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CN109096945B - Tackifier applied to silicone sealant and preparation method thereof - Google Patents

Tackifier applied to silicone sealant and preparation method thereof Download PDF

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Publication number
CN109096945B
CN109096945B CN201810637038.8A CN201810637038A CN109096945B CN 109096945 B CN109096945 B CN 109096945B CN 201810637038 A CN201810637038 A CN 201810637038A CN 109096945 B CN109096945 B CN 109096945B
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coupling agent
parts
tackifier
silicone sealant
isocyanate
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CN109096945A (en
Inventor
胡颖娟
郭蒙
胡颖慧
胡新嵩
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Hangzhou Shuangtouying Organic Silicone Technology Co.,Ltd.
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Guangzhou Leisiman New Material Technology Co ltd
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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
    • 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
    • C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
    • C09J183/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00—Specific properties of additives
    • C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5435—Silicon-containing compounds containing oxygen containing oxygen in a ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/544—Silicon-containing compounds containing nitrogen

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Sealing Material Composition (AREA)

Abstract

The invention relates to a tackifier applied to silicone sealant, which is prepared from the following components in parts by weight: 20-50 parts of titanate coupling agent, 20-50 parts of silane coupling agent and 1-10 parts of isocyanate. Compared with the prior art, the tackifier of the invention is used for silicone sealant, particularly after the condensed type single-component silicone sealant, the reversion phenomenon is not easy to occur under the heating condition, and the tackifier still has good tensile strength and elongation at break.

Description

Tackifier applied to silicone sealant and preparation method thereof
Technical Field
The invention relates to the field of flame-retardant polymer composite materials, in particular to a tackifier applied to silicone sealant and a preparation method of the tackifier.
Background
The silicone sealant is a paste prepared by mixing polydimethylsiloxane as a main raw material and a crosslinking agent, a filler, a plasticizer, a coupling agent, a catalyst and the like as auxiliary materials in a vacuum state. The silicone sealant has the characteristics of strong bonding force, high tensile strength, weather resistance, vibration resistance, moisture resistance and large adaptability to cold and heat changes. In addition, the wide applicability of the adhesive can realize the adhesion among most building material products, so the application value is very high.
The silicone sealant is mainly divided into a single-component silicone sealant and a double-component silicone sealant, and can also be divided into a condensation type sealant and an addition type sealant. The single-component and double-component silicone sealants are cured by a cross-linking agent under the action of a catalyst, and the condensation type silicone sealant is mainly different from the addition type silicone sealant in that: the former produces small molecules when cured, and the latter produces no other substances. And the former requires the participation of water in curing and the latter does not. For condensation type one-and two-component silicone sealants, the one-component cure is cured by reaction with moisture in the air, i.e., water, and the two-component cure is cured by reaction with a trace amount of moisture in the A-component. Currently, in the market, the main application is a condensed type single-component silicone sealant.
Although the silicone sealant has good heat resistance, when the silicone sealant is heated under a closed condition, Si-O bonds are broken due to the action of residual catalysts (organic tin compounds), so that the sealant becomes soft or even liquid, and the strength is reduced, and the phenomenon is called 'reversion'. At present, no relevant report for solving or improving the phenomenon exists. This phenomenon can be ameliorated by the addition of a tackifier to the silicone sealant.
In view of this, the invention is particularly proposed.
Disclosure of Invention
The first purpose of the invention is to provide a tackifier applied to a silicone sealant.
The second object of the present invention is to provide a method for producing the above tackifier.
In order to achieve the purpose, the technical scheme of the invention is as follows:
the invention relates to a tackifier applied to silicone sealant, which is prepared from the following components in parts by weight:
20-50 parts of titanate coupling agent, 20-50 parts of silane coupling agent and 1-10 parts of isocyanate.
Preferably, the tackifier is prepared from the following components in parts by weight: 30-45 parts of titanate coupling agent, 30-45 parts of silane coupling agent and 5-10 parts of isocyanate.
Preferably, the titanate coupling agent is isopropyl titanate and/or butyl titanate.
Preferably, the silane coupling agent is at least one selected from the group consisting of gamma-aminopropyltriethoxysilane, 1, 2-epoxyethoxytrimethoxysilane, gamma-glycidoxypropyltrimethoxysilane, and epoxycyclohexyltrimethoxysilane.
Preferably, the isocyanate is an aromatic polyisocyanate and/or an aliphatic polyisocyanate.
Preferably, the aromatic polyisocyanate is an aromatic diisocyanate selected from at least one of 2, 4-and 2, 6-Toluene Diisocyanate (TDI), 4' -, 2,4' -and 2,2' -diphenylmethane diisocyanate (MDI), 1, 3-and 1, 4-phenylene diisocyanate, 2,3,5, 6-tetramethyl-1, 4-diisocyanatobenzene, naphthalene-1, 5-diisocyanate (NDI), 3' -dimethyl-4, 4' -diisocyanatobiphenyl (TODI).
Preferably, the aliphatic polyisocyanate is an aliphatic diisocyanate selected from the group consisting of 1, 6-Hexamethylene Diisocyanate (HDI), 2-methylpentamethylene-1, 5-diisocyanate, 2, 4-and 2,4, 4-trimethyl-1, 6-hexamethylene diisocyanate (TMDI), 1, 12-dodecamethylene diisocyanate, lysine and lysine ester diisocyanate, cyclohexane-1, 3-diisocyanate, cyclohexane-1, 4-diisocyanate, 1-isocyanato-3, 3, 5-trimethyl-5-isocyanatomethyl-cyclohexane (isophorone diisocyanate or IPDI), perhydro-2, 4' -diphenylmethane diisocyanate and perhydro-4, 4' -diphenylmethane diisocyanate, 1, 4-diisocyanato-2, 2, 6-Trimethylcyclohexane (TMCDI), 1, 3-and 1, 4-bis (isocyanatomethyl) -cyclohexane.
Preferably, the isocyanate is a mixture of aromatic polyisocyanate and aliphatic polyisocyanate, and the molar ratio of the aromatic polyisocyanate to the aliphatic polyisocyanate is 1: (1-5).
The invention also relates to a preparation method of the tackifier, which comprises the following steps:
heating the titanate coupling agent and the silane coupling agent to 60-80 ℃, keeping the temperature for 10-30 min, adding isocyanate, and continuing to react for 30-60 min under the condition of keeping the temperature.
Preferably, the process is carried out under a protective gas atmosphere.
The invention has the beneficial effects that:
compared with the prior art, the tackifier of the invention is used for silicone sealant, particularly after the condensed type single-component silicone sealant, the reversion phenomenon is not easy to occur under the heating condition, and the tackifier still has good tensile strength and elongation at break.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be described in detail below. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the examples given herein without any inventive step, are within the scope of the present invention.
The embodiment of the invention relates to a tackifier applied to a silicone sealant, which is prepared from the following components in parts by weight:
20-50 parts of titanate coupling agent, preferably 30-45 parts;
20-50 parts of a silane coupling agent, preferably 30-45 parts;
1-10 parts of isocyanate, preferably 5-10 parts.
The tackifier has the main function of improving the self-adhesion of the sizing material, so that the diffusion capacity of the sizing material is enhanced, and the performance of the silicone sealant is not influenced. The concrete characteristics are that the mechanical property can not be reduced, the transparency and the glossiness can not be influenced, and a large amount of bubbles can not be generated during curing.
In one embodiment of the invention, the titanate coupling agent is isopropyl titanate and/or butyl titanate. The coupling agent is a substance with two functional groups with different properties, one is an inorganophilic group and is easy to chemically react with the surface of an inorganic substance; the other is an organophilic group which is capable of chemically reacting with or forming hydrogen bonds soluble in synthetic resins or other polymers. Therefore, the coupling agent is called a molecular bridge and is used for improving the interface action between inorganic matters and organic matters, thereby greatly improving the performance of the composite material. The titanate coupling agent has good coupling effect in filler systems such as thermoplastic plastics, thermosetting plastics, rubber and the like.
The common coupling agents at present are silane coupling agents and titanate coupling agents. The silane coupling agent is only effective to the filler containing silicon, while the titanium coupling agent is applicable to various fillers, and the applicable substance range is wider. And the titanate coupling agent has the functions of improving the strength of the composite material and endowing the material with certain flexibility.
In one embodiment of the present invention, the silane coupling agent is selected from at least one of gamma-aminopropyltriethoxysilane, 1, 2-epoxyethoxytrimethoxysilane, gamma-glycidoxypropyltrimethoxysilane, epoxycyclohexyltrimethoxysilane.
The molecular structural formula of the silane coupling agent is generally Y-R-Si (OR)3(wherein Y is an organic functional group and SiOR is a siloxy group). The siloxy group is reactive with inorganic species and the organofunctional group is reactive or compatible with organic species. Thus, when the silane coupling agent is interposed between the inorganic and organic interfacesAn organic matrix-silane coupling agent-inorganic matrix bonding layer may be formed. Typical silane coupling agents include A151 (vinyltriethoxysilane), A171 (vinyltrimethoxysilane), A172 (vinyltris (. beta. -methoxyethoxy) silane), and the like. Since the adhesion promoter is used in silicone sealants, a silane coupling agent should be used as a main body of the adhesion promoter. However, as described above, since the silicone sealant further contains other organic phases such as a plasticizer and a flame retardant, the silane coupling agent and the titanate coupling agent are used in combination, and the mass ratio of the silane coupling agent to the titanate coupling agent is preferably 1: 1.
In one embodiment of the invention, the isocyanate is an aromatic polyisocyanate and/or an aliphatic polyisocyanate. Isocyanate is commonly used in adhesives for bonding wood, and the conventional wood adhesives have a complex formula, and the raw materials comprise isocyanate, polyol, acidic substances, anionic active agents, hydrophobic solvents and the like so as to ensure the bonding strength. Through research, the applicant finds that the isocyanate is used in the tackifier of the silicone sealant, so that the bonding strength and the water and aging resistance of the silicone sealant can be improved.
In one embodiment of the present invention, the aromatic polyisocyanate is an aromatic diisocyanate selected from at least one of 2, 4-and 2, 6-Toluene Diisocyanate (TDI), 4' -, 2,4' -and 2,2' -diphenylmethane diisocyanate (MDI), 1, 3-and 1, 4-phenylene diisocyanate, 2,3,5, 6-tetramethyl-1, 4-diisocyanatobenzene, naphthalene-1, 5-diisocyanate (NDI), 3' -dimethyl-4, 4' -diisocyanatobiphenyl (TODI).
In one embodiment of the invention, the aliphatic polyisocyanate is an aliphatic diisocyanate selected from the group consisting of 1, 6-Hexamethylene Diisocyanate (HDI), 2-methylpentamethylene-1, 5-diisocyanate, 2, 4-and 2,4, 4-trimethyl-1, 6-hexamethylene diisocyanate (TMDI), 1, 12-dodecamethylene diisocyanate, lysine and lysine ester diisocyanate, cyclohexane-1, 3-diisocyanate, cyclohexane-1, 4-diisocyanate, 1-isocyanato-3, 3, 5-trimethyl-5-isocyanatomethyl-cyclohexane (isophorone diisocyanate or IPDI), perhydro-2, 4' -diphenylmethane diisocyanate and perhydro-4, 4' -diphenylmethane diisocyanate, 1, 4-diisocyanato-2, 2, 6-Trimethylcyclohexane (TMCDI), 1, 3-and 1, 4-bis (isocyanatomethyl) -cyclohexane.
Further, when the isocyanate in the tackifier is a mixture of an aromatic polyisocyanate and an aliphatic polyisocyanate, the performance thereof can be further improved. Preferably, the molar ratio of the two is 1: (1-5).
The embodiment of the invention also relates to a preparation method of the tackifier, which comprises the following steps:
heating the titanate coupling agent and the silane coupling agent to 60-80 ℃, keeping the temperature for 10-30 min, adding isocyanate, and continuing to react for 30-60 min under the condition of introducing protective gas.
The main components of the silicone sealant comprise: alpha, omega-dihydroxy polydimethylsiloxane, filler, flame retardant, plasticizer, tackifier, catalyst, etc. The preparation method mainly comprises the following steps: and adding the prepolymer, the plasticizer and the filler into a stirring kettle, stirring and dispersing under a heating condition, dehydrating, cooling to room temperature, adding the rest of additives, preparing a rubber material, and packaging.
Example 1
Preparation of adhesion promoters
Under the protection of nitrogen, heating the titanate coupling agent and the silane coupling agent to 70 ℃, keeping the temperature for 20min, adding isocyanate, and continuing to react for 40min under the condition of keeping the temperature to obtain the tackifier. The components and parts by weight of each material are shown in table 1.
TABLE 1
Figure BDA0001701850550000061
In table 1, "-" indicates absence.
In comparative example 1-1', isopropyl titanate was used as the tackifier.
In comparative examples 1-2', gamma-aminopropyltriethoxysilane was used as the adhesion promoter.
The tackifier prepared in the above examples 1-1 to 1-7 and comparative examples 1-1 'and 1-2' is used for silicone sealant, and specifically, 100 parts by weight of alpha, omega-dihydroxy polydimethylsiloxane, 15 parts by weight of plasticizer white mineral oil and 1 part by weight of ferric oxide are added into a high-speed reaction kettle for high-speed dispersion, 10 parts by weight of tackifier and 50 parts by weight of white carbon black are added after 20min, and finally, 0.5 part by weight of catalyst dibutyltin diacetate and 20 parts by weight of phosphate flame retardant are added for reaction for 30min to obtain the silicone sealant.
The silicone sealants prepared in the above examples and comparative examples were tested for performance according to industry standards, and the test results are shown in table 2.
TABLE 2
Figure BDA0001701850550000071
As is clear from Table 1, example 1-1 not only had good tensile strength and elongation at break, but also the modulus of the silicone sealant did not decrease and the tack-free time was short.
In examples 1-2, the above properties were hardly changed from those in examples 1-1, except that the specific kinds of the respective raw materials were changed.
The coupling agent content was higher for examples 1-3. The above test parameters were reduced compared to example 1-1. The isocyanate content of examples 1-4 was higher and the tack-free time was also extended similar to that of examples 1-3.
Examples 1-5 and 1-6 use two-component isocyanates and the adhesion promoter performance is further improved.
Examples 1-7, which did not use isocyanate, all had some reduction in performance, but were still superior to comparative examples 1-1 'and 1-2'.
The above description is only for the specific embodiments of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art can easily conceive of the changes or substitutions within the technical scope of the present invention, and all the changes or substitutions should be covered within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the appended claims.

Claims (4)

1. The tackifier applied to the silicone sealant is characterized by being prepared from the following components in parts by weight: 20-50 parts of titanate coupling agent, 20-50 parts of silane coupling agent and 1-10 parts of isocyanate;
the isocyanate is a mixture of 2, 6-toluene diisocyanate and 1, 12-dodecamethylene diisocyanate, and the molar ratio of the two is 1: (1-5);
the titanate coupling agent is isopropyl titanate and/or butyl titanate;
the silane coupling agent is at least one selected from gamma-aminopropyltriethoxysilane, 1, 2-epoxy ethoxy trimethoxysilane, gamma-glycidoxypropyltrimethoxysilane and epoxy cyclohexyl trimethoxysilane.
2. The tackifier of claim 1, wherein the tackifier is prepared from the following components in parts by weight: 30-45 parts of titanate coupling agent, 30-45 parts of silane coupling agent and 5-10 parts of isocyanate.
3. The process for preparing a tackifier according to claim 1 or 2, comprising the steps of:
heating the titanate coupling agent and the silane coupling agent to 60-80 ℃, keeping the temperature for 10-30 min, adding isocyanate, and continuing to react for 30-60 min under the condition of keeping the temperature.
4. The process according to claim 3, wherein the process is carried out under a protective gas atmosphere.
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CN112063345B (en) * 2020-08-18 2022-07-19 湖南创瑾科技有限公司 Nano conductive heat-conducting adhesive and application thereof
CN112608338A (en) * 2020-12-31 2021-04-06 青岛科技大学 Addition type silica gel tackifier and preparation method thereof
CN117363259B (en) * 2023-11-08 2024-03-19 广州雷斯曼新材料科技有限公司 High-adhesive-strength tackifier and preparation method and application thereof

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CN106497501A (en) * 2016-10-26 2017-03-15 马鞍山杰创塑胶科技有限公司 Excellent silane end capped polyurethane modified silicone seal gum of a kind of storage stability and preparation method thereof
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