DE1594482A1 - Polyphenyl-aether-Mischungen - Google Patents
Polyphenyl-aether-MischungenInfo
- Publication number
- DE1594482A1 DE1594482A1 DE19641594482 DE1594482A DE1594482A1 DE 1594482 A1 DE1594482 A1 DE 1594482A1 DE 19641594482 DE19641594482 DE 19641594482 DE 1594482 A DE1594482 A DE 1594482A DE 1594482 A1 DE1594482 A1 DE 1594482A1
- Authority
- DE
- Germany
- Prior art keywords
- bis
- preparation according
- ester
- cobalt
- designated
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims description 70
- 229920013636 polyphenyl ether polymer Polymers 0.000 title claims description 36
- -1 neopentyl polyol ester Chemical class 0.000 claims description 48
- 150000002148 esters Chemical class 0.000 claims description 40
- 239000007788 liquid Substances 0.000 claims description 40
- 238000002360 preparation method Methods 0.000 claims description 37
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 26
- 229910017052 cobalt Inorganic materials 0.000 claims description 23
- 239000010941 cobalt Substances 0.000 claims description 23
- SDUQWTDEBSFSIV-UHFFFAOYSA-N 1,2-bis(2-phenoxyphenoxy)benzene Chemical compound C=1C=CC=C(OC=2C(=CC=CC=2)OC=2C(=CC=CC=2)OC=2C=CC=CC=2)C=1OC1=CC=CC=C1 SDUQWTDEBSFSIV-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 239000003963 antioxidant agent Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 229920005862 polyol Polymers 0.000 claims description 12
- 150000004982 aromatic amines Chemical class 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 150000005690 diesters Chemical class 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 4
- 150000001869 cobalt compounds Chemical class 0.000 claims description 4
- UQJDVLPHTXQTRP-UHFFFAOYSA-N 2,2-bis(heptanoyloxymethyl)butyl heptanoate Chemical compound CCCCCCC(=O)OCC(CC)(COC(=O)CCCCCC)COC(=O)CCCCCC UQJDVLPHTXQTRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- FIPTYOFKSOWKTF-UHFFFAOYSA-N 1,2-diphenoxybenzene Chemical class C=1C=CC=C(OC=2C=CC=CC=2)C=1OC1=CC=CC=C1 FIPTYOFKSOWKTF-UHFFFAOYSA-N 0.000 claims 1
- 230000003064 anti-oxidating effect Effects 0.000 claims 1
- RHCQEPWEBDOALW-MUCWUPSWSA-K cobalt(3+);(e)-4-oxopent-2-en-2-olate Chemical compound [Co+3].C\C([O-])=C/C(C)=O.C\C([O-])=C/C(C)=O.C\C([O-])=C/C(C)=O RHCQEPWEBDOALW-MUCWUPSWSA-K 0.000 claims 1
- BKFAZDGHFACXKY-UHFFFAOYSA-N cobalt(II) bis(acetylacetonate) Chemical compound [Co+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O BKFAZDGHFACXKY-UHFFFAOYSA-N 0.000 claims 1
- FCEOGYWNOSBEPV-FDGPNNRMSA-N cobalt;(z)-4-hydroxypent-3-en-2-one Chemical compound [Co].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FCEOGYWNOSBEPV-FDGPNNRMSA-N 0.000 claims 1
- 239000002585 base Substances 0.000 description 27
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 20
- 239000012530 fluid Substances 0.000 description 20
- 239000000314 lubricant Substances 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- 239000007983 Tris buffer Substances 0.000 description 12
- 238000007254 oxidation reaction Methods 0.000 description 11
- 230000003647 oxidation Effects 0.000 description 9
- 238000009472 formulation Methods 0.000 description 8
- 150000002170 ethers Chemical class 0.000 description 7
- 230000001590 oxidative effect Effects 0.000 description 7
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 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
- 230000000694 effects Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 229920001955 polyphenylene ether Polymers 0.000 description 4
- 229940116351 sebacate Drugs 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- KOKDSALTQSQPDH-UHFFFAOYSA-N 1,3-bis(3-phenoxyphenoxy)benzene Chemical compound C=1C=CC(OC=2C=C(OC=3C=C(OC=4C=CC=CC=4)C=CC=3)C=CC=2)=CC=1OC1=CC=CC=C1 KOKDSALTQSQPDH-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000004043 oxo group Chemical group O=* 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- KYSKNYFGWVBAOD-UHFFFAOYSA-N 1,3-bis(4-phenoxyphenoxy)benzene Chemical compound C=1C=C(OC=2C=C(OC=3C=CC(OC=4C=CC=CC=4)=CC=3)C=CC=2)C=CC=1OC1=CC=CC=C1 KYSKNYFGWVBAOD-UHFFFAOYSA-N 0.000 description 2
- QKHCUKLDPPXGFA-UHFFFAOYSA-N 1-phenoxy-2-(2-phenoxyphenoxy)benzene Chemical class C=1C=CC=C(OC=2C(=CC=CC=2)OC=2C=CC=CC=2)C=1OC1=CC=CC=C1 QKHCUKLDPPXGFA-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000004435 Oxo alcohol Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 229940067597 azelate Drugs 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- 238000006864 oxidative decomposition reaction Methods 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- OPTYCEAUVSDMAT-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) heptanoate Chemical compound CCCCCCC(=O)OCC(C)(C)CO OPTYCEAUVSDMAT-UHFFFAOYSA-N 0.000 description 1
- PONXTPCRRASWKW-UHFFFAOYSA-N 1,2-diphenylethane-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)C(N)C1=CC=CC=C1 PONXTPCRRASWKW-UHFFFAOYSA-N 0.000 description 1
- UVGPELGZPWDPFP-UHFFFAOYSA-N 1,4-diphenoxybenzene Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1OC1=CC=CC=C1 UVGPELGZPWDPFP-UHFFFAOYSA-N 0.000 description 1
- CEUKNEYMDJIDAA-UHFFFAOYSA-N 1-(2,3-diphenoxyphenoxy)-2,3-diphenoxybenzene Chemical class C=1C=CC(OC=2C(=C(OC=3C=CC=CC=3)C=CC=2)OC=2C=CC=CC=2)=C(OC=2C=CC=CC=2)C=1OC1=CC=CC=C1 CEUKNEYMDJIDAA-UHFFFAOYSA-N 0.000 description 1
- OCYCLMRWAJCARL-UHFFFAOYSA-N 1-(2-ethoxyphenyl)-n-[4-[(2-ethoxyphenyl)methylideneamino]phenyl]methanimine Chemical compound CCOC1=CC=CC=C1C=NC1=CC=C(N=CC=2C(=CC=CC=2)OCC)C=C1 OCYCLMRWAJCARL-UHFFFAOYSA-N 0.000 description 1
- NDDDKTFZNYMIQO-UHFFFAOYSA-N 1-[2-(2,3-diphenoxyphenoxy)phenoxy]-2,3-diphenoxybenzene Chemical compound C=1C=CC(OC=2C(=CC=CC=2)OC=2C(=C(OC=3C=CC=CC=3)C=CC=2)OC=2C=CC=CC=2)=C(OC=2C=CC=CC=2)C=1OC1=CC=CC=C1 NDDDKTFZNYMIQO-UHFFFAOYSA-N 0.000 description 1
- CHSBGBACAWVJTL-UHFFFAOYSA-N 1-methyl-2,4-diphenoxybenzene Chemical compound C1=C(OC=2C=CC=CC=2)C(C)=CC=C1OC1=CC=CC=C1 CHSBGBACAWVJTL-UHFFFAOYSA-N 0.000 description 1
- XNUCVNNIWMGTFZ-UHFFFAOYSA-N 1-methyl-4-(4-phenoxyphenoxy)benzene Chemical compound C1=CC(C)=CC=C1OC(C=C1)=CC=C1OC1=CC=CC=C1 XNUCVNNIWMGTFZ-UHFFFAOYSA-N 0.000 description 1
- VOSLIUIVGWBSOK-UHFFFAOYSA-N 1-n-phenylbenzene-1,2,4-triamine Chemical compound NC1=CC(N)=CC=C1NC1=CC=CC=C1 VOSLIUIVGWBSOK-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- MVCITNPWSJQCBC-UHFFFAOYSA-N 1-phenoxy-3-(3-phenoxyphenoxy)benzene Chemical compound C=1C=CC(OC=2C=C(OC=3C=CC=CC=3)C=CC=2)=CC=1OC1=CC=CC=C1 MVCITNPWSJQCBC-UHFFFAOYSA-N 0.000 description 1
- GMRIWCLJJFNYSC-UHFFFAOYSA-N 1-phenyl-2-(2-phenylphenoxy)benzene Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1OC1=CC=CC=C1C1=CC=CC=C1 GMRIWCLJJFNYSC-UHFFFAOYSA-N 0.000 description 1
- CICDSZCELMNDRA-UHFFFAOYSA-N 10-(2-ethylhexoxy)-10-oxodecanoic acid Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(O)=O CICDSZCELMNDRA-UHFFFAOYSA-N 0.000 description 1
- QQGBDFMKLXCNHD-UHFFFAOYSA-N 2,2-bis(decanoyloxymethyl)butyl decanoate Chemical compound CCCCCCCCCC(=O)OCC(CC)(COC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC QQGBDFMKLXCNHD-UHFFFAOYSA-N 0.000 description 1
- OVCLLFKPSJLUIY-UHFFFAOYSA-N 2-(2-aminoethyliminomethyl)phenolate hydron Chemical compound NCCN=CC1=CC=CC=C1O OVCLLFKPSJLUIY-UHFFFAOYSA-N 0.000 description 1
- FJSNTQXNQNSZJS-UHFFFAOYSA-N 2-(2-nonanoyloxypropoxy)propyl nonanoate Chemical compound CCCCCCCCC(=O)OCC(C)OCC(C)OC(=O)CCCCCCCC FJSNTQXNQNSZJS-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- NQLXFZQLPAVUIO-UHFFFAOYSA-N 2-[(4-aminophenyl)iminomethyl]phenol Chemical compound NC1=CC=C(C=C1)N=CC1=CC=CC=C1O NQLXFZQLPAVUIO-UHFFFAOYSA-N 0.000 description 1
- SGRCVQDBWHCTIS-UHFFFAOYSA-N 2-nonanoyloxypropyl nonanoate Chemical compound CCCCCCCCC(=O)OCC(C)OC(=O)CCCCCCCC SGRCVQDBWHCTIS-UHFFFAOYSA-N 0.000 description 1
- TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical group NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 description 1
- FKHKSWSHWLYDOI-UHFFFAOYSA-N 2-phenylbenzene-1,4-diamine Chemical compound NC1=CC=C(N)C(C=2C=CC=CC=2)=C1 FKHKSWSHWLYDOI-UHFFFAOYSA-N 0.000 description 1
- YGZVAQICDGBHMD-UHFFFAOYSA-N 3-methylhexan-1-ol Chemical compound CCCC(C)CCO YGZVAQICDGBHMD-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- QABJATQYUASJEM-UHFFFAOYSA-N 4,5-dimethylhexan-1-ol Chemical compound CC(C)C(C)CCCO QABJATQYUASJEM-UHFFFAOYSA-N 0.000 description 1
- RHPVVNRNAHRJOQ-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1NC1=CC=C(C)C=C1 RHPVVNRNAHRJOQ-UHFFFAOYSA-N 0.000 description 1
- YNPVNLWKVZZBTM-UHFFFAOYSA-N 4-methylhexan-1-ol Chemical compound CCC(C)CCCO YNPVNLWKVZZBTM-UHFFFAOYSA-N 0.000 description 1
- GFEQMMJEHGAWGE-UHFFFAOYSA-N 4-phenylcyclohexa-1,5-diene-1,4-diamine Chemical compound C1=CC(N)=CCC1(N)C1=CC=CC=C1 GFEQMMJEHGAWGE-UHFFFAOYSA-N 0.000 description 1
- XYHDHXBLSLSXSR-UHFFFAOYSA-N 4-tritylaniline Chemical compound C1=CC(N)=CC=C1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XYHDHXBLSLSXSR-UHFFFAOYSA-N 0.000 description 1
- QSBWXVLIJXZSTM-UHFFFAOYSA-N 5-methyl-2-(4-methylphenyl)aniline Chemical group C1=CC(C)=CC=C1C1=CC=C(C)C=C1N QSBWXVLIJXZSTM-UHFFFAOYSA-N 0.000 description 1
- ZVHAANQOQZVVFD-UHFFFAOYSA-N 5-methylhexan-1-ol Chemical compound CC(C)CCCCO ZVHAANQOQZVVFD-UHFFFAOYSA-N 0.000 description 1
- PMCXYLLOCXBUCH-UHFFFAOYSA-N CC(CN)N=CC1=CC=CC=C1O Chemical compound CC(CN)N=CC1=CC=CC=C1O PMCXYLLOCXBUCH-UHFFFAOYSA-N 0.000 description 1
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 1
- 239000005750 Copper hydroxide Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 102000006835 Lamins Human genes 0.000 description 1
- 108010047294 Lamins Proteins 0.000 description 1
- GBQJRZDKGJNZGJ-UHFFFAOYSA-N NCCCN=CC1=CC=CC=C1O Chemical compound NCCCN=CC1=CC=CC=C1O GBQJRZDKGJNZGJ-UHFFFAOYSA-N 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 238000010752 Ullmann ether synthesis reaction Methods 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- MXNODNKXIIQMMI-UHFFFAOYSA-N [3-decanoyloxy-2,2-bis(decanoyloxymethyl)propyl] decanoate Chemical compound CCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCC)(COC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC MXNODNKXIIQMMI-UHFFFAOYSA-N 0.000 description 1
- AOZDHFFNBZAHJF-UHFFFAOYSA-N [3-hexanoyloxy-2,2-bis(hexanoyloxymethyl)propyl] hexanoate Chemical compound CCCCCC(=O)OCC(COC(=O)CCCCC)(COC(=O)CCCCC)COC(=O)CCCCC AOZDHFFNBZAHJF-UHFFFAOYSA-N 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001279 adipic acids Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- UWNCDRPJANDCBA-UHFFFAOYSA-N bis(2-ethylbutyl) decanedioate Chemical compound CCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CC UWNCDRPJANDCBA-UHFFFAOYSA-N 0.000 description 1
- ZDWGXBPVPXVXMQ-UHFFFAOYSA-N bis(2-ethylhexyl) nonanedioate Chemical compound CCCCC(CC)COC(=O)CCCCCCCC(=O)OCC(CC)CCCC ZDWGXBPVPXVXMQ-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
- WCGZEWNYSULWGU-UHFFFAOYSA-N cobalt(2+) cobalt(3+) Chemical compound [Co+2].[Co+3] WCGZEWNYSULWGU-UHFFFAOYSA-N 0.000 description 1
- JAWGVVJVYSANRY-UHFFFAOYSA-N cobalt(3+) Chemical compound [Co+3] JAWGVVJVYSANRY-UHFFFAOYSA-N 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229910001956 copper hydroxide Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
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Classifications
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- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US276992A US3231499A (en) | 1963-04-30 | 1963-04-30 | Polyphenyl ether blends |
| US277021A US3274107A (en) | 1963-04-30 | 1963-04-30 | Lubricant composition containing a sulfide |
| US277020A US3231497A (en) | 1963-04-30 | 1963-04-30 | Polyphenyl ether blends |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1594482A1 true DE1594482A1 (de) | 1971-06-09 |
Family
ID=27402861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641594482 Pending DE1594482A1 (de) | 1963-04-30 | 1964-04-29 | Polyphenyl-aether-Mischungen |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US3231497A (fr) |
| BE (1) | BE647154A (fr) |
| CH (1) | CH450599A (fr) |
| DE (1) | DE1594482A1 (fr) |
| GB (1) | GB1053062A (fr) |
| NL (1) | NL6404793A (fr) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1047306A (fr) * | 1963-08-07 | |||
| US3409552A (en) * | 1964-04-01 | 1968-11-05 | Chevron Res | Alkyl aryl ether polymers in lubricants |
| US3492229A (en) * | 1966-08-26 | 1970-01-27 | Monsanto Co | Functional fluid compositions |
| US3412028A (en) * | 1966-12-13 | 1968-11-19 | Texaco Inc | Synthetic ester base lubricating composition containing a copper or cobalt acetylacetonate |
| US3455846A (en) * | 1966-12-29 | 1969-07-15 | Monsanto Co | Lubricant compositions |
| US3773665A (en) * | 1971-11-17 | 1973-11-20 | Mobil Oil Corp | Lubricants containing amine antioxidants |
| US4032462A (en) * | 1976-05-24 | 1977-06-28 | Chevron Research Company | Lubricating oil additive composition |
| US4256596A (en) * | 1978-08-07 | 1981-03-17 | The Lubrizol Corporation | Oxidatively coupled hydroxyaromatic compounds and fuels and lubricants containing them |
| JPS59100197A (ja) * | 1982-12-01 | 1984-06-09 | Japan Atom Energy Res Inst | 耐放射線性油 |
| DE3444884A1 (de) * | 1984-12-08 | 1986-06-12 | Bayer Ag, 5090 Leverkusen | Stabilisierte schmierstoffe auf der basis von polyethern |
| CA1272183A (fr) * | 1986-02-04 | 1990-07-31 | Noboru Ishida | Compositions d'huile lubrifiante |
| JPS62277494A (ja) * | 1986-05-27 | 1987-12-02 | Japan Atom Energy Res Inst | 超耐放射線性グリ−ス |
| US5366648A (en) * | 1990-02-23 | 1994-11-22 | The Lubrizol Corporation | Functional fluids useful at high temperatures |
| US6972312B1 (en) * | 1999-08-04 | 2005-12-06 | Hybrid Plastics Llc | Process for the formation of polyhedral oligomeric silsesquioxanes |
| US7553904B2 (en) * | 1999-08-04 | 2009-06-30 | Hybrid Plastics, Inc. | High use temperature nanocomposite resins |
| US7485692B2 (en) | 1999-08-04 | 2009-02-03 | Hybrid Plastics, Inc. | Process for assembly of POSS monomers |
| US7638195B2 (en) * | 1999-08-04 | 2009-12-29 | Hybrid Plastics, Inc. | Surface modification with polyhedral oligomeric silsesquioxanes silanols |
| US6933345B1 (en) | 2000-03-24 | 2005-08-23 | Hybrid Plastics, Llp | Reactive grafting and compatibilization of polyhedral oligomeric silsesquioxanes |
| US7723415B2 (en) | 1999-08-04 | 2010-05-25 | Hybrid Plastics, Inc. | POSS nanostructured chemicals as dispersion aids and friction reducing agents |
| US20060194919A1 (en) * | 1999-08-04 | 2006-08-31 | Lichtenhan Joseph D | Porosity control with polyhedral oligomeric silsesquioxanes |
| US7888435B2 (en) * | 1999-08-04 | 2011-02-15 | Hybrid Plastics, Inc. | Process for continuous production of olefin polyhedral oligomeric silsesquioxane cages |
| US7217683B1 (en) | 2001-09-05 | 2007-05-15 | Blanski Rusty L | Lubrication via nanoscopic polyhedral oligomeric silsesquioxanes |
| US20090085011A1 (en) * | 2003-12-18 | 2009-04-02 | Lichtenhan Joseph D | Neutron shielding composition |
| JP6043870B2 (ja) | 2012-09-14 | 2016-12-14 | 東京応化工業株式会社 | 太陽熱発電システム用熱媒体組成物 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA529741A (fr) * | 1956-08-28 | L. Walters Ernest | Lubrifiant synthetique stabilise | |
| NL44792C (fr) * | 1935-04-11 | |||
| US2138835A (en) * | 1936-06-01 | 1938-12-06 | Atlantic Refining Co | Lubricant |
| US2647824A (en) * | 1949-01-26 | 1953-08-04 | Standard Oil Dev Co | Stabilized compositions containing hydrogenated quinolines with oxidation inhibitors |
| US2551786A (en) * | 1949-04-28 | 1951-05-08 | Du Pont | Stabilization of organic substances |
| US2795550A (en) * | 1954-06-29 | 1957-06-11 | California Research Corp | Lubricating oil compositions |
| NL100929C (fr) * | 1955-03-04 | |||
| US2929786A (en) * | 1956-05-18 | 1960-03-22 | Sinclair Refining Co | Synthetic lubricating oil composition |
| US2957022A (en) * | 1957-04-30 | 1960-10-18 | Exxon Research Engineering Co | Esters of cyclopentane-1, 3-dicarboxylic acid |
| US2993929A (en) * | 1957-05-14 | 1961-07-25 | Victor Chemical Works | Process for preparing phosphonothioic chlorides and phosphinothioic chlorides and newproducts produced by said process |
| US3080321A (en) * | 1957-08-09 | 1963-03-05 | Monsanto Chemicals | Isomeric mixtures of diphenoxy-, ditoloxy-, and phenoxytoloxybenzenes as functional fluids |
| US3006852A (en) * | 1957-12-09 | 1961-10-31 | Shell Oil Co | Lubricating compositions and process of lubrication utilizing certain polyoxyphenylene compounds |
| BE576233A (fr) * | 1958-02-28 | |||
| US2940929A (en) * | 1958-06-26 | 1960-06-14 | Shell Oil Co | High-temperature lubricants |
| US3048608A (en) * | 1959-03-18 | 1962-08-07 | Heyden Newport Chemical Corp | Neopentyl glycol esters |
| US3099682A (en) * | 1959-12-24 | 1963-07-30 | Exxon Research Engineering Co | Preparation, treatment and storage, under a nitrogen blanket, of the diesters of dicarboxylic acids and oxo alcohols |
| US3169925A (en) * | 1961-06-26 | 1965-02-16 | Shell Oil Co | High temperature lubricants and phosphorus containing polymers |
-
0
- GB GB1053062D patent/GB1053062A/en active Active
-
1963
- 1963-04-30 US US277020A patent/US3231497A/en not_active Expired - Lifetime
- 1963-04-30 US US277021A patent/US3274107A/en not_active Expired - Lifetime
- 1963-04-30 US US276992A patent/US3231499A/en not_active Expired - Lifetime
-
1964
- 1964-04-27 BE BE647154D patent/BE647154A/xx unknown
- 1964-04-28 CH CH555964A patent/CH450599A/fr unknown
- 1964-04-29 DE DE19641594482 patent/DE1594482A1/de active Pending
- 1964-04-29 NL NL6404793A patent/NL6404793A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1053062A (fr) | |
| US3231497A (en) | 1966-01-25 |
| BE647154A (fr) | 1964-08-17 |
| US3231499A (en) | 1966-01-25 |
| CH450599A (fr) | 1968-01-31 |
| US3274107A (en) | 1966-09-20 |
| NL6404793A (fr) | 1964-11-02 |
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