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US 8,575,292 B2Granted
Hydroxyl-functional carbamoyl organosilicon compounds of low VOC and HAP generating potential, anti-corrosion and/or adhesion promoting coating composition containing same, environmentally benign method of coating metal therewith and resulting coated metal
AssigneeMomentive Performance Materials Inc.
InventorsShiu-Chin H. Su, Suresh K. Rajaraman, Alexander S. Borovik, Kendall L. Guyer, Eric R. Pohl
Life of this patent
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Abstract
There is provided a hydroxyl-functional carbamoyl organosilicon compound, an anti-corrosion and/or adhesion promoting coating composition based thereon, a method for coating a metal surface employing the coating composition and the resulting coated metal article.
Claims34
A hydroxyl-functional carbamoyl organosilicon compound which possesses:
- (i) at least one hydroxyl group bonded to a carbon atom and at least one carbamoyl group covalently bonded to a silicon atom through a silicon-carbon bond, and
- (ii) at least one divalent oxygen-containing group possessing at least two silyloxy bonds, wherein the hydroxyl-functional carbamoyl organosilicon compound is represented by the Formula (1):
- wherein:
- each occurrence of R1, R2 and R3 is independently a divalent hydrocarbylene group, optionally containing one or more etheric oxygen atoms;
- each occurrence of R4 is independently hydrogen, a hydrocarbyl group, an —R1SiX1aZbbZcc group or a —C(═O)OR6(OH)f group where R6 is independently a divalent or polyvalent hydrocarbylene group;
- each occurrence of R5 is independently hydrogen, a hydrocarbyl group or an —R1SiXlaZbbZcc group;
- each occurrence of X1 is independently —Cl, —Br, R7O—, R7C(═O)O—, R72C═NO—, R72NO—, R72N—, —R7, or (HO)h-1R8O— wherein each R7 is independently hydrogen or a hydrocarbyl group and each R8 is independently a divalent or polyvalent hydrocarbylene group, optionally containing one or more etheric oxygen atoms;
- each occurrence of Zb is independently [—OR9(OH)i-2O—]0.5 wherein each occurrence of R9 is independently a divalent or polyvalent hydrocarbylene group, optionally containing one or more etheric oxygen atoms, and where [—OR9(OH)i-2O—]0.5 refers to one-half of a bridging dialkoxy group;
- each occurrence of Zc is independently a —OR10(OH)j-2O— group wherein R10 is independently a divalent or polyvalent hydrocarbylene group, optionally containing one or more etheric oxygen atoms;
- and,
- subscripts a, b, c, d, e, f, g and h are integers wherein a is 0 to 2;
- b is 0 to 3;
- c is 0 or 1;
- d is 1 to 4;
- e is 0 to 20, f is 1 to 4;
- g is 1 to 100;
- h is 2 to 3;
- i is 2 to 3 and j is 2 to 3, provided, when c is 1, a+b is 1;
- and when b is 0, then g is 1 and c is 1, wherein said hydroxyl-functional carbamoyl organosilicon compound is selected from the group consisting of [3-(2-ethoxy-5-methyl-[1,3,2]dioxasilinan-2-yl)-propyl]-carbamic acid 2-hydroxy-ethyl ester;
- {3-[2-(3-hydroxy-2-methyl-propoxy)-5-methyl-[1,3,2]dioxasilinan-2-yl]-propyl}-carbamic acid 2-hydroxy-ethyl ester;
- [3-(2-ethoxy-5-methyl-[1,3]dioxan-2-yl)-propyl]-[3-(2-ethoxy-5-methyl-[1,3,2]dioxasilinan-2-yl)-propyl]-carbamic acid 2-hydroxy-ethyl ester;
- [3-(2,4,4,6-tetramethyl-[1,3]dioxan-2-yl)-propyl]-[3-(2,4,4,6-tetramethyl-[1,3,2]dioxasilinan-2-yl)-propyl]-carbamic acid 2-hydroxy-ethyl ester;
- [3-(2,4,4,6-tetramethyl-[1,3]dioxan-2-yl)-propyl]-{[3-(2,4,4,6-tetramethyl-[1,3,2]dioxasilinan-2-yl)-propylamino]-methyl}-carbamic acid 2-hydroxy-ethyl ester;
- ({(2-hydroxy-ethoxycarbonyl)-[3-(2,4,4,6-tetramethyl-[1,3]dioxan-2-yl)-propyl]-amino}-methyl)-[3-(2,4,4,6-tetramethyl-[1,3,2]dioxasilinan-2-yl)-propyl]-carbamic acid 2-hydroxy-ethyl ester;
- ({(2,3-dihydroxy-propoxycarbonyl)-[3-(2,4,4,6-tetramethyl-[1,3]dioxan-2-yl)-propyl]-amino}-methyl)-[3-(2,4,4,6-tetramethyl-[1,3,2]dioxasilinan-2-yl)-propyl]-carbamic acid 2,3-dihydroxy-propyl ester;
- [3-(2,4-dimethyl-[1,3,2]dioxasilinan-2-yl)-propyl]-{[[3-(2,4-dimethyl-[1,3,2]dioxasilinan-2-yl)-propyl]-(2-hydroxy-1-methyl-ethoxycarbonyl)-amino]-methyl}-carbamic acid 3-hydroxy-1-methyl-propyl ester;
- [3-(2,4-dimethyl-[1,3,2]dioxasilinan-2-yl)-propyl]-{[[3-(2,4-dimethyl-[1,3,2]dioxasilinan-2-yl)-propyl]-(2-hydroxy-1-methyl-ethoxycarbonyl)-amino]-methyl}-carbamic acid 3-hydroxy-1-methyl-propyl ester;
- [4-(2-ethoxy-4-methyl-[1,3,2]dioxasilinan-2-yl)-butyl]-[3-(2-ethoxy-4-methyl-[1,3,2]dioxasilinan-2-yl)-propyl]-carbamic acid 3-hydroxy-1-hydroxymethyl-propyl ester;
- {3-[2-(3-{2-[3-(2-hydroxy-ethoxycarbonylamino)-propyl]-[1,3,2]dioxasilinan-2-yloxy}-propoxy)-[1,3,2]dioxasilinan-2-yl]-propyl}-carbamic acid 3-hydroxy-propyl ester;
- {3-[bis-(3-{2-[3-(2-hydroxy-ethoxycarbonylamino)-propyl]-[1,3,2]dioxasilinan-2-yloxy}-propoxy)-3-hydroxypropoxy-silanyl]-propyl}-carbamic acid 3-hydroxy-propyl ester;
- {3-[{3-[[3-(2-hydroxy-ethoxycarbonylamino)-propyl]-(3-hydroxy-propoxy)-methyl-silanyloxy]-propoxy}-(3-hydroxy-propoxy)-methyl-silanyl]-propyl}-carbamic acid 2-hydroxy-ethyl ester;
- {[ethyl-{3-[ethyl-[(2-hydroxy-ethoxycarbonylamino)-methyl]-(3-hydroxy-propoxy)-silanyloxy]-propoxy}-(3-hydroxy-propoxy)-silanyl]-methyl}-carbamic acid 2-hydroxy-ethyl ester;
- {3-[(2-hydroxy-ethoxycarbonylamino)-methyl]-1,1,3,3-tetrahydroxy-disiloxanylmethyl}-carbamic acid 2-hydroxy-ethyl ester;
- and
- {3-[(2-hydroxy-ethoxycarbonylamino)-methyl]-1,1,3,3-tetramethyl-disiloxanylmethyl}-carbamic acid 2-hydroxy-ethyl ester.
32 more elements
A method for coating at least a portion of the exposed surface of a metal which comprises:
- a) applying to said surface a curable coating composition comprising an aqueous solution of at least one partially or substantially completely hydrolyzed hydroxyl-functional carbamoyl organosilicon compound which possesses:
- (i) at least one hydroxyl group bonded to a carbon atom and at least one carbamoyl group covalently bonded to a silicon atom through a silicon-carbon bond, and
- (ii) at least one divalent oxygen-containing group possessing at least two silyloxy bonds, wherein the hydroxyl-functional carbamoyl organosilicon compound is represented by the Formula (1):
- wherein:
- each occurrence of R1, R2 and R3 is independently a divalent hydrocarbylene group, optionally containing one or more etheric oxygen atoms;
- each occurrence of R4 is independently hydrogen, a hydrocarbyl group, an —R1SiX1aZbbZcc group or a —C(═O)OR6(OH)f group where R6 is independently a divalent or polyvalent hydrocarbylene group;
- each occurrence of R5 is independently hydrogen, a hydrocarbyl group or an —R1SiX1aZbbZcc group;
- each occurrence of X1 is independently —Cl, —Br, R7O—, R7C(═O)O—, R72C═NO—, R72NO—, R72N—, —R7, or (HO)h-1R8O— wherein each R7 is independently hydrogen or a hydrocarbyl group and each R8 is independently a divalent or polyvalent hydrocarbylene group, optionally containing one or more etheric oxygen atoms;
- each occurrence of Zb is independently [—OR9(OH)i-2O—]0.5 wherein each occurrence of R9 is independently a divalent or polyvalent hydrocarbylene group, optionally containing one or more etheric oxygen atoms, and where [—OR9(OH)i-2O—]0.5 refers to one-half of a bridging dialkoxy group;
- each occurrence of Zc is independently a —OR10(OH)j-2O— group wherein R10 is independently a divalent or polyvalent hydrocarbylene group, optionally containing one or more etheric oxygen atoms;
- and,
- subscripts a, b, c, d, e, f, g and h are integers wherein a is 0 to 2;
- b is 0 to 3;
- c is 0 or 1;
- d is 1 to 4;
- e is 0 to 20, f is 1 to 4;
- g is 1 to 100;
- h is 2 to 3;
- i is 2 to 3 and j is 2 to 3, provided, when c is 1, a+b is 1;
- and when b is 0, then g is 1 and c is 1;
- and,
- b) curing the curable coating composition on the surface of the metal to provide an anti-corrosion and/or adhesion promoting coating thereon.
19 more elements
Dependencies are inferred from the claim text.