US3637557A - Esters of tris(polyalkyleneoxy) isocyanurates - Google Patents
Esters of tris(polyalkyleneoxy) isocyanurates Download PDFInfo
- Publication number
- US3637557A US3637557A US860402A US3637557DA US3637557A US 3637557 A US3637557 A US 3637557A US 860402 A US860402 A US 860402A US 3637557D A US3637557D A US 3637557DA US 3637557 A US3637557 A US 3637557A
- Authority
- US
- United States
- Prior art keywords
- tris
- isocyanurate
- triesters
- acid
- esters
- 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
- 239000007983 Tris buffer Substances 0.000 title abstract description 30
- 150000002148 esters Chemical class 0.000 title description 10
- 150000005691 triesters Chemical class 0.000 abstract description 32
- 239000002253 acid Substances 0.000 abstract description 18
- 230000001050 lubricating effect Effects 0.000 abstract description 12
- 239000012530 fluid Substances 0.000 abstract description 10
- 239000000654 additive Substances 0.000 abstract description 7
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical class OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 33
- -1 undecylenic Chemical group 0.000 description 14
- 125000005702 oxyalkylene group Chemical group 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 235000021314 Palmitic acid Nutrition 0.000 description 6
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid group Chemical group C(CCCCCC)(=O)O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 5
- 239000000314 lubricant Substances 0.000 description 5
- 239000004014 plasticizer Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 2
- 229940073769 methyl oleate Drugs 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-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
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-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
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005069 Extreme pressure additive Substances 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 1
- UIERETOOQGIECD-ARJAWSKDSA-N angelic acid group Chemical group C(\C(\C)=C/C)(=O)O UIERETOOQGIECD-ARJAWSKDSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007866 anti-wear additive Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229940067597 azelate Drugs 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 230000000332 continued effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000011551 heat transfer agent Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid group Chemical group C(CCCCC)(=O)O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 239000012768 molten material Substances 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003336 secondary aromatic amines Chemical class 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid group Chemical group C(\C(\C)=C\C)(=O)O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 1
- ATVLVRVBCRICNU-UHFFFAOYSA-N trifluorosilicon Chemical class F[Si](F)F ATVLVRVBCRICNU-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- PVNIQBQSYATKKL-UHFFFAOYSA-N tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2618—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen
- C08G65/2621—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups
- C08G65/263—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups containing heterocyclic amine groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
- C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
-
- 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
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/025—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with condensed rings
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
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Definitions
- Triesters of tris(hydropolyoxyalkylene)isocyanurates and alkanoic or alkenoic acid are fluid over a Wide temperature range.
- the products are useful in functional fluid and lubricating applications, such as lubricating additives to gasoline.
- This invention relates to novel isocyanurate derivatives, and in particular to esters of tris(hydropolyoxyalkylene)- isocyanurates.
- novel compounds of the instant invention are triesters of an alkanoic or alkenoic acid containing up to 18 carbon atoms and a tris(hydropolyoxyalkylene)isocyanurate of the formula R1-N N-Ra wherein R is an hydroxyl-terminated polyalkyleneoxy chain containing from 2 to oxyalkylene units, and R and R are each an hydroxyl-terminated oxyalkylene chain containing from 1 to 10 oxyalkylene units, each oxyalkylene unit containing from 2 to 4 carbon atoms.
- R is an hydroxyl-terminated polyalkyleneoxy chain containing from 2 to oxyalkylene units
- R and R are each an hydroxyl-terminated oxyalkylene chain containing from 1 to 10 oxyalkylene units, each oxyalkylene unit containing from 2 to 4 carbon atoms.
- the triesters of the instant invention are prepared from tris(2 hydroxyalkyl)isocyanurate alkylene oxide adducts which, in turn, are prepared by acid-catalyzed reaction of tris(2 hydroxyalkyl)isocyanurate with alkylene oxide.
- Preferred triesters are those derived from ethoxyla- 3,637,557 Patented Jan.
- the triesters are prepared by reaction of the isocyanurate under esterification conditions with an alkanoic or alkenoic acid containing up to 18 carbon atoms, e.g., acetic, propionic, butyric, valeric, hexanoic, heptanoic, octanoic, nonanoic, decanoic, undecanoic, lauric, tridecanoic, tetradecanoic, penta-decanoic, hexadecanoic, heptadecanoic, stearic, trimethylacetic, methylpropionic, ethylhexanoic, acrylic, methacrylic, vinylacetic, 'y-methylvinylacetic, 'y-ethylvinylacetic, fl,'y-dimethylvinylacetic, 'ygy-dimethylvinylacetic, crotonic, 'y-methylcrotonic, 'ye
- esters Any of the usual procedures employed for synthesis of esters can be employed whereby the isocyanurate is reacted with the acid or acid-generating derivative, preferably in the presence of catalyst and under conditions conducive to removal of water (or of alcohol if an ester is employed as reactant).
- the reactants are typically charged to a reaction vessel equipped with stirring and heating means.
- an acid catalyst such as sulfuric, hydrochloric, p-toluene sulfonic, ethane sulfonic, chloroacetic, boron and silicon trifluorides, monosodium sulfate, aluminum sulfate, zinc sulfate, boron trifiuoride etherate, aluminum chloride, zinc chloride, aluminum alkoxides, alkyl titanates, etc.
- the amount of acid catalyst employed will vary with the particular reactants, catalyst and conditions, usually within the range of about 0.1-5% by Weight of reactants.
- the instant invention encompasses unsymmetrical triesters, wherein the chains are esterified with different acids, and mixtures of the various esters.
- the unsymmetrical esters are prepared in a relatively pure manner by reacting the isocyanurate successively with one equivalent of each of the desired acids per hydroxyl equivalent.
- the mixtures are prepared either by blending the individual triesters together or by reacting the isocyanurate simultaneously with a mixture of the desired acids. The latter method is preferred to obtain the mixture of unsymmetrical triesters.
- H 2 Decanoate Decanoate Decanoate Decanoate.
- esters of hydroxyalkylated derivatives of tris(2-hydroxypropyl)isocyanurate and tris( Z-hydroxybutyl) isocyanurate are also included within the scope of the instant invention.
- reaction of tris(Z-hydroxyethyl)isocyanurate with an equimolar mixture of ethylene oxide, 1,2-propylene oxide and 1,2-butylene oxide, followed by esterification with an acid selected from among those disclosed hereinbefore affords a product within the scoe of the instant invention.
- Preferred triesters of the instant invention include the triheptanoate, tridecanoate, tripalmitate and trioleate esters of tris(hydroxypropyloxyethylisocyanurate and of tris(hydroxyethyloxyethyl)isocyanurate.
- the compounds of the instant invention typically have pour points of less than 0 C., often less than 20 C., and are thermally stable at temperatures in excess of about 250 C., often in excess of 300 C.
- triesters are useful in a variety of applications due to their fluidity over a wide temperature range, thermal stability and compatibility with other materials. They are advantageously employed in lubricant applications, e.g., as mold release agents, lubricating additives in liquid hydrocarbon compositions, textile lubricants, and components of synthetic greases. They may be used for this purpose either individually or in admixture with each other or in admixture with other lubricants in a major or minor proportion.
- lubricants with which they can be used in admixture include di-2-ethylhexyl sebacate, di-isoctyl azelate, hindered esters of pentaerythritol, trimethylolethane and trimethylolpropane and alkanoic acids having a chain length of 4-12 carbon atoms, polyphenyl ethers, silicone fluids, triaryl phosphate esters, polyglycol ethers, boron esters and the like.
- antioxidants e.g., secondary aromatic amines such as phenothiazine, phenylnaphthylamine, diphenylamine, dialkyldiphenylamine, alkylphenothiazine, alkylphenylnaphthylamine and hindered phenolics
- anti-wear/ extreme pressure additives e.g., tricresyl phosphate, chlorine or sulfur-containing phosphate esters, and chlorinated diphenyl
- metal passivators e.g., benzotriazole and derivatives thereof, other triazoles and salts of salicylol aminoguanidine as copper passivators, and quinizarin as lead passivator
- foam inhibitors e.g., silicons.
- the instant triesters When employed as lubricating additives in liquid hydrocarbon compositions, e.g., gasoline, jet fuel, kerosene and the like, they are incorporated therein to the extent of about 0.001-5 percent by weight. When used in this manner, the instant triesters are especially advantageous in that they have detergency properties as well as lubricating.
- liquid hydrocarbon compositions e.g., gasoline, jet fuel, kerosene and the like
- the fluidity and thermal stability characteristics of the triesters render them valuable in functional fluid applications, especially as heat transfer agents, brake fluids and in other hydraulic fluid applications. They can be used alone for this purpose or as a component in compositions employed heretofore with which they are compatible.
- the triesters are also useful as plasticizers in various resinous systems, e.g., in cellulose and vinyl resins. Compatibility in the different resins will vary with structure of the specific triester, and will depend upon the length of the oxyalkylene chains, the selection of alkanoate and/or alkenoate moiety(ies), and the specific oxyalkylene units in the chains. Once compatibility is determined by simple experimentation, the triester is incorporated in the resin of interest according to techniques which are generally familiar in the art, e.g., by blending the powdered resin with plasticizer by mixing and/0r kneading to obtain uniform distribution and then curing the mix.
- the proportion of triester employed in this manner will vary over a great range depending upon the efliciency of the particular triester as a plasticizer, whether additional plasticizers and other modifying agents are employed, and the final degree of plasticization desired. The latter factor is dependent upon the ultimate application intended for the resin, i.e., whether it is to be fabricated into a relatively rigid or highly flexible article. With these factors in mind, one skilled in the art will utilize a plasticizing amount of the triesters, which amount will typically lie within the range of about 5-125, especially 35-100, parts of plasticizer per parts resin.
- Tris(hydropolyoxyalkylene)isocyanurates used in the preparation of the instant triesters are prepared by acidcatalyzed reaction of tris(2-hydroxyethyl)isocyanurates with alkylene oxide.
- the reaction may be conducted in a solvent, such as trialkylisocyanurate, N-methylpyrrolidone, acetone, etc., but is preferably conducted in the absence of solvent.
- the tris(2-hydroxyalkyl)isocyanurate is heated above its melting point and the alkylene oxide is bubbled through the molten material.
- An etherification-type catalyst is used in the reaction, e.g., sulfuric acid, phosphoric acid, boron trifluoride and its hydrates and etherates, trichloroacetic acid, aromatic sulfonic acids, etc.
- 75 g. of tris(2-hydroxyethyl)isocyanurate and 0.8 g. of concentrated sulfuric acid are charged into a 300 ml. stainless steel autoclave fitted with a stirrer. The charge is fused at 135 C. and liquid ethylene oxide is passed therethrough under nitrogen pressure ranging between 10 and 60 p.s.i.g. After maintaining the temperature at 134-140 C. for 2-3 hours, 77 g. of ethylene oxide are absorbed to afford a symmetrically oxyethylated isocyanurate having 3 oxyethylene units in each chain.
- Example III The procedure of Example II was repeated substituting for said palmitic acid an equivalent amount of decanoic acid to afford the decanoic acid triester of tris(hydroxypropyloxyethyl)isocyanurate, which had pour point of --25 C. and was thermally stable beyond 300 C.
- Example IV The procedure of Example II was repeated substituting for said palmitic acid an equivalent amount of heptanoic acid to afford the heptanoic acid triester of tris(hydroxypropyloxyethyl)isocyanurate, which had pour point of 2l C. and was soluble in unleaded premium stock gasoline at-room temperature at least to the extent of 1 weight percent.
- a compound selected from the triesters of claim 1 wherein said iso cyanurate is of the formula wherein x is an integer from 2 to 10, and y and z are each an integer from 1 to 10.
- a compound selected from the triesters of claim 1 wherein said isocyanurate is of the formula onzomo omon O H wherein at is an integer from 1 to 9, and y and z are each an integer from 0 to 9.
Abstract
TRIESTERS OF TRIS(HYDROPOLYOXYALKYLENE)ISOCYANURATES AND ALKANOIC OR ALKENOIC ACID ARE FLUID OVER A WIDE TEMPERATURE RANGE. THE PRODUCTS ARE USEFUL IN FUNCTIONAL FLUID AND LUBRICATING APPLICATIONS, SUCH AS LUBRICATING ADDITIVES TO GASOLINE.
Description
United States Patent O US. Cl. 260-248 NS 10 Claims I .1 mm.
ABSTRACT OF THE DISCLOSURE Triesters of tris(hydropolyoxyalkylene)isocyanurates and alkanoic or alkenoic acid are fluid over a Wide temperature range. The products are useful in functional fluid and lubricating applications, such as lubricating additives to gasoline.
BACKGROUND OF THE INVENTION This invention relates to novel isocyanurate derivatives, and in particular to esters of tris(hydropolyoxyalkylene)- isocyanurates.
Due to increasingly strenuous operating conditions to which they are subjected, materials employed in lubricating and functional fluid applications have had to conform to more stringent requirements with respect to viscosity index, pour point, thermal stability, etc. Additionally, it is often necessary that lubricating materials be increasingly compatible in various compositions in which they are to be employed, e.g., as lubricating additives in gasoline and other liquid hydrocarbon compositions. Isocyanurate derivatives have been utilized in such applications because of their excellent thermal stability, but these compounds have often been found to be inadequate in other respects, especially with respect to their solubility and low temperature fluidity characteristics.
SUMMARY OF THE INVENTION The novel compounds of the instant invention are triesters of an alkanoic or alkenoic acid containing up to 18 carbon atoms and a tris(hydropolyoxyalkylene)isocyanurate of the formula R1-N N-Ra wherein R is an hydroxyl-terminated polyalkyleneoxy chain containing from 2 to oxyalkylene units, and R and R are each an hydroxyl-terminated oxyalkylene chain containing from 1 to 10 oxyalkylene units, each oxyalkylene unit containing from 2 to 4 carbon atoms. These materials have improved pour points and solubility characteristics, rendering them useful in lubricating and functional fluid applications, such as lubricating additives to gasoline and other liquid hydrocarbon compositions.
DETAILED DESCRIPTION OF THE INVENTION The triesters of the instant invention are prepared from tris(2 hydroxyalkyl)isocyanurate alkylene oxide adducts which, in turn, are prepared by acid-catalyzed reaction of tris(2 hydroxyalkyl)isocyanurate with alkylene oxide. Preferred triesters are those derived from ethoxyla- 3,637,557 Patented Jan. 25, 1972 ice tion or propoxylation of tris(Z-hydroxyethyl)isocyanurate and are of the formula wherein R is hydrogen or methyl; x is an integer from 1-9 and y and z are each an integer from 0 to 9; and R R and R are each an alkanoate or alkenoate moiety containing up to 18 carbon atoms. Especially preferred are those triesters wherein x, y and z are each 1.
The triesters are prepared by reaction of the isocyanurate under esterification conditions with an alkanoic or alkenoic acid containing up to 18 carbon atoms, e.g., acetic, propionic, butyric, valeric, hexanoic, heptanoic, octanoic, nonanoic, decanoic, undecanoic, lauric, tridecanoic, tetradecanoic, penta-decanoic, hexadecanoic, heptadecanoic, stearic, trimethylacetic, methylpropionic, ethylhexanoic, acrylic, methacrylic, vinylacetic, 'y-methylvinylacetic, 'y-ethylvinylacetic, fl,'y-dimethylvinylacetic, 'ygy-dimethylvinylacetic, crotonic, 'y-methylcrotonic, 'yethylcrotonic, flyy-dimethylcrotonic, 'y,'y-dimethylcrotonic, cinnamic, angelic, tiglic, undecylenic, sorbic, oleic, isooleic, petroselenic, linoleic, linolenic, eleostearic, erucic, licanic, parinaric, ricinoleic, palmitoleic and vaccenic. Any of the usual procedures employed for synthesis of esters can be employed whereby the isocyanurate is reacted with the acid or acid-generating derivative, preferably in the presence of catalyst and under conditions conducive to removal of water (or of alcohol if an ester is employed as reactant). The reactants are typically charged to a reaction vessel equipped with stirring and heating means. When the free acid is employed as reactant it is often not necessary to use additional catalyst, but when an acid-generating derivative is employed, e.g., ester or anhydride, it is usually preferred to use an acid catalyst such as sulfuric, hydrochloric, p-toluene sulfonic, ethane sulfonic, chloroacetic, boron and silicon trifluorides, monosodium sulfate, aluminum sulfate, zinc sulfate, boron trifiuoride etherate, aluminum chloride, zinc chloride, aluminum alkoxides, alkyl titanates, etc. The amount of acid catalyst employed will vary with the particular reactants, catalyst and conditions, usually within the range of about 0.1-5% by Weight of reactants.
The relative amounts of isocyanurate and alkanoic or alkenoic acid may vary over a broad range, but it is preferred to employ at least about 1.0 equivalent of acid per hydroxyl equivalent of isocyanurate, more preferably about 1.2 equivalents of acid. The reaction will be con tinued until the amount of water (or alcohol) removed indicates that the isocyanurate is approximately fully esterified.
In addition to the symmetrical triesters wherein each oxyalkylene chain of the isocyanurate is esterified with the same alkanoic or alkenoic acid, the instant invention encompasses unsymmetrical triesters, wherein the chains are esterified with different acids, and mixtures of the various esters. The unsymmetrical esters are prepared in a relatively pure manner by reacting the isocyanurate successively with one equivalent of each of the desired acids per hydroxyl equivalent. The mixtures are prepared either by blending the individual triesters together or by reacting the isocyanurate simultaneously with a mixture of the desired acids. The latter method is preferred to obtain the mixture of unsymmetrical triesters.
Included among the novel triesters of the instant invention are the following compounds:
R I, y, 2 R4 R5 R6 H 1 Acetate Acetate Acetate. H 1 Prpi0nate Propionate Propionate. H 1 Butyrate Butyrate Butyrate. H 1 Valeratc Valerate Valerate. H 1 Hexanoate. Hexanoate Hexanoate. H 1 2-etl1yl- 2-ethylhexanoate Z-ethylhexanoate.
hexanoate. H 2 Decanoate Decanoate Decanoate. H 4 Laurate. CH 1 Stcarate. CH 1 Acrylate. CH; 6 Crotonate. CH 6 Sorbate. CH 6 Oleate. CH3 9 Butyrate CzH 1 0ctanoate Decanoate Laurate 2H5 1 Oleate do Oleate. 0211 1 Valerate Heptanoate Nonanoate. 02115 3 Vinylacetate Trimethyl- Trimethylacetate. acetate. H 9 Cinnamate Cinnamate Cinnamate. H 9 Stearate. H 1 Decanoate. H 1 D0.
Also included within the scope of the instant invention are esters of hydroxyalkylated derivatives of tris(2-hydroxypropyl)isocyanurate and tris( Z-hydroxybutyl) isocyanurate, as well as derivatives wherein the oxyalkylene chains on the cyanuric acid ring are not of identical length and/or are not composed of identical oxyalkylene units. Thus, reaction of tris(Z-hydroxyethyl)isocyanurate with an equimolar mixture of ethylene oxide, 1,2-propylene oxide and 1,2-butylene oxide, followed by esterification with an acid selected from among those disclosed hereinbefore, affords a product within the scoe of the instant invention.
Preferred triesters of the instant invention include the triheptanoate, tridecanoate, tripalmitate and trioleate esters of tris(hydroxypropyloxyethylisocyanurate and of tris(hydroxyethyloxyethyl)isocyanurate.
The compounds of the instant invention typically have pour points of less than 0 C., often less than 20 C., and are thermally stable at temperatures in excess of about 250 C., often in excess of 300 C.
These triesters are useful in a variety of applications due to their fluidity over a wide temperature range, thermal stability and compatibility with other materials. They are advantageously employed in lubricant applications, e.g., as mold release agents, lubricating additives in liquid hydrocarbon compositions, textile lubricants, and components of synthetic greases. They may be used for this purpose either individually or in admixture with each other or in admixture with other lubricants in a major or minor proportion. Other lubricants with which they can be used in admixture include di-2-ethylhexyl sebacate, di-isoctyl azelate, hindered esters of pentaerythritol, trimethylolethane and trimethylolpropane and alkanoic acids having a chain length of 4-12 carbon atoms, polyphenyl ethers, silicone fluids, triaryl phosphate esters, polyglycol ethers, boron esters and the like.
Additives used in connection with the instant compounds in lubricant applications include antioxidants, e.g., secondary aromatic amines such as phenothiazine, phenylnaphthylamine, diphenylamine, dialkyldiphenylamine, alkylphenothiazine, alkylphenylnaphthylamine and hindered phenolics; anti-wear/ extreme pressure additives, e.g., tricresyl phosphate, chlorine or sulfur-containing phosphate esters, and chlorinated diphenyl; metal passivators, e.g., benzotriazole and derivatives thereof, other triazoles and salts of salicylol aminoguanidine as copper passivators, and quinizarin as lead passivator; and foam inhibitors, e.g., silicons.
When the instant triesters are employed as lubricating additives in liquid hydrocarbon compositions, e.g., gasoline, jet fuel, kerosene and the like, they are incorporated therein to the extent of about 0.001-5 percent by weight. When used in this manner, the instant triesters are especially advantageous in that they have detergency properties as well as lubricating.
The fluidity and thermal stability characteristics of the triesters render them valuable in functional fluid applications, especially as heat transfer agents, brake fluids and in other hydraulic fluid applications. They can be used alone for this purpose or as a component in compositions employed heretofore with which they are compatible.
The triesters are also useful as plasticizers in various resinous systems, e.g., in cellulose and vinyl resins. Compatibility in the different resins will vary with structure of the specific triester, and will depend upon the length of the oxyalkylene chains, the selection of alkanoate and/or alkenoate moiety(ies), and the specific oxyalkylene units in the chains. Once compatibility is determined by simple experimentation, the triester is incorporated in the resin of interest according to techniques which are generally familiar in the art, e.g., by blending the powdered resin with plasticizer by mixing and/0r kneading to obtain uniform distribution and then curing the mix. The proportion of triester employed in this manner will vary over a great range depending upon the efliciency of the particular triester as a plasticizer, whether additional plasticizers and other modifying agents are employed, and the final degree of plasticization desired. The latter factor is dependent upon the ultimate application intended for the resin, i.e., whether it is to be fabricated into a relatively rigid or highly flexible article. With these factors in mind, one skilled in the art will utilize a plasticizing amount of the triesters, which amount will typically lie within the range of about 5-125, especially 35-100, parts of plasticizer per parts resin.
Tris(hydropolyoxyalkylene)isocyanurates used in the preparation of the instant triesters are prepared by acidcatalyzed reaction of tris(2-hydroxyethyl)isocyanurates with alkylene oxide. The reaction may be conducted in a solvent, such as trialkylisocyanurate, N-methylpyrrolidone, acetone, etc., but is preferably conducted in the absence of solvent. In the latter method, the tris(2-hydroxyalkyl)isocyanurate is heated above its melting point and the alkylene oxide is bubbled through the molten material. An etherification-type catalyst is used in the reaction, e.g., sulfuric acid, phosphoric acid, boron trifluoride and its hydrates and etherates, trichloroacetic acid, aromatic sulfonic acids, etc. According to a typical procedure for the preparation of the tris(hydropolyoxyalkylene)isocyanurate, 75 g. of tris(2-hydroxyethyl)isocyanurate and 0.8 g. of concentrated sulfuric acid are charged into a 300 ml. stainless steel autoclave fitted with a stirrer. The charge is fused at 135 C. and liquid ethylene oxide is passed therethrough under nitrogen pressure ranging between 10 and 60 p.s.i.g. After maintaining the temperature at 134-140 C. for 2-3 hours, 77 g. of ethylene oxide are absorbed to afford a symmetrically oxyethylated isocyanurate having 3 oxyethylene units in each chain.
The following examples are provided to illustrate the instant invention more fully. They are are provided for illustrative purposes only and are not to be construed as limiting the invention, which is defined by the appended claims.
EXAMPLE I Into a reaction vessel were charged 294 g. of methyl oleate, g. of tris(hydroxypropyloxyethyl)isocyanurate and 2 ml. of tetraisopropyl titanate. The reaction mixture was heated to 210 C. under nitrogen until 25 ml. of methanol was removed, after which time it was heated under 1.5 mm. Hg pressure to remove unreacted methyl oleate and afford the oleic acid triester of tris(hydroxypropyloxyethyl)isocyanurate [Compound II: R=CH x=y=z:1; R =R =R =oleate] which had pour point of 29 C. and Was thermally stable beyond 300 C.
EXAMPLE II To 384 g. of palmitic acid and 217g. of tris(hydroxypropyloxyejthyl)isocyanurate in a round bottom flask equipped with stirrer and Dean-Stark'trap were added 60 ml. of toluene and 0.05 g. of p-toluenesulfonic acid. The reaction mixture was refluxed at 180 C. until 27 ml. of water were collected and then excess toluene was removed by vacuum to afford the palmitic acid triester of tris (hydroxypropyloxyethyl)isocyanurate, which was soluble in unleaded premium stock gasoline at room temperature at least to the extent of 1 weight percent.
EXAMPLE III The procedure of Example II was repeated substituting for said palmitic acid an equivalent amount of decanoic acid to afford the decanoic acid triester of tris(hydroxypropyloxyethyl)isocyanurate, which had pour point of --25 C. and was thermally stable beyond 300 C.
EXAMPLE IV The procedure of Example II was repeated substituting for said palmitic acid an equivalent amount of heptanoic acid to afford the heptanoic acid triester of tris(hydroxypropyloxyethyl)isocyanurate, which had pour point of 2l C. and was soluble in unleaded premium stock gasoline at-room temperature at least to the extent of 1 weight percent.
EXAMPLE V The procedure of Example II is repeated substituting for said palmitic acid an equivalent amount of the following alkanoic and/or alkenoic acid(s) to afford the corresponding triesters of tris(hydroxypropyloxyethyl) isocyanurate The procedure of Examples I-V are repeated substituting for said tris(hydroxypropyloxyethyl)isocyanurate an equivalent amount of the following tris(hydropolyoxyalkylene)isocyanurates to afford the corresponding triesters thereof:
R k y 2 H 1 1 1 H 1 0 0 CH3 1 0 0 H 3 3 3 H 9 9 9 CzHs 1 1 1 C9115 2 2 2 What is claimed is:
1. A compound selected from the triesters of an alkanoic or alkenoic acid containing up to 18 carbon atoms and a tris(hydropolyoxyalkylene)isocyanurate of the formula I R: wherein R is a hydrogen-terminated polyoxyalkylene chain of from 2 to 10 oxyalkylene units, and R and R are each a hydrogen-terminated oxyalkylene chain of from 1 to 10 oxyalkylene units, each oxyalkylene unit independently having the formula CH2CHO I i wherein R is hydrogen, methyl or ethyl.
2. A compound selected from the triesters of claim 1 wherein said iso cyanurate is of the formula wherein x is an integer from 2 to 10, and y and z are each an integer from 1 to 10.
3. A compound selected from the triesters of claim 2 wherein x, y and z are each 2.
4. A compound selected from the triesters of claim 1 wherein said isocyanurate is of the formula onzomo omon O H wherein at is an integer from 1 to 9, and y and z are each an integer from 0 to 9.
5. A compound selected from the triesters of claim 4 wherein x, y and; are each 1.
6. A compound selected from the triesters of the formula wherein R at each occurrence is hydrogen, methyl or ethyl, R R and R independently are selected from residues of alkanoic and alkenoic acids containing up to 18 carbon atoms, x is an integer from 1-9 and y and z are each integers from 0-9.
7 8 7. The heptanoic acid triester of tris(hydroxypropy1oxy- References Cited g lg i wdt t it (h d 1 UNITED STATES PATENTS e ecano1c ac1 rles er 0 ns y roxypropy oxyethynisocyanuratel 3,448,084 6/ 1969 Burdlck et a1 260-248 X 9. The palmitic acid triester of tris(hydroxypropyloxy- 5 JOHN M. FORD, Primary Examiner ethyDiSOcyanurate.
10. The oleic acid triester of tris (hydroxypropyloxyethyl)isocyanurate. 260302
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US86040269A | 1969-09-23 | 1969-09-23 |
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US3637557A true US3637557A (en) | 1972-01-25 |
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US860402A Expired - Lifetime US3637557A (en) | 1969-09-23 | 1969-09-23 | Esters of tris(polyalkyleneoxy) isocyanurates |
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Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3783150A (en) * | 1970-11-13 | 1974-01-01 | Allied Chem | Monofunctionally-blocked tris (2-hydroxyalkyl) isocyanurates and polyestes thereof |
US3870716A (en) * | 1971-03-22 | 1975-03-11 | Allied Chem | Process for production of alkylene oxide adducts of iris(2-hydroxyalkyl)isocyanurate |
EP0010452A1 (en) * | 1978-10-25 | 1980-04-30 | Olin Corporation | Tris-(polyalkoxyalkylated) isocyanurate compounds and their use as functional fluids |
US4262119A (en) * | 1978-10-25 | 1981-04-14 | Olin Corporation | Tris-(polyalkoxylated), isocyanurates |
EP0242925A2 (en) * | 1986-04-21 | 1987-10-28 | The Nisshin Oil Mills, Ltd. | Cold-rolling oils for steel plates |
US4855334A (en) * | 1983-07-26 | 1989-08-08 | Dainippon Ink And Chemicals, Inc. | Curable resin composition and its use |
US20080119592A1 (en) * | 2006-11-17 | 2008-05-22 | Basf Corporation | Plasticizing component and a curable coating composition including the same |
US20140163165A1 (en) * | 2011-07-29 | 2014-06-12 | Evonik Degussa Gmbh | Low molecular weight products and use thereof as reversible or permanent low-temperature crosslinking agent in diels-alder reactions |
-
1969
- 1969-09-23 US US860402A patent/US3637557A/en not_active Expired - Lifetime
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3783150A (en) * | 1970-11-13 | 1974-01-01 | Allied Chem | Monofunctionally-blocked tris (2-hydroxyalkyl) isocyanurates and polyestes thereof |
US3870716A (en) * | 1971-03-22 | 1975-03-11 | Allied Chem | Process for production of alkylene oxide adducts of iris(2-hydroxyalkyl)isocyanurate |
EP0010452A1 (en) * | 1978-10-25 | 1980-04-30 | Olin Corporation | Tris-(polyalkoxyalkylated) isocyanurate compounds and their use as functional fluids |
US4260505A (en) * | 1978-10-25 | 1981-04-07 | Olin Corporation | Tris-(polyalkoxyalkylated) isocyanurate compounds and their use as functional fluids |
US4262119A (en) * | 1978-10-25 | 1981-04-14 | Olin Corporation | Tris-(polyalkoxylated), isocyanurates |
US4855334A (en) * | 1983-07-26 | 1989-08-08 | Dainippon Ink And Chemicals, Inc. | Curable resin composition and its use |
EP0242925A3 (en) * | 1986-04-21 | 1988-08-17 | The Nisshin Oil Mills, Ltd. | Cold-rolling oils for steel plates |
EP0242925A2 (en) * | 1986-04-21 | 1987-10-28 | The Nisshin Oil Mills, Ltd. | Cold-rolling oils for steel plates |
US4889648A (en) * | 1986-04-21 | 1989-12-26 | The Nisshin Oil Mills, Ltd. | Cold-rolling oils for steel plates |
US20080119592A1 (en) * | 2006-11-17 | 2008-05-22 | Basf Corporation | Plasticizing component and a curable coating composition including the same |
US7772304B2 (en) * | 2006-11-17 | 2010-08-10 | Basf Corporation | Plasticizing component and a curable coating composition including the same |
CN101600769B (en) * | 2006-11-17 | 2012-08-08 | 巴斯夫公司 | A plasticizing component and a curable coating composition including the same |
US20140163165A1 (en) * | 2011-07-29 | 2014-06-12 | Evonik Degussa Gmbh | Low molecular weight products and use thereof as reversible or permanent low-temperature crosslinking agent in diels-alder reactions |
US10030105B2 (en) * | 2011-07-29 | 2018-07-24 | Evonik Degussa Gmbh | Low molecular weight products and use thereof as reversible or permanent low-temperature crosslinking agent in Diels-Alder reactions |
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