Stabilized polymers, novel stabilizers, and synthesis thereof

Claim 2

A stabilized composition of matter which comprises a synthetic lubricant subject to the deleterious effects of oxygen and heat and from about 0.001 percent to about 10 percent by weight of a substitued α-aminoacetamide of the formula ##STR29## wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 independently represent the following substituents: hydrogen; aryl, alkyl having from 1 to about 24 carbon atoms wherein functional groups may be substituted with alkyl groups; hydroxyalkyl having from 1 to about 12 carbon atoms; haloalkyl having from 1 to about 12 carbon atoms; cyanoalkyl having from 2 to about 12 carbon atoms; aminoalkyl or iminoalkyl having from 1 to about 12 carbon atoms; ether groups having from 3 to about 18 carbon atoms; alkenyl and aralkyl having from 7 to about 14 carbon atoms; alkylene having from 1 to about 7 carbon atoms; alkenylene having from 2 to about 10 carbon atoms; each substituent optionally containing a phosphite, ester or hindered phenol group, except that each amine and amide N atom has at least one substituent, and said each substituent in combination, R 1 with R 2 , R 3 with R 4 , and R 5 with R 6 , optionally (i) forms a ring containing from about 5 to about 9 ring atoms, which ring optionally (ii) contains a hetero atom selected from the group consisting of N, S and O, and a moiety selected from the group consisting of keto, ester, amide, thio and ether.

Claim 3

The stabilized composition of matter of claim 1 wherein one of R 3 and R 4 is H.

Claim 4

The stabilized composition of matter of claim 1 wherein R 3 and R 4 are each acyclic.

Claim 5

The stabilized composition of matter of claim 1 wherein one of R 3 and R 4 is acyclic and the other is cyclic.

Claim 6

The stabilized composition of matter of claim 1 wherein R 3 and R 4 are cyclized.

Claim 7

The stabilized composition of matter of claim 1 wherein R 1 and R 2 are acyclic.

Claim 8

The stabilized composition of matter of claim 1 wherein one of R 1 and R 2 is cyclic the ring having from about 5 to about 9 ring members.

Claim 9

The stabilized composition of matter of claim 1 wherein one of R 1 and R 2 is acyclic.

Claim 10

The stabilized composition of matter of claim 1 wherein R 1 and R 2 is each cyclic the ring having from about 5 to about 9 ring members.

Claim 11

The stabilized composition of matter of claim 1 wherein one of R 1 and R 2 is acyclic, and the other cyclic, the ring having from about 5 to about 9 ring members.

Claim 12

The stabilized composition of matter of claim 1 wherein R 1 and R 2 are cyclized, the ring having from about 5 to about 9 ring members.

Claim 13

The stabilized composition of matter of claim 1 wherein R 5 and R 6 are each acyclic.

Claim 14

The stabilized composition of matter of claim 1 wherein one of R 5 and R 6 is cyclic, the ring having from about 5 to about 9 ring members.

Claim 15

The stabilized composition of matter of claim 1 wherein one of R 5 and R 6 is acyclic.

Claim 16

The stabilized composition of matter of claim 1 wherein R 5 and R 6 are each cyclic, each ring having from about 5 to about 9 ring members.

Claim 17

The stabilized composition of matter of claim 1 wherein one of R 5 and R 6 is acyclic, and the other cyclic, the ring having from about 5 to about 9 ring members.

Claim 18

The stabilized composition of matter of claim 1 wherein R 5 and R 6 are cyclized, the ring having from about 5 to about 9 ring members.

Claim 19

The stabilized composition of matter of claim 1 wherein the organic material is lubricant comprising a synthetic polycarboxylate type ester functional fluid.

Claim 20

A catalytic method for directly preparing a substituted α-aminoacetamide having the formula ##STR30## wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 independently represent the following substituents: hydrogen; aryl, alkyl having from 1 to about 24 carbon atoms wherein functional groups may be substituted with alkyl groups; hydroxyalkyl having from 1 to about 12 carbon atoms; haloalkyl having from 1 to about 12 carbon atoms; cyanoalkyl having from 2 to about 12 carbon atoms; aminoalkyl or iminoalkyl having from 1 to about 12 carbon atoms; ether groups having from 3 to about 18 carbon atoms; alkenyl and aralkyl having from 7 to about 14 carbon atoms; alkylene having from 1 to about 7 carbon atoms; alkenylene having from 2 to about 10 carbon atoms; each substituent optionally containing a phosphite, ester or hindered phenol group, except that each amine and amide N atom has at least one substituent, and said each substituent in combination, R 1 with R 2 , R 3 with R 4 , and R 5 and R 6 , optionally (i) forms a ring containing from about 5 to about 9 ring atoms, which ring optionally (ii) contains a hetero atom selected from the group consisting of N, S and O, and a moiety selected from the group consisting of keto, ester, amide, thio and ether, comprising reacting (a) an amine nucleophilic agent with (b) an alkoxide ion generating agent and (c) a dichlorocarbene generating agent, in an aqueous alkaline medium, at a relatively low temperature in the range from about -20° C. to about 50° C., in the presence of a catalytic amount of an onium salt sufficient to yield said substituted α-aminoacetamide.

Claim 21

A catalytic method for directly preparing a substituted α-aminoacetamide having the formula ##STR30## wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 independently represent the following substituents: hydrogen; aryl, alkyl having from 1 to about 24 carbon atoms wherein functional groups may be substituted with alkyl groups; hydroxyalkyl having from 1 to about 12 carbon atoms; haloalkyl having from 1 to about 12 carbon atoms; cyanoalkyl having from 2 to about 12 carbon atoms; aminoalkyl or iminoalkyl having from 1 to about 12 carbon atoms; ether groups having from 3 to about 18 carbon atoms; alkenyl and aralkyl having from 7 to about 14 carbon atoms; alkylene having from 1 to about 7 carbon atoms; alkenylene having from 2 to about 10 carbon atoms; each substituent optionally containing a phosphite, ester or hindered phenol group, except that each amine and amide N atom has at least one substituent, and said each substituent in combination, R 1 with R 2 , R 3 with R 4 , and R 5 and R 6 , optionally (i) forms a ring containing from about 5 to about 9 ring atoms, which ring optionally (ii) contains a hetero atom selected from the group consisting of N, S and O, and a moiety selected from the group consisting of keto, ester, amide, thio and ether, comprising reacting (a) an amine nucleophilic agent with (b) an alkoxide ion generating agent and (c) a dichlorocarbene generating agent, in an aqueous alkaline medium, at a relatively low temperature in the range from about -20° C. to about 50° C., in the presence of a catalytic amount of an onium salt sufficient to yield said substituted α-aminoacetamide.

Claim 22

The catalytic method of claim 19 wherein said amine nucleophilic agent is selected from the group consisitng of primary and secondary amines, said alkoxide ion generating agent is selected from the group consisting of ketones, aldehydes and cyanohydrins, and said dichlorocarbene generating agent is chloroform.

Claim 23

The catalytic method of claim 20 wherein said onium salt has the formula R.sub.n Y.sup.+ X.sup.- wherein Y is selected from the group consisting of N, P and S; R represents either different of identical monovalent organic radicals bonded to Y; X - is a counterion selected from the group consisting of Cl, Br, I, F, SO = 4 and HSO 4 = ; and, n is an integer which is 3 when Y is S, and which is 4 when Y is N or p.

Claim 24

The catalytic method of claim 21 wherein said onium salt has the formula (R.sub.a R.sub.b R.sub.c R.sub.d Y.sup.+)X.sup.- wherein: Y is N or P, and R a -R d are monovalent hydrocarbon radicals selected from the group consisting of alkyl, alkenyl, aryl, alkaryl, aralkyl, and cycloalkyl radicals, optionally substituted with suitable heteroatom-containing functional groups.

Claim 25

The catalytic method of claim 22 wherein said onium salt is a quaternary onium salt of N or P and the total number of carbon atoms is in the range from about 15 to about 40.

Claim 26

A catalytic method for directly preparing a substituted α-aminoacetamide having the formula ##STR31## wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 independently represent the following substituents: hydrogen; aryl, alkyl having from 1 to about 24 carbon atoms wherein functional groups may be substituted with alkyl groups; hyroxyalkyl having from 1 to about 12 carbon atoms; haloalkyl having from 1 to about 12 carbon atoms; cyanoalkyl having from 2 to about 12 carbon atoms; aminoalkyl or iminoalkyl having from 1 to about 12 carbon atoms; ether groups having from 3 to about 18 carbon atoms; hydroxyalkyl ether or cyanoalkyl ether groups having from 4 to about 18 carbon atoms; alkenyl and aralkyl having from 7 to about 14 carbon atoms; alkylene having from 1 to about 7 carbon atoms; alkenylene having from 2 to about 10 carbon atoms; each substituent optionally containing a phosphite, ester or hindered phenol group, except that each amine and amide N atom has at least one substituent, and said each substituent in combination, R 1 with R 2 , R 3 with R 4 , and R 5 with R 6 , optionally (i) forms a ring containing from about 5 to about 9 ring atoms, which ring (ii) contains a hetero atom selected from the group consisting of N, S and O, and a moiety selected from the group consisting of keto, ester, amide, thio and ether, comprising reacting (i) an amine nucleophilic agent with (ii) an α-trihalmethylhydroxy alcohol, in an aqueous alkaline medium, at a relatively low temperature in the range from about -20° C. to about 50° C., in the presence of a catalytic amount of an onium salt sufficient to yield said substituted aminoacetamide.

Claim 27

A catalytic method for directly preparing a substituted α-aminoacetamide having the formula ##STR31## wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 independently represent the following substituents: hydrogen; aryl, alkyl having from 1 to about 24 carbon atoms wherein functional groups may be substituted with alkyl groups; hyroxyalkyl having from 1 to about 12 carbon atoms; haloalkyl having from 1 to about 12 carbon atoms; cyanoalkyl having from 2 to about 12 carbon atoms; aminoalkyl or iminoalkyl having from 1 to about 12 carbon atoms; ether groups having from 3 to about 18 carbon atoms; hydroxyalkyl ether or cyanoalkyl ether groups having from 4 to about 18 carbon atoms; alkenyl and aralkyl having from 7 to about 14 carbon atoms; alkylene having from 1 to about 7 carbon atoms; alkenylene having from 2 to about 10 carbon atoms; each substituent optionally containing a phosphite, ester or hindered phenol group, except that each amine and amide N atom has at least one substituent, and said each substituent in combination, R 1 with R 2 , R 3 with R 4 , and R 5 with R 6 , optionally (i) forms a ring containing from about 5 to about 9 ring atoms, which ring (ii) contains a hetero atom selected from the group consisting of N, S and O, and a moiety selected from the group consisting of keto, ester, amide, thio and ether, comprising reacting (i) an amine nucleophilic agent with (ii) an α-trihalmethylhydroxy alcohol, in an aqueous alkaline medium, at a relatively low temperature in the range from about -20° C. to about 50° C., in the presence of a catalytic amount of an onium salt sufficient to yield said substituted aminoacetamide.

Claim 28

The cataytic method of claim 24 wherein said amine nucleophilic agent is selected from the group consisting of primary and secondary amines, and said α-trihalomethyl alcohol is selected from the group consisting of α-trihalomethylhydroxyalkanes and α-trihalomethylhydroxycycloalkanes.

Claim 29

A substituted α-aminoacetamide compound of the formula ##STR32## wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 independently represent the following substituents: aryl, alkyl having from 1 to about 24 carbon atoms wherein functional groups may be substituted with alkyl groups; hyroxyalkyl having from 1 to about 12 carbon atoms; haloalkyl having from 1 to about 12 carbon atoms; cyanoalkyl having from 2 to about 12 carbon atoms; aminoalkyl or iminoalkyl having from 1 to about 12 carbon atoms; ether groups having from 3 to about 18 carbon atoms; aralkyl having from 7 to about 14 carbon atoms; alkylene having from 1 to about 7 carbon atoms; alkenylene having from 2 to about 10 carbon atoms; and R 1 , R 2 , may in addition independently represent hydrogen; each substituent optionally containing a phosphite, ester or hindered phenol group, except that substituents on the amine N atom are different from substituents on the amide N atom, and said substituents in combination, R 1 with R 2 , R 3 with R 4 , and R 5 with R 6 , optionally (i) forms a ring containing from about 5 to about 9 ring atoms, which ring optionally (ii) contains an O hetero atom.

Claim 30

A substituted α-aminoacetamide compound of the formula ##STR32## wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 independently represent the following substituents: aryl, alkyl having from 1 to about 24 carbon atoms wherein functional groups may be substituted with alkyl groups; hyroxyalkyl having from 1 to about 12 carbon atoms; haloalkyl having from 1 to about 12 carbon atoms; cyanoalkyl having from 2 to about 12 carbon atoms; aminoalkyl or iminoalkyl having from 1 to about 12 carbon atoms; ether groups having from 3 to about 18 carbon atoms; aralkyl having from 7 to about 14 carbon atoms; alkylene having from 1 to about 7 carbon atoms; alkenylene having from 2 to about 10 carbon atoms; and R 1 , R 2 , may in addition independently represent hydrogen; each substituent optionally containing a phosphite, ester or hindered phenol group, except that substituents on the amine N atom are different from substituents on the amide N atom, and said substituents in combination, R 1 with R 2 , R 3 with R 4 , and R 5 with R 6 , optionally (i) forms a ring containing from about 5 to about 9 ring atoms, which ring optionally (ii) contains an O hetero atom.

Claim 31

The compound of claim 26 wherein one of R 1 and R 2 is H and the other selected from the group consisting of aryl, aralkyl and alkaryl; and, R 5 and R 6 are each alkyl.

Claim 32

The compound of claim 26 wherein R 1 and R 2 are cyclized forming a ring, said heteroatom therein is O, and R 5 and R 6 are similarly cyclized.

Claim 33

A substituted α-aminoacetamide compound of the formula ##STR33## wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 independently represent the following substituents: aryl, alkyl having from 1 to about 24 carbon atoms wherein functional groups may be substituted with alkyl groups; hydroxyalkyl having from 1 to about 12 carbon atoms; haloalkyl having from 1 to about 12 carbon atoms; cyanoalkyl having from 2 to about 12 carbon atoms; aminoalkyl or iminoalkyl having from 1 to about 12 carbon atoms; ether groups having from 3 to about 18 carbon atoms; aralkyl having from 7 to about 14 carbon atoms; alkylene having from 1 to about 7 carbon atoms; alkenylene having from 2 to about 10 carbon atoms; and R 1 , R 2 , may in addition independently represent hydrogen; each substituent optionally containing a phosphite, ester or hindered phenol group, except that substituents on the amine N atom are different from substituents on the amide N atom, and said substituents in combination, R 1 with R 2 , R 3 with R 4 , and R 5 with R 6 , optionally (i) forms a ring containing from about 5 to about 9 ring atoms, which ring optionally (ii) contains hetero atoms selected from the group consisting of N, S and O, and a moiety selected from the group consisting of keto, ester, amide, thio and ether.

Claim 34

A substituted α-aminoacetamide compound of the formula ##STR33## wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 independently represent the following substituents: aryl, alkyl having from 1 to about 24 carbon atoms wherein functional groups may be substituted with alkyl groups; hydroxyalkyl having from 1 to about 12 carbon atoms; haloalkyl having from 1 to about 12 carbon atoms; cyanoalkyl having from 2 to about 12 carbon atoms; aminoalkyl or iminoalkyl having from 1 to about 12 carbon atoms; ether groups having from 3 to about 18 carbon atoms; aralkyl having from 7 to about 14 carbon atoms; alkylene having from 1 to about 7 carbon atoms; alkenylene having from 2 to about 10 carbon atoms; and R 1 , R 2 , may in addition independently represent hydrogen; each substituent optionally containing a phosphite, ester or hindered phenol group, except that substituents on the amine N atom are different from substituents on the amide N atom, and said substituents in combination, R 1 with R 2 , R 3 with R 4 , and R 5 with R 6 , optionally (i) forms a ring containing from about 5 to about 9 ring atoms, which ring optionally (ii) contains hetero atoms selected from the group consisting of N, S and O, and a moiety selected from the group consisting of keto, ester, amide, thio and ether.

Claim 35

The compound α-dimethyl-α-p-toluidino-p-methylacetanilide.

Claim 36

The compound α-dimethyl-α-p-toluidino-p-methylacetanilide.

Claim 37

A catalytic method for directly preparing α-dimethyl-α-p-toluidino-p-methylacetanilide having the formula ##STR34## comprising reacting (a) p-toluidine, (b) an alkoxide ion generating agent selected from the group consisting of ketone, aldehyde and cyanohydrin, and (c) a dichlorocarbene generating agent selected from the group consisting of bromoform, chloroform and iodoform, in an aqueous alkaline medium, at a relatively low temperature in the range from about -20° C. to about 50° C., in the presence of a catalytic amount of an onium salt sufficient to yield said α-dimethyl-α-p-toluidino-p-methylacetanilide.

Claim 38

A catalytic method for directly preparing α-dimethyl-α-p-toluidino-p-methylacetanilide having the formula ##STR34## comprising reacting (a) p-toluidine, (b) an alkoxide ion generating agent selected from the group consisting of ketone, aldehyde and cyanohydrin, and (c) a dichlorocarbene generating agent selected from the group consisting of bromoform, chloroform and iodoform, in an aqueous alkaline medium, at a relatively low temperature in the range from about -20° C. to about 50° C., in the presence of a catalytic amount of an onium salt sufficient to yield said α-dimethyl-α-p-toluidino-p-methylacetanilide.

Claim 39

A stabilized composition of matter which comprises a synthetic polycarboxylate type ester functional fluid subject to the deleterious effects of oxygen and heat and from about 0.001 percent to about 10 percent by weight of α-dimethyl-α-p-toluidino-p-methylacetanilide.

Claim 40

A stabilized composition of matter which comprises a synthetic polycarboxylate type ester functional fluid subject to the deleterious effects of oxygen and heat and from about 0.001 percent to about 10 percent by weight of α-dimethyl-α-p-toluidino-p-methylacetanilide.

Claim 41

The compound of claim 26 wherein R 1 , R 2 , R 5 , and R 6 independently represent hydrogen, said aryl and said alkyl; and, R 3 and R 4 represent said aryl and alkyl, optionally forming an alkylene ring containing from 5 to about 9 carbon atoms.

Claim 42

The compound of claim 33 wherein when one of R 3 and R 4 is said alkyl, the other is selected from said alkyl and said aryl.

Claim 43

The compound of claim 33 wherein one of R 1 and R 2 is said aryl, one of R 5 and R 6 is said aryl, and R 4 is said aryl.