US4484994A — Hydroxyalkyl carbamate-containing resins for cath…

Claim 1

Independent Claim 18 words

A cathodically electrodepositable, self-cross-linkable polymer containing hydroxyalkyl carbamate groups and one or more tertiary amine groups per molecule.

Claim 2

Dependent Claim 18 words

A cathodically electrodepositable, self-cross-linkable polymer containing hydroxyalkyl carbamate groups and one or more tertiary amine groups per molecule.

Claim 3

Dependent Claim 51 words

The polymer of claim 1 obtained as the reaction product of (a) an epoxy resin having an average epoxy equivalent weight of from about 300 to about 10,000, and (b) one or more amines having at least one secondary amine group and at least one hydroxyalkyl carbamate group or precursor thereof.

Claim 4

Dependent Claim 21 words

The polymer of claim 2 wherein said hydroxyalkyl carbamate groups are obtained by reaction of an amine with a cyclic carbonate.

Claim 5

Dependent Claim 57 words

The polymer of claim 2 wherein said epoxy resin is selected from the group consisting of: (i) the reaction product of epichlorohydrin and a polyhydric phenol, (ii) the epoxy resin of (i) modified by reaction with carboxylate containing polybutadiene polymers, and (iii) the reaction product of epichlorohydrin and a condensation product of phenol with acetone and formaldehyde.

Claim 6

Dependent Claim 20 words

The polymer of claim 1 containing from about 0.6 to about 3.5 meq hydroxyalkyl carbamate per gram of resin solids.

Claim 7

Dependent Claim 20 words

The polymer of claim 1 containing from about 0.6 to about 2.9 meq hydroxyalkyl carbamate per gram of resin solids.

Claim 8

Dependent Claim 20 words

The polymer of claim 1 containing from about 1.1 to about 2.5 meq hydroxyalkyl carbamate per gram of resin solids.

Claim 9

Dependent Claim 19 words

The polymer of claim 1 containing from about 0.5 to about 5 meq amine per gram of resin solids.

Claim 10

Dependent Claim 19 words

The polymer of claim 1 containing from about 0.7 to about 5 meq amine per gram of resin solids.

Claim 11

Dependent Claim 21 words

The polymer of claim 2 wherein said epoxy resin has an epoxy equivalent weight of from about 1,000 to about 4,000.

Claim 12

Dependent Claim 15 words

The polymer of claim 1 further having one or more hydrophobic amine groups pendant thereon.

Claim 13

Dependent Claim 96 words

A cathodically electrodepositable self-cross-linkable polymer comprising a hydroxyalkyl carbamate-containing resin having more than one tertiary amine group and two or more hydroxyalkyl carbamate groups per molecule, said polymer further containing from about 0.6 to about 3.5 meq hydroxyalkyl carbamate per gram and from about 0.5 to about 5 meq amine per gram and being obtained by reaction of epoxy groups of one or more epoxides with a secondary amine group of one or more amines containing carbamate groups or precursors thereof, said epoxide having an average epoxy equivalent weight of from about 300 to about 10,000.

Claim 14

Dependent Claim 96 words

A cathodically electrodepositable self-cross-linkable polymer comprising a hydroxyalkyl carbamate-containing resin having more than one tertiary amine group and two or more hydroxyalkyl carbamate groups per molecule, said polymer further containing from about 0.6 to about 3.5 meq hydroxyalkyl carbamate per gram and from about 0.5 to about 5 meq amine per gram and being obtained by reaction of epoxy groups of one or more epoxides with a secondary amine group of one or more amines containing carbamate groups or precursors thereof, said epoxide having an average epoxy equivalent weight of from about 300 to about 10,000.

Claim 15

Dependent Claim 55 words

The polymer of claim 12 wherein said epoxide is selected from the group consisting of (i) the reaction product of epichlorohydrin and polyhydric phenol, (ii) the epoxy polymer of (i) modified by reaction with carboxylate containing polybutadiene polymers, and (iii) the reaction product of epichlorohydrin and the condensation product of phenol and acetone and formaldehyde.

Claim 16

Dependent Claim 225 words

The polymer of claim 12 wherein said one or more amines are selected from the group consisting of: ##STR17## wherein A is [NH(CH 2 ) x ] n NH; n is 0 to 10; each x is independently 2 to 6; each of R 1 and R 2 is independently H, or a C 1 to C 20 alkyl, cycloalkyl or alkyl aromatic moiety or any of the foregoing containing one or more heteroatoms in addition to at least one carbon atom; ##STR18## wherein: y is 2 or 3; each of R 1 and R 2 is as defined above; and R 3 is a C 1 to C 20 alkyl, cycloalkyl or alkyl aromatic moiety; ##STR19## wherein: each of R 4 and R 6 is independently H or C 1 to C 4 alkyl moieties and each of R 5 and R 7 is independently a C 1 to C 4 alkyl moiety or such moiety containing one or more heteroatoms in addition to at least one carbon atom; and ##STR20## wherein each of R 1 and R 2 is as defined above and each R 8 is independently a C 2 to C 6 alkylene moiety; and said polymer contains from about 0.6 to about 2.9 meq hydroxyalkyl carbamate and from about 0.5 to about 5 meq amine per gram of resin solids.

Claim 17

Dependent Claim 74 words

The polymer of claim 12 wherein said epoxide is a polyepoxide selected from the group consisting of polyepoxides of the formulas: ##STR21## where R 9 is the repeating fragment ##STR22## and n 1 is from 0 to 12; ##STR23## where R' is a hydrogen or a methyl group and R 10 is a hydrogen atom or a glycidyl group and n 2 is from 0 to 12; and (c) an aromatic novalac bisphenol-A resin.

Claim 18

Dependent Claim 23 words

The polymer of claim 12 further including one or more hydrophobic amine groups joined to said cathodically depositable polymer to enhance hydrophobicity thereof.

Claim 19

Independent Claim 125 words

A method of preparing a cathodically electrodepositable, self-cross-linkable polymer comprising reacting (a) an epoxide having an average epoxy equivalent weight of from about 300 to about 10,000, with (b) an amine containing at least one secondary amine group and at least one group selected from the class consisting of hydrolyzable blocked primary amine groups and hydroxyalkyl carbamate groups, to form a substantially epoxy-free material and, when said blocked primary amine groups are present, hydrolyzing the same to unblock said primary amine groups and then reacting a cyclic carbonate with said primary amine groups to form said hydroxyalkyl carbamate groups; the reactants (a) and (b) being selected to form said polymer with from about 0.6 to about 3.5 meq hydroxyalkyl carbamate per gram of resin solids.

Claim 20

Independent Claim 125 words

A method of preparing a cathodically electrodepositable, self-cross-linkable polymer comprising reacting (a) an epoxide having an average epoxy equivalent weight of from about 300 to about 10,000, with (b) an amine containing at least one secondary amine group and at least one group selected from the class consisting of hydrolyzable blocked primary amine groups and hydroxyalkyl carbamate groups, to form a substantially epoxy-free material and, when said blocked primary amine groups are present, hydrolyzing the same to unblock said primary amine groups and then reacting a cyclic carbonate with said primary amine groups to form said hydroxyalkyl carbamate groups; the reactants (a) and (b) being selected to form said polymer with from about 0.6 to about 3.5 meq hydroxyalkyl carbamate per gram of resin solids.

Claim 21

Dependent Claim 39 words

The method of claim 17 wherein said epoxide has an average epoxy equivalent weight of from about 4,000 to about 10,000 and said polymer has from about 0.6 to about 2.9 meq hydroxyalkyl carbamate per gram of resin solids.

Claim 22

Dependent Claim 23 words

The method of claim 17 further including reacting one or more hydrophobic amines with said epoxy resin to enhance hydrophobicity of said polymer.

Claim 23

Dependent Claim 76 words

An electrodeposition bath comprising an aqueous dispersion of an acidified, cathodically electrodepositable, self-cross-linkable polymer containing at least two hydroxyalkyl carbamate groups and at least one tertiary amine group per molecule, and obtained as the reaction product of (a) an epoxy resin having an average molecular weight of from about 300 to about 10,000, and (b) one or more amines having at least one secondary amine group and at least one hydroxyalkyl carbamate group or precursor thereof.

Claim 24

Dependent Claim 76 words

An electrodeposition bath comprising an aqueous dispersion of an acidified, cathodically electrodepositable, self-cross-linkable polymer containing at least two hydroxyalkyl carbamate groups and at least one tertiary amine group per molecule, and obtained as the reaction product of (a) an epoxy resin having an average molecular weight of from about 300 to about 10,000, and (b) one or more amines having at least one secondary amine group and at least one hydroxyalkyl carbamate group or precursor thereof.

Claim 25

Dependent Claim 11 words

The electrodeposition bath of claim 20 further including a cross-linking catalyst.

Claim 26

Dependent Claim 14 words

The electrodeposition bath of claim 21 wherein said catalyst is a suitable quaternary compound.

Claim 27

Dependent Claim 57 words

The electrodeposition bath of claim 20 wherein said epoxy resin is selected from the group consisting of: (i) the reaction product of epichlorohydrin and a polyhydric phenol, (ii) the epoxide of (i) modified by reaction with carboxylate containing polybutadiene polymers, and (iii) the reaction product of epichlorohydrin and a condensation product of phenol with acetone and formaldehyde.

Claim 28

Dependent Claim 20 words

The electrodeposition bath of claim 21 wherein said catalyst is selected from the class consisting of quaternary and ternary compounds.

Claim 29

Dependent Claim 59 words

A method of preparing a cross-linked coating utilizing the electrodeposition bath of claim 24 comprising immersing a substrate in the bath, cathodically electrodepositing a coating of the polymer from the bath onto the substrate, removing the coated substrate from the bath, and heating the coated substrate at a temperature and for a time sufficient to cure the deposited coating.

Claim 30

Dependent Claim 28 words

The method of claim 25 wherein the catalyst is selected from the class consisting of one or more quaternary ammonium, phosphonium and arsonium compounds and ternary sulfonium compounds.

Claim 31

Dependent Claim 13 words

The method of claim 25 wherein the catalyst is a quaternary ammonium compound.

Claim 32

Dependent Claim 33 words

The method of claim 25 wherein the coated substrate is heated to a temperature of from about 200° to about 250° F. (about 93° to about 121° C.) to cure the deposited coating.

Claim 33

Dependent Claim 14 words

The electrodeposition bath of claim 21 wherein said cross-linking catalyst is a metal catalyst.

Claim 34

Dependent Claim 22 words

The electrodeposition bath of claim 29 wherein said metal catalyst is selected from the group consisting of tin, zinc and titanium compounds.

Claim 35

Dependent Claim 12 words

The electrodeposition bath of claim 30 wherein said metal catalyst is dibutyltindilaurate.

Claim 36

Dependent Claim 17 words

The polymer of claim 2 wherein said epoxy resin is the reaction product of bisphenol-A and epichlorohydrin.

Claim 37

Dependent Claim 16 words

The polymer of claim 12 wherein said epoxide is the reaction product of bisphenol-A and epichlorohydrin.

Claim 38

Dependent Claim 18 words

The electrodeposition bath of claim 20 wherein said epoxy resin is the reaction product of bisphenol-A and epichlorohydrin.

Claim 39

Dependent Claim 13 words

The polymer of claim 14 wherein R 3 contains one or more heteroatoms.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1987-11-27	1988-05-28	1988-11-27	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1991-11-27	1992-05-28	1992-11-27	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	1995-11-27	1996-05-28	1996-11-27	$7700.00	Window Closed / Lapsed

Hydroxyalkyl carbamate-containing resins for cathodic electrodeposition and method of making the same

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