JP5840245B2 - 芳香族アミンおよびカルボン酸官能化ポリマーの反応生成物ならびに分散剤を含有する潤滑組成物 - Google Patents
芳香族アミンおよびカルボン酸官能化ポリマーの反応生成物ならびに分散剤を含有する潤滑組成物 Download PDFInfo
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- 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
- 239000010902 straw Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010689 synthetic lubricating oil Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
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- C10M161/00—Lubricating compositions characterised by the additive being a mixture of a macromolecular compound and a non-macromolecular compound, each of these compounds being essential
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- C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
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Description
一実施形態において、例えば、以下の項目が提供される。
(項目1)
潤滑粘度の油、分散剤、およびアミン官能化添加剤を含む潤滑組成物であって、該アミン官能化添加剤は、少なくとも3つまたは4つの芳香族基を有するアミンから誘導される、潤滑組成物。
(項目2)
前記アミン官能化添加剤は、少なくとも4つの芳香族基を有するアミンから誘導され、少なくとも1つの−NH2官能基および少なくとも2つの第2級または第3級アミノ基を有する、項目1に記載の潤滑組成物。
(項目3)
少なくとも3つまたは4つの芳香族基を有する前記アミンは、下式
式中、各変数は独立であり、
R1は、水素またはC1〜5アルキル基であり、
R2は、水素またはC1〜5アルキル基であり、
Uは、脂肪族、脂環式または芳香族基であり、但し、Uが脂肪族のとき、該脂肪族基は、1から5、または1から2の炭素原子を含む直鎖または分岐アルキレン基であってよく、wは、1から10、または1から4、または1から2、または1である、項目1から2の任意の1項に記載の潤滑組成物。
(項目4)
少なくとも3つまたは4つの芳香族基を有する前記アミンは、ビス[p−(p−アミノアニリノ)フェニル]−メタン、2−(7−アミノ−アクリジン−3−イルメチル)−N−4−{4−[4−(4−アミノ−フェニルアミノ)−ベンジル]−フェニル}−ベンゼン−1,4−ジアミン、またはそれらの混合物である、項目1から3の任意の1項に記載の潤滑組成物。
(項目5)
前記アミン官能化添加剤は、少なくとも3つまたは4つの芳香族基を有する前記アミンをカルボン酸官能化重合体と反応させることによって得られる/得ることができる生成物である、項目1から4の任意の1項に記載の潤滑組成物。
(項目6)
前記アミン官能化添加剤は、(1)イサト酸無水物またはアルキル置換イサト酸無水物と、(2)少なくとも2つの芳香族基および第1級アミノ基または反応性第2級アミノ基を有する芳香族アミンとを反応させるステップを含むプロセスによって得られる/得ることができる少なくとも3つまたは4つの芳香族基を有するアミンから誘導される、項目1に記載の潤滑組成物。
(項目7)
前記カルボン酸官能化重合体は、ポリイソブチレン−無水コハク酸、無水マレイン酸−スチレン共重合体、無水マレイン酸−スチレン共重合体のエステル、アルファオレフィン−無水マレイン酸共重合体、あるいは(i)スチレン−エチレン−アルファオレフィン重合体、(ii)水素化アルケニルアリール共役ジエン共重合体、(iii)無水マレイン酸でグラフトされたポリオレフィン、または(iv)水素化イソプレン重合体、の無水マレイン酸グラフト共重合体、あるいはそれらの混合物である、項目5に記載の潤滑組成物。
(項目8)
前記カルボン酸官能化重合体は、ポリイソブチレン無水コハク酸である、項目7に記載の潤滑組成物。
(項目9)
前記ポリイソブチレン無水コハク酸は、350から5000、または550から3000、または750から2500の数平均分子量を有するポリイソブチレンから誘導される、項目8に記載の潤滑組成物。
(項目10)
前記水素化アルケニルアリール共役ジエン共重合体は、スチレン−ブタジエンの水素化共重合体である、項目7に記載の潤滑組成物。
(項目11)
無水マレイン酸でグラフトされた前記ポリオレフィンは、エチレン−プロピレン共重合体である、項目7に記載の潤滑組成物。
(項目12)
前記水素化イソプレン重合体は、水素化スチレン−イソプレン重合体である、項目7に記載の潤滑組成物。
(項目13)
前記分散剤は、コハク酸イミド分散剤である、項目1から12の任意の1項に記載の潤滑組成物。
(項目14)
前記コハク酸イミド分散剤は、脂肪族ポリアミン、またはその混合物から誘導される、項目13に記載の潤滑組成物。
(項目15)
前記脂肪族ポリアミンは、エチレンポリアミン、プロピレンポリアミン、ブチレンポリアミン、またはそれらの混合物である、項目14に記載の潤滑組成物。
(項目16)
前記脂肪族ポリアミンは、エチレンジアミン、ジエチレントリアミン、トリエチレンテトラアミン、テトラエチレンペンタミン、ペンタエチレンヘキサミン、ポリアミン塔底残渣、およびそれらの混合物からなる群から選ばれる、項目14または15の任意の1項に記載の潤滑組成物。
(項目17)
前記潤滑組成物は、(i)0.5重量%以下の硫黄含有率、(ii)0.1重量%以下のリン含有率、および(iii)1.5重量%以下の硫酸塩灰分含有率を有することを特徴とする、項目1から16の任意の1項に記載の潤滑組成物。
(項目18)
磨耗防止剤、分散剤粘度調整剤、摩擦調整剤、粘度調整剤、酸化防止剤、過塩基性洗剤の少なくとも1つ、またはそれらの混合物をさらに含む、項目1から17の任意の1項
に記載の潤滑組成物。
(項目19)
前記摩擦調整剤は、アミンの長鎖脂肪酸誘導体、長鎖脂肪酸エステル、長鎖脂肪族エポキシド、脂肪族イミダゾリン、アルキルリン酸のアミン塩、脂肪族アルキル酒石酸エステル、脂肪族アルキル酒石酸イミド、および脂肪族アルキル酒石酸アミドからなる群から選ばれる、項目18に記載の潤滑組成物。
(項目20)
分散剤粘度調整剤をさらに含む、項目1から19の任意の1項に記載の潤滑組成物。
(項目21)
前記分散剤粘度調整剤は、15から80モルパーセントのエチレン、20から85モルパーセントのC3〜10アルファモノオレフィン、および0から15モルパーセントの非共役ジエンまたはトリエンの重合体へのオレフィンカルボン酸アシル化剤のグラフト化であって、該重合体は5000から500,000の範囲の平均分子量を有するグラフト化ならびに、該グラフト化した重合体をアミンとさらに反応させることによって調製される、項目20に記載の潤滑組成物。
(項目22)
前記分散剤粘度調整剤は、(a)カルボン酸官能基またはその反応性等価物を含む重合体であって、5,000より大きな数平均分子量を有する重合体と、(b)前記カルボン酸官能基と縮合してペンダント基、および少なくとも1つの窒素、酸素、または硫黄原子を含む少なくとも1つの追加の基を提供することができる、少なくとも1つのアミノ基を含む少なくとも1つの芳香族アミンを含むアミン成分との反応生成物であって、該芳香族アミンは、(i)ニトロ置換アニリン、(ii)−C(O)NR−基、−C(O)O−基、−O−基、−N=N−基、または−SO2−基によって結合されている2つの芳香族部分を含むアミンであって、Rは、水素またはヒドロカルビルであり、該芳香族部分の1つは該縮合可能なアミノ基を有するアミン、(iii)アミノキノリン、(iv)アミノベンゾイミダゾール、(v)N,N−ジアルキルフェニレンジアミン、および(vi)環置換ベンジルアミンからなる群から選ばれる、項目20に記載の潤滑組成物。
(項目23)
リン含有磨耗防止剤をさらに含む、項目1から22の任意の1項に記載の潤滑組成物。
(項目24)
過塩基性洗剤をさらに含む、項目1から23の任意の1項に記載の潤滑組成物。
(項目25)
前記過塩基性洗剤は、フェナート、硫黄含有フェナート、スルホナート、サリキサラート、サリチラート、およびそれらの混合物からなる群から選ばれる、項目24に記載の潤滑組成物。
(項目26)
内燃機関を潤滑する方法であって、該内燃機関に項目1から25の任意の1項に記載の潤滑組成物を供給することを含む方法。
本発明の分散剤は、コハク酸イミド分散剤、またはその混合物であってよい。一実施態様において、分散剤は、単独の分散剤として存在してもよい。一実施態様において、分散剤は、2つまたは3つの異なる分散剤の混合物中に存在してもよく、少なくとも1つは、コハク酸イミド分散剤であってよい。
(a)数平均分子量300〜10,000を有するポリイソブチレン、前記ポリイソブチレンのモル数を基準として90モルパーセントの4置換および3置換末端基、およびハロゲンを含む混合物を形成させ、150℃未満の温度において加熱するステップであって、前記ハロゲンは、最大で末端基の前記モル数と等しい量のモル量で前記混合物に加えられるステップ、
(b)前記ハロゲンの添加に続いてまたは前記ハロゲンの添加と同時に、前記混合物にα,β−不飽和酸(通常、マレイン酸)またはα,β−不飽和無水物(通常、マレイン酸無水物)化合物を加えるステップ、
(c)前記混合物の温度を170℃から220℃に増加させ、前記ポリイソブチレンを前記α,β−不飽和酸または前記α,β−不飽和無水物化合物と反応させるのに十分な時間混合物を前記温度に保持するステップ、
(d)前記混合物を200℃未満に冷却し、等しいモル量の前記ハロゲンおよび前記α,β−不飽和酸または前記α,β−不飽和無水物化合物をそれに加えるステップ、ならびに
(e)前記混合物の温度を220℃未満の限度に増加させ、前記混合物中の未反応α,β−不飽和酸またはα,β−不飽和無水物化合物を3パーセント未満に減らすのに十分な時間前記温度に保持するステップ、
を含む方法(米国特許第6,165,235号に記載されている)によって調製することができ、前記方法は、2,000ppm未満の塩素含有率を有するポリイソブチレン置換カルボン酸アシル化剤を製造する。
本発明の潤滑組成物は、アミン官能化添加剤をさらに含む。アミン官能化添加剤は、少なくとも3つまたは4つの芳香族基を有するアミンから誘導することができる。
R1は、水素またはC1〜5アルキル基(通常は水素)であってよく、
R2は、水素またはC1〜5アルキル基(通常は水素)であってよく、
Uは、脂肪族、脂環式、または芳香族基であってよく、但し、Uが脂肪族のとき、脂肪族基は、1から5、または1から2の炭素原子を含む直鎖または分岐アルキレン基であってよく、
wは、1から10、または1から4、または1から2(通常は1)であってよい)
によって表すことができる。
R1は、水素またはC1〜5アルキル基(通常は水素)であってよく、
R2は、水素またはC1〜5アルキル基(通常は水素)であってよく、
Uは、脂肪族、脂環式、または芳香族基であってよく、但し、Uが脂肪族のとき、脂肪族基は、1から5、または1から2の炭素原子を含む直鎖または分岐アルキレン基であってよく、
wは、1から10、または1から4、または1から2(通常は1)であってよい)
によって表すことができる。
der Deutschen Chemischen Gesellschaft(1910),43,728〜39に記載されている方法論によって調製することができる。
アミン官能化添加剤は、少なくとも3つまたは4つの芳香族基を有するアミンとカルボン酸官能化重合体との反応生成物であってよい。得られる生成物は、アミン官能化カルボン酸官能化重合体であるとして記載することができる。
(i)米国特許第6,544,935号から、無水マレイン酸およびスチレンを含む重合体のエステルが知られている。
R1、R2およびUは、既に記載されており、
BBは、重合体主鎖であってよく、ポリイソブチレン、あるいは(i)水素化アルケニルアリール共役ジエン共重合体(特に、スチレン−ブタジエンの水素化共重合体)、(ii)ポリオレフィン(特にエチレン−アルファオレフィン、例えばエチレン−プロピレン共重合体)、(iii)水素化イソプレン重合体(特に水素化スチレン−イソプレン重合体)、または(iv)イソプレンとイソブチレンとの共重合体、の共重合体であってよい。BBは、式(4)および(5)に示されているように、1つのコハク酸イミド基で置換されていてもよく、または複数のコハク酸イミド基で置換されていてもよい。一実施態様において、BBは、イソプレンとイソブチレンとの共重合体であってよい。
一実施態様において、任意選択として、アミン官能化添加剤の構造内に追加のポリアミンまたはモノアミンが存在してよい。追加のポリアミンまたはモノアミンは、アミン官能化添加剤の全酸価(TAN:totoal acid number)を調節する上で助けとすることができる。
任意選択として、アミン官能化添加剤は、キャッピングアミン、またはそれらの混合物とさらに反応することができる。キャッピングアミンを用いて、本発明のアミン官能化添加剤の全酸価(本明細書においては以後TANと称される)を調整(通常はTANの低下)することができる。必要なら、キャッピングアミンは、他の添加剤、例えば洗剤に対するいずれかの悪影響を最小にする量で未反応カルボキシル基をキャップすることができる。悪影響は、ゲルの形成を生じさせるアミン含有添加剤と洗剤との間の相互作用を含んでよい。一実施態様において、アミン官能化添加剤は、キャッピングアミンとさらに反応することができる。一実施態様において、アミン官能化添加剤は、キャッピングアミンとさらに反応しない。
088]に、キャッピングアミンのより詳細な記述が記載されている。
潤滑組成物は、潤滑粘度の油を含む。そのような油は、天然油および合成油、水素化分解、水素化、および水素化精製から誘導した油、未精製油、精製油、再精製油、またはそれらの混合物を含む。国際公開第2008/147704号の段落[0054]から[0056]に、未精製油、精製油、および再精製油のより詳細な記載が提供されている。国際公開第2008/147704号の段落[0058]から[0059]に、天然潤滑油および合成潤滑油のより詳細な記述がそれぞれ記載されている。合成油は、フィッシャー・トロプシュ反応によって製造してもよく、通常、水素化異性化フィッシャー・トロプシュ炭化水素またはワックスであってよい。一実施態様において、油は、フィッシャー・トロプシュ気体−液体合成手順によって調製してもよく、他の気体−液体油であってもよい。
本組成物は、任意選択として、他の性能添加剤を含む。他の性能添加剤は、金属不活性化剤、粘度調整剤、洗剤、摩擦調整剤、磨耗防止剤、腐食抑制剤、分散剤(上記に記載されている本発明の分散剤以外)、分散剤粘度調整剤(上記に記載されている本発明のアミン官能化添加剤以外)、極圧添加剤、酸化防止剤、発泡防止剤、解乳化剤、流動点降下剤、シール膨潤剤の少なくとも1つ、およびそれらの混合物を含む。通常、完全に調合した潤滑油は、これらの機能性添加剤の1つ以上を含む。
1.3重量%の酸化防止剤(硫化オレフィン、ヒンダードフェノール、およびアルキル化ジフェニルアミンの混合物)、1重量%の亜鉛ジアルキルジチオホスファート、2.8重量%の洗剤混合物(カルシウムスルホナートおよびカルシウムフェナートを含む)を含む一連のSAE 15W−40エンジン潤滑剤を調製する。潤滑剤は、指定された量のコハク酸イミド分散剤と、調製実施例1または調製実施例2のどちらかの生成物とを含む。コハク酸イミド分散剤および調製実施例1および2の生成物の量を以下の表に示す。
煤試験において潤滑剤を評価する。1体積%の硫酸と硝酸との17.4M混合物(10:1)(TBNを11減少させると計算される酸の量)の添加によって潤滑剤にストレスを加える。酸ストレスを加えた試料を6重量%のカーボンブラック(煤モデル)および5重量%のディーゼル燃料でトップ処理する。次に、潤滑剤混合物をティッシュマイザー中でホモジナイズしてスラリーとする。次に、スラリーに超音波照射してカーボンブラックを完全に分散させる。試料中に空気中0.27%の亜酸化窒素を0.5cc分−1吹き込みながら、分散試料を90℃で7日間保存する。1日に1回、25マイクロリットルの分量の試料をクロマトグラフィーペーパーに載せる。ろ紙を90℃で2時間硬化した後、外側のオイルスポットに対する内側のカーボンブラック含有スポットの直径の比を測定し、7日間にわたっての平均とし、煤比として表に報告する。煤比が高いほど、煤分散改善を示す。得られた結果は、以下の通りである。
コハク酸イミド分散剤の量以外は上記に記載したものと同様な一連のSAE 15W−40潤滑剤を調製し、調製実施例1および2の生成物を以下の表に示す。
次に、SAE 15W−40潤滑剤をシール試験において評価してAK6 Viton(登録商標)シールの引張り強さおよび破断伸び率を評価する。評価は、Mercedes−Benz供給規格(MB DBL 6674)に記載されている方法論によって行われる。得られるシール引張り強さおよび破断伸び率の結果は、以下である。
Claims (17)
- 潤滑粘度の油、分散剤、およびアミン官能化添加剤を含む潤滑組成物であって、該アミン官能化添加剤は、(1)イサト酸無水物またはアルキル置換イサト酸無水物と、(2)少なくとも2つの芳香族基および第1級アミノ基または反応性第2級アミノ基を有する芳香族アミンとを反応させるステップを含むプロセスによって得られる/得ることができる少なくとも3つの芳香族基を有するアミンから誘導される、潤滑組成物。
- 前記分散剤は、コハク酸イミド分散剤である、請求項1に記載の潤滑組成物。
- 前記コハク酸イミド分散剤は、脂肪族ポリアミン、またはその混合物から誘導される、請求項2に記載の潤滑組成物。
- 前記脂肪族ポリアミンは、エチレンポリアミン、プロピレンポリアミン、ブチレンポリアミン、またはそれらの混合物である、請求項3に記載の潤滑組成物。
- 前記脂肪族ポリアミンは、エチレンジアミン、ジエチレントリアミン、トリエチレンテトラアミン、テトラエチレンペンタミン、ペンタエチレンヘキサミン、ポリアミン塔底残渣、およびそれらの混合物からなる群から選ばれる、請求項3または4に記載の潤滑組成物。
- 前記潤滑組成物は、(i)0.5重量%以下の硫黄含有率、(ii)0.1重量%以下のリン含有率、および(iii)1.5重量%以下の硫酸塩灰分含有率を有することを特徴とする、請求項1から5の任意の1項に記載の潤滑組成物。
- 磨耗防止剤、分散剤粘度調整剤、摩擦調整剤、粘度調整剤、酸化防止剤、過塩基性洗剤の少なくとも1つ、またはそれらの混合物をさらに含む、請求項1から6の任意の1項に
記載の潤滑組成物。 - 前記摩擦調整剤は、アミンの長鎖脂肪酸誘導体、長鎖脂肪酸エステル、長鎖脂肪族エポキシド、脂肪族イミダゾリン、アルキルリン酸のアミン塩、脂肪族アルキル酒石酸エステル、脂肪族アルキル酒石酸イミド、および脂肪族アルキル酒石酸アミドからなる群から選ばれる、請求項7に記載の潤滑組成物。
- 分散剤粘度調整剤をさらに含む、請求項1から8の任意の1項に記載の潤滑組成物。
- 前記分散剤粘度調整剤は、15から80モルパーセントのエチレン、20から85モルパーセントのC3〜10アルファモノオレフィン、および0から15モルパーセントの非共役ジエンまたはトリエンの重合体へのオレフィンカルボン酸アシル化剤のグラフト化であって、該重合体は5000から500,000の範囲の平均分子量を有するグラフト化ならびに、該グラフト化した重合体をアミンとさらに反応させることによって調製される、請求項9に記載の潤滑組成物。
- 前記分散剤粘度調整剤は、(a)カルボン酸官能基またはその反応性等価物を含む重合体であって、5,000より大きな数平均分子量を有する重合体と、(b)前記カルボン酸官能基と縮合してペンダント基、および少なくとも1つの窒素、酸素、または硫黄原子を含む少なくとも1つの追加の基を提供することができる、少なくとも1つのアミノ基を含む少なくとも1つの芳香族アミンを含むアミン成分との反応生成物であって、該芳香族アミンは、(i)ニトロ置換アニリン、(ii)−C(O)NR−基、−C(O)O−基、−O−基、−N=N−基、または−SO2−基によって結合されている2つの芳香族部分を含むアミンであって、Rは、水素またはヒドロカルビルであり、該芳香族部分の1つは該縮合可能なアミノ基を有するアミン、(iii)アミノキノリン、(iv)アミノベンゾイミダゾール、(v)N,N−ジアルキルフェニレンジアミン、および(vi)環置換ベンジルアミンからなる群から選ばれる、請求項9に記載の潤滑組成物。
- リン含有磨耗防止剤をさらに含む、請求項1から11の任意の1項に記載の潤滑組成物。
- 過塩基性洗剤をさらに含む、請求項1から12の任意の1項に記載の潤滑組成物。
- 前記過塩基性洗剤は、フェナート、硫黄含有フェナート、スルホナート、サリキサラート、サリチラート、およびそれらの混合物からなる群から選ばれる、請求項13に記載の潤滑組成物。
- 前記アミン官能化添加剤は、カルボン酸官能化重合体を前記少なくとも3つの芳香族基を有するアミンと反応させることによって得られる/得ることができる生成物である、請求項1から14の任意の1項に記載の潤滑組成物。
- 前記アミン官能化添加剤は、カルボン酸を前記少なくとも3つの芳香族基を有するアミンと反応させることによって得られる/得ることができる生成物である、請求項1から14の任意の1項に記載の潤滑組成物。
- 内燃機関を潤滑する方法であって、該内燃機関に請求項1から16の任意の1項に記載の潤滑組成物を供給することを含む方法。
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US20160075966A1 (en) | 2016-03-17 |
CN102414300A (zh) | 2012-04-11 |
JP2012519222A (ja) | 2012-08-23 |
US20130310287A1 (en) | 2013-11-21 |
JP5735434B2 (ja) | 2015-06-17 |
CN102414300B (zh) | 2014-07-23 |
EP2401348A1 (en) | 2012-01-04 |
US9644167B2 (en) | 2017-05-09 |
WO2010099136A1 (en) | 2010-09-02 |
KR20110132394A (ko) | 2011-12-07 |
US20120046206A1 (en) | 2012-02-23 |
CA2753414A1 (en) | 2010-09-02 |
EP2431448B1 (en) | 2017-11-15 |
US8569217B2 (en) | 2013-10-29 |
KR101539817B1 (ko) | 2015-07-27 |
JP2014111794A (ja) | 2014-06-19 |
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