CN111117410B - High-water-resistance primer for silane modified building sealant - Google Patents

High-water-resistance primer for silane modified building sealant Download PDF

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CN111117410B
CN111117410B CN201811285046.7A CN201811285046A CN111117410B CN 111117410 B CN111117410 B CN 111117410B CN 201811285046 A CN201811285046 A CN 201811285046A CN 111117410 B CN111117410 B CN 111117410B
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娄从江
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D147/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Coating compositions based on derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D115/00—Coating compositions based on rubber derivatives
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/002—Priming paints
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic

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Abstract

The invention discloses a high water resistance primer for silane modified building sealant, which comprises the following components in percentage by mass: 5 to 50 percent of alkoxy modified polymer (A), 3 to 50 percent of cross-linking agent (B), 0.5 to 10 percent of silane coupling agent (C), 0 to 2 percent of catalyst (D) and 10 to 90 percent of solvent (E). The primer can be used for pretreating a porous base material jointed by silane modified building sealant, because the primer is volatilized after being applied, and is hydrolyzed and crosslinked by siloxane groups after being cured in the presence of moisture to form a film on a bonding interface of the porous base material, the cured film-forming high polymer contains a large amount of non-polar main chain structures, has excellent hydrolysis resistance, and the siloxane cured bonding point and the jointed sealant have excellent bonding compatibility, the bonding capability between the sealant and the base material can be improved, and the primer is suitable for most commercially available silane modified sealants, such as Modified Silicone (MS), silane terminated polyurethane (SPU), Silane Terminated Polyether (STPE) and other sealants.

Description

High-water-resistance primer for silane modified building sealant
Technical Field
The invention relates to a primer, in particular to a high-water-resistance primer for silane modified building sealant; belongs to the technical field of materials.
Background
The building sealant is an adhesive used for firmly adhering different building materials, and most of the building sealant has good adhesiveness. However, due to the wide range and diversity of the bonding objects and the uncertainty of the using conditions, the building sealant needs to use a primer (or primer liquid) to improve the bonding effect of the sealant and the base material in the practical use, and the practice also proves that satisfactory bonding strength and bonding stability can be obtained by using the primer at the bonding parts with higher requirements on the bonding effect.
Both domestic and foreign purposes are dedicated to optimizing and improving the performance of the primer. Adhesion promoter compositions as disclosed in PCT application WO 2007/035255, are advantageously used to improve the adhesion of silylated polymeric sealant/adhesive/coatings on various substrates such as wet or dry concrete. The Chinese invention patent with the application number of 2014108307412 discloses a primer coating for silane modified polyether sealant and a preparation method thereof, wherein the primer coating can be directly coated on an adhered base material, and a sizing process is carried out on the surface of the base material after several minutes, so that the adhesive strength between the silane modified polyether sealant and the base material can be enhanced, even if the base material is soaked in water for a long time, the silane modified polyether sealant is completely adhered on the base material, but the polarity of organic silicon resin is high, and the primer coating has the defects of poor low-temperature flexibility and poor adhesion compatibility with silane modified sealants. Chinese patent publication No. CN 107474726 a discloses a primer which has poor water resistance and hydrolysis resistance, especially, the alkalinity of concrete after meeting water increases the risk of adhesive failure in the long-term water environment.
In view of the above, it is necessary to develop a primer having high water resistance and alkali resistance.
Disclosure of Invention
In order to solve the defects of the prior art, the invention aims to provide a silane modified primer composition for building sealants, which introduces a large amount of nonpolar polyolefin chain segments into a main chain structure through polymer structure design, so that the primer composition has excellent water resistance and hydrolysis resistance after being cured by moisture in air, and can ensure long-term bonding reliability of the sealant in waterproof sealing of an outer wall.
In order to achieve the above object, the present invention adopts the following technical solutions:
the primer for the silane modified building sealant is characterized by comprising the following components in parts by weight:
5 to 50 mass percent of an alkoxy modified polymer (A),
3 to 50 mass percent of cross-linking agent (B),
0.5 to 10 mass percent of silane coupling agent (C) as an adhesion promoter,
0 to 2 mass percent of catalyst (D),
and 10 to 90 mass percent of a solvent (E);
the sum of the mass percentages of the five components is 100 percent.
Preferably, the alkoxy modified polymer (A) is a mixture of one or more specific structures in the formula I (a) or I (b):
Figure BDA0001848550080000021
-wherein R1Represents a divalent group of a hydrocarbon group having 2 to 100 carbon atoms, which is an aliphatic alkane, an aromatic-substituted alkane or an unsaturated alkene, when R is1In the case of unsaturated olefin structures, the unsaturated double bond is in the main chain or in the substituted branch, orThe substituted alkyl group is distributed on the main chain and the substituted branched chain simultaneously;
-R2represents an aliphatic or aromatic substituted alkylene divalent radical comprising 1 or 3 or more carbon atoms, preferably R2Is propylene;
-R3and R4Are the same or different and each represents a straight-chain or branched alkyl group containing 1 to 4 carbon atoms when a plurality of R's are present3Or R4When groups are present, these groups are the same or different; r4Preferably methyl;
-R5one or a mixture of divalent radicals of the following structure, preferably R5Is one of d, e, f, g, h structures:
Figure BDA0001848550080000031
-R6and R71 or 2 of which are of formula II:
-R2a-Si(R3a)p1(OR4a)3-p1
II
in the formula II, the reaction mixture is shown in the specification,
-R2arepresents an aliphatic or aromatic substituted alkylene divalent group containing 1, 3 or more carbon atoms; preferably a divalent methylene group or a divalent n-propyl group, more preferably an n-propyl group;
-R3aand R4aAre the same or different and each represents a straight-chain or branched alkyl group containing 1 to 4 carbon atoms when a plurality of R's are present3aOr R4aWhen the radicals are the same or different, R4aPreferably methyl or ethyl, more preferably methyl;
-p1 is equal to 0 or 1 or 2, preferably 0 or 1, more preferably 0.
When R is6Or R7When only one of them is of formula II, then the other is a hydrogen atom or a group containing 1 to 10 carbon atoms, of aromatic, aliphatic or cycloaliphatic structure; preference is given toIs n-butyl, cyclohexyl, n-octyl or phenyl.
-n1 is an integer such that the repeat unit is- (R)1)n1The polymeric hydrocarbons of (A) have a number average molecular weight of from 300g/mol to 80000 g/mol;
-m1 is an integer including 0, such that the siloxane-modified polymer (a) having formula i (a) has a number average molecular weight of from 300g/mol to 100000 g/mol;
-m2 is an integer other than 0, so that the siloxane-modified polymer (A) of formula I (b) has a number average molecular weight of from 300g/mol to 100000 g/mol.
Preferably, the (R) is1)n1More preferably, the segmented structure of the saturated or unsaturated polyolefin comprises four structures of III (a), III (b), III (c) and III (d):
Figure BDA0001848550080000041
-wherein the repeating segments of III (a), III (b), III (c) and III (d) are in random order, or in block order, optionally in random arrangement; III (c) segment Structure there may be a structure of two cis-trans isomers III (c1) and III (c2), which are preferably randomly distributed throughout the backbone.
Figure BDA0001848550080000042
-Ra、Rb、Rc、Rd、Re、Rf、Rg、Rh、RjAnd RkAre identical or different and each represents an H atom or a hydrocarbon radical having from 1 to 20 carbon atoms, is of aromatic, aliphatic or cycloaliphatic structure, when several R's are presenta、Rb、Rc、Rd、Re、Rf、Rg、Rh、RjOr RkWhen groups are present, these groups are the same or different;
the molar contents of the corresponding monomer structures of (a), (b), (c), (d) and (e) in the molecular chain are represented by x1, x2, x3 and x4, respectively, are decimal fractions of 0 to 1, and satisfy x1+ x2+ x3+ x4 ═ 1;
possible stereoisomers in this formula are not specified, but are included within the scope of the present invention.
As a specific preferred structure, the alkoxy modified polymer (A) has the structure of formula I (a), and is prepared by the following steps: using a compound of the formula OCN-Rt1-Si(ORt2)t'(Rt3)3-t'With a hydroxyl-terminated polyolefin, according to the NCO: OH ═ 1:1 (molar ratio), reacting for 3 hours at 70-90 ℃ in the atmosphere of nitrogen protection to obtain the silane modified polymer with the structure of formula I (a).
-wherein R ist1Represents a linear or branched alkylene chain having 1 to 4 carbon atoms, and Rt2And Rt3Simultaneously or independently of one another, represents a linear or branched alkyl chain having 1 to 5 carbon atoms. Preferred Rt1Represents a divalent methylene group (-CH)2-) or a divalent n-propyl (-CH)2CH2CH2-, more preferably Rt1Represents a divalent n-propyl group; rt2Preferably a monovalent methyl or ethyl group, more preferably a methyl group; rt3Preferably methyl;
-t' is 1, 2 or 3, optionally 2 or 3, more preferably 3;
hydroxyl-terminated polyolefins, which may be selected from hydroxyl-terminated polybutadiene, hydroxyl-terminated polyisoprene, hydroxyl-terminated butadiene-styrene copolymers, hydroxyl-terminated polylaurene, hydroxyl-terminated poly-1-butene, hydroxyl-terminated polyisobutylene, hydroxyl-terminated poly-1-octene, etc., preferably hydroxyl-terminated polymers or copolymers of conjugated olefin-containing monomers, which are polymerized or copolymerized by free radicals or living radicals.
The more specific preparation method comprises the following steps: using isocyanatopropyltrimethoxysilane (O ═ C ═ N- (CH)2)3-Si(OCH3)3) With hydroxy-terminated liquid polybutadiene (HTPB) as starting material, according to NCO: OH ═ 1:1 (molar ratio), reacting for 3 hours at 80-90 ℃ in the atmosphere of nitrogen protection to obtain a structure with a formula I (a)The silane-modified polymer of (1).
One skilled in the art can also refer to the process described in WO2016/180649 for preparing alkoxy-modified polymers (A) having the structure of formula I (a).
In addition, alkoxy-modified polymers (A) of the formula I (a) are also commercially available on the market, for example
Figure BDA0001848550080000051
EP ST-M and
Figure BDA0001848550080000052
EP ST-E100, two products are commercially available from the company EVONIK. Wherein the content of the first and second substances,
Figure BDA0001848550080000053
EP ST-M is a liquid trimethoxy silane-terminated polybutadiene of the formula I (a)2Is n-propyl- (CH)2)3-，p＝0，R4Is methyl-CH3M1 ═ 0, i.e. in formula III, Ra、Rb、Rc、Rd、ReAnd RfAll are H atoms, the range of x1+ x2 is 10-60%, and the range of x3 is 40-90%; x4 ═ 0; wherein the unit structure with molar content x3 is-CH 2-CH 2-, which has the following two isomeric forms:
Figure BDA0001848550080000061
in addition, n1 in structural formula I (a) is a positive integer such that the repeating unit is R1The number average molecular weight of the hydrocarbon polymer of (2) is preferably in the range of 1000g/mol to 8000 g/mol.
As another specific structure, the alkoxy-modified polymer (a) has the structure of formula i (b), and is typically prepared by the following steps: using hydroxyl terminated polyolefins as starting material, e.g. hydroxyl terminated polybutadiene, hydroxyl terminated polyisoprene, hydroxyl terminated butadiene-styrene copolymers, hydroxyl terminated polylaurenes, etc. hydroxyl terminated polymerization of conjugated olefin containing monomersThe raw material of the compound or the copolymer is firstly reacted with OCN-R under the protection of nitrogen at the temperature of 70-80 DEG C5-NCO reaction for 3 hours with NCO: OH ═ 2.0:1 to 2.1: preparing isocyanate-terminated polyolefin according to a molar ratio of 1, measuring the NCO content according to a standard, cooling to room temperature under the protection of nitrogen when the NCO content reaches a set value, adding quantitative siloxane containing secondary amino functional groups such as N- (N-butyl) -gamma-aminopropyltrimethoxysilane or N- (cyclohexyl) -gamma-aminopropyltrimethoxysilane or N- (phenyl) -gamma-aminopropyltrimethoxysilane or N- (octyl) -gamma-aminopropyltrimethoxysilane or di (N-propyltrimethoxysilane) amine and the like into the isocyanate-terminated polyolefin prepolymer for reaction, and reacting the isocyanate-terminated polyolefin prepolymer according to the NCO/═ NH ratio of 1:1 to 1: 1.1, carrying out siloxane capping on the isocyanate-terminated polyhydrocarbon prepolymer to obtain the silane modified polymer with the structure of formula I (b).
Still more preferably, the aforementioned R5Is a divalent hydrocarbon radical of 6 to 20 carbon atoms, which may be aliphatic, cycloaliphatic or aromatic, preferably one of the structures b, c, d, e, f, g, h, such as TDI (b, c), MDI (d, e), IPDI (f), HDI (g) or HMDI (h).
Preferably, the aforementioned crosslinking agent (B) is a small molecule silane or a polymer of alkoxysilanes containing 3 or more alkoxysilyl functional groups. Can be selected from one or more of vinyltrimethoxysilane, tetramethyl silicate, tetramethyl disilicate, methyltrimethoxysilane, phenyltrimethoxysilane, n-octyltrimethoxysilane, isooctyltrimethoxysilane, isocyanatopropyltrimethoxysilane, an adduct of aminosilane and epoxysilane, a hydrosilylation adduct of methacrylate silane and hydrosiloxane, and a trimer of isocyanate silane.
More preferably, the primer crosslinker (B) is a polyalkoxysilane-containing polymerization product having the formula IV:
Figure BDA0001848550080000071
-wherein R islTo RwAnd Ra1And Ra2Are identical or different and are hydrogen atoms or radicalsFrom the following groups: a linear or branched C1-C4 alkyl group, a linear or branched alkyl group containing 1 to 30 carbon atoms, a mono or polyalkenyl group containing 2 to 30 carbon atoms, an aromatic group containing 6 to 30 carbon atoms, an alicyclic group containing 3 to 30 carbon atoms;
-Rza hydrocarbon group of 7 to 30 carbon atoms which is a divalent saturated straight or branched alkane group of 1 to 30 carbon atoms, or a branched hydrocarbon group of 7 to 30 carbon atoms which contains an aromatic substituent or an alicyclic hindered alkane or alkene;
-y1to y6Represents a decimal of 0 to 1 which is not 0, and indicates the molar ratio content of chain segments with different structures, and satisfies y1+y2+y3+y4+y5+y61, and y2、y4And y6At least one of which is not 0;
-R6b，R7brepresents a hydrogen atom or a group containing more than 1 carbon atom, which may be aromatic or linear or branched or of an alicyclic structure, R6And R7At least one or both of which are of structure V:
-R2b-Si(R3b)p2(OR4b)3-p2
V
in the formula V, R2bRepresents a linear or branched or aromatic substituted alkylene divalent group of 1 or 3 or more carbon atoms; preferably a divalent methylene group or a divalent n-propyl group, more preferably an n-propyl group.
-R3bAnd R4bWhich are identical or different and each represent a linear or branched alkyl group having from 1 to 4 carbon atoms, when several R's are present3dOr R4dWhen these groups are the same or different; r4bPreferably a monovalent methyl or ethyl group, more preferably a methyl group; r3bMonovalent methyl groups are preferred.
-p2 is equal to 0 or 1 or 2; preferably 0 or 1, more preferably 0;
-mais an integer other than 0; number of the primer crosslinking agent (B)The average molecular weight is 300 g/mol-300000 g/mol.
Preferably, the crosslinking agent (B) having the structure of formula (V) is obtainable by the following process steps:
1) selecting polyolefin containing unsaturated double bonds with a structure shown in formula II, such as polybutadiene, polyisoprene, polybutadiene-styrene copolymer, polylauric acid alkene, etc., preferably liquid polyolefin with high double bond content and high molecular weight and small viscosity;
2) heating to react in an initiator-free system, grafting a certain amount of maleic anhydride onto the polyolefin chain containing the unsaturated double bond through a circumferential reaction mechanism such as an Ene reaction and a Diels-Alder reaction. The preferred molar ratio of maleic anhydride to polyolefin is in the range of 1.5 to 5.0. More preferably in the range of 2 to 4.
For more details of the preparation reference may be made to:
B.C.Trivedi.Maleic Anhydride.New York：Plenum Press.1982：P147—149；
H.M.R.Hoffrnan Angew.Ene reaction.Chem.Internal，Edil...1969.8(8)：P556～577.
maleic anhydride-modified polyolefin available on the market, optionally
Figure BDA0001848550080000081
MA 75 (commercially available from EVONIK) or
Figure BDA0001848550080000082
130MA8，
Figure BDA0001848550080000083
142MA3 (commercially available CRAY VALLEY);
3) the maleic anhydride modified polyolefin is diluted with a slight excess of HN (R)6b)(R7b) The alpha, beta or gamma-aminosilane containing the secondary amino group reacts to obtain the cross-linking agent (B) with the structure of the formula (V).
The silane coupling agent (C) is used as a water-removing stabilizer or an adhesion promoter, and is selected from one or more of trimethoxy silane, triethoxy silane, or dimethoxy silane containing a hydrocarbon group, an amino group, a mercapto group, a methacrylate group, or an epoxy group, and partially hydrolyzed oligomer of silane containing the above groups or reaction product of silane containing the above groups and other compounds, such as vinyltrimethoxysilane, phenyltrimethoxysilane, aminopropyltrimethoxysilane, aminopropyltriethoxysilane, N- (beta-aminoethyl) -gamma-aminopropyltrimethoxysilane, N- (beta-aminoethyl) -gamma-aminopropyldimethoxymethylsilane, di (gamma-trimethoxysilylpropyl) amine, N- (N-butyl) -gamma-aminopropyltrimethoxysilane, or N- (phenyl) -gamma-aminopropyltrimethoxysilane Propyl trimethoxy silane; mercaptopropyltrimethoxysilane, methacrylate-propyltrimethoxysilane, gamma-glycideth-propyltrimethoxysilane, or the like, or a partially hydrolyzed oligomer of a vinyl silane, a partially hydrolyzed oligomer of an aminosilane, or a partially hydrolyzed copolymer of an aminosilane and a hydrocarbyl silane, or a reaction product of an aminosilane and an epoxy silane, or the like.
Still more preferably, the water removal stabilizer is selected from vinyltrimethoxysilane or phenyltrimethoxysilane; the adhesion promoter is one or more of trimethoxy silane with amino or epoxy groups.
Still preferably, the aforementioned catalyst (D) may be selected from any catalysts known to those skilled in the art for silanol condensation. As a practical use, amines or organic technical derivatives can be chosen, in particular organic derivatives of titanium, bismuth, aluminum, zinc, zirconium or divalent or tetravalent tin. Commercially available catalysts are for example:
from Dorf Ketal, e.g.
Figure BDA0001848550080000084
726, a catalyst based on titanium ethyl acetoacetate complex;
from Evonik, e.g.
Figure BDA0001848550080000091
T-12, dibutyltin dilaurate;
dibutyltin compounds from TIB, such as TIB KAT 226, or from nitto compounds, such as U-220H, based on acetylacetone complexation;
catalysts based on bismuth carboxylates from the Ridong chemical industry, for example U-600.
Preferably, the aforementioned solvent (E) is selected from a mixture of one or more of hydrocarbons, esters or ketones, the ester solvent is selected from one or more of ethyl acetate and butyl acetate, the hydrocarbon solvent is selected from one or more of toluene, xylene, hexane, heptane and cyclohexane, and the ketone solvent is selected from one or more of acetone and methyl ethyl ketone.
More preferred solvents (E) satisfy the condition that the range of m (E)/m (undercoat) is within a range of 50% to 90%, preferably within a range of 65% to 85%, m (E) means the mass of the solvent (E) in the undercoat, m (undercoat) means the total mass of the undercoat, and the range of [ m (A) + m (B) ]/m (undercoat) is within a range of 10% to 50%, more preferably within a range of 15% to 30%;
the preparation method of the primer for the silane modified building sealant comprises the following specific steps: fully dissolving the alkoxy modified polymer (A) and the cross-linking agent (B) in the solvent (E), then adding the adhesion promoter (C), uniformly stirring, and finally adding the catalyst (D) to prepare the primer.
The primer for silane-modified type building sealants as described above has excellent application prospects in pretreating porous substrates which are expected to be joined by a moisture-curable silane-modified type sealant, including but not limited to reinforced concrete, precast concrete panels, plaster, aerated concrete, calcium silicate boards, absorbent clinker, ceramics, garden paving stones or facing bricks, and the like.
The invention has the advantages that:
the primer composition can be used for pretreating porous base materials jointed by silane modified building sealants, and has excellent hydrolysis resistance and efficient barrier property and excellent bonding compatibility with jointed sealants due to the fact that the primer penetrates through interface pores, can effectively block pores of a bonding interface after being cured when meeting moisture, and has excellent bonding compatibility with the jointed sealants after the porous base materials are bonded with the interface films, so that the primer composition can optimize the bonding performance between the sealants and the base materials, is suitable for most commercially available silane modified sealants, such as Modified Silicone (MS), silane terminated polyurethane (SPU), Silane Terminated Polyether (STPE) and the like, and can effectively solve the problem of bonding between the existing silane modified polymer sealants and porous fragile interfaces such as concrete and the like, particularly the problem of water soaking bonding and the like.
Detailed Description
The present invention will be described in detail with reference to the following embodiments.
Example 1
Figure BDA0001848550080000092
Figure BDA0001848550080000101
Table 1 specific selection and mass percentages of the components in example 1
In this example 1, the silane-modified polymer (a) is a silane-terminated polybutadiene of formula i (a), i.e., formula i (a) wherein m1 is 0, R2is-CH2CH2CH2-，p＝0,R4is-CH 3;
in the formula III, Ra，Rb，Rc，Rd，ReAnd RfAll are H atoms, the range of x1+ x2 is 10-60%, and the range of x3 is 40-90%; x4 ═ 0; wherein the unit structure with a molar content of x 3-CH 2-CH ═ CH-CH2-, has the following two isomeric forms:
Figure BDA0001848550080000102
in the present embodiment, a commercially available Evonik product is selected
Figure BDA0001848550080000103
EP ST-M as silane-modified Polymer (A) is a trimethoxysiloxane-terminated polybutadiene having a number-average molecular weight of 3500g/mol and siliconThe average functionality of the alkylene oxide is 6.9 to 7.2.
The cross-linking agent (B) is a polysiloxane polymer with a structure shown in formula IV and can be obtained by the following steps:
1) selecting
Figure BDA0001848550080000104
MA 75 (commercially available from EVONIK, having a backbone structure of high 1, 4-polymerized liquid polybutadiene obtained by Ziegler reaction, having a number average molecular weight of about 2600g/mol, modified by grafting with maleic anhydride, having a maleic anhydride content of 7.5% and a molar ratio of maleic anhydride to polyolefin of about 2.1), siloxane-terminated polymer (A) prepared using the above with
Figure BDA0001848550080000105
Fully and uniformly mixing MA 75, and diluting;
2) n- (phenyl) -gamma-aminopropyltrimethoxysilane was added in three equal portions, according to the weight ratio of maleic anhydride: reacting NH (1: 2.1) at normal temperature for about 2 hours under the protection of nitrogen, and adding vinyl trimethoxy silane for stabilization; finally, a mixture of the polyalkoxy group-containing primer crosslinking agent (B) having a pale yellow tackiness was obtained. (in the formula IV, RlTo R DEG are each H atom, y5And y6Is 0, y1+y2＝0.99，y3+y4＝0.01；R6bIs phenyl-C6H5，R7bIs n-propyltrimethoxysilane-CH2CH2CH2Si(OCH3)3I.e. R in formula V2bIs n-propyl R4bIs methyl-CH 3, p2 ═ 0).
The primer of the embodiment is prepared by the following specific steps: fully dissolving the mixture of the alkoxy modified polymer (A) and the cross-linking agent (B) in the solvent (E), then adding the silane coupling agent (C), uniformly stirring, and finally adding the catalyst (D) to prepare the primer.
Example 2
Figure BDA0001848550080000111
Table 2 specific selection and mass percentages of the components in example 2
The silane-modified polymer (A) is a silane-terminated polybutadiene of the formula I (a)
Figure BDA0001848550080000112
EP ST-M。
Figure BDA0001848550080000113
1146 is a commercial product of EVONIK, and is an oligomer obtained by copolymerizing aminosilane and alkylsilane, as the silane coupling agent (C) in the present example.
The preparation steps are the same as example 1 and are not repeated herein.
Example 3
Figure BDA0001848550080000114
Figure BDA0001848550080000121
Table 3 specific selection and mass percentages of the components in example 3
In this example 3, the silane-modified polymer (a) is a silane-modified polyisoprene of formula i (b) prepared by the process of: hydroxyl-terminated Polybutadiene (POLY) with hydroxyl-terminated isoprene (1, 2 addition structure is dominant, molecular weight is 30000,)
Figure BDA0001848550080000122
R-15, commercially available from U.S. CRAY VALLEY, obtained by free radical polymerization, has a number average molecular weight of 2500 to 2800mol/g and an average hydroxyl functionality of 2.2 to 2.6) is prepared according to a ratio of 1:1 is heated to 110 ℃, stirred and dehydrated for 2h in vacuum, cooled to room temperature, and the obtained mixture of hydroxyl-terminated polybutadiene and hydroxyl-terminated polyisoprene, which is used as a raw material, is firstly reacted with TDI (toluene diisocyanate, commercially available) for 3 h under the protection of nitrogen at 70-80 ℃, and NCO: OH 2.05:1 mol is adoptedPreparing isocyanate-terminated poly-mixed olefin, measuring the NCO content according to the standard, cooling to room temperature under the protection of nitrogen when the NCO content reaches a set value, diluting by 15 mass percent of solvent (E), adding quantitative N- (N-butyl) -gamma-aminopropyltrimethoxysilane to react with isocyanate-terminated poly-mixed polyolefin prepolymer, and reacting according to the conditions that NCO/═ NH is 1: 1.02 to obtain the silane modified polymer with the structure of the formula I (b). Wherein in the structural formula of (I), (b), R5Is a mixture of b and c, and the mass ratio of b to c is 80/20; r6Is n-butyl-CH2CH2CH2CH3；R7Is propyl trimethoxy silicon-CH2CH2CH2Si(OCH3)3I.e. R in formula II2aIs n-propyl, p1 ═ 0, R4aIs methyl; there are two structures in formula III: (1) rc is methyl, Ra，Rb，Rd，ReAnd RfAre all H atoms; x 4-0, x1+ x2 ranging from 80% to 95%, x3 ranging from 5% to 20%, and m 2-1, n1 having such a value that the number average molecular weight of polyolefin whose structural unit is isoprene (R1) n1 is 30000 g/mol. (2) In the formula III, Ra，Rb，Rc，Rd，ReAnd RfAll are H atoms, the range of x1+ x2 is 10-60%, and the range of x3 is 40-90%; x4 is 0 and m2 is 1, n1 has such a value that the number average molecular weight of the polyolefin whose structural unit is butadiene (R1) n1 is 2200 to 2600g/mol
Other preparation steps are the same as example 1, and are not described herein.
Example 4
Figure BDA0001848550080000123
Figure BDA0001848550080000131
Table 4 specific selection and mass percentages of the components in example 4
In this example 4, the silane-modified polyThe compound (A) is silane modified polybutadiene of formula I (b), R in formula IIIa，Rb，Rc，Rd，ReAnd RfAll are H atoms, the range of x1+ x2 is 10-60%, and the range of x3 is 40-90%; x4 ═ 0; the molar content of which is x32-CH＝CH-CH2-, having the following two isomeric forms:
Figure BDA0001848550080000132
specifically, in this example, POLY, a commercially available product of US CRAY VALLEY, was selected
Figure BDA0001848550080000133
R45V was used as starting material and MDI-50 (commercially available) was first reacted for 3 hours at 70-80 ℃ under nitrogen with NCO: OH ═ 2.0:1 to 2.1: preparing isocyanate-terminated polybutadiene according to a molar ratio of 1, measuring the NCO content according to a standard, cooling to room temperature under the protection of nitrogen when the NCO content reaches a set value, adding a certain amount of di (n-propyltrimethoxy silicon) amine to react with an isocyanate-terminated polybutadiene prepolymer, and reacting according to the NCO/═ NH ratio of 1: 1.1, carrying out silanization end capping on the isocyanate end-capped polyisoprene prepolymer to obtain the silane modified polymer with the structure of formula I (b). Wherein in (I), (b), R5 is d, the structural proportion of e is 50/50, R6And R7Are all propyl trimethoxy silicon-CH2CH2CH2Si(OCH3)3I.e. R in formula II2aIs n-propyl, p1 ═ 0, R4aIs methyl; in the formula III, Ra，Rb，Rc，Rd，ReAnd RfAre all H atoms; x4 ═ 0, x1+ x2 in the range 80% to 95%, x3 in the range 5% to 20%, m2 ═ 1, n1 values such that the structural unit is a polyolefin of isoprene (R2 ═ 1, n11)n1The number average molecular weight of (2) is 2800 g/mol.
Other preparation steps are the same as example 1, and are not described herein.
Example 5
Figure BDA0001848550080000134
Figure BDA0001848550080000141
Table 5 specific selection and mass percentages of the components in example 5
In this example 1, the silane-modified polymer (a) is a siloxane-modified liquid poly (styrene-butadiene) rubber of the formula i (a) wherein m1 is 0 and R is2is-CH2CH2CH2-，p＝0,R4is-CH 3;
in the formula III, Ra，Rb，Rc，Rd，ReAnd Rf，Rg，Rh，RjAre all H atoms, RkIs phenyl; the range of x1+ x2 is 10-50%, and the range of x3 is 40-80%; the range of x4 is 8% -20%; wherein the unit structure with a molar content of x 3-CH 2-CH ═ CH-CH2-, has the following two isomeric forms:
Figure BDA0001848550080000142
selecting a commercial product HTBS-2 from a Zibozilong chemical industry, wherein the number average molecular weight of the product HTBS-2 is 2500g/mol, and stirring and reacting the HTBS-2 product with isocyanate propyl trimethoxy silane (IPTMS) for 3 hours under the condition of nitrogen protection at 70-80 ℃ according to the molar ratio of OH to NCO being 1:1 to obtain a siloxane modified polymer A shown in a formula I (a), wherein the siloxane modified polymer A is siloxane modified poly-styrene-butadiene liquid rubber.
The preparation steps are the same as example 1 and are not repeated herein.
Comparative example 1
The comparative examples in the present invention are: the substrate was cleaned to remove the fly ash from the bonded surface and then test sample preparation and curing (i.e. without primer) was carried out according to JC/T881 standard using the test control glue from test 4 below.
Comparative example 2
A small-molecule cross-linking agent is used, and the content of the alkoxy modified polymer (A) is less than 5 percent.
Figure BDA0001848550080000151
Table 6 specific selection and mass percentages of the components in comparative example 2
Performance detection
Testing the substrate: the cement mortar base material is required to meet the requirements on the test base material in GB/T13477.1-2002 test method for building sealing materials part 1;
testing the comparison sealant: the commercial mainstream low-modulus silane modified building sealant is adopted, and three different silane end-capped polymer (SMP) technologies are applied to four sealants;
SMP sealant-1: based on Japanese Brillouin chemistry (KANEKA)
Figure BDA0001848550080000152
Polymer technology, single component, low modulus;
SMP sealant-1.2: based on Japanese Brillouin chemistry (KANEKA)
Figure BDA0001848550080000153
The polymer technology, double components, low modulus, 25 displacement capability (meeting the requirements of JCT/881-2017 II 25 LM);
SMP sealant-2: the SPUR + polymer technology based on the motion map (Momentive) is single-component, low in modulus and 20 in displacement capacity (meeting the requirements of JCT/881-2017I 20 LM);
SMP sealant-3: STP-E polymer technology based on Wacker chemical in Germany, one-component, low modulus, 25 displacement capability (meeting the requirements of JCT/881-.
The test is carried out according to the requirements of JC/T881-2017 building sealant for concrete joint, and the test is carried out according to the requirement of displacement capacity grading shown by commercially available contrast test sealant.
When the examples are applied, the primer composition is applied to the porous substrate in a manner such as by simple brushing, and after curing, the cured composition covering the surface of the substrate is capable of forming a uniform film having a thickness generally in the range of from 5 to 300 μm, preferably in the range of from 20 to 200 μm.
The test pieces were tested for the following properties:
(1) tensile adhesion: according to GB/T13477.8-2017 building sealant test method part 8: determination of tensile adhesion, recording the failure mode of the test piece (cohesive failure CF or adhesive failure AF);
(2) tensile adhesion after soaking: according to GB/T13477.9-2017 building sealant test method part 9: measuring the tensile adhesion after soaking, and recording the failure mode (cohesive failure CF or adhesive failure AF) of the test piece;
(3) setting and stretching cohesiveness: according to GB/T13477.10-2017 building sealant test method part 10: and (4) measuring the stretching adhesiveness.
(4) And (3) the fixed-extension cohesiveness after soaking: in accordance with GBT 13477.11-2017 building sealant test method part 11: and (4) measuring the definite elongation caking property after soaking in water.
(5) Water absorption and corrosion resistance: referring to the determination of water absorption rate in the national standard GB/T19250-. The fully cured film was cut to 50mm x 50mm dimensions and water absorption measurements were performed (soaking in deionized water, alkaline water and acid water, respectively, formulated according to the acid and alkaline treatment specified in standard GB/T19250-2013, at room temperature, 23 ℃ ± 2 ℃, for 1 week, 168 hours).
Figure BDA0001848550080000161
From the above test results, the coating film of the primer of the present invention has very low water absorption rate and excellent hydrophobic property; after being treated by alkali liquor and acid liquor, the water absorption rate is less than 1 percent, and the water-based paint has very good acid and alkali resistance, and particularly has very excellent alkali corrosion resistance (the water absorption rate of alkali treatment is less than 0.5 percent). Because the system contains the amino silane coupling agent which can react with the acid liquor, the surface of the coating film can be yellowed after being treated by the acid liquor, but the film-forming high polymer contains a large amount of nonpolar polyolefin chain segments, has very low water permeability, prevents the polar acid liquor from further permeating, and ensures lower water absorption.
The results of the tests for other properties are shown in Table 7:
Figure BDA0001848550080000162
Figure BDA0001848550080000171
TABLE 7 comparison of the results of the tests on the properties of the examples and comparative examples (where the sheet failure is calculated as cohesive failure)
As can be seen from table 7 above, the main chain of the silane modified polymer (a) is a nonpolar or low-polar polyolefin main chain, and forms a hydrophobic high polymer film with siloxane crosslinking points after being cured by moisture with other base coat components, and the film has excellent water resistance, hydrolysis resistance, and high-efficiency barrier property, and has excellent adhesion compatibility with the adhesive sealant. The base coat forms a high polymer film with coupling effect between the sealant and the bonding base material, so that the corrosion of alkaline medium formed after the concrete meets water to the bonding interface is prevented, and the bonding of the silane modified sealant on porous weak interfaces such as concrete is ensured. Comparative example 1 is directly applied under the condition of not applying a base coat, except for a two-component MS system, other single-component sealants have better bonding performance under the anhydrous state, but serious bonding problems occur after soaking in water, except for the reason of a concrete base material, the sealant belongs to a paste with higher viscosity, has no fluidity, has poor wettability on a porous base material, does not block a large number of pores on a concrete interface, and due to the capillary effect of the pores after meeting with water, a large amount of alkaline aqueous solution enters the bonding interface layer to corrode the bonding interface between the sealant and the concrete, and the concrete softens and expands after meeting with water to generate stress concentration on the bonding interface so as to seriously damage bonding.
In comparative example 2, the content of the silane modified polymer (A) is low, the crosslinking agent B is a micromolecular crosslinking agent, the permeability of the bottom coat is strong, most of the crosslinking agent B permeates into the pores of the concrete, so that the surface film forming is incomplete, and an uncovered concrete interface is left, so that the water resistance of the concrete is seriously reduced.
In conclusion, the primer is applied to the silane modified building sealant, is particularly suitable for pretreating porous base materials jointed by the silane modified building sealant, has excellent hydrolysis resistance after being cured in the presence of moisture and forms a film on the jointing interface of the porous base materials, and has excellent adhesion compatibility with the jointed sealant, so that the adhesion performance between the sealant and the base materials can be optimized.
The foregoing illustrates and describes the principles, general features, and advantages of the present invention. It should be understood by those skilled in the art that the above embodiments do not limit the present invention in any way, and all technical solutions obtained by using equivalent alternatives or equivalent variations fall within the scope of the present invention.

Claims (7)

1. A high water resistance primer for silane modified building sealant is characterized by comprising:
5 to 50 mass percent of an alkoxy modified polymer (A),
3 to 50 mass percent of cross-linking agent (B),
0.5 to 10 mass percent of silane coupling agent (C),
0.001 to 2 mass percent of catalyst (D),
and 10 to 90 mass percent of a solvent (E);
the sum of the mass percentages of the five components is 100 percent;
wherein the content of the first and second substances,
the alkoxy modified polymer (A) is a mixture of one or more specific structures in a formula I (a) or I (b):
Figure FDA0003219063180000011
formula I (a) or I (b):
-R1represents a divalent group of a hydrocarbon group containing 2 to 100 carbon atoms, and is an aliphatic alkane, an aromatic substituted alkane or an unsaturated alkene; when R is1When the structure is unsaturated olefin, the unsaturated double bond is distributed on the main chain or the substituted branch chain, or on the main chain and the substituted branch chain simultaneously;
-R2represents an aliphatic or aromatic substituted alkylene divalent group containing 1, 3 or more carbon atoms;
-R3and R4Are the same or different and each represents a straight-chain or branched alkyl group containing 1 to 4 carbon atoms when a plurality of R's are present3Or R4When groups are present, these groups are the same or different;
-R5one or a mixture of divalent groups representing the structure:
Figure FDA0003219063180000021
-R6and R71 or 2 of which are of formula II:
-R2a-Si(R3a)p1(OR4a)3-p1
II
in the formula II, R2aRepresents a group containing 1, 3 or 3An aliphatic or aromatic substituted alkylene divalent group of more than one carbon atom;
-R3aand R4aAre the same or different and each represents a straight-chain or branched alkyl group containing 1 to 4 carbon atoms when a plurality of R's are present3aOr R4aWhen groups are present, these groups are the same or different;
-p1 is equal to 0 or 1 or 2;
when R is6Or R7When only one of them is of formula II, then the other is a hydrogen atom or a group containing 1 to 10 carbon atoms, of aromatic, aliphatic or cycloaliphatic structure;
-n1 is an integer such that the repeat unit is R1Of polymerized hydrocarbon of (A) - (R)1)n1-a number average molecular weight of 300g/mol to 80000 g/mol;
-m1 is an integer including 0, such that the siloxane-modified polymer (a) of formula i (a) has a number average molecular weight of from 300g/mol to 100000 g/mol;
-m2 is an integer different from 0, so that the siloxane-modified polymer (a) of formula i (b) has a number-average molecular weight of from 300g/mol to 100000 g/mol;
p is equal to 0 or 1 or 2;
the crosslinking agent (B) is polyolefin containing a plurality of alkoxy silane, and the structural formula is shown as a formula IV:
Figure FDA0003219063180000031
-wherein R islTo RwAnd Ra1And Ra2Are identical or different and are a hydrogen atom or a group selected from: a linear or branched alkyl group containing 1 to 30 carbon atoms, a mono-or polyalkenyl group containing 2 to 30 carbon atoms, an aromatic group containing 6 to 30 carbon atoms, an alicyclic group containing 3 to 30 carbon atoms;
-Rzis a divalent saturated straight-chain or branched alkane group containing 1 to 30 carbon atoms, or a hydrocarbon of 7 to 30 carbon atoms which is a branched alkane or alkene containing an aromatic substituent or an alicyclic hydrocarbonA pseudo group;
-y1to y6Represents a decimal of 0 to 1 which is not 0, and indicates the molar ratio content of chain segments with different structures, and satisfies y1+y2+y3+y4+y5+y61, and y2、y4And y6At least one of which is not 0;
-R6b，R7brepresents a hydrogen atom or a group containing more than 1 carbon atom, which may be aromatic or linear or branched or of an alicyclic structure, R6bAnd R7bAt least one or both of which are of structure V:
-R2b-Si(R3b)p2(OR4b)3-p2
V
in the formula V, R2bRepresents a linear or branched or aromatic substituted alkylene divalent group of 1 or more than 3 carbon atoms;
-R3band R4bWhich are identical or different and each represent a linear or branched alkyl group having from 1 to 4 carbon atoms, when several R's are present3bOr R4bWhen these groups are the same or different;
-p2 is equal to 0 or 1 or 2;
mais an integer other than 0; so that the number average molecular weight of the primer crosslinking agent (B) is 300g/mol to 300000 g/mol.
2. The primer with high water resistance for silane-modified building sealant according to claim 1, wherein the (R) is1)n1Is saturated or unsaturated polyolefin, the chain segment structure of which comprises four monomer units of III (a), III (b), III (c) and III (d):
Figure FDA0003219063180000041
wherein the repeating segments of III (a), III (b), III (c) and III (d) are in random order or block order, and the structure of the segment of III (c) has two cis-trans isomers III (c1) and III (c 2):
Figure FDA0003219063180000042
-Ra、Rb、Rc、Rd、Re、Rf、Rg、Rh、Rjand RkAre identical or different and each represents an H atom or a hydrocarbon radical having from 1 to 20 carbon atoms, is of aromatic, aliphatic or cycloaliphatic structure, when several R's are presenta、Rb、Rc、Rd、Re、Rf、Rg、Rh、RjOr RkWhen groups are present, these groups are the same or different;
the molar contents of the monomer structures of (a), (b), (c), (d) and (e) in the molecular chain are represented by x1, x2, x3 and x4, respectively, are 0 to 1 decimal number, and satisfy x1+ x2+ x3+ x4 ═ 1;
3. the primer for silane-modified building sealants according to claim 1, wherein the silane coupling agent (C) is selected from the group consisting of a mixture of one or more of trimethoxy or triethoxy or dimethoxy silane containing hydrocarbyl, amino, mercapto, methacrylate or epoxy groups, partially hydrolyzed oligomers of silanes containing the above groups, or reaction products of silanes containing the above groups with other compounds as a water removal stabilizer or adhesion promoter.
4. The primer for silane-modified building sealants according to claim 1, wherein the catalyst (D) is one or more selected from organic derivatives of Ti, Bi, Al, Zn, Zr or Bi/Sn.
5. The primer for silane-modified building sealant with high water resistance of claim 1, wherein the solvent (E) satisfies the condition that m (E)/m (primer) ranges from 50% to 90%, m (E) refers to the mass of the solvent (E) in the primer, m (primer) refers to the total mass of the primer, and the solvent (E) is selected from one or more of hydrocarbons, esters or ketones.
6. The preparation method of the high-water-resistance primer for the silane-modified building sealant as claimed in any one of claims 1 to 5, which is characterized by comprising the following specific steps: fully dissolving the alkoxy modified polymer (A) and the cross-linking agent (B) in the solvent (E), then adding the silane coupling agent (C), uniformly stirring, and finally adding the catalyst (D) to prepare the primer.
7. Use of a highly water resistant primer for silane modified type building sealants according to any one of claims 1 to 6 for pretreating porous substrates to be joined by moisture curable silane modified type sealants.
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