Patent EA-000794-B1 (EA)
Title: Aminosilane salts and silanamides of carboxylic acids as corrosion inhibitors
Inventor: KRAMER ANDREAS
IPC: C23F11/12
Filed: 1996-06-17
Abstract: 1. A coating composition comprising  a) an organic film-forming binder and b) as corrosion inhibitor at least one salt (.alpha.) and/or at least one amide (.beta.), both components (.alpha.) and (.beta.) derived from i) a polyacrylic acid, an acrylic acid-maleic acid copolymer, or a carboxylic acid of the formula I   in which R1 is hydrogen, C1-C25 alkyl, C2-C25 alkyl interrupted by oxygen or sulfur; C2-C24 alkenyl, C4-C15 cycloalkyl which is unsubstituted or substituted by C1-C4 allyl and/or carboxyl; C5-C15 cycloalkenyl which is unsubstituted or substituted by C1-C4 alkyl and/or carboxyl; C13-C26 polycycloalkyl, C7-C9 phenylalkyl which is unsubstituted or substituted on the phenyl ring by C1-C4 alkyl; --COR6, a 5- or 6-membered heterocyclic ring which is unsubstituted or substituted by C1-C4 alkyl, C1-C4 alkoxy, halogen or carboxyl; a 5- or 6-membered heterocyclic ring which is benzo-fused and is unsubstituted or substituted by C1-C4 alkyl, C1-C4 alkoxy, halogen or carboxyl; or else R1 is a radical of the formula II, III or IV   R2, R3, R4 and R5 independently of one another are hydrogen, hydroxyl, C1-C18 alkoxy, C2-C18 alkoxy which is interrupted by oxygen or sulfur; C1-C25 alkyl, C2-C25 alkyl which is interrupted by oxygen or sulfur; C2-C24 alkenyl, C5-C15 cycloalkyl which is unsubstituted or substituted by C1-C4 alkyl; C5-C15 cycloalkenyl which is unsubstituted or substituted by C1-C4 alkyl; phenyl or naphthyl which is unsubstituted or substituted by C1-C4 alkyl; C7-C9 phenylalkyl which is unsubstituted or substituted on the phenyl ring by C1-C4 alkyl; C10-C12 naphthylalkyl which is unsubstituted or substituted on the naphthyl ring system by C1-C4 alkyl; or are -COR6, with the proviso that, if one of the radicals R2, R3, R4 and R5 is hydroxyl, the other radical attached to the same carbon atom is other than hydroxyl; or else R2 and R3 or R4 and R5, together with the carbon atom to which they are attached, form an unsubstituted or C1-C4 alkyl-substituted C5-C12 cycloalkylidene ring; R6 is hydroxyl, C1-C18 alkoxy, C2-C18 alkoxy which is interrupted by oxygen or sulfur; or   R7, R8, R9, R10 and R11 independently of one another are hydrogen, hydroxyl, halogen, nitro, cyano, CF3, -COR6, C1-C25 alkyl, C2-C25 alkyl which is interrupted by oxygen or sulfur; C1-C25 haloalkyl, C1-C18 alkoxy, C2-C18 alkoxy which is interrupted by oxygen or sulfur; C1-C18 alkylthio, C2-C24 alkenyl, C5-C15 cycloalkyl which is unsubstituted or substituted by C1-C4 alkyl; C5-C15 cycloalkenyl which is unsubstituted or substituted by C1-C4 alkyl; phenyl or naphthyl which is unsubstituted or substituted by C1-C4 alkyl; C7-C9 phenylalkyl which is unsubstituted or substituted on the phenyl ring by C1-C4 alkyl; C10-C12 naphthylalkyl which is unsubstituted or substituted on the naphthyl ring system by C1-C4 alkyl; phenoxy or naphthoxy which is unsubstituted or substituted by C1-C4 alkyl; C7-C9 phenylalkoxy which is unsubstituted or substituted on the phenyl ring by C1-C4 alkyl; C10-C12 naphthylalkoxy which is unsubstituted or substituted on the naphthyl ring system by C1-C4 alkyl; or else the radicals R8 and R9 or the radicals R9 and R10 or the radicals R10 and R11 or the radicals R7 and R11, together with the carbon atoms to which they are attached, form an unsubstituted or C1-C4 alkyl-, halogen- or C1-C4 alkoxy-substituted benzo ring, with the proviso that at least one of the radicals R7, R8, R9, R10 and R11 is hydrogen; R12 is hydroxyl, halogen, nitro, cyano, CF3, C1-C25 alkyl, C2-C25 alkyl which is interrupted by oxygen or sulfur; C1-C25 haloalkyl, C1-C18 alkoxy, C2-C18 alkoxy which is interrupted by oxgyen or sulfur; C1-C18 alkylthio or C2-C24 alkenyl; R13 and R14 independently of one another are hydrogen, C1-C25 alkyl, C1-C18 alkoxy or -Y-(CH2)sCOR6; R15 and R16 independently of one another are hydrogen, C1-C25 alkyl, C3-C25 alkyl which is interrupted by oxygen or sulfur; C2-C24 alkenyl, C5-C15 cycloalkyl which is unsubstituted or substituted by C1-C4 alkyl; phenyl or naphthyl which is unsubstituted or substituted by C1-C4 alkyl; X1 is a direct bond, oxygen, sulfur,   C1-C18 alkylene, C2-C18 alkylene which is interrupted by oxygen or sulfur; C2-C18 alkenylene, C2-C18 alkynylene, C2-C20 alkylidene, C7-C20 phenylalkylidene or C5-C8 cycloalkylene, with the proviso that, if m and n are 0, X1 is other than oxygen and sulfur, Y is oxygen or   where Ra is hydrogen or C1-C8 alkyl, m and n independently of one another are integers from 0 to 10, p is an integer from 0 to 4, s is an integer from 1 to 8, and ii) an aminosilane of the formula V   in which R17 and R18 independently of one another are hydrogen, C1-C25 alkyl, 2-hydroxyethyl, C3-C25 alkyl which is interrupted by oxygen or sulfur; C2-C24 alkenyl or   R19 is C1-C25 alkyl, C2-C25 alkyl which is interrupted by oxygen or sulfur; hydroxyl, C1-C18 alkoxy or C2-C24 alkenyl; R20 is hydroxyl, C1-C18 alkoxy or C2-C18 alkoxy which is interrupted by oxygen or sulfur; and, if a and b together are 1, three radicals R20 together are N(CH2CH2O-)3, R21 is hydrogen or C1-C8 alkyl; X2 is C1-C18 alkylene, C2-C20 alkylidene, C7-C20 phenylalkylidene, C5-C8 cycloalkylene, phenylene or naphthylene which is unsubstituted or substituted by C1 -C4 alkyl; or is C4-C18 alkylene which is interrupted by oxygen, sulfur or   with the proviso that two nitrogen atoms are not attached to the same carbon atom, a is 1 or 2, and b is 0, 1 or 2. 2. A coating composition according to claim 1, wherein R1 is C1-C25 alkyl, C2-C18 alkyl which is interrupted by oxygen or sulfur; C2-C18 alkenyl, C5-C12 cycloalkyl which is unsubstituted or substituted by C1 -C4 alkyl and/or carboxyl; C5-C12 cycloalkenyl which is unsubstituted or substituted C1 -C4 alkyl and/or carboxyl; C13-C26 polycycloalkyl, C7-C9 phenylalkyl, -COR6 or a radical of the formula II, III or IV   R2, R3, R4 and R5 independently of one another are hydrogen, hydroxyl, C1-C12 alkoxy, C2-C12 alkoxy which is interrupted by oxygen or sulfur; C1-C18 alkyl, C2-C18 alkyl which is interrupted by oxygen or sulfur; C2-C18 alkenyl, C5-C12 cycloalkyl, C5-C12 cycloalkenyl, phenyl, naphthyl, C7-C9 phenylalkyl, C10-C12 naphthylalkyl or --COR6, with the proviso that, if one of the radicals R2, R3, R4 and R5 is hydroxyl, the other radical attached to the same carbon atom is other than hydroxyl; or else R2 and R3 or R4 and R5, together with the carbon atom to which they are attached, form a C5 -C10 cycloalkylidene ring, R6 is hydroxyl, C1-C12 alkoxy, C2-C12 alkoxy which is interrupted by oxygen or sulfur; or R6 is   R7, R8, R9, R10 and R11 independently of one another are hydrogen, hydroxyl, halogen, nitro, cyano, CF3, -COR6, C1-C18 alkyl, C2-C18 alkyl which is interrupted by oxygen or sulfur; C1-C18 haloalkyl, C1-C12 alkoxy, C2-C12 alkoxy which is interrupted by oxygen or sulfur; C1-C12 alkylthio, C2-C18 alkenyl, C5-C12 cycloalkyl, C5-C12 cycloalkenyl, phenyl, naphthyl, C7-C9 phenylalkyl, C10-C12 naphthylalkyl, phenoxy, naphthoxy, C7-C9 phenylalkoxy or C10-C12 naphthylalkoxy; or else the radicals R<8> and R9 or the radicals R9 and R10 or the radicals R10 and R11 or the radicals R7 and R11, together with the carbon atoms to which they are attached, form a benzo ring, with the proviso that at least one of the radicals R7, R8, R9, R10 or R11 and hydrogen, R12 is hydroxyl, chlorine, nitro, cyano, CF3, C1-C18 alkyl, C2-C18 alkyl which is interrupted by oxygen or sulfur; C1-C18 haloalkyl, C1-C12 alkoxy, C2-C12 alkoxy which is interrupted by oxygen or sulfur; C1-C12 alkylthio or C2-C18 alkenyl, R13 and R14 independently of one another are hydrogen, C1-C18 alkyl, C1-C12 alkoxy or -Y--(CH2)sCOR6,  R15 and R16 independently of one another are hydrogen, C1-C18 alkyl, C3-C18 alkyl which is interrupted by oxygen or sulfur; C2-C18 alkenyl, C5-C12 cycloalkyl, phenyl or naphthyl, R17 and R18 independently of one another are hydrogen, C1-C18 alkyl, C3-C18 alkyl which is interrupted by oxygen or sulfur; or is C2-C18 alkenyl, R19 is C1-C18 alkyl, C2-C18 alkyl which is interrupted by oxygen or sulfur; hydroxyl, C1-C12 alkoxy or C2-C18 alkenyl, R20 is hydroxyl, C1-C12 alkoxy or C2-C12 alkoxy which is interrupted by oxygen or sulfur; and, if a and b together are 1, three radicals R20 together are N(CH2CH2O-)3 R21 is hydrogen or C1-C6 alkyl, X1 is a direct bond, oxygen, sulfur,  , C1-C12 alkylene, C2-C12 alkylene which is interrupted by oxygen or sulfur; C2-C12 alkenylene, C2-C12 alkynylene, C2-C16 alkylidene, C7-C16 phenylalkylidene or C5-C8 cycloalkylene, with the proviso that, if m and n are 0, X1 is other than oxygen and sulfur, X2 is C2-C12 alkylene, C2-C16 alkylidene, C7-C16 phenylalkylidene, C5-C8 cycloalkylene, phenylene, naphthylene, or C4-C12 alkylene which is interrupted by oxygen, sulfur or   with the proviso that two nitrogen atoms are not attached to the same carbon atom, Y is oxygen or   Ra is hydrogen or C1-C6 alkyl, m and n independently of one another are integers from 0 to 8, p is an integer from 0 to 2, and s is an integer from 1 to 6. 3. A coating composition according to claim 1, wherein R1 is C1-C25 alkyl, C2-C12 alkyl which is interrupted by oxygen; C2-C18 alkenyl, C5-C12 cycloalkyl, C5-C12 cycloalkenyl which is unsubstituted or substituted by C1 -C4 alkyl and/or carboxyl; C7-C9 phenylalkyl, -COR6 or a radical of the formula II or III   R2, R3, R4 and R5 independently of one another are hydrogen, C1-C8 alkoxy, C1-C18 alkyl, C2-C12 alkyl which is interrupted by oxygen; C2-C12 alkenyl, C5-C8 cycloalkyl, C5-C8 cycloalkenyl, phenyl, naphthyl, benzyl or -COR6, or else R2 and R3 or R4 and R5, together with the carbon atom to which they are attached, form a C5-C7 cycloalkylidene ring, R6 is hydroxyl, C1-C12 alkoxy, C2-C12 alkoxy which is interrupted by oxygen or sulfur; or R6 is   R7, R8, R9, R10 and R11 independently of one another are hydrogen, hydroxyl, chlorine, nitro, -COR6, C1-C12 alkyl, C2-C12 alkyl which is interrupted by oxygen; C1-C8 alkoxy, C1-C8 alkylthio, C2-C12 alkenyl, C5-C8 cycl