JPS6231040B2 - - Google Patents

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Publication number
JPS6231040B2
JPS6231040B2 JP58180982A JP18098283A JPS6231040B2 JP S6231040 B2 JPS6231040 B2 JP S6231040B2 JP 58180982 A JP58180982 A JP 58180982A JP 18098283 A JP18098283 A JP 18098283A JP S6231040 B2 JPS6231040 B2 JP S6231040B2
Authority
JP
Japan
Prior art keywords
parts
mixture
hours
oil
fuel
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
Application number
JP58180982A
Other languages
English (en)
Other versions
JPS59135205A (ja
Inventor
Piitaason Buraianto Chaaruzu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lubrizol Corp
Original Assignee
Lubrizol Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Lubrizol Corp filed Critical Lubrizol Corp
Publication of JPS59135205A publication Critical patent/JPS59135205A/ja
Publication of JPS6231040B2 publication Critical patent/JPS6231040B2/ja
Granted legal-status Critical Current

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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
    • 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
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G73/00—Recovery or refining of mineral waxes, e.g. montan wax
    • C10G73/38—Chemical modification of petroleum
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
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Description

【発明の詳細な説明】 この発明は潤滑剤および通常液状の燃料に用い
て有用な清浄・分散剤に関する。
その構造内に親水性および親油性の両方の基が
存在する比較的高分子量の組成物を通常液体の燃
料（例えば、ガソリン、ジエツト燃料、ケロセ
ン、燃料油、暖房用油等）や天然および合成の潤
滑剤用の添加剤として使用することは当該技術分
野においてよく知られている。例えば、シー・ブ
イ・スマルヒア（C.V.Smalheer）およびアー
ル・ケネデイ・スミス（R.Kennedy Smith）著
「ルブリカント・アデイテイブズ」（Lubricant
Additives）（the Lezius―Hiles Co.刊）特に２
〜５頁、およびエム・ダブリユー・ラニー（M.
W.Ranney）著「ルブリカント・アデイテイブ
ズ」（Lubricant Additives）（the Noyes Data
Corp.刊，1973年）特に３〜92頁参照）。
燃料および潤滑剤中に使用されてきている添加
剤の中には、米国特許第3701640号、同第3558743
号および同第3493520号に記載されているものが
ある。
上記後二者の米国特許に記載されているもの
は、カルボン酸含有もしくはカルボン酸無水物含
有付加共重合体、アミン、アルキル化フエノール
およびアルデヒドを反応させることによつて製造
されている。また上記米国特許第3701640号に記
載されている添加剤は、カルボン酸を、少なくと
も３個の窒素原子（そのうち少なくとも２個は一
級であり、少なくとも１個は二級である）を有す
るポリアミン、アルキル置換フエノールおよびホ
ルムアルデヒドと反応させることによつて製造さ
れている。
米国特許第3787458号および同第3793202号に
は、フエノールをホルムアルデヒドおよびアミン
と縮合させ、ついで生成物を酸またはアルデヒド
で処理して得たものが記載されている。
上記従来技術によつて明らかとなつた知見にも
かかわらず、燃料および潤滑剤用の新規な添加剤
に対する研究が続けられている。この研究は、機
関の操作に帰因する汚染を減少させたり、また、
経済性や原料不足などの原因からさらに促進され
てきている。この発明の目的は、これら増加する
諸要求に適合する添加剤の製造方法を提供するこ
とにある。
この発明によれば、 (A)一般式 （ここで、Ｒは数平均分子量885ないし1040の
ポリブチル基）で表わされるアルフアーヒドロキ
シアルキルヒドロキシ芳香族化合物もしくはその
ポリスルフイドを(B)無水マレイン酸、無水クロロ
マレイン酸およびアクリル酸よりなる群の中から
選ばれた酸系反応体と反応させ、ついで３個ない
し７個のアミノ基を有するポリエチレンポリアミ
ンまたはペンタエリスリトールで処理して得たこ
とを特徴とする潤滑油または燃料用清浄・分散剤
が提供される。
式（）で示される反応体(A)は常法に従いフエ
ノールを、ルイス酸例えばBF3，AlCl3，SnCl4等
の存在下に、Ｒ―Ｈ（ここで、Ｒは上記の通り）
で示されるポリブチレンでアルキル化して得られ
る式 （ここで、Ｒは上記の通り）で示されるポリブ
テニル置換フエノールを、塩基物質（例えば金属
酸化物、水酸化物、アルコキシド、炭酸塩、硫化
物、メルカプチド等）の存在下、例えばホルムア
ルデヒド、パラホルムアルデヒド等のカルボニル
試薬とモル比0.5ないし5.0好ましくは１ないし２
の割合で30ないし300℃好ましくは50ないし125℃
で反応させることによつて製造される。反応体(A)
としては、式（）のポリブテニル置換ヒドロキ
シメチルフエノールを硫化剤（例えば硫化水素）
と反応させて得たスルフイドであつてもよい。
この発明の清浄・分散剤は、まず、上記アルフ
アヒドロキシアルキルアルキル化ヒドロキシ芳香
族化合物を無水マレイン酸、無水クロロマレイン
酸またはアクリル酸と反応させることによつて製
造される。この反応は50℃ないし、存在する反応
体もしくは生成物のうちの最低分解温度に相当す
る分解温度までの温度で反応させる。好ましくは
最低反応温度は100℃、さらに好ましくは150℃で
あり、一方、最高温度は好ましくは300℃、さら
に好ましくは250℃である。一般に反応体(A)と反
応体(B)とのモル比は0.5：１ないし２：１であ
る。この反応は通常0.5ないし96時間でおこなわ
れる。この反応を、炭化水素、アルコール類、あ
るいはエーテル類のような実質的に不活性な通常
液状の溶剤・希釈剤または以下に記すような潤滑
剤ベースストツクの存在の下におこなうのがしば
しば望ましい。
上記反応終了後、この反応混合物を３個ないし
７個のアミノ基を有するポリエチレンアミンまた
はペンタエリスリツトで処理してアミドやエステ
ルに転化することによつてこの発明の清浄・分散
剤が得られる。このような処理方法自体はよく知
られているところである。
この後処理によつてクランクケース分散性を潤
滑剤に付与したり、気化器清浄性を燃料に付与し
たりするといつた新しい性質を導入することがで
き、このことはこの後処理生成物を非常に望まし
いものとし、かつ、有用なものとしている。上記
の縮合生成物から誘導される過塩基性金属塩は、
ある場合、ゲル化剤、とくに有機流体用のそれと
して有用なものである。
以下にこの発明の実施例を記す。とくに指示が
ないかぎり、全て「部」および「％」は重量基準
である。
実施例 １(a) ポリイソブチルフエノール（ポリイソブチル基
の885）1040部および希釈油326部の混合物
を、55℃で、水酸化ナトリウムの飽和水溶液４部
で処理した。混合物の温度を75℃に上昇させて、
パラホルムアルデヒド72部を加えた。この混合物
を75℃でさらに２時間保持し、ついで30℃で16時
間保持した。このヒドロキシ触媒を酢酸４部で中
和し、この反応混合物にさらに希釈油480部を加
えて40〜75℃／８トルでストリツピングした。残
つた油溶液につき赤外線分析をしたところ所望の
ヒドロキシメチル中間体の生成が確認された。
実施例 １(b) 実施例１(a)の油溶液1918部と無水マレイン酸
150部との混合物を３時間かけてゆつくりと194℃
に加熱し、190〜195℃で２時間保つた。ついでこ
れを190℃／10トルまでストリツピングし、ろ過
助材を用いてろ過して所望の縮合生成物を得た。
実施例 １(c) 実施例１(b)の油溶液1453部に、85℃で、分子当
り３ないし７個のアミノ基を有する市販のポリエ
チレンポリアミン混合物63.5部を徐徐に加えた。
ついで、この反応混合物を165℃に加熱し、この
温度に３時間保つた。この間窒素を吹込んだ。室
温で一晩放置したのち、窒素を吹込みながら３時
間で175℃に加熱し、ついで170℃／８トルで１時
間ストリツピングした。ろ過助材を通してろ過し
て所望の後処理生成物の油溶液を得た。
実施例 ２(a) 実施例１(a)で用いたポリイソブチル置換フエノ
ール4480部と希釈油3099部との混合物に、40℃
で、水酸化ナトリウムの濃水溶液32部およびパラ
ホルムアルデヒド290部を添加した。この混合物
を80〜85℃で15時間保持し、ついで、塩基性触媒
を中和するために酢酸36部を加えた。この混合物
を110〜130℃で、合せて12時間保持し、ケイソウ
土を通してろ過したところ、所望のヒドロキシメ
チル中間体を含有する油溶液7051部を得た。
実施例 ２(b) 実施例２(a)の油溶液1258部に90℃でアクリル酸
56部を徐々に加えた。反応温度を1.5時間かけて
ゆつくりと180℃に上昇し、180〜210℃で４時間
保持した。この混合物を190℃／20トルまでスト
リツピングし、ろ過して所望の縮合生成物の油溶
液を得た。
実施例 ２(c) 実施例２(b)の縮合生成物1020部に実施例１で用
いたポリエチレンポリアミン30.8部を加えた。反
応温度を１時間かけて165℃にし、150〜165℃で
８時間保つた。この間窒素を吹込んだ。この混合
物をろ過して所望の後処理生成物の油溶液933部
を得た。
実施例 ３(a) 実施例１(a)と同様にして得たヒドロキシメチル
フエノール1268部と希釈油248部との混合物に、
50℃で、無水クロロマレイン酸108部を加えた。
この反応混合物を195℃に加熱し、この温度で11
時間保持した。ついでこれを150℃に冷却し、170
℃／10トルまでストリツピングした。こうして得
た残りの混合物をろ過助材を通してろ過したとこ
ろ、所望の縮合生成物の油溶液を得た。
実施例 ３(b) 希釈油288部と実施例１で用いたポリエチレン
ポリアミン61.5部との混合物に、70℃で、実施例
５(a)の油溶液1200部を加えた。この混合物を160
℃で１時間保持し、ついで２時間かけて195℃に
加熱した。ついで、これを150℃に冷却し、ケイ
ソウ土を通してろ過して所望の生成物の油溶液を
得た。
実施例 ３(c) 実施例１(b)の縮合生成物1145部とペンタエリス
リトーン72部との混合物を1.5時間かけて220℃に
加熱し、この温度でさらに７時間保持した。つい
で、この混合物に希釈油80グラムを添加し、120
℃でろ過助材を用いてろ過したところ所望のエス
テルの油溶液を得た。
実施例 ４(a) ポリイソブチルフエノール（ポリイソブチル基
の1037）5180部、水酸化ナトリウムペレツト
200部およびストツダードソルベント1000部から
なる混合物を２1/2時間かけて60〜160℃に加熱し
た。ついで、160〜190℃で3.5時間、この混合物
に窒素を吹込み、その間水を共沸留去した。そし
て、これをさらに5.5時間、190〜197℃で加熱し
た。ついで、S2Cl2337部を３時間かけて滴下させ
てこの混合物を処理した。この滴下の間に、この
混合物に0.2cfhの割で窒素を吹込み、発生した
H2SもしくはHClを補捉するために苛性アルカリ
を用いた。この滴下が終つてから、この混合物を
130〜135℃でさらに２時間加熱した。ついで、35
℃でこれに水650部、塩酸水溶液20部およびトル
エン750部を加えた。これを、全部で15時間かけ
て100℃に加熱し、その間、1cfhの割合で窒素を
吹込んだ。この混合物に希釈油1325部とケイソウ
土100部を添加した。この混合物を、100℃で、ケ
イソウ土属を通してろ過して沈でんした塩を除去
した。183℃／25トルまでストリツピングしたと
ころ所望のポリスルフイド架橋生成物を得た。
実施例 ４(b) 実施例４(a)のポリスルフイド架橋生成物641
部、パラホルムアルデヒド16部およびブタノール
32部からなる混合物を105〜135℃で13時間加熱
し、その間、1cfhの割合で窒素を吹込んだ。この
混合物を134℃／21トルまでブタノールと水につ
いてストリツピングした。この混合物に無水マレ
イン酸（71部）を加え、2.5時間かけて205℃に加
熱した。ついで、これを205〜210℃で5.5時間保
持し、210℃／19トルまでストリツピングした。
希釈油250部を加えてから、この混合物を、130℃
で、ろ過助材を通してろ過して所望の縮合生成物
の油溶液を得た。
実施例 ５(a) 実施列１(a)と同様にして得たヒドロキシメチル
化フエノール1155部と希釈油825部との混合物に
50℃でα―メチレングルタロニトリル160部を加
えた。この反応混合物を２時間かけて195℃に、
ついで0.5時間かけて205℃に熱し、この温度で１
時間保持した。ついで、これを200℃に冷却し、
200℃／10torrまでストリツピングした。得られ
た残分をろ過助材を通してろ過して所望縮合生成
物の油溶液を得た。
実施例 ５(b) 実施例５(a)で得た油溶液510部に、110℃で、分
子当り３〜７個のアミノ基を有する市販のポリエ
チレンポリアミン混合物26部をゆつくりと加え
た。ついで、この反応混合物を165℃に熱し、窒
素を吹き込みながらこの温度に２時間保持した。
窒素を吹き込みながらこの混合物を185℃に熱
し、190℃／20torrまでストリツピングした。ろ
過助剤を通してろ過することによつて所望生成物
の油溶液を得た。
既に述べたように、この発明の清浄・分散剤
は、とくに、潤滑油が高温環境や、停止・発進を
何度もおこなう自動車運転にみられるような繰返
し応力に供される潤滑剤組成物を調製するときの
添加剤として有用である。このような組成物の多
くが、エンジンスラツジの分散やエンジン摩耗の
減少にとくに有用である。この発明の生成物は、
潤滑粘度を有する種々の油系潤滑剤に使用するこ
とができる。この油としては、天然および合成の
潤滑油さらにはそれらの混合物がある。これら潤
滑剤組成物には、自動車およびトラツク用エンジ
ン、２サイクルエンジン、ロータリーエンジン、
航空機用ピストンエンジン、舶用および鉄道用ジ
ーゼルエンジン等のような火花点火式および圧縮
点火式内燃機関用のクランクケース潤滑油があ
る。さらに、自動伝達流体、伝達軸用潤滑剤、ギ
ヤ潤滑剤、金属加工用潤滑剤、圧力流体および他
の潤滑油やグリース組成物に用いても有用であ
る。
これら組成物を製造するのに有用な天然油に
は、獣油および植物油（例えば、ひまし油やラー
ド油）、さらには、液体石油あるいはパラフイン
系、ナフテン系もしくは混合パラフイン系―ナフ
テン系の溶剤処理もしくは酸処理の鉱物性潤滑油
等がある。石炭や頁岩から誘導された潤滑粘度を
有する油も有用な基油である。合成潤滑油には、
重合および相互重合オレフイン（例えば、ポリブ
チレン類、ポリプロピレン類、プロピレン―イソ
ブチレン共重合体、塩素化ポリブチレン類等）の
ような炭化水素油、アルキルベンゼン類（例え
ば、ドデシルベンゼン類、テトラデシルベンゼン
類、ジノニルベンゼン類、ジ―（２―エチルヘキ
シル）―ベンゼン類等）、ポリフエニル類（例え
ば、ビフエニル類、テルフエニル類等）等があ
る。
酸化アルキレンの重合体および共重合体、さら
には、末端のヒドロキシル基がエステル化、エー
テル化等によつて変性されているそれらの誘導体
も公知合成潤滑油の他の群を構成する。この例を
挙げると、酸化エチレンや酸化プロピレンの重合
によつて得た油、これらポリオキシアルキレン重
合体のアルキルおよびアリールエーテル類（例え
ば、平均分子量1000のメチルポリイソプロピレン
グリコールエーテル、分子量500〜1000のポリエ
チレングリコールのジフエニルエーテル、分子量
1000〜1500のポリプロピレングリコールのジエチ
ルエーテル等）、あるいはこれらのモノおよびポ
リカルボン酸エステル類例えば、酢酸エステル
類、混合C3〜C8脂肪酸エステルもしくはテトラ
エチレングリコールのC13オキソ酸ジエステルで
ある。
合成潤滑油の他の好適な群は、ジカルボン酸
（例えば、フタル酸、コハク酸、マレイン酸、ア
ゼライン酸、スベリン酸、セバシン酸、フマル
酸、アジピン酸、リノレイン酸二量体等）と種々
のアルコール（例えば、ブチルアルコール、ヘキ
シルアルコール、ドデシルアルコール、２―エチ
ルヘキシルアルコール、エチレングリコール等）
とのエステル類からなる。これらエステル類の具
体的な例を挙げると次のとおりである。すなわ
ち、アジピン酸ジブチル、セバシン酸ジ（２―エ
チルヘキシル）、フマル酸ジノルマルヘキシル、
セバシン酸ジオクチル、アゼライン酸ジイソオク
チル、アゼライン酸ジイソデシル、フタル酸ジオ
クチル、フタル酸ジデシル、セバシン酸ジエイコ
シル、リノレイン酸二量体の２―エチルヘキシル
ジエステル、セバシン酸１モルとテトラエチレン
グリコール２モルおよび２―エチルカプロン酸２
モルとの複合エステル等である。
合成油として有用なエステル類には、さらに、
C5〜C12モノカルボン酸とポリオールとから製造
したものや、トリメチロールプロパン、ペンタエ
リスリトール、ジペンタエリスリトールのような
ポリオールエーテル類がある。
ポリアルキル―、ポリアリール―、ポリアルコ
キシ―、あるいはポリアリールオキシ―シロキサ
ン油やシリケート油のようなシリコン系油も合成
潤滑剤の別の有用な群を構成する（例えば、ケイ
酸テトラエチル、ケイ酸テトライソプロピル、ケ
イ酸テトラ（２―エチルヘキシル）、ケイ酸テト
ラ（４―メチル―２―テトラエチル）、ケイ酸テ
トラ（パラ第三ブチルフエニル）、ヘキシル―
（４―メチル―２―ペントキシ）―ジシロキサ
ン、ポリ（メチル）シロキサン類、ポリ（メチル
フエニル）シロキサン類等）。他の合成潤滑油に
は、リン含有酸の液状エステル類（例えば、リン
酸トリクレジル、リン酸トリオクチル、デカンホ
スホン酸のジエチルエステル等）、重合テトラヒ
ドロフラン等がある。
この発明の清浄・分散剤を含む潤滑剤組成物用
のベースストツクとして働く好ましい潤滑油は０
〓約100センチストークスないし210〓で2000セン
チストークスに恒る粘度を有している。
一般に、上記潤滑剤組成物はこの発明の清浄・
分散剤を該組成物に防さび性、スラツジ分散性お
よびエンジン清浄性を付与するに充分な量含んで
いる。通常、この量は、潤滑剤組成物総重量の
0.05ないし20％、好ましくは0.50ないし10％であ
る。潤滑油が、舶用ジーゼルエンジンに使用され
る場合のように、とくに悪い条件下で使われる場
合は、この発明の清浄・分散剤が約30重量％まで
存在していてもかまわない。
上記潤滑剤組成物は、この発明の清浄・分散剤
に加えて、通常潤滑剤中に使用されている他の添
加剤を含んでいてもよい。このような添加剤に
は、例えば、灰生成型および無灰型の補助清浄
剤、粘度指数向上剤、流動点降下剤、消泡剤、極
圧剤、防さび剤、酸化防止剤および腐食防止剤が
ある。
この発明の清浄・分散剤を含む通常液状の燃料
組成物は、一般に、石油源例えば、通常液状の石
油留分燃料から誘導される。もつとも、該組成物
は、フイツシヤー・トロプシユ法やそれに関連し
た方法によつて合成されたものや有機廃棄物の処
理あるいは石炭、亜炭もしくは頁岩の処理によつ
て得られたものを含むものであつてもよい。この
燃料組成物は、その使用目的に応じて種々の、沸
点範囲、粘度、曇点、流動点等を有している。こ
のような燃料には、モータおよび航空機用ガソリ
ン、ジーゼル燃料、ジエツトエンジン燃料、ケロ
セン、留分燃料、暖房用油、残査燃料、バンカー
重油等がある。このような燃料の諸特性は当業者
にはよく知られている。例えば、ASTMD仕様書
Ｄ＃369―73（燃料油）およびＤ＃439―73（ガソ
リン類）参照。
上記燃料組成物は、この発明の清浄・分散剤を
0.001％ないし５％（最終組成分の重量に対し）、
好ましくは0.001％ないし１％含んでいる。この
生成物は、その組成や選定された燃料混合物に応
じて、燃料組成物に多くの望ましい特性を付与す
ることができる。例えば、ガソリン中において
は、それは、それを含んだ組成物が接触する金属
部の腐食防止性を該組成物に付与したり、燃料の
気化器清浄性を増したり気化器着氷性を減少させ
たりする。また一方、この生成物は燃料油組成物
および他の通常液状の石油留分燃料組成物に用い
てスクリーン目詰まり防止性や解乳化性を燃料に
付与することができる。
上記燃料組成物は、この発明の清浄・分散剤に
加えて、当該技術分野において公知の他の添加剤
を含んでいてもかまわない。その添加剤として
は、テトラアルキル鉛化合物のようなアンチノツ
ク剤、ハロアルカンのような掃鉛剤、リン酸トリ
アリールのような沈積防止剤、変性剤、染料、セ
タン価向上剤、２，６―ジ―第三ブチル―４―メ
チルフエノールのような酸化防止剤、アルキル化
コハク酸およびその無水物のような防さび剤、細
菌発育防止剤、ガムインヒビター、金属奪活剤、
上部シリンダー潤滑剤等がある。
好ましい燃料組成物においては、燃料および潤
滑剤中でこの発明の縮合生成物および後処理生成
物が他種の無灰分散剤と一緒に用いられる。この
ような無灰分散剤は、好ましくは、モノもしくは
ポリオールと、アシル部分が少なくとも30個の炭
素原子を有する高分子量モノもしくはポリカルボ
ン酸アシル化剤とのエステル類である。このよう
なエステル類は当該技術分野でよく知られてい
る。例えば、仏国特許第1396645号、英国特許第
981850号および同第1055337号、さらには米国特
許第3255108号、同第3311558号、同第3331776
号、この発明の添加剤を上記マンニツヒ縮合生成
物とともに用いる場合は、マンニツヒ縮合生成物
１部につきこの発明の反応生成物10ないし0.1部
の割合で用いられる。
この発明の清浄・分散剤は、これを直接燃料や
潤滑油に加えてもよいし、あるいはこれを、種々
の油または既述の通常液状の燃料のような不活性
の溶剤／希釈剤で希釈して添加剤濃縮物を作つて
もよい。この濃縮物は、一般に、この発明の清
浄・分散剤を20ないし90％含んでおり、また、さ
らに、既述の通常の添加剤、ことに上記無灰分散
剤を上記の割合で含んでいてもかまはない。同第
3346354号、同第3579450号、同第3542680号、同
第3381022号、同第3639242号、同第3697428号、
同第3708522号、また英国特許第1306529号参照。
一般に、この発明の清浄・分散剤と上記無灰分
散剤との重量比は、0.1ないし10.0であり、好ま
しくは、無灰分散剤１部当りこの発明の清浄・分
散剤１ないし約10部である。好ましい重量比は分
散剤１部につきこの発明の清浄・分散剤0.5ない
し2.0部である。さらにこの発明の他の態様にお
いては、この発明の添加剤が、置換フエノール、
アルデヒド、ポリアミンおよび置換ピリジンから
生成されたマンニツヒ縮合生成物と組合わされ
る。このような縮合生成物は、米国特許第
3649659号、同第3558743号、同第3539633号、同
第3704308号および同第3725277号に記載されてい
る。以下に、この発明の組成物および濃縮物の例
を示す。
例 Ａ 8.4psiのリード蒸気圧を有し、ガロン当り鉛
3.2グラムおよびガソリン100万部につき実施例１
(c)の反応生成物120部含有するガソリン。
例 Ｂ 燃料100万部につき実施例２(c)の反応生成物250
部含有するジーゼル燃料油。
例 Ｃ 実施例１(c)の反応生成物0.5％を含有する溶剤
精製ニユートラルSAE10鉱油。
例 Ｄ アジピン酸およびグルタル酸の混合物（モル比
50／50）のC5〜C9ノルマルアルコールエステル
から主としてなり、実施例２(c)の反応生成物を
0.5％含有する合成潤滑剤。
例 Ｅ 例Ｃの鉱油50％と実施例２(c)の生成物50％とか
らなるガソリンブレンド用濃縮物。

Claims (1)

  1. 【特許請求の範囲】 １ (A) 式 （ここで、Ｒは数平均分子量885ないし1040の
    ポリブチル基）で示されるアルフアーヒドロキシ
    アルキルヒドロキシ芳香族化合物もしくはそのポ
    リスルフイドと(B)無水マレイン酸、無水クロロマ
    レイン酸およびアクリル酸よりなる群の中から選
    ばれた酸系反応体とをモル比0.5：１ないし２：
    １の割合で、50℃ないし上記反応体(A)および(B)並
    びに生成物のうちの最低の分解温度未満の温度に
    おいて、0.5ないし約96時間反応させ、その生成
    物を３個ないし７個のアミノ基を有するポリエチ
    レンポリアミンまたはペンタエリスリトールで処
    理して得たことを特徴とする潤滑油または燃料用
    清浄・分散剤。
JP58180982A 1974-04-09 1983-09-30 清浄・分散剤 Granted JPS59135205A (ja)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US45975074A 1974-04-09 1974-04-09
US459750 1983-01-21

Publications (2)

Publication Number Publication Date
JPS59135205A JPS59135205A (ja) 1984-08-03
JPS6231040B2 true JPS6231040B2 (ja) 1987-07-06

Family

ID=23826005

Family Applications (2)

Application Number Title Priority Date Filing Date
JP50042683A Expired JPS6012355B2 (ja) 1974-04-09 1975-04-08 芳香族縮合生成物の製造方法
JP58180982A Granted JPS59135205A (ja) 1974-04-09 1983-09-30 清浄・分散剤

Family Applications Before (1)

Application Number Title Priority Date Filing Date
JP50042683A Expired JPS6012355B2 (ja) 1974-04-09 1975-04-08 芳香族縮合生成物の製造方法

Country Status (9)

Country Link
US (2) US4108784A (ja)
JP (2) JPS6012355B2 (ja)
CA (1) CA1060460A (ja)
ES (1) ES436327A1 (ja)
FR (2) FR2267332B1 (ja)
GB (1) GB1489454A (ja)
IN (1) IN143602B (ja)
IT (1) IT1035195B (ja)
ZA (1) ZA752056B (ja)

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US4278572A (en) * 1980-01-04 1981-07-14 Monsanto Company Phenolic modified olefin polymers
US4723963A (en) * 1984-12-18 1988-02-09 Exxon Research And Engineering Company Fuel having improved cetane
US5336278A (en) * 1993-05-13 1994-08-09 The Lubrizol Corporation Fuel composition containing an aromatic amide detergent
US5441653A (en) * 1994-08-09 1995-08-15 The Lubrizol Corporation Two-stroke cycle engine lubricant and method of using same
US5696060A (en) * 1996-04-15 1997-12-09 The Lubrizol Corporation Acylated nitrogen compounds useful as additives for lubricating oil and fuel compositions
US5696067A (en) * 1996-04-15 1997-12-09 The Lubrizol Corporation Hydroxy-group containing acylated nitrogen compounds useful as additives for lubricating oil and fuel compositions
US5840920A (en) * 1996-08-08 1998-11-24 The Lubrizol Corporation Process for preparing compositions useful as intermediates for preparing lubricating oil and fuel additives
US5779742A (en) * 1996-08-08 1998-07-14 The Lubrizol Corporation Acylated nitrogen compounds useful as additives for lubricating oil and fuel compositions
ES2317787B1 (es) * 2006-12-05 2010-02-12 Laboratorios Invydes De Energia, S.L. Despegador de segmentos y limpiador de inyectores en motores de combustion interna.
JP5789615B2 (ja) * 2009-12-18 2015-10-07 シェブロン・オロナイト・カンパニー・エルエルシー カルボニル−エン官能基化ポリオレフィン
US8920524B2 (en) 2009-12-18 2014-12-30 Chevron Oronite Company Llc Polyisobutenyl alcohols and fuel compositions
DE102019206560A1 (de) * 2019-05-07 2020-11-12 Aktiebolaget Skf Sulfonatzusammensetzung und Schutzmittelzusammensetzung mit der Sulfonatzusammensetzung
CN116925427B (zh) * 2023-07-18 2024-01-19 沧州兴达化工有限责任公司 一种环保防水增塑剂及其制备方法

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Publication number Priority date Publication date Assignee Title
US2370299A (en) * 1941-02-26 1945-02-27 Standard Oil Co California Compounded lubricant
US2370300A (en) * 1937-12-03 1945-02-27 Standard Oil Co California Lubricant
US2363510A (en) * 1942-09-15 1944-11-28 Standard Oil Co California Compounded oil
US2615845A (en) * 1948-08-02 1952-10-28 Standard Oil Dev Co Lubricating oil additives
US3065179A (en) * 1959-04-01 1962-11-20 Exxon Research Engineering Co Metal salts of phenols and low molecular weight acids
US3130160A (en) * 1961-03-01 1964-04-21 Exxon Research Engineering Co Oil compositions containing metal salt of phenol and low molecular weight acid
DE1271877B (de) * 1963-04-23 1968-07-04 Lubrizol Corp Schmieroel
US3385792A (en) * 1965-11-05 1968-05-28 Exxon Research Engineering Co Lubricants containing mixed metal salt of fatty acid and diphenols
US3449236A (en) * 1966-04-27 1969-06-10 Exxon Research Engineering Co Dewaxing aid composition
US4067698A (en) * 1975-08-27 1978-01-10 The Lubrizol Corporation Bridged phenol metal salt-halo carboxylic acid condensate additives for fuels
US4061474A (en) * 1975-08-27 1977-12-06 The Lubrizol Corporation Phenoxide-halo carboxylic acid condensate additives for fuels

Also Published As

Publication number Publication date
FR2279767B1 (ja) 1978-07-28
US4108784A (en) 1978-08-22
CA1060460A (en) 1979-08-14
ZA752056B (en) 1976-11-24
JPS50148320A (ja) 1975-11-27
JPS6012355B2 (ja) 1985-04-01
IN143602B (ja) 1977-12-31
ES436327A1 (es) 1977-04-01
US4163730A (en) 1979-08-07
JPS59135205A (ja) 1984-08-03
GB1489454A (en) 1977-10-19
IT1035195B (it) 1979-10-20
FR2267332B1 (ja) 1980-01-25
FR2279767A1 (fr) 1976-02-20
FR2267332A1 (ja) 1975-11-07

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