Hindered Amine salt compounds

Abstract

The present invention relates water-soluble hindered amine compounds of the general formula (I): wherein G 1 and G 2 are independently alkyl of 1 to 4 carbon atoms or are together pentamethylene; Z 1 and Z 2 are each methyl, or Z 1 and Z 2 together form an unsubstituted linking moiety or a linking moiety substituted by one or more groups selected from an ester, ether, hydroxy, oxo, cyanohydrin, amide, amino, carboxy or an urethane group; E is alkoxy of 1 to 18 carbon atoms, cycloalkoxy of 5 to 12 carbon atoms or aralkoxy of 7 to 15 carbon atoms, or E is —O-T-(OH) b ; T is a straight or branched chain alkylene of 1 to 18 carbon atoms, cycloalkylene of 5 to 18 carbon atoms, cycloalkenylene of 5 to 18 carbon atoms, a straight or branched chain alkylene of 1 to 4 carbon atoms substituted by phenyl or by phenyl substituted by one or two alkyl groups of 1 to 4 carbon atoms; b is 1, 2 or 3 with the proviso that b cannot exceed the number of carbon atoms in T, and when b is 2 or 3, each hydroxyl group is attached to a different carbon atoms of T; and, HY is an inorganic or organic acid; and, wherein the total charge of cations is equal to the total charge of anions.

1 . A compound selected from the group consisting of formulae (A*) to (EE*) and (III) to (IIIc) 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       wherein
 E is alkoxy of 1 to 18 carbon atoms, cycloalkoxy of 5 to 12 carbon atoms or aralkoxy of 7 to 15 carbon atoms, or E is —O-T-(OH) b , 
 T is a straight or branched chain alkylene of 1 to 18 carbon atoms, cycloalkylene of 5 to 18 carbon atoms, cycloalkenylene of 5 to 18 carbon atoms, a straight or branched chain alkylene of 1 to 4 carbon atoms substituted by phenyl or by phenyl substituted by one or two alkyl groups of 1 to 4 carbon atoms; 
 b is 1, 2 or 3 with the proviso that b cannot exceed the number of carbon atoms in T, and when b is 2 or 3, each hydroxyl group is attached to a different carbon atoms of T; 
 R is hydrogen or methyl; and 
 in formula (A*) n is 1 or 2, 
 when n is 1, 
 R 1  is hydrogen, alkyl of 1 to 18 carbon atoms, alkenyl of 2-18 carbon atoms, propargyl, glycidyl, alkyl of 2 to 50 carbon atoms interrupted by one to twenty oxygen atoms, said alkyl substituted by one to ten hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups, or 
 R 1  is alkyl of 1 to 4 carbon atoms substituted by a carboxy group or by —COOZ where Z is hydrogen, alkyl of 1 to 4 carbon atoms or phenyl, or where Z is said alkyl substituted by —(COO − ) n  M n+  where n is 1-3 and M is a metal ion from the 1st, 2nd or 3rd group of the periodic table or is Zn, Cu, Ni or Co, or M is a group N n+ (R 2 ) 4  where R 2  is alkyl of 1 to 8 carbon atoms or benzyl, 
 when n is 2, 
 R 1  is alkylene of 1 to 12 carbon atoms, alkenylene of 4 to 12 carbon atoms, xylylene or alkylene of 1 to 50 carbon atoms interrupted by one to twenty oxygen atoms, substituted by one to ten hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups; 
 in formula (B*), m is 1 to 4, and 
 when m is 1, 
 R 2  is alkyl of 1 to 18 carbon atoms, alkyl of 3 to 18 carbon atoms interrupted by —COO—, alkyl of 3 to 18 carbon atoms substituted by COOH or COO—, or R 2  is —CH 2 (OCH 2 CH 2 ) n OCH 3    
 where n is 1 to 12, or 
 R 2  is cycloalkyl of 5 to 12 carbon atoms, aryl of 6 to 12 carbon atoms, or said aryl substituted by one to four alkyl groups of 1 to 4 carbon atoms, or 
 R 2  is —NHR 3  where R 3  is alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aryl of 6 to 12 carbon atoms, or said aryl substituted by one to four alkyl of 1 to 4 carbon atoms, or 
 R 2  is —N(R 3 ) 2  where R 3  is as defined above, 
 when m is 2, 
 R 2  is alkylene of 1 to 12 carbon atoms, alkenylene of 4 to 12 carbon atoms, xylylene, alkylene of 2 to 12 carbon atoms interrupted by —COO—, alkylene of 3 to 18 carbon atoms substituted by COOH or COO—, or R 2  is —CH 2 (OCH 2 CH 2 ) n OCH 2 — where n is 1 to 12, or 
 R 2  is cycloalkylene of 5 to 12 carbon atoms, aralkylene of 7 to 15 carbon atoms or arylene of 6 to 12 carbon atoms, or 
 R 2  is —NHR 4 NH— where R 4  is alkylene of 2 to 18 carbon atoms, cycloalkylene of 5 to 12 carbon atoms, aralkylene of 8 to 15 carbon atoms or arylene of 6 to 12 carbon atoms, or 
 R 2  is —N(R 3 )R 4 N(R 3 )— where R 3  and R4 are as defined above, or 
 R 2  is —CO—, —NH—CO—NH—, or —N(R 3 )—CO—N(R 3 )—, 
 when m is 3, 
 R 2  is alkanetriyl of 3 to 8 carbon atoms or benzenetriyl, or 
 when m is 4, 
 R 2  is alkanetetrayl of 5 to 8 carbon atoms or benzenetetrayl, 
 in formula (C*), 
 R 10  is hydrogen, alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aralkyl of 7 to 15 carbon atoms, alkanoyl of 2 to 18 carbon atoms, alkenoyl of 3 to 5 carbon atoms or benzoyl, 
 x is 1 or 2, and 
 when x is 1, 
 R 11  is hydrogen, alkyl of 1 to 18 carbon atoms, alkenyl of 2 to 18 carbon atoms, propargyl, glycidyl, alkyl of 2 to 50 carbon atoms interrupted by one to twenty oxygen atoms, said alkyl substituted by one to ten hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups, or 
 R 11  is alkyl of 1 to 4 carbon atoms substituted by a carboxy group or by —COOZ where Z is hydrogen, alkyl of 1 to 4 carbon atoms or phenyl, or where Z is said alkyl substituted by —(COO − ) n  M n+  where n is 1-3 and M is a metal ion from the 1st, 2nd or 3rd group of the periodic table or is Zn, Cu, Ni or Co, or M is a group N n+ (R 2 ) 4  where R 2  is hydrogen, alkyl of 1 to 8 carbon atoms or benzyl, or 
 when x is 2, 
 R 11  is alkylene of 1 to 12 carbon atoms, alkenylene of 4 to 12 carbon atoms, xylylene or alkylene of 1 to 50 carbon atoms interrupted by one to twenty oxygen atoms, substituted by one to ten hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups, 
 in formula (D*), y is 1 to 4, 
 R 10  is as defined above, 
 and R 12  is defined as R 2  above, 
 in formula (E*), k is 1 or 2, 
 when k is 1, 
 R 20  and R 21  are independently alkyl of 1 to 12 carbon atoms, alkenyl of 2 to 12 carbon atoms or aralkyl of 7 to 15 carbon atoms, or R 20  is also hydrogen, or 
 R 20  and R 21  together are alkylene of 2 to 8 carbon atoms or said alkylene substituted by hydroxyl, or are acyloxy-alkylene of 4 to 22 carbon atoms, or 
 when k is 2, 
 R 20  and R 21  are together (—CH 2 ) 2 C(CH 2 —) 2 , 
 in formula (F*), 
 R 30  is hydrogen, alkyl of 1 to 18 carbon atoms, benzyl, glycidyl, or alkoxyalkyl of 2 to 6 carbon atoms, 
 g is 1 or 2, 
 when g is 1, R 31  is defined as R 1  above when n is 1, 
 when g is 2, R 31  is defined as R 1  above when n is 2, 
 in formula (G*), 
 Q 1  is —NR 41 — or —O—, 
 E 1  is alkylene of 1 to 3 carbon atoms, or E 1  is —CH 2 —CH(R 42 )—O— where R 42  is hydrogen, methyl or phenyl, or E 1  is —(CH 2 ) 3 —NH— or E 1  is a direct bond, 
 R 40  is hydrogen or alkyl of 1 to 18 carbon atoms, 
 R 41  is hydrogen, alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aralkyl of 7 to 15 carbon atoms, aryl of 6 to 10 carbon atoms, or R 41  is —CH 2 —CH(R 42 )—OH where R 42  is as defined above, 
 in formula (H*), p is 1 or 2, 
 T 4  is as defined for R 11  when x is 1 or 2, 
 M and Y are independently methylene or carbonyl, preferably M is methylene and Y is carbonyl, 
 in formula (I*), 
 this formula denotes a recurring structural unit of a polymer where T 1  is ethylene or 1,2-propylene or is the repeating structural unit derived from an alpha-olefin copolymer with an alkyl acrylate or methacrylate, and where 
 q is 2 to 100, 
 Q 1  is —N(R 41 )— or —O— where R 41  is as defined above, 
 in formula (J*), 
 r is 1 or 2, 
 T 7  is as defined for R 1  when n is 1 or 2 in formula (A*), 
 preferably T 7  is octamethylene when r is 2, 
 in formula (L*), u is 1 or 2, 
 T 13  is as defined for R 1  when n is 1 or 2 in formula (A*), with the proviso that T 13  is not hydrogen when u is 1, 
 in formula (M*), 
 E 1  and E 2 , being different, each are —CO— or —N(E 5 )— where E 5  is hydrogen, alkyl of 1 to 12 carbon atoms or alkoxycarbonylalkyl of 4 to 22 carbon atoms, preferably E 1  is —CO— and E 2  is —N(E 5 )—, 
 E 3  is hydrogen, alkyl of 1 to 30 carbon atoms, phenyl, naphthyl, said phenyl or said naphthyl substituted by chlorine or by alkyl of 1 to 4 carbon atoms, or phenylalkyl of 7 to 12 carbon atoms, or said phenylalkyl substituted by alkyl of 1 to 4 carbon atoms, 
 E 4  is hydrogen, alkyl of 1 to 30 carbon atoms, phenyl, naphthyl or phenylalkyl of 7 to 12 carbon atoms, or 
 E 3  and E 4  together are polymethylene of 4 to 17 carbon atoms, or said polymethylene substituted by one to four alkyl of 1 to 4 carbon atoms, preferably methyl, 
 in formula (O*), 
 R 10  is as defined for R 10  in formula (C*), 
 in formula (P*), 
 E 6  is an aliphatic or aromatic tetravalent radical, preferably neopentanetetrayl or benzenetetrayl, 
 in formula (T*), 
 R 51  is hydrogen, alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, or aryl of 6 to 10 carbon atoms, 
 R 52  is hydrogen or alkyl of 1 to 18 carbon atoms, or 
 R 51  and R 52  together of alkylene of 4 to 8 carbon atoms, 
 f is 1 or 2, 
 when f is 1, 
 R 50  is as defined for R 11  in formula (C*) when x is 1, or R 50  is —(CH 2 ) z COOR 54  where z is 1 to 4 and R 54  is hydrogen or alkyl of 1 to 18 carbon atoms, or R 54  is a metal ion from the 1st, 2nd or 3rd group of the periodic table or a group —N(R 55 ) 4  where R 55  is hydrogen, alkyl of 1 to 12 carbon atoms or benzyl, 
 when f is 2, 
 R 50  is as defined for R 11  in formula (C*) when x is 2, 
 in formula (U*), 
 R 53 , R 54 , R 55  and R 56  are independently alkyl of I to 4 carbon atoms or are together pentamethylene, 
 in formula (V*), 
 R 57 , R 58 , R 59  and R 60  are independently alkyl of 1 to 4 carbon atoms or are together pentamethylene, 
 in formula (W*), 
 R 61 , R 62 , R 63  and R 64  are independently alkyl of 1 to 4 carbon atoms or are together pentamethylene, 
 R 65  is alkyl of 1 to 5 carbon atoms, 
 M is hydrogen or oxygen, 
 wherein in formulas (Y*) to (BB*), 
 n is 2 to 3, 
 G 1  is hydrogen, methyl, ethyl, butyl or benzyl, 
 m is 1 to 4, 
 x is 1 to 4, 
 when x is 1, R 1  and R 2  are independently alkyl of 1 to 18 carbon atoms, said alkyl interrupted by one to five oxygen atoms, said alkyl substituted by 1 to 5 hydroxyl groups or said alkyl both interrupted by said oxygen atoms and substituted by said hydroxyl groups; cycloalkyl of 5 to 12 carbon atoms, aralkyl of 7 to 15 carbon atoms, aryl of 6 to 10 carbon atoms or said aryl substituted by one to three alkyl of 1 to 8 carbon atoms, or R 1  is also hydrogen, or R 1  and R 2  are together tetramethylene, pentamethylene, hexamethylene or 3-oxapentamethylene, 
 when x is 2, 
 R 1  is hydrogen, alkyl of 1 to 8 carbon atoms, said alkyl interrupted by one or two oxygen atoms, said alkyl substituted by a hydroxyl group, or said alkyl both interrupted by one or two oxygen atoms and substituted by a hydroxyl group, 
 R 2  is alkylene of 2 to 18 carbon atoms, said alkylene interrupted by one to five oxygen atoms, said alkylene substituted by 1 to 5 hydroxyl groups or said alkylene both interrupted by said oxygen atoms and substituted by said hydroxyl groups; o-, m- or p-phenylene or said phenylene substituted by one or two alkyl of 1 to 4 carbon atoms, or 
 R 2  is —(CH 2 ) k O[(CH 2 ) k O] h (CH 2 ) k — where k is 2 to 4 and h is 1 to 40, or 
 R 1  and R 2  together with the two N atoms to which they are attached are piperazin-1,4-diyl, 
 when x is 3, 
 R 1  is hydrogen, 
 R 2  is alkylene of 4 to 8 carbon atoms interrupted by one nitrogen atom, 
 when x is 4, 
 R 1  is hydrogen, 
 R 2  is alkylene of 6 to 12 carbon atoms interrupted by two nitrogen atoms, 
 R 3  is hydrogen, alkyl of 1 to 8 carbon atoms, said alkyl interrupted by one or two oxygen atoms, said alkyl substituted by a hydroxyl group, or both interrupted by one or two oxygen atoms and substituted by a hydroxyl group, 
 p is 2 or 3, 
 in formula (DD*), 
 m is 2 or 3, 
 when m is 2, 
 G is —(CH 2 CHR—O) r CH 2 CHR—, where r is 0 to 3, and R is hydrogen or methyl, and 
 when m is 3, G is glyceryl, 
 in formula (EE*), 
 G 2  is —CN, —CONH 2  or —COOG 3  where G 3  is hydrogen, alkyl of 1 to 18 carbon atoms or phenyl, 
 in formulae (III) to (IIIc) 
 A11 is OR 101  or NR 111 R 112    
 R 101  is alkenyl of 2 to 4 carbon atoms, propargyl, glycidyl, alkyl of 2 to 6 carbon atoms interrupted by one or two oxygen atoms, substituted by one to three hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups, or R 101  is alkyl of 1 to 4 carbon atoms substituted by carboxy or by the alkali metal, ammonium or 
 C 1 -C 4 alkylammonium salts thereof; or R 101  is alkyl substituted by COOE 10  where E 10  is methyl or ethyl, 
 R 102  is alkyl of 3 to 5 carbon atoms interrupted by —COO— or by —CO—, or R 102  is —CH 2 (OCH 2 CH 2 ) c COCH 3  where c is 1 to 4; or 
 R 102  is —NHR 103  where R 103  is alkyl of 1 to 4 carbon atoms, 
 a is 2 to 4, 
 when a is 2, 
 T 11  is —(CH 2 CHR 100 —O) d CH 2 CHR 100 —, where d is 0 or 1, and R 100  is hydrogen or methyl, 
 when a is 3, T 11  is glyceryl, 
 when a is 4, T 11  is neopentanetetrayl, 
 b is 2 or 3, 
 when b is 2, 
 G 11  is —(CH 2 CHR 100 —O) d CH 2 CHR 100 —, where d is 0 or 1, and R 100  is hydrogen or methyl, and 
 when b is 3, G 11  is glyceryl; 
 R 111  is hydrogen, unsubstituted alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by one or two hydroxyl, alkyl of 1 to 4 carbon atoms interrupted by one or two oxygen atoms, or both substituted by one hydroxyl and interrupted by one or two oxygen atoms, 
 R 112  is —CO—R 113  where R 113  has the same meaning as R 111 , or R 113  is NHR 114 , wherein R 114  is unsubstituted alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by one or two hydroxyl, alkyl of 1 to 4 carbon atoms substituted by alkoxy of 1 to 2 carbon atoms, or both substituted by one hydroxyl and by alkoxy of 1 to 2 carbon atoms, or 
 R 111  and R 112  together are —CO—CH 2 CH 2 —CO—, or (CH 2 ) 6 CO—; 
 HY is an inorganic or organic acid; wherein the total charge of cations is equal to the total charge of anions; and 
 Y is phosphate, phosphonate, carbonate, bicarbonate, nitrate, chloride, bromide, bisulfite, sulfite, bisulfate, sulfate, borate, formate, acetate, benzoate, citrate, oxalate, tartrate, acrylate, polyacrylate, fumarate, maleate, itaconate, glycolate, gluconate, malate, mandelate, tiglate, ascorbate, polymethacrylate, a carboxylate of nitrilotriacetic acid, a carboxlylate of hydroxyethylethylenediaminetriacetic acid, a carboxylate of ethylenediaminetetraacetic acid, a carboxylate of diethylenetriaminepentaacetic acid, a carboxylate of diethylenediaminetetraacetic acid, a carboxylate of diethylenetriaminepentaacetic acid, alkylsulfonate, arylsulfonate, or alkyl-substituted arylsulfonate. 
 
     
     
         2 . A compound according to  claim 1  selected from the group consisting of (A*), (B*), (C*), (D*), (Q*), (R*), (Y*), and (Z*),
 wherein   E is alkoxy of 1 to 10 carbon atoms, cycloalkoxy of 5 to 8 carbon atoms or aralkoxy of 7 to 12 carbon atoms, or E is —O-T-(OH) b ,   T is a straight or branched chain alkylene of 1 to 10 carbon atoms, cycloalkylene of 5 to 10 carbon atoms, cycloalkenylene of 5 to 10 carbon atoms, a straight or branched chain alkylene of 1 to 4 carbon atoms substituted by phenyl or by phenyl substituted by one or two alkyl groups of 1 to 4 carbon atoms;   b is 1, 2 or 3 with the proviso that b cannot exceed the number of carbon atoms in T, and when b is 2 or 3, each hydroxyl group is attached to a different carbon atoms of T;   R is hydrogen;   in formula (A*), n is 1 or 2,   when n is 1,   R 1  is hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl of 2-6 carbon atoms, propargyl, glycidyl, alkyl of 2 to 20 carbon atoms interrupted by one to ten oxygen atoms, said alkyl substituted by one to five hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups, or   R 1  is alkyl of 1 to 4 carbon atoms substituted by a carboxy group or by —COOZ where Z is hydrogen or alkyl of 1 to 4 carbon atoms,   when n is 2,   R 1  is alkylene of 1 to 8 carbon atoms, alkenylene of 4 to 8 carbon atoms, alkylene of 1 to 20 carbon atoms interrupted by one to ten oxygen atoms, substituted by one to five hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups,   in formula (B*), m is 1 or 2   when m is 1,   R 2  is alkyl of 1 to 4 carbon atoms or R 2  is CH 2 (OCH 2 CH 2 ) n OCH 3  where n is 1 to 12, or   R 2  is phenyl, or said phenyl substituted by one to three methyl groups, or   R 2  is —NHR 3  where R 3  is alkyl of 1 to 4 carbon atoms or phenyl, or said phenyl substituted by one or two methyl groups,   when m is 2,   R 2  is alkylene of 1 to 8 carbon atoms, alkenylene of 4 to 8 carbon atoms, or R 2  is —CH 2 (OCH 2 CH 2 ) n OCH 2 — where n is 1 to 12, or   R 2  is —NHR 4 NH— where R 4  is of 2 to 6 carbon atoms, aralkylene of 8 to 15 carbon atoms or arylene of 6 to 12 carbon atoms, or   R 2  is —CO— or —NHCONH—,   in formula (C*),   R 10  is hydrogen or, alkanoyl of 1 to 3 carbon atoms,   x is 1 or 2,   when x is 1,   R 11  is hydrogen, alkyl of 1 to 6 carbon atoms or glycidyl, or   R 11  is alkyl of 1 to 4 carbon atoms substituted by a carboxy group or by COOZ where Z is hydrogen or alkyl of 1 to 4 carbon atoms,   when x is 2,   R 11  is alkylene of 1 to 6 carbon atoms,   in formula (D*),   R 10  is hydrogen,   y is 1 or 2,   R 12  is defined as R 2  above,   in formula (Y*) and (Z*),   x is 1 or 2,   when x is 1,   R 1  and R 2  are independently alkyl of 1 to 4 carbon atoms or R 1  and R 2  are together tetramethylene, or pentamethylene,   R 2  is hydrogen or alkyl of 1 to 4 carbon atoms, said alkyl group substituted by a hydroxyl group,   when x is 2,   R 1  is hydrogen, alkyl of 1 to 4 carbon atoms, said alkyl substituted by a hydroxyl group,   R 2  is alkylene of 2 to 6 carbon atoms,   R 3  is as defined above,   HY is an inorganic or organic acid; and, wherein the total charge of cations is equal to the total charge of anions; and   Y is phosphate, phosphonate, carbonate, bicarbonate, chloride, bromide, bisulfate, sulfate, borate, formate, acetate, benzoate, citrate, oxalate, tartrate, acrylate, fumarate, maleate, itaconate, glycolate, gluconate, malate, mandelate, tiglate, ascorbate, a carboxylate of nitrilotriacetic acid, a carboxylate of hydroxyethylethylenediaminetriacetic acid, a carboxylate of ethylenediaminetetraacetic acid, a carboxylate of diethylenetriaminepentaacetic acid, a carboxylate of diethylenediaminetetraacetic acid, a carboxylate of diethylenetriaminepentaacetic acid, alkylsulfonate, arylsulfonate, or alkyl-substituted arylsulfonate.   
     
     
         3 . A compound according to  claim 2  selected from the group consisting of (A*), (B*), (C*), (D*), (Q*), and (R*),
 wherein   E is alkoxy of 1 to 10 carbon atoms, cycloalkoxy of 5 to 8 carbon atoms or aralkoxy of 7 to 12 carbon atoms, or E is —O-T-(OH) b ,   T is a straight or branched chain alkylene of I to 10 carbon atoms, cycloalkylene of 5 to 10 carbon atoms, cycloalkenylene of 5 to 10 carbon atoms, a straight or branched chain alkylene of 1 to 4 carbon atoms substituted by phenyl or by phenyl substituted by one or two alkyl groups of 1 to 4 carbon atoms;   b is 1, 2 or 3 with the proviso that b cannot exceed the number of carbon atoms in T, and when b is 2 or 3, each hydroxyl group is attached to a different carbon atoms of T;   R is hydrogen,   in formula (A*),   h is 1,   R 1  is hydrogen, alkyl of 1 to 4 carbon atoms, glycidyl, alkyl of 2 to 4 carbon atoms interrupted by one or two oxygen atoms, said alkyl substituted by one or two hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups, or   R 1  is alkyl of 1 to 4 carbon atoms substituted by —COOZ where Z is hydrogen or alkyl of 1 to 4 carbon atoms,   in formula (B*),   m is 1 or 2,   R 2  is alkyl of 1 to 4 carbon atoms or R 2  is CH 2 (OCH 2 CH 2 ) n OCH 3  where n is 1 to 4,   when m is 2,   R 2  is alkylene of 1 to 8 carbon atoms,   in formula (C*),   R 10  is hydrogen or alkanoyl of 1 or 2 carbon atoms,   x is 1 or 2,   when x is 1,   R 11  is hydrogen, alkyl of 1 to 4 carbon atoms or glycidyl,   R 11  is alkyl of 1 to 4 carbon atoms substituted by COOZ where Z is hydrogen or alkyl of 1 to 4 carbon atoms,   when x is 2,   R 11  is alkylene of 1 to 6 carbon atoms,   in formula (D*),   R 10  is hydrogen,   y is 1 or 2,   R 12  is defined as R 2  above;   HY is an inorganic or organic acid; and, wherein the total charge of cations is equal to the total charge of anions; and   Y is phosphate, phosphonate, carbonate, bicarbonate, chloride, bromide, bisulfate, sulfate, borate, formate, acetate, benzoate, citrate, oxalate, tartrate, ascorbate, acrylate, fumarate, maleate, itaconate, glycolate, gluconate, malate, mandelate, tiglate, a carboxylate of nitrilotriacetic acid, a carboxylate of hydroxyethylethylenediaminetriacetic acid, a carboxylate of ethylenediaminetetraacetic acid, a carboxylate of diethylenetriaminepentaacetic acid, a carboxylate of diethylenediaminetetraacetic acid, a carboxylate of diethylenetriaminepentaacetic acid, alkylsulfonate, arylsulfonate, or alkyl-substituted arylsulfonate.   
     
     
         4 . A compound according to  claim 1  selected from the group consisting of
 (a) bis(1-octyloxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate hydrochloride;   (b) 1-methoxy-2,2,6,6-tetramethyl-4-acetoxypiperidinium citrate;   (c) 1-methoxy-2,2,6,6-tetramethyl-4-acetamidopiperidinium phosphate;   (d) 1-butoxy-2,2,6,6-tetramethyl-4-acetamidopiperidinium bisulfate;   (e) 1-methoxy-2,2,6,6-tetramethyl-4-oxo-piperidinium methyl sulfonate;   (f) 1-methoxy -2,2,6,6-tetramethyl-4-oxo-piperidinium acetate;   (g) 1-phenoxy-2,2,6,6-tetramethyl-4-methoxy-piperidinium tartrate;   (h) 1-benzoxy-2,2,6,6-tetramethyl-4-methoxy-piperidinium acetate;   (i) 1-ethoxy-2,2,6,6-tetramethyl-4-acetoxypiperidinium maleate;   (j) 1-methoxy-2,2,6,6-tetramethyl-4-propoxy-piperidinium mandelate;   (k) 1-methoxy-2,2,6,6-tetramethyl-4-propoxy-piperidinium oxalate;   (l) 1-methoxy-2,2,6,6-tetramethyl-4-(2-hydroxy-4-oxapentoxy)piperidinium bicarbonate;   (m) 1-methoxy-2,2,6,6-tetramethyl-4-(2-hydroxy-4-oxapentoxy)piperidinium glycolate;   (n) 1-methoxy-2,2,6,6-tetramethyl-4-hydroxypiperidinium gluconate;   (o) 1-methoxy-2,2,6,6-tetramethyl-4-hydroxypiperidinium ascorbate;   (p) 1-methoxy-2,2,6,6-tetramethyl-4-hydroxypiperidinium benzene sulfonate;   (q) 1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-hydroxypiperidinium ascorbate;   (r) 1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-hydroxypiperidinium citrate;   (s) bis(1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-hydroxypiperidinium)citrate;   (t) tris(1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-hydroxypiperidinium)citrate;   (u) tetra(1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-hydroxypiperidinium)ethylenediaminetetraacetate;   (v) tetra(1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-acetamidopiperidinium)ethylenediaminetetraacetate;   (w) tetra(1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-oxopiperidinium)ethylenediaminetetraacetate;   (x) penta(1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-hydroxypiperidinium)diethylenetriaminepentaacetate;   (y) penta(1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-acetamidopiperidinium)diethylenetriaminepentaacetate;   (z) penta(1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-oxopiperidinium)diethylenetriaminepentaacetate;   (aa) tri(1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-hydroxypiperidinium)nitrilotriacetate;   (bb) tri(1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-acetamidopiperidinium)nitrilotriacetate;   (cc) tri(1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-oxopiperidinium)nitrilotriacetate;   (dd) penta(1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-hydroxypiperidinium)diethylenetriaminepentamethylenephosphonate;   (ee) penta(1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-acetamidopiperidinium)diethylenetriaminepentamethylenephosphonate; and,   (ff) penta(1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-oxopiperidinium)diethylenetriaminepentamethylenephosphonate.   
     
     
         5 . A compound according to  claim 4  selected from the group consisting of
 (a) bis(1-octyloxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate hydrochloride;   (b) 1-methoxy-2,2,6,6-tetramethyl-4-acetoxypiperidinium citrate;   (c) 1-butoxy-2,2,6,6-tetramethyl-4-acetamidopiperidinium bisulfate;   (d) 1-methoxy-2,2,6,6-tetramethyl-4-oxo-piperidinium methyl sulfonate;   (e) 1-methoxy-2,2,6,6-tetramethyl-4-oxo-piperidinium acetate;   (f) 1-ethoxy-2,2,6,6-tetramethyl-4-acetoxypiperidinium maleate;   (g) 1-methoxy-2,2,6,6-tetramethyl-4-propoxy-piperidinium oxalate;   (h) 1-methoxy-2,2,6,6-tetramethyl-4-(2-hydroxy-4-oxapentoxy)piperidinium glycolate;   (i) 1-methoxy-2,2,6,6-tetramethyl-4-hydroxypiperidinium ascorbate;   (j) 1-methoxy-2,2,6,6-tetramethyl-4-hydroxypiperidinium benzene sulfonate;   (k) 1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-hydroxypiperidinium ascorbate;   (l) 1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-hydroxypiperidinium citrate;   (m) bis(1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-hydroxypiperidinium)citrate;   (n) tris(1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-hydroxypiperidinium)citrate;   (o) tetra(1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-hydroxypiperidinium)ethylenediaminetetraacetate;   (p) tetra(1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-acetamidopiperidinium)ethylenediaminetetraacetate;   (q) penta(1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-hydroxypiperidinium)diethylenetriaminepentaacetate;   (r) tri(1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-hydroxypiperidinium)nitrilotriacetate;   (s) penta(1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-hydroxypiperidinium)diethylenetriaminepentamethylenephosphonate; and,   (t) penta(1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-4-acetamidopiperidinium)diethylenetriaminepentamethylenephosphonate.