Curable compositions comprising adhesion promoters

A curable composition comprising

• (A) at least one curable polymer selected from the group consisting of silane-modified polymer, silicone, polyurethane, and epoxide, wherein the silicone is a polyorganosiloxane comprising at least one terminal group of the formula (II):
• -A-Si(R1)m(R2)n(R3)3-(m+n) (II)
• wherein:
• A is a bond, —O— or a linear, branched or cyclic divalent group selected from hydrocarbon residues having 1 to 12 carbon atoms, alkylene, arylene, oxyalkylene, oxyarylene, siloxane-alkylene, siloxane-arylene, ester, amine, glycol, imide, amide, alcohol, carbonate, urethane, urea, sulfide, ether or a derivative or combination thereof;
• each R1 is independently selected from the group consisting of hydrogen, halogen, amino, oximino, a substituted or unsubstituted alkyl, alkenyl, alkenyloxy, alkynyl, alkylnyloxy, cycloaliphatic, cycloaliphatic-O—, aryl, aryloxy, heteroaryl, heteroaryloxy, heteroalicyclic, heteroalicyclicoxy, acyl, acyloxy group or a combination thereof;
• each R2 is independently a group of the general formula (2):
• —O—Y—COOR4 (2)
• wherein
• Y is a substituted or unsubstituted (hetero) aromatic group having 4 to 14 ring atoms, a substituted or unsubstituted saturated or partially unsaturated 4-to 14-membered (hetero) cyclic group or —(C(R5)2)o—;
• R4 is a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloaliphatic, aryl, heteroaryl, and heteroalicyclic group or a combination thereof;
• each R5 is independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloaliphatic or aryl group;
• and
• o is an integer from 1 to 10;
• each R3 independently is a group of the general formula (3):
• —O—Y—CONR6R7 (3)
• wherein
• Y is as defined above;
• R6 is selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl, alkenyl, alkynyl cycloaliphatic, aryl, heteroaryl, and heteroalicyclic group or a combination thereof or R7;
• R7 is a group of the general formula (4):
• —R8—SiR9p(OR10)3-p (4)
• wherein
• R8 is an alkylene group, optionally interrupted by a heteroatom, such as O, N, S or Si;
• each R9 is independently selected from the group consisting of hydrogen, halogen, amino, a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloaliphatic, aryl, heteroaryl, and heteroalicyclic group or a combination thereof;
• each R10 is independently selected from the group consisting of a substituted or unsubstituted alkyl, alkenyl, alkynyl, or acyl group;
• each p independently stands for 0, 1, or 2;
• m is independently 0, 1 or 2;
• and n is independently 1, 2, or 3, wherein the sum n+m is a maximum of 3,
• wherein substituted for the alkyl, alkenyl and alkynyl group means that one or more carbon atoms and/or hydrogen atom(s) are replaced by heteroatoms or functional groups selected from ═O, ═S, —OH, —SH, —NH2, —N(Alk)2, —NO2, —CN, —F, —Cl, —Br, —I, —COOH, —CONH2, —OCN, —NCO, C3-8 cycloalkyl, C6-14 aryl, a 5-10-membered heteroaryl ring, in which 1 to 4 ring atoms independently are nitrogen, oxygen, or sulfur, and a 5-10-membered heteroalicyclic ring, in which 1 to 3 ring atoms are independently nitrogen, oxygen, or sulfur, substituted for the cycloalkyl, aryl, heteroaryl and heteroalicyclic group means that one or more hydrogen atoms of the cycloalkyl group are replaced by functional groups selected from ═O, ═S, —OH, —SH, —NH2, —NO2, —CN, —F, —Cl, —Br, —I, —COOH, —CONH2, —OCN, —NCO, C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, C3-8 cycloalkyl, C6-14 aryl, a 5-10-membered heteroaryl ring, in which 1 to 4 ring atoms independently are nitrogen, oxygen, or sulfur, and a 5-10-membered heteroalicyclic ring, in which 1 to 3 ring atoms independently are nitrogen, oxygen, or sulfur;
• (B) at least one capped adhesion promoter of formula (I):
• B—R11—SiR12q(OR13)3-q (I)
• wherein
• R11 is a linear or branched alkylene group, optionally interrupted by a heteroatom;
• each R12 is independently selected from the group consisting of hydrogen, halogen, amino, a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloaliphatic, aryl, heteroaryl, and heteroalicyclic group or a combination thereof;
• each R13 is independently selected from the group consisting of a substituted or unsubstituted alkyl, alkenyl, alkynyl, or acyl group;
• q independently stands for 0, 1, or 2;
• and
• B is a nitrogen-containing group of formula (1)
• —NR15R16 (1)
• wherein
• R15 is selected from —Si(R17)3;
• R16 is selected from hydrogen, —Si(R17)3 and alkyl substituted with —Si(R17)3, a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloaliphatic, aryl, heteroaryl, and heteroalicyclic group or a combination thereof;
• and
• each R17 is independently selected from hydrogen, a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloaliphatic, or aryl group or a combination thereof;
• or
• wherein R16 is —Si(R17)3 and R15 and R16 combine to form together with the nitrogen atom to which they are attached a group of formula —Si(R17)2—R18—Si(R17)2—, wherein R18 is a linear or branched alkylene group;
• and
• (C) optionally at least one curing catalyst;
• wherein the capped adhesion promoter is a silazane of formula (I) with
• q being 0,
• R11 being methylene, n-propylene or n-butylene,
• each R13 being methyl, ethyl or C1-C5 alkyl substituted with an amino group of the formula —NR19R20 with R19 and R20 independently being selected from hydrogen, methyl, and ethyl, and
• B being a group of formula (1), wherein R15 is —Si(R17)3 and R16 is hydrogen, or alkyl substituted with —Si(R17)3, and each R17 is independently alkyl.

A curable composition comprising

• (A) at least one curable polymer selected from the group consisting of silane-modified polymer, silicone, polyurethane, and epoxide, wherein the at least one curable polymer (A) comprises at least one terminal group of the formula (II):
• -A-Si(R1)m(R2)n(R3)3-(m+n) (II)
• wherein:
• A is a bond, —O— or a linear, branched or cyclic divalent group selected from hydrocarbon residues having 1 to 12 carbon atoms, alkylene, arylene, oxyalkylene, oxyarylene, siloxane-alkylene, siloxane-arylene, ester, amine, glycol, imide, amide, alcohol, carbonate, urethane, urea, sulfide, ether or a derivative or combination thereof;
• each R1 is independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, vinyl, allyl, phenyl, or an aryloxy group having 6 to 14 carbon atoms, or an acyloxy group having 2 to 10 carbon atoms, preferably acetoxy, oximino, alkenyloxy having 2 to 10 carbon atoms, amino or a combination thereof;
• each R2 is independently a group of the general formula (2):
• —O—Y—COOR4 (2)
• wherein
• Y is a substituted or unsubstituted (hetero) aromatic group having 4 to 14 ring atoms, a substituted or unsubstituted saturated or partially unsaturated 4-to 14-membered (hetero) cyclic group or —(C(R5)2)o—;
• R4 is methyl, ethyl, or a combination thereof;
• each R5 is independently selected from methyl, carboxymethyl or an (alkyl) ester;
• and
• o is an integer from 1 to 10;
• each R3 independently is a group of the general formula (3):
• —O—Y—CONR6R7 (3)
• wherein
• Y is as defined above;
• R6 is selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl, alkenyl, alkynyl cycloaliphatic, aryl, heteroaryl, and heteroalicyclic group or a combination thereof or R7;
• R7 is a group of the general formula (4):
• —R8—SiR9p(OR10)3-p (4)
• wherein
• R8 is methylene or propylene;
• each R9 is independently selected from the group consisting of hydrogen, halogen, amino, a substituted or unsubstituted alkyl;
• each R10 is independently selected from the group consisting of a substituted or unsubstituted alkyl, alkenyl, alkynyl, or acyl group;
• each p independently stands for 0, 1, or 2;
• m is independently 0, 1 or 2;
• and n is independently 1, 2, or 3, wherein the sum n+m is a maximum of 3,
• wherein substituted for the alkyl, alkenyl and alkynyl group means that one or more carbon atoms and/or hydrogen atom(s) are replaced by heteroatoms or functional groups selected from ═O, ═S, —OH, —SH, —NH2, —N(Alk)2, —NO2, —CN, —F, —Cl, —Br, —I, —COOH, —CONH2, —OCN, —NCO, C3-8 cycloalkyl, C6-14 aryl, a 5-10-membered heteroaryl ring, in which 1 to 4 ring atoms independently are nitrogen, oxygen, or sulfur, and a 5-10-membered heteroalicyclic ring, in which 1 to 3 ring atoms are independently nitrogen, oxygen, or sulfur, substituted for the cycloalkyl, aryl, heteroaryl and heteroalicyclic group means that one or more hydrogen atoms of the cycloalkyl group are replaced by functional groups selected from ═O, ═S, —OH, —SH, —NH2, —NO2, —CN, —F, —Cl, —Br, —I, —COOH, —CONH2, —OCN, —NCO, C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, C3-8 cycloalkyl, C6-14 aryl, a 5-10-membered heteroaryl ring, in which 1 to 4 ring atoms independently are nitrogen, oxygen, or sulfur, and a 5-10-membered heteroalicyclic ring, in which 1 to 3 ring atoms independently are nitrogen, oxygen, or sulfur;
• (B) at least one capped adhesion promoter of formula (I):
• B—R11—SiR12q(OR13)3-q (I)
• wherein
• R11 is a linear or branched alkylene group, optionally interrupted by a heteroatom;
• each R12 is independently selected from the group consisting of hydrogen, halogen, amino, a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloaliphatic, aryl, heteroaryl, and heteroalicyclic group or a combination thereof;
• each R13 is independently selected from the group consisting of a substituted or unsubstituted alkyl, alkenyl, alkynyl, or acyl group;
• q independently stands for 0, 1, or 2;
• and
• B is a nitrogen-containing group of formula (1)
• —NR15R16 (1)
• wherein
• R15 is selected from —Si(R17)3;
• R16 is selected from hydrogen, —Si(R17)3 and alkyl substituted with —Si(R17)3, a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloaliphatic, aryl, heteroaryl, and heteroalicyclic group or a combination thereof;
• and
• each R17 is independently selected from hydrogen, a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloaliphatic, or aryl group or a combination thereof;
• or
• wherein R16 is —Si(R17)3 and R15 and R16 combine to form together with the nitrogen atom to which they are attached a group of formula —Si(R17)2—R18—Si(R17)2—, wherein R18 is a linear or branched alkylene group;
• and
• (C) optionally at least one curing catalyst.

A curable composition comprising

• (A) at least one curable polymer selected from the group consisting of silane-modified polymer, silicone, polyurethane, and epoxide, wherein the silicone is a polyorganosiloxane comprising at least one terminal group of the formula (II):
• -A-Si(R1)m(R2)n(R3)3-(m+n) (II)
• wherein:
• A is a bond, —O— or a linear, branched or cyclic divalent group selected from hydrocarbon residues having 1 to 12 carbon atoms, alkylene, arylene, oxyalkylene, oxyarylene, siloxane-alkylene, siloxane-arylene, ester, amine, glycol, imide, amide, alcohol, carbonate, urethane, urea, sulfide, ether or a derivative or combination thereof;
• each R1 is independently selected from the group consisting of hydrogen, halogen, amino, oximino, a substituted or unsubstituted alkyl, alkenyl, alkenyloxy, alkynyl, alkylnyloxy, cycloaliphatic, cycloaliphatic-O—, aryl, aryloxy, heteroaryl, heteroaryloxy, heteroalicyclic, heteroalicyclicoxy, acyl, acyloxy group or a combination thereof;
• each R2 is independently a group of the general formula (2):
• —O—Y—COOR4 (2)
• wherein
• Y is a substituted or unsubstituted (hetero) aromatic group having 4 to 14 ring atoms, a substituted or unsubstituted saturated or partially unsaturated 4-to 14-membered (hetero) cyclic group or —(C(R5)2)o—;
• R4 is a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloaliphatic, aryl, heteroaryl, and heteroalicyclic group or a combination thereof;
• each R5 is independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloaliphatic or aryl group;
• and
• o is an integer from 1 to 10;
• each R3 independently is a group of the general formula (3):
• —O—Y—CONR6R7 (3)
• wherein
• Y is as defined above;
• R6 is selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl, alkenyl, alkynyl cycloaliphatic, aryl, heteroaryl, and heteroalicyclic group or a combination thereof or R7;
• R7 is a group of the general formula (4):
• —R8—SiR9p(OR10)3-p (4)
• wherein
• R8 is an alkylene group, optionally interrupted by a heteroatom, such as O, N, S or Si;
• each R9 is independently selected from the group consisting of hydrogen, halogen, amino, a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloaliphatic, aryl, heteroaryl, and heteroalicyclic group or a combination thereof;
• each R10 is independently selected from the group consisting of a substituted or unsubstituted alkyl, alkenyl, alkynyl, or acyl group;
• each p independently stands for 0, 1, or 2;
• m is independently 0, 1 or 2;
• and n is independently 1, 2, or 3, wherein the sum n+m is a maximum of 3,
• wherein substituted for the alkyl, alkenyl and alkynyl group means that one or more carbon atoms and/or hydrogen atom(s) are replaced by heteroatoms or functional groups selected from ═O, ═S, —OH, —SH, —NH2, —N(Alk)2, —NO2, —CN, —F, —Cl, —Br, —I, —COOH, —CONH2, —OCN, —NCO, C3-8 cycloalkyl, C6-14 aryl, a 5-10-membered heteroaryl ring, in which 1 to 4 ring atoms independently are nitrogen, oxygen, or sulfur, and a 5-10-membered heteroalicyclic ring, in which 1 to 3 ring atoms are independently nitrogen, oxygen, or sulfur, substituted for the cycloalkyl, aryl, heteroaryl and heteroalicyclic group means that one or more hydrogen atoms of the cycloalkyl group are replaced by functional groups selected from ═O, ═S, —OH, —SH, —NH2, —NO2, —CN, —F, —Cl, —Br, —I, —COOH, —CONH2, —OCN, —NCO, C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, C3-8 cycloalkyl, C6-14 aryl, a 5-10-membered heteroaryl ring, in which 1 to 4 ring atoms independently are nitrogen, oxygen, or sulfur, and a 5-10-membered heteroalicyclic ring, in which 1 to 3 ring atoms independently are nitrogen, oxygen, or sulfur;
• (B) at least one capped adhesion promoter of formula (I):
• B—R11—SiR12q(OR13)3-q (I)
• wherein
• R11 is a linear or branched alkylene group, optionally interrupted by a heteroatom;
• each R12 is independently selected from the group consisting of hydrogen, halogen, amino, a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloaliphatic, aryl, heteroaryl, and heteroalicyclic group or a combination thereof;
• each R13 is independently selected from the group consisting of a substituted or unsubstituted alkyl, alkenyl, alkynyl, or acyl group;
• q independently stands for 0, 1, or 2;
• and
• B is a nitrogen-containing group of formula (1)
• —NR15R16 (1)
• wherein
• R15 is selected from —Si(R17)3;
• R16 is selected from hydrogen, —Si(R17)3 and alkyl substituted with —Si(R17)3, a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloaliphatic, aryl, heteroaryl, and heteroalicyclic group or a combination thereof;
• and
• each R17 is independently selected from hydrogen, a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloaliphatic, or aryl group or a combination thereof;
• or
• wherein R16 is —Si(R17)3 and R15 and R16 combine to form together with the nitrogen atom to which they are attached a group of formula —Si(R17)2—R18—Si(R17)2—, wherein R18 is a linear or branched alkylene group;
• (C) optionally at least one curing catalyst;
• and
• (D) at least one adhesion promoter different from the capped adhesion promoter, wherein said additional adhesion promoter is selected from the group consisting of 3-(N,N-dimethylamino)propyltrimethoxysilane, 3-(N,N-dimethylamino)propyltriethoxysilane, (N,N-dimethylamino)methyltrimethoxysilane, (N,N-dimethylamino)methyltriethoxysilane, 3-(N, N-diethylamino)propyltrimethoxysilane, 3-(N,N-diethylamino)propyltriethoxysilane, (N,N-diethylamino)methyltrimethoxysilane, (N,N-diethylamino)methyltriethoxysilane, bis(3-trimethoxysilyl)propylamine, bis(3-triethoxysilyl)propylamine, 4-amino-3,3-dimethylbutyltrimethoxy silane and 4-amino-3,3-dimetylbuthyltriethoxy silane.