JPS635437B2 - - Google Patents
Info
- Publication number
- JPS635437B2 JPS635437B2 JP18464683A JP18464683A JPS635437B2 JP S635437 B2 JPS635437 B2 JP S635437B2 JP 18464683 A JP18464683 A JP 18464683A JP 18464683 A JP18464683 A JP 18464683A JP S635437 B2 JPS635437 B2 JP S635437B2
- Authority
- JP
- Japan
- Prior art keywords
- castor oil
- acid
- rolling
- group
- oil
- 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
Links
- 239000004359 castor oil Substances 0.000 claims description 40
- 235000019438 castor oil Nutrition 0.000 claims description 40
- 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 claims description 40
- 239000010731 rolling oil Substances 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 13
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000004593 Epoxy Substances 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 9
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 8
- 239000000194 fatty acid Substances 0.000 claims description 8
- 229930195729 fatty acid Natural products 0.000 claims description 8
- 150000004665 fatty acids Chemical class 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 4
- 239000010775 animal oil Substances 0.000 claims description 4
- 238000005886 esterification reaction Methods 0.000 claims description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 4
- 239000002480 mineral oil Substances 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 4
- 239000008158 vegetable oil Substances 0.000 claims description 4
- 239000005069 Extreme pressure additive Substances 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 2
- 238000005096 rolling process Methods 0.000 description 25
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 239000000463 material Substances 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- 239000003760 tallow Substances 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 235000019482 Palm oil Nutrition 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 239000002540 palm oil Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-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
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-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
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 235000015278 beef Nutrition 0.000 description 2
- KBWLNCUTNDKMPN-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) hexanedioate Chemical compound C1OC1COC(=O)CCCCC(=O)OCC1CO1 KBWLNCUTNDKMPN-UHFFFAOYSA-N 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 229940049964 oleate Drugs 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- 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 1
- WLYVBDOFKMGCBL-DEXHTJMYSA-N (z)-4-[(z)-octadec-9-enoxy]-4-oxobut-2-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)\C=C/C(O)=O WLYVBDOFKMGCBL-DEXHTJMYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-NMQOAUCRSA-N 1,2-dideuteriooxyethane Chemical group [2H]OCCO[2H] LYCAIKOWRPUZTN-NMQOAUCRSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- FKOKUHFZNIUSLW-UHFFFAOYSA-N 2-Hydroxypropyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(C)O FKOKUHFZNIUSLW-UHFFFAOYSA-N 0.000 description 1
- SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 description 1
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 1
- MUHFRORXWCGZGE-KTKRTIGZSA-N 2-hydroxyethyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCO MUHFRORXWCGZGE-KTKRTIGZSA-N 0.000 description 1
- BXCRLBBIZJSWNS-UHFFFAOYSA-N 2-hydroxyethyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCCO BXCRLBBIZJSWNS-UHFFFAOYSA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- 241000283153 Cetacea Species 0.000 description 1
- 229910000669 Chrome steel Inorganic materials 0.000 description 1
- 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 1
- 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 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- TXQVDVNAKHFQPP-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(CO)(CO)CO TXQVDVNAKHFQPP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 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 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- JQDCYGOHLMJDNA-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) butanedioate Chemical compound C1OC1COC(=O)CCC(=O)OCC1CO1 JQDCYGOHLMJDNA-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- MPVXINJRXRIDDB-VCDGYCQFSA-N dodecanoic acid;(2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCCCCCC(O)=O MPVXINJRXRIDDB-VCDGYCQFSA-N 0.000 description 1
- LLRANSBEYQZKFY-UHFFFAOYSA-N dodecanoic acid;propane-1,2-diol Chemical compound CC(O)CO.CCCCCCCCCCCC(O)=O LLRANSBEYQZKFY-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229940093476 ethylene glycol Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229940095098 glycol oleate Drugs 0.000 description 1
- 229940087073 glycol palmitate Drugs 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- CKQVRZJOMJRTOY-UHFFFAOYSA-N octadecanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCCCCCCCCCCCC(O)=O CKQVRZJOMJRTOY-UHFFFAOYSA-N 0.000 description 1
- 229960002969 oleic acid Drugs 0.000 description 1
- 235000021313 oleic acid Nutrition 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
- 238000011056 performance test Methods 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
Description
本発明は、圧延油に関するものである。
従来圧延油として、鋼板用にはパーム油が古く
から使われ、それに代つて牛脂、豚脂、長須鯨硬
化油などの動植物油脂や鉱物油または、それらの
混合油をベースとして、それに添加剤、油性向上
剤、酸化防止剤、界面活性剤などを配合したもの
が広く使われている。
一方、圧延機械設備の進歩は著しく進み、ミル
の大型化に伴い、パス回数の削減、圧延速度の高
速化、圧延製品の規格精度の上昇等の圧延工程の
合理化並びに精密化が要求され、それに伴い圧延
油にかかる条件も苛酷なものとなつて来ており、
パーム油や牛脂系圧延油では、最早この条件を満
足し得ないものとなりつつあるが未だこれに代る
圧延油が見出されていないのが現状である。
本発明は、従来のパーム油や牛脂系の圧延油よ
りすぐれた潤滑性能を有し、現在の要求されてい
る苛酷な圧延工程に対して、満足し得る圧延油を
提供せんとするものである。
本発明の圧延油は次の様なものより構成され
る。
(A)群としてヒマシ油、または水素添加したヒマ
シ油(以下水添ヒマシ油と記す)
(B)群としてアルキレンオキサイドを付加したヒ
マシ油、またはアルキレンオキサイドを付加した
水添ヒマシ油
(C)群として(A)または(B)のヒドロキシル基の一部
を、炭素数12以上の脂肪酸にてエステル化して得
られるヒマシ油誘導体
(D)群として炭素数11以上のアルキルまたはアル
ケニル基をもつたヒドロキシ化合物とジカルボン
酸とから得られるジカルボン酸モノエステルのカ
ルボキシル基と、(A)または(B)のヒドロキシル基の
一部とのエステル化反応によつて得られるヒマシ
油誘導体
上記(A),(B),(C),(D)の4群より選ばれたる少く
とも1種と分子中にグリシジル基を2または3ケ
有する多価エポキシ化合物との反応によつて得ら
れる反応生成物を主要成分とし、そのまま、また
は必要に応じ、それに動植物油脂、鉱物油、界面
活性剤、極圧添加剤等を混合して用いることを特
徴とする金属圧延油に関するものである。
本発明における水添ヒマシ油は常法によりヒマ
シ油の水素添加により得られる。またアルキレン
オキサイドを付加したヒマシ油またはアルキレン
オキサイドを付加した水添ヒマシ油は常法により
ヒマシ油または水添ヒマシ油にアルキレンオキサ
イドを付加して得られる。アルキレンオキサイド
としては炭素数2〜3のものを2〜100モル付加
して用いられる。
さらに(A)または(B)と、炭素数12以上の脂肪酸と
反応して得られるヒマシ油誘導体(以下ヒマシ油
誘導体(C)と称す)も一般に知られるエステル化反
応によつて得られる。すなわち、本発明に用いる
ヒマシ油誘導体(C)は、(A)または(B)に結合するヒド
ロキシル基と上記脂肪酸との脱水エステル化反応
により得るか、(A)または(B)と上記脂肪酸の低級エ
ステルとのエステル交換反応によつても得ること
が出来る。ただし、このヒマシ油誘導体(C)は反応
終了時において、ヒマシ油誘導体(C)分子中に少く
とも1ケのヒドロキシル基を残存することが必須
条件であり、(A)または(B)1モルに対し上記脂肪酸
0.5〜2モルを反応して得られる。
本発明のヒマシ油誘導体(C)を得るに用いる炭素
数12以上の脂肪酸としては、ラウリン酸、ミリス
チン酸、パルミチン酸、ステアリン酸、アラキン
酸、ベヘン酸等の飽和脂肪酸、ネオ酸、オキソ法
により得られる脂肪酸等の側鎖飽和脂肪酸、オレ
イン酸、リノール酸、リノレン酸、アラキドン
酸、リシノール酸等の不飽和脂肪酸が挙げられ
る。
つぎに、炭素数11以上のアルキルまたはアルケ
ニル基を有するヒドロキシ化合物とジカルボン酸
とから得られるジカルボン酸モノエステルに、(A)
または(B)を反応して得られるヒマシ油誘導体(以
下ヒマシ油誘導体(D)と称す)は、ヒマシ油誘導体
(C)と同様に、(A)または(B)1モルに対し、上記ジカ
ルボン酸モノエステル0.5〜2モルを反応して得
られ、ヒマシ油誘導体(D)は分子中に少くとも1ケ
のヒドロキシル基を残存することが必須条件であ
る。
またヒマシ油誘導体(D)を得るに用いるジカルボ
ン酸モノエステルは炭素数11以上のアルキルまた
はアルケニル基を有するヒドロキシ化合物とジカ
ルボン酸をモル比にて1:1で反応して得られる
化合物で、その分子中にカルボキシル基を1ケ有
する。炭素数11以上のアルキルまたはアルケニル
基を有するヒドロキシ化合物としては、ラウリル
アルコール、パルミチルアルコール、セタノー
ル、ステアリルアルコール、オレイルアルコー
ル、エチレングリコールオレエート、プロピレン
グリコールラウレート、プロピレングリコールス
テアレート、ポリエチレングリコールパルミテー
ト、ポリエチレングリコールオレエート、グリセ
リンステアレート、ソルビトールラウレート、ソ
ルビトールオレエート、ペンタエリスリトールス
テアレート等およびこれらのヒドロキシ化合物に
アルキレンオキサイドを付加しものが挙げられ、
ジカルボン酸としてはコハク酸、アジピン酸、ア
ゼライン酸、セバシン酸、マレイン酸、フマール
酸、イタコン酸等の二塩基性カルボン酸さらに不
飽和脂肪酸を重合して得られるいわゆるダイマー
酸が挙げられる。
次に(A),(B),(C),(D)の4群より選ばれたる少く
とも1種と多価エポキシ化合物との反応生成物
は、前記(A),(B),(C),(D)の4群より選ばれたる少
くとも1種と分子中にグリシジル基を2また3ケ
有する多価エポキシ化合物との反応によつて常法
に従つて合成される。すなわち(A)〜(D)群の化合物
に結合するヒドロキシル基への多価エポキシ化合
物の付加反応によるもので、(A)〜(D)群より選ばれ
たる少くとも1種1モルに対し、多価エポキシ化
合物0.3〜2モルの比率にて、70〜120℃で反応し
て得られ、(A)〜(D)群の化合物が多価エポキシ化合
物により架橋され、鎖状または網目状の反応生成
物を生じる。
本発明に用いる分子中にグリシジル基を2また
は3ケ有する多価エポキシ化合物としては、エチ
レングリコールジグリシジルエーテル、グリセリ
ントリグリシジルエーテル、アジピン酸ジグリシ
ジルエステル、コハク酸ジグリシジルエステル、
ダイマー酸ジグリシジルエステル、ポリアルキレ
ングリコールジグリシジルエーテル、グリセリン
アルキレンオキシド付加物のトリグリシジルエー
テル等が挙げられる。
前記(A)〜(D)群より選ばれたる少くとも1種と多
価エポキシ化合物との反応生成物は、そのまま圧
延油に用いても極て高い圧延性能を持つている
が、必要に応じ、それに他の動植物油脂、鉱物
油、界面活性剤、極圧添加剤を混合して用いる事
が出来る。
以下実施例によつて本発明を説明する。
実施例 1
水添ヒマシ油941部、オレイン酸564部、パラト
ルエンスルホン酸(以下PTSAと記す)15部を
N2ガス気流下に150〜180℃で7時間反応し、酸
価1.8、水酸基価40.5のヒマシ油誘導体を得た。
このヒマシ油誘導体にエチレングリコールジグ
リシジルエーテル174部、三弗化ホウ素エーテラ
ート2部を加え、80℃にて6時間反応することに
よつて、酸価0.9、水酸基価69.0の反応生成物を
得た。
実施例 2
エチレンオキサイドを15モル付加した水添ヒマ
シ油1601部、イソステアリン酸568部、PTSA20
部を加え160〜200℃で6時間反応し、酸価5.6水
酸基価22.0のヒマシ油誘導体を得た。
上記ヒマシ油誘導体に100〜110℃でPEG―400
―ジグリシジルエーテル250部を加え、6時間反
応して酸価2.0水酸基価15の反応生成物を得た。
実施例 3
エチレンオキサイドを50モル付加したヒマシ油
3135部にアジピン酸ジグリシジルエステル342部
を加え、80〜100℃で6時間反応し酸価1.0、水酸
基価48.0の反応生成物を得た。
実施例 4
ヒマシ油935部、マレイン酸モノオレイルエス
テル368部、PTSA13部を加え、N2ガス気流下
150〜180℃で10時間反応し、酸価1.5、水酸基価
86.2のヒマシ油誘導体を得た。
上記ヒマシ油誘導体にエチレングリコールジグ
リシジルエーテルを87部加え、80〜100℃で6時
間反応し、酸価1.0、水酸基価88.0の反応生成物
を得た。
実施例1〜4の反応生成物を表―1のように単
体もしくは配合品として圧延性能試験に供した。
圧延油No.1〜4の摩擦係数(μ)、耐圧性の測
定を行い、その結果を表―2に示す。
また圧延油No.1〜2については圧延材料に油を
そのまま、またNo.3〜4については15%エマルジ
ヨンを塗布し、試験を行つた。圧延材料への付着
油量はNo.1〜4すべて約1g/m2となるようにし
た。
The present invention relates to rolling oil. Conventionally, palm oil has been used as a rolling oil for steel plates for a long time, but instead, animal and vegetable oils such as beef tallow, lard, Nagasu whale hardened oil, mineral oils, or mixtures of these oils are used as base oils, and additives and oil-based oils are used as rolling oils. Products containing improvers, antioxidants, surfactants, etc. are widely used. On the other hand, the progress of rolling machinery equipment has progressed significantly, and as mills have become larger, there has been a demand for rationalization and precision of the rolling process, such as reducing the number of passes, increasing rolling speed, and increasing the standard accuracy of rolled products. As a result, the conditions for rolling oil are becoming more severe.
Palm oil and tallow-based rolling oils are no longer able to satisfy this condition, but at present no alternative rolling oil has yet been found. The present invention aims to provide a rolling oil that has better lubrication performance than conventional palm oil or beef tallow-based rolling oils and can satisfy the harsh rolling processes currently required. . The rolling oil of the present invention is composed of the following. (A) group is castor oil or hydrogenated castor oil (hereinafter referred to as hydrogenated castor oil); (B) group is castor oil with alkylene oxide added or hydrogenated castor oil with alkylene oxide added (C) group A castor oil derivative obtained by esterifying a part of the hydroxyl group of (A) or (B) with a fatty acid having 12 or more carbon atoms.As group (D), a hydroxyl group having an alkyl or alkenyl group having 11 or more carbon atoms. A castor oil derivative obtained by an esterification reaction between the carboxyl group of a dicarboxylic acid monoester obtained from a compound and a dicarboxylic acid and a part of the hydroxyl group of (A) or (B). ), (C), and (D) and a polyvalent epoxy compound having two or three glycidyl groups in the molecule. The present invention relates to a metal rolling oil characterized in that it is used as it is or, if necessary, mixed with animal and vegetable oils, mineral oils, surfactants, extreme pressure additives, etc. The hydrogenated castor oil in the present invention can be obtained by hydrogenating castor oil in a conventional manner. Castor oil to which alkylene oxide has been added or hydrogenated castor oil to which alkylene oxide has been added can be obtained by adding alkylene oxide to castor oil or hydrogenated castor oil by a conventional method. As the alkylene oxide, one having 2 to 3 carbon atoms is added in an amount of 2 to 100 moles. Furthermore, a castor oil derivative (hereinafter referred to as castor oil derivative (C)) obtained by reacting (A) or (B) with a fatty acid having 12 or more carbon atoms can also be obtained by a generally known esterification reaction. That is, the castor oil derivative (C) used in the present invention can be obtained by a dehydration esterification reaction between a hydroxyl group bonded to (A) or (B) and the above fatty acid, or by a reaction between (A) or (B) and the above fatty acid. It can also be obtained by transesterification with lower esters. However, the essential condition for this castor oil derivative (C) is that at least one hydroxyl group remains in the molecule of the castor oil derivative (C) at the end of the reaction, and 1 mol of (A) or (B) For the above fatty acids
It is obtained by reacting 0.5 to 2 moles. The fatty acids having 12 or more carbon atoms used to obtain the castor oil derivative (C) of the present invention include saturated fatty acids such as lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, and behenic acid, neoacids, and Examples include side chain saturated fatty acids such as the obtained fatty acids, and unsaturated fatty acids such as oleic acid, linoleic acid, linolenic acid, arachidonic acid, and ricinoleic acid. Next, (A) is added to a dicarboxylic acid monoester obtained from a hydroxy compound having an alkyl or alkenyl group having 11 or more carbon atoms and a dicarboxylic acid.
The castor oil derivative obtained by reacting or (B) (hereinafter referred to as castor oil derivative (D)) is a castor oil derivative.
Similarly to (C), it is obtained by reacting 1 mole of (A) or (B) with 0.5 to 2 moles of the above dicarboxylic acid monoester, and the castor oil derivative (D) has at least 1 mole in the molecule. It is an essential condition that hydroxyl groups remain. In addition, the dicarboxylic acid monoester used to obtain the castor oil derivative (D) is a compound obtained by reacting a hydroxy compound having an alkyl or alkenyl group having 11 or more carbon atoms with a dicarboxylic acid at a molar ratio of 1:1. It has one carboxyl group in the molecule. Examples of hydroxy compounds having an alkyl or alkenyl group having 11 or more carbon atoms include lauryl alcohol, palmityl alcohol, cetanol, stearyl alcohol, oleyl alcohol, ethylene glycol oleate, propylene glycol laurate, propylene glycol stearate, and polyethylene glycol palmitate. , polyethylene glycol oleate, glycerin stearate, sorbitol laurate, sorbitol oleate, pentaerythritol stearate, etc., and those obtained by adding alkylene oxide to these hydroxy compounds,
Examples of dicarboxylic acids include dibasic carboxylic acids such as succinic acid, adipic acid, azelaic acid, sebacic acid, maleic acid, fumaric acid, and itaconic acid, and so-called dimer acids obtained by polymerizing unsaturated fatty acids. Next, the reaction product of at least one selected from the four groups (A), (B), (C), and (D) and the polyvalent epoxy compound is the reaction product of the above-mentioned (A), (B), ( It is synthesized according to a conventional method by reacting at least one member selected from the four groups C) and (D) with a polyvalent epoxy compound having two or three glycidyl groups in the molecule. That is, it is due to the addition reaction of a polyvalent epoxy compound to a hydroxyl group bonded to a compound of groups (A) to (D), and for 1 mole of at least one species selected from groups (A) to (D), It is obtained by reacting a polyvalent epoxy compound at a ratio of 0.3 to 2 moles at 70 to 120°C, and the compounds of groups (A) to (D) are crosslinked with the polyvalent epoxy compound, resulting in a chain or network reaction. yields a product. Examples of polyvalent epoxy compounds having two or three glycidyl groups in the molecule used in the present invention include ethylene glycol diglycidyl ether, glycerin triglycidyl ether, adipic acid diglycidyl ester, succinic acid diglycidyl ester,
Examples include dimer acid diglycidyl ester, polyalkylene glycol diglycidyl ether, and triglycidyl ether of glycerin alkylene oxide adduct. The reaction product of at least one selected from the above groups (A) to (D) and a polyvalent epoxy compound has extremely high rolling performance even when used as a rolling oil as it is, but if necessary, it can be used as a rolling oil. , and other animal and vegetable oils and fats, mineral oils, surfactants, and extreme pressure additives can be mixed therewith. The present invention will be explained below with reference to Examples. Example 1 941 parts of hydrogenated castor oil, 564 parts of oleic acid, and 15 parts of para-toluenesulfonic acid (hereinafter referred to as PTSA) were added.
The reaction was carried out at 150 to 180° C. for 7 hours under a N 2 gas stream to obtain a castor oil derivative having an acid value of 1.8 and a hydroxyl value of 40.5. 174 parts of ethylene glycol diglycidyl ether and 2 parts of boron trifluoride etherate were added to this castor oil derivative and reacted at 80°C for 6 hours to obtain a reaction product with an acid value of 0.9 and a hydroxyl value of 69.0. . Example 2 1601 parts of hydrogenated castor oil with 15 moles of ethylene oxide added, 568 parts of isostearic acid, PTSA20
A castor oil derivative having an acid value of 5.6 and a hydroxyl value of 22.0 was obtained. Add PEG-400 to the above castor oil derivative at 100-110℃.
-250 parts of diglycidyl ether was added and reacted for 6 hours to obtain a reaction product with an acid value of 2.0 and a hydroxyl value of 15. Example 3 Castor oil with 50 moles of ethylene oxide added
342 parts of adipic acid diglycidyl ester was added to 3135 parts and reacted at 80 to 100°C for 6 hours to obtain a reaction product having an acid value of 1.0 and a hydroxyl value of 48.0. Example 4 935 parts of castor oil, 368 parts of maleic acid monooleyl ester, and 13 parts of PTSA were added, and the mixture was heated under a stream of N2 gas.
React at 150-180℃ for 10 hours, acid value 1.5, hydroxyl value
A castor oil derivative of 86.2 was obtained. 87 parts of ethylene glycol diglycidyl ether was added to the above castor oil derivative and reacted at 80 to 100°C for 6 hours to obtain a reaction product with an acid value of 1.0 and a hydroxyl value of 88.0. The reaction products of Examples 1 to 4 were subjected to a rolling performance test as shown in Table 1, either alone or as a blend. The friction coefficient (μ) and pressure resistance of rolling oils No. 1 to 4 were measured, and the results are shown in Table 2. Further, for rolling oil Nos. 1 and 2, the oil was applied as it was to the rolling material, and for Nos. 3 and 4, a 15% emulsion was applied to the rolling material for testing. The amount of oil adhering to the rolled material was set to about 1 g/m 2 for all Nos. 1 to 4.
【表】【table】
【表】
圧延性の試験の結果を圧下率(%)と圧延荷重
(ton)との関係をもつて、圧延性能評価とし、図
―1に示した。
比較試料として、市販の牛脂系圧延油を用い
た。
本発明の鋼板用圧延油の潤滑油に関する試験法
は下記の通りである。
摩擦係数試験法
曽田式振子型油性試験機N―型
耐荷重能試験法
シエル型高速四球式摩擦試験機
圧延試験法
圧延機:四段ロール式圧延機
ワークロール直径150mm巾140mm
バツクアツプロール直径250mm巾140mm
ロール材質:クロム鋼
ロール周速:30m/min
圧延材料:SPC―C
厚さ0.60mm×巾50mm×長さ150mm
圧延性能の測定法
圧延前の鋼板に50mmの間隔(l1)で2
本の線を引き、これを圧延して圧延後
の間隔(l2)を測定し、次式により圧
下率を求めた。
圧下率(%)=l2―l1/l2×100
またその時の圧延荷重(ton)をロー
ドセルにて測定した。[Table] The results of the rollability test are shown in Figure 1 as a rolling performance evaluation based on the relationship between rolling reduction (%) and rolling load (ton). A commercially available tallow-based rolling oil was used as a comparative sample. The test method for the lubricating oil for rolling oil for steel plates of the present invention is as follows. Friction coefficient test method Soda type pendulum type oil tester N-type load capacity test method Shell type high speed four ball friction tester rolling test method Rolling mill: Four-roll rolling mill Work roll diameter 150mm Width 140mm Back-up roll diameter 250mm Width 140mm Roll material: Chrome steel Roll circumferential speed: 30m/min Rolling material: SPC-C Thickness 0.60mm x Width 50mm x Length 150mm Method of measuring rolling performance 2 rolls are placed on the steel plate before rolling at 50mm intervals (l 1 ).
A line was drawn, the line was rolled, the distance (l 2 ) after rolling was measured, and the rolling reduction was determined using the following formula. Rolling ratio (%) = l 2 −l 1 /l 2 ×100 In addition, the rolling load (ton) at that time was measured using a load cell.
図面は実施例及び比較例の圧延性能を圧延荷重
(ton)と圧下率(%)の関係により示した圧延性
能比較線図である。
The drawing is a rolling performance comparison diagram showing the rolling performance of Examples and Comparative Examples in terms of the relationship between rolling load (ton) and rolling reduction (%).
Claims (1)
シ油 (B)群としてアルキレンオキサイドを付加したヒ
マシ油、またはアルキレンオキサイドを付加した
水素添加ヒマシ油 (C)群として(A)または(B)のヒドロキシル基の一部
を、炭素数12以上の脂肪酸にてエステル化して得
られるヒマシ油誘導体 (D)群として炭素数11以上のアルキルまたはアル
ケニル基をもつたヒドロキシ化合物とジカルボン
酸とから得られるジカルボン酸モノエステルのカ
ルボキシル基と、(A)または(B)のヒドロキシル基の
一部とのエステル化反応によつて得られるヒマシ
油誘導体 上記(A),(B),(C),(D)の4群より選ばれたる少く
とも1種と分子中にグリシジル基を2または3ケ
有する多価エポキシ化合物との反応によつて得ら
れる反応生成物を主要成分とし、そのまま、また
は必要に応じ、それに動植物油脂、鉱物油、界面
活性剤、極圧添加剤等を混合して用いることを特
徴とする金属圧延油。[Scope of Claims] 1. Castor oil or hydrogenated castor oil as group (A); (B) castor oil with alkylene oxide added, or hydrogenated castor oil with alkylene oxide added; (C) as group (A). ) or a castor oil derivative obtained by esterifying a part of the hydroxyl group of (B) with a fatty acid having 12 or more carbon atoms.Group D is a hydroxy compound having an alkyl or alkenyl group having 11 or more carbon atoms and a dicarboxylic acid. A castor oil derivative obtained by an esterification reaction between the carboxyl group of a dicarboxylic acid monoester obtained from an acid and a part of the hydroxyl group of (A) or (B). The main component is a reaction product obtained by the reaction of at least one member selected from the four groups C) and (D) with a polyvalent epoxy compound having two or three glycidyl groups in the molecule, and as it is. , or a metal rolling oil characterized in that it is mixed with animal and vegetable oils, mineral oils, surfactants, extreme pressure additives, etc., as necessary.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP18464683A JPS5984987A (en) | 1983-10-03 | 1983-10-03 | Rolling mill oil |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP18464683A JPS5984987A (en) | 1983-10-03 | 1983-10-03 | Rolling mill oil |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP8870779A Division JPS5614591A (en) | 1979-07-14 | 1979-07-14 | Metal rolling oil |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5984987A JPS5984987A (en) | 1984-05-16 |
JPS635437B2 true JPS635437B2 (en) | 1988-02-03 |
Family
ID=16156871
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP18464683A Granted JPS5984987A (en) | 1983-10-03 | 1983-10-03 | Rolling mill oil |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5984987A (en) |
-
1983
- 1983-10-03 JP JP18464683A patent/JPS5984987A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS5984987A (en) | 1984-05-16 |
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