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US 8,298,679 B2Granted
Aqueous silane systems based on bis(trialkoxysilylalkyl)amines
AssigneeEvonik Degussa GmbH
InventorsPhilipp Albert, Eckhard Just, Christian Wassmer, Burkhard Standke
Life of this patent
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Abstract
The invention relates to an aqueous composition of bis-amino-functional silicon compounds which is essentially free of organic solvents and releases essentially no further alcohol in the course of crosslinking, and to processes for preparing it and to the use thereof, for example for hydrophobization of metal or glass surfaces.
Claims78
A composition containing substantially water-soluble, bis-aminofunctional silicon compounds and water, the silicon compounds being derived from alkoxysilanes and having crosslinking structural elements which form chain-like, cyclic, crosslinked and/or three-dimensionally crosslinked structures, at least one structure in idealized form corresponding to the general formula I,
- (R2O)[(R2O)1-x(R3)xSi(B)O]b[(Y)2Si(A)Si(Y)2O]a[Si(C)(R5)y(OR4)1-yO]c[Si(D)(R7)u(OR6)1-uO]d[Si(E)(R8)v(OR9)1-vO]wR9.(HX)e (I),
- in the structural elements derived from alkoxysilanes, with
- A corresponding to a bisaminoalkyl radical,
- B corresponding to an aminoalkyl radical,
- C corresponding to an alkyl radical,
- D corresponding to an epoxy or ether radical and
- E corresponding to an organofunctional radical,
- Y corresponding to OR1 or, in crosslinked and/or three-dimensionally crosslinked structures, independently of one another, OR1 or O1/2,
- R1, R2, R4, R6 and/or R9 substantially corresponding to hydrogen and R3, R5, R7 and/or R8 corresponding to organofunctional radicals, and
- HX being an acid, in which X is an inorganic or organic acid radical,
- with 0≦x≦1, 0≦y≦1, 0≦u≦1, a≧1, b≧0, c≧0, d≧0, w≧0, e≧0 and (a+b+c+d+w)≧2, and
- the composition being substantially free of organic solvents and releasing substantially no more alcohol on crosslinking.
9 more elements
A process for the preparation of a composition containing substantially water-soluble, bis-aminofunctional silicon compounds substantially free of alkoxy groups, and water and an acid, wherein water, an acid, optionally an alcohol and optionally a catalyst are initially introduced and
- at least one bisaminoalkoxysilane of the formula II
- (OR1)3Si-A-Si(OR1)3 (II)
- where A is a bis-aminofunctional group of the formula III
- —(CH2)i—[NH(CH2)f]gNH[(CH2)f*NH]g*—(CH2)i*— (III),
- in which i, i*, f, f*, g or g* are identical or different, with i and/or i*=from 0 to 8, f and/or f*=1, 2 or 3, g and/or g*=0, 1 or 2 and R1 corresponds to a linear, cyclic and/or branched alkyl radical having 1 to 4 C atoms, and/or the condensates thereof, and optionally
- at least one aminoalkylalkoxysilane of the formula IV
- B—Si(R3)x(OR2)3-x (IV)
- where x=0 or 1, R2 corresponds to a linear, branched and/or cyclic alkyl radical having 1 to 4 C atoms and B corresponds to one of the following aminofunctional groups of the general formula Va or Vb
- R10h*NH(2-h*)[(CH2)h(NH)]j[(CH2)l(NH)]n—(CH2)k— (Va),
- in which 0≦h≦6;
- h*=0, 1 or 2, j=0, 1 or 2;
- 0≦l≦6;
- n=0, 1 or 2;
- 0≦k≦6 and R10 corresponds to a benzyl, aryl, vinyl or formyl radical and/or to a linear, branched and/or cyclic alkyl radical having 1 to 8 C atoms, and/or
- [NH2(CH2)m]2N(CH2)p— (Vb),
- in which 0≦m≦6 and 0≦p≦6, and/or the condensates thereof, and optionally
- at least one alkylalkoxysilane of the general formula VI
- C—Si(R5)y(OR4)3-y (VI)
- where y=0 or 1, corresponds to a linear, branched or cyclic alkyl radical having 1 to 20 C atoms, R5 corresponds to a linear, branched or cyclic alkyl radical having 1 to 12 C atoms and/or an aryl radical, and R4 corresponds to a linear, branched and/or cyclic alkyl radical having 1 to 4 C atoms, and/or the condensates thereof, and optionally
- at least one epoxy- or ether-alkoxysilane of the general formula VII
- D—Si(R7)u(OR6)3-u (VII)
- where u=0 or 1, D corresponds to a 3-glycidyloxyalkyl, 3-glycidyloxypropyl, epoxyalkyl, epoxycycloalkyl or polyalkylglycolalkyl radical or to a polyalkylglycol-3-propyl radical, R7 corresponds to a linear, branched or cyclic alkyl radical having 1 to 4 C atoms and R6 corresponds to a linear, branched and/or cyclic alkyl radical having 1 to 4 C atoms, and/or the condensates thereof, and optionally
- at least one organofunctional alkoxysilane of the formula VIII
- E-Si(R8)v(OR9)3-v (VIII)
- where v=0 or 1, R8 corresponds to a linear, branched or cyclic alkyl radical having 1 to 4 C atoms, E corresponds to a radical R8*—Ym—(CH2)s—, with R8* corresponding to a mono-, oligo- or perfluorinated alkyl radical having 1 to 9 C atoms or to a mono-, oligo- or perfluorinated aryl radical, and Y corresponding to a CH2, O, aryl or S radical, and m being 0 or 1 and s being 0 or 2, or to a vinyl, allyl or isopropenyl radical, mercaptoalkyl radical, sulfanealkyl radical, ureidoalkyl radical, to an acryloyloxyalkyl radical or to a linear, branched or cyclic alkoxy radical having 1 to 4 C atoms and R9 corresponds to a linear, branched and/or cyclic alkyl radical having 1 to 4 C atoms, and/or the condensates thereof,
- are hydrolyzed and the alcohol is substantially removed.
23 more elements
A process for the preparation of a composition containing substantially water-soluble, bis-aminofunctional silicon compounds substantially free of alkoxy groups, and water and an acid, wherein an aqueous solution of at least one water-soluble silane of the general formulae II, IV and/or VII or the water-soluble condensates thereof or the water-soluble hydrolysis products of a silane of the general formula VI is initially introduced,
- the silane of the formula II corresponding to a bisaminoalkoxysilane
- (OR1)3Si-A-Si(OR1)3 (II)
- where A is a bis-aminofunctional group of the formula III
- —(CH2)i—[NH(CH2)f]gNH[(CH2)f*NH]g*—(CH2)i*— (III),
- in which i, i*, f, f*, g or g* are identical or different, with i and/or i*=from 0 to 8, f and/or f*=1, 2 or 3, g and/or g*=0, 1 or 2 and R1 corresponds to a linear, cyclic and/or branched alkyl radical having 1 to 4 C atoms, and/or the condensates thereof,
- the silane of the formula IV corresponding to an aminoalkylalkoxysilane
- B—Si(R3)x(OR2)3-x (IV)
- where x=0 or 1, R2 corresponds to a linear, branched and/or cyclic alkyl radical having 1 to 4 C atoms and B corresponds to one of the following aminofunctional groups of the general formula Va or Vb
- R10h*NH(2-h*)[(CH2)h(NH)]j[(CH2)l(NH)]n—(CH2)k— (Va),
- in which 0≦h≦6;
- h*=0, 1 or 2, j=0, 1 or 2;
- 0≦l≦6;
- n=0, 1 or 2;
- 0≦k≦6 and R10 corresponds to a benzyl, aryl, vinyl or formyl radical and/or to a linear, branched and/or cyclic alkyl radical having 1 to 8 C atoms, and/or
- [NH2(CH2)m]2N(CH2)p— (Vb),
- in which 0≦m≦6 and 0≦p≦6, and/or the condensates thereof,
- the silane of the formula VII corresponding to an epoxy- or ether-alkoxysilane
- D-Si(R7)u(OR6)3-u (VII)
- where u=0 or 1, D corresponds to a 3-glycidyloxyalkyl, 3-glycidyloxypropyl, epoxyalkyl, epoxycycloalkyl or polyalkylglycolalkyl radical or to a polyalkylglycol-3-propyl radical, R7 corresponds to a linear, branched or cyclic alkyl radical having 1 to 4 C atoms and R6 corresponds to a linear, branched and/or cyclic alkyl radical having 1 to 4 C atoms, and/or the condensates thereof,
- the silane of the formula VI corresponding to an alkylalkoxysilane
- C—Si(R5)y(OR4)3-y (VI)
- where y=0 or 1, C corresponds to a linear, branched or cyclic alkyl radical having 1 to 4 C atoms, R5 corresponds to a linear, branched or cyclic alkyl radical having 1 to 4 C atoms and/or an aryl radical, and R4 corresponds to a linear, branched and/or cyclic alkyl radical having 1 to 4 C atoms,
- and optionally acid, optionally alcohol and optionally a catalyst and optionally one or more further silanes of the general formulae II, IV, VI, VII and/or VIII or the condensates thereof are added
- the added silane of the formula VI corresponding to an alkylalkoxysilane
- C—Si(R5)y(OR4)3-y (VI)
- where y=0 or 1, C corresponds to a linear, branched or cyclic alkyl radical having 1 to 20 C atoms, R5 corresponds to a linear, branched or cyclic alkyl radical having 1 to 12 C atoms and/or an aryl radical, and R4 corresponds to a linear, branched and/or cyclic alkyl radical having 1 to 4 C atoms,
- the silane of the formula VIII corresponding to an organofunctional alkoxysilane
- E-Si(R8)v(OR9)3-v (VIII)
- where v=0 or 1, R8 corresponds to a linear, branched or cyclic alkyl radical having 1 to 4 C atoms, E corresponds to a radical R8—Ym—(CH2)s—, with R8* corresponding to a mono-, oligo- or perfluorinated alkyl radical having 1 to 9 C atoms or to a mono-, oligo- or perfluorinated aryl radical, and Y corresponding to a CH2, O, aryl or S radical and m being 0 or 1 and s being 0 or 2, or to a vinyl, allyl or isopropenyl radical, mercaptoalkyl radical, sulfanealkyl radical, ureidoalkyl radical, to an acryloyloxyalkyl radical or to a linear, branched or cyclic alkoxy radical having 1 to 4 C atoms and R9 corresponds to a linear, branched and/or cyclic alkyl radical having 1 to 4 C atoms, and/or the condensates thereof,
- and are hydrolyzed and the alcohol is substantially removed.
27 more elements
A process for the preparation of a composition containing substantially water-soluble, bis-aminofunctional silicon compounds substantially free of alkoxy groups, and water and an acid, wherein an organic solvent, optionally water, optionally an acid and/or optionally a catalyst are initially introduced and
- at least one bisaminoalkoxysilane of the formula H
- (OR1)3Si-A-Si(OR1)3 (H)
- where A is a bis-aminofunctional group of the formula III
- —(CH2)i—[NH(CH2)f]gNH[(CH2)f*NH]g*—(CH2)i*— (III),
- in which i, i*, f, f*, g or g* are identical or different, with i and/or i*=from 0 to 8, f and/or f*=1, 2 or 3, g and/or g*=0, 1 or 2 and R1 corresponds to a linear, cyclic and/or branched alkyl radical having 1 to 4 C atoms, and/or the condensates thereof, and optionally
- at least one aminoalkylalkoxysilane of the formula IV
- B—Si(R3)x(OR2)3-x (IV)
- where x=0 or 1, R2 corresponds to a linear, branched and/or cyclic alkyl radical having 1 to 4 C atoms and B corresponds to one of the following aminofunctional groups of the general formula Va or Vb
- R10h*NH(2-h*)[(CH2)h(NH)]j[(CH2)l(NH)]n—(CH2)k— (Va),
- in which 0≦h≦6;
- h*=0, 1 or 2, j=0, 1 or 2;
- 0≦l≦6;
- n=0, 1 or 2;
- 0≦k≦6 and R10 corresponds to a benzyl, aryl, vinyl or formyl radical and/or to a linear, branched and/or cyclic alkyl radical having 1 to 8 C atoms, and/or
- [NH2(CH2)m]2N(CH2)p— (Vb),
- in which 0≦m≦6 and 0≦p≦6, and/or the condensates thereof, and optionally
- at least one alkylalkoxysilane of the general formula VI
- C—Si(R5)y(OR4)3-y (VI)
- where y=0 or 1, C corresponds to a linear, branched or cyclic alkyl radical having 1 to 20 C atoms, R5 corresponds to a linear, branched or cyclic alkyl radical having 1 to 12 C atoms and/or an aryl radical, and R4 corresponds to a linear, branched and/or cyclic alkyl radical having 1 to 4 C atoms, and/or the condensates thereof, and optionally
- at least one epoxy- or ether-alkoxysilane of the general formula VII
- D-Si(R7)u(OR6)3-u (VII)
- where u=0 or 1, D corresponds to a 3-glycidyloxyalkyl, 3-glycidyloxypropyl, epoxyalkyl, epoxycycloalkyl or polyalkylglycolalkyl radical or to a polyalkylglycol-3-propyl radical, R7 corresponds to a linear, branched or cyclic alkyl radical having 1 to 4 C atoms and R6 corresponds to a linear, branched and/or cyclic alkyl radical having 1 to 4 C atoms, and/or the condensates thereof, and optionally
- at least one organofunctional alkoxysilane of the formula VIII
- E-Si(R8)v(OR9)3-v (VIII)
- where v=0 or 1, R8 corresponds to a linear, branched or cyclic alkyl radical having 1 to 4 C atoms, E corresponds to a radical R8*—Ym—(CH2)s—, with R8* corresponding to a mono-, oligo- or perfluorinated alkyl radical having 1 to 9 C atoms or to a mono-, oligo- or perfluorinated aryl radical, and Y corresponding to a CH2, O, aryl or S radical and m being 0 or 1 and s being 0 or 2, or to a vinyl, allyl or isopropenyl radical, mercaptoalkyl radical, sulfanealkyl radical, ureidoalkyl radical, to an acryloyloxyalkyl radical or to a linear, branched or cyclic alkoxy radical having 1 to 4 C atoms and R9 corresponds to a linear, branched and/or cyclic alkyl radical having 1 to 4 C atoms, and/or the condensates thereof,
- are hydrolyzed and the hydrolysis alcohol and the solvent are substantially removed.
23 more elements
A process for the preparation of a composition containing substantially water-soluble, bis-aminofunctional silicon compounds substantially free of alkoxy groups, and water and an acid, wherein
- at least one epoxy- or ether-alkoxysilane of the general formula VII
- D-Si(R7)u(OR6)3-u (VII)
- where u=0 or 1, D corresponds to a 3-glycidyloxyalkyl, 3-glycidyloxypropyl, epoxyalkyl, epoxycycloalkyl or polyalkylglycolalkyl radical or to a polyalkylglycol-3-propyl radical, R7 corresponds to a linear, branched or cyclic alkyl radical having 1 to 4 C atoms and R6 corresponds to a linear, branched and/or cyclic alkyl radical having 1 to 4 C atoms, and/or the condensates thereof, and/or
- at least one alkylalkoxysilane of the general formula VI
- C—Si(R5)y(OR4)3-y (VI)
- where y=0 or 1, C corresponds to a linear, branched or cyclic alkyl radical having 1 to 20 C atoms, R5 corresponds to a linear, branched or cyclic alkyl radical having 1 to 12 C atoms and/or an aryl radical, and R4 corresponds to a linear, branched and/or cyclic alkyl radical having 1 to 4 C atoms, and/or the condensates thereof, and/or
- at least one organofunctional alkoxysilane of the formula VIII
- E-Si(R8)v(OR9)3-v (VIII)
- where v=0 or 1, R8 corresponds to a linear, branched or cyclic alkyl radical having 1 to 4 C atoms, E corresponds to a radical R8*—Ym—(CH2)s—, with R8* corresponding to a mono-, oligo- or perfluorinated alkyl radical having 1 to 9 C atoms or to a mono-, oligo- or perfluorinated aryl radical, and Y corresponding to a CH2, O, aryl or S radical, and m being 0 or 1 and s being 0 or 2, or to a vinyl, allyl or isopropenyl radical, mercaptoalkyl radical, sulfanealkyl radical, ureidoalkyl radical, to an acryloyloxyalkyl radical or to a linear, branched or cyclic alkoxy radical having 1 to 4 C atoms and R9 corresponds to a linear, branched and/or cyclic alkyl radical having 1 to 4 C atoms, and/or the condensates thereof, are initially introduced
- and are at least partly hydrolyzed in the presence of water and in the presence of an acid and/or of a catalyst and water and optionally of a solvent and
- then, in a second hydrolysis step,
- in the presence of further water and optionally of further acid,
- at least one bisaminoalkoxysilane of the formula II
- (OR1)3Si-A-Si(OR1)3 (II)
- where A is a bis-aminofunctional group of the formula III
- —(CH2)i—[NH[(CH2)f]gNH[(CH2)f*NH]g*—(CH2)i*— (III),
- in which i, i*, f, f*, g or g* are identical or different, with i and/or i*=from 0 to 8, f and/or f*=1, 2 or 3, g and/or g*=0, 1 or 2 and R1 corresponds to a linear, cyclic and/or branched alkyl radical having 1 to 4 C atoms, and/or the condensates thereof, and optionally
- at least one aminoalkylalkoxysilane of the formula IV
- B—Si(R3)x(OR2)3-x (IV)
- where x=0 or 1, R2 corresponds to a linear, branched and/or cyclic alkyl radical having 1 to 4 C atoms and B corresponds to one of the following aminofunctional groups of the general formula Va or Vb
- R10h*NH(2-h*)[(CH2)h(NH)]j[(CH2)l(NH)]n—(CH2)k— (Va),
- in which 0≦h≦6;
- h*=0, 1 or 2, j=0, 1 or 2;
- 0≦l≦6;
- n=0, 1 or 2;
- 0≦k≦6 and R10 corresponds to a benzyl, aryl, vinyl or formyl radical and/or to a linear, branched and/or cyclic alkyl radical having 1 to 8 C atoms, and/or
- [NH2(CH2)m]2N(CH2)p— (Vb),
- in which 0≦m≦6 and 0≦p≦6, and/or the condensates thereof, are added
- and are hydrolyzed and the alcohol is substantially removed.
26 more elements
Dependencies are inferred from the claim text.