Curable coating compositions of silane functional polymers
First Claim
Patent Images
1. A tin-free curable composition, comprising:
- (A) one or more organic polymers having a reactive-silicon-containing group, wherein at least one polymer has a main chain skeleton selected from the group consisting of polyoxyalkylene polymers, saturated hydrocarbon polymers, and (meth)acrylic acid ester polymers;
(B) from 0.001 to 20 parts by weight for 100 parts by weight of the organic polymer(s) (A) of a silanol condensation catalyst consisting of one or more metal amidine complexes and one or more amine carboxylate salts,(C) a crosslinker or chain extender chosen from an alkoxylate, an alkoxysiloxane, an oximosilane, an oximosiloxane, an epoxysilane, an epoxysiloxane, an aminosilane, a carboxysilane, a carboxysiloxane, an alkylamidosilane, an alkylamidosiloxane, an arylamidosilane, an arylamidosiloxane, an alkoxyaminosilane, an alkaryaminosiloxane, an alkoxycarbamatosilane, an alkoxycarbamatosiloxane, and combinations of two or more thereof;
(D) at least one adhesion promoter chosen from a silane or siloxane other than the compounds listed under (C);
(E) optionally, a filler component; and
(F) optionally, at least one acidic compound chosen from a phosphate ester, a phosphonate, a phosphite, a phosphine, a sulfite, a pseudohalogenide, a branched alkyl carboxylic acid, and a combination of two or more thereof;
wherein at least one part of the reactive-silicon-containing group(s) of the organic polymer(s) (A) is represented by general formula I
—
(CR22)2—
(SiR12-aXa)m—
SiX3 wherein each R1 independently represents a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, or a triorganosiloxy group represented by (R′
)3SiO—
wherein R′
s are each a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, and R′
s may be the same or different, each R2 are independently a hydrogen atom, or a substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms, each X are independently a hydroxyl group, or a hydrolyzable group, a is 0, 1 or 2, and m is 0 or an integer of from 1 to 19,or general formula
[R11bR123-bSi—
Z—
]n—
X′
—
Z—
SiR11bR123-b wherein X′
is chosen from a polyurethane;
a polyester;
a polyether;
a polycarbonate, a polyolefin, a polypropylene, a polyesterether; and
a polyorganosiloxane having units of R3SiO1/2, R2SiO, RSiO3/2, and/or SiO4/2, n is 0 to 100, b is 0 to 2, R and R11 can be identical or different at the same Si-atom and chosen from a C1-C10-alkyl, a C1-C10 alkyl substituted with one or more of CI, F, N, O or S, a phenyl, a C7-C16 alkylaryl, a C7-C16 arylalkyl, a C2-C4 polyalkylene ether, or a combination of two or more thereof, R12 is chosen from OH, a C1-C8-alkoxy, a C2-C18-alkoxyalkyl, an oximoalkyl, an enoxyalkyl, an aminoalkyl, a carboxyalkyl, an amidoalkyl, an amidoaryl, a carbamatoalkyl, or a combination of two or more thereof, and Z is a bond, a divalent unit selected from the group of a C1-C8 alkylene, or O;
wherein the one or more amine carboxylate salts is derived from a phenyl guanidine represented by formulae
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Abstract
There is a tin-free curable composition having (A) one or more organic polymers having a reactive-silicon-containing group, wherein at least one polymer has a main chain skeleton selected from the group consisting of polyoxyalkylene polymers, saturated hydrocarbon polymers, and (meth)acrylic acid ester polymers; (B) from 0.001 to 20 parts by weight for 100 parts by weight of the organic polymer(s) (A) of a silanol condensation catalyst consisting of one or more metal amidine complexes and one or more amine carboxylate salts, (C) a crosslinker or chain extender chosen from an alkoxysilane, an alkoxysiloxane, an oximosilane, an oximosiloxane, an epoxysilane, an epoxysiloxane, an aminosilane, a carboxysilane, a carboxysiloxane, an alkylamidosilane, an alkylamidosiloxane, an arylamidosilane, an arylamidosiloxane, an alkoxyaminosilane, an alkaryaminosiloxane, an alkoxycarbamatosilane, an alkoxycarbamatosiloxane, and combinations of two or more thereof; and (D) at least one adhesion promoter chosen from a silane or siloxane other than the compounds listed under (C). There is also a cured polymer formed from the tin-free curable composition.
56 Citations
74 Claims
-
1. A tin-free curable composition, comprising:
-
(A) one or more organic polymers having a reactive-silicon-containing group, wherein at least one polymer has a main chain skeleton selected from the group consisting of polyoxyalkylene polymers, saturated hydrocarbon polymers, and (meth)acrylic acid ester polymers; (B) from 0.001 to 20 parts by weight for 100 parts by weight of the organic polymer(s) (A) of a silanol condensation catalyst consisting of one or more metal amidine complexes and one or more amine carboxylate salts, (C) a crosslinker or chain extender chosen from an alkoxylate, an alkoxysiloxane, an oximosilane, an oximosiloxane, an epoxysilane, an epoxysiloxane, an aminosilane, a carboxysilane, a carboxysiloxane, an alkylamidosilane, an alkylamidosiloxane, an arylamidosilane, an arylamidosiloxane, an alkoxyaminosilane, an alkaryaminosiloxane, an alkoxycarbamatosilane, an alkoxycarbamatosiloxane, and combinations of two or more thereof; (D) at least one adhesion promoter chosen from a silane or siloxane other than the compounds listed under (C); (E) optionally, a filler component; and (F) optionally, at least one acidic compound chosen from a phosphate ester, a phosphonate, a phosphite, a phosphine, a sulfite, a pseudohalogenide, a branched alkyl carboxylic acid, and a combination of two or more thereof; wherein at least one part of the reactive-silicon-containing group(s) of the organic polymer(s) (A) is represented by general formula I
—
(CR22)2—
(SiR12-aXa)m—
SiX3wherein each R1 independently represents a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, or a triorganosiloxy group represented by (R′
)3SiO—
wherein R′
s are each a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, and R′
s may be the same or different, each R2 are independently a hydrogen atom, or a substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms, each X are independently a hydroxyl group, or a hydrolyzable group, a is 0, 1 or 2, and m is 0 or an integer of from 1 to 19,or general formula
[R11bR123-bSi—
Z—
]n—
X′
—
Z—
SiR11bR123-bwherein X′
is chosen from a polyurethane;
a polyester;
a polyether;
a polycarbonate, a polyolefin, a polypropylene, a polyesterether; and
a polyorganosiloxane having units of R3SiO1/2, R2SiO, RSiO3/2, and/or SiO4/2, n is 0 to 100, b is 0 to 2, R and R11 can be identical or different at the same Si-atom and chosen from a C1-C10-alkyl, a C1-C10 alkyl substituted with one or more of CI, F, N, O or S, a phenyl, a C7-C16 alkylaryl, a C7-C16 arylalkyl, a C2-C4 polyalkylene ether, or a combination of two or more thereof, R12 is chosen from OH, a C1-C8-alkoxy, a C2-C18-alkoxyalkyl, an oximoalkyl, an enoxyalkyl, an aminoalkyl, a carboxyalkyl, an amidoalkyl, an amidoaryl, a carbamatoalkyl, or a combination of two or more thereof, and Z is a bond, a divalent unit selected from the group of a C1-C8 alkylene, or O;wherein the one or more amine carboxylate salts is derived from a phenyl guanidine represented by formulae - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28)
-
-
29. A tin-free curable composition, comprising:
-
(A) one or more organic polymers having a reactive-silicon-containing group, wherein at least one polymer has a main chain skeleton selected from the group consisting of polyoxyalkylene polymers, saturated hydrocarbon polymers, and (meth)acrylic acid ester polymers; (B) from 0.001 to 20 parts by weight for 100 parts by weight of the organic polymer(s) (A) of a silanol condensation catalyst consisting of one or more metal amidine complexes and one or more amine carboxylate salts, (C) a crosslinker or chain extender chosen from an alkoxylate, an alkoxysiloxane, an oximosilane, an oximosiloxane, an epoxysilane, an epoxysiloxane, an aminosilane, a carboxysilane, a carboxysiloxane, an alkylamidosilane, an alkylamidosiloxane, an arylamidosilane, an arylamidosiloxane, an alkoxyaminosilane, an alkaryaminosiloxane, an alkoxycarbamatosilane, an alkoxycarbamatosiloxane, and combinations of two or more thereof; (D) at least one adhesion promoter chosen from a silane or siloxane other than the compounds listed under (C); (E) optionally, a filler component; and (F) optionally, at least one acidic compound chosen from a phosphate ester, a phosphonate, a phosphite, a phosphine, a sulfite, a pseudohalogenide, a branched alkyl carboxylic acid, and a combination of two or more thereof; wherein at least one part of the reactive-silicon-containing group(s) of the organic polymer(s) (A) is represented by general formula I
—
(CR22)2—
(SiR12-aXa)m—
SiX3wherein each R1 independently represents a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, or a triorganosiloxy group represented by (R′
)3SiO—
wherein R′
s are each a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, and R′
s may be the same or different, each R2 are independently a hydrogen atom, or a substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms, each X are independently a hydroxyl group, or a hydrolyzable group, a is 0, 1 or 2, and m is 0 or an integer of from 1 to 19,or general formula
[R11bR123-bSi—
Z—
]nX′
—
Z—
SiR11bR123-bwherein X′
is chosen from a polyurethane;
a polyester;
a polyether;
a polycarbonate, a polyolefin, a polypropylene, a polyesterether; and
a polyorganosiloxane having units of R3SiO1/2, R2SiO, RSiO3/2, and/or SiO4/2, n is 0 to 100, b is 0 to 2, R and R11 can be identical or different at the same Si-atom and chosen from a C1-C10-alkyl, a C1-C10 alkyl substituted with one or more of CI, F, N, O or S, a phenyl, a C7-C16 alkylaryl, a C7-C16 arylalkyl, a C2-C4 polyalkylene ether, or a combination of two or more thereof, R12 is chosen from OH, a C1-C8-alkoxy, a C2-C18-alkoxyalkyl, an oximoalkyl, an enoxyalkyl, an aminoalkyl, a carboxyalkyl, an amidoalkyl, an amidoaryl, a carbamatoalkyl, or a combination of two or more thereof, and Z is a bond, a divalent unit selected from the group of a C1-C8 alkylene, or O;wherein the one or more amine carboxylate salts is derived from an amine compound selected from monoethanolamine, 3-hydroxypropylamine, 2-(2-aminoethylamino)ethanol, 1-dimethylamino-2-propanol, diethylamino-2-propanol, 2-(dimethylam ino)ethanol, 2-(diethylamino)ethanol, 2-dimethylamino-2-methyl-1-propanol, ethylenediamine, N-methylethylenediamine, 1,3-propanediamine, N-methyl-1,3-propanediam ine, N,N′
-dimethyl-1,3-propanediamine, 3-(diethylamino)propyl amine, 3-(dimethylam ino)propyl amine and diethylenetriamine. - View Dependent Claims (30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51)
-
-
52. A tin-free curable composition, comprising:
-
(A) one or more organic polymers having a reactive-silicon-containing group, wherein at least one polymer has a main chain skeleton selected from the group consisting of polyoxyalkylene polymers, saturated hydrocarbon polymers, and (meth)acrylic acid ester polymers; (B) from 0.001 to 20 parts by weight for 100 parts by weight of the organic polymer(s) (A) of a silanol condensation catalyst consisting of one or more metal amidine complexes and one or more amine carboxylate salts, (C) a crosslinker or chain extender chosen from an alkoxylate, an alkoxysiloxane, an oximosilane, an oximosiloxane, an epoxysilane, an epoxysiloxane, an aminosilane, a carboxysilane, a carboxysiloxane, an alkylamidosilane, an alkylamidosiloxane, an arylamidosilane, an arylamidosiloxane, an alkoxyaminosilane, an alkaryaminosiloxane, an alkoxycarbamatosilane, an alkoxycarbamatosiloxane, and combinations of two or more thereof; (D) at least one adhesion promoter chosen from a silane or siloxane other than the compounds listed under (C); (E) optionally, a filler component; and (F) optionally, at least one acidic compound chosen from a phosphate ester, a phosphonate, a phosphite, a phosphine, a sulfite, a pseudohalogenide, a branched alkyl carboxylic acid, and a combination of two or more thereof; wherein at least one part of the reactive-silicon-containing group(s) of the organic polymer(s) (A) is represented by general formula I
—
(CR22)2—
(SiR12-aXa)m—
SiX3wherein each R1 independently represents a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, or a triorganosiloxy group represented by (R′
)3SiO—
wherein R′
s are each a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, and R′
s may be the same or different, each R2 are independently a hydrogen atom, or a substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms, each X are independently a hydroxyl group, or a hydrolyzable group, a is 0, 1 or 2, and m is 0 or an integer of from 1 to 19,or general formula
[R11bR123-bSi—
Z—
]n—
X′
—
Z—
SiR11bR123-bwherein X′
is chosen from a polyurethane;
a polyester;
a polyether;
a polycarbonate, a polyolefin, a polypropylene, a polyesterether; and
a polyorganosiloxane having units of R3SiO1/2, R2SiO, RSiO3/2, and/or SiO4/2, n is 0 to 100, b is 0 to 2, R and R11 can be identical or different at the same Si-atom and chosen from a C1-C10-alkyl, a C1-C10 alkyl substituted with one or more of CI, F, N, O or S, a phenyl, a C7-C16 alkylaryl, a C7-C16 arylalkyl, a C2-C4 polyalkylene ether, or a combination of two or more thereof, R12 is chosen from OH, a C1-C8-alkoxy, a C2-C18-alkoxyalkyl, an oximoalkyl, an enoxyalkyl, an aminoalkyl, a carboxyalkyl, an amidoalkyl, an amidoaryl, a carbamatoalkyl, or a combination of two or more thereof, and Z is a bond, a divalent unit selected from the group of a C1-C8 alkylene, or O;wherein the one or more amine carboxylate salts is derived from a carboxylic acid in which the α
-carbon atom of the carboxyl group is a quaternary carbon atom. - View Dependent Claims (53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74)
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Specification
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Current AssigneeKing Industries
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Original AssigneeKing Industries
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InventorsRavichandran, Ramanathan, Florio, John, Hsieh, Bing, Switala, David P.
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Primary Examiner(s)PEPITONE, MICHAEL F
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Application NumberUS15/049,846Publication NumberTime in Patent Office820 DaysField of SearchUS Class CurrentCPC Class CodesC08G 2261/76 crosslinkingC08K 3/28 Nitrogen-containing compoundsC08K 5/0091 Complexes with metal-hetero...C08K 5/175 containing COOH-groups; Est...C08K 5/29 Compounds containing one or...C08K 5/5419 containing at least one Si—...C08K 5/544 containing nitrogenC08K 5/5475 containing at least one C≡N...C08L 67/00 Compositions of polyesters ...C08L 77/04 Polyamides derived from alp...C08L 77/12 Polyester-amidesC09J 167/00 Adhesives based on polyeste...
