CN108484803A - A kind of silane-terminated polymer and moisture-curable adhesive compound prepared therefrom - Google Patents
A kind of silane-terminated polymer and moisture-curable adhesive compound prepared therefrom Download PDFInfo
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- CN108484803A CN108484803A CN201810257893.6A CN201810257893A CN108484803A CN 108484803 A CN108484803 A CN 108484803A CN 201810257893 A CN201810257893 A CN 201810257893A CN 108484803 A CN108484803 A CN 108484803A
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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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- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
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Abstract
The present invention relates to polyolefin polymer field, in particular to a kind of silane-terminated polymer and moisture-curable adhesive compounds prepared therefrom.The present invention provides a kind of silane-terminated polymer, includes the component of following percent by weight：70 95% end hydroxy butadiene, 4.98 29.5% silane containing reactive functional groups, 0.01 0.5% catalyst A；The silane containing reactive functional groups is can be with the silane of hydroxyl reaction.The silane-terminated polymer for being used in combination the present invention to prepare, moisture-curable cement compositions are prepared with catalyst B, crosslinking agent, filler and plasticizer.The moisture-curable cement compositions that the present invention is prepared, with excellent water resistance and lower water vapor transmittance, solvent-free volatilization, heat resistance is excellent.
Description
Technical field
The present invention relates to polyolefin polymer field, in particular to a kind of silane-terminated polymers and moisture prepared therefrom
Cured adhesive composition.
Background technology
Moisture-curable adhesive is usually by the polysiloxanes of silicone hydroxyl sealing end, Silante terminated polyethers or polyester
Object is equipped with filler and catalyst and crosslinking agent appropriate and is prepared.
For waterproof applications, the polysiloxanes or Silante terminated polyester and polyethers no matter silicone hydroxyl blocks, due to
The characteristic of itself molecular structure, water vapor transmittance is usually higher, and water resistance is poor.
Invention content
To overcome the problems of the above-mentioned prior art, to reduce water vapor transmittance, improve anti-hydrolytic performance, system of the present invention
A kind of standby silane-terminated polymer, and the moisture-curable adhesive compound that is prepared based on the polymer, this moisture
Cured adhesive composition can cure at ambient temperature, have excellent water resistance and lower water vapor transmittance, be
Waterproof applications provide completely new scheme.The present invention provides a kind of silane-terminated polymer and moisture-curable adhesive prepared therefrom
Composition.
The present invention provides a kind of silane-terminated polymer, includes the component of following percent by weight：The end hydroxyl of 70-95%
Base polybutadiene, the silane containing reactive functional groups of 4.98-29.5%, the catalyst A of 0.01-0.5%；It is described to contain reactivity
The silane of functional group is can be with the silane of hydroxyl reaction.It is described when the content of the end hydroxy butadiene is 4.75-95%
Moisture-curable cement compositions have excellent mechanical performance, water resistance and heat resistance.If end hydroxy butadiene contains
Amount is less than 70%, may result in the bad unfavorable effect of heat resistance；If the content of end hydroxy butadiene is more than 95%, can
It can cause the unfavorable effect that the degree of cross linking is relatively low, intensity is weaker.
Silane-terminated polymer can be prepared by following two methods：
1. end hydroxy butadiene is reacted with isocynate silane prepares silane-terminated polymer；
2. epoxy silane is reacted with end hydroxy butadiene prepares silane-terminated polymer.
In the above scheme, the molecular weight of end hydroxy butadiene is 1000-3000, and degree of functionality is 2~2.6, terminal hydroxy group
Polybutadiene can be selected purchased from one or more in following group of Cao Da companies of Japan：G1000, G2000, G3000；It is preferred that
G2000, G3000, particularly preferred G2000.
In the above scheme, the silane containing reactive functional groups is one kind in isocynate silane, epoxy silane
Or it is several.
In the above scheme, the catalyst A is one kind in dibutyltin diacetate, dibutyltin dilaurate and stannous octoate
Or it is several.
The present invention also provides a kind of moisture-curable adhesive compounds, include the component of following percent by weight：20-
Any one of the 60% claim 1-3 silane-terminated polymers, the crosslinking agent of the catalyst B, 1-5% of 0.01-2%,
The filler of 28.99-68.99%, the plasticizer of 10-50%.
The gross weight of moisture cured composition is based on 100%, and the content of the silane-terminated polymer is 20-60%, preferably
, the weight percentage of the silane-terminated polymer is 20-55%.When the content of the silane-terminated polymer is 20-
When 60%, the adhesive compound has excellent mechanical performance, heat resistance and water resistance.If silane-terminated polymer
Content be less than 20%, it is bad to may result in waterproof effect；If the content of silane-terminated polymer is more than 60%, may lead
Cause adhesive intensity weaker.
For the gross weight of moisture-curable adhesive compound based on 100%, the content of crosslinking agent is 1-5%.When containing for crosslinking agent
When amount is 1-5%, moisture-curable adhesive compound has excellent mechanical performance and water resistance.If the content of crosslinking agent is small
In 1%, the incomplete unfavorable effect of solidification may result in；If the content of crosslinking agent is more than 5%, excessive crosslinking may result in
Unfavorable effect.
The gross weight of moisture-curable adhesive compound is wet when the content of filler is 28.99-68.99% based on 100%
Have neither too hard, nor too soft before the solidification of curing adhesive compound, there is excellent mechanical performance and water resistance after solidification.If filling out
The content of material is more than 68.99%, may result in harder, the bad unfavorable effect of water resistance after solidification before adhesive solidification.
By the gross weight of moisture-curable adhesive compound based on 100%, the content of plasticizer is 10-50%.Work as plasticizer
Content be 10-50% when, solidfied material have preferable comprehensive performance.If the content of plasticizer is more than 50%, may will produce
The problem of plasticizer.
In the above scheme, the catalyst B is one kind in dibutyltin diacetate, dibutyltin dilaurate and stannous octoate
Or it is several.Preferably, the weight percentage of the catalyst B is 0.05%-1.1%.
In the above scheme, the crosslinking agent be gamma-mercaptopropyltriethoxysilane, γ-mercaptopropyl trimethoxysilane,
Methyltriethoxysilane, tetramethoxy-silicane, tetrapropoxysilane, tetraethoxysilane and triacetoxyl group ethylsilane,
Methyl triacetoxysilane, methyltrimethoxysilane, three (isoolefine propoxyl group) vinyl silanes, methyl tributanoximo silicon
One or more of alkane, vinyltrimethoxysilane, 3- (the third oxygen of 2,3- epoxies) propyl trimethoxy silicane.Preferably
For γ-mercaptopropyl trimethoxysilane, methyltriethoxysilane, tetramethoxy-silicane, tetrapropoxysilane, tetraethoxy
Silane and triacetoxyl group ethylsilane, methyl triacetoxysilane, methyltrimethoxysilane, three (isoolefine propoxyl group) second
Alkenyl silanes, methyl tributanoximo silane, vinyltrimethoxysilane；Particularly preferred methyltriethoxysilane, tetramethyl
Oxysilane, tetrapropoxysilane, vinyltrimethoxysilane.Crosslinking agent can select the first purchased from Dow corning company
Base triacetoxysilane product.Preferably, the weight percentage of the crosslinking agent is 2-4%.
In the above scheme, the filler be calcium carbonate, kaolin, molecular sieve, powder talcum powder, wollastonite, titanium dioxide,
Blanc fixe, carbon black, montmorillonite, silica, Al2O3, it is glass fibre, one or more of in graphite.Preferably, the filler
Weight percentage is 30.5-63.95%.
In the above scheme, the plasticizer be paraffin oil, it is naphthenic oil, dimethicone, dioctyl terephthalate, right
One or more of dibatyl phithalate.Preferably, the weight percentage of the plasticizer is 10-20%.
Implement silane-terminated polymer of the present invention and moisture-curable cement compositions prepared therefrom, has following
Advantageous effect：
There is the moisture-curable cement compositions that the present invention is prepared excellent water resistance and lower steam to penetrate
Rate, solvent-free volatilization, heat resistance are excellent.
Specific implementation mode
With reference to embodiment, the invention will be further described：
Embodiment 1-9 prepares silane-terminated polymer
Embodiment 1-8 is prepared according to method 1：According to weight percent shown in table 2 by end hydroxy butadiene and containing different
Ylisocyanate silane is added in reaction kettle, is stirring evenly and then adding into suitable catalyst, and discharging after reacting 4 hours, it is Silante terminated to obtain
Polymer, wherein composition of raw material and manufacturer are referring to table 1.
Embodiment 9 is prepared according to method 2：By end hydroxy butadiene and contain epoxy according to weight percent shown in table 2
The silane of group is added in reaction kettle, is stirring evenly and then adding into suitable catalyst BF3, discharge after reacting 4 hours and obtain silane
Terminated polymer, wherein composition of raw material and manufacturer are referring to table 1.
Method 1：Reaction is added by end hydroxy butadiene and containing isocynate silane according to weight percent shown in table 2
In kettle, it is stirring evenly and then adding into suitable catalyst, reaction discharges after 4 hours and obtains silane-terminated polymer, wherein raw material
Ingredient and manufacturer are referring to table 1.
Method 2：End hydroxy butadiene and silane containing epoxy group be added according to weight percent shown in table 2 anti-
It answers in kettle, is stirring evenly and then adding into suitable catalyst BF3, discharge after reacting 4 hours and obtain silane-terminated polymer, wherein
Composition of raw material and manufacturer are referring to table 1.
Raw materials used ingredient and manufacturer in 1 embodiment of table
The component and component ratio of 2 silane-terminated polymer of table
Embodiment 10-18, embodiment 19-25, comparative example 1-5, comparative example 6-8：Prepare moisture-curable adhesive compound
It is respectively raw material that the preparation method of embodiment 10-18, which is by the embodiment 1-9 silane-terminated polymers prepared, according to
Listed by table 3 prepared by formula rate.
The preparation method of embodiment 19-25 is the silane-terminated polymer that is prepared using embodiment 6 as raw material, according to 3 institute of table
It is prepared by row formula rate.
Preparation method is：Successively by silane-terminated polymer, filler, plasticizer is added in stirred tank, after mixing,
Crosslinking agent and filler is added, continues to be stirred ten minutes, discharge to obtain moisture-curable cement compositions.By moisture-curable adhesive
Composition is prepared into the sheet material of 1mm thickness with press, after curing 7 days under 25 DEG C, 60% damp condition, according to following test method
Surface drying performance, mechanical performance and the water resistance of moisture-curable cement compositions are tested, test result is listed in table 4.
The preparation method of comparative example 1-5 is that the silane-terminated polymer prepared with embodiment 6 is respectively raw material, according to table 3
It is prepared by listed formula rate.
Preparation method is：Successively by silane-terminated polymer, filler, plasticizer is added in stirred tank, after mixing,
Crosslinking agent and filler is added, continues to be stirred ten minutes, discharge to obtain moisture-curable cement compositions.By moisture-curable adhesive
Composition is prepared into the sheet material of 1mm thickness with press, after curing 7 days under 25 DEG C, 60% damp condition, according to following test method
Surface drying performance, mechanical performance and the water resistance of moisture-curable cement compositions are tested, test result is listed in table 4.
The preparation method of comparative example 6-8 is：Respectively with the hydroxy-end capped poly dimethyl of blue star spark organosilicon Co., Ltd
Siloxanes (viscosity 5000cps), Japanese clock deep pool chemistry silane-terminated polymer S202H and the Silante terminated polymerization of Japanese clock deep pool chemistry
Object S303H is raw material, is prepared according to formula rate listed by table 3.
Preparation method is：Successively by silane-terminated polymer, filler, plasticizer is added in stirred tank, after mixing,
Crosslinking agent and filler is added, continues to be stirred ten minutes, discharge to obtain moisture-curable cement compositions.By moisture-curable adhesive
Composition is prepared into the sheet material of 1mm thickness with press, after curing 7 days under 25 DEG C, 60% damp condition, according to following test method
Surface drying performance, mechanical performance and the water resistance of moisture-curable cement compositions are tested, test result is listed in table 4.
The test method of moisture-curable cement compositions：
Surface drying time is tested according to GB/T 13477.5-2002 Part V；
Tensile strength is tested according to chinese national standard GB/T 528-1998；
Tearing strength is tested according to chinese national standard GB/T 528-1998；
Correlated product is wrapped up with prepared adhesive, according to IP series waterproofing grade testing water-proof performances；
Water vapor transmittance is tested according to GB/T 1037-1988, test sample thickness is 1mm；
The component and component ratio of 3 moisture-curable cement compositions of table
The performance test results of 4 moisture-curable cement compositions of table
As shown in table 4：The content of silane-terminated polymer is 20-60%, catalyst content 0.01-2%, and crosslinking agent contains
Amount is 1-5%, filer content 28.99-68.99%%, when plasticizer loading is 10-50%, moisture-curable adhesive composition
Object has preferable operable time (surface drying time), tensile strength, tearing strength and water resistance.
As shown in comparative example 1, when the content of catalyst is less than 0.01%, the solidification of moisture-curable adhesive is too slow, i.e. table
The dry time is too long；When the content of catalyst is more than 2%, as shown in comparative example 4, solidification is too fast, i.e., surface drying time is too short, namely
Operable time is too short.As shown in the comparative example 1 and comparative example 3, when the content of Silante terminated polyolefin is less than 20% or filler
When content is more than 68.99%, moisture-curable clay hardness is excessive, causes water resistance bad；As shown in comparative example 2, work as silane
The content of polyolefin is blocked more than 60% or when the content of filler is less than 28.99%, the excessively viscous hand of adhesive, not easy to operate, nothing
Method testing water-proof performance.As shown in comparative example 5, when the content of plasticizer is more than 50%, plasticizer has precipitation phenomenon, and solid
The intensity of glue is weaker after change.As shown in comparative example 2, more crosslinking agent has lower-molecular substance precipitation after leading to adhesive curing；Such as
Shown in comparative example 1, when the content of crosslinking agent is too low, the intensity after adhesive curing can be influenced so that tensile strength and tearing strength
It is relatively low.As can be seen from Table 4, the moisture-curable adhesive prepared with Silante terminated polyolefin polymer, water vapor transmittance
About 10~13g/ (m2For 24 hours), it is much smaller than by the moisture-curable prepared by hydroxy-terminated polysiloxane and silane-terminated polyether
22~25g/ (m of adhesive2For 24 hours), shown in comparative example 6~8.
Claims (10)
1. a kind of silane-terminated polymer, which is characterized in that include the component of following percent by weight：The end hydroxyl of 70-95%
Base polybutadiene, the silane containing reactive functional groups of 4.98-29.5%, the catalyst A of 0.01-0.5%；It is described to contain reactivity
The silane of functional group is can be with the silane of hydroxyl reaction.
2. silane-terminated polymer according to claim 1, which is characterized in that the molecular weight of the end hydroxy butadiene
For 1000-3000, degree of functionality is 2~2.6.
3. silane-terminated polymer according to claim 2, which is characterized in that the silane containing reactive functional groups is
One or more of isocynate silane, epoxy silane.
4. silane-terminated polymer according to claim 1, which is characterized in that the catalyst A is oxalic acid dibutyl
One or more of tin, dibutyltin dilaurate and stannous octoate.
5. a kind of moisture-curable adhesive compound, which is characterized in that include the component of following percent by weight：20-60%
Any one of the claim 1-4 silane-terminated polymer, the crosslinking agent of the catalyst B, 1-5% of 0.01-2%, 28.99-
68.99% filler, the plasticizer of 10-50%.
6. moisture-curable adhesive compound according to claim 5, which is characterized in that the silane-terminated polymer
Weight percentage is 20-55%.
7. moisture-curable adhesive compound according to claim 5, which is characterized in that the catalyst B is oxalic acid
One or more of dibutyl tin, dibutyltin dilaurate and stannous octoate；The weight percentage of the catalyst B is
0.05%-1.1%.
8. moisture-curable cement compositions according to claim 5, which is characterized in that the crosslinking agent is γ-mercapto propyl
Triethoxysilane, γ-mercaptopropyl trimethoxysilane, methyltriethoxysilane, tetramethoxy-silicane, tetrapropoxy-silicane
It is alkane, tetraethoxysilane and triacetoxyl group ethylsilane, methyl triacetoxysilane, methyltrimethoxysilane, three (different
Allyloxy) vinyl silanes, methyl tributanoximo silane, vinyltrimethoxysilane, 3- (the third oxygen of 2,3- epoxies) third
One or more of base trimethoxy silane；The weight percentage of the crosslinking agent is 2-4%.
9. moisture-curable cement compositions according to claim 5, which is characterized in that the filler is calcium carbonate, kaolinite
Soil, molecular sieve, powder talcum powder, wollastonite, titanium dioxide, blanc fixe, carbon black, montmorillonite, silica, Al2O3, glass fibers
One or more of in dimension, graphite, the filler weight percentage composition is 30.5-63.95%.
10. moisture-curable cement compositions according to claim 5, which is characterized in that the plasticizer is paraffin oil, ring
One or more of alkane oil, dimethicone, dioctyl terephthalate, dibutyl terephthalate, the plasticizer
Weight percentage is 10-20%.
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Cited By (6)
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| CN111154445A (en) * | 2020-01-17 | 2020-05-15 | 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 |
| CN112680175A (en) * | 2020-12-14 | 2021-04-20 | 深圳斯多福新材料科技有限公司 | UV (ultraviolet) moisture dual-curing silica gel |
| CN114410214A (en) * | 2022-01-25 | 2022-04-29 | 宏源防水科技集团有限公司 | High-water-resistance polyurethane waterproof coating and preparation method thereof |
| CN114670294A (en) * | 2022-03-31 | 2022-06-28 | 安徽省科晟生态木装饰材料有限公司 | High-strength ecological plate and manufacturing process |
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| CN114410214A (en) * | 2022-01-25 | 2022-04-29 | 宏源防水科技集团有限公司 | High-water-resistance polyurethane waterproof coating and preparation method thereof |
| 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 |
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Denomination of invention: The invention relates to a silane terminated polymer and a moisture curing adhesive composition prepared therefrom Effective date of registration: 20210125 Granted publication date: 20200731 Pledgee: Bank of Jiaxing Limited by Share Ltd. Jiashan branch Pledgor: Zhejiang Ouren New Materials Co.,Ltd. Registration number: Y2021980000708 |
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Effective date of registration: 20220331 Address after: 314100 No. 17, Yinhe Road, Yao Zhuang Town, Jiashan County, Jiaxing, Zhejiang. Patentee after: ZHEJIANG FULAI NEW MATERIAL Co.,Ltd. Patentee after: Zhejiang OuRen New Material Co., Ltd Address before: 314100 1st floor, building 1, 17 Yinhe Road, Yaozhuang Town, Jiashan County, Jiaxing City, Zhejiang Province Patentee before: ZHEJIANG OUREN NEW MATERIALS Co.,Ltd. |