Additives for coating compositions and related methods

Patent metadata

Field	Value
Publication number	US-10934439-B2
Application number	US-201816016004-A
Country	US
Kind code	B2
Filing date	Jun 22, 2018
Priority date	Jun 22, 2017
Publication date	Mar 2, 2021
Grant date	Mar 2, 2021

Abstract

Disclosed are curable coating compositions, and methods of cathodic corrosion protection using the compositions. For example, a curable coating composition comprising a mixed salt of magnesium thiodialkanoate, and a method for applying the coating composition, which when applied onto a steel or other ferrous substrate provides an anticorrosive coating, effective for improving resistance to cathodic disbondment.

First claim

We claim:

1. A curable coating composition, comprising:
(a) a salt comprising a divalent alkaline earth metal cation and an anionic thioether compound;
(b) a curing agent or a mixture of curing agents; and
(c) one or more curable organic resin,
wherein the salt has the following structural formula:

wherein R is selected from the group consisting of divalent (C 1 -C 6 )alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, and (C 2 -C 6 )alkenyl;
R 1 is selected from the group consisting of divalent (C 1 -C 6 )alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, and (C 2 -C 6 )alkenyl;
R 2 is hydrogen or (C 1 -C 20 )alkyl; and
X is selected from the group consisting of H, halogen, (C 1 -C 20 )alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, (C 2 -C 20 )alkenyl, —OR 2 , —SR 2 , —N(R 2 ) 2 , —C(O)N(R 2 ) 2 , —C(O)N(R 2 )((C 1 -C 20 )alkylene)N(R 2 ) 2 , and —C(O)R 2 , or
the following structural formula:

wherein
R is selected from the group consisting of divalent (C 1 -C 6 )alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, and (C 2 -C 6 )alkenyl,
R 1 is selected from the group consisting of divalent (C 1 -C 6 )alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, and (C 2 -C 6 )alkenyl;
R 2 is hydrogen or (C 1 -C 20 )alkyl;
X is absent or selected from the group consisting of H, halogen, (C 1 -C 20 )alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, (C 2 -C 20 )alkenyl, —OR 2 , —SR 2 , —N(R 2 ) 2 , —C(O)N(R 2 ) 2 , —C(O)N(R 2 )((C 1 -C 20 )alkylene)N(R 2 ) 2 , and —C(O)R 2 ; and
n is 1 or 2.

2. The composition of claim 1 , wherein the ratio of the divalent alkaline earth metal cation to the anionic thioether compound is from about 50:1 to about 0.1:1.

3. The composition of claim 1 , wherein the salt is from about 0.1% to about 80% by weight, based upon total solids weight of the composition.

4. The composition of claim 1 , wherein the salt has the following structural formula:

wherein
R is selected from the group consisting of divalent (C 1 -C 6 )alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, and (C 2 -C 6 )alkenyl;
R 1 is selected from the group consisting of divalent (C 1 -C 6 )alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, and (C 2 -C 6 )alkenyl;
R 2 is hydrogen or (C 1 -C 20 )alkyl; and
X is selected from the group consisting of H, halogen, (C 1 -C 20 )alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, (C 2 -C 20 )alkenyl, —OR 2 , —SR 2 , —N(R 2 ) 2 , —C(O)N(R 2 ) 2 , —C(O)N(R 2 )((C 1 -C 20 )alkylene)N(R 2 ) 2 , and —C(O)R 2 .

5. The composition of claim 1 , wherein the salt has the following structural formula:

wherein
R is selected from the group consisting of divalent (C 1 -C 6 )alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, and (C 2 -C 6 )alkenyl;
R 1 is selected from the group consisting of divalent (C 1 -C 6 )alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, and (C 2 -C 6 )alkenyl;
R 2 is hydrogen or (C 1 -C 20 )alkyl;
X is absent or selected from the group consisting of H, halogen, (C 1 -C 20 )alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, (C 2 -C 20 )alkenyl, —OR 2 , —SR 2 , —N(R 2 ) 2 , —C(O)N(R 2 ) 2 , —C(O)N(R 2 )((C 1 -C 20 )alkylene)N(R 2 ) 2 , and —C(O)R 2 ; and
n is 1 or 2.

6. The composition of claim 1 , wherein the curing agent or the mixture of curing agents comprises an amine, an amido-amine, a phenol, a carboxylic anhydride, or a mercaptan.

7. The composition of claim 1 , wherein the one or more curable organic resins comprise a bisphenol A epoxy resin, bisphenol A propoxylate diglycidyl ether, or N 4 ,N 4 ,N 4 ′,N 4 ′-tetra(oxiran-2-yl)-[1,1′-biphenyl]-4,4′-diamine.

8. The composition of claim 1 , further comprising an additive.

9. The composition of claim 8 , wherein the additive is selected from the group consisting of a dye, a flow control agent, a dispersant, a thixotropic agent, an adhesion promoter, an antioxidant, a light stabilizer, a curing catalyst, an anticorrosion agent, and a mixture thereof.

10. The composition of claim 1 , further comprising:
(i) a pigment; or
(ii) an additive.

11. The composition of claim 10 , wherein the composition comprises a pigment selected from the group consisting of carbon nanotubes, titanium dioxide, montmorillonite, iron oxide, aluminum, bronze, phthalocyanine blue, and a mixture thereof.

12. A method of preventing or reducing corrosion on a surface, comprising applying to the surface a coating, wherein the coating is a curable coating composition comprising:
(a) a salt comprising a divalent alkaline earth metal cation and an anionic thioether compound;
(b) a curing agent or a mixture of curing agents; and
(c) one or more curable organic resins,
wherein the salt has the following structural formula:

wherein R is selected from the group consisting of divalent (C 1 -C 6 )alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, and (C 2 -C 6 )alkenyl;
R 1 is selected from the group consisting of divalent (C 1 -C 6 )alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, and (C 2 -C 6 )alkenyl;
R 2 is hydrogen or (C 1 -C 20 )alkyl; and
X is selected from the group consisting of H, halogen, (C 1 -C 20 )alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, (C 2 -C 20 )alkenyl, —OR 2 , —SR 2 , —N(R 2 ) 2 , —C(O)N(R 2 ) 2 , —C(O)N(R 2 )((C 1 -C 20 )alkylene)N(R 2 ) 2 , and —C(O)R 2 , or
the following structural formula:

wherein
R is selected from the group consisting of divalent (C 1 -C 6 )alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, and (C 2 -C 6 )alkenyl;
R 1 is selected from the group consisting of divalent (C 1 -C 6 )alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, and (C 2 -C 6 )alkenyl;
R 2 is hydrogen or (C 1 -C 20 )alkyl;
X is absent or selected from the group consisting of H, halogen, (C 1 -C 20 )alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, (C 2 -C 20 )alkenyl, —OR 2 , —SR 2 , —N(R 2 ) 2 , —C(O)N(R 2 ) 2 , —C(O)N(R 2 )((C 1 -C 20 )alkylene)N(R 2 ) 2 , and —C(O)R 2 ; and
(d) n is 1 or 2;

thereby preventing or reducing corrosion of the surface.

13. The method of claim 12 , wherein the salt has the following structural formula:

wherein
R is selected from the group consisting of divalent (C 1 -C 6 )alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, and (C 2 -C 6 )alkenyl;
R 1 i

Assignees

• Massachusetts Inst Technology

Inventors

• Hatton T Alan
• Bromberg Lev E

Classifications

• C23F11/162

  Thioaldehydes; Thioketones · CPC title

• C08G59/4064

  sulfur containing compounds (C08G59/4021, C08G59/4028 take precedence) · CPC title

• C23F11/124

  Carboxylic acids · CPC title

• C08G59/687

  containing sulfur · CPC title

• C09D7/60

  non-macromolecular (C09D7/41-C09D7/48 take precedence) · CPC title