Patent GB-493442-A (GB)
Title: Process for the manufacture of valuable condensation products
IPC: C08G73/00
Filed: 1937-04-01
Abstract: Monomolecular addition products stated to have emulsifying properties are obtained by treating anhydrides of organic di- or polycarboxylic acids which contain two carboxyl groups on neighbouring carbon atoms with tertiary amino compounds which contain a hydroxy group or a primary or secondary amino group.  In examples: (1) maleic anhydride is treated with N-b -hydroxyethylpiperidine and b  - N - di - n - butylaminoethyl alcohol; (2) phthalic anhydride is treated with hydroxyethylmorpholine and triethanolamine; (3) isononenylsuccenic acid anhydride is treated with hydroxyethylmorpholine and b -N-diethylaminoethyl alcohol; (4) triethanolamine is treated with a -phenylethylsuccinic anhydride and an anhydride obtained from maleic anhydride and a mixture of isododecylene up to isoocta decylene; (5) an anhydride obtained from maleic anhydride and di-or tri-isopropylbenzene is treated with b -N-diethylaminoethylalcohol and with triethanolamine. Anhydrides obtainable by mixed polymerization of maleic anhydride with unsaturated compounds such as acrylic acid esters, vinylhalogenides, vinyl esters or ethers and styrene and specified as well as the following tertiary amines - diaralkylaminoethylalcohols, N - dialkylaminopropanols, tropine, quinine, N - N-diethylethylenediamine and N - N - N1 - triethylethylenediamine.  The products may be used in association with substances giving off oxygen or sodium carbonate.  Samples have been furnished under Sect. 2 (5) of products obtained from isononenylsuccinic anhydride and N - N-dimethylpropylenediamine and from iso-octyldecenylsuccinic anhydride and N-methyl-N1 - N1-diethyl ethylenediamine.ALSO:Monomolecular addition products stated to have wetting and emulsifying properties are obtained by treating anhydrides of organic di-or poly-carboxylic acids which contain two carboxyl groups on neighbouring carbon atoms with tertiary amino compounds which contain a hydroxy group or a primary or secondary amino group.  The temperature is adjusted so that water is not split off, the anhydride group then forms only one ester or amide group and also one carboxylic group.  The latter may form a quaternary ammonium salt with the tertiary amino group or may be neutralized with alkali. In examples: (1) maleic anhydride is treated with N-b -hydroxyethylpiperidine and b -N-di-n-butylaminoethyl alcohol; (2) phthalic anhydride is treated with hydroxyethylmorpholine and triethanolamine; (3) isononenylsuccinic acid anhydride is treated with hydroxyethylmorpholine and b -N-diethylaminoethylalcohol; (4) triethanolamine is treated with a -phenylethylsuccinicanhydride and an anhydride obtained from maleic anhydride and a mixture of isododecylene up to isooctadecylene; (5) an anhydride obtained from maleic anhydride and di- or tri-isopropylbenzene (cf. Specification 441,016) is treated with b -N-diethylaminoethylalcohol and with triethanolamine.  Anhydrides obtainable by the addition of maleic anhydride to tetrahydronaphthalene or propyl naphthalene or by mixed polymerization of maleic anhydride with unsaturated compounds such as acrylic acid esters, vinylhalogenides, vinylesters or ethers and styrene are specified starting materials as well as the following tertiary amines: diaralkylaminoethylalcohols, N-dialkylaminopropanols, tropine, quinine, N : N-diethylethylenediamine and N : N : N1-triethylethylenediamine.  The addition products may be used in association with substances giving off oxygen or sodium carbonate.  Samples have been furnished under Sect. 2 (5) of products obtained from isononenylsuccinic anhydride and N : N-dimethylpropylenediamine-(1 : 3) and from isooctadecenylsuccinic anhydride and N-methyl-N1 : N1-diethylethylenediamine.  According to the Provisional Specification the di- and poly-carboxylic acids may be used instead of the anhydrides.