CN108484803B - Silane-terminated polymer and moisture-cured adhesive composition prepared from same - Google Patents
Silane-terminated polymer and moisture-cured adhesive composition prepared from same Download PDFInfo
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- CN108484803B CN108484803B CN201810257893.6A CN201810257893A CN108484803B CN 108484803 B CN108484803 B CN 108484803B CN 201810257893 A CN201810257893 A CN 201810257893A CN 108484803 B CN108484803 B CN 108484803B
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- C—CHEMISTRY; METALLURGY
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing groups
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J147/00—Adhesives 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; Adhesives based on derivatives of such polymers
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
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Abstract
The invention relates to the field of polyolefin polymers, in particular to a silane terminated polymer and a moisture curing adhesive composition prepared from the silane terminated polymer. The invention provides a silane terminated polymer, which comprises the following components in percentage by weight: 70-95% of hydroxyl-terminated polybutadiene, 4.98-29.5% of silane containing reactive functional group, 0.01-0.5% of catalyst A; the silane containing a reactive functional group is a silane that can react with a hydroxyl group. And the silane-terminated polymer prepared by the invention is used for preparing the moisture curing daub composition together with the catalyst B, the cross-linking agent, the filler and the plasticizer. The moisture curing daub composition prepared by the invention has excellent waterproof performance, lower water vapor transmittance, no solvent volatilization and excellent temperature resistance.
Description
Technical Field
The invention relates to the field of polyolefin polymers, in particular to a silane terminated polymer and a moisture curing adhesive composition prepared from the silane terminated polymer.
Background
Moisture-curing adhesives are typically prepared from a silicone hydroxyl-terminated polysiloxane, silane-terminated polyether or polyester polymer, with appropriate fillers and catalysts and crosslinkers.
For waterproof applications, both the hydroxyl-terminated polysiloxanes and the silane-terminated polyesters and polyethers have generally high water vapor transmission rates but poor water resistance due to the nature of their own molecular structure.
Disclosure of Invention
In order to overcome the defects of the prior art, the silane-terminated polymer and the moisture-cured adhesive composition prepared on the basis of the silane-terminated polymer are prepared to reduce the water vapor permeability and improve the hydrolysis resistance, and the moisture-cured adhesive composition can be cured at room temperature, has excellent waterproof performance and lower water vapor permeability and provides a brand new scheme for waterproof application. The invention provides a silane terminated polymer and a moisture curing adhesive composition prepared from the same.
The invention provides a silane terminated polymer, which comprises the following components in percentage by weight: 70-95% of hydroxyl-terminated polybutadiene, 4.98-29.5% of silane containing reactive functional group, 0.01-0.5% of catalyst A; the silane containing a reactive functional group is a silane that can react with a hydroxyl group. When the content of the hydroxyl-terminated polybutadiene is 4.75-95%, the moisture-curing cement composition has excellent mechanical properties, waterproof properties and temperature resistance. If the content of the hydroxyl-terminated polybutadiene is less than 70%, adverse effects of poor temperature resistance may be caused; if the hydroxyl-terminated polybutadiene content is more than 95%, the adverse effects of low crosslinking degree and weak strength may be caused.
Silane-terminated polymers can be prepared by two methods:
1. hydroxyl-terminated polybutadiene reacts with isocyanate silane to prepare a silane-terminated polymer;
2. the epoxy silane is reacted with hydroxyl terminated polybutadiene to produce a silane terminated polymer.
In the above scheme, the molecular weight of the hydroxyl-terminated polybutadiene is 1000-3000, the functionality is 2-2.6, and the hydroxyl-terminated polybutadiene may be one or more selected from the following groups available from japan caoda: g1000, G2000, G3000; g2000 and G3000 are preferred, and G2000 is particularly preferred.
In the scheme, the silane containing the reactive functional group is one or more of isocyanate silane and epoxy silane.
In the scheme, the catalyst A is one or more of dibutyltin diacetate, dibutyl tin and stannous octoate.
The invention also provides a moisture-curing adhesive composition, which comprises the following components in percentage by weight: 20-60% of a silane-terminated polymer as claimed in any of claims 1 to 3, 0.01-2% of catalyst B, 1-5% of a crosslinking agent, 28.99-68.99% of a filler, 10-50% of a plasticizer.
The silane-terminated polymer is present in an amount of 20 to 60 weight percent, preferably 20 to 55 weight percent, based on 100 weight percent of the total moisture-curing composition. When the content of the silane-terminated polymer is 20-60%, the adhesive composition has excellent mechanical properties, heat resistance and water resistance. If the content of the silane-terminated polymer is less than 20%, poor waterproofing may result; if the content of the silane-terminated polymer is more than 60%, it may result in poor adhesive strength.
The content of the cross-linking agent is 1-5% by the total weight of the moisture-curable adhesive composition based on 100%. When the content of the crosslinking agent is 1 to 5%, the moisture-curable adhesive composition has excellent mechanical properties and water resistance. If the content of the crosslinking agent is less than 1%, there is a possibility that an adverse effect of incomplete curing may be caused; if the content of the crosslinking agent is more than 5%, an adverse effect of excessive crosslinking may be caused.
The total weight of the moisture-cured adhesive composition is 100%, and when the content of the filler is 28.99-68.99%, the moisture-cured adhesive composition has moderate hardness before curing and excellent mechanical property and waterproof property after curing. If the content of the filler is more than 68.99%, the adhesive may be hard before curing and have an adverse effect of poor waterproof performance after curing.
The plasticizer is present in an amount of 10 to 50% based on 100% by weight of the total moisture-curable adhesive composition. When the content of the plasticizer is 10-50%, the cured product has better comprehensive performance. If the content of the plasticizer is more than 50%, there is a possibility that the plasticizer is precipitated.
In the scheme, the catalyst B is one or more of dibutyltin diacetate, dibutyl tin and stannous octoate. Preferably, the weight percentage content of the catalyst B is 0.05-1.1%.
In the scheme, the cross-linking agent is one or more of gamma-mercaptopropyltriethoxysilane, gamma-mercaptopropyltrimethoxysilane, methyltriethoxysilane, tetramethoxysilane, tetrapropoxysilane, tetraethoxysilane and triacetoxyethylsilane, methyltriacetoxysilane, methyltrimethoxysilane, tris (isopropenyloxy) vinylsilane, methyltributanonoximesilane, vinyltrimethoxysilane and 3- (2, 3-epoxypropoxy) propyltrimethoxysilane. Preferably, gamma-mercaptopropyltrimethoxysilane, methyltriethoxysilane, tetramethoxysilane, tetrapropoxysilane, tetraethoxysilane and triacetoxyethylsilane, methyltriacetoxysilane, methyltrimethoxysilane, tris (isopropenylpropoxy) vinylsilane, methyltributanonoximosilane, vinyltrimethoxysilane; particularly preferred are methyltriethoxysilane, tetramethoxysilane, tetrapropoxysilane, and vinyltrimethoxysilane. The crosslinker may be selected from the methyltriacetoxysilane product available from Dow Corning, USA. Preferably, the weight percentage of the cross-linking agent is 2-4%.
In the scheme, the filler is calcium carbonate, kaolin, molecular sieve, powdered talcum powder, wollastonite, titanium dioxide, barite powder, carbon black, montmorillonite, silicon dioxide and Al2O3One or more of glass fiber and graphite. Preferably, the weight percentage of the filler is 30.5-63.95%.
In the scheme, the plasticizer is one or more of paraffin oil, naphthenic oil, simethicone, dioctyl terephthalate and dibutyl terephthalate. Preferably, the weight percentage of the plasticizer is 10-20%.
The silane-terminated polymer and the moisture-curing daub composition prepared from the silane-terminated polymer have the following beneficial effects:
the moisture curing daub composition prepared by the invention has excellent waterproof performance, lower water vapor transmittance, no solvent volatilization and excellent temperature resistance.
Detailed Description
The invention will now be further illustrated by reference to the following examples:
examples 1-9 preparation of silane terminated polymers
Examples 1-8 were prepared according to method 1: hydroxyl-terminated polybutadiene and isocyanate-containing silane are added into a reaction kettle according to the weight percentage shown in table 2, a proper amount of catalyst is added after uniform stirring, and silane-terminated polymer is obtained after 4 hours of reaction and discharging, wherein the raw material components and manufacturers refer to table 1.
Example 9 was prepared according to method 2: hydroxyl-terminated polybutadiene and epoxy-containing polybutadiene were mixed in the weight percentages shown in Table 2Adding silane of the group into a reaction kettle, uniformly stirring, and adding a proper amount of catalyst BF3The reaction was discharged after 4 hours to give the silane-terminated polymer, the raw material composition and the manufacturer being referred to in Table 1.
The method comprises the following steps: hydroxyl-terminated polybutadiene and isocyanate-containing silane are added into a reaction kettle according to the weight percentage shown in table 2, a proper amount of catalyst is added after uniform stirring, and silane-terminated polymer is obtained after 4 hours of reaction and discharging, wherein the raw material components and manufacturers refer to table 1.
The method 2 comprises the following steps: according to the weight percentage shown in table 2, hydroxyl-terminated polybutadiene and silane containing epoxy groups are added into a reaction kettle, and after being uniformly stirred, a proper amount of catalyst BF is added3The reaction was discharged after 4 hours to give the silane-terminated polymer, the raw material composition and the manufacturer being referred to in Table 1.
Table 1 raw material ingredients used in the examples and manufacturers
TABLE 2 Components and component ratios of silane terminated polymers
Examples 10-18, examples 19-25, comparative examples 1-5, comparative examples 6-8:preparation of moisture-curing adhesive composition
Examples 10-18 were prepared using the silane-terminated polymers prepared in examples 1-9 as starting materials, respectively, in the proportions shown in Table 3.
Examples 19-25 were prepared according to the formulation ratios listed in Table 3, starting from the silane-terminated polymer prepared in example 6.
The preparation method comprises the following steps: sequentially adding the silane-terminated polymer, the filler and the plasticizer into a stirring kettle, uniformly mixing, adding the cross-linking agent and the filler, continuously stirring and mixing for ten minutes, and discharging to obtain the moisture-cured daub composition. The moisture-curable adhesive composition was prepared into a sheet having a thickness of 1mm by a press, and after curing at 25 ℃ and 60% humidity for 7 days, the surface dry property, mechanical properties and water resistance of the moisture-curable mastic composition were measured according to the following test methods, and the test results are shown in Table 4.
Comparative examples 1-5 were prepared according to the formulation ratios listed in Table 3 using the silane-terminated polymers prepared in example 6 as starting materials.
The preparation method comprises the following steps: sequentially adding the silane-terminated polymer, the filler and the plasticizer into a stirring kettle, uniformly mixing, adding the cross-linking agent and the filler, continuously stirring and mixing for ten minutes, and discharging to obtain the moisture-cured daub composition. The moisture-curable adhesive composition was prepared into a sheet having a thickness of 1mm by a press, and after curing at 25 ℃ and 60% humidity for 7 days, the surface dry property, mechanical properties and water resistance of the moisture-curable mastic composition were measured according to the following test methods, and the test results are shown in Table 4.
The preparation method of comparative examples 6 to 8 was: hydroxyl-terminated polydimethylsiloxane (viscosity 5000cps), a Japanese Brillouin chemical silane-terminated polymer S202H and a Japanese Brillouin chemical silane-terminated polymer S303H, which are available from Lanxing-Star fire organosilicon Co., Ltd, were used as raw materials, respectively, and were prepared in the formulation ratios listed in Table 3.
The preparation method comprises the following steps: sequentially adding the silane-terminated polymer, the filler and the plasticizer into a stirring kettle, uniformly mixing, adding the cross-linking agent and the filler, continuously stirring and mixing for ten minutes, and discharging to obtain the moisture-cured daub composition. The moisture-curable adhesive composition was prepared into a sheet having a thickness of 1mm by a press, and after curing at 25 ℃ and 60% humidity for 7 days, the surface dry property, mechanical properties and water resistance of the moisture-curable mastic composition were measured according to the following test methods, and the test results are shown in Table 4.
Test methods for moisture-curing mastic compositions:
testing the surface dry time according to the fifth part of GB/T13477.5-2002;
testing the tensile strength according to the Chinese national standard GB/T528-;
the tearing strength is tested according to the Chinese national standard GB/T528-;
wrapping related products by using the prepared adhesive, and testing the waterproof performance according to the waterproof grade of the IP series;
testing the water vapor transmission rate according to GB/T1037-;
TABLE 3 Components and component ratios of moisture-curing mastic compositions
Table 4 performance test results for moisture-curing cement compositions
As shown in table 4: when the content of the silane-terminated polymer is 20-60%, the content of the catalyst is 0.01-2%, the content of the cross-linking agent is 1-5%, the content of the filler is 28.99-68.99%, and the content of the plasticizer is 10-50%, the moisture-cured adhesive composition has good operable time (surface dry time), tensile strength, tear strength and waterproof performance.
As shown in comparative example 1, when the content of the catalyst is less than 0.01%, the moisture-curable adhesive cures too slowly, i.e., the open time is too long; when the content of the catalyst is more than 2%, as shown in comparative example 4, the curing is too fast, i.e., the open time is too short, i.e., the working time is too short. As shown in comparative examples 1 and 3, when the content of the silane-terminated polyolefin is less than 20% or the content of the filler is more than 68.99%, the moisture-curable mastic has too high hardness, resulting in poor waterproofing performance;as shown in comparative example 2, when the content of the silane-terminated polyolefin was more than 60% or the content of the filler was less than 28.99%, the adhesive was too sticky to handle and could not be tested for water-proof properties. As shown in comparative example 5, when the content of the plasticizer is more than 50%, the plasticizer may be separated out and the strength of the cured adhesive is weak. As shown in comparative example 2, more crosslinking agent can cause the precipitation of low molecular weight substances after the glue is cured; as shown in comparative example 1, when the content of the crosslinking agent is too low, the strength of the cured gel is affected, so that the tensile strength and the tear strength are low. As can be seen from Table 4, the moisture-curable adhesive prepared from the silane-terminated polyolefin polymer has a water vapor transmission rate of about 10 to 13 g/(m)224h), much less than 22-25 g/(m) of moisture-curing adhesive prepared from hydroxyl-terminated polysiloxane and silane-terminated polyether224h), as shown in comparative examples 6 to 8.
Claims (8)
1. A moisture-curable adhesive composition comprising the following components in weight percent: 20-60% of silane terminated polymer, 0.01-2% of catalyst B, 1-5% of cross-linking agent, 28.99-68.99% of filler and 10-50% of plasticizer; the catalyst B is one or more of dibutyltin diacetate, dibutyltin and stannous octoate;
the silane-terminated polymer comprises the following components in weight percent: 70-95% of hydroxyl-terminated polybutadiene, 4.98-29.5% of silane containing reactive functional group, 0.01-0.5% of catalyst A; the silane containing the reactive functional group is a silane capable of reacting with a hydroxyl group; the catalyst A is one or more of dibutyltin diacetate, dibutyltin and stannous octoate.
2. The moisture-curable adhesive composition according to claim 1, wherein the hydroxyl-terminated polybutadiene has a molecular weight of 1000-3000 and a functionality of 2-2.6.
3. The moisture-curable adhesive composition according to claim 1, wherein the silane containing a reactive functional group is one or more of isocyanate silane and epoxy silane.
4. The moisture-curable adhesive composition of claim 1 wherein said silane-terminated polymer is present in an amount of from 20 to 55 weight percent.
5. The moisture-curable adhesive composition according to claim 1, wherein the catalyst B is present in an amount of 0.05 to 1.1% by weight.
6. A moisture curable adhesive composition according to claim 1, wherein said cross-linking agent is one or more of gamma-mercaptopropyltriethoxysilane, gamma-mercaptopropyltrimethoxysilane, methyltriethoxysilane, tetramethoxysilane, tetrapropoxysilane, tetraethoxysilane and triacetoxyethylsilane, methyltriacetoxysilane, methyltrimethoxysilane, tris (isopropenyloxy) vinylsilane, methyltributanonoximosilane, vinyltrimethoxysilane, 3- (2, 3-glycidoxy) propyltrimethoxysilane; the weight percentage of the cross-linking agent is 2-4%.
7. The moisture-curable adhesive composition of claim 1, wherein the filler is calcium carbonate, kaolin, molecular sieve, powdered talc, wollastonite, titanium dioxide, barite powder, carbon black, montmorillonite, silica, Al2O3One or more of glass fiber and graphite, wherein the weight percentage of the filler is 30.5-63.95%.
8. The moisture-curable adhesive composition according to claim 1, wherein the plasticizer is one or more selected from paraffin oil, naphthenic oil, simethicone, dioctyl terephthalate and dibutyl terephthalate, and the weight percentage of the plasticizer is 10-20%.
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| CN111154445B (en) * | 2020-01-17 | 2021-03-19 | 杭州之江新材料有限公司 | Two-component waterproof sealant |
| CN112358833A (en) * | 2020-11-09 | 2021-02-12 | 吴文静 | Reactive hot melt adhesive raw material and preparation method thereof |
| CN112680175B (en) * | 2020-12-14 | 2024-01-16 | 深圳斯多福新材料科技有限公司 | But dual curing silica gel of UV moisture |
| CN114410214B (en) * | 2022-01-25 | 2022-11-29 | 宏源防水科技集团有限公司 | High-water-resistance polyurethane waterproof coating and preparation method thereof |
| CN114670294B (en) * | 2022-03-31 | 2022-12-06 | 安徽省科晟生态木装饰材料有限公司 | High-strength ecological plate and manufacturing process |
| CN115772366A (en) * | 2022-12-08 | 2023-03-10 | 东莞市新合硅胶材料科技有限公司 | Coating for coating PU and silica gel leather surfaces and preparation method thereof |
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