-sebacat, 2,2,6,6-Tetramethylpiperidin-4-on, 2,2,6,6-Tetramethylpiperidin-4-ol.
- Beispiele für weitere Antioxidantien:
- Aliphatische oder aromatische Phosphite, Ester der Thiodipropionsäure wer der Thiodiessigsäure, oder Salze der Dithiocarbamid- oder Dithiophosphorsäure, 2,2,12,12-Tetramethyl-5,9-dihydroxy-3,7,11-trithiatridecan und 2,2,15,15-Tetramethyl-5,12-dihydroxy-3,7,10,14-tetrathiahexadecan.
- Beispiele für Metall-Desaktivatoren, z.B. für Kupfer, sind:
-
- a) Bentriazole und deren Derivate, z.B. 2-Mercaptobenztriazol, 2,5-Dimercaptobenztriazol, 4- oder 5-Alkylbenztriazole (z.B. Tolutriazol) und deren Derivate, 4,5,6,7-Tetrahydrobenztriazol, 5,5'-Methylenbis-benztriazol; Mannich-Basen von Benztriazol oder Tolutriazol wie 1-[Di(2-ethylhexyl)aminomethyl)-tolutriazol und 1-[Di(2-ethylhexyl)aminomethyl)-benztriazol; Alkoxyalkylbentriazole wie 1-(Nonyloxymethyl)-benztriazol, 1-(1-Butoxyethyl)-bentriazol und 1-(1-Cyclohexyloxybutyl)-tolutriazol.
- b) 1,2,4-Triazole und deren Derivate, z.B. 3-Alkyl(oder Aryl)- 1,2,4-Triazole, Mannich-Basen von 1,2,4-Triazolen wie 1-[Di(2-ethylhexyl)aminomethyl-1,2,4-triazol; Alkoxyalkyl-1,2,4-triazole wie 1-(1-Butoxyethyl-1,2,4-triazol; acylierte 3-Amino-1,2,4-triazole.
- c) Imidazolderivate, z.B. 4,4'-Methylenbis(2-undecyl-5-methylimidazol, Bis[(N-methyl)-imidazol-2-yl]carbinol-octylether.
- d) Schwefelhaltige heterocyclische Verbindungen, z.B. 2-Mercaptobenzthiazol, 2,5-Dimercapto-1,3,4-thiadiazol, 2,5-Dimercaptobenzthiadiazol und deren Derivate; 3,5-Bis[di(2-ethylhexyl)amino-methyl]-1,3,4-thiadiazolin-2-on.
- e) Aminoverbindungen, z.B. Salicyliden-propylendiamin, Salicylaminoguanidin und deren Salze.
- Beispiele für Rost-Inhibitoren sind:
-
- a) Organische Säuren, ihre Ester, Metallsalze, Aminsalze und Anhydride, z.B. Alkyl- und Alkenyl-bernsteinsäuren und deren Partialester mit Alkoholen, Diolen oder ren, PaHydroxycarbonsäurtialamide von Alkyl- und Alkenylbernsteinsäuren, 4-Nonylphenoxyessigsäure, Alkoxy- und Alkoxyethoxycarbonsäuren wie Dodecyloxyessigsäure, Dodecyloxy(ethoxy)-essigsäure und deren Aminsalze, ferner N-Oleoyl-sarcosin, Sorbitan-mono-oleat, Blei-naphthenat, Alkenylbernsteinsäureanhydride, z.B. Dodecenylbernsteinsäure-anhydrid, 2-(2-Carboxyethyl)-1-dodecyl-3-methylglycerin und dessen Salze, insbesondere Na- und Triethanolaminsalze.
- b) Stickstoffhaltige Verbindungen, z.B.: I. Primäre, sekundäre oder teI. riiäre aliphatische oder cycloaliphatische Amine und Amin-Salze von organischen und anorganischen Säuren, z.B. öllösliche Alkylammonium carboxylate, ferner 1-[N,N-bis-(2-hydroxyethyl)amino]-3-(4-nonylphenoxy)propan-2-ol. II. Heterocyclische Verbindungen, z.B.: Substituierie Imidazoline und Oxazoline, 2-Heptadecenyl-1-(2-hydroxyethyl)-imidazolin.
- c) Phosphorhaltige Verbindungen, z.B.: Aminsalze von Phosphorsäurepartialestern oder Phosphonsäurepartialestern, Zinkdialkyldithiophosphate.
- d) Schwefelhaltige Verbindungen, z.B.: Barium-dinonylnaphthalin-sulfonate, Calciumpetroleum-sulfonate, Alkylthio-substituierie aliphatische Carbonsäuren, Ester von aliphatischen 2-Sulfocarbonsäuren und deren Salze.
- e) Glycerinderivate, z.B.: Glycerin-monooleat, 1-(Alkylphenoxy)-3-(2-hydroxyethyl)glycerine, 1-(Alkylphenoxy)-3-(2,3-dihydroxypropyl)glycerine, 2-Carboxyalkyl-1,3-dialkylglycerine.
- Beispiele für Viskositätsindex-Verbesserer sind:
- Polyacrylate, Polymethacrylate, Vinylpyrrolidon/Methacrylat-Copolymere, Polyvinylpynolidone, Polybutene, Olefin-Copolymere, Styrol/Acrylat-Copolymere, Polyether.
- Beispiele für Stockpunkterniedriger sind
- Polymethacrylat, alkylierie Naphthalinderivate.
- Beispiele für Dispergiermittel/Tenside sind:
- Polybutenylbernsteinsäureamide oder -imide, Polybutenylphosphonsäurederivate, basische Magnesium-, Calcium-, und Bariumsulfonate und -phenolate.
- Beispiele für Verschleißschutz-Additive sind:
- Schwefel und/oder Phosphor und/oder Halogen enthaltende Verbindungen, wie geschwefelte Olefine und pflanzliche Oele, Zinkdialkyldithiophosphate, Tritolylphosphat, Tricresylphosphat, chlorierte Paraffine, Alkyl- und Aryldi- und tri-sulfide, Aminsalze von Mono- und Dialkylphosphaten, Aminsalze der Methylphosphonsäure, Diethanolaminomethyltolyltriazol, Di(2-ethylhexyl)aminomethyltolyltriazol, Derivate des 2,5-Dimercapto-1,3,4-thiadiazols, 3-[(Bis-isopropyloxy-phosphinothioyl)thio]-propionsäure ethylester, Triphenylthiophosphat(Triphenylphosphorothioat), Tris(alkylphenyl)phosphorothioate und deren Gemische, (z.B. Tris(isononylphenyl)phosphorothioat), Diphenyl-monononylphenyl-phosphorothioat, Isobutylphenyl-diphenyl-phosphorothioat, Dodecylaminsalz des 3-Hydroxy-1,3-thiaphosphetan-3-oxids, Trithiophosphorsäure-5,5,5-tris[isooctylacetat(2)], Derivate von 2-Mercaptobenzthiazol wie 1-[N,N-Bis(2-ethylhexyl)aminomethyl-2-mercapto-1H-1,3-benzthiazol, Ethoxycarbonyl-5-octyl-dithiocarbamat.
-
- Nach Addition der Dithiophosphorsäure an Acrylsäure bzw. Methacrylsäure wird die entstehende substituierie Carbonsäure mit einem Alkohol A-OH nach konventionellen Methoden veresteri, z.B. unter Zuhilfenahme von para-Toluolsulfonsäure oder Methansulfonsäure als Katalysator und gegebenenfalls Toluol als Schleppmittel.
- Ein Beispiel für eine solche Umsetzung ist das folgende Beispiel 12.
- Alternativ können auch Ester der Dithiophosphorsäure mit Acryl- wer Methacrylsäureestern umgesetzt werden, wie z. B in GB 1,569,730 beschrieben.
- Den folgenden Herstellungsbeispielen sind konkrete Parameter für die Durchführung des im Schema zusammengefaßten Verfahrens zu entnehmen. Diese Beispiele sowie die Anwendungsbeispiele erläutern die Erfindung weiter, ohne sie jedoch zu beschränken. Teile- und Prozentangaben beziehen sich, sofern nicht anders angegeben, auf das Gewicht.
- Beispiel 1:
- Dithiophosphorsäure-O,O-di-isopropyl-S-2-carboxyethylester
- Zu 44.78 (0.2 mol) Di-isopropyl-dithiophosphat werden unter Rühren bei 70°C 15.15 g (0.2 mol) Acrylsäure zusammen mit 0.01 g Hydrochinon im Verlauf von 1.5 h zugetropft. Anschließend wird weitere 6 h bei 70°C gerühri, und die leichtflüchtigen Bestandeile werden im Vakuum (700°C/0.02 mbar/0.5 h) entfernt.
Ausbeute 57.2 g (95%) hellgelbe Flüssigkeit, nD 20: 1.5050, 31P-NMR: 91.4 ppm/H3PO4. - Die nachstehend in Tabelle 1 zusammengefaßten Verbindungen der Beispiele 2 bis 11 werden analog Beispiel 1 hergestellt.
- Beispiel 12:
- Dithiophosphorsäure-O,O-di-isopropyl-S-2-[carbo-2',3'-dihydroxy-propoxy]-ethylester
- Ein Gemisch aus 57.2 g (0.2 Mol) Dithiophosphorsäure-O,O-di-isopropyl-S-2-carboxyethylester gemäß Beispiel 1, 18.79 g (0.2 Mol) Glycerin, 1.9 g p-Toluolsulfonsäure und 150 ml Toluol wird am Wasserabscheider 1 h unter Rückfluß erhitzt. Das erhaltene Produkt wird anschließend mit 50 ml einer 10%igen Natriumsulfatlösung und zweimal mit einer Natriumsulfat (10%)/Natriumcarbonat(5%)-Lösung gewaschen und mit wasserfreiem Natriumsulfat getrocknet. Das Lösungsmittel wird anschließend am Rotationsverdampfer abdestillieri und Lösungsmittelreste im Vakuum (60°C/0.05 mbar/1 h) entfernt.
Ausbeute 64.7 g (90%) farblose Flüssigkeit, nD 20: 1.5153, 31P-NMR: 91.3 ppm/H3PO4. -
- *) An Stelle von Glycerin wird eine äquivalente Menge Glykol eingesetzt.
- Die in der folgenden Tabelle 3 zusammengefaßten Verbindungen der Beispiele 20 bis 27 werden nach dem für Beispiel 12 beschriebenen Verfahren hergestellt, wobei anstelle von Glycerin verschiedene Alkohole R'OH eingesetzt werden.
- Beispiel 28
- SRV-Test
- Zur Prüfung auf verschleiß- und reibungsvermindernde Eigenschaften werden die erfindungsgemäßen Dithiophosphate in ein nichtlegieries Schmieröl eingearbeitet und mit Hilfe des SRV-Gerätes (Schwing-Reib-Verschleiß-Gerät der Firma Optimol, München; vgl. Lubrication Engineering 39 (11) 1982, Advert. Index cover 3, page 729) der Reibungskoeffizient μ bei 100°C und 150 °C bestimmt.
- Bei dieser Methode wird eine oszillierende Kugel (50 Hz) mit einer Kraft von 200 N gegen einen fest eingespannten Metallzylinder gepreßt, auf dem sich das Prüföl befindet.
- Horizontal- und Veriikalkräfte werden mit einem piezoelektrischen Kraftaufnehmer gemessen. Das resultierende Signal wird über einen Ladungsverstärker direkt auf den Schreiber überiragen. Nach Beendigung der Prüfung wird das Querprofil der Verschleißmarke auf dem Metallzylinder mit Hilfe eines Profilometers (TALYSURF 10) gemessen. Die Prüfresultate sind in Tabelle 4 zusammengestellt. Tabelle 4
- *)Additivkonzentration 2% in Mineralöl, Viskosität 139.3 mm2s–1 bei 40°C
- ≠)Querprofil der Verschleißmarke am Zylinder
- Die relativ zum unlegierien Basisöl geringen Verschleiß- und Reibwerie zeigen, daß die zugegebenen Verbindungen verschleißmindernd wirken.
Claims (7)
- Verbindungen der Formel I R1 und R2 unabhängig voneinander C3-C18-Alkyl, C5-C12-Cycloalkyl, C5-C6-Cycloalkyl-methyl, C9-C10-Bicycloalkyl-methyl, C9-C10-Tricycloalkyl-methyl, Phenyl, C7-C24-Alkylphenyl oder zusammenbedeuten, R3 Wasserstoff oder Methyl ist, A für-CH2[CH(OH)]mCH2OH steht, R4 Wasserstoff oder C1-C6-Alkyl ist und R5 einen 5-6-gliedrigen, gesättigten heterozyklischen Ring darstellt, R6 Wasserstoff oder Methyl ist, n eine Zahl von 1 bis 11 und m eine Zahl von 0 bis 4 bedeuten.
- Verbindungen nach Anspruch 1, worin R1 und R2 unabhängig voneinander C3-C18-Alkyl, C5-C6-Cycloalkyl oder C7-C18-Alkylphenyl bedeuten, R5 Tetrahydrofuryl darstellt, n 1 bis 6 ist und m für 0 bis 2 steht.
- Zusammensetzungen enthaltend a) einen Schmierstoff, eine Hydraulik- oder Metallbearbeitungsflüssigkeit und b) mindestens eine Verbindung der Formel I nach Anspruch 1.
- Zusammensetzungen nach Anspruch 3, enthaltend als Komponente b) mindestens eine Verbindung der Formel 1 nach Anspruch 2.
- Zusammensetzungen nach Anspruch 3, worin die Komponente a) ein Schmierstoff ist.
- Zusammensetzungen nach Anspruch 5, worin der Schmierstoff ein Motorenöl ist.
- Zusammensetzungen nach Anspruch 3, die zusätzlich weitere Stabilisatoren wie Antioxidantien, Metall-Desaktivatoren, weitere Hochdruck- und Verschleißschutzzusätze, Stockpunkterniedriger enthalten.
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US (1) | US5362419A (de) |
JP (1) | JP3687051B2 (de) |
KR (1) | KR100274361B1 (de) |
CA (1) | CA2097384C (de) |
DE (1) | DE4317943B4 (de) |
FR (1) | FR2691707B1 (de) |
GB (1) | GB2267495B (de) |
IT (1) | IT1270821B (de) |
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CN1042949C (zh) * | 1996-06-05 | 1999-04-14 | 中国石化兰州炼油化工总厂 | 润滑油组合物 |
DE59703420D1 (de) * | 1996-07-15 | 2001-05-31 | Ciba Sc Holding Ag | Beta-Dithiophosphorylierte Propionsäure in Schmierstoffen |
US6046144A (en) * | 1997-06-02 | 2000-04-04 | R.T. Vanderbilt Co., Inc. | Combination of phosphate based additives and sulfonate salts for hydraulic fluids and lubricating compositions |
EP0903399B1 (de) | 1997-09-18 | 2007-02-14 | Ciba SC Holding AG | Schmierstoffzusammensetzungen mit Thiophosphorsäureestern und Dithiophosphorsäureestern |
MY118653A (en) | 1998-07-16 | 2004-12-31 | Mitsui Chemicals Inc | Addition method of supercritical carbon dioxide, and production process of expanded thermoplastic resin product by making use of the addition method. |
FR2789084B1 (fr) * | 1999-01-28 | 2001-03-09 | Lorraine Laminage | Emulsion d'huile dans l'eau comprenant au moins un additif de lubrification |
JP2001316211A (ja) * | 2000-05-08 | 2001-11-13 | Sumitomo Chem Co Ltd | 害虫による繊維製品の食害を防止する方法及びそのための剤 |
JP4789335B2 (ja) * | 2001-01-04 | 2011-10-12 | 昭和シェル石油株式会社 | 耐摩耗性潤滑油組成物 |
US6534452B1 (en) * | 2001-03-27 | 2003-03-18 | Exxonmobil Research And Engineering Company | Long-life lubricating oil with wear prevention capability |
US20040242437A1 (en) * | 2001-06-14 | 2004-12-02 | Jose Reyes-Gavlian | Antiwear performance of engine oils with $g(b)-dithiophosphorylated propionic acids |
DE10206097A1 (de) * | 2002-02-13 | 2003-08-14 | Basf Ag | Alkoxylierte Acyl- und Bisacylphosphinderivate |
US20040259743A1 (en) * | 2003-06-18 | 2004-12-23 | The Lubrizol Corporation, A Corporation Of The State Of Ohio | Lubricating oil composition with antiwear performance |
JP4582767B2 (ja) * | 2004-03-31 | 2010-11-17 | Jx日鉱日石エネルギー株式会社 | すべり案内面用潤滑油組成物 |
JP4863634B2 (ja) * | 2004-03-25 | 2012-01-25 | Jx日鉱日石エネルギー株式会社 | 潤滑油組成物 |
US8466096B2 (en) * | 2007-04-26 | 2013-06-18 | Afton Chemical Corporation | 1,3,2-dioxaphosphorinane, 2-sulfide derivatives for use as anti-wear additives in lubricant compositions |
JP5199637B2 (ja) * | 2007-10-10 | 2013-05-15 | 昭和シェル石油株式会社 | フルタイム四輪駆動トランスファ用潤滑油組成物 |
JP5965231B2 (ja) * | 2012-07-12 | 2016-08-03 | 出光興産株式会社 | 緩衝器用潤滑油組成物 |
CN113637514A (zh) | 2013-12-06 | 2021-11-12 | 巴斯夫欧洲公司 | 组合物及其形成方法 |
US9090850B1 (en) * | 2014-06-19 | 2015-07-28 | Afton Chemical Corporation | Phosphorus anti-wear compounds for use in lubricant compositions |
CN107001967B (zh) * | 2014-11-04 | 2020-08-21 | Jxtg能源株式会社 | 冷冻机油 |
JP6669343B2 (ja) * | 2015-02-27 | 2020-03-18 | 出光興産株式会社 | 生分解性潤滑油組成物 |
AU2017347968B2 (en) | 2016-10-31 | 2022-01-20 | Afton Chemical Corporation | Phosphorous containing compounds and uses thereof |
JP6951272B2 (ja) * | 2018-02-08 | 2021-10-20 | Eneos株式会社 | 潤滑油用添加剤組成物及び潤滑油組成物 |
CN111057107B (zh) * | 2018-10-16 | 2023-03-10 | 中国石油化工股份有限公司 | 一种硫代膦酸酯化合物及其制备方法、用途 |
CN111057111B (zh) * | 2018-10-16 | 2023-08-15 | 中国石油化工股份有限公司 | 一种硫化硫代膦酸酯化合物及其制备方法、用途 |
US11578287B1 (en) | 2021-12-21 | 2023-02-14 | Afton Chemical Corporation | Mixed fleet capable lubricating compositions |
US11807827B2 (en) | 2022-01-18 | 2023-11-07 | Afton Chemical Corporation | Lubricating compositions for reduced high temperature deposits |
US11970671B2 (en) | 2022-07-15 | 2024-04-30 | Afton Chemical Corporation | Detergent systems for oxidation resistance in lubricants |
US11912955B1 (en) | 2022-10-28 | 2024-02-27 | Afton Chemical Corporation | Lubricating compositions for reduced low temperature valve train wear |
US11926804B1 (en) | 2023-01-31 | 2024-03-12 | Afton Chemical Corporation | Dispersant and detergent systems for improved motor oil performance |
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SE371567B (de) * | 1968-06-19 | 1974-11-25 | Montedison Spa | |
GB1287331A (en) * | 1970-01-29 | 1972-08-31 | Ciba Geigy Uk Ltd | Phosphorodithioic acid esters |
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JPS5745193A (en) * | 1980-09-01 | 1982-03-13 | Nippon Tokushu Noyaku Seizo Kk | Organic phosphoric ester, its preparation and insecticide, acaricide or nematocide containing the same |
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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- 1993-05-12 TW TW082103721A patent/TW279839B/zh active
- 1993-05-26 GB GB9310875A patent/GB2267495B/en not_active Expired - Lifetime
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- 1993-05-28 DE DE4317943A patent/DE4317943B4/de not_active Expired - Lifetime
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- 1993-06-01 JP JP15418293A patent/JP3687051B2/ja not_active Expired - Lifetime
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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 (de) | 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 |
KR100274361B1 (ko) | 2000-12-15 |
ITMI931151A0 (it) | 1993-06-01 |
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