CN1028873C - 燃料和润滑油的清净、分散和防锈添加剂 - Google Patents
燃料和润滑油的清净、分散和防锈添加剂 Download PDFInfo
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- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 title abstract description 7
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- SBNFWQZLDJGRLK-UHFFFAOYSA-N phenothrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- 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
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/224—Amides; Imides carboxylic acid amides, imides
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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
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/16—Amides; Imides
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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Abstract
一种具有清净、分散和防锈性能的燃料和润滑油的添加剂，基本上由式(I)的链烯基琥珀酸或酸酐的混合物与式(II)的三亚乙基四胺缩合的产物组成：
其中m和n分别代表0或1-10的整数，并且m和n之和为9或10，R是O或(-OH，-OH)，
H2N-(CH2-CH2-NH3)3-H (II)
Description
本发明涉及燃料和润滑油的具有清净、分散和防锈性能的添加剂。
该添加剂主要由式（Ⅰ）的链烯基琥珀酸或酸酐的混合物与式（Ⅱ）的三亚乙基四胺缩合的产物组成，
其中，m和n分别代表0或1-10的整数，并且使得m和n之和为9或10，
O或（-OH，-OH），
H2N-（CH2-CH2-NH）3-H （Ⅱ）
专利文献介绍了几种链烯基琥珀酰亚胺化合物及这些化合物在燃料和润滑剂中作分散剂和清净添加剂的应用，这是公知的。列举下列美国和欧洲专利做为例子：US-A-3，287，271、US-A-3，172，892、US-A-4，048，080、US-A-3，216，936、US-A-4，338，205、US-A-3，401，118、US-A-3，717，446，US-A-3，131，150、US-A-4，548，724、US-A-3，799，877、EP-A-20，037和EP-A-8，953。
不过，改进这些配方的性能仍是这方面工作的目的，例如改进的途径是找到一些活性更高的化合物或在特殊的应力条件下也能发挥其活性的化合物，或具有一种以上性能的化合物，或找到能以较低的成本生产的化合物或能使要制备的成品更稳定的化合物等等。
现在人们已经发现由式（Ⅰ）的链烯基琥珀酸或酸酐的混合物与三亚乙基四胺缩合所得的产物具有优异的清净、分散特性和相当好的防锈活性，以致当以合适的浓度将这些添加剂加到液体燃料或润滑剂组合物中时，它确保悬浮液中存在的固体颗粒完全分散，例如就燃料来说避免在汽化器和喷射器上形成沉积物，同时完全避免与这些燃料或润滑剂接触的金属部件生锈。
其中，m和n分别代表0或1～10的整数，并且使得m和n的和是9或10，
O或（-OH，-OH）。
特别是人们发现，如果链烯基琥珀酸或酸酐（Ⅰ）的混合物是由马来酸酐与双键沿整个脂肪链统计学分布的13和/或14个碳原子的直链单烯的混合物缩合而得到的，则所得的效果很好。
这种类型的混合物例如是采用常规的方法由相应的正构链烷烃催化脱氢而得到的混合物。
在这种情况下，在合适的条件下操作，可以得到在其中双键沿整个链（即使最好在它内部）统计学分布的单烯混合物。
为了制备本发明的添加剂，使链烯基琥珀酸或酸酐（Ⅰ）的混合物与三亚乙基四胺（Ⅱ）以（Ⅰ）/（Ⅱ）摩尔比一般为2/1-1/1的比例进行反应。得到的产物大体上是单酰亚胺和双酰亚胺以及酰胺的多元混合物，这取决于两种缩合成分的配比。
根据本发明的优选的情况，若所用的（Ⅰ）/（Ⅱ）比例接近2，绝大部分产物是通式（Ⅲ）的双琥珀酰亚胺混合物，
其中m和n的定义同前，m′和n′的定义与m和n相同，不过它们是独立的。对于特定的m和n值，由下面的图式可以说明由马来酸酐和C13和/或C14单烯混合物制备链烯基琥珀酸酐（Ⅰ）：
一般采用烯烃/马来酸酐的比例为3/1～1/1，最好1.5/1来进行这个反应。这个反应的温度在140～270℃变化，但最好为170～250℃，在这个温度范围内收率最高。
除去未反应的起始物料后，得到的链烯基琥珀酸酐（Ⅰ）的混合物可以（Ⅰ）/（Ⅱ）的摩尔比为2/1～1/1的比例直接与三亚乙基四胺（Ⅱ）接触，一般在温度为120～250℃最好为150～200℃下进行缩合反应。缩合反应一般在1～6小时内完成，这取决于所选择的温度。为了使反应平衡向产物方向移动，要从反应介质中除去缩合反应时脱出的水。为此，在与水生成容易蒸馏的共沸物的有机惰性溶剂如甲苯或二甲苯存在下进行反应是便利的。
以这种方法得到的产物不需特殊的处理，实际上产物本身可以用
做液体燃料和润滑剂的添加剂。
根据本发明，这种产物以一定量加到液体燃料和润滑剂中，所用量足以提供所需的清净和分散活性并足以抑制在与含添加剂的燃料和润滑油接触的金属零件上生锈。
一般有效量是0.001～5%（重），最好0.01～3%（重）。
添加剂本身可直接加到燃料和润滑剂中，或者采用含有25～95%（重）、最好50～70%（重）的溶于溶剂-稀释剂的添加剂的浓缩物可使添加变得更为方便，本发明的优选情况下的溶剂-稀释剂可以是要把添加剂加入其中的实际的燃料和润滑油，例如汽油、柴油、煤油和矿物油等。含本发明的添加剂的浓缩物和燃料或润滑剂都可以含有其它辅助的添加剂，对于燃料如破乳化剂、消泡剂等，对于润滑剂如抗磨剂和粘度改进剂等。该浓缩物和成品燃料或润滑剂也可以含有足以提供所需效果的量的其它清净剂、分散剂和/或防锈剂。
下面的非限制性的实施例更详细地说明本发明的添加剂，它的制备方法以及用来评价该添加剂的分散、清净和防锈能力的一些试验。
实施例1
该新型添加剂的制备
将平均分子量187并含58%十三碳烯和40%十四碳烯的正构烯烃混合物（1069.79克）、马来酸酐（373.76克，3.81摩尔）和合成时做为阻聚剂的少量吩噻嗪（1.5克）加入装有机械搅拌器、温度计和回流冷凝器的烧瓶中。
在氮气氛、搅拌下将混合物加热到180℃，缩合马来酸酐和烯烃蒸气。反应进行时，温度逐渐上升至220℃，在这个温度下保持
13小时。在220℃下蒸馏回收过量的烯烃（413.65克）和未反应的马来酸酐（29.91克），同时反应烧瓶内逐渐减压从常压减到约10mmHg（1330Pa）。用这种方法得到的产物（1000克，收率92%）具有中和值200毫克KOH/g（用ASTM D 664方法滴定），相当于平均分子量为280.5。将一部分所得产物（500克，1.78摩尔）和聚硅氧烷消泡剂（10毫克）加入装有机械搅拌器、温度计和冷凝器的烧瓶中。搅拌下将混合物加热到130℃，然后用滴液漏斗在1小时之内将纯度为91.4%的三亚乙基四胺（138.6克，0.87摩尔）逐渐加入。在加料时温度自然上升到180℃。
加料结束后，反应混合物保持在160℃下2小时，蒸馏除去反应时生成的水。通过将反应烧瓶中的压力从常压逐渐减低到约10mmHg（1330Pa）并在150℃下保持温度30分钟来完全除去水。
得到的产物在100℃粘度为4.96cst，凝固点-9℃，氮含量8%，用ASTM D2896方法测定的碱滴定率为157mg KOH/g。
实施例2
防锈能力的评定
a）在燃料中
在装有维持在60℃的300克燃料（柴油或汽油）和30克蒸馏水的混合物容器中使钢杆旋转24小时（ASTM D665/A试验）。然后评价钢杆上生成的锈。
在燃料没有添加剂的情况下，24小时后钢杆完全被锈覆盖。
相反，如在燃料中加入50ppm的实施例1的化合物，钢杆只有很少几处被锈覆盖，而加入100ppm实施例1的添加剂，则钢杆完全不生锈。
b）在车用机油中
采用平行试验，用不含实施例1的添加剂的对比润滑剂和含0.15%实施例1的产物的相同润滑剂作为润滑剂，用上述的ASTM D665/A试验和根据ASTM STP 315方法使用V-8Oldsmobile发动机通过系列ⅡD发动机台架试验运转32小时两种方法来评价车用机油情况下的防锈性能。对比润滑剂配方为含1.3%二硫代磷酸锌、4.5%无灰分散剂和1.5%由过碱性磺酸钙（12%（重）的钙）组成的清净剂，并且100℃时的粘度为12.5cst的矿物油。若试验结束时发动机元件的评价（评分满分为10）评分超过8.5，则认为该发动机实验结果是相当肯定的。
在ASTM D665/A试验中，不含防锈添加剂的对比润滑剂使钢杆50%被锈覆盖，而在系列ⅡD发动机试验中，其平均锈蚀评分为7.5。相反，含有0.15%实施例1的添加剂的润滑剂在ASTM D665/A试验中使钢杆完全无锈，在发动机试验中平均评分为8.7。
实施例3
清净能力的评定
a）在柴油中
用没有清净剂的工业柴油做对比，并且用加了100ppm的实施例1的产物的同样柴油，通过发动机喷射器的清净试验来评价清净
能力。具体地说，使用装有DN OSD 252 Bosch喷射器的增压Pesgeot XD2S柴油发动机，台架运转20小时。
在试验前后，测定不同针上升高度（0.1和0.3mm）的情况下喷射器的物料通过量，这些测定用来计算由于形成沉积而引起的物料通过量减少的百分数。
在没有添加剂的工业柴油的情况下，物料通过量平均减少为76.5%，用含100ppm实施例1的产物的柴油，则该平均减少为60.5%，因而，与没有添加剂的柴油比较，相当于在喷射器的沉积减少21%。
b）在汽油中。
用工业汽油做对比，用加入100ppm实施例1产物的同样的汽油，通过汽化器的发动机清净试验来评定清净能力。具体地说，使用Renault R5汽油发动机，按照CECF-O3-T-81台架运转。用常规1-10评定等级进行评定，10相当于汽化器完全清洁。
在这个发动机试验中没有添加剂的汽油评分为3.7，而加入100ppm实施例1产物的汽油评分为8.8。
实施例4
分散能力的评定。
通常柴油含有不定量的悬浮碳粒。在柴油发动机中，其中过滤系统装在燃料供给回路，这些沉积物的积聚使燃料通过量逐渐下降直至过滤器完全堵塞。
使用模拟柴油发动机中使用的过滤系统，在相同的条件下，用相同体积的含100ppm实施例1的产物的工业柴油和没有添加剂的
相同的柴油，测定过滤所需的时间而评定实施例1的产品对这些沉积物的增溶/分散作用。
在第一种情况下过滤时间12分钟，而在第二种情况下过滤时间26分钟。
Claims (5)
1、制备具有清净、分散和防锈性能的、用于马达液体燃料和润滑油中的添加剂的方法，所说添加剂主要包含由式Ⅰ的链烯基琥珀酸的或其酸酐的混合物与式(Ⅱ)的三亚乙基四胺缩合而成的缩合产物，
其中，m和n别代表0或一个1-10的整数，并且m和n之和为9或10，R是O或(-OH，-OH)，
H2N-(CH2-CH2-NH)3-H (Ⅱ)
其特征在于，在150-200℃内直接加热(Ⅰ)和(Ⅱ)的混合物而进行该缩合反应。
2、根据权利要求1的方法，其特征在于，链烯基琥珀酸或酸酐（Ⅰ）的混合物与三亚乙基四胺（Ⅱ）的摩尔比值是3-1。
3、根据权利要求2的方法，其特征在于，所说的摩尔比值为2。
4、根据权利要求1的方法，其特征在于，式（Ⅰ）中链烯基是从其链中有13和/或14个碳原子的直链单烯的混合物中产生的，在它们的链中具有按统计学分布的双键。
5、根据权利要求4的方法，其特征在于，起始的链烯基琥珀酸酐（Ⅰ）是由马来酸酐与其中有13和/或14个碳原子、由相应的正构烷烃催化脱氢而提到的直链单烯混合物反应而制得的。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT8920258A IT1229659B (it) | 1989-04-21 | 1989-04-21 | Additivo detergente, disperdente ed anti ruggine per combustibili ed oli lubrificanti. |
| IT20258A/89 | 1989-04-21 |
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| Publication Number | Publication Date |
|---|---|
| CN1047106A CN1047106A (zh) | 1990-11-21 |
| CN1028873C true CN1028873C (zh) | 1995-06-14 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN90103623A Expired - Lifetime CN1028873C (zh) | 1989-04-21 | 1990-04-21 | 燃料和润滑油的清净、分散和防锈添加剂 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5156654A (zh) |
| EP (1) | EP0393769B2 (zh) |
| JP (1) | JP2864146B2 (zh) |
| KR (1) | KR930011072B1 (zh) |
| CN (1) | CN1028873C (zh) |
| AT (1) | ATE103631T1 (zh) |
| AU (1) | AU621217B2 (zh) |
| BR (1) | BR9001849A (zh) |
| DE (1) | DE69007664T3 (zh) |
| DK (1) | DK0393769T3 (zh) |
| ES (1) | ES2062294T5 (zh) |
| GR (1) | GR3025397T3 (zh) |
| HU (1) | HU208992B (zh) |
| IT (1) | IT1229659B (zh) |
| MX (1) | MX171561B (zh) |
| PL (1) | PL163729B1 (zh) |
| PT (1) | PT93835B (zh) |
| RU (1) | RU1838387C (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0613886A1 (en) * | 1993-03-01 | 1994-09-07 | Shell Internationale Researchmaatschappij B.V. | Cyclopentadiene derivatives as dispersants for lubricating vils and for fuels |
| JPH0711274A (ja) * | 1993-03-01 | 1995-01-13 | Shell Internatl Res Maatschappij Bv | 添加剤濃厚液 |
| US5520831A (en) * | 1993-12-20 | 1996-05-28 | Exxon Chemical Patents Inc. | Increasing the friction durability of power transmission fluids through the use of oil soluble competing additives |
| EP0736082B1 (en) * | 1993-12-20 | 2003-02-19 | Infineum USA L.P. | Increasing the friction durability of power transmission fluids through the use of oil soluble competing additives |
| WO1995017489A1 (en) * | 1993-12-20 | 1995-06-29 | Exxon Chemical Patents Inc. | Oil soluble friction increasing additives for power transmission fluids |
| US5516444A (en) * | 1994-10-13 | 1996-05-14 | Exxon Chemical Patents Inc | Synergistic combinations for use in functional fluid compositions |
| JP3719266B2 (ja) * | 1995-10-18 | 2005-11-24 | エクソンモービル・ケミカル・パテンツ・インク | 摩擦耐久性が改良された潤滑油 |
| US5750476A (en) * | 1995-10-18 | 1998-05-12 | Exxon Chemical Patents Inc. | Power transmitting fluids with improved anti-shudder durability |
| JPH09255973A (ja) * | 1996-03-25 | 1997-09-30 | Oronaito Japan Kk | 軽油添加剤及び軽油組成物 |
| TW457295B (en) * | 1996-10-29 | 2001-10-01 | Idemitsu Kosan Co | A lubricating oil composition for diesel engines |
| US5840663A (en) * | 1996-12-18 | 1998-11-24 | Exxon Chemical Patents Inc. | Power transmitting fluids improved anti-shudder durability |
| FR2792646B1 (fr) * | 1999-04-26 | 2001-07-27 | Elf Antar France | Composition d'additifs multifonctionnels d'operabilite a froid des distillats moyens |
| CN111608761B (zh) * | 2020-06-02 | 2022-06-07 | 四川省天域航通科技有限公司 | 一种大型货运无人机润油系统 |
| CN117924917A (zh) * | 2023-12-25 | 2024-04-26 | 亚培烯科技(上海)有限公司 | 增韧尼龙组合物及其制备和用途 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US2490744A (en) | 1947-02-08 | 1949-12-06 | Socony Vacuum Oil Co Inc | Antirust agent |
| US2982633A (en) * | 1959-01-16 | 1961-05-02 | Socony Mobil Oil Co Inc | N-substituted alkenyl succinamic acid deicer |
| GB1053340A (zh) * | 1963-10-14 | 1900-01-01 | ||
| US3272746A (en) | 1965-11-22 | 1966-09-13 | Lubrizol Corp | Lubricating composition containing an acylated nitrogen compound |
| DE1794133B2 (de) * | 1968-09-13 | 1975-09-25 | The Lubrizol Corp., Cleveland, Ohio (V.St.A.). | Schmierole |
| BE755036A (fr) * | 1969-08-19 | 1971-02-19 | British Petroleum Co | N-amino-alkenyl succinimides, leur preparation et leur utilisation |
| US4614522A (en) * | 1985-04-12 | 1986-09-30 | Chevron Research Company | Fuel compositions containing modified succinimides (VI) |
| EP0299119A1 (en) * | 1986-06-23 | 1989-01-18 | Petrolite Corporation | Corrosion inhibited oxgenated fuel systems |
| US4863487A (en) * | 1987-04-29 | 1989-09-05 | Nalco Chemical Company | Hydrocarbon fuel detergent |
-
1989
- 1989-04-21 IT IT8920258A patent/IT1229659B/it active
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1990
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- 1990-04-13 AT AT90200917T patent/ATE103631T1/de not_active IP Right Cessation
- 1990-04-13 DE DE69007664T patent/DE69007664T3/de not_active Expired - Lifetime
- 1990-04-17 AU AU53610/90A patent/AU621217B2/en not_active Expired
- 1990-04-19 KR KR1019900005455A patent/KR930011072B1/ko not_active IP Right Cessation
- 1990-04-20 HU HU902514A patent/HU208992B/hu unknown
- 1990-04-20 MX MX020401A patent/MX171561B/es unknown
- 1990-04-20 JP JP2103268A patent/JP2864146B2/ja not_active Expired - Lifetime
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- 1990-04-20 PL PL90284861A patent/PL163729B1/pl unknown
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- 1990-04-20 RU SU904743674A patent/RU1838387C/ru active
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Also Published As
| Publication number | Publication date |
|---|---|
| EP0393769B1 (en) | 1994-03-30 |
| DE69007664D1 (de) | 1994-05-05 |
| ES2062294T3 (es) | 1994-12-16 |
| PL163729B1 (pl) | 1994-04-29 |
| JP2864146B2 (ja) | 1999-03-03 |
| KR930011072B1 (ko) | 1993-11-20 |
| DE69007664T3 (de) | 1998-03-12 |
| RU1838387C (ru) | 1993-08-30 |
| DE69007664T2 (de) | 1994-07-14 |
| BR9001849A (pt) | 1991-06-18 |
| US5156654A (en) | 1992-10-20 |
| EP0393769A1 (en) | 1990-10-24 |
| HU208992B (en) | 1994-02-28 |
| KR900016436A (ko) | 1990-11-13 |
| PT93835B (pt) | 1998-06-30 |
| MX171561B (es) | 1993-11-05 |
| GR3025397T3 (en) | 1998-02-27 |
| HUT54200A (en) | 1991-01-28 |
| AU5361090A (en) | 1990-10-25 |
| AU621217B2 (en) | 1992-03-05 |
| IT1229659B (it) | 1991-09-06 |
| DK0393769T3 (da) | 1994-06-27 |
| EP0393769B2 (en) | 1997-11-12 |
| IT8920258A0 (it) | 1989-04-21 |
| ATE103631T1 (de) | 1994-04-15 |
| HU902514D0 (en) | 1990-08-28 |
| PT93835A (pt) | 1990-11-20 |
| JPH02300292A (ja) | 1990-12-12 |
| ES2062294T5 (es) | 1998-03-01 |
| CN1047106A (zh) | 1990-11-21 |
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