US 6,592,999 B1 · Multi-layer composites formed from compositions having improved adhesion, coating compositions, and methods related thereto

In a multi-layer composite of two or more polymeric layers, at least one of which is formed from a thermosetting composition, said composite comprising at least a first polymeric layer formed on a substrate and a second polymeric layer formed over at least a portion of said first polymeric layer, wherein in the absence of a boron-containing compound, said first polymeric layer and said second polymeric layer have poor interlayer adhesion,

the improvement comprising the inclusion of at least one boron-containing compound in one or both of said first and second polymeric layers in an amount sufficient to improve the interlayer adhesion of said first polymeric layer and said second polymeric layer, wherein said boron-containing compound comprises a boric acid ester derivative selected from at least one of triethanolamineborate, mannitol borate, n-propanol amine borate, trimethyolpropane borate, glycerol borate, and mixtures thereof.

In a multi-layer composite of two or more polymeric layers, at least one of which is formed from a thermosetting composition, said composite comprising at least a first polymeric layer formed on a substrate and a second polymeric layer formed over at least a portion of said first polymeric layer, wherein in the absence of a boron-containing compound, said first polymeric layer and said second polymeric layer have poor interlayer adhesion,

the improvement comprising the inclusion of at least one boron-containing compound in one or both of said first and second polymeric layers in an amount sufficient to improve the interlayer adhesion of said first polymeric layer and said second polymeric layer, wherein said boron-containing compound comprises the reaction product formed from the following reactants:
(A) at least one polysiloxane comprising at least one of the following structural units (I):
R1nR2mSiO(4−n−m)/2 (I)
wherein each R1, which may be identical or different, represents H, OH, a monovalent hydrocarbon group or a monovalent siloxane group;
each R2, which may be identical or different, represents a group comprising one or more active hydrogens;
and m and n each represent a positive number fulfilling the requirements of 0<m<4;
0<n<4;
and 2≦(m+n)<4;
and
(B) a boron-containing compound selected from at least one of boric acid, boric acid equivalents, and mixtures thereof.

7 more elements

In a curable coating composition used to form a multi-layer composite coating comprising two or more cured coating layers, said multi-layer composite coating comprising at least a first coating layer formed on a substrate and a second coating layer over at least a portion of said first polymeric layer, wherein one or both of said first coating layer and said second coating layer are formed from said curable coating composition, and wherein in the absence of a boron-containing compound, said first coating layer and said second coating layer have poor interlayer adhesion,

the improvement comprising the inclusion in said curable coating composition of a boron-containing compound in an amount sufficient to improve the interlayer adhesion between said first coating layer and said second coating layer, wherein said boron-containing compound comprises the reaction product of the following reactants:
(A) at least one polysiloxane comprising at least one of the following structural units (I):
R1nR2mSiO(4−n−m)/2 (I)
wherein each R1, which may be identical or different, represents H, OH, a monovalent hydrocarbon group or a monovalent siloxane group;
each R2, which may be identical or different, represents a group comprising one or more active hydrogens;
and m and n each represent a positive number fulfilling the requirements of 0<m<4;
0<n<4;
and 2≦(m+n)<4;
and
(B) at least one boron-containing compound selected from at least one of boric acid, boric acid equivalents, and mixtures thereof.

7 more elements

In a curable coating composition used to form a multi-layer composite coating comprising two or more cured coating layers, said multi-layer composite coating comprising at least a first coating layer formed on a substrate and a second coating layer over at least a portion of said first polymeric layer, wherein one or both of said first coating layer and said second coating layer are formed from said curable coating composition, and wherein in the absence of a boron-containing compound, said first coating layer and said second coating layer have poor interlayer adhesion,

the improvement comprising the inclusion in said curable coating composition of a boron-containing compound selected from at least one of boric acid, boric acid equivalents, and mixtures thereof in an amount sufficient to improve the interlayer adhesion between said first coating layer and said second coating layer,
wherein one or both of said first coating layer and said second coating layer comprises a cured coating layer formed from a curable coating composition comprising:
(A) at least one acrylic film-forming polymer having reactive functional groups selected from hydroxyl groups, carbamate groups and mixtures thereof, the acrylic film-forming polymer comprising residues of a beta-hydroxy group containing monomer selected from at least one of:
(i) the reaction product of an ethylenically unsaturated acid functional monomer and an epoxy functional compound having no ethylenic unsaturation;
and
(ii) the reaction product of an ethylenically unsaturated, epoxy functional monomer and a saturated carboxylic acid;
(B) at least one curing agent having functional groups reactive with the functional groups of (A) selected from aminoplast resins, polyisocyanates, blocked polyisocyanates and mixtures thereof;
and
(C) at least one boron-containing compound selected from at least one of boric acid, boric acid equivalents, and mixtures thereof.

6 more elements

In a curable coating composition used to form a multi-layer composite coating comprising two or more cured coating layers, said multi-layer composite coating comprising at least a first coating layer formed on a substrate and a second coating layer over at least a portion of said first polymeric layer, wherein one or both of said first coating layer and said second coating layer are formed from said curable coating composition, and wherein in the absence of a boron-containing compound, said first coating layer and said second coating layer have poor interlayer adhesion,

the improvement comprising the inclusion in said curable coating composition of a boron-containing compound selected from at least one of boric acid, boric acid equivalents, and mixtures thereof in an amount sufficient to improve the interlayer adhesion between said first coating layer and said second coating layer,
wherein said first coating layer is formed from a cured coating layer formed from a curable coating composition comprising:
(A) at least one film-forming acrylic polymer comprising functional groups selected from hydroxyl groups, carbamate groups and mixtures thereof;
(B) at least one curing agent selected from aminoplast resins, polyisocyanates, blocked polyisocyanates and mixtures thereof comprising an aminoplast resin and a blocked polyisocyanate comprising a tricarbamoyl triazine compound;
and
(C) at least one boron-containing compound selected from boric acid, boric acid equivalents, and mixtures thereof;
and said second coating layer comprises a cured coating layer formed from a curable coating composition comprising:
(D) at least one film-forming polymer having reactive functional groups selected from hydroxyl groups, carbamate groups and mixtures thereof;
(E) at least one curing agent comprising functional groups reactive with the functional groups of (A);
and
(F) at least one boron-containing compound selected from at least one of boric acid, boric acid equivalents, and mixtures thereof.

8 more elements

In a curable coating composition used to form a multi-layer composite coating comprising two or more cured coating layers, said multi-layer composite coating comprising at least a first coating layer formed on a substrate and a second coating layer over at least a portion of said first polymeric layer, wherein one or both of said first coating layer and said second coating layer are formed from said curable coating composition, and wherein in the absence of a boron-containing compound, said first coating layer and said second coating layer have poor interlayer adhesion,

the improvement comprising the inclusion in said curable coating composition of a boron-containing compound selected from at least one of boric acid, boric acid equivalents, and mixtures thereof in an amount sufficient to improve the interlayer adhesion between said first coating layer and said second coating layer,
wherein one or both of said first coating layer and said second coating layer comprises a cured coating layer formed from a curable coating composition comprising:
(A) at least one film-forming acrylic polymer having reactive functional groups comprising residues of a beta-hydroxy group-containing monomer selected from at least one of:
(i) the reaction product of an ethylenically unsaturated acid functional monomer and an epoxy functional compound having no ethylenic unsaturation;
and
(ii) the reaction product of an ethylenically unsaturated, epoxy functional monomer and a saturated carboxylic acid;
(B) at least one curing agent having functional groups reactive with the functional groups of (A) comprising an aminoplast resin and a blocked polyisocyanate comprising a tricarbamoyl triazine compound;
and
(C) at least one boron-containing compound comprising a reaction product formed from the following reactants:
(i) at least one polysiloxane comprising having at least one of the following structural units (I):
R1nR2mSiO(4−n−m)/2 (I)
wherein each R1 independently is selected from H, a monovalent hydrocarbon group or a siloxane group;
each R2 is independently a group comprising OR′, where R′ is H or an alkyl group having 1 to 20 carbon atoms;
and m and n each represent a positive number fulfilling the requirements of 0<m<4;
0<n<4;
and 2≦(m+n)<4;
and
(ii) at least one boron-containing compound comprising at least one of boric acid, boric acid equivalents, and mixtures thereof.

15 more elements

A method for improving the intercoat adhesion of a multi-layer composite comprising two or more polymeric layers, at least one of which is formed from a thermosetting composition, said composite comprising at least a first polymeric layer formed on at least a portion of a substrate, and a second polymeric layer formed over at least a portion of said first polymeric layer, wherein in the absence of a boron-containing compound, said first polymeric layer and said second polymeric layer have poor interlayer adhesion,

the improvement comprising the inclusion of at least one boron-containing compound in one or both of said first and second polymeric layers in an amount sufficient to improve the interlayer adhesion of said first polymeric layer and said second polymeric layer, wherein said boron-containing compound comprises the reaction product formed from the following reactants:
(A) at least one polysiloxane comprising at least one of the following structural units (I):
R1nR2mSiO(4−n−m)/2 (I)
wherein each R1 is independently selected from a monovalent hydrocarbon group or a siloxane group;
each R2 independently is a group comprising OR′, where R′ is H or an alkyl group having 1 to 20 carbon atoms;
and m and n each represent a positive number fulfilling the requirements of 0<m<4;
0<n<4;
and 2≦(m+n)<4;
and
(B) at least one boron-containing compound selected from at least one of boric acid, boric acid equivalents, and mixtures thereof.

7 more elements

A method for improving the intercoat adhesion of a multi-layer composite comprising two or more polymeric layers, at least one of which is formed from a thermosetting composition, said composite comprising at least a first polymeric layer formed on at least a portion of a substrate, and a second polymeric layer formed over at least a portion of said first polymeric layer, wherein in the absence of a boron-containing compound, said first polymeric layer and said second polymeric layer have poor interlayer adhesion,

the improvement comprising the inclusion of at least one boron-containing compound selected from boric acid, boric acid equivalents and mixtures thereof in one or both of said first and second polymeric layers in an amount sufficient to improve the interlayer adhesion of said first polymeric layer and said second polymeric layer, wherein said first polymeric layer is formed from a thermosetting composition comprising:
(A) at least one film-forming acrylic polymer having reactive functional groups selected from hydroxyl groups, carbamate groups and mixtures thereof;
(B) at least one curing agent selected from aminoplast resins, polyisocyanates, blocked isocyanates and mixtures thereof;
and
(C) at least one boron-containing compound comprising the reaction product formed from the following reactants:
(i) at least one polysiloxane comprising at least one of the following structural units (I):
R1nR2mSiO(4−n−m)/2 (I)
wherein each R1 is independently selected from a monovalent hydrocarbon group or a siloxane group;
each R2 independently is a group comprising OR′, where R′ is H or an alkyl group having 1 to 20 carbon atoms;
and m and n each represent a positive number fulfilling the requirements of 0<m<4;
0<n<4;
and 2≦(m+n)<4;
and
(ii) a boron-containing compound comprising at least one of boric acid, boric acid equivalents, and mixtures thereof;
and
said second polymeric layer comprises a cured layer formed from a thermosetting composition comprising:
(D) at least one film-forming polymer having reactive functional groups;
(E) at least one curing agent having functional groups reactive with the functional groups of (A);
and
(F) at least one boron-containing compound selected from at least one of boric acid, boric acid equivalents, and mixtures thereof.

17 more elements

Multi-layer composites formed from compositions having improved adhesion, coating compositions, and methods related thereto

Life of this patent

Multi-layer composites formed from compositions having improved adhesion, coating compositions, and methods related thereto

Life of this patent

Abstract

Claims35