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1. (WO1991018034) ADVANCED AND UNADVANCED COMPOSITIONS, NUCLEOPHILIC DERIVATIVES THEREOF AND CURABLE AND COATING COMPOSITIONS THEREOF
Note: Text based on automatic Optical Character Recognition processes. Please use the PDF version for legal matters

WHAT IS CLAIMED IS:
1. An advanced resin or an unadvanced compound or mixture of such advanced resins and/or unadvanced compounds in any combination represented by the following formulas IA, IB, IC, ID, IE or IF

-

wherein each A is independently a single bond, -O-, -S- -S-S-, -SO-, -SO2-, -CO-, -O-CO-O-, -O-R1-O-, -(O-CH2- CHR2)n-O- or -R3-; each Q is independently a divalent group represented by the formulas


each Q' is independently a divalent aliphatic or
cycloaliphatic group having from 2 to 20 carbon atoms or Q' is a group represented by the formulas

each Q1 is independently a divalent group represented by the formula

each Q2 is a group represented by the formula


each R is independently hydrogen or a C1 to C4 alkyl group; each R' is independently hydrogen or an alkyl group having from 1 to 6 carbon atoms; each Ra is independently a divalent hydrocarbyl group having from 1 to 6 carbon atoms; each Rb is independently hydrogen or a monovalent hydrocarbyl group having from 1 to 6 carbon atoms; R1 is a divalent hydrocarbyl group having from 1 to 36 carbon atoms; R2 is hydrogen, methyl, ethyl or phenyl; R3 is a divalent hydrocarbyl group having from 1 to 36 carbon atoms; each X is independently hydrogen, a halogen, -SO-R4, -SO2-R4, -CO-R4, -CO-O-R4, -O-CO-R4, -S-R4, -OR4, or -R4; R4 is a monovalent hydrocarbyl group having from 1 to 12 carbon atoms; each Y1 is independently -(Q-T)m-Q-; each Y2 is independently -(Q-T)m-Q- or -(Q'-T)m-Q'-, or -(Q-T)m-Q-(O-CH2-C(OH) (R)-CH2-O-(Q-T)m-Q)n3-; each Y3 is independently a divalent group represented by the formulas - (( 1-T )m1-Q 1 - ,

or



- (Q2-T)m1-Q2- ;

each T is independently an -O-R1-O- or -(O-CH2-CHR2)n-O- group; each a independently has a value from 1 to 25; each m independently has a value from zero to 25; ml has a value from 1 to 25; n has a value from 1 to 10; nl has a value from 1 to 100; n2 has a value of 1 or 3; n3 has a value from zero to 10; and x has a value from 2 to 19; characterized in that at least one of said advanced resins or unadvanced compounds contains at least one -0- R1-O- or -(O-CH2-CHR2)n-O- group is present as a bridge between two groups selected independently from the group consisting of (1) a saturated or unsaturated
cycloaliphatic group, (2) an aromatic group, (3) a group represented by the formula


or (4) a group represented by the formula


2. An advanced resin or an unadvanced compound or mixture of such advanced resins and/or unadvanced compounds in any combination of Claim 1 wherein
(a) each (A) is independently a single bond, -O-R1-O-,
-(O-CH2-CHR2)n-O- or -R3-, characterized in that there be at least one A group and that at least one A group is either an -O-R1-O- or -(O-CH2-CHR2)n-O- group;
(b) each R is hydrogen or a methyl group;
(c) each Ra is independently a divalent hydrocarbyl group having from 1 to 4 carbon atoms;
(d) each Rb is independently hydrogen or a monovalent hydrocarbyl group having from 1 to 4 carbon atoms;

(e) each R' is independently hydrogen, or an alkyl group having from 1 to 4 carbon atoms;
(f) each R1 is a divalent hydrocarbyl group having from 2 to 24 carbon atoms;

(g) R2 is hydrogen, methyl or ethyl;
(h) each R3 is a divalent hydrocarbyl group group having from 1 to 24 carbon atoms;
(i) each X is independently hydrogen, a halogen, -SO-R4,

-SO2-R4, -CO-R4,
-CO-O-R4, -O-CO-R4 -S-R4, -OR4, or -R4;
(j) R4 is a monovalent hydrocarbyl group having from 1 to 10 carbon atoms;
(k) a has a value from 1 to 15;
(l) m has a value from zero to 10;
(m) m1 has a value from 1 to 10;
(n) n has a value from 2 to 8;
(o) n1 has a value from 1 to 80;
(p) n3 has a value from 0.1 to 5; and
(q) x has a value from 3 to 10.

3. An advanced resin or an unadvanced compound or mixture of such advanced resins and/or unadvanced compounds in any combination of Claim 1 wherein
(a) each (A) is independently a single bond, -O-R1-O-, -(O-CH2-CHR2)n-O- or -R3-, characterized in that there be at least one A group and that at least one A group is either an -O-R1-O- or
-(O-CH2-CHR2)n-O- group;
(b) each R is iiydrogen;
(c) each Ra is independently a divalent hydrocarbyl
group having from 1 to 2 carbon atoms;
(d) each Rb is independently hydrogen or a monovalent hydrocarbyl group having from 1 to 2 carbon atoms;

(e) each R1 is a divalent hydrocarbyl group having from 2 to 12 carbon atoms;
(f) R2 is hydrogen;

(g) each R3 is a divalent hydrocarbyl group having from

1 to 12 carbon atoms;
(h) each X is independently hydrogen, a halogen, -SO-R4,

-SO2-R4, -CO-R4, -CO-O-R4, -S-R4, -OR4, or -R4;
(i) R4 is a monovalent hydrocarbyl group having from 1 to 8 carbon atoms;
(j) a has a value from 1 to 10;
(k) m has a value from zero to 5;
(1) m1 has a value from 1 to 5;
m) n has a value from 2 to 5;
(n) n1 has a value from 2 to 60; and
(o) x has a value from 3 to 5.

4. An advanced resin prepared by reacting a composition comprising
(1) at least one diglycidyl ether of a compound
containing an average of more than one but not
more than two phenolic hydroxyl groups per
molecule; with
(2) at least one compound containing an average of
more than one but not more than two phenolic
hydroxyl groups per molecule;
wherein components (1) and (2) are employed in amounts which provide a ratio of phenolic hydroxyl groups per epoxide group of from 0.5:1 to 2:1; and characterized in that at least one of the components (1) or (2) contains at least one -O-R1-O- group or a -(O-CH2-CHR2)n-O- group as a bridge between two groups selected independently from the group consisting of (1) a saturated or
unsaturated cycloaliphatic group, (2) an aromatic group, (3) a group represented by the formula

and (4) a group represented by the formula


wherein each Ra is independently a divalent hydrocarbyl group having from 1 to 6 carbon atoms; each Rb is independently hydrogen or a monovalent hydrocarbyl group having from 1 to 6 carbon atoms; R1 is a divalent hydrocarbyl group having from 1 to 36 carbon atoms and R2 is hydrogen, methyl, ethyl or phenyl; each X is independently hydrogen, a halogen, -SO-R4, -SO2-R4, -CO-R4, -CO-O-R4, -O-CO-R4, -S-R4, -OR4, or -R4; R4 is a monovalent hydrocarbyl group having from 1 to 12 carbon atoms; n has a value from 1 to 10; and x has a value from 2 to 19.

5. An advanced resin of Claim 4 wherein (a) component (1) is a compound represented by the
following formulas IE, II or III

Formula III


wherein each A is independently a single bond, -O-, -S-, -S-S-, -SO-, -SO2-, -CO-, -O-CO-O-, -O-R1-O-, - (O-CH2-CHR2)n-O-, or -R3-; each Q is independently a divalent group represented by the formulas


each Q' is independently a divalent aliphatic or cycloaliphatic group having from 2 to 20 carbon atoms or Q' is a group represented by the formulas


each Q1 is independently a divalent group represented by the formula



each Q2 is a group represented by the formula


each R is independently hydrogen or a C1 to C4 alkyl group; each R' is independently hydrogen or an alkyl group having from 1 to 6 carbon atoms; each Ra is independently a divalent hydrocarbyl group having from 1 to 6 carbon atoms; each Rb is independently hydrogen or a monovalent hydrocarbyl group having from 1 to 6 carbon atoms; R1 is a divalent hydrocarbyl group having from 1 to 36 carbon atoms; R2 is hydrogen, methyl, ethyl or phenyl; R3 is a divalent hydrocarbyl group having from 1 to 36 carbon atoms;
T is -OR1O- or -(O-CH2-CHR2-)n-O-; each Y1 is
independently -(Q-T)m-Q-; each Y2 is independently - (Q-T)m-Q- or -(Q'-T)m-Q', or -(Q-T)m-Q-(O-CH2- C(OH)(R)-CH2-O-(Q-T)m-Q)n3; each Y3 is independently a divalent group represented by the formulas -(Q1-T)m1-Q1- ,

or



-(Q2-T)m1-Q2- ;

each X is independently hydrogen, a halogen, -SO- R4, -SO2-R4, -CO-R4, -CO-O-R4, -O-CO-R4, -S-R4, -OR4, or -R4 wherein R4 is a monovalent hydrocarbyl group having from 1 to 12 carbon atoms; each a
independently has a value from 1 to 25; each m
independently has a value from zero to 25; ml has a value from 1 to 25; n has a value from 1 to 10; n1 has a value from 1 to 100; n2 has a value of 1 or 3; n3 has a value from zero to 10; and x has a value from 2 to 19
(b) component (2) is a compound represented by the
following formula IB, VIA or VIB

HO - Y OH

Formula VIB HO — Y2 OH

wherein R, Yl, Y2, and nl are as defined above;
(c) components (1) and (2) are employed in quantities which provide a ratio of phenolic hydroxyl groups to epoxide group of from 0.7:1 to 1:1 and
(d) at least 50 percent of the groups between .two groups selected independently from the group consisting of (1) a saturated or unsaturated cycloaliphatic group, (2) an aromatic group, (3) a group represented by the formula

and (4) a group represented by the formula
(X)4
-Ra XX Ra
are -O-R1-O- groups or -(O-CH2-CHR2)n-O- groups.

6. An advanced resin of Claim 4 wherein
(a) component (1) is a diglycidyl ether of: bisphenol A, bisphenol F, 1,8-bis(4-hydroxyphenoxy)octane, 1,2- bis(3- hydroxyphenoxy)ethane, 1,8-bis(3- hydroxyphenoxy)octane, poly(bisphenol A)ether of
ethylene glycol, poly(bisphenol F)ether of ethylene glycol, the reaction product of bisphenol A with
from 2 to 6 moles of propylene oxide, or any
combination thereof;
(b) component (2) is: bisphenol A, bisphenol F,
1,2-bis(3-hydroxyphenoxy)ethane,
1,4-bis(3-hydroxyphenoxy)butane,
1,8-bis(4-hydroxyphenoxy)octane,
1,8-bis(3-hydroxyphenoxy)octane,
1,4-bis(4-hydroxyphenoxy)butane,
poly(bisphenol A)ether of ethylene glycol,
poly(bisphenol F)ether of ethylene glycol, or any combination thereof; and
(c) components (1) and (2) are employed in quantities which provide a ratio of phenolic hydroxyl groups to epoxide group of from 0.75:1 to 0.95:1.

7. An acidified advanced resin or an acidified unadvanced compound resulting from reacting a composition comprising
(A) at least one nucleophilic compound;
(B) at least one advanced resin or unadvanced
compound or any combination of such advanced
resins and/or unadvanced compounds represented
by the following formulas IA, IC, or IE

wherein each A is independently a single bond, -O-, -S-,
-S-S-, -SO-, -SO2-, -CO-, -O-CO-O-, -O-R1-O-,
-(O-CH2-CHR2)n-O-, or -R3-, each Q is independently a
divalent group represented by the formulas


each Q' is independently a divalent aliphatic or
cycloaliphatic group having from 2 to 20 carbon atoms or
Q' is a group represented by the formulas;


each Q1 is independently a divalent group represented by
the formula

each Q2 is independently a group represented by the formula


each R is independently hydrogen or a C1 to C4 alkyl group; each R1 is independently hydrogen or an alkyl group having from 1 to 6, carbon atoms; each Ra is independently a divalent hydrocarbyl group having from 1 to 6 carbon atoms; each Rb is independently hydrogen or a monovalent hydrocarbyl group having from 1 to 6 carbon atoms; R1 is a divalent hydrocarbyl group having from 1 to 36 carbon atoms; R2 is hydrogen, methyl, ethyl or phenyl; R3 is a divalent hydrocarbyl group having from 1 to 36, carbon atoms; T is -OR1O- or -(O-CH2-CHR2-)n-O-; each X is independently hydrogen, a halogen, -SO-R4, -SO2-R4, -CO-R4, -CO-O-R4, -O-CO-R4, -S-R4, -OR4, or -R4; R4 is a monovalent hydrocarbyl group having from 1 to 12 carbon atoms; each Y1 is independently -(Q-T)m-Q-; each Y2 is independently -(Q-T)m-Q- or -(Q'-T)m-Q', or -(Q-T)m-Q-(O-CH2-C(OH)(R)-CH2-O-(Q-T)m-Q)n3; each Y3 is independently a divalent group represented by the formulas -(Q1-T)m1-Q1- ,

or



-(Q2-T)m1-Q2- ;

each a independently has a value from 1 to 25; each m independently has a value from zero to 25; m1 has a value from 1 to 25; n has a value from 1 to 10; and n1 has a value from 1 to 100; n2 has a value of 1 or 3; n3 has a value from zero to 10; and x has a value from 2 to 19; characterized in that at least one of said advanced resins or unadvanced compounds contains at least one -O- R1-O- or -(O-CH2-CHR2)n-O- group as a bridge between two groups selected independently from the group consisting of (1) a saturated or unsaturated cycloaliphatic group, (2) an aromatic group, (3) a group represented by the formula


or (4) a group represented by the formula

(C) at least one Bronsted acid.

8. An acidified advanced resin or an acidified unadvanced resin of Claim 7 wherein
(a) component (A) is a monopyridine compound represented by the formulas VII-IX
Formula VII

Formula VIII

Formula IX


wherein each Rc and Rd is independently hydrogen, a halogen atom, particularly chlorine or bromine, a hydrocarbyl or hydrocarbyloxy or a hydroxy substituted hydrocarbyl group having from 1 to 10, carbon atoms, a carbamoyl group (-CO-NH2), or a hydroxyl group; or a polypyridine compound
represented by the formulas X-XII
Formula X


Formula XI

Formula XII



wherein each Rc is independently hydrogen, a halogen atom, particularly chlorine or bromine, a.
hydrocarbyl or hydrocarbyloxy or a hydroxy
substituted hydrocarbyl group having from 1 to 10, preferably from 1 to 4, carbon atoms, a carbamoyl group (-CO-NH2), or a hydroxyl group; each Re is independently an alkyl group having from 1 to 10 carbon atoms, an amine group, a urea group, a thiourea group, a carbonyl group, -S-S- group, -S-CH2-CH2-S- group, -C(OH)H-CO-group, or an amide group; and each y independently has a value from 1 to 5; tetramethyl thiourea, tetraethyl thiourea, hydroxyethylmethyl sulfide, hydroxyethylethyl sulfide, dimethyl sulfide, diethyl sulfide, di-n-propyl sulfide, methyl-n-propyl sulfide, methylbutyl sulfide, dibutyl sulfide, dihydroxyethyl sulfide, bis-hydroxybutyl sulfide, trimethylene sulfide, thiacyclohexane, tetrahydrothiophene, dimethyl amine, diethyl amine, dibutyl amine, 2- (methylamino)ethanol, diethanolamine and the ketimine derivatives of polyamines containing secondary and primary amino groups such as those produced by the reaction of diethylene triamine or N-aminoethylpiperazine with acetone, methyl ethyl ketone or methylisobutyl ketone; N-methylpiperidine, N-ethylpyrrolidine, N-hydroxyethylpyrrolidine, tri- methylphosphine, triethylphosphine, tri-n-butyl- phosphine, trimethylamine, triethylamine, tri-n- propylamine, tri-isobutylamine, hydroxyethyl- dimethylamine, butyldimethylamine,
trihydroxyethylamine, triphenylphosphorus,
N,N,N-dimethylphenethylamine, methyldiethanolamine, dimethylethanolamine, or any combination thereof; (b) in component (B), each (A) is independently a single bond, -O-R1-O-, -(O-CH2-CHR2)n-O- or -R3-,
characterized in that there be at least one A group and that at least one A group is either an -O-R1-O- or -(O-CH2-CHR2)n-O- group;
(c) in component (B), each R is hydrogen or a methyl
group;
(d) in component (B), each Ra is independently a
divalent hydrocarbyl group having from 1 to 4 carbon atoms;
(e) in component (B), each Rb is independently hydrogen or a monovalent hydrocarbyl group having from 1 to 4 carbon atoms;
(f) in component (B), each R' is independently hydrogen, or an alkyl group having from 1 to 4 carbon atoms;

(g) in component (B), each R1 is a divalent hydrocarbyl group haviftg from 2 to 24 carbon atoms;
(h) in component (B), R2 is hydrogen, methyl, or ethyl; (i) in component (B), each R3 is a divalent hydrocarbyl group having from 1 to 24 carbon atoms;
(j) in component (B), each X is independently hydrogen, a a halogen, -SO-R4, -SO2-R4, -CO-R4,
-CO-O-R4, -O-CO-R4 -S-R4, -OR4, or -R4;
(k) in component (B), R4 is a monovalent hydrocarbyl group having from 1 to 10 carbon atoms;

(1) in component (B), each m independently has value
from zero to 10;
(m) in component (B), a has a value from 1 to 15;
(n) in component (B), m has a value from zero to 10;
(o) in component (B), m1 has a value from 1 to 10;
(p) in component (B), n has a value from 2 to 8;
(q) in component (B), n1 has a value from 2 to 80;;
(r) n3 has a value from 0.1 to 5; and
(s) x has a value from 3 to 10; and
(t) component (C) is present in an amount which provides a ratio of moles of acid per mole of nucleophilic compound of from 0.2:1 to 10:1.

9. An acidified advanced resin or an acidified unadvanced resin of Claim 7 wherein
(a) component (A) is nicotinamide;
(b) in component (B), each (A) is independently a single bond, -O-R1-O-, -(O-CH2-CHR2)n-O- or -R3-,
characterized in that there be at least one A group and that at least one A group is either an -O-R1-O- or
-(O-CH2-CHR2)n-O- group;
(c) in component (B), each R is hydrogen;
(d) in component (B), each Ra is independently a
divalent hydrocarbyl group having from 1 to 2 carbon atoms;
(e) in component (B), each Rb is independently hydrogen or a monovalent hydrocarbyl group having from 1 to 2 carbon atoms;
(f) in component (B), each R1 is a divalent hydrocarbyl group having from 2 to 12 carbon atoms;
(g) in component (B), R2 is hydrogen;
(h) in component (B), each R3 is a divalent hydrocarbyl group having from 1 to 12 carbon atoms;

(i) in component (B), each X is independently hydrogen, a halogen, -SO-R4, -SO2-R4, -CO-R4, -CO-O-R4, -O-CO- R4, -S-R4, -OR4, or -R4;
(j) in component (B), R4 is a hydrocarbyl group having from 1 to 8 carbon atoms;
(k) in component (B), m has a value from zero to 5;
(1) in component (B), m1 has a value from 1 to 5;
(m) in component (B), n has a value from 2 to 5;
(n) in component (B), n1 has a value from 2 to 60;
(o) in component (B), x has a value from 3 to 5;
(p) component (C) is lactic acid;
(q) components (A) and (B) are employed in amounts which provide a ratio of moles of nucleophilic compound per epoxide group of from 0.4:1 to 1:1; and
(r) component (C) is present in an amount which provides a ratio of moles of acid per mole of nucleophilic compound of from 0.5:1 to 1.5:1.

10. An acidified advanced resin comprising the product resulting from reacting a composition comprising
(A) at least one nucleophilic compound;
(B) at least one advanced resin comprising the
product prepared by reacting
(1) at least one diglycidyl ether of a compound containing an average of more than one but
not more than two phenolic hydroxyl groups
per molecule; with
(2) at least one compound containing an average of more than one but not more than two
phenolic hydroxyl groups per molecule;
wherein components (1) and (2) are employed in
amounts which provide a ratio of phenolic
hydroxyl groups per epoxide group of from 0.5:1 to 0.95:1; and characterized in that at least one of the components (1) or (2) contains at least one -O-R1-O- group or -(O-CH2-CHR2)n-O-group as a bridge between two groups selected independently from the group consisting of (1) a saturated or unsaturated cycloaliphatic group, (2) an aromatic group, (3) a group represented by the formula


or (4) a group represented by the formula



wherein each Ra is independently a divalent
hydrocarbyl group having from 1 to 6 carbon
atoms; each Rb is independently hydrogen or a
monovalent hydrocarbyl group having from 1 to 6 carbon atoms; R1 is a divalent hydrocarbyl group having from 1 to 36 carbon atoms; R2 is
hydrogen, methyl, ethyl or phenyl; each X is
independently hydrogen, a halogen,
-SO-R4, -SO2-R4, -CO-R4, -CO-O-R4, -O-CO-R4, -S- R4, -OR4, or -R4; R4 is a monovalent hydrocarbyl group having from 1 to 12 carbon atoms; n has a value from 1 to 10; and x has a value from 2 to 19; and
(C) at least one Bronsted acid.

11. An acidified advanced resin of Claim 10 wherein
(a) component (A) is a monopyridine compound represented by the formulas VII-IX Formula VII

Formula VIII

Formula IX


wherein each Rc and Rd is independently hydrogen, a halogen atom, particularly chlorine or bromine, a hydrocarbyl or hydrocarbyloxy or a hydroxy
substituted hydrocarbyl group having from 1 to 10, carbon atoms, a carbamoyl group (-CO-NH2), or a hydroxyl group; or a polypyridine compound
represented by the formulas X-XII
Formula X


Formula XI

Formula XII



wherein each Rc is independently hydrogen, a halogen atom, particularly chlorine or bromine, a
hydrocarbyl or hydrocarbyloxy or a hydroxy
substituted hydrocarbyl group having from 1 to 10, preferably from 1 to 4, carbon atoms, a carbamoyl group (-CO-NH2), or a hydroxyl group; each Re is
independently an alkyl group having from 1 to 10 carbon atoms, an amine group, a urea group, a thiourea group, a carbonyl group, -S-S- group, -S- CH2-CH2-S- group, -C(OH)H-CO-group, or an amide group; and each y independently has a value from 1 to 5;
tetramethyl thiourea, tetraethyl thiourea,
hydroxyethylmethyl sulfide, hydroxyethylethyl sulfide, dimethyl sulfide, diethyl sulfide, di-n- propyl sulfide, methyl-n-propyl sulfide, methylbutyl sulfide, dibutyl sulfide, dihydroxyethyl sulfide, bis-hydroxybutyl sulfide, trimethylene sulfide,
thiacyclohexane, tetrahydrothiophene, dimethyl amine, diethyl amine, dibutyl amine, 2- (methylamino)ethanol, diethanolamine and the
ketimine derivatives of polyamines containing
secondary and primary amino groups such as those
produced by the reaction of diethylene triamine or N-aminoethylpiperazine with acetone, methyl ethyl ketone or methylisobutyl ketone; N-methylpiperidine, N-ethylpyrrolidine, N-hydroxyethylpyrrolidine, tri- methylphosphine, triethylphosphine, tri-n-butyl- phosphine, trimethylamine, triethylamine, tri-n- propylamine, tri-isobutylamine, hydroxyethyl- dimethylamine, butyldimethylamine,
trihydroxyethylamine, triphenylphosphorus,
N,N,N-dimethylphenethylamine, methyldiethanolamine, dimethylethanolamine, or any combination thereof; (b) component (B1) is a compound represented by the
following formulas IE, II or III

Formula II


Formula III


wherein each A is independently a single bond, -O-, -S-, -S-S-, -SO-, -SO2-, -CO-, -O-CO-O-, -O-R1-O-, - (O-CH2-CHR2)n-O- or
-R3-; each R is hydrogen or a C1 to C4 alkyl group; each R' is independently hydrogen or an alkyl group having from 1 to 6 carbon atoms; each Ra is
independently a divalent hydrocarbyl group having
from 1 tt 6 carbon atoms; each Rb is independently
hydrogen or a monovalent hydrocarbyl group having
from 1 to 6, carbon atoms; R1 is a divalent
hydrocarbyl group having from 1 to 24 carbon atoms; R2 is hydrogen, methyl, ethyl or phenyl; R3 is a
divalent hydrocarbyl group having from 1 to 36
carbon atoms;

T is -OR1O- or -(O-CH2-CHR2-)n-O-; each Y1 is
independently -(Q-T)m-Q-; each Y2 is independently - (Q-T)m-Q- or -(Q'-T)m-Q', or -(Q-T)m-Q-(O-CH2- C(OH)(R)-CH2-O-(Q-T)m-Q)n3; each Y3 is independently a divalent group represented by the formulas

-(Q1-T)m1-Q1- ,

or



-(Q2-T)m1-Q2-

each X is independently hydrogen, a halogen, -SO- R4,
-SO2-R4, -CO-R4, -CO-O-R4, -O-CO-R4, -S-R4, -OR4 or
-R4, wherein R4 is a monovalent hydrocarbyl group having from 1 to 12 carbon atoms; m has a value from zero to 25; and n has a value from 1 to 10;
(c) comp(nent (B2) is a compound represented by the
following formulas IB, VIA or VIB

Formula VIA HO — Y1 — OH

Formula VIB HO — Y2 — OH

wherein R, Y1, Y2, and n1 are as defined above;
(d) components (B1) and (B2) are employed in quantities which provide a ratio of phenolic hydroxyl groups to epoxide group of from 0.7:1 to 1:1; and
(e) components (A) and (B) are employed in amounts which provide a ratio of moles of nucleophilic compound per epoxide group of from 0.15 to 1.1:1;
(f) component (C) is present in an amount which provides a ratio of moles of acid per mole of nucleophilic compound of from 0.2:1 to 10:1; and
(g) at least 50 percent of the groups between two groups selected independently from the group consisting of

(1) a saturated or unsaturated cycloaliphatic group,

(2) an aromatic group, (3) a group represented by the formula


and (4) a group represented by the formula

are -O-R1-O- groups or -(O-CH2-CHR2)n-O- groups .

12. An acidified advanced resin of Claim 10 wherein
(a) component (A) is nicotinamide;
(b) component (B1) is a diglycidyl ether of: bisphenol
A, bisphenol F, 1,8-bis(4-hydroxyphenoxy)octane,
1,2-bis(3- hydroxyphenoxy)ethane, 1,8-bis(3- hydroxyphenoxy)octane, poly(bisphenol A)ether of
ethylene glycol, poly(bisphenol F)ether of ethylene glycol, the reaction product of bisphenol A with
from 2 to 6 moles of propylene oxide, or any
combination thereof;
(c) component (B2) is: bisphenol A, bisphenol F,
1,2-bis(3-hydroxyphenoxy)ethane,
1,4-bis(3-hydroxyphenoxy)butane,
1,8-bis(4-hydroxyphenoxy)octane,
1,8-bis(3-feydroxyphenoxy)octane,
1,4-bis(4-hydroxyphenoxy)butane,
poly(bisphenol A)ether of ethylene glycol,
poly(bisphenol F)ether of ethylene glycol, or any combination thereof;
(d) component (C) is lactic acid;
(e) components (B1) and (B2) are employed in quantities which provide a ratio of phenolic hydroxyl groups to epoxide group of from 0.75:1 to 0.95:1;

(f) components (A) and (B) are employed in amounts which provide a ratio of pyridine groups per epoxide group of from 0.4 to 1:1; and
(g) component (C) is present in an amount which provides a ratio of moles of acid per pyridine group of from 0.5:1 to 1.5:1.

13. A curable composition comprising a composition of Claim 1, 2, 3, 4, 5 or 6 and a curing amount of a suitable curing agent therefor.

14. A coating composition comprising a curable composition of Claim 13.

15. An article coated with a coating composition of Claim 14 which coating has subsequently been cured.

16. An aqueous dispersion comprising an acidified advanced resin of Claim 7, 8, 9, 10, 11 or 12, water and a curing amount of a suitable curing agent.

17. A coating composition comprising an aqueous dispersion of Claim 16.

18. An article coated with a coating compostion of Claim 15 which coating has subsequently been cured.

19. A process for coating an aqueous cationic epoxy resin based composition onto an object having an electroconductive surface by steps comprising immersing the electroconductive object into a coating bath comprising an aqueous dispersion of cationic particles of the epoxy based composition, passing an electric current through said bath sufficient to
electrodeosit a coating of said compsition on the object by providing a difference of electric potential between the object and an electrode that is (a) spaced apart from said object, (b) is in electrical contact with said bath, and (c) is electrically positive in relation to said object; wherein said aqueous cationic epoxy resin based composition contains any of the aforementioned cationic epoxy-containing compositions and a curing amount of a suitable curing agent therefor.

20. An article coated by the process of Claim 19 which coating has subsequently been cured.