JP5879378B2 - 新規なコポリマーおよびその潤滑組成物 - Google Patents
新規なコポリマーおよびその潤滑組成物 Download PDFInfo
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- JP5879378B2 JP5879378B2 JP2014046466A JP2014046466A JP5879378B2 JP 5879378 B2 JP5879378 B2 JP 5879378B2 JP 2014046466 A JP2014046466 A JP 2014046466A JP 2014046466 A JP2014046466 A JP 2014046466A JP 5879378 B2 JP5879378 B2 JP 5879378B2
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- copolymer
- amine
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- oil
- acid
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- 229920001577 copolymer Polymers 0.000 title claims description 181
- 239000000203 mixture Substances 0.000 title claims description 99
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- 150000001412 amines Chemical class 0.000 claims description 71
- 239000004711 α-olefin Substances 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 27
- 150000003138 primary alcohols Chemical class 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 22
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 21
- 239000000178 monomer Substances 0.000 claims description 17
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 10
- 229940000635 beta-alanine Drugs 0.000 claims description 8
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-aminopropionic acid Natural products NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims description 8
- 230000032050 esterification Effects 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- 229920005603 alternating copolymer Polymers 0.000 claims description 3
- -1 aliphatic diester Chemical class 0.000 description 101
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- 238000000034 method Methods 0.000 description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 239000003795 chemical substances by application Substances 0.000 description 25
- 125000000217 alkyl group Chemical group 0.000 description 23
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- 125000003118 aryl group Chemical group 0.000 description 15
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- 239000003999 initiator Substances 0.000 description 13
- 229910052717 sulfur Inorganic materials 0.000 description 12
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- 239000011593 sulfur Substances 0.000 description 11
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- 229940069096 dodecene Drugs 0.000 description 10
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- 150000001735 carboxylic acids Chemical class 0.000 description 8
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- 239000000243 solution Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
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- 125000003277 amino group Chemical group 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 7
- XXUJMEYKYHETBZ-UHFFFAOYSA-N ethyl 4-nitrophenyl ethylphosphonate Chemical compound CCOP(=O)(CC)OC1=CC=C([N+]([O-])=O)C=C1 XXUJMEYKYHETBZ-UHFFFAOYSA-N 0.000 description 7
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- ADOBXTDBFNCOBN-UHFFFAOYSA-N 1-heptadecene Chemical compound CCCCCCCCCCCCCCCC=C ADOBXTDBFNCOBN-UHFFFAOYSA-N 0.000 description 6
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- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 229920002367 Polyisobutene Polymers 0.000 description 6
- 230000003078 antioxidant effect Effects 0.000 description 6
- 239000012986 chain transfer agent Substances 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 125000004185 ester group Chemical group 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 5
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 125000003368 amide group Chemical group 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000003599 detergent Substances 0.000 description 5
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 5
- 125000005462 imide group Chemical group 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000010687 lubricating oil Substances 0.000 description 5
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 5
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- 239000011701 zinc Substances 0.000 description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 4
- PJLHTVIBELQURV-UHFFFAOYSA-N 1-pentadecene Chemical compound CCCCCCCCCCCCCC=C PJLHTVIBELQURV-UHFFFAOYSA-N 0.000 description 4
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 4
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
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- GVPWHKZIJBODOX-UHFFFAOYSA-N dibenzyl disulfide Chemical compound C=1C=CC=CC=1CSSCC1=CC=CC=C1 GVPWHKZIJBODOX-UHFFFAOYSA-N 0.000 description 4
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- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
- C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M145/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
- C10M145/16—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate polycarboxylic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives thereof
- C08F220/66—Anhydrides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/04—Anhydrides, e.g. cyclic anhydrides
- C08F222/06—Maleic anhydride
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/14—Esterification
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
- C10M107/22—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M107/28—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/40—Lubricating compositions characterised by the base-material being a macromolecular compound containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M109/00—Lubricating compositions characterised by the base-material being a compound of unknown or incompletely defined constitution
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
- C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M145/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
- C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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Description
(2)αオレフィン−無水マレイン酸コポリマーを、C12〜C16アルコールを47重量%、C9〜C10アルコールを20重量%およびC16〜C18アルコールを33重量%含むC9〜C18アルコールの混合物と反応させて調製される。このコポリマーは、ナフテン基またはパラフィン基原油画分を含む潤滑油の目視可能なワックス粒子を室温で分散する方法に使用される。
(項目1)
(i)α−オレフィンと(ii)エチレン性不飽和カルボン酸またはβ位以上で分枝している第一級アルコールでエステル化されたその誘導体とのモノマーから得られる単位を含むコポリマーであって、エステル化前の還元比粘度が最大0.08である、コポリマー。
(項目2)
前記エチレン性不飽和カルボン酸またはその誘導体は無水マレイン酸である、項目1に記載のコポリマー。
(項目3)
前記コポリマーは還元比粘度が0.02〜0.07、0.03〜0.07または0.04〜0.06である、先行する項目1〜2のいずれかに記載のコポリマー。
(項目4)
前記α−オレフィンは6個以上、10〜18個または12個の炭素原子を有する、先行する項目1〜3のいずれかに記載のコポリマー。
(項目5)
前記コポリマーは(i)6個以上、10〜18個または12個の炭素原子を有するα−オレフィンと(ii)無水マレイン酸とのモノマーから得られる単位からなる、先行する項目1〜4のいずれかに記載のコポリマー。
(項目6)
前記コポリマーは(i)12個の炭素原子を有するα−オレフィンと(ii)無水マレイン酸とのモノマーから得られる単位からなる、先行する項目1〜5のいずれかに記載のコポリマー。
(項目7)
窒素含有化合物でさらにアミド化またはイミド化される、先行する項目1〜6のいずれかに記載のコポリマー。
(項目8)
先行する項目1〜7のいずれかに記載のコポリマーであって、(i)α−オレフィンと(ii)エチレン性不飽和カルボン酸またはその誘導体とのモノマーから得られる単位を含み、
該カルボン酸単位の75%〜99.9%はβ位以上で分枝している第一級アルコールでエステル化され、
該カルボン酸単位の0.1〜25%は窒素含有化合物でアミド化またはイミド化されている、
コポリマー。
(項目9)
前記窒素含有化合物はモルホリン、イミダゾリジノン、アセトアミド、β−アラニンアルキルエステルおよびこれらの混合物からなる群から選択されるアミン含有化合物である、先行する項目7〜8のいずれかに記載のコポリマー。
(項目10)
前記コポリマーは交互コポリマーである、先行する項目1〜9のいずれかに記載のコポリマー。
(項目11)
前記β位以上で分枝している第一級アルコールは少なくとも12〜60個の炭素原子を有してもよい、先行する項目1〜10のいずれかに記載のコポリマー。
(項目12)
前記β位以上で分枝している第一級アルコールはゲルベアルコールである、先行する項目1〜10のいずれかに記載のコポリマー。
(項目13)
コポリマーを調製するプロセスであって:
(1)(i)α−オレフィンと(ii)エチレン性不飽和カルボン酸またはその誘導体とを反応させてコポリマーを形成するステップ;
(2)ステップ(1)のコポリマーをβ位以上で分枝している第一級アルコールでエステル化してエステル化コポリマーを形成するステップ;および
(3)任意にステップ(2)のエステル化コポリマーを一定量のアミンと反応させて0.01wt%〜1.5wt%の窒素を含むエステル化コポリマーを形成するステップ
を含み、
ステップ(1)のコポリマーは還元比粘度が最大0.08である、
プロセス。
(項目14)
ステップ(3)をさらに含む、項目13に記載のプロセス。
(項目15)
コポリマーを調製するプロセスであって:
(1)(i)α−オレフィンと(ii)β位以上で分枝している第一級アルコールから得られたエステル基を有するエステル化カルボン酸またはその誘導体とを反応させて生成物を形成するステップ;
(2)任意にステップ(1)の生成物を一定量のアミンと反応させて0.01wt%〜1.5wt%の窒素を含むエステル化コポリマーを得るステップ
を含み、
該コポリマーは還元比粘度が最大0.08である、
プロセス。
(項目16)
ステップ(2)をさらに含む、項目15に記載のプロセス。
(項目17)
先行する項目13〜16のいずれかに記載のプロセスにより得られた/得られる、コポリマー。
(項目18)
潤滑粘度の油と、先行する項目13〜17のいずれかに記載のプロセスにより得られた/得られるコポリマーとを含む、潤滑組成物。
(項目19)
潤滑粘度の油と、先行する項目1〜18のいずれかに記載のコポリマーとを含む、潤滑組成物。
(項目20)
先行する項目1〜19のいずれかに記載のコポリマーの、潤滑油基油としての使用。
(項目21)
前記潤滑油基油は先行する項目1〜19のいずれかに記載のコポリマーであり、他の基油の非存在下にある、項目20の使用。
(項目22)
先行する項目1〜19のいずれかに記載のコポリマーは、ポリアルファオレフィン、ブライトストックおよびポリエステル冷却潤滑剤からなる群から選択される少なくとも1種の基油の代わりになる、項目20の使用。
(項目23)
酸化制御のための潤滑剤での、先行する項目7〜9のいずれかに記載のコポリマーの使用。
一実施形態では、本発明は、(i)α−オレフィンと(ii)エチレン性不飽和カルボン酸またはβ位以上で分枝した第一級アルコールでエステル化したその誘導体とのモノマーから得られた単位を含むコポリマーであって、エステル化前の還元比粘度(RSV:reduced specific viscosity)が最大0.08または0.02〜0.08(または0.02〜0.07、0.03〜0.07または0.04〜0.06)であるコポリマーを提供する。典型的には本明細書に記載のRSVの範囲は、コポリマーについて行った3回の測定値の平均による。
エステル化されるカルボン酸単位の0.1〜99.89(または1〜50または2.5〜20または5〜15)%は、β位以上で分枝した第一級アルコールアルコールで官能基化され、
エステル化されるカルボン酸単位の0.1〜99.89(または1〜50または2.5〜20または5〜15)%は、直鎖アルコールまたはα−分枝アルコールで官能基化され、
カルボン酸単位の0.01〜10%(または0.1%〜20%または0.02%〜7.5%または0.1〜5%または0.1〜2%未満)は、アミノ基、アミド基および/またはイミド基の少なくとも1つを有し、
還元比粘度が最大0.08である。
カルボン酸単位の0.1〜99.89%は、β位以上で分枝した第一級アルコールでエステル化され、
カルボン酸単位の0.1〜99.89%は、直鎖アルコールまたはα−分枝アルコール(たとえば第二級アルコール)でエステル化され、
カルボン酸単位の0.01〜10%は、アミノ基、アミド基および/またはイミド基の少なくとも1つを有し、
還元比粘度が最大0.08である。
カルボン酸単位の0.1〜99.89%は、β位以上で分枝した第一級アルコールでエステル化され、
カルボン酸単位の0.1〜99.9%は、直鎖アルコールまたはα−分枝アルコールでエステル化され、
カルボン酸単位の0〜10%は、アミノ基、アミド基および/またはイミド基の少なくとも1つを有し、
還元比粘度が最大0.08である。
カルボン酸単位の5〜15%は、β位以上で分枝した第一級アルコールでエステル化され、
カルボン酸単位の0.1〜95%は、直鎖アルコールまたはα−分枝アルコールでエステル化され、
カルボン酸単位の0〜2%未満は、アミノ基、アミド基および/またはイミド基の少なくとも1つを有し、
還元比粘度が最大0.08である。
(1)(i)α−オレフィンと、(ii)エチレン性不飽和カルボン酸またはその誘導体(典型的にはフマル酸、無水マレイン酸、マレイン酸、(メタ)アクリル酸、イタコン酸無水物またはイタコン酸)またはその誘導体とを反応させてコポリマーを形成するステップ;
(2)ステップ(1)のコポリマーを、β位以上で分枝した第一級アルコールでエステル化してエステル化コポリマーを形成するステップ;および
(3)任意にステップ(2)のエステル化コポリマーを一定量のアミンと反応させて0.01wt%〜1.5wt%(または0.05wt%〜0.75wt%または0.075wt%〜0.25wt%)の窒素を含むエステル化コポリマーを得るステップ、
を含み、ステップ(1)のコポリマーは還元比粘度が最大0.08または0.02〜0.08(または0.02〜0.07、0.03〜0.07または0.04〜0.06)であるプロセスを提供する。
(1)(i)α−オレフィンと、(ii)β位以上で分枝した第一級アルコールから得られるエステル基を有するエステル化カルボン酸またはその誘導体とを反応させて生成物を形成するステップ;
(2)任意にステップ(1)の生成物を一定量のアミンと反応させて、0.01wt%〜1.5wt%(または0.05wt%〜1wt%または0.075wt%〜0.5wt%)の窒素を含むエステル化コポリマーを得るステップ、
を含み、コポリマーは還元比粘度が最大0.08または0.02〜0.08(または0.02〜0.07、0.03〜0.07または0.04〜0.06)であるプロセスを提供する。
Xは、(i)炭素および少なくとも1個の酸素または窒素原子を含む官能基か、あるいは(ii)1〜5個の炭素原子(典型的には−CH2−)を有するアルキレン基である官能基のどちらかであり、コポリマー骨格と()y内に含まれる分枝ヒドロカルビル基とを連結し;
wは、2〜2000または2〜500または5〜250の範囲であり得る、コポリマー骨格に結合したペンダント基の数であり;
yは、0、1、2または3であるが、ただし、ペンダント基の少なくとも1mol%では、yは0ではなく;さらにyが0である場合、XはXの原子価を十分に満たすように末端基に結合しており、末端基は水素、アルキル、アリール、金属(典型的にはエステル反応物の中和の際に導入される。好適な金属としては、カルシウム、マグネシウム、バリウム、亜鉛、ナトリウム、カリウムまたはリチウムがある)またはアンモニウムカチオンおよびこれらの混合物から選択され;
pは、1〜15(または1〜8または1〜4)の範囲の整数であり;
R’およびR’’は、独立に直鎖または分枝ヒドロカルビル基であり、R’およびR’’に存在する炭素原子を合わせた総数は少なくとも12(または少なくとも16または少なくとも18または少なくとも20)である
コポリマーを提供する。
1)C15〜16ポリメチレン基を含むアルキル基、たとえば2−C1〜15アルキル−ヘキサデシル基(たとえば2−オクチルヘキサデシル)および2−アルキル−オクタデシル基(たとえば2−エチルオクタデシル、2−テトラデシル−オクタデシルおよび2−ヘキサデシルオクタデシル);
2)C13〜14ポリメチレン基を含むアルキル基、たとえば1−C1〜15アルキル−テトラデシル基(たとえば2−ヘキシルテトラデシル、2−デシルテトラデシルおよび2−ウンデシルトリデシル)および2−C1〜15アルキル−ヘキサデシル基(たとえば2−エチル−ヘキサデシルおよび2−ドデシルヘキサデシル);
3)C10〜12ポリメチレン基を含むアルキル基、たとえば2−C1〜15アルキル−ドデシル基(たとえば2−オクチルドデシル)および2−C1〜15アルキル−ドデシル基(2−ヘキシルドデシルおよび2−オクチルドデシル)、2−C1〜15アルキル−テトラデシル基(たとえば2−ヘキシルテトラデシルおよび2−デシルテトラデシル);
4)C6〜9ポリメチレン基を含むアルキル基、たとえば2−C1〜15アルキル−デシル基(たとえば2−オクチルデシル)および2,4−ジ−C1〜15アルキル−デシル基(たとえば2−エチル−4−ブチル−デシル基);
5)C1〜5ポリメチレン基を含むアルキル基、たとえば2−(3−メチルヘキシル)−7−メチル−デシルおよび2−(1,4,4−トリメチルブチル)−5,7,7−トリメチル−オクチル基;および
6)および2種以上の分枝アルキル基の混合物、たとえばプロピレンオリゴマー(六量体から十一量体)、エチレン/プロピレン(モル比16:1〜1:11)オリゴマー、イソ−ブテンオリゴマー(五量体から八量体)、C5〜17α−オレフィンオリゴマー(二量体〜六量体)に対応するオキソアルコールのアルキル残基。
Xは−OHまたは−NH2であり;
Hy’’は水素またはヒドロカルビル基(典型的にはアルキルまたはC1〜4−もしくはC2−アルキル)であり;
Hyはヒドロカルビレン基(典型的にはアルキレンまたはC1〜4−もしくはC2−アルキレン)であり;
Qは>NH、>NR、>CH2、>CHR、>CR2、または−O−(典型的には>NHまたは>NR)であり、
RはC1〜4アルキルである。
潤滑組成物は、潤滑粘度の油を含む。こうした油は、天然油および合成油、水素化分解、水素化および水素化仕上げから得られる油、未精製油、精製油および再精製油ならびにこれらの混合物を含む。
Oil Interchangeability Guidelines)に規定されているものと定義することもできる。5つの基油の分類は以下の通りである:グループI(硫黄含有量>0.03wt%および/または<90wt%飽和分、粘度指数80〜120);グループII(硫黄含有量≦0.03wt%および≧90wt%飽和分、粘度指数80〜120);グループIII(硫黄含有量≦0.03wt%および≧90wt%飽和分、粘度指数≧120);グループIV(すべてのポリアルファオレフィン(PAO:polyalphaolefin));およびグループV(グループI、II、IIIまたはIV以外のもの)。潤滑粘度の油は、APIグループI、グループII、グループIII、グループIV、グループVの油またはこれらの混合物を含む。多くの場合、潤滑粘度の油は、APIグループI、グループII、グループIII、グループIVの油またはこれらの混合物である。あるいは、潤滑粘度の油は、多くの場合、APIグループI、グループII、グループIIIの油またはこれらの混合物である。
本明細書に記載のコポリマーおよび/または潤滑組成物から得られる組成物は任意に他の性能添加剤をさらに含む。他の性能添加剤は、金属活性低下剤、従来の清浄剤(当該技術分野において公知の従来のプロセスにより調製される清浄剤)、分散剤、粘度調整剤、摩擦調整剤、腐食抑制剤、分散剤配合粘度調整剤、摩耗防止剤、極圧剤、スカッフィング防止剤、酸化防止剤、抑泡剤、抗乳化剤、流動点降下剤、シール膨潤剤およびこれらの混合物の少なくとも1種を含む。典型的には、完全に配合された潤滑油は、こうした性能添加剤の1種または複数種を含むものである。
分散剤は、潤滑油組成物に混合する前に灰を形成する金属を含んでおらず、潤滑剤および高分子分散剤に加えても、灰を形成する金属を全くない生じないのが一般的であるため、多くの場合、無灰型分散剤として知られる。無灰型分散剤は、比較的高分子量の炭化水素鎖に結合した極性基を特徴とする。典型的な無灰分散剤は、N置換長鎖アルケニルスクシンイミドを含む。N置換長鎖アルケニルスクシンイミドの例として、元になるポリイソブチレンの数平均分子量が350〜5000または500〜3000のポリイソブチレンスクシンイミドがある。
潤滑剤組成物は任意に、公知の中性または過塩基性清浄剤、すなわち、当該技術分野において公知の従来のプロセスで調製された清浄剤をさらに含む。好適な清浄剤の基材として、フェネート、硫黄含有フェネート、スルホナート、サリキサラート、サリチラート、カルボン酸、リン含有酸、アルキルフェノール、硫黄結合アルキルフェノール化合物またはサリゲニンが挙げられる。
酸化防止剤化合物は公知であり、硫化オレフィン、ジフェニルアミン、ヒンダードフェノール、ジチオカルバミン酸モリブデンおよびこれらの混合物を含む。酸化防止剤化合物は単独で使用しても、あるいは組み合わせて使用してもよい。
本発明のペンダント基を有するポリマー以外の粘度調整剤には、水素添加スチレンブタジエンゴム、エチレン−プロピレンコポリマー、水素添加スチレン−イソプレンポリマー、水素化ジエンポリマー、ポリアルキルスチレン、ポリオレフィン、ポリアルキル(メタ)アクリラートおよび無水マレイン酸−スチレンコポリマーのエステルまたはこれらの混合物がある。一実施形態では、高分子粘度調整剤はポリ(メタ)アクリラートである。
潤滑組成物は任意に、少なくとも1種の摩耗防止剤をさらに含む。好適な摩耗防止剤の例として、リン化合物の油溶性アミン塩、硫化オレフィン、金属ジヒドロカルビルジチオホスフェート(亜鉛ジアルキルジチオホスフェートなど)、チオカルバマートエステル、チオカルバマートアミド、チオカルバミン酸エーテル、アルキレン結合チオカルバマートおよびビス(S−アルキルジチオカルバミル)ジスルフィドなどのチオカルバマート含有化合物がある。
潤滑剤組成物はさらに、スカッフィング防止剤を含んでいてもよい。スカッフィング防止剤化合物は、凝着摩耗を抑制すると考えられ、多くの場合、硫黄含有化合物である。典型的には、硫黄含有化合物は、ジベンジルジスルフィド、ビス−(クロロベンジル)ジスルフィド、ジブチルテトラスルフィド、ジ−第三級ブチルポリスルフィド、オレイン酸の硫化メチルエステル、硫化アルキルフェノール、硫化ジペンテン、硫化テルペン、硫化ディールズ・アルダー付加物、アルキルスルフェニルN’N−ジアルキルジチオカルバマート、ポリアミンと多塩基酸エステルとの反応生成物、2,3−ジブロモプロポキシイソ酪酸のクロロブチルエステル、ジアルキルジチオカルバミン酸のアセトキシメチルエステルおよびキサントゲン酸のアシルオキシアルキルエーテルなどの硫化オレフィン、有機スルフィドおよびポリスルフィド、ならびにこれらの混合物を含む。
油に可溶である極圧(EP:Extreme Pressure)剤は、硫黄およびクロロ硫黄含有EP剤、塩素化炭化水素EP剤およびリンEP剤を含む。こうしたEP剤の例として、塩素化ワックス;ジベンジルジスルフィド、ビス−(クロロベンジル)ジスルフィド、ジブチルテトラスルフィド、オレイン酸の硫化メチルエステル、硫化アルキルフェノール、硫化ジペンテン、硫化テルペンおよび硫化ディールズ・アルダー付加物などの硫化オレフィン(硫化イソブチレンなど)、有機スルフィドおよびポリスルフィド;リンスルフィドとテレビンまたはオレイン酸メチルとの反応生成物などのリン硫化炭化水素;二炭化水素および三炭化水素亜リン酸エステルなどのリンエステル、たとえば、亜リン酸ジブチル、亜リン酸ジヘプチル、亜リン酸ジシクロヘキシル、亜リン酸ペンチルフェニル;亜リン酸ジペンチルフェニル、亜リン酸トリデシル、亜リン酸ジステアリルおよびポリプロピレン置換フェノールホスフィット;ジオクチルジチオカルバミン酸亜鉛およびバリウムヘプチルフェノール二酸などの金属チオカルバマート;アルキルおよびジアルキルリン酸または誘導体のアミン塩、たとえば、ジアルキルジチオリン酸をプロピレンオキシドと反応させ、その後さらにP2O5と反応させた生成物のアミン塩;およびこれらの混合物(米国特許第3,197,405号に記載されている)が挙げられる。
本発明の方法および潤滑組成物は、冷却潤滑剤、グリース、ギヤ油、車軸油、駆動軸油、トラクション油、手動変速機油、自動変速機油、金属加工油剤、作動油または内燃機関油に好適であり得る。
variable transmission)、トロイダル変速機、連続スリップトルクコンバータクラッチ(CSTCC:continuously slipping torque converter clutch)、有段式自動変速機またはデュアルクラッチ式変速機(DCT:dual clutch transmission)を含む。
調製例1:1−ドデセンおよび無水マレイン酸コポリマー
コポリマー骨格の調製(Cpp:Copolymer Backbone Preparation):コポリマーは、3リットルフラスコにて60wt%のトルエン溶媒の存在下で1モルの無水マレイン酸およびYモル(以下に定義する)の1−ドデセンを反応させて調製する。フラスコに、フランジ蓋およびクリップ、PTFEスターラーグランド、ロッドおよびオーバーヘッドスターラー、熱電対、窒素入口ポート、および水冷式冷却器を装着する。窒素を0.028m3/時(または1SCFH)でフラスコに吹き込む。別の500ml枝付きフラスコに0.05モルのtert−ブチルペルオキシ−2−エチルヘキサノアート開始剤(Trigonox(登録商標)21Sと呼ばれるAkzo Nobelから市販されている開始剤)、任意にn−ドデシルメルカプタン(連鎖移動剤、CTA:chain transfer agent)および追加のトルエンを仕込む。窒素管を枝に取り付け、窒素を0.085m3/時(または0.3SCFH)で30分間導入する。3リットルフラスコを105℃に加熱する。Trigonox 21S開始剤/トルエン混合物を500mlフラスコから3リットルフラスコにMasterflex(商標)ポンプ(流量を0.8ml/minに設定)で5時間かけて送る。3リットルフラスコの内容物を1時間撹拌してから95℃まで冷却する。3リットルフラスコの内容物を一晩撹拌する。典型的には無色透明のゲルが得られる。各試薬の量を下記表に示す。
直鎖アルコールはAlfol(登録商標)810として市販されているC8〜10混合物である。
B1は2−ヘキシルデカノールである。
B2は2−エチルヘキサノールである。
B3は2−オクチルドデカノールである。
Esc21*は本発明と同じポリマー骨格を有するが、直鎖エステル基しか有さない比較エステル化コポリマーである。
アミン1は1−(2−アミノ−エチル)−イミダゾリジン−2−オンである。
アミン2は4−(3−アミノプロピル)モルホリンである。
アミン3は3−(ジメチルアミノ)−1−プロピルアミンである。
アミン4はN−フェニル−p−フェニレンジアミンである。
アミン5はN−(3−アミノプロピル)−2−ピロリジノンである。
アミン6はアミノエチルアセトアミドである。
アミン7はβ−アラニンメチルエステルである。
アミン8は1−(3−アミノプロピル)イミダゾールである。
一連のSAE 75W−110車軸流体(AF1〜AF8)を本発明のコポリマーで処理して100℃の動粘度をほぼ等しくする。車軸流体にさらに0.2wt%のポリメタクリラート流動点降下剤を含ませる。車軸流体の動粘度(KV100、100℃でのASTM方法D445による)ブルックフィールド粘度(BV、−40℃でのASTM D2983による)および粘度指数(VI、ASTM D2270)に関して評価する。得られる結果は以下である。
一連のSAE 75W−85手動変速機流体(MF1〜MF3)を本発明のコポリマーで処理して100℃の動粘度をほぼ等しくする。手動変速機流体にさらに0.2wt%のポリメタクリラート流動点降下剤を含ませる。手動変速機流体を試験3の車軸流体と同様のやり方で評価する。得られる結果は以下である。
a.炭化水素置換基、すなわち、脂肪族置換基(たとえば、アルキルまたはアルケニル)、脂環式置換基(たとえば、シクロアルキル、シクロアルケニル)、ならびに芳香族置換、脂肪族置換、および脂環式置換芳香族置換基、さらには環が分子の別の部分を介して完成される(たとえば、2つの置換基が一緒に環を形成する)環状置換基;
b.置換された炭化水素置換基、すなわち、本発明の文脈で置換基の炭化水素の主な性質を変化させない非炭化水素基を含む置換基(たとえば、ハロ(特にクロロおよびフルオロ)、ヒドロキシ、アルコキシ、メルカプト、アルキルメルカプト、ニトロ、ニトロソおよびスルホキシ);
c.ヘテロ置換基、すなわち、本発明の文脈で、主に炭化水素の特性を有する一方で、炭素原子で構成される環または鎖に炭素以外を含む、置換基;および
d.ヘテロ原子であって、硫黄、酸素、窒素を含み、ピリジル、フリル、チエニルおよびイミダゾリルとして置換基を包含する。一般に、ヒドロカルビル基の炭素原子10個ごとに2個以下、一態様では1個以下の非炭化水素置換基が存在し;典型的には、ヒドロカルビル基に非炭化水素置換基は存在しない。
Claims (9)
- 潤滑組成物であって、該潤滑組成物が、
潤滑粘度の油、および
(i)α−オレフィンと(ii)エチレン性不飽和カルボン酸またはβ位以上で分枝している第一級アルコールでエステル化されたその誘導体とのモノマーから得られる単位を含むコポリマーであって、エステル化前の還元比粘度が最大0.08である、コポリマー、
を含み、
該β位以上で分枝している第一級アルコールが、少なくとも12〜60個の炭素原子を有してもよく、そして
該コポリマーが、アセトアミド、β−アラニンアルキルエステルおよびこれらの混合物からなる群から選択されるアミン含有化合物でさらにアミド化またはイミド化されている、潤滑組成物。 - 前記エチレン性不飽和カルボン酸またはその誘導体は無水マレイン酸である、請求項1に記載の潤滑組成物。
- 前記コポリマーは還元比粘度が0.02〜0.07、0.03〜0.07または0.04〜0.06である、先行する請求項1〜2のいずれかに記載の潤滑組成物。
- 前記α−オレフィンは6個以上、10〜18個または12個の炭素原子を有する、先行する請求項1〜3のいずれかに記載の潤滑組成物。
- 前記コポリマーは(i)6個以上、10〜18個または12個の炭素原子を有するα−オレフィンと(ii)無水マレイン酸とのモノマーから得られる単位からなる、先行する請求項1〜4のいずれかに記載の潤滑組成物。
- 前記コポリマーは(i)12個の炭素原子を有するα−オレフィンと(ii)無水マレイン酸とのモノマーから得られる単位からなる、先行する請求項1〜5のいずれかに記載の潤滑組成物。
- 先行する請求項1〜6のいずれかに記載の潤滑組成物であって、
(i)α−オレフィンと(ii)エチレン性不飽和カルボン酸またはその誘導体とのモノマーから得られる単位を含み、
該カルボン酸単位の75%〜99.9%はβ位以上で分枝している第一級アルコールでエステル化され、
該カルボン酸単位の0.1〜25%は、アセトアミド、β−アラニンアルキルエステルおよびこれらの混合物からなる群から選択されるアミン含有化合物でアミド化またはイミド化されている、
潤滑組成物。 - 前記コポリマーは交互コポリマーである、先行する請求項1〜7のいずれかに記載の潤滑組成物。
- 前記β位以上で分枝している第一級アルコールはゲルベアルコールである、先行する請求項1〜8のいずれかに記載の潤滑組成物。
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EP2351780A1 (en) | 2011-08-03 |
CA2732278C (en) | 2017-12-19 |
EP2664632A1 (en) | 2013-11-20 |
CN102171258A (zh) | 2011-08-31 |
KR101659099B1 (ko) | 2016-09-22 |
JP2015157963A (ja) | 2015-09-03 |
KR20110033307A (ko) | 2011-03-30 |
JP2014101525A (ja) | 2014-06-05 |
EP2351780B1 (en) | 2018-10-10 |
EP2310425A1 (en) | 2011-04-20 |
WO2010014655A1 (en) | 2010-02-04 |
EP2664631A1 (en) | 2013-11-20 |
CN102171258B (zh) | 2014-10-15 |
JP5539983B2 (ja) | 2014-07-02 |
CN104277144A (zh) | 2015-01-14 |
EP2310425B1 (en) | 2016-11-23 |
JP2011529980A (ja) | 2011-12-15 |
BRPI0916605A2 (pt) | 2017-07-04 |
EP2664631B1 (en) | 2016-12-07 |
US20130310290A1 (en) | 2013-11-21 |
CA2732278A1 (en) | 2010-02-04 |
US20110190182A1 (en) | 2011-08-04 |
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