GB1199422A - Nitrogen-Containing Detergent Materials and Compositions containing the same - Google Patents

Nitrogen-Containing Detergent Materials and Compositions containing the same

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Publication number
GB1199422A
GB1199422A GB53703/67A GB5370367A GB1199422A GB 1199422 A GB1199422 A GB 1199422A GB 53703/67 A GB53703/67 A GB 53703/67A GB 5370367 A GB5370367 A GB 5370367A GB 1199422 A GB1199422 A GB 1199422A
Authority
GB
United Kingdom
Prior art keywords
acid
polybutenyl
hydrogen
give
products
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
GB53703/67A
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.)
Monsanto Co
Original Assignee
Monsanto Co
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 Monsanto Co filed Critical Monsanto Co
Publication of GB1199422A publication Critical patent/GB1199422A/en
Expired legal-status Critical Current

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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D291/00Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms
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    • C07D291/06Six-membered rings
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  • Organic Chemistry (AREA)
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  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

1,199,422. Olefin polymer derivative. MONSANTO CO. 24 Nov., 1967 [25 Nov., 1966], No. 53703/67. Heading C3P. [Also in Divisions C4-C5] Compounds of formula where R and R<SP>1</SP> are each hydrogen, hydrocarbyl or substituted hydrocarbyl, at least one of which has at least 40 carbon atoms and having together at least 50 carbon atoms; R<SP>2</SP> and R<SP>3</SP> are hydrogen, hydrocarbyl or substituted hydrocarbyl having 1 to 30 carbon atoms; provided that when any of R, R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> are substituted the weight of the substituents deos not exceed 15% of the total weight of the groups; R<SP>4</SP> is hydrogen, optionally substituted C 1-10 hydrocarbyl or an optionally substituted heterocyclic group having 4 to 10 carbon atoms and 1 to 4 oxygen, nitrogen and/or sulphur atoms; may be prepared by reacting an olefin polymer of formula R-CR<SP>2</SP>=CR<SP>3</SP>-R<SP>1</SP> with a sulphur trioxide yielding material and a nitrile of formula R<SP>4</SP>CN. The products may be hydrolysed and optionally halogenated to give compounds of formula where R 5 is hydrogen or CO-R<SP>4</SP> and X is halogen or OM where M is hydrogen or a metal or ammonium cation; and the compounds and hydrolysis products may be further reacted with amines and optionally with an oxide, halide, acid or acid ester of boron or with a zinc or nickel salt to give further products, all of which compounds and products may be used as detergent additives in lubricating oils. Preferred polymers are of propylene and butene, but many others including copolymers of olefins with butadiene, isoprene, piperylene, chloroprene, 1,3-hexadiene, styrene and substituted styrenes are specified. The sulphur trioxide yielding substance may be sulphur trioxide, sulphuric acid, chlorosulphonic acid or a complex of sulphur trioxide with pyridine, dioxane, thioxane or an alkyl phosphate. Many other reactants are listed and examples describe the reaction of acetonitrile and sulphur trioxide with (1, 3 and 4) polybutene, (2) polypropene and (5) polyisobutene; the hydrolysis of (5) with sodium hydroxide to give sodium 2- ethylidene amino-1-polyisobutenyl sulphonate, and of 4-polybutenyl-4,6-dimethyl-2-dioxo-1,2, 5-oxathiazine with ammonium hydroxide to give ammonium 2-ethylidene amino-1-polybutenyl sulphonate and with sodium hydroxide and subsequently hydrochloric acid to give 2- acetamido-1-polybutenyl sulphonic acid; the reaction of (5) with zinc acetate, nickel acetate, calcium oxide or excess calcium oxide and carbon dioxide; and the reaction of 4-polybutenyl - 4,6 - dimethyl - 2 - dioxo - 1,2,5 - oxathiazine with (14) N,N-dimethylaminopropylamine, (15) 1- (2-aminoethyl)-2-propylimidazoline, (16 and 28-31) diethylene triamine, (17) ethylenediamine, (18) tetraethylene pentamine, (19) pentaethylene hexamine, (20) thiourea, (21) urea, (22) diethanolamine, (23) 1-(5-amino- 3-azapentyl) succinimide, (24) 1-(5-amino-3- azapentyl) maleimide, (25) 1-(5-amino-3-azapentyl)-3-polybutenyl succinimide, and (26) 1- (2 - aminoethyl) - 2 - methyl imidazoline, and the further reaction of products (29) with boric acid, (30) with zinc sulphate and (31) with zinc acetate.
GB53703/67A 1966-11-25 1967-11-24 Nitrogen-Containing Detergent Materials and Compositions containing the same Expired GB1199422A (en)

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US59683466A 1966-11-25 1966-11-25

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006132964A3 (en) * 2005-06-03 2007-04-26 Exxonmobil Res & Eng Co Ashless detergents and formulated lubricating oil contraining same
US7820600B2 (en) 2005-06-03 2010-10-26 Exxonmobil Research And Engineering Company Lubricant and method for improving air release using ashless detergents

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006132964A3 (en) * 2005-06-03 2007-04-26 Exxonmobil Res & Eng Co Ashless detergents and formulated lubricating oil contraining same
US7820600B2 (en) 2005-06-03 2010-10-26 Exxonmobil Research And Engineering Company Lubricant and method for improving air release using ashless detergents
US7851418B2 (en) 2005-06-03 2010-12-14 Exxonmobil Research And Engineering Company Ashless detergents and formulated lubricating oil containing same

Also Published As

Publication number Publication date
DE1745150A1 (en) 1971-07-29
SE356054B (en) 1973-05-14

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PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees