Patent GB-977587-A (GB)
Title: Method of stabilization with a substituted triazine and compositions stabilized therey
IPC: C10L1/24
Filed: 1961-03-29
Abstract: Aliphatic aldehydes (e.g. heptaldehyde) or aliphatic ester lubricants (e.g. 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, diisoamyl adipate, trimethyl tricarballylate, pentaerythritol tetracaproate, dipropylene glycol dipelargonate and 1,5-pentanediol di-(2-ethylhexanoate)) are stabilized by incorporating therein (with or without other additives) a compound of the general formula <FORM:0977587/C1/1> wherein X and Y each independently represent an alkyl, cycloalkyl, phenyl, alkylphenyl, alkylhydroxyphenyl, alkylhydroxybenzyl, cyanoalkyl, alkylmercaptoalkyl, alkoxycarbonylalkyl or alkoxycarbonylaryl group, Z represents a hydroxyphenyl, alkylhydroxyphenyl, phenylhydroxyphenyl or alkylhydroxybenzyl group, X, Y, and Z being bound to the ring carbon atoms by way or <FORM:0977587/C1/2> alkyl) or <FORM:0977587/C1/3> benzyl, and wherein also if Y is alkylhydroxyphenyl linked by -NH- or alkyl linked by -S-, and Z is alkylhydroxyphenyl linked by -NH-, then X may also represent a chlorine atom, and if X is alkylhydroxyphenyl linked by -NH-, then Y and Z may both represent chlorine atoms, whilst if both X and Y are alkyl groups linked in the stated manner, then Z may represent an alkylhydroxyphenyl group linked by <FORM:0977587/C1/4> alkanoyl.  Substituted triazines.-Most of the compounds of the general formula above, other than those containing an <FORM:0977587/C1/5> alkanoyl linkage, are obtainable as intermediates or final products in the processes set out in Specification 977,589. Similarly prepared, but outside the scope of Specification 977,589 are 6-(p-hydroxyanilino)-2, 4-bis-(phenylthio)-1, 3, 5-triazine, 6-(o-, m- and p-hydroxyanilino)-2,4-bis-(n-octylthio)-1,3,5-triazine, 6-(2-hydroxy-5-phenylanilino)-2, 4-bis-(n-octylthio)-1, 3, 5-triazine, 6-(p-hydroxy-N-methylanilino)-2, 4-bis-(n-octylthio)-1, 3, 5-triazine and 6-(p-hydroxyphenoxy)-2, 4-bis-(n-octylthio)-1, 3, 5-triazine.  The <FORM:0977587/C1/6> alkanoyl compounds are prepared by acylation of the corresponding -NH- compounds.  When the final product is to contain also one or more -NH- linkages, the acylation is performed on a compound of the general formula <FORM:0977587/C1/7> (wherein R represents an alkylhydroxyphenylamino group), whereafter the two chlorine atoms are replaced by the other desired substituents.ALSO:Polypropylene and polyethylene, which are of high, medium or low density; polystyrene and copolymers of styrene with copolymerizable monomers, e.g. high impact polystyrene containing copolymers of butadiene and styrene, are stabilized by incorporating therein (with or without other additives) a compound of the general formula <FORM:0977587/C3/1> wherein X and Y each independently represent an alkyl, cycloalkyl, phenyl, alkylphenyl, alkylhydroxyphenyl, alkylhydroxybenzyl, cyanoalkyl, alkylmercaptoalkyl, alkoxycarbonyl alkyl or alkoxycarbonylaryl group, Z represents a hydroxyphenyl, alkylhydroxyphenyl, phenylhydroxyphenyl or alkylhydroxybenzyl group, X, Y and Z being bound to the ring carbon atoms by way of -S-, -O-, -NH-, <FORM:0977587/C3/2> (C1- 6 alkyl) or <FORM:0977587/C3/3> benzyl, and wherein also if Y is alkylhydroxyphenyl linked by -NH- or alkyl linked by -S- and X is alkylhydroxyphenyl linked by -NH-, then X may also represent a chlorine atom, and if X is alkylhydroxyphenyl linked by -NH-, then Y and Z may both represent chlorine atoms, whilst if both X and Y are alkyl groups linked in the stated manner, then Z may represent an alkylhydroxyphenyl group linked by <FORM:0977587/C3/4> alkanoyl. In an example, unstabilized polypropylene powder, low pressure polyethylene and high impact polystyrene are stabilized with 6-(4-hydroxy-3, 5-di-t-butylanilino)-2, 4-bis-(n-octylthio)-1, 3, 5-triazine Specification 977,589 is referred to.ALSO:Fats and oils of animal and vegetable origin including linseed oil, menhaden oil, cod liver oil, castor oil, olive oil, rapeseed oil, coconut oil, palm oil, sesame oil, peanut oil, cottonseed oil, fat, lard and beef tallow; hydrocarbons both saturated and unsaturated, for example, petrol, natural or synthetic, jet fuel, diesel loil, mineral oil and fuel oil; aliphatic ester lubricants (of various types, many of which are specified), and hydrocarbon waxes, are stabilized by incorporating (with or without other additives) a compound of the general formula <FORM:0977587/C4-C5/1> wherein X and Y each independently represent an alkyl, cycloalkyl, phenyl, alkyl phenyl, alkylhydroxyphenyl, alkylhydroxybenzyl, cyanoalkyl, alkylmercaptoalkyl, alkoxycarbonylalkyl or alkoxycarbonylaryl group, Z represents a hydroxyphenyl, alkylhydroxyphenyl, phenylhydroxyphenyl or alkylhydroxybenzyl group, X, Y and Z being bound to the ring carbon atoms by way of -S-, -O-, -NH-, <FORM:0977587/C4-C5/2> (C1-6 alkyl) or <FORM:0977587/C4-C5/3> benzyl and wherein also, if Y is alkylhydroxyphenyl linked by -NH- or alkyl linked by -S- and Z is alkylhydroxyphenyl linked by -NH-, then X may also represent a chlorine atom and if X is alkylhydroxyphenyl linked by -NH-, then Y and Z may both represent chlorine atoms whilst if both X and Y are alkyl groups linked in the stated manner, then Z may represent an alkylhydroxyphenyl group linked by N-alkanoyl.  In examples, a white mineral oil, a Texas cracked petrol with no additives, lard, a high-temperature lubricant comprising diisoamyl adipate, and paraffin wax are stabilized by addition of 6-(4-hydroxy-3,5-di-t-butylanilino) - 2,4 - bis - (n - octylthio)-1,3,5-triazine. Specification 977,589 is referred to.ALSO:Butter is stabilized by incorporating therein (with or without other additives) a compound of the general formula <FORM:0977587/A1-A3/1> wherein X and Y each independently represent an alkyl, cycloalkyl, phenyl, alkylphenyl, alkylhydroxyphenyl, alkylhydroxybenzyl, cyanoalkyl, alkylmercaptoalkyl, alkoxycarbonylalkyl or alkoxycarbonylaryl group, Z represents a hydroxyphenyl, alkylhydroxyphenyl, phenylhydroxyphenyl or alkylhydroxybenzyl group, X, Y and Z being bound to the ring carbon atom, by way of -S-, -O-, -NH-, -N1-(C1-6 alkyl) or -N1- benzyl and wherein also, if Y is alkylhydroxyphenyl linked by -NH- or alkyl linked by -S- and Z is alkylhydroxyphenyl linked by -NH-, then X may also represent a chlorine atom and if X is alkylhydroxyphenyl linked by -NH- then Y and Z may both represent chlorine atoms whilst if both X and Y are alkyl groups linked in the stated manner, then Z may represent an alkylhydroxyphenyl group linked by -N1-alkanoyl. Specification 977,589 is referred to.