Patent GB-965373-A (GB)
Title: Amides containing a substituted phenol group and stabilisation of organic material therewith
IPC: C09K15/24
Filed: 1962-10-26
Abstract: The invention relates to amides of the formula: <FORM:0965373/C1/1> in which A is an alkylene or isoalkylene group, R1 is an alkyl group, R2 is hydrogen or an alkyl group, R3 is hydrogen or an alkyl, alkylphenyl or alkylbenzyl group and R4 is an alkyl, alkylphenyl or alkylbenzyl group. Alternatively, R3 and R4, together with the nitrogen atom, may form a morpholino group.  The amides are obtainable from the corresponding acids or acid halides and amines, and examples are given of the preparation of N-octadecyl- or N-dodecylphenyl- or N-dodecylbenzyl- or N-tert-octyl-3,5-di-tert-butyl-4-hydroxyphenylacetamide, 3,5-di-tert-butyl-4-hydroxyphenylacetomorpholide, N, N-di-2-ethylhexyl or N,N-di-n-dodecyl 3,5-di-tert-butyl-4-hydroxyphenylacetamide and N-octadecyl b -3,5-di-tert-butyl-4-hydroxyphenyl propionamide. A number of other groups which R1, R2, R3 and R4 may represent are also specified. The products are useful as stabilizers for organic materials liable to oxidative degradation and may be used for stabilizing, inter alia, lubricants and aldehydes. Specified lubricants which may be treated are dihexyl azelate, di-(2-ethylhexyl) azelate, di-(3,5,5-trimethylhexyl) glutarate, di-(3,5,5-trimethylpentyl) glutarate, di-(2-ethylhexyl) pimelate, di-(2-ethylhexyl) adipate, diisoaryl adipate, trianyl tricarbollylate, pentaerythritol tetracaproate, dipropylene glycol dipelargonate and 1,5-pentanediol di-(2-ethylhexanoate). Heptaldehyde is specified as a suitable aldehyde.ALSO:As stabilizers for organic materials liable to oxidative degradation, use is made of amides of the formula: <FORM:0965373/C3/1> in which A is an alkylene or isoalkylene group, R1 is an alkyl group, R2 is hydrogen or an alkyl group, R3 is hydrogen or an alkyl, alkylphenyl or alkylbenzyl group and R4 is an alkyl, alkylphenyl or alkylbenzyl group. Alternatively, R3 and R4, together with the nitrogen atom, may form a morpholino group. Examples are given of the preparation of N-octadecyl- or N-dodecylphenyl-or N-dodecylbenzyl- or N-tert.-octyl- 3,5-ditert.-butyl -4- hydroxyphenylacetamide, 3,5-ditert.-butyl -4- hydroxyphenylacetomorpholide, N, N-di-2-ethylhexyl- or N,N-di-n-dodecyl- 3, 5-di-tert.-butyl -4- hydroxyphenylacetamide and N-octadecyl-b -3, 5-di-tert.-butyl -4- hydroxyphenylpropionamide. A number of other groups which R1, R2, R3 and R4 may represent are also specified. The products may be used for stabilizing polyethylene, polypropylene and polystyrene containing co-polymers of butadiene and styrene. The stabilizers are preferably used in association with dilauryl -b - thiodipropionate or other stabilizer of the general formula: <FORM:0965373/C3/2> where n is 1 or 2 and R7 and R8 are alkyl groups. The compositions of the invention may also contain other antioxidants, pour-point depressants, corrosion and rust inhibitors, dispersing agents, demulsifiers, anti-foaming agents, carbon black, vulcanization accelerators, plasticizers, colour and heat stabilizers, ultraviolet absorbers, dyes, pigments and metal chelating agents. Examples are given of the stabilization of polypropylene and of polystyrene containing butadiene-styrene copolymer.ALSO:As stabilizers for organic materials liable to oxidative degradation, use is made of amides of the formula <FORM:0965373/C4-C5/1> in which A is an alkylene or isoalkylene group, R1 is an alkyl group, R2 is hydrogen or an alkyl group, R3 is hydrogen or an alkyl, alkylphenyl or alkylbenzyl group and R4 is an alkyl, alkylphenyl or alkylbenzyl group. Alternatively, R3 and R4, together with the nitrogen atom, may form a morpholino group. Examples are given of the preparation of N-octadecyl- or N-dodecylphenyl-or N-dodecylbenzyl- or N-tert. - octyl - 3,5 - di - tert. - butyl - 4 - hydroxy-phenylacetamide, 3,5 - di - tert. - butyl - 4 - hydroxyphenylacetomorpholide, N,N - di - 2 - ethylhexyl- or N,N-di-n-dodecyl-3,5-di-tert.-butyl - 4 - hydroxyphenylacetamide and N-octadecyl - b  - 3,5 - di - tert. - butyl - 4 - hydroxyphenyl propionamide.  A number of other groups which R1, R2, R3 and R4 may represent are also specified.  The products may be used for stabilizing lubricants, animal and vegetable oils, hydrocarbon fuels (e.g. gasoline, jet fuel, diesel fuel and fuel oil, waxes, resins and cycloolefines. Specified lubricants which may be treated are dihexyl azelate, di-(2-ethylhexyl)-azelate, di - (3,5,5 - trimethylhexyl) glutarate, di - (3,5,5 - trimethylpentyl) glutarate, di - (2 - ethylhexy) pimelate, di - (2 - ethylhexyl) adipate, diisoamyl adipate, triamyl tricarballylate, pentaerythritol tetracaproate, dipropylene glycol dipelargonate and 1,5-pentanediol di-(2-ethylhexanoate). A number of animal and vegetable oils which may be treated are specified. Cyclohexene is specified as a suitable cyclo-olefine.  The stabilizers are preferably used in association with dilauryl-b -thiodipropionate or other stabilizer of the general formula <FORM:0965373/C4-C5/2> where n is 1 or 2 and R7 and R8 are alkyl groups. The compositions of the invention may also contain other antioxidants, pour-point depressants, corrosion and rust inhibitors, dispersing agents, demulsifiers, anti-foaming agents, carbon black, vulcanization accelerators, plasticizers, colour and heat stabilizers, ultraviolet absorbers, dyes, pigments and metal chelating agents. An example is given of the stabilization of a mineral oil.