CN113583592A - Addition type room temperature curing tackifier and preparation method and application thereof - Google Patents
Addition type room temperature curing tackifier and preparation method and application thereof Download PDFInfo
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- CN113583592A CN113583592A CN202110817203.XA CN202110817203A CN113583592A CN 113583592 A CN113583592 A CN 113583592A CN 202110817203 A CN202110817203 A CN 202110817203A CN 113583592 A CN113583592 A CN 113583592A
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- tackifier
- room temperature
- chloropropyl
- temperature curing
- dropwise adding
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- 238000002360 preparation method Methods 0.000 title abstract description 9
- -1 vinyl chloropropyl Chemical group 0.000 claims abstract description 40
- 238000002156 mixing Methods 0.000 claims abstract description 32
- 229920002545 silicone oil Polymers 0.000 claims abstract description 29
- DOYKFSOCSXVQAN-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CCO[Si](C)(OCC)CCCOC(=O)C(C)=C DOYKFSOCSXVQAN-UHFFFAOYSA-N 0.000 claims abstract description 14
- KNTKCYKJRSMRMZ-UHFFFAOYSA-N 3-chloropropyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CCCCl KNTKCYKJRSMRMZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims abstract description 14
- ZLNAFSPCNATQPQ-UHFFFAOYSA-N ethenyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C=C ZLNAFSPCNATQPQ-UHFFFAOYSA-N 0.000 claims abstract description 14
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000007822 coupling agent Substances 0.000 claims abstract description 11
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 11
- 150000003624 transition metals Chemical class 0.000 claims abstract description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 238000003756 stirring Methods 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 22
- 238000010438 heat treatment Methods 0.000 claims description 15
- 238000001035 drying Methods 0.000 claims description 13
- 239000000395 magnesium oxide Substances 0.000 claims description 13
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 13
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 13
- 230000001681 protective effect Effects 0.000 claims description 13
- 239000002994 raw material Substances 0.000 claims description 13
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 13
- 238000004321 preservation Methods 0.000 claims description 11
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 10
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 6
- 150000004645 aluminates Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 229920001296 polysiloxane Polymers 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- GVXYMVJBUCMDJE-UHFFFAOYSA-K C(CCCCCCCCCCCCCCCCC)(=O)[O-].C(CC)O[Ti+3].C(CCCCCCCCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCCCCCCCC)(=O)[O-] Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)[O-].C(CC)O[Ti+3].C(CCCCCCCCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCCCCCCCC)(=O)[O-] GVXYMVJBUCMDJE-UHFFFAOYSA-K 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 2
- 230000001070 adhesive effect Effects 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 239000002318 adhesion promoter Substances 0.000 claims 5
- 239000007983 Tris buffer Substances 0.000 claims 1
- 229940049964 oleate Drugs 0.000 claims 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
- 238000004382 potting Methods 0.000 claims 1
- 239000000565 sealant Substances 0.000 abstract description 12
- 239000000463 material Substances 0.000 abstract description 8
- 238000005303 weighing Methods 0.000 description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 238000004821 distillation Methods 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 239000012812 sealant material Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 4
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229940093858 ethyl acetoacetate Drugs 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- 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
- C09J11/08—Macromolecular additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2170/00—Compositions for adhesives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention provides an addition type room temperature curing tackifier and a preparation method and application thereof, wherein the tackifier comprises an oligomeric siloxane tackifier and a transition metal coupling agent which are mixed and prepared according to a certain mass ratio, wherein the oligomeric siloxane tackifier is prepared by mixing gamma chloropropyl methyl dimethoxy silane and methyl vinyl dimethoxy silane to prepare hydroxyl-terminated vinyl chloropropyl silicone oil in advance, and then condensing the hydroxyl-terminated vinyl chloropropyl silicone oil with gamma-glycidyl ether oxypropyl triethoxy silane and methacryloxypropyl methyl diethoxy silane to prepare the oligomeric siloxane tackifier. The tackifier disclosed by the invention is low in curing temperature, has good cohesiveness with different materials, can be applied to the field of pouring sealants, and has a good application prospect.
Description
Technical Field
The invention relates to the technical field of silicone rubber bonding sealing materials, in particular to an addition type room temperature curing tackifier and a preparation method and application thereof.
Background
Along with the continuous development of integrated circuit boards, the integration of electronic elements is higher and higher, the requirements on the working environment are also higher and higher, and in order to avoid the failure of the integrated circuit due to the influence of the external environment, the electronic elements need to be sealed, cured and protected by electronic pouring sealant.
Common pouring sealant materials comprise epoxy pouring sealant materials, polyurethane pouring sealant materials and organic siloxane pouring sealant materials, wherein the epoxy pouring sealant materials are stable in chemical properties, good in insulativity and capable of having certain adhesion to various materials, but the cured materials are large in brittleness and easy to crack at low temperature, and the polyurethane pouring sealant materials are poor in high-temperature performance, easy to age and fall off powder and easy to burn at high temperature; the organic siloxane encapsulating material has good chemical stability and strong mechanical stability, the material has elasticity and good electrical property, and has good protection effect on electronic elements, wherein the addition type organic siloxane encapsulating material is widely applied due to the factors that the shrinkage rate is small in the curing process, small molecules are not generated, the curing process is not influenced by moisture, and the like.
Disclosure of Invention
In view of the above, the invention provides an addition type room temperature curing tackifier and a preparation method and application thereof.
The technical scheme of the invention is realized as follows: the invention provides an addition type room temperature curing tackifier, which comprises an oligomeric siloxane tackifier and a transition metal coupling agent, wherein the oligomeric siloxane tackifier has the following structural formula:
wherein a and b are positive integers, the value range of a is 1-10, and the value range of b is 1-10.
On the basis of the above technical scheme, preferably, the transition metal coupling agent is one of titanate, zirconate or aluminate.
On the basis of the technical scheme, preferably, the titanate is one of propoxytitanium tristearate, isopropoxy trioleate acyloxy titanate, neoalkoxy tri (neodecanoic acyloxy) titanate, bis (acetoacetic acid ethyl ester) di-n-butoxy titanate and polytitanium ester butyl ester.
In addition to the above technical means, preferably, the zirconate is one of neoalkoxy tri (acryloyloxy) zirconate, neoalkoxy tri (methacryloyloxy) zirconate, and neoalkoxy tri (neodecanoyloxy) zirconate.
Still more preferably, the aluminate is one of aluminum triacetylacetonate, diisopropoxylacetoacetanoate, and (ethylacetoacetate) diisopropoxyaluminate.
On the basis of the technical scheme, preferably, the mass ratio of the oligomeric siloxane tackifier to the transition metal coupling agent is 1: (0.8-1.4).
On the basis of the technical scheme, preferably, the preparation method of the oligomeric siloxane tackifier comprises the following steps:
respectively mixing gamma-chloropropyl methyl dimethoxysilane and methyl vinyl dimethoxysilane, dropwise adding water into the mixture, adding magnesium oxide for reaction after the dropwise adding is finished, drying and removing water after the reaction is finished, and distilling unreacted raw materials to obtain hydroxyl-terminated vinyl chloropropyl silicone oil;
and then mixing the hydroxyl-terminated vinyl chloropropyl silicone oil, glycol and isopropyl titanate, heating and stirring to 80-100 ℃ under the atmosphere of protective gas, dropwise adding gamma-glycidyl ether oxypropyl triethoxysilane and methacryloxypropyl methyl diethoxysilane into the system, reacting for 1h under heat preservation, and then cooling to 25 ℃ to obtain the oligosiloxane tackifier.
The concrete reaction formula is as follows:
wherein a and b are positive integers, the value range of a is 1-10, and the value range of b is 1-10.
The invention also provides a preparation method of the addition type room temperature curing tackifier, which comprises the following step of uniformly mixing the oligosiloxane tackifier and the transition metal coupling agent according to the mass ratio to obtain the addition type room temperature curing tackifier.
The addition type room temperature curing tackifier prepared by the scheme can be used in room temperature curing organic silicon pouring sealant.
Compared with the prior art, the addition type room temperature curing tackifier and the preparation method and application thereof have the following beneficial effects:
(1) the conventional tackifier generally needs higher curing temperature, and the specific oligomeric siloxane tackifier is adopted in the application, wherein an active agent group still has higher activity at room temperature, so that the tackifier has certain room temperature curing capability, and a transition metal coupling agent is added, so that the low-temperature activity of the tackifier is further improved, and the tackifier has better curing capability at room temperature
(2) The low polysiloxane tackifier in the tackifier disclosed by the application has an epoxy group and an ester group, the epoxy group and the ester group respectively have good viscosity to inorganic materials and organic materials, the whole viscosity of a system can be improved by introducing a vinyl group, the curing temperature can be reduced by adding a transition metal coupling agent, the bonding strength is improved, and the low polysiloxane tackifier can be applied to a pouring sealant and can improve the mechanical strength of the pouring sealant after being cured.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be obtained by a person skilled in the art without any inventive step based on the embodiments of the present invention, are within the scope of the present invention.
Example 1
The oligosiloxane tackifier was first prepared:
weighing 19g of gamma chloropropyl methyl dimethoxysilane and 14g of methyl vinyl dimethoxysilane, uniformly mixing, dropwise adding water into a mixed system, wherein the amount of the dropwise added water is 17g, the dropwise adding time is 50min, after the dropwise adding is finished, adding 0.3g of magnesium oxide, stirring for reacting for 3h, adding anhydrous magnesium sulfate, drying, filtering, heating the rest reaction system to 83 ℃, distilling to obtain hydroxyl-terminated vinyl chloropropyl silicone oil after unreacted raw materials are evaporated, and weighing to obtain 25.3g of a product.
Mixing 25.3g of hydroxyl-terminated vinyl chloropropyl silicone oil, 20ml of ethylene glycol and 0.2g of isopropyl titanate, placing the mixture in a nitrogen protective atmosphere, heating to 80 ℃, dropwise adding 25g of gamma-glycidyl ether oxypropyl triethoxysilane into the system, controlling the dropwise adding time to be 50min, dropwise adding 25g of methacryloxypropyl methyldiethoxysilane into the system after the dropwise adding is finished, controlling the dropwise adding time to be 50min, preserving heat for reacting for 1h after the dropwise adding is finished, and then cooling to 25 ℃ to obtain the oligosiloxane tackifier.
Preparing a compound tackifier:
respectively weighing 50g of oligosiloxane tackifier and 40g of titanium propoxide tristearate, and uniformly mixing and stirring to obtain the addition type room temperature curing tackifier.
Example 2
The oligosiloxane tackifier was first prepared:
weighing 19g of gamma chloropropyl methyl dimethoxysilane and 14g of methyl vinyl dimethoxysilane, uniformly mixing, dropwise adding water into a mixed system, wherein the amount of the dropwise added water is 17g, the dropwise adding time is 60min, after the dropwise adding is finished, adding 0.3g of magnesium oxide, stirring for reacting for 4h, adding anhydrous magnesium sulfate, drying, filtering, heating the rest reaction system to 84 ℃ for distillation, evaporating unreacted raw materials to obtain hydroxyl-terminated vinyl chloropropyl silicone oil, and weighing to obtain 24.6g of a product.
24.6g of hydroxyl-terminated vinyl chloropropyl silicone oil, 20ml of ethylene glycol and 0.2g of isopropyl titanate are mixed, the mixture is placed in a nitrogen protective atmosphere, the temperature is heated to 85 ℃, 25g of gamma-glycidyl ether oxypropyl triethoxysilane is dripped into the system, the dripping time is controlled to be 50min, after the dripping is finished, 25g of methacryloxypropyl methyldiethoxysilane is dripped into the system, the dripping time is controlled to be 50min, after the dripping is finished, the heat preservation reaction is carried out for 1h, and then the mixture is cooled to 25 ℃, so that the oligosiloxane tackifier is obtained.
Preparing a compound tackifier:
respectively weighing 50g of oligosiloxane tackifier and 45g of isopropoxy trioleoxy titanate, and uniformly mixing and stirring to obtain the addition type room temperature curing tackifier.
Example 3
The oligosiloxane tackifier was first prepared:
weighing 19g of gamma chloropropyl methyl dimethoxysilane and 14g of methyl vinyl dimethoxysilane, uniformly mixing, dropwise adding water into a mixed system, wherein the amount of the dropwise added water is 17g, the dropwise adding time is 60min, after the dropwise adding is finished, adding 0.3g of magnesium oxide, stirring for reacting for 4h, adding anhydrous magnesium sulfate, drying, filtering, heating the rest reaction system to 84 ℃ for distillation, evaporating unreacted raw materials to obtain hydroxyl-terminated vinyl chloropropyl silicone oil, and weighing to obtain 24.3g of a product.
24.3g of hydroxyl-terminated vinyl chloropropyl silicone oil, 20ml of ethylene glycol and 0.2g of isopropyl titanate are mixed, the mixture is placed in a nitrogen protective atmosphere, the temperature is heated to 85 ℃, 25g of gamma-glycidyl ether oxypropyl triethoxysilane is dripped into the system, the dripping time is controlled to be 50min, after the dripping is finished, 25g of methacryloxypropyl methyldiethoxysilane is dripped into the system, the dripping time is controlled to be 50min, after the dripping is finished, the heat preservation reaction is carried out for 1h, and then the mixture is cooled to 25 ℃, so that the oligosiloxane tackifier is obtained.
Preparing a compound tackifier:
respectively weighing 50g of oligosiloxane tackifier and 50g of neoalkoxy tri (neodecanoic acyloxy) titanate, and uniformly mixing and stirring to obtain the addition type room temperature curing tackifier.
Example 4
The oligosiloxane tackifier was first prepared:
weighing 19g of gamma chloropropyl methyl dimethoxysilane and 14g of methyl vinyl dimethoxysilane, uniformly mixing, dropwise adding water into a mixed system, wherein the amount of the dropwise added water is 17g, the dropwise adding time is 60min, after the dropwise adding is finished, adding 0.3g of magnesium oxide, stirring for reacting for 4h, adding anhydrous magnesium sulfate, drying, filtering, heating the rest reaction system to 82 ℃ for distillation, evaporating unreacted raw materials to obtain hydroxyl-terminated vinyl chloropropyl silicone oil, and weighing to obtain 25.5g of a product.
Mixing 25.5g of hydroxyl-terminated vinyl chloropropyl silicone oil, 20ml of ethylene glycol and 0.2g of isopropyl titanate, placing the mixture in a nitrogen protective atmosphere, heating to 85 ℃, dropwise adding 25g of gamma-glycidyl ether oxypropyl triethoxysilane into the system, controlling the dropwise adding time to be 50min, dropwise adding 25g of methacryloxypropyl methyldiethoxysilane into the system after the dropwise adding is finished, controlling the dropwise adding time to be 50min, preserving heat for reacting for 1h after the dropwise adding is finished, and then cooling to 25 ℃ to obtain the oligosiloxane tackifier.
Preparing a compound tackifier:
respectively weighing 50g of oligosiloxane tackifier and 55g of bis (ethyl acetoacetate) di-n-butoxy titanate, and uniformly mixing and stirring to obtain the addition type room temperature curing tackifier.
Example 5
The oligosiloxane tackifier was first prepared:
weighing 19g of gamma chloropropyl methyl dimethoxysilane and 14g of methyl vinyl dimethoxysilane, uniformly mixing, dropwise adding water into a mixed system, wherein the amount of the dropwise added water is 17g, the dropwise adding time is 70min, after the dropwise adding is finished, adding 0.3g of magnesium oxide, stirring for reacting for 4h, adding anhydrous magnesium sulfate, drying, filtering, heating the rest reaction system to 84 ℃ for distillation, evaporating unreacted raw materials to obtain hydroxyl-terminated vinyl chloropropyl silicone oil, and weighing to obtain 24.5g of a product.
24.5g of hydroxyl-terminated vinyl chloropropyl silicone oil, 20ml of ethylene glycol and 0.2g of isopropyl titanate are mixed, the mixture is placed in a nitrogen protective atmosphere, the temperature is heated to 85 ℃, 25g of gamma-glycidyl ether oxypropyl triethoxysilane is dripped into the system, the dripping time is controlled to be 50min, after the dripping is finished, 25g of methacryloxypropyl methyldiethoxysilane is dripped into the system, the dripping time is controlled to be 50min, after the dripping is finished, the heat preservation reaction is carried out for 1h, and then the mixture is cooled to 25 ℃, so that the oligosiloxane tackifier is obtained.
Preparing a compound tackifier:
respectively weighing 50g of oligosiloxane tackifier and 60g of poly-titanium ester butyl ester, and uniformly mixing and stirring to obtain the addition type room temperature curing tackifier.
Example 6
The oligosiloxane tackifier was first prepared:
weighing 19g of gamma chloropropyl methyl dimethoxysilane and 14g of methyl vinyl dimethoxysilane, uniformly mixing, dropwise adding water into a mixed system, wherein the amount of the dropwise added water is 17g, the dropwise adding time is 70min, after the dropwise adding is finished, adding 0.3g of magnesium oxide, stirring for reacting for 4h, adding anhydrous magnesium sulfate, drying, filtering, heating the rest reaction system to 84 ℃ for distillation, evaporating unreacted raw materials to obtain hydroxyl-terminated vinyl chloropropyl silicone oil, and weighing to obtain 24.4g of a product.
24.4g of hydroxyl-terminated vinyl chloropropyl silicone oil, 20ml of ethylene glycol and 0.2g of isopropyl titanate are mixed, the mixture is placed in a nitrogen protective atmosphere, the temperature is heated to 85 ℃, 25g of gamma-glycidyl ether oxypropyl triethoxysilane is dripped into the system, the dripping time is controlled to be 60min, after the dripping is finished, 25g of methacryloxypropyl methyldiethoxysilane is dripped into the system, the dripping time is controlled to be 60min, after the dripping is finished, the heat preservation reaction is carried out for 1h, and then the mixture is cooled to 25 ℃, so that the oligosiloxane tackifier is obtained.
Preparing a compound tackifier:
respectively weighing 50g of oligosiloxane tackifier and 65g of neoalkoxy tri (acryloxy) zirconate, and uniformly mixing and stirring to obtain the addition type room temperature curing tackifier.
Example 7
The oligosiloxane tackifier was first prepared:
weighing 19g of gamma chloropropyl methyl dimethoxysilane and 14g of methyl vinyl dimethoxysilane, uniformly mixing, dropwise adding water into a mixed system, wherein the amount of the dropwise added water is 17g, the dropwise adding time is 60min, after the dropwise adding is finished, adding 0.3g of magnesium oxide, stirring for reacting for 4h, adding anhydrous magnesium sulfate, drying, filtering, heating the rest reaction system to 83 ℃, distilling to obtain hydroxyl-terminated vinyl chloropropyl silicone oil after unreacted raw materials are evaporated, and weighing to obtain 24.6g of a product.
24.6g of hydroxyl-terminated vinyl chloropropyl silicone oil, 20ml of ethylene glycol and 0.2g of isopropyl titanate are mixed, the mixture is placed in a nitrogen protective atmosphere, the temperature is heated to 85 ℃, 25g of gamma-glycidyl ether oxypropyl triethoxysilane is dripped into the system, the dripping time is controlled to be 60min, after the dripping is finished, 25g of methacryloxypropyl methyldiethoxysilane is dripped into the system, the dripping time is controlled to be 60min, after the dripping is finished, the heat preservation reaction is carried out for 1h, and then the mixture is cooled to 25 ℃, so that the oligosiloxane tackifier is obtained.
Preparing a compound tackifier:
respectively weighing 50g of oligosiloxane tackifier and 70g of neoalkoxy tri (methacryloxy) zirconate, and uniformly mixing and stirring to obtain the addition type room temperature curing tackifier.
Example 8
The oligosiloxane tackifier was first prepared:
weighing 19g of gamma chloropropyl methyl dimethoxysilane and 14g of methyl vinyl dimethoxysilane, uniformly mixing, dropwise adding water into a mixed system, wherein the amount of the dropwise added water is 17g, the dropwise adding time is 60min, after the dropwise adding is finished, adding 0.3g of magnesium oxide, stirring for reacting for 4h, adding anhydrous magnesium sulfate, drying, filtering, heating the rest reaction system to 83 ℃, distilling to obtain hydroxyl-terminated vinyl chloropropyl silicone oil after unreacted raw materials are evaporated, and weighing to obtain 24.5g of a product.
24.5g of hydroxyl-terminated vinyl chloropropyl silicone oil, 20ml of ethylene glycol and 0.2g of isopropyl titanate are mixed, the mixture is placed in a nitrogen protective atmosphere, the temperature is heated to 85 ℃, 25g of gamma-glycidyl ether oxypropyl triethoxysilane is dripped into the system, the dripping time is controlled to be 50min, after the dripping is finished, 25g of methacryloxypropyl methyldiethoxysilane is dripped into the system, the dripping time is controlled to be 50min, after the dripping is finished, the heat preservation reaction is carried out for 1h, and then the mixture is cooled to 25 ℃, so that the oligosiloxane tackifier is obtained.
Preparing a compound tackifier:
respectively weighing 50g of oligosiloxane tackifier and 70g of neoalkoxy tri (neodecanoic acyloxy) zirconate, and uniformly mixing and stirring to obtain the addition type room temperature curing tackifier.
Example 9
The oligosiloxane tackifier was first prepared:
weighing 19g of gamma chloropropyl methyl dimethoxysilane and 14g of methyl vinyl dimethoxysilane, uniformly mixing, dropwise adding water into a mixed system, wherein the amount of the dropwise added water is 17g, the dropwise adding time is 60min, after the dropwise adding is finished, adding 0.3g of magnesium oxide, stirring for reacting for 4h, adding anhydrous magnesium sulfate, drying, filtering, heating the rest reaction system to 83 ℃, distilling to obtain hydroxyl-terminated vinyl chloropropyl silicone oil after unreacted raw materials are evaporated, and weighing to obtain 24.5g of a product.
24.5g of hydroxyl-terminated vinyl chloropropyl silicone oil, 20ml of ethylene glycol and 0.2g of isopropyl titanate are mixed, the mixture is placed in a nitrogen protective atmosphere, the temperature is heated to 85 ℃, 25g of gamma-glycidyl ether oxypropyl triethoxysilane is dripped into the system, the dripping time is controlled to be 50min, after the dripping is finished, 25g of methacryloxypropyl methyldiethoxysilane is dripped into the system, the dripping time is controlled to be 50min, after the dripping is finished, the heat preservation reaction is carried out for 1h, and then the mixture is cooled to 25 ℃, so that the oligosiloxane tackifier is obtained.
Preparing a compound tackifier:
respectively weighing 50g of oligosiloxane tackifier and 70g of aluminum triacetylacetone, and uniformly mixing and stirring to obtain the addition type room temperature curing tackifier.
Example 10
The oligosiloxane tackifier was first prepared:
weighing 19g of gamma chloropropyl methyl dimethoxysilane and 14g of methyl vinyl dimethoxysilane, uniformly mixing, dropwise adding water into a mixed system, wherein the amount of the dropwise added water is 17g, the dropwise adding time is 60min, after the dropwise adding is finished, adding 0.3g of magnesium oxide, stirring for reacting for 4h, adding anhydrous magnesium sulfate, drying, filtering, heating the rest reaction system to 82 ℃ for distillation, evaporating unreacted raw materials to obtain hydroxyl-terminated vinyl chloropropyl silicone oil, and weighing to obtain 24.8g of a product.
24.8g of hydroxyl-terminated vinyl chloropropyl silicone oil, 20ml of ethylene glycol and 0.2g of isopropyl titanate are mixed, the mixture is placed in a nitrogen protective atmosphere, the temperature is heated to 85 ℃, 25g of gamma-glycidyl ether oxypropyl triethoxysilane is dripped into the system, the dripping time is controlled to be 50min, after the dripping is finished, 25g of methacryloxypropyl methyldiethoxysilane is dripped into the system, the dripping time is controlled to be 50min, after the dripping is finished, the heat preservation reaction is carried out for 1h, and then the mixture is cooled to 25 ℃, so that the oligosiloxane tackifier is obtained.
Preparing a compound tackifier:
respectively weighing 50g of oligosiloxane tackifier and 70g of (ethyl acetoacetate) diisopropoxy aluminate, and uniformly mixing and stirring to obtain the addition type room temperature curing tackifier.
Example 11
The oligosiloxane tackifier was first prepared:
weighing 19g of gamma chloropropyl methyl dimethoxysilane and 14g of methyl vinyl dimethoxysilane, uniformly mixing, dropwise adding water into a mixed system, wherein the amount of the dropwise added water is 17g, the dropwise adding time is 60min, after the dropwise adding is finished, adding 0.3g of magnesium oxide, stirring for reacting for 4h, adding anhydrous magnesium sulfate, drying, filtering, heating the rest reaction system to 82 ℃ for distillation, evaporating unreacted raw materials to obtain hydroxyl-terminated vinyl chloropropyl silicone oil, and weighing to obtain 24.8g of a product.
24.8g of hydroxyl-terminated vinyl chloropropyl silicone oil, 20ml of ethylene glycol and 0.2g of isopropyl titanate are mixed, the mixture is placed in a nitrogen protective atmosphere, the temperature is heated to 85 ℃, 25g of gamma-glycidyl ether oxypropyl triethoxysilane is dripped into the system, the dripping time is controlled to be 50min, after the dripping is finished, 25g of methacryloxypropyl methyldiethoxysilane is dripped into the system, the dripping time is controlled to be 50min, after the dripping is finished, the heat preservation reaction is carried out for 1h, and then the mixture is cooled to 25 ℃, so that the oligosiloxane tackifier is obtained.
Preparing a compound tackifier:
respectively weighing 50g of oligosiloxane tackifier and 70g of diisopropoxy acetoacetic acid oleyl aluminate, and uniformly mixing and stirring to obtain the addition type room temperature curing tackifier.
Comparative example:
a commercially available silicone tackifier was used as a comparative example.
The tackifier prepared in the embodiment and the comparative proportion is respectively used for preparing the organic silicon pouring sealant, and the pouring sealant is used for detecting the bonding strength and the curing temperature, and the preparation method specifically comprises the following steps:
and uniformly mixing the filler, the silicone oil, the tackifier, the inhibitor and the catalyst, and performing defoaming treatment to obtain the pouring sealant.
The pouring sealant is smeared on the surfaces of different base materials, is cured for 24 hours at 25 ℃, and then is subjected to mechanical property test, wherein the test result is as follows:
| testing of performance of aluminum plate | Tensile strength/MPa | Rockwell hardness | Adhesive strength/MPa |
| Example 1 | 1.9 | 62 | 1.33 |
| Example 2 | 1.9 | 62 | 1.29 |
| Example 3 | 1.9 | 63 | 1.29 |
| Example 4 | 1.9 | 62 | 1.28 |
| Example 5 | 1.9 | 62 | 1.32 |
| Example 6 | 1.9 | 61 | 1.24 |
| Example 7 | 1.9 | 61 | 1.25 |
| Example 8 | 1.9 | 60 | 1.24 |
| Example 9 | 1.9 | 55 | 1.19 |
| Example 10 | 1.9 | 56 | 1.20 |
| Example 11 | 1.9 | 56 | 1.18 |
| Comparative example | 0.02 | - | 0.02 |
It is easy to see that the tackifier of the invention can realize the curing of the pouring sealant at 25 ℃, compared with the conventional pouring sealant, the curing temperature is lower, the tackifier has good bonding strength with different materials, and the obtained pouring sealant body also has good tensile strength and hardness, and has good application prospect.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (9)
1. The addition type room temperature curing tackifier is characterized by comprising an oligomeric siloxane tackifier and a transition metal coupling agent, wherein the oligomeric siloxane tackifier has the following structural formula:
wherein a and b are both positive integers.
2. The addition room temperature curing adhesion promoter of claim 1, wherein the transition metal coupling agent is one of a titanate, a zirconate, or an aluminate.
3. The addition room temperature cure adhesion promoter of claim 2, wherein the titanate is one of titanium propoxide tristearate, isopropoxytrioleate acyloxy titanate, neoalkoxy tris (neodecanoate acyloxy) titanate, bis (ethyl acetoacetate) di-n-butoxy titanate, and poly-titanium butyl ester.
4. The addition room temperature cure adhesion promoter of claim 2, wherein the zirconate is one of neoalkoxy tri (acryloxy) zirconate, neoalkoxy tri (methacryloxy) zirconate, and neoalkoxy tri (neodecanoyloxy) zirconate.
5. The addition room temperature curing adhesion promoter of claim 2, wherein the aluminate is one of aluminum triacetylacetonate, diisopropoxylacetoacetanoate oleate and (ethyl acetoacetate) diisopropoxyaluminate.
6. The addition room temperature curing tackifier of claim 1, wherein the oligomeric siloxane tackifier and the transition metal coupling agent are present in a mass ratio of 1: (0.8-1.4).
7. The addition room temperature curing tackifier of claim 1, wherein the oligomeric silicone tackifier is prepared by a process comprising the steps of:
respectively mixing gamma-chloropropyl methyl dimethoxysilane and methyl vinyl dimethoxysilane, dropwise adding water into the mixture, adding magnesium oxide for reaction after the dropwise adding is finished, drying and removing water after the reaction is finished, and distilling unreacted raw materials to obtain hydroxyl-terminated vinyl chloropropyl silicone oil;
and then mixing the hydroxyl-terminated vinyl chloropropyl silicone oil, glycol and isopropyl titanate, heating and stirring to 80-100 ℃ under the atmosphere of protective gas, dropwise adding gamma-glycidyl ether oxypropyl triethoxysilane and methacryloxypropyl methyl diethoxysilane into the system, reacting for 1h under heat preservation, and then cooling to 25 ℃ to obtain the oligosiloxane tackifier.
8. The method for preparing the addition type room temperature curing tackifier of any one of claims 1 to 7, wherein the method does not comprise the following step of uniformly mixing the oligosiloxane tackifier and the transition metal coupling agent according to the mass ratio to obtain the addition type room temperature curing tackifier.
9. Use of the addition type room temperature curing adhesion promoter as claimed in any one of claims 1 to 7 in a silicone potting adhesive.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114231247A (en) * | 2021-11-30 | 2022-03-25 | 湖北双键精细化工有限公司 | Room-temperature-curing two-component addition-type self-adhesive high-temperature-resistant silica gel and preparation method thereof |
| CN115975461A (en) * | 2023-02-28 | 2023-04-18 | 信和新材料（苏州）有限公司 | Heat-insulating anti-condensation coating, and preparation method and application thereof |
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2021
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114231247A (en) * | 2021-11-30 | 2022-03-25 | 湖北双键精细化工有限公司 | Room-temperature-curing two-component addition-type self-adhesive high-temperature-resistant silica gel and preparation method thereof |
| CN115975461A (en) * | 2023-02-28 | 2023-04-18 | 信和新材料（苏州）有限公司 | Heat-insulating anti-condensation coating, and preparation method and application thereof |
| CN115975461B (en) * | 2023-02-28 | 2024-03-08 | 信和新材料（苏州）有限公司 | Heat-insulating anti-condensation coating, and preparation method and application thereof |
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