CN113321678B - Silane coupling agent, water-based acrylate laminating adhesive emulsion and water-based acrylate laminating adhesive - Google Patents
Silane coupling agent, water-based acrylate laminating adhesive emulsion and water-based acrylate laminating adhesive Download PDFInfo
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1896—Compounds having one or more Si-O-acyl linkages
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
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- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
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- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J143/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Adhesives based on derivatives of such polymers
- C09J143/04—Homopolymers or copolymers of monomers containing silicon
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Abstract
The invention discloses a silane coupling agent, a water-based acrylate adhesive emulsion and a water-based acrylate adhesive. The structural formula of the silane coupling agent is shown in the specification
Description
Technical Field
The invention relates to a silane coupling agent and a water-based adhesive, in particular to a water-based acrylate adhesive.
Background
The adhesive is mainly coated on the surfaces of non-woven fabrics, well woven fabrics, european style textiles, PU foam, genuine leather or PU leather and the like. The two layers of base materials are compounded after being coated, and the contact surface generates bonding force after high temperature and hot pressing, so that the adhesive is widely applied to processing of shoes, clothes and textile packaging materials.
The adhesive in the current market mainly adopts EVA emulsion, acrylate copolymer emulsion and the like. In the actual use process, the problems of low product bonding strength, poor water resistance, narrow temperature and pressure application range in the coating process and the like exist, and the operation window is low. In order to meet the requirements of industries such as shoemaking, packaging, clothing and the like, a technical scheme is required to be provided, so that the technical problems that a product coated by the water-based EVA emulsion is poor in water resistance, the bonding strength of the product coated in the acrylate emulsion product is low and the like are solved, and the prepared finished product adhesive has good coating adaptability in practical application.
In order to solve the problems, the Chinese patent CN103113838A prepares a water-based environment-friendly adhesive, but the composition is complex, the downstream construction efficiency is verified to be influenced, and the prepared finished product has low water resistance due to the EVA emulsion with poor water resistance. The Chinese patent CN104371612A prepares a multi-element polymerization adhesive for attaching polyester foam and chemical fiber cloth, the cost of the prepared emulsion synthesis formula is expensive, and compared with EVA and acrylate environment-friendly adhesive used in a downstream coating process, the cost does not have an advantage in the actual use process, and the large-scale popularization is difficult.
The surface adhesive can be applied to non-woven fabrics, well-woven fabrics, surface adhesives such as an Oucho (European Union) resistant PU foam, genuine leather or PU leather and the like, and has the advantages of better bonding strength, water-soaking resistance, coating application range and use convenience.
Disclosure of Invention
The invention provides a silane coupling agent, a water-based acrylate adhesive emulsion and a water-based acrylate adhesive. The adhesive has the characteristics of high bonding strength, good water resistance after soaking, wide application range and convenient use.
In order to realize the purpose, the technical scheme adopted by the invention is as follows:
the high-performance environment-friendly water-based acrylate laminating adhesive emulsion is prepared from the following raw materials in parts by mass:
the emulsifier is one or more of sodium dodecyl benzene sulfonate, sodium dodecyl diphenyl ether disulfonate and alkylphenol polyoxyethylene.
The pH buffering agent is sodium carbonate and/or ammonium bicarbonate.
The soft monomer is one or more of n-butyl acrylate, isooctyl acrylate, ethyl acrylate and lauryl methacrylate.
The hard monomer is one or more of methyl methacrylate, styrene, ethyl methacrylate, methyl acrylate, vinyl acetate and acrylonitrile.
The functional monomer is one or more of hydroxyethyl methacrylate, methacrylic acid, acrylic acid, hydroxyethyl acrylate and hydroxypropyl methacrylate.
The crosslinking monomer is one or more of adipyl hydrazide, diacetone acrylamide, acetoacetoxy ethyl methacrylate and acrylamide.
The initiator is azodiisobutyronitrile and/or potassium persulfate.
The structural formula of the modified silane coupling agent is shown in the specification
A method for preparing the modified silane coupling agent, comprising the steps of: phthalic anhydride reacts with a silane coupling agent under the action of acid catalysis.
The mass ratio of phthalic anhydride to silane coupling agent is 0.3-1.5:1.
in the method for preparing the modified silane coupling agent, the reaction temperature is 75-95 ℃, and the reaction time is 10-30min.
The silane coupling agent is preferably one or more of vinyltrimethoxysilane, vinyltriethoxysilane, vinyltrichlorosilane, vinyltri-tert-butoxysilane and vinyltriacetoxysilane.
As a preferred embodiment, the silane coupling agent is used in the form of an aqueous solution having a concentration of 0.5 to 2.5wt%.
In the method for preparing the modified silane coupling agent, the acid is one or more of sulfuric acid, nitric acid, hydrochloric acid and acetic acid; the addition amount of the acid is 0.5-1wt% of the total mass of the phthalic anhydride and the silane coupling agent.
A method for preparing the high-performance environment-friendly water-based acrylate laminating adhesive emulsion comprises the following steps: according to the mass portion of the components,
1) Adding an emulsifier, a pH buffering agent and deionized water into a reaction kettle, heating to 73-80 ℃, preferably 75-79 ℃, and starting stirring;
2) Uniformly mixing a soft monomer, a hard monomer, a functional monomer and a crosslinking monomer to obtain a mixed monomer;
3) Simultaneously dropwise adding the mixed monomer, part of the initiator aqueous solution and the modified silane coupling agent into the reaction kettle, and initiating polymerization under the stirring condition, wherein the polymerization reaction temperature is 80-85 ℃ and the reaction time is 1.5-2h;
4) The reaction temperature is not changed, and the rest initiator aqueous solution is dripped for 1.5 to 2 hours; keeping the temperature for 0.5-2h after the dropwise addition is finished;
5) And cooling to 20-40 ℃, then adjusting the pH of the emulsion to be neutral, filtering and discharging to obtain the water-based acrylate adhesive emulsion.
In the method for preparing the high-performance environment-friendly water-based acrylate laminating adhesive emulsion, the total consumption of the deionized water is 0.7-1.5 times of the dry weight of the water-based acrylate laminating adhesive emulsion.
As a preferable scheme, the dosage of the deionized water in the step 1) accounts for 35-55% of the total mass of the water.
In the method for preparing the high-performance environment-friendly water-based acrylate laminating adhesive emulsion, the initiator aqueous solution used in the step (3) accounts for 60-80% of the sum of the initiator aqueous solutions in the step (3) and the step (4).
As a preferred embodiment, the stirring speed in step 1) of the present invention is 150 to 350r/min, preferably 230 to 260r/min.
As a preferable scheme, the mixing and stirring time in the step 2) of the invention is 10-30min, and the mixing and stirring speed is 100-300r/min, preferably 150-180r/min.
As a preferred embodiment, the stirring speed in step 3) of the present invention is 200 to 300r/min, preferably 230 to 260r/min.
An environment-friendly water-based acrylate adhesive comprises the following components: the adhesive comprises water-based acrylate adhesive emulsion, a wetting agent, a defoaming agent and a thickening agent.
The wetting agent is a surfactant and consists of hydrophilic groups and lipophilic groups. When the hydrophilic group is contacted with the solid surface, the lipophilic group is attached to the solid surface, the hydrophilic group extends outwards to the liquid, so that the liquid forms a continuous phase on the solid surface, and the addition of the wetting agent can reduce the surface tension of a solution system and enable the solution system to be more easily spread on the solid surface. Suitable examples include, but are not limited to, one or more of basf WE3485, WE3475, BYK-345, BYK-346 added in an amount of 0.3% to 1% by mass of emulsion a.
The defoaming agent is a substance which can reduce the surface tension of a solution, prevent the formation of foam, or reduce or eliminate the original foam. Suitable examples include, but are not limited to, one or more of Solvay DF-691, BYK-024, BYK-025, tego-1488, added in an amount of 0.1% to 1% by mass of emulsion A.
The thickening agent is a substance capable of increasing the viscosity of an emulsion system. Suitable examples include, but are not limited to, one or more of ammonia, wanhua A801, wanhua A401, and Wanhua U604, with a post-thickening viscosity in the range of 8000-10000cps.
The phthalic anhydride modified silane coupling agent is grafted to synthesized macromolecules as a new raw material, and on one hand, the phthalic anhydride is used as a multi-ring structure, so that micromolecular particles such as acrylic ester and the like can be wrapped in the phthalic anhydride modified silane coupling agent, and the migration of water molecules in the water soaking process of a pressed product is effectively prevented. On the other hand, in the process of acrylic emulsion film formation, modified silane coupling agent molecules can perform coupling reaction with polar groups such as hydroxyl groups, carboxyl groups and the like in acrylic acid molecules to form covalent bond bonding force with higher strength, so that the compactness of the structure after macromolecular film formation is improved, and the water resistance of the product is improved after hot pressing, and the strength of the attached product is also improved.
The invention has the beneficial effects that: the adhesive is applied to surface bonding of non-woven fabrics, well-woven fabrics, ouchuo fabrics, PU foam, genuine leather or PU leather and the like. Has the characteristics of high bonding strength, good water resistance when soaking water, wide application range and convenient use.
Detailed Description
The present invention is further illustrated by the following specific examples, which are intended to be merely illustrative of the invention and not limiting of its scope.
In the examples, the sources of the raw materials are shown in the following table 1:
TABLE 1 raw materials and sources
The test method comprises the following steps:
1. dry peel strength: and (3) placing the attached sample at normal temperature for 30min, cutting the sample into 10cm multiplied by 25mm sample strips, testing 180-degree peeling force on a tensile machine at the speed of 30cm/min, testing data and observing the breakage condition of the surface material of the material.
2. Wet peel strength: and (3) placing the attached sample at normal temperature for 24h, cutting the sample into strips of 10cm multiplied by 25mm, placing the strips in normal temperature water at 25 ℃, soaking the strips in water for 24h, and then testing the stripping force at the speed of 180 degrees and 30cm/min by a tensile machine.
3. Viscosity: the viscosity was measured using a Brookfield, LV viscometer at 64#/30rpm at 25 ℃.
Modified silane coupling agent A
Weighing 1.5g of phthalic anhydride, adding the phthalic anhydride into 100g of silane coupling agent A151 aqueous solution (mass fraction is 1.0%), then adding 0.12g of dilute sulfuric acid (15%), reacting for 20min at the temperature of 92 ℃, and stirring at the speed of 200r/min; after the reaction is finished, filter residue is removed by a 325-mesh filter screen to obtain the modified silane coupling agent A for later use.
According to infrared test, at 1730-1740cm -1 The segment has a distinct absorption peak indicating the presence of an ester carbonyl.
Modified silane coupling agent B
Weighing 1.0g of phthalic anhydride, adding the phthalic anhydride into 100g of aqueous solution (mass fraction is 1.0%) of the silane coupling agent A171, then adding 0.12g of dilute sulfuric acid (15%), reacting for 20min at the temperature of 92 ℃, and stirring at the speed of 200r/min; after the reaction is finished, filter residue is removed by a 325-mesh filter screen to obtain the modified silane coupling agent B for later use.
According to the infrared test, at 1730-1740cm -1 The segment has a distinct absorption peak indicating the presence of an ester carbonyl.
Silane coupling agent C (comparative)
Weighing 100g of silane coupling agent A171 aqueous solution (mass fraction is 1.0%), then adding 0.12g of dilute sulfuric acid (15%), stirring at normal temperature for 20min, and stirring at the speed of 200r/min; and then filter residue is removed by a filter screen with 325 meshes to obtain the silane coupling agent C for later use.
Example 1
1) Adding 5g of OP-10, 4g of SDBS, 5g of ammonium bicarbonate and 200g of deionized water into a reaction kettle, heating to 78 ℃, starting stirring, and heating for 8min; the stirring speed is 240r/min;
2) Uniformly mixing 90g of 2-EHA, 110g of BA, 50g of MMA, 200g of St, 10g of AA and 3.8g of AAEM to obtain a mixed monomer; the mixing and stirring time of the monomers is 30min, and the mixing and stirring speed is 240r/min;
3) Uniformly mixing 12g of KSP and 200g of deionized water to obtain 212g of initiator solution;
4) Simultaneously dropwise adding mixed monomers, 75% of initiator solution and 0.7g of modified silane coupling agent into the reaction kettle, and initiating polymerization under the condition of stirring, wherein the polymerization temperature is 85 ℃ and the reaction time is 1.5 hours; the stirring speed is 250r/min;
5) Dropwise adding the rest initiator solution for 1.5h, and then preserving heat for 1h;
6) And (3) cooling to 35 ℃, adjusting the pH of the emulsion to be =7 by using a 10wt% sodium hydroxide solution, filtering by using a 100-mesh filter screen, and discharging to obtain the water-based acrylate emulsion A.
7) Adding WE3485 wetting agent 0.3 wt%, DF691 defoaming agent 0.5 wt% and 10% ammonia water into the acrylic ester emulsion A, stirring to adjust viscosity to 8000-10000cps to obtain high performance environment friendly acrylic ester adhesive 1.
Examples 2 to 10
Aqueous acrylate emulsions were prepared according to the method of example 1 and the raw material selection and amount (g) of Table 2, respectively.
Table 2 examples raw material amounts
Comparative example 1
The aqueous acrylic emulsion was prepared using the selection and amounts of the raw materials in example 2, with the only differences being: step 4, no modified silane coupling agent is added.
Comparative example 2
The aqueous acrylic emulsion was prepared using the selection of the type and amount of the raw materials in example 4, with the only differences being: step 4, no modified silane coupling agent is added.
Comparative example 3
The aqueous acrylic emulsion was prepared using the type and amount of the raw materials in example 9, except that: step 4, an equal amount of silane coupling agent C was added.
The high-performance environment-friendly acrylate laminating adhesives prepared in the examples 1-10 and the comparative examples 1-3 are respectively coated on the surface of a PU foam surface, and the coating weight is 45g/m 2 And hot pressing 2 at 140 deg.C and 0.1MPa after bonding with non-woven fabricAnd 5s, cooling and preparing a sample for testing the laminating adhesive.
The pressure sensitive adhesive samples prepared by the emulsions of the examples were subjected to the performance tests in table 3, with the results shown below:
table 3 results of performance testing
Note: are all Shore D hardness
From the above test results it can be seen that: (1) Compared with comparative examples 1 and 2, dry peeling and wet peeling effects are superior to those of examples 1 to 10 to which the modified silane coupling agent is added. (2) Under the same embodiment, the different hardness of the Euler cable is different in tensile test, the 28 hardness is better than the 35 hardness, the attaching effect is good, and the stripping force and the material breaking effect are better. (3) It can be seen that the tensile force and material breaking effect of the modified silane coupling agent added in an amount of 0.3% are inferior to those of the other high-dosage formulations in examples 3 and 10 compared with other examples. (4) Comparison of comparative example 3 with example 9 shows that the material breaking effect is much better when the modified silane coupling agent is added than when the same amount of the conventional silane coupling agent is added.
It should be noted that the above-mentioned embodiments illustrate only preferred embodiments of the present invention, and are not intended to limit the scope of the present invention, and although the present invention has been described in detail with reference to preferred embodiments, it will be understood by those skilled in the art that various changes and modifications can be made to the technical solutions of the present invention or equivalents thereof without departing from the scope of the present invention as defined in the claims.
Claims (12)
1. A silane coupling agent with the structural formula
2. A method for preparing the silane coupling agent of claim 1, comprising the steps of: phthalic anhydride reacts with a silane coupling agent under the action of acid catalysis; the silane coupling agent is selected from one or more of vinyltrimethoxysilane, vinyltriethoxysilane, vinyltrichlorosilane, vinyltri-tert-butoxysilane and vinyltriacetoxysilane.
3. The method according to claim 2, wherein the mass ratio of phthalic anhydride to silane coupling agent is 0.3 to 1.5:1; and/or the reaction temperature is 75-95 ℃, and the reaction time is 10-30min; and/or the acid is one or more of sulfuric acid, nitric acid, hydrochloric acid and acetic acid; the addition amount of the acid is 0.5-1wt% of the total mass of the phthalic anhydride and the silane coupling agent.
4. The water-based acrylate laminating adhesive emulsion is prepared from the following raw materials in parts by mass:
5. the water-based acrylate laminating adhesive emulsion according to claim 4, which is prepared from the following raw materials in parts by mass:
6. the water-based acrylate laminating adhesive emulsion of claim 4, wherein the soft monomer is one or more of n-butyl acrylate, isooctyl acrylate, ethyl acrylate and lauryl methacrylate; and/or the hard monomer is one or more of methyl methacrylate, styrene, ethyl methacrylate, methyl acrylate, vinyl acetate and acrylonitrile; and/or the functional monomer is one or more of hydroxyethyl methacrylate, methacrylic acid, acrylic acid, hydroxyethyl acrylate and hydroxypropyl methacrylate; and/or the crosslinking monomer is one or more of adipamide, diacetone acrylamide, acetoacetoxy ethyl methacrylate and acrylamide.
7. A method of making the aqueous acrylate laminating adhesive emulsion of claim 4, comprising the steps of: according to the mass portion of the components,
1) Adding an emulsifier, a pH buffering agent and deionized water into a reaction kettle, heating to 73-80 ℃, and starting stirring;
2) Uniformly mixing a soft monomer, a hard monomer, a functional monomer and a crosslinking monomer to obtain a mixed monomer;
3) Simultaneously dropwise adding the mixed monomer, part of the initiator aqueous solution and the modified silane coupling agent into the reaction kettle, and initiating polymerization under the stirring condition, wherein the polymerization reaction temperature is 80-85 ℃ and the reaction time is 1.5-2h;
4) The reaction temperature is not changed, and the rest initiator aqueous solution is dripped for 1.5 to 2 hours; preserving the heat for 0.5-2h after the dropwise adding is finished;
5) And cooling to 20-40 ℃, then adjusting the pH of the emulsion to be neutral, filtering and discharging to obtain the water-based acrylate adhesive emulsion.
8. The method according to claim 7, wherein the heating temperature in step 1) is 75-79 ℃.
9. An aqueous acrylate laminating adhesive comprises the following components: the aqueous acrylate laminating adhesive emulsion of claim 4, a wetting agent, a defoamer, and a thickener.
10. The water-based acrylate laminating adhesive according to claim 9, wherein the wetting agent is selected from one or more of basf WE3485, WE3475, BYK-345 and BYK-346, and the addition amount is 0.3-1% of the mass of the water-based acrylate laminating adhesive emulsion a.
11. The water-based acrylate adhesive according to claim 9, wherein the defoamer is selected from one or more of solvay DF-691, BYK-024, BYK-025 and Tego-1488, and is added in an amount of 0.1-1% by mass of emulsion A.
12. The water-based acrylate adhesive according to claim 9, wherein the thickener is one or more selected from ammonia, wanhua A801, wanhua A401 and Wanhua U604, and the viscosity after thickening is 8000-10000cps.
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