CA2594153A1 - Use of polyethylene glycol esters of fatty acids as lubricants for plastics - Google Patents
Use of polyethylene glycol esters of fatty acids as lubricants for plastics Download PDFInfo
- Publication number
- CA2594153A1 CA2594153A1 CA002594153A CA2594153A CA2594153A1 CA 2594153 A1 CA2594153 A1 CA 2594153A1 CA 002594153 A CA002594153 A CA 002594153A CA 2594153 A CA2594153 A CA 2594153A CA 2594153 A1 CA2594153 A1 CA 2594153A1
- Authority
- CA
- Canada
- Prior art keywords
- lubricants
- acid
- fatty acids
- esters
- fatty
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 48
- 239000000194 fatty acid Substances 0.000 title claims abstract description 48
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 48
- 239000000314 lubricant Substances 0.000 title claims abstract description 47
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 43
- 239000002202 Polyethylene glycol Substances 0.000 title claims abstract description 11
- 229920001223 polyethylene glycol Polymers 0.000 title claims abstract description 11
- 150000002334 glycols Chemical class 0.000 title claims abstract description 10
- 229920003023 plastic Polymers 0.000 title description 14
- 239000004033 plastic Substances 0.000 title description 14
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 18
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 238000012545 processing Methods 0.000 claims abstract description 9
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 239000004610 Internal Lubricant Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 description 23
- 150000002148 esters Chemical class 0.000 description 18
- 229920005862 polyol Polymers 0.000 description 16
- -1 fatty acid esters Chemical class 0.000 description 15
- 150000002191 fatty alcohols Chemical class 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
- 235000021355 Stearic acid Nutrition 0.000 description 8
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 8
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 8
- 150000003077 polyols Chemical class 0.000 description 8
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 7
- 239000008117 stearic acid Substances 0.000 description 7
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 6
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 6
- 239000004800 polyvinyl chloride Substances 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 5
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 5
- 239000004164 Wax ester Substances 0.000 description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 description 5
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 150000002763 monocarboxylic acids Chemical class 0.000 description 5
- UTOPWMOLSKOLTQ-UHFFFAOYSA-N octacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 description 5
- 235000019386 wax ester Nutrition 0.000 description 5
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 4
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 4
- 239000004386 Erythritol Substances 0.000 description 4
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 239000004605 External Lubricant Substances 0.000 description 4
- 229930195725 Mannitol Natural products 0.000 description 4
- 235000021314 Palmitic acid Nutrition 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 4
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 4
- 235000019414 erythritol Nutrition 0.000 description 4
- 229940009714 erythritol Drugs 0.000 description 4
- 239000003925 fat Substances 0.000 description 4
- 235000019197 fats Nutrition 0.000 description 4
- SIOLDWZBFABPJU-UHFFFAOYSA-N isotridecanoic acid Chemical compound CC(C)CCCCCCCCCC(O)=O SIOLDWZBFABPJU-UHFFFAOYSA-N 0.000 description 4
- 239000000594 mannitol Substances 0.000 description 4
- 235000010355 mannitol Nutrition 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000000344 soap Substances 0.000 description 4
- 239000000600 sorbitol Substances 0.000 description 4
- 235000010356 sorbitol Nutrition 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N 1-Tetradecanol Natural products CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 3
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- 235000021357 Behenic acid Nutrition 0.000 description 3
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 3
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- GWFGDXZQZYMSMJ-UHFFFAOYSA-N Octadecansaeure-heptadecylester Natural products CCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCCCC GWFGDXZQZYMSMJ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- BXWNKGSJHAJOGX-UHFFFAOYSA-N n-hexadecyl alcohol Natural products CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 3
- GLDOVTGHNKAZLK-UHFFFAOYSA-N n-octadecyl alcohol Natural products CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 3
- NKBWPOSQERPBFI-UHFFFAOYSA-N octadecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCCCC NKBWPOSQERPBFI-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- CUXYLFPMQMFGPL-WPOADVJFSA-N (9Z,11E,13E)-octadeca-9,11,13-trienoic acid Chemical compound CCCC\C=C\C=C\C=C/CCCCCCCC(O)=O CUXYLFPMQMFGPL-WPOADVJFSA-N 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 2
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 2
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 2
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 2
- AOHAPDDBNAPPIN-UHFFFAOYSA-N 3-Methoxy-4,5-methylenedioxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC2=C1OCO2 AOHAPDDBNAPPIN-UHFFFAOYSA-N 0.000 description 2
- AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 2
- 229940116226 behenic acid Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 238000003490 calendering Methods 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 2
- MQKMBXOZOISLIV-UHFFFAOYSA-N dioctadecyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCCCCCCCCCC MQKMBXOZOISLIV-UHFFFAOYSA-N 0.000 description 2
- 229960000735 docosanol Drugs 0.000 description 2
- QKPJNZCOIFUYNE-UHFFFAOYSA-N docosyl octadec-9-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCC=CCCCCCCCC QKPJNZCOIFUYNE-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- LQJBNNIYVWPHFW-QXMHVHEDSA-N gadoleic acid Chemical compound CCCCCCCCCC\C=C/CCCCCCCC(O)=O LQJBNNIYVWPHFW-QXMHVHEDSA-N 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 2
- XMHIUKTWLZUKEX-UHFFFAOYSA-N hexacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O XMHIUKTWLZUKEX-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 229960004488 linolenic acid Drugs 0.000 description 2
- 230000004130 lipolysis Effects 0.000 description 2
- 230000001050 lubricating effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000004206 montan acid ester Substances 0.000 description 2
- 235000013872 montan acid ester Nutrition 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- CNVZJPUDSLNTQU-SEYXRHQNSA-N petroselinic acid Chemical compound CCCCCCCCCCC\C=C/CCCCC(O)=O CNVZJPUDSLNTQU-SEYXRHQNSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- BILPUZXRUDPOOF-UHFFFAOYSA-N stearyl palmitate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC BILPUZXRUDPOOF-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 2
- JYKSTGLAIMQDRA-UHFFFAOYSA-N tetraglycerol Chemical compound OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO JYKSTGLAIMQDRA-UHFFFAOYSA-N 0.000 description 2
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
- CFOQKXQWGLAKSK-KTKRTIGZSA-N (13Z)-docosen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCCO CFOQKXQWGLAKSK-KTKRTIGZSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- IKYKEVDKGZYRMQ-PDBXOOCHSA-N (9Z,12Z,15Z)-octadecatrien-1-ol Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCCO IKYKEVDKGZYRMQ-PDBXOOCHSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- DJYWKXYRGAMLRE-QXMHVHEDSA-N (z)-icos-9-en-1-ol Chemical compound CCCCCCCCCC\C=C/CCCCCCCCO DJYWKXYRGAMLRE-QXMHVHEDSA-N 0.000 description 1
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- OQBLGYCUQGDOOR-UHFFFAOYSA-L 1,3,2$l^{2}-dioxastannolane-4,5-dione Chemical compound O=C1O[Sn]OC1=O OQBLGYCUQGDOOR-UHFFFAOYSA-L 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
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- BFGLKTHWZMNGHV-KTKRTIGZSA-N 16-methylheptadecyl (z)-icos-13-enoate Chemical compound CCCCCC\C=C/CCCCCCCCCCCC(=O)OCCCCCCCCCCCCCCCC(C)C BFGLKTHWZMNGHV-KTKRTIGZSA-N 0.000 description 1
- BBBHAOOLZKQYKX-QXMHVHEDSA-N 16-methylheptadecyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCCCCCCCCCCCCCC(C)C BBBHAOOLZKQYKX-QXMHVHEDSA-N 0.000 description 1
- ABEXEQSGABRUHS-UHFFFAOYSA-N 16-methylheptadecyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC(C)C ABEXEQSGABRUHS-UHFFFAOYSA-N 0.000 description 1
- MNAKZOVRDUDCTC-UHFFFAOYSA-N 16-methylheptadecyl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCCCC(C)C MNAKZOVRDUDCTC-UHFFFAOYSA-N 0.000 description 1
- SAMYFBLRCRWESN-UHFFFAOYSA-N 16-methylheptadecyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCCCC(C)C SAMYFBLRCRWESN-UHFFFAOYSA-N 0.000 description 1
- PYJQLUORHGLSGS-UHFFFAOYSA-N 16-methylheptadecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCCCC(C)C PYJQLUORHGLSGS-UHFFFAOYSA-N 0.000 description 1
- HCUZVMHXDRSBKX-UHFFFAOYSA-N 2-decylpropanedioic acid Chemical compound CCCCCCCCCCC(C(O)=O)C(O)=O HCUZVMHXDRSBKX-UHFFFAOYSA-N 0.000 description 1
- QJGNSTCICFBACB-UHFFFAOYSA-N 2-octylpropanedioic acid Chemical compound CCCCCCCCC(C(O)=O)C(O)=O QJGNSTCICFBACB-UHFFFAOYSA-N 0.000 description 1
- NZXZINXFUSKTPH-UHFFFAOYSA-N 4-[4-(4-butylcyclohexyl)cyclohexyl]-1,2-difluorobenzene Chemical compound C1CC(CCCC)CCC1C1CCC(C=2C=C(F)C(F)=CC=2)CC1 NZXZINXFUSKTPH-UHFFFAOYSA-N 0.000 description 1
- PBWGCNFJKNQDGV-UHFFFAOYSA-N 6-phenylimidazo[2,1-b][1,3]thiazol-5-amine Chemical compound N1=C2SC=CN2C(N)=C1C1=CC=CC=C1 PBWGCNFJKNQDGV-UHFFFAOYSA-N 0.000 description 1
- 239000004135 Bone phosphate Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 235000021353 Lignoceric acid Nutrition 0.000 description 1
- CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 229920000426 Microplastic Polymers 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- AOXNDJKHXBKZBT-ZZEZOPTASA-N Oleyl behenate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCCCCCCCC\C=C/CCCCCCCC AOXNDJKHXBKZBT-ZZEZOPTASA-N 0.000 description 1
- 235000021319 Palmitoleic acid Nutrition 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- 229920001944 Plastisol Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- SZAMSYKZCSDVBH-CLFAGFIQSA-N [(z)-octadec-9-enyl] (z)-docos-13-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(=O)OCCCCCCCC\C=C/CCCCCCCC SZAMSYKZCSDVBH-CLFAGFIQSA-N 0.000 description 1
- AVIRVCOMMNJIBK-QXMHVHEDSA-N [(z)-octadec-9-enyl] 16-methylheptadecanoate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CCCCCCCCCCCCCCC(C)C AVIRVCOMMNJIBK-QXMHVHEDSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 229940090958 behenyl behenate Drugs 0.000 description 1
- 125000002511 behenyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000071 blow moulding Methods 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- CCQPAEQGAVNNIA-UHFFFAOYSA-N cyclobutane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCC1 CCQPAEQGAVNNIA-UHFFFAOYSA-N 0.000 description 1
- YZFOGXKZTWZVFN-UHFFFAOYSA-N cyclopentane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC1 YZFOGXKZTWZVFN-UHFFFAOYSA-N 0.000 description 1
- FDKLLWKMYAMLIF-UHFFFAOYSA-N cyclopropane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CC1 FDKLLWKMYAMLIF-UHFFFAOYSA-N 0.000 description 1
- UQLDLKMNUJERMK-UHFFFAOYSA-L di(octadecanoyloxy)lead Chemical compound [Pb+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O UQLDLKMNUJERMK-UHFFFAOYSA-L 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- FTHXLHYCFOSQEJ-UHFFFAOYSA-N docosyl 16-methylheptadecanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC(C)C FTHXLHYCFOSQEJ-UHFFFAOYSA-N 0.000 description 1
- SRKUMCYSWLWLLS-UHFFFAOYSA-N docosyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCCCC SRKUMCYSWLWLLS-UHFFFAOYSA-N 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- KCWGHIAGIBAKFB-UHFFFAOYSA-N ethane-1,2-diamine;octadecanoic acid Chemical compound NCCN.CCCCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O KCWGHIAGIBAKFB-UHFFFAOYSA-N 0.000 description 1
- FARYTWBWLZAXNK-WAYWQWQTSA-N ethyl (z)-3-(methylamino)but-2-enoate Chemical compound CCOC(=O)\C=C(\C)NC FARYTWBWLZAXNK-WAYWQWQTSA-N 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- YAQXGBBDJYBXKL-UHFFFAOYSA-N iron(2+);1,10-phenanthroline;dicyanide Chemical compound [Fe+2].N#[C-].N#[C-].C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 YAQXGBBDJYBXKL-UHFFFAOYSA-N 0.000 description 1
- 229940060384 isostearyl isostearate Drugs 0.000 description 1
- 229940113915 isostearyl palmitate Drugs 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 239000012170 montan wax Substances 0.000 description 1
- 229940043348 myristyl alcohol Drugs 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- WRPMUZXHQKAAIC-CZIZESTLSA-N octadecyl (e)-octadec-9-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCC\C=C\CCCCCCCC WRPMUZXHQKAAIC-CZIZESTLSA-N 0.000 description 1
- ZFCUBQOYWAZKNO-ZPHPHTNESA-N octadecyl (z)-docos-13-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCC\C=C/CCCCCCCC ZFCUBQOYWAZKNO-ZPHPHTNESA-N 0.000 description 1
- GAQPWOABOQGPKA-UHFFFAOYSA-N octadecyl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCCCCCC GAQPWOABOQGPKA-UHFFFAOYSA-N 0.000 description 1
- BARWIPMJPCRCTP-UHFFFAOYSA-N oleic acid oleyl ester Natural products CCCCCCCCC=CCCCCCCCCOC(=O)CCCCCCCC=CCCCCCCCC BARWIPMJPCRCTP-UHFFFAOYSA-N 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- ALSTYHKOOCGGFT-MDZDMXLPSA-N oleyl alcohol Chemical compound CCCCCCCC\C=C\CCCCCCCCO ALSTYHKOOCGGFT-MDZDMXLPSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 229940120511 oleyl erucate Drugs 0.000 description 1
- 125000001117 oleyl 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])=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
- BARWIPMJPCRCTP-CLFAGFIQSA-N oleyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC BARWIPMJPCRCTP-CLFAGFIQSA-N 0.000 description 1
- 235000013873 oxidized polyethylene wax Nutrition 0.000 description 1
- LBIYNOAMNIKVKF-FPLPWBNLSA-N palmitoleyl alcohol Chemical compound CCCCCC\C=C/CCCCCCCCO LBIYNOAMNIKVKF-FPLPWBNLSA-N 0.000 description 1
- LBIYNOAMNIKVKF-UHFFFAOYSA-N palmitoleyl alcohol Natural products CCCCCCC=CCCCCCCCCO LBIYNOAMNIKVKF-UHFFFAOYSA-N 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
- 239000002245 particle Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000004999 plastisol Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000010561 standard procedure Methods 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
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- DTOSIQBPPRVQHS-UHFFFAOYSA-N α-Linolenic acid Chemical compound CCC=CCC=CCC=CCCCCCCCC(O)=O DTOSIQBPPRVQHS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
- C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the use of polyethylene glycol esters of fatty acids corresponding to the following formula:
R1-CO-O-(CH2-CH2-O)n-OC-R2 (I) in which R1 and R2 independently of one another represent alkyl groups containing 7 to 23 carbon atoms, which may be saturated or unsaturated, linear or branched, and n is a number of 2 to 50, as lubricants in the processing of thermoplastics.
R1-CO-O-(CH2-CH2-O)n-OC-R2 (I) in which R1 and R2 independently of one another represent alkyl groups containing 7 to 23 carbon atoms, which may be saturated or unsaturated, linear or branched, and n is a number of 2 to 50, as lubricants in the processing of thermoplastics.
Description
Use of Polyethylene Glycol Esters of Fatty Acids as Lubricants for Plastics Field of the Invention This invention relates to the use of polyethylene glycol esters of fatty acids as lubricants for plastics.
Prior Art In the processing of thermoplastics, lubricants are added as processing aids. On the one hand, the lubricants are capable of reducing the internal friction between plastic particles which makes the plastics easier to melt and promotes the formation of a homogeneous, flowable melt. Lubricants acting in this way are also commonly referred to as internal lubricants. On the other hand, lubricants used in the processing of plastics are capable of reducing the adhesion of the plastic melt to hot surfaces of machine parts or to the walls of the molds. It is assumed that the lubricants, which, after their incorporation in the plastic, migrate from the plastic to the surface on account of their limited compatibility, reduce adhesion. Lubricants acting in this way are also known as external lubricants or as "mold release agents".
In principle, the use of the lubricants also has a considerable bearing on the morphology, homogeneity and surface qualities of the plastic products.
Whether an additive acts as internal or external lubricant depends on many factors, more particularly on its structure and on the nature of the plastic. In many cases, internal and external lubricating effects may even be developed alongside one another. Initial observations on lubricants in PVC and their effect as internal and external lubricants can be found in the overview in Gachter/Muller, Kunststoffadditive (2"d Edition, pp. 320-327).
Known lubricants for plastics include, for example, fatty acids, fatty I
alcohols, fatty acid esters, fatty acid complex esters, wax esters, dicarboxylic acid esters, amide waxes, metal soaps, montan waxes, hydrocarbon waxes or oxidized hydrocarbons.
Polyethylene glycol monoesters are used as antistatic and antifogging agents in thermoplastics (cf. Antistatic PVC Materials, Sheverdyaev, O.N. USSR, Plasticheskie Massy (1985), (4), 21-2; ISSN:
0554-2901; in Russian; reported in CAPLUS: 1985:423262).
Description of the Invention The problem addressed by the present invention was to provide lubricants, more especially internal lubricants, which could be used in the processing of thermoplastics.
It has surprisingly been found that polyethylene glycol esters of fatty acids can be used in excellent fashion as lubricants and preferably as internal lubricants in the processing of thermoplastics. The compounds are highly compatible with the polymers and lead during processing to an improvement in the plasticization of the polymer. Another advantage lies in the low inherent volatility of the polyethylene glycol esters of fatty acids.
The lubricants to be used in accordance with the invention are characterized by the following formula:
R1-CO-O-(CH2-CH2-O)n-OC-R2 (I) in which R' and R2 independently of one another represent alkyl groups containing 7 to 23 carbon atoms, which may be saturated or unsaturated, linear or branched, and n is a number of 2 to 50.
Accordingly, the present invention relates to the use of polyethylene glycol esters of fatty acids corresponding to the following formula:
R'-CO-O-(CH2-CH2-O)n-OC-R2 (I) in which R' and R2 independently of one another represent alkyl groups containing 7 to 23 carbon atoms, which may be saturated or unsaturated, linear or branched, and n is a number of 2 to 50, as lubricants in the processing of thermoplastics. In a preferred embodiment, n has a value of 2 to 4.
The term "lubricant" in the context of the present invention denotes lubricants in the broader sense, i.e. external and/or internal lubricants. If a narrower meaning is intended, it is explicitly indicated (i.e. the expression "internal lubricant" is expressly used).
The compounds (I) to be used in accordance with the invention are preferably used in quantities of 0.05 to 5.0 parts by weight, based on the thermoplastic. The range from 0.1 to 2.0 parts by weight is particularly preferred.
Suitable C$_24 fatty acids are both native and synthetic or branched and saturated or unsaturated compounds. The fatty acids may be used in the form of mixtures. Examples of suitable fatty acids are lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselic acid, linoleic acid, linolenic acid, elaeostearic acid, arachic acid, gadoleic acid, behenic acid and erucic acid. Fatty acids containing hydroxyl or keto groups, such as 12-hydroxystearic acid, are also suitable.
Fatty acids such as these can be obtained from naturally occurring fats and oils, for example by lipolysis at elevated temperature and pressure and subsequent separation of the fatty acid mixtures obtained, optionally followed by hydrogenation of the double bonds present. Technical fatty acids are preferably used. Technical fatty acids are generally mixtures of different fatty acids of a certain chain length range with one fatty acid as the main constituent. C12_1$ fatty acids individually or in admixture are preferably used.
Basically, there are no restrictions with regard to the thermoplastics.
Thermoplastics selected from the group consisting of polycarbonates, polyamides, polyesters, polystyrenes and polyvinyl chloride and copolymers thereof are preferred. These thermoplastics may be stabilized, pigmented, filled with fillers or modified.
In a preferred embodiment, the compounds (I) are used as internal lubricants. All that has been said in the foregoing in regard to the use of the compounds (I) as lubricants also applies to their use as internal lubricants.
The compounds (I) to be used in accordance with the invention -where they are used as lubricants or as internal lubricants - may be used as such or in combination with other typical lubricants different from the compounds (I) or other additives for plastics.
Other typical lubricants are C12_24 fatty acids, C12_24 fatty alcohols, esters of C12_24 fatty acids and C12_24 fatty alcohols (so-called wax esters), esters of C12_24 fatty acids and polyhydric alcohols containing 4 to 6 hydroxyl groups (so-called polyol esters), dicarboxylic acid esters of dicarboxylic acids and C12_24 fatty alcohols and complex esters of dicarboxylic acids, polyols and monocarboxylic acids. The standard lubricants mentioned may be used both individually and in admixture with one another.
The following observations apply to the optional other lubricants different from the compounds of formula (I):
= Suitable C12_24 fatty acids are both native and synthetic, linear saturated compounds. If fatty acid mixtures are used, they may contain unsaturated fatty acids. Examples of suitable fatty acids are lauric, tridecanoic, myristic, pentadecanoic, palmitic, margaric, stearic, behenic and lignoceric acid. Fatty acids containing hydroxyl groups, such as 12-hydroxystearic acid, are also suitable. Fatty acids such as these can be obtained from naturally occurring fats and oils, for example through lipolysis at elevated temperature and pressure and subsequent separation of the fatty acid mixtures obtained, optionally followed by hydrogenation of the double bonds present. Technical fatty acids are preferably used here. They are generally mixtures of different fatty acids of a certain chain length range with one fatty acid as the main constituent. C12.18 fatty acids individually or in admixture are preferably used.
Prior Art In the processing of thermoplastics, lubricants are added as processing aids. On the one hand, the lubricants are capable of reducing the internal friction between plastic particles which makes the plastics easier to melt and promotes the formation of a homogeneous, flowable melt. Lubricants acting in this way are also commonly referred to as internal lubricants. On the other hand, lubricants used in the processing of plastics are capable of reducing the adhesion of the plastic melt to hot surfaces of machine parts or to the walls of the molds. It is assumed that the lubricants, which, after their incorporation in the plastic, migrate from the plastic to the surface on account of their limited compatibility, reduce adhesion. Lubricants acting in this way are also known as external lubricants or as "mold release agents".
In principle, the use of the lubricants also has a considerable bearing on the morphology, homogeneity and surface qualities of the plastic products.
Whether an additive acts as internal or external lubricant depends on many factors, more particularly on its structure and on the nature of the plastic. In many cases, internal and external lubricating effects may even be developed alongside one another. Initial observations on lubricants in PVC and their effect as internal and external lubricants can be found in the overview in Gachter/Muller, Kunststoffadditive (2"d Edition, pp. 320-327).
Known lubricants for plastics include, for example, fatty acids, fatty I
alcohols, fatty acid esters, fatty acid complex esters, wax esters, dicarboxylic acid esters, amide waxes, metal soaps, montan waxes, hydrocarbon waxes or oxidized hydrocarbons.
Polyethylene glycol monoesters are used as antistatic and antifogging agents in thermoplastics (cf. Antistatic PVC Materials, Sheverdyaev, O.N. USSR, Plasticheskie Massy (1985), (4), 21-2; ISSN:
0554-2901; in Russian; reported in CAPLUS: 1985:423262).
Description of the Invention The problem addressed by the present invention was to provide lubricants, more especially internal lubricants, which could be used in the processing of thermoplastics.
It has surprisingly been found that polyethylene glycol esters of fatty acids can be used in excellent fashion as lubricants and preferably as internal lubricants in the processing of thermoplastics. The compounds are highly compatible with the polymers and lead during processing to an improvement in the plasticization of the polymer. Another advantage lies in the low inherent volatility of the polyethylene glycol esters of fatty acids.
The lubricants to be used in accordance with the invention are characterized by the following formula:
R1-CO-O-(CH2-CH2-O)n-OC-R2 (I) in which R' and R2 independently of one another represent alkyl groups containing 7 to 23 carbon atoms, which may be saturated or unsaturated, linear or branched, and n is a number of 2 to 50.
Accordingly, the present invention relates to the use of polyethylene glycol esters of fatty acids corresponding to the following formula:
R'-CO-O-(CH2-CH2-O)n-OC-R2 (I) in which R' and R2 independently of one another represent alkyl groups containing 7 to 23 carbon atoms, which may be saturated or unsaturated, linear or branched, and n is a number of 2 to 50, as lubricants in the processing of thermoplastics. In a preferred embodiment, n has a value of 2 to 4.
The term "lubricant" in the context of the present invention denotes lubricants in the broader sense, i.e. external and/or internal lubricants. If a narrower meaning is intended, it is explicitly indicated (i.e. the expression "internal lubricant" is expressly used).
The compounds (I) to be used in accordance with the invention are preferably used in quantities of 0.05 to 5.0 parts by weight, based on the thermoplastic. The range from 0.1 to 2.0 parts by weight is particularly preferred.
Suitable C$_24 fatty acids are both native and synthetic or branched and saturated or unsaturated compounds. The fatty acids may be used in the form of mixtures. Examples of suitable fatty acids are lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselic acid, linoleic acid, linolenic acid, elaeostearic acid, arachic acid, gadoleic acid, behenic acid and erucic acid. Fatty acids containing hydroxyl or keto groups, such as 12-hydroxystearic acid, are also suitable.
Fatty acids such as these can be obtained from naturally occurring fats and oils, for example by lipolysis at elevated temperature and pressure and subsequent separation of the fatty acid mixtures obtained, optionally followed by hydrogenation of the double bonds present. Technical fatty acids are preferably used. Technical fatty acids are generally mixtures of different fatty acids of a certain chain length range with one fatty acid as the main constituent. C12_1$ fatty acids individually or in admixture are preferably used.
Basically, there are no restrictions with regard to the thermoplastics.
Thermoplastics selected from the group consisting of polycarbonates, polyamides, polyesters, polystyrenes and polyvinyl chloride and copolymers thereof are preferred. These thermoplastics may be stabilized, pigmented, filled with fillers or modified.
In a preferred embodiment, the compounds (I) are used as internal lubricants. All that has been said in the foregoing in regard to the use of the compounds (I) as lubricants also applies to their use as internal lubricants.
The compounds (I) to be used in accordance with the invention -where they are used as lubricants or as internal lubricants - may be used as such or in combination with other typical lubricants different from the compounds (I) or other additives for plastics.
Other typical lubricants are C12_24 fatty acids, C12_24 fatty alcohols, esters of C12_24 fatty acids and C12_24 fatty alcohols (so-called wax esters), esters of C12_24 fatty acids and polyhydric alcohols containing 4 to 6 hydroxyl groups (so-called polyol esters), dicarboxylic acid esters of dicarboxylic acids and C12_24 fatty alcohols and complex esters of dicarboxylic acids, polyols and monocarboxylic acids. The standard lubricants mentioned may be used both individually and in admixture with one another.
The following observations apply to the optional other lubricants different from the compounds of formula (I):
= Suitable C12_24 fatty acids are both native and synthetic, linear saturated compounds. If fatty acid mixtures are used, they may contain unsaturated fatty acids. Examples of suitable fatty acids are lauric, tridecanoic, myristic, pentadecanoic, palmitic, margaric, stearic, behenic and lignoceric acid. Fatty acids containing hydroxyl groups, such as 12-hydroxystearic acid, are also suitable. Fatty acids such as these can be obtained from naturally occurring fats and oils, for example through lipolysis at elevated temperature and pressure and subsequent separation of the fatty acid mixtures obtained, optionally followed by hydrogenation of the double bonds present. Technical fatty acids are preferably used here. They are generally mixtures of different fatty acids of a certain chain length range with one fatty acid as the main constituent. C12.18 fatty acids individually or in admixture are preferably used.
= The C12_24 fatty alcohols are mostly linear saturated representatives which may be obtained inter alia from naturally occurring fats and oils by transesterification with methanol, subsequent catalytic hydrogenation of the methyl esters obtained and fractional distillation.
Examples of such fatty alcohols are lauryl, myristyl, cetyl, stearyl and behenyl alcohol. These compounds may be used individually and in admixture with one another. Technical fatty alcohols are preferably used. They are normally mixtures of different fatty alcohols of a limited chain length range in which one particular fatty alcohol is present as the main constituent. Technical C12_1$ fatty alcohol mixtures are preferred.
= Other suitable additional lubricants are wax esters, i.e. esters of C12-24 fatty acids and C12_24 fatty alcohols which preferably correspond to formula (II):
R3CO-OR4 (I I) in which R3CO is a saturated and/or unsaturated acyl group containing 12 to 24 and preferably 12 to 18 carbon atoms and R2 is an alkyl and/or alkenyl group containing 12 to 24 and preferably 12 to 18 carbon atoms. Typical examples are esters of lauric acid, isotridecanoic acid, myristic acid, palmitic acid, paimitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselic acid, linoleic acid, linolenic acid, elaeostearic acid, arachic acid, gadoleic acid, behenic acid and erucic acid and technical mixtures thereof with lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmitoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linoyl alcohol, linolenyl alcohol, elaeostearyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol and brassidyl alcohol and technical mixtures thereof. Preferred wax esters are stearyl palmitate, stearyl stearate, stearyl isostearate, stearyl oleate, stearyl behenate, stearyl erucate, isostearyl palmitate, isostearyl stearate, isostearyl isostearate, isostearyl oleate, isostearyl behenate, isostearyl erucate, oleyl paimitate, oleyl stearate, oleyl isostearate, oleyl oleate, oleyl behenate, oleyl erucate, behenyl paimitate, behenyl stearate, behenyl isostearate, behenyl oleate, behenyl behenate, behenyl oleate and mixtures thereof. Stearyl stearate is particularly preferred as the wax ester. It is important in this regard to bear in mind that stearyl stearate is normally produced from technical starting materials which in turn are mixtures so that the ester is also a mixture.
The esters mentioned may be obtained by known methods of organic synthesis, for example by heating stoichiometric quantities of fatty acid and fatty alcohol to 180-250 C, optionally in the presence of a suitable esterification catalyst, such as tin grindings, and in an inert gas atmosphere, and distilling off the water of reaction.
= Suitable additional lubricants are polyol fatty acid esters, i.e. esters of C12_24 fatty acids and polyols containing 4 to 6 hydroxyl groups. The alcohol component may be selected, above all, from aliphatic polyols containing 4 to 12 carbon atoms, for example erythritol, pentaerythritol, dipentaerythritol, ditrimethylol propane, diglycerol, triglycerol, tetraglycerol, mannitol and sorbitol. These polyol esters may be full esters in which all the hydroxyl groups of the polyol are esterified with fatty acid. However, polyol partial esters containing one or more free hydroxyl groups in the molecule are also suitable. These polyol fatty acid esters may also be obtained by known methods of organic synthesis by esterification of the polyols with stoichiometric or sub-stoichiometric quantities of free fatty acids. Examples of such polyol fatty acid esters are the stearic acid and stearic acid/palmitic acid full esters of erythritol, pentaerythritol and diglycerol, the dilaurates of dipentaerythritol, ditrimethylolpropane, triglycerol, mannitol and sorbitol, the distearates of erythritol, pentaerythritol, dipentaerythritol and tetraglycerol and the so-called sesquiesters of pentaerythritol, dipentaerythritol, mannitol and sorbitol in whose production 1.5 mol fatty acid, more particularly palmitic and/or stearic acid, is used to 1 mol polyol. The polyol fatty acid esters mentioned are generally mixtures simply because of the particular starting materials used.
= Other suitable additional lubricants are complex esters which are also known per se from the prior art. In principle, the complex esters are produced from dicarboxylic acids, polyols and monocarboxylic acids.
The following dicarboxylic acids may be used for the production of the complex esters: oxalic, malonic, succinic, glutaric, adipic, pimelic, suberic, azelaic, sebacic, nonanedicarboxylic, undecanedicarboxylic, eicosanedicarboxylic, maleic, fumaric, citraconic, mesaconic, itaconic, cyclopropanedicarboxylic, cyclobutanedicarboxylic, cyclopentane-dicarboxylic, camphor, hexahydrophthalic, phthalic, terephthalic, isophthalic, naphthalic and diphenyl-o,o'-dicarboxylic acid. The following compounds are generally used as aliphatic polyols containing 2 to 6 hydroxyl groups: ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, 1,4-butanediol, 2,3-butanediol, 1,5-pentanediol, 1,6-hexanediol, glycerol, trimethylolpropane, erythritol, pentaerythritol, dipentaerythritol, xylitol, mannitol and sorbitol. Suitable monocarboxylic acids are linear or branched, synthetic or native acids, for example lauric, myristic, paimitic, margaric, stearic, arachic, behenic, lignoceric, cerotic acid, montanic acid, oleic, elaidic, erucic, linoleic, linolenic and isostearic acid and mixtures of these acids, particularly those obtainable from natural fats and oils. Preferred complex esters are produced from aliphatic dicarboxylic acids containing 4 to 8 carbon atoms, polyols containing 3 or 4 hydroxyl groups and aliphatic monocarboxylic acids containing 14 to 22 carbon atoms. Excellent results are obtained with complex esters of adipic acid, pentaerythritol and monocarboxylic acids containing 14 to 22 carbon atoms.
= According to the invention, other suitable additional lubricants are dicarboxylic acid esters of fatty alcohols containing 12 to 24 carbon atoms. Suitable dicarboxylic acids have already been mentioned by way of example in connection with the complex esters. Suitable fatty acids are the fatty acids already discussed above. Phthalic acid esters, more especially distearyl phthalate, are particularly preferred.
= Other additional lubricants, which may be used individually or in combination, are hydrocarbon waxes melting at temperatures in the range from 70 to 130 C, oxidized polyethylene waxes, a-olefins, ethylenediamine distearate, montanic acid esters of diols, for example ethanediol, 1,3-butanediol and glycerol, mixtures of such montanic acid esters with unesterified montanic acids and metal soaps, more particularly salts of organic monocarboxylic acids with metals of the second main and/or secondary group of the periodic system, such as calcium soaps and zinc soaps.
Accordingly, the present invention also relates to the use of lubricant combinations for thermoplastics containing (a) one or more fatty acid polyethylene glycol esters (I) and (b) one or more additional lubricants (not covered by formula (I)), with the proviso that components (a) and (b) are used in a ratio by weight of 10:90 to 90:10 and preferably in a ratio by weight of 20:80 to 80:20.
The expression "lubricant combinations" applies both to lubricants and to internal lubricants.
In practice, the lubricant mixtures according to the invention are applied by addition to the thermoplastics to be processed in quantities of 0.05 to 5 and more particularly 0.1 to 2 parts by weight to 100 parts by weight of thermoplastic. The lubricant mixtures are preferably added to the melt formed during production of the thermoplastic or are applied to the plastic granules or powder at elevated temperatures.
The thermoplastics may optionally contain additional additives.
Examples of suitable additives are antistatic agents, antifogging agents, antioxidants, UV stabilizers, coupling agents, calendering aids, parting agents, lubricants, plasticizers, perfumes, flame retardants, fillers and agents for increasing heat stability (heat stabilizers).
The thermoplastics may readily be further processed by standard methods, for example by extrusion, pressing, rolling, calendering, sintering, spinning, blow moulding, foaming, injection moulding or processing by the plastisol method.
Examples 1. Production of the lubricants according to the invention Example 1 237 g diethylene glycol (Fluka), 1151 g technical stearic acid (Cognis) and 0.7 g tin(II) oxalate (Goldschmidt) were heated under nitrogen. The esterification reaction began at ca. 170 C with the formation of water. After 3 hours, removal of the water of reaction was continued by application of vacuum, the vacuum being lowered to ca. 15 mbar over a period of 4 hours. The final temperature was 200 C.
The reaction was terminated at an acid value (AV) of <6. The reaction mixture was cooled to 90 C and filtered. Yield 1296 g, AV = 1.6, SV (saponification value) = 184.
Example 2 PEG-600 distearate was produced from 167 g PEG 600 (Fluka) and 147 g technical stearic acid (Cognis) in the same way as in Example 1.
Yield 298 g, AV = 5.9, SV = 102.
2. Production of dry blends Using a Henschel mixer, a dry blend was produced from PVC
powder and various additives (quantity of material = 3 kg, heating temperature = 120 C, subsequent cooling). The compositions are set out in the following Table (the numbers in the Table represent parts by weight).
Examples of such fatty alcohols are lauryl, myristyl, cetyl, stearyl and behenyl alcohol. These compounds may be used individually and in admixture with one another. Technical fatty alcohols are preferably used. They are normally mixtures of different fatty alcohols of a limited chain length range in which one particular fatty alcohol is present as the main constituent. Technical C12_1$ fatty alcohol mixtures are preferred.
= Other suitable additional lubricants are wax esters, i.e. esters of C12-24 fatty acids and C12_24 fatty alcohols which preferably correspond to formula (II):
R3CO-OR4 (I I) in which R3CO is a saturated and/or unsaturated acyl group containing 12 to 24 and preferably 12 to 18 carbon atoms and R2 is an alkyl and/or alkenyl group containing 12 to 24 and preferably 12 to 18 carbon atoms. Typical examples are esters of lauric acid, isotridecanoic acid, myristic acid, palmitic acid, paimitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselic acid, linoleic acid, linolenic acid, elaeostearic acid, arachic acid, gadoleic acid, behenic acid and erucic acid and technical mixtures thereof with lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmitoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linoyl alcohol, linolenyl alcohol, elaeostearyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol and brassidyl alcohol and technical mixtures thereof. Preferred wax esters are stearyl palmitate, stearyl stearate, stearyl isostearate, stearyl oleate, stearyl behenate, stearyl erucate, isostearyl palmitate, isostearyl stearate, isostearyl isostearate, isostearyl oleate, isostearyl behenate, isostearyl erucate, oleyl paimitate, oleyl stearate, oleyl isostearate, oleyl oleate, oleyl behenate, oleyl erucate, behenyl paimitate, behenyl stearate, behenyl isostearate, behenyl oleate, behenyl behenate, behenyl oleate and mixtures thereof. Stearyl stearate is particularly preferred as the wax ester. It is important in this regard to bear in mind that stearyl stearate is normally produced from technical starting materials which in turn are mixtures so that the ester is also a mixture.
The esters mentioned may be obtained by known methods of organic synthesis, for example by heating stoichiometric quantities of fatty acid and fatty alcohol to 180-250 C, optionally in the presence of a suitable esterification catalyst, such as tin grindings, and in an inert gas atmosphere, and distilling off the water of reaction.
= Suitable additional lubricants are polyol fatty acid esters, i.e. esters of C12_24 fatty acids and polyols containing 4 to 6 hydroxyl groups. The alcohol component may be selected, above all, from aliphatic polyols containing 4 to 12 carbon atoms, for example erythritol, pentaerythritol, dipentaerythritol, ditrimethylol propane, diglycerol, triglycerol, tetraglycerol, mannitol and sorbitol. These polyol esters may be full esters in which all the hydroxyl groups of the polyol are esterified with fatty acid. However, polyol partial esters containing one or more free hydroxyl groups in the molecule are also suitable. These polyol fatty acid esters may also be obtained by known methods of organic synthesis by esterification of the polyols with stoichiometric or sub-stoichiometric quantities of free fatty acids. Examples of such polyol fatty acid esters are the stearic acid and stearic acid/palmitic acid full esters of erythritol, pentaerythritol and diglycerol, the dilaurates of dipentaerythritol, ditrimethylolpropane, triglycerol, mannitol and sorbitol, the distearates of erythritol, pentaerythritol, dipentaerythritol and tetraglycerol and the so-called sesquiesters of pentaerythritol, dipentaerythritol, mannitol and sorbitol in whose production 1.5 mol fatty acid, more particularly palmitic and/or stearic acid, is used to 1 mol polyol. The polyol fatty acid esters mentioned are generally mixtures simply because of the particular starting materials used.
= Other suitable additional lubricants are complex esters which are also known per se from the prior art. In principle, the complex esters are produced from dicarboxylic acids, polyols and monocarboxylic acids.
The following dicarboxylic acids may be used for the production of the complex esters: oxalic, malonic, succinic, glutaric, adipic, pimelic, suberic, azelaic, sebacic, nonanedicarboxylic, undecanedicarboxylic, eicosanedicarboxylic, maleic, fumaric, citraconic, mesaconic, itaconic, cyclopropanedicarboxylic, cyclobutanedicarboxylic, cyclopentane-dicarboxylic, camphor, hexahydrophthalic, phthalic, terephthalic, isophthalic, naphthalic and diphenyl-o,o'-dicarboxylic acid. The following compounds are generally used as aliphatic polyols containing 2 to 6 hydroxyl groups: ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, 1,4-butanediol, 2,3-butanediol, 1,5-pentanediol, 1,6-hexanediol, glycerol, trimethylolpropane, erythritol, pentaerythritol, dipentaerythritol, xylitol, mannitol and sorbitol. Suitable monocarboxylic acids are linear or branched, synthetic or native acids, for example lauric, myristic, paimitic, margaric, stearic, arachic, behenic, lignoceric, cerotic acid, montanic acid, oleic, elaidic, erucic, linoleic, linolenic and isostearic acid and mixtures of these acids, particularly those obtainable from natural fats and oils. Preferred complex esters are produced from aliphatic dicarboxylic acids containing 4 to 8 carbon atoms, polyols containing 3 or 4 hydroxyl groups and aliphatic monocarboxylic acids containing 14 to 22 carbon atoms. Excellent results are obtained with complex esters of adipic acid, pentaerythritol and monocarboxylic acids containing 14 to 22 carbon atoms.
= According to the invention, other suitable additional lubricants are dicarboxylic acid esters of fatty alcohols containing 12 to 24 carbon atoms. Suitable dicarboxylic acids have already been mentioned by way of example in connection with the complex esters. Suitable fatty acids are the fatty acids already discussed above. Phthalic acid esters, more especially distearyl phthalate, are particularly preferred.
= Other additional lubricants, which may be used individually or in combination, are hydrocarbon waxes melting at temperatures in the range from 70 to 130 C, oxidized polyethylene waxes, a-olefins, ethylenediamine distearate, montanic acid esters of diols, for example ethanediol, 1,3-butanediol and glycerol, mixtures of such montanic acid esters with unesterified montanic acids and metal soaps, more particularly salts of organic monocarboxylic acids with metals of the second main and/or secondary group of the periodic system, such as calcium soaps and zinc soaps.
Accordingly, the present invention also relates to the use of lubricant combinations for thermoplastics containing (a) one or more fatty acid polyethylene glycol esters (I) and (b) one or more additional lubricants (not covered by formula (I)), with the proviso that components (a) and (b) are used in a ratio by weight of 10:90 to 90:10 and preferably in a ratio by weight of 20:80 to 80:20.
The expression "lubricant combinations" applies both to lubricants and to internal lubricants.
In practice, the lubricant mixtures according to the invention are applied by addition to the thermoplastics to be processed in quantities of 0.05 to 5 and more particularly 0.1 to 2 parts by weight to 100 parts by weight of thermoplastic. The lubricant mixtures are preferably added to the melt formed during production of the thermoplastic or are applied to the plastic granules or powder at elevated temperatures.
The thermoplastics may optionally contain additional additives.
Examples of suitable additives are antistatic agents, antifogging agents, antioxidants, UV stabilizers, coupling agents, calendering aids, parting agents, lubricants, plasticizers, perfumes, flame retardants, fillers and agents for increasing heat stability (heat stabilizers).
The thermoplastics may readily be further processed by standard methods, for example by extrusion, pressing, rolling, calendering, sintering, spinning, blow moulding, foaming, injection moulding or processing by the plastisol method.
Examples 1. Production of the lubricants according to the invention Example 1 237 g diethylene glycol (Fluka), 1151 g technical stearic acid (Cognis) and 0.7 g tin(II) oxalate (Goldschmidt) were heated under nitrogen. The esterification reaction began at ca. 170 C with the formation of water. After 3 hours, removal of the water of reaction was continued by application of vacuum, the vacuum being lowered to ca. 15 mbar over a period of 4 hours. The final temperature was 200 C.
The reaction was terminated at an acid value (AV) of <6. The reaction mixture was cooled to 90 C and filtered. Yield 1296 g, AV = 1.6, SV (saponification value) = 184.
Example 2 PEG-600 distearate was produced from 167 g PEG 600 (Fluka) and 147 g technical stearic acid (Cognis) in the same way as in Example 1.
Yield 298 g, AV = 5.9, SV = 102.
2. Production of dry blends Using a Henschel mixer, a dry blend was produced from PVC
powder and various additives (quantity of material = 3 kg, heating temperature = 120 C, subsequent cooling). The compositions are set out in the following Table (the numbers in the Table represent parts by weight).
Example C1 C2 C3 E3 E4 PVC Evipol SH 6520 (Ineos) 100 100 100 100 100 Pb sulfate, tribasic 2 2 2 2 2 Lead stearate (28% Pb) 0.5 0.5 0.5 0.5 0.5 Calcium stearate 0.5 0.5 0.5 0.5 0.5 Hydrogenated castor oil - 1.0 - - -Distearyl phthalate - - 1.0 - -Lubricant of Example 1 - - 1.0 -Lubricant of Example 2 - - - 1.0 In this Table, Cl to C3 are comparison Examples. In Cl, no lubricant was added. In C2, hydrogenated castor oil was used; it is the most important internal lubricant for PVC bottles (cf. Plastics Additives Handbook, 5th Edition, Hanser Verlag, p. 537). In C3, distearyl phthalate - an internal lubricant for profile extrusion - was used. E4 and E5 represent formulations according to the invention.
3. Production of ribbons The above-mentioned dry blends were extruded to ribbons in a Weber twin-screw extruder (extrusion parameters: screw speed = 15 r.p.m.: temperature = 190 C). The power consumed by the extruder, the machine load (in %), was evaluated as a measure of plasticization. Early plasticization leads to an increase in the machine load. The melt pressure (bar) before the die was used as a measure of lubricant performance. A
low melt pressure signifies a good lubricating effect.
Example Machine load (%) Melt pressure (bar) C 1 48.7 347 C2 56.6 354 C3 46.0 324 E4 51.1 344 E5 57.8 336 Examples E4 and E5 according to the invention led to earlier plasticization (increase in machine load) at a relatively low melt pressure than Comparison Example Cl. Comparison Examples C2 and C3 lead either to better plasticization for an increase in melt pressure or impair plasticization.
3. Production of ribbons The above-mentioned dry blends were extruded to ribbons in a Weber twin-screw extruder (extrusion parameters: screw speed = 15 r.p.m.: temperature = 190 C). The power consumed by the extruder, the machine load (in %), was evaluated as a measure of plasticization. Early plasticization leads to an increase in the machine load. The melt pressure (bar) before the die was used as a measure of lubricant performance. A
low melt pressure signifies a good lubricating effect.
Example Machine load (%) Melt pressure (bar) C 1 48.7 347 C2 56.6 354 C3 46.0 324 E4 51.1 344 E5 57.8 336 Examples E4 and E5 according to the invention led to earlier plasticization (increase in machine load) at a relatively low melt pressure than Comparison Example Cl. Comparison Examples C2 and C3 lead either to better plasticization for an increase in melt pressure or impair plasticization.
Claims (6)
1. Use of polyethylene glycol esters of fatty acids corresponding to the following formula:
R1-CO-O-(CH2-CH2-O)n-OC-R2 (I) in which R1 and R2 independently of one another represent alkyl groups containing 7 to 23 carbon atoms, which may be saturated or unsaturated, linear or branched, and n is a number of 2 to 50, as lubricants in the processing of thermoplastics.
R1-CO-O-(CH2-CH2-O)n-OC-R2 (I) in which R1 and R2 independently of one another represent alkyl groups containing 7 to 23 carbon atoms, which may be saturated or unsaturated, linear or branched, and n is a number of 2 to 50, as lubricants in the processing of thermoplastics.
2. Use claimed in claim 1, wherein n is a number of 2 to 4.
3. Use claimed in claim 1, wherein R1 and R2 independently of one another are saturated alkyl groups containing 7 to 23 carbon atoms.
4. Use claimed in any of claims 1 to 3, wherein the lubricants are used as internal lubricants.
5. Use of lubricant combinations for thermoplastics containing (a) one or more fatty acid polyethylene glycol esters (I) and (b) one or more additional lubricants (not covered by formula (I)), with the proviso that components (a) and (b) are used in a ratio by weight of 10:90 to 90:10 and preferably 20:80 to 80:20.
6. Use claimed in claim 5, the lubricant combinations being used as internal lubricants.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06015123A EP1881025B1 (en) | 2006-07-20 | 2006-07-20 | Use of esters of polyethylenglycol and fatty acids as lubricants for thermoplastic materials |
EP06015123.0 | 2006-07-20 |
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CA2594153A1 true CA2594153A1 (en) | 2008-01-20 |
CA2594153C CA2594153C (en) | 2014-10-28 |
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CA2594153A Expired - Fee Related CA2594153C (en) | 2006-07-20 | 2007-07-20 | Use of polyethylene glycol esters of fatty acids as lubricants for plastics |
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US (1) | US20080051303A1 (en) |
EP (1) | EP1881025B1 (en) |
AT (1) | ATE458024T1 (en) |
CA (1) | CA2594153C (en) |
DE (1) | DE502006006177D1 (en) |
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DE102007027371A1 (en) * | 2007-06-11 | 2008-12-18 | Cognis Oleochemicals Gmbh | A process for preparing a compound having at least one ester group |
DE102007043753A1 (en) * | 2007-09-13 | 2009-03-19 | Cognis Oleochemicals Gmbh | A thermoplastic composition comprising a mold release agent based on an ester of di- or polyglycerols and at least one carboxylic acid |
EP2215200A2 (en) * | 2007-11-20 | 2010-08-11 | Emery Oleochemicals GmbH | Method for producing an organic composition containing an n-nonyl ether |
WO2009065903A2 (en) * | 2007-11-20 | 2009-05-28 | Cognis Oleochemicals Gmbh | Method for the production of an organic composition containing an n-nonyl ester |
DE102008026263A1 (en) * | 2008-06-02 | 2009-12-03 | Emery Oleochemicals Gmbh | Anti-fogging agent based on polyglycerol and native oils |
WO2010020998A2 (en) * | 2008-07-30 | 2010-02-25 | Indian Oil Corporation Limited | A catalyst composition for transesterification of organically/naturally derived oils and fats to produce alkyl esters and process for preparing the same |
DE102008044706A1 (en) * | 2008-08-28 | 2010-03-04 | Emery Oleochemicals Gmbh | Viscosity reducer for polyether polyols |
DE102008059744A1 (en) * | 2008-12-01 | 2010-06-02 | Emery Oleochemicals Gmbh | Lubricant for thermoplastic polymers |
US8911871B2 (en) * | 2010-12-13 | 2014-12-16 | Xerox Corporation | Fuser member |
US8623992B2 (en) * | 2011-04-12 | 2014-01-07 | Xerox Corporation | Polyalkylene glycol ester intermediate transfer members |
CN103420830B (en) * | 2012-05-25 | 2016-04-20 | 丰益(上海)生物技术研发中心有限公司 | The method for selective production of erythritol lipid acid one ester and diester |
DE102012212018A1 (en) | 2012-07-10 | 2014-01-16 | Robert Bosch Gmbh | Binder system for powder injection molding compound |
CN106661766B (en) | 2014-07-08 | 2019-09-06 | 埃默里油脂化学有限公司 | For the charging that can be sintered in 3D printing equipment |
US9732301B2 (en) * | 2014-11-05 | 2017-08-15 | Infineum International Limited | Power transmitting fluids with improved materials compatibility |
US11945940B2 (en) * | 2018-04-23 | 2024-04-02 | Byk-Chemie Gmbh | Filled polyvinyl chloride composition |
US11104859B2 (en) * | 2019-08-12 | 2021-08-31 | The United States Of America, As Represented By The Secretary Of Agriculture | Polyethylene diester viscosity modifiers |
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US3355413A (en) * | 1966-10-14 | 1967-11-28 | Eastman Kodak Co | Polyester fibers resistant to resoiling during laundering |
US4085187A (en) * | 1975-03-27 | 1978-04-18 | Revere Copper And Brass, Inc. | Process for compression rolling of polymeric films |
GB1489717A (en) * | 1975-05-07 | 1977-10-26 | Sapchim Fournier Cimag Sa | Synthetic plastics materials containing lubricating agent |
US4180492A (en) * | 1975-05-07 | 1979-12-25 | Fevrier-Decoisy-Champion | Thiodiglycol dibehenate and method of use |
FR2310377A1 (en) * | 1975-05-07 | 1976-12-03 | Sapchim Fournier Cimag Sa | NEW LUBRICANTS FOR THERMOPLASTIC MATERIALS |
WO2001048084A1 (en) * | 1999-12-27 | 2001-07-05 | Asahi Kasei Kabushiki Kaisha | Polyoxymethylene resin composition |
DE10245623A1 (en) * | 2002-09-30 | 2004-04-08 | Clariant Gmbh | Esters and partial esters from polyhydric alcohols |
DE102004009895B3 (en) * | 2004-02-26 | 2005-07-21 | Cognis Deutschland Gmbh & Co. Kg | Lubricant mixture for thermoplastics contains natural fats, oils and other conventional lubricants for thermoplastics, in specific weight ratios |
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- 2006-07-20 DE DE502006006177T patent/DE502006006177D1/en active Active
- 2006-07-20 AT AT06015123T patent/ATE458024T1/en active
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EP1881025A1 (en) | 2008-01-23 |
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