Nitrogen-containing compounds

Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Mixing of two or more solid polymers; mixing of solid...

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525350, 5253593, 5253595, 525379, 525380, 525381, C08F 830

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active

056840934

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

The invention relates to an improved method for the manufacture of nitrogen-containing compounds. More particularly, the invention relates to an improved method for the manufacture of functionalised polymers suitable for use as lubricating or fuel oil additives or as intermediates suitable for use in the manufacture of such additives, to functionalised polymers obtainable by the said method and to their use. The invention also relates to the manufacture of dihydrooxazines.


BACKGROUND OF THE INVENTION

For the past 30 to 50 years, lubricating oils used as crankcase lubricants in internal combustion engines in automobiles and trucks have normally contained ashless dispersants. Dispersants maintain oil-insoluble substances, resulting from oxidation during use, in suspension in the fluid, thus preventing sludge flocculation and precipitation or deposition on metal parts. So-called ashless dispersants are organic materials which form substantially no ash on combustion, in contrast to metal-containing (and thus ash-forming) detergent. Examples of ashless disperants are the reaction products of amines and/or alcohols, including amino-alcohols, with hydrocarbyl-substituted mono- or dicarboxylic acids, long chain aliphatic hydrocarbons having one or more polyamine molecules attached directly thereto, and Mannich condensation products containing a long chain hydrocarbyl group, far example, as a substituent of a phenol. Crankcase lubricants may in addition, or alternatively, contain viscosity index modifier dispersants (sometimes called multifunctional viscosity modifiers), which have both viscosity index-modifying and dispersant properties. Ashless dispersants and/or viscosity index modifier dispersants are frequently also used in other lubricating oil compositions, an ashless dispersants may also be used in fuels.
One advantageous class of the ashless dispersants mentioned above comprises the hydrocarbyl-substituted dicarboxylic acids or anhydrides and derivatives thereof, the hydrocarbyl substituents of the said acids or anhydrides containing, for example, from 50 to 400 carbon atoms. That class includes especially succinic acid or anhydride having a side chain derived from polyisobutene, the last-mentioned compounds commonly being known as PIBSAs, and their reaction products with alcohols and/or amines, for example, polyamines (PAMs). A previously known process for the manufacture of hydrocarbyl-substituted dicarboxylic acids or anhydrides involves a chlorination step, in which a polyalkene is reacted with chlorine, and an "acidification" step, in which the chlorinated polyalkene is reacted with maleic anhydride. The chlorination and acidification steps may be carried out either simultaneously or sequentially.
The polymer functionalisation step in the above-mentioned process involves the use of chlorine gas, and requires suitable precautions to be taken in handling and disposal.
Other methods known in the art for functionalizing polyolefins involve hydroformylation, iminomethylation, reductive amination and alkylation, each of which require catalysts which necessitate handling precautions.
Amidoalkylation of olefinically-unsaturated compounds has been described in relation to non-polymeric olefins in U.S. Pat. No. 3,190,882, GB-A-1 231 409, GB-A-1 147 888, Perchec et al (Revue de L'Institut Francais du Petrole, Vol. 41, No. 2, 275 to 295) and Zaugg (Synthesis, 1970, 49 to 73), but these documents do not describe the amidoalkylation of olefinically unsaturated polymers to form products which may be useful as a dispersant for lubricants or fuels.


SUMMARY OF THE INVENTION

The present invention provides a method of preparing a functionalised polymer, particularly a functionalised polymer suitable for use as a dispersant or as an intermediate for use in the preparation of a dispersant, comprising reacting, in the presence of an acid catalyst, from 350 to 100,000 and respectively, is substituted by a group --CHX R.sup.2 in which X is a group that, under the reaction conditions, acts as a le

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Synthesis International Journal of Methods in Synthetic Organic Chemistry No. 2 (Feb. 1979).

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