JP7004769B2 - 組成物およびその形成方法 - Google Patents
組成物およびその形成方法 Download PDFInfo
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- JP7004769B2 JP7004769B2 JP2020095049A JP2020095049A JP7004769B2 JP 7004769 B2 JP7004769 B2 JP 7004769B2 JP 2020095049 A JP2020095049 A JP 2020095049A JP 2020095049 A JP2020095049 A JP 2020095049A JP 7004769 B2 JP7004769 B2 JP 7004769B2
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- composition
- amine
- derivative
- less
- dithiophosphate
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 46
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- 239000007795 chemical reaction product Substances 0.000 claims description 37
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- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 10
- PZFYOFFTIYJCEW-UHFFFAOYSA-N n-tridecyltridecan-1-amine Chemical compound CCCCCCCCCCCCCNCCCCCCCCCCCCC PZFYOFFTIYJCEW-UHFFFAOYSA-N 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 238000000354 decomposition reaction Methods 0.000 claims description 7
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- 229960002317 succinimide Drugs 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- JZALLXAUNPOCEU-UHFFFAOYSA-N tetradecylbenzene Chemical compound CCCCCCCCCCCCCCC1=CC=CC=C1 JZALLXAUNPOCEU-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- HVGINUIPKBCAQD-UHFFFAOYSA-N trihydroxy-[[3-(2-methylpropyl)-2-phenylphenyl]-phenyl-lambda4-sulfanylidene]-lambda5-phosphane Chemical compound CC(C)CC1=C(C(=CC=C1)S(=P(O)(O)O)C2=CC=CC=C2)C3=CC=CC=C3 HVGINUIPKBCAQD-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical class C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- SMVBWTKCDCPTQG-UHFFFAOYSA-N tris[2-(7-methyloctyl)phenoxy]-sulfanylidene-$l^{5}-phosphane Chemical compound CC(C)CCCCCCC1=CC=CC=C1OP(=S)(OC=1C(=CC=CC=1)CCCCCCC(C)C)OC1=CC=CC=C1CCCCCCC(C)C SMVBWTKCDCPTQG-UHFFFAOYSA-N 0.000 description 1
- 238000012065 two one-sided test Methods 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
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
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/123—Reaction products obtained by phosphorus or phosphorus-containing compounds, e.g. P x S x with organic compounds
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
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- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/10—Thio derivatives
- C10M137/105—Thio derivatives not containing metal
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/043—Ammonium or amine salts thereof
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- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/047—Thioderivatives not containing metallic elements
-
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/04—Molecular weight; Molecular weight distribution
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- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
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- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
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Description
材料の中には、加熱時に硫化水素(H2S)を形成するものがある。こうした材料の熱分解は、一般には望ましくない。こうした材料の熱分解が、該材料の配送、取扱いおよび/または貯蔵中に生じる可能性がある。材料を収容する容器(例えばドラム)が、ローディングドックに、またはトラック、鉄道車両、倉庫内等に格納される際に熱分解が生じることがある。高温でかつ日当たりの良い気候が特に問題となる。やがて容器が開放されると、作業者は漏出するH2Sに曝されることがある。このH2Sは刺激性ないし毒性である場合がある。
ここで、組成物を開示する。該組成物は、ジチオホスファート誘導体とアミンとの反応生成物を含む。該反応生成物は、少なくとも約25質量%の量で該組成物中に存在する。また、該組成物の製造方法を開示する。該方法は、ジチオホスファート誘導体とアミンとを組み合わせることにより該組成物を製造するステップを含む。さらに、ジチオホスファート誘導体の熱安定性を向上させる方法を開示する。該方法は、ジチオホスファート誘導体とアミンとを組み合わせるステップを含む。ジチオホスファート誘導体は、分解して硫化水素(H2S)を形成しうる。しかし、アミンが実質的に該ジチオホスファート誘導体の熱分解を防止する。
ここで、組成物を開示する。また、該組成物の形成方法を開示する。該組成物は、ジチオホスファート誘導体とアミンとの反応生成物を含む。特定の実施形態において、該組成物は、実質的にジチオホスファート誘導体とアミンとの反応生成物からなる。さらなる実施形態において、該組成物は、ジチオホスファート誘導体とアミンとの反応生成物からなる。
組成物は様々な最終用途に有用であって、いずれかの特定の使用に限定されない。例えば、組成物を耐摩耗添加剤として使用することができ、例えば潤滑剤、金属加工用流体、または作動液において使用するための耐摩耗添加剤として使用することができる。特定の実施形態において、組成物を、無灰型耐摩耗性組成物または無灰型耐摩耗性化合物と呼ぶことができる。
組成物の例を配合する。組成物1Aおよび1Bは、比較組成物である。組成物2A、2B、3Aおよび3Bは、本発明の組成物である。各成分を組み合わせかつ混合することによりこれらの組成物を形成し、かつ下記の様々な試験方法を用いて評価する。ここに、本明細書の一部を構成するものとして各試験方法の内容を援用する。さらなる詳細については、以下の第I表~第IV表に記載しかつ説明する。
・オーブン温度:
a.初期温度:35℃で5分間
b.ランプ・レート1:10℃/分で100℃まで
c.ランプ・レート2:20℃/分で275℃まで、および25分間保持・
・カラム仕様:
a.JW Scientific DB-1 105m×0.53mm×5.00ミクロン
b.操作温度:-60℃~260℃/280℃
c.Antek 7090S 検出器
d.シリアルナンバーUS47890214
その後、ppmでのH2S発生を、内部標準に基づき算出する。本発明の組成物の各々は10ppmよりもはるかに低いH2Sを示す。さらに本発明の組成物は、比較組成物に対して熱安定性の向上を示す。
本願の好ましい実施態様を以下に示す:
[実施態様1]
ジチオホスファート誘導体とアミンとの反応生成物を含む組成物であって、該反応生成物が少なくとも約25質量%の量で存在する、前記組成物。
[実施態様2]
反応生成物が少なくとも約50質量%の量で存在する、実施態様1に記載の組成物。
[実施態様3]
反応生成物が少なくとも約75質量%の量で存在する、実施態様1に記載の組成物。
[実施態様4]
前記ジチオホスファート誘導体が、次の一般式:
R1およびR2は、互いに独立して、C3~C18アルキル、C5~C12シクロアルキル、C5~C6シクロアルキルメチル、C9~C10ビシクロアルキルメチル、C9~C10トリシクロアルキルメチル、フェニル、またはC7~C24アルキルフェニルであるか、または、
R1とR2とが一緒になって(CH3)2C(CH2)2であり;
R3は、水素またはメチルであり;かつ
n+mの合計は、少なくとも1である]
で示される、実施態様1から3までのいずれかに記載の組成物。
[実施態様5]
R1およびR2が、互いに独立して、C3~C18アルキル、C5~C6シクロアルキル、またはC7~C18アルキルフェニルである、実施態様4に記載の組成物。
[実施態様6]
R3が水素であり、かつn+mの合計が1~25である、実施態様4または5に記載の組成物。
[実施態様7]
前記ジチオホスファート誘導体がβ-ジチオリン酸化プロピオン酸である、実施態様1から6までのいずれかに記載の組成物。
[実施態様8]
前記アミンが約3000未満の数平均分子量(Mn)を有する、実施態様1から7までのいずれかに記載の組成物。
[実施態様9]
前記アミンが約2000未満の数平均分子量(Mn)を有する、実施態様1から8までのいずれかに記載の組成物。
[実施態様10]
前記アミンが脂肪族アミンまたは脂環式アミンである、実施態様1から9までのいずれかに記載の組成物。
[実施態様11]
前記アミンが第2級脂肪族アミンである、実施態様10に記載の組成物。
[実施態様12]
前記アミンがジトリデシルアミンである、実施態様11に記載の組成物。
[実施態様13]
さらに遊離ジチオホスファート誘導体を含む、実施態様1から12までのいずれかに記載の組成物。
[実施態様14]
硫化水素(H2S)曝露に関する労働安全衛生局(OSHA)基準を満たす、実施態様1から13までのいずれかに記載の組成物。
[実施態様15]
耐摩耗添加剤としての、実施態様1から14までのいずれかに記載の組成物の使用。
[実施態様16]
実施態様1から14までのいずれかに記載の組成物の形成方法であって、該方法が、ジチオホスファート誘導体とアミンとを組み合わせることにより組成物を形成するステップを含む、前記方法。
[実施態様17]
分解して硫化水素(H2S)を形成するジチオホスファート誘導体の熱安定性を向上させる方法であって、該方法が、該ジチオホスファート誘導体とアミンとを組み合わせるステップを含み、その際、該アミンが実質的に該ジチオホスファート誘導体の熱分解を防止する、前記方法。
[実施態様18]
ジチオホスファート誘導体の分解温度が少なくとも約60℃である、実施態様16に記載の方法。
[実施態様19]
組み合わせるステップの後に、ジチオホスファート誘導体からのH2S曝露が10ppm(15mg/m3)以下である、実施態様16または17に記載の方法。
[実施態様20]
i)ジチオホスファート誘導体が、実施態様4から7までのいずれかに記載の通りであるか;
ii)アミンが、実施態様8から12までのいずれかに記載の通りであるか;または
iii)i)およびii)の双方である、
実施態様17から19までのいずれかに記載の方法
Claims (15)
- 一般式(I)
R1およびR2は、互いに独立して、C3~C18アルキル、C5~C12シクロアルキル、C5~C6シクロアルキルメチル、C9~C10ビシクロアルキルメチル、C9~C10トリシクロアルキルメチル、フェニル、またはC7~C24アルキルフェニルであるか、または、
R1とR2とが一緒になって(CH3)2C(CH2)2であり;
R3は、水素またはメチルであり;かつ
n+mの合計は、少なくとも2である]
のジチオホスファート誘導体と、数平均分子量(M n )2250未満を有し、ジトリデシルアミンまたはポリアミンから選択されるアミンとの反応生成物を含む組成物であって、前記反応生成物は0.25~2.0の範囲の、ジチオホスファート誘導体のCOOH基の、アミンのアミノ基に対する比である指数を有し、前記組成物が、ASTM D5504に従ってガスクロマトグラフィー(GC)により試験した場合に、10ppm未満のH 2 Sを発生する、
前記組成物。 - 前記反応生成物が、前記組成物の総質量を基準として少なくとも50質量%の量で存在する、請求項1に記載の組成物。
- 前記反応生成物が、前記組成物の総質量を基準として少なくとも25質量%の量で存在する、請求項1に記載の組成物。
- R1およびR2が、互いに独立して、C3~C18アルキル、C5~C6シクロアルキル、またはC7~C18アルキルフェニルである、請求項1に記載の組成物。
- R3が水素であり、かつn+mの合計が2~25である、請求項1から4までのいずれか1項に記載の組成物。
- 前記ジチオホスファート誘導体がβ-ジチオリン酸化プロピオン酸である、請求項1から5までのいずれか1項に記載の組成物。
- さらに遊離ジチオホスファート誘導体を含む、請求項1から6までのいずれか1項に記載の組成物。
- 前記遊離ジチオホスファート誘導体は、前記組成物の総質量を基準として1~75質量%の量で前記組成物中に存在する、請求項7に記載の組成物。
- 耐摩耗添加剤としての請求項1から8までのいずれか1項に記載の組成物。
- さらに、溶媒、基油、水分捕捉剤、乾燥剤、酸化防止剤、金属不動態化剤、防錆剤、分散剤、粘度指数向上剤、流動点降下剤、他の耐摩耗添加剤、およびそれらの組み合わせを含む、請求項9に記載の組成物。
- 請求項1から10までのいずれか1項に記載の組成物の形成方法であって、該方法が、前記ジチオホスファート誘導体と前記アミンとを組み合わせることにより前記組成物を形成するステップを含む、前記方法。
- 分解して硫化水素(H2S)を形成するジチオホスファート誘導体の熱安定性を向上させる方法であって、該方法が、
一般式(I)
R1およびR2は、互いに独立して、C3~C18アルキル、C5~C12シクロアルキル、C5~C6シクロアルキルメチル、C9~C10ビシクロアルキルメチル、C9~C10トリシクロアルキルメチル、フェニル、またはC7~C24アルキルフェニルであるか、または、
R1とR2とが一緒になって(CH3)2C(CH2)2であり;
R3は、水素またはメチルであり;かつ
n+mの合計は、少なくとも2である]
のジチオホスファート誘導体と、数平均分子量(M n )2250未満を有し、ジトリデシルアミンまたはポリアミンから選択されるアミンとを組み合わせて、0.25~2.0の範囲の、ジチオホスファート誘導体のCOOH基の、アミンのアミノ基に対する比である指数での、該ジチオホスファート誘導体と該アミンとの反応生成物を形成するステップを含み、その際、該アミンが実質的に該ジチオホスファート誘導体の熱分解を防止し、且つ前記組み合わせるステップの後に、ASTM D5504に従ってガスクロマトグラフィー(GC)により試験した場合に、10ppm未満のH 2 Sが発生する、前記方法。 - 前記ジチオホスファート誘導体の分解温度が少なくとも60℃である、請求項12に記載の方法。
- 前記アミンがポリアミンポリイソブテンである、請求項1に記載の組成物。
- 前記アミンがポリアミンポリイソブテンである、請求項12に記載の方法。
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