CN101993675A - Silane coupling agent modified acrylic pressure sensitive adhesive and preparation method thereof - Google Patents
Silane coupling agent modified acrylic pressure sensitive adhesive and preparation method thereof Download PDFInfo
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- CN101993675A CN101993675A CN 201010533440 CN201010533440A CN101993675A CN 101993675 A CN101993675 A CN 101993675A CN 201010533440 CN201010533440 CN 201010533440 CN 201010533440 A CN201010533440 A CN 201010533440A CN 101993675 A CN101993675 A CN 101993675A
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Abstract
The invention discloses silane coupling agent modified acrylic pressure sensitive adhesive and a preparation method thereof, and belongs to the field of adhesive. The adhesive consists of a acrylic ester soft monomer, a hard monomer and an acrylic functional monomer; and a solvent initiator, an organic solvent, a mercaptan chain transfer agent, a silylene silane coupling agent and a silane coupling agent serving as raw materials are polymerized to form the adhesive through free radicals. The adhesive has high cleanliness and high light transmittance after film forming; the adhesive force on a non-polar plastic base material and a polar metal base material can be improved by adjusting the structure of functional groups in the silylene adhesive; and compared with similar adhesive, the light transmittance of the adhesive is improved by 5 to 10 percent, and the permanent adhesion is more than or equal to 96 hours per 1.5 kilograms and superior to that of most high-grade pressure sensitive adhesive at present markets. The pressure sensitive adhesive can be applied to high-grade home appliance protective films and electronic products such as surface protective films of notebook computers and the like.
Description
Technical field
The present invention relates to adhesive field, especially relate to a kind of silane coupling agent modified acrylic class pressure sensitive adhesive and preparation method thereof.
Background technology
In some high value added product market, harsh to being close in the cleanliness factor of pressure-sensitive adhesive, the requirement that height is held viscous force, rely on conventional oleic series monomer to synthesize merely, be difficult to reach service requirements.Existing silane coupling agent modified acrylic polymerization field, the overwhelming majority relies on the silane coupling agent hydrolysis to form silanol groups, carry out crosslinked being connected on the molecular side chain by the dehydration of silanol groups and carboxylic acid, the adhesive product that this polymerization methods obtains, there is the molecular structure instability, poly-not high problem in the polymkeric substance.
Summary of the invention
Substantially above-mentioned existing in prior technology problem, the embodiment of the invention provides a kind of silane coupling agent modified acrylic class pressure sensitive adhesive and preparation method thereof, can improve the cleanliness factor height of tackiness agent, transmittance height after the film forming, and improve non-polar plastic base material and the splendid sticking power of polarity metal base.
The objective of the invention is to be achieved through the following technical solutions:
The embodiment of the invention provides a kind of silane coupling agent modified acrylic class pressure sensitive adhesive, it is characterized in that, this tackiness agent is a raw material with following each component by mass percentage, comprising:
Esters of acrylic acid soft monomer: 15~35%
Hard monomer: 10~20%
Acrylic acid or the like function monomer: 1~5%
Silylene group silane coupling agent 1.0~5.0%
Solvent-borne type radical initiator: 0.1~2.0%
Organic solvent: 45~60%
Mercaptan type chain transfer agent: 0.05~0.5%
Silane coupling agent: 0.5~2.0%;
Above-mentioned each raw material after carrying out radical polymerization, reactor is obtained this tackiness agent.
The embodiment of the invention further provides a kind of preparation method of silane coupling agent modified acrylic class pressure sensitive adhesive, comprising:
Prescription by above-mentioned silane coupling agent modified acrylic class pressure sensitive adhesive is got each raw material;
With the esters of acrylic acid soft monomer in the raw material, hard monomer, the acrylic acid or the like function monomer, the silylene group silane coupling agent, mercaptan type chain transfer agent mixes with the solvent-borne type radical initiator that accounts for solvent-borne type radical initiator total mass 2/3 and obtains monomer mixture, 1/5~2/5 the mixture of getting described mixture total mass mixes with the organic solvent that occupies machine solvent total mass 1/2 and adds reactor, make and be warming up to 82~85 ℃ in the reactor, reacted 0.5~1 hour, remaining described monomer mixture was added dropwise in 2~4 hours in the reaction system in the reactor, after being added dropwise to complete, remaining solvent-borne type radical initiator and remaining organic solvent are divided in the reaction system that joins in the reactor for three times, make and be warming up to 88~90 ℃ in the reactor, be incubated 2~3 hours, be cooled to 40~50 ℃, add silane coupling agent and stirred 0.5 hour, discharging promptly gets this tackiness agent.
The technical scheme that provides by the embodiment of the invention as can be seen, participate in the radical polymerization of acrylate copolymer molecular backbone chain in the embodiment of the invention by employing allyl silicane coupling agent, silane coupling agent is connected on the molecular backbone chain, make polymer architecture more stable, improve the internal cohesive energy of polymkeric substance greatly, made the viscous force of holding of polymkeric substance be significantly improved compared with similar products; Organosilicon is in the existence of main polymer chain, make the polymkeric substance cleanliness factor obviously improve, transmittance has improved 5~10% than without the modification coupling agent, cooperate the conventional silane coupling agent that is scattered in the system, make molecular structure more stable, the polymkeric substance internal cohesive energy is greatly improved, thereby makes the adhesiveproperties of this tackiness agent be greatly improved.
Embodiment
The invention will be further described below in conjunction with specific embodiment.
Embodiment 1
Present embodiment provides a kind of silane coupling agent modified acrylic class pressure sensitive adhesive, it is characterized in that, this tackiness agent is a raw material with following each component by mass percentage, comprising:
Esters of acrylic acid soft monomer: 15~35%
Hard monomer: 10~20%
Acrylic acid or the like function monomer: 1~5%
Silylene group silane coupling agent 1.0~5.0%
Solvent-borne type radical initiator: 0.1~2.0%
Organic solvent: 45~60%
Mercaptan type chain transfer agent: 0.05~0.5%
Silane coupling agent: 0.5~2.0%;
Esters of acrylic acid soft monomer in the above-mentioned raw materials can adopt: any two kinds mixture in ethyl propenoate, butyl acrylate, ethyl acrylate, the Isooctyl acrylate monomer;
Described hard monomer can adopt: any one in methyl acrylate, methyl methacrylate, Jia Jibingxisuanyizhi, the butyl methacrylate;
Described esters of acrylic acid function monomer can adopt: in methacrylic acid, Hydroxyethyl acrylate, hydroxyethyl methylacrylate, Propylene glycol monoacrylate, Rocryl 410, glycidyl acrylate, glycidyl methacrylate, the isobornyl acrylate any one or several arbitrarily.
The general formula of the allyl silicane coupling agent in the above-mentioned raw materials is: CH
2=CH (CH
2) nSiX
3In this general formula, X is any in chlorine, methoxyl group, oxyethyl group, methoxy ethoxy or the acetoxyl group.The allyl silicane coupling agent specifically can adopt: any one in vinyl trichloro silane, vinyltrimethoxy silane, vinyltriethoxysilane, vinyl trimethoxy Ethoxysilane, vinyl three tert.-butoxy silane, vinyl silane tri-butyl peroxy, vinyltriacetoxy silane, allyltrimethoxysilanis, allyltriethoxysilane, the allyltrichlorosilane etc. or several arbitrarily.
Described solvent-borne type radical initiator can adopt: any one in benzoyl peroxide, the Diisopropyl azodicarboxylate or any two kinds mixture;
Described organic solvent can adopt: any one in ethyl acetate and toluene, the dimethylbenzene.
Described mercaptan type chain transfer agent adopts lauryl mercaptan.
Described silane coupling agent adopts amino silicane coupling agent, amino silicane coupling agent specifically can adopt: any one in γ-An Bingjisanjiayangjiguiwan, γ-An Bingjisanyiyangjiguiwan, aminopropyl methyldiethoxysilane, 3-(2, the 3-epoxy third oxygen) propyl trimethoxy silicane.
The preparation method of this tackiness agent obtains this tackiness agent with each raw material in the above-mentioned prescription after reactor carries out radical polymerization, specifically can be undertaken by following step, comprising:
With the esters of acrylic acid soft monomer in the raw material, hard monomer, the acrylic acid or the like function monomer, the silylene group silane coupling agent, mercaptan type chain transfer agent mixes with the solvent-borne type radical initiator that accounts for solvent-borne type radical initiator total mass 2/3 and obtains monomer mixture, 1/5~2/5 the mixture of getting described mixture total mass mixes with the organic solvent that occupies machine solvent total mass 1/2 and adds reactor, make and be warming up to 82~85 ℃ in the reactor, reacted 0.5~1 hour, remaining described monomer mixture was added dropwise in 2~4 hours in the reaction system in the reactor, after being added dropwise to complete, in remaining solvent-borne type radical initiator and the remaining organic solvent reaction system that average mark joins in the reactor for three times by weight, make and be warming up to 88~90 ℃ in the reactor, be incubated 2~3 hours, be cooled to 40~50 ℃, add silane coupling agent and stirred 0.5 hour, discharging promptly gets this tackiness agent.
During the tackiness agent of present embodiment, by adopting the allyl silicane coupling agent to participate in the radical polymerization of acrylate copolymer molecular backbone chain, open two keys by the silane main chain, participate in radical polymerization and be connected to and carry out modification on the polymer molecule main chain, make polymer architecture more stable, improve the internal cohesive energy of polymkeric substance greatly, made the viscous force of holding of polymkeric substance be significantly improved compared with similar products; Organosilicon is in the existence of main polymer chain, make the polymkeric substance cleanliness factor obviously improve, transmittance has improved 5~10% than without the modification coupling agent, cooperate the conventional silane coupling agent that is scattered in the system, make molecular structure more stable, the polymkeric substance internal cohesive energy is greatly improved, thereby makes the adhesiveproperties of this tackiness agent be greatly improved.
Embodiment 2
Present embodiment provides a kind of silane coupling agent modified acrylic class pressure sensitive adhesive, and this tackiness agent according to the form below proportioning is got each raw material:
The preparation method of above-mentioned tackiness agent is as follows:
With the esters of acrylic acid soft monomer in the raw material, hard monomer, the acrylic acid or the like function monomer, the silylene group silane coupling agent, mercaptan type chain transfer agent mixes with the solvent-borne type radical initiator that accounts for solvent-borne type radical initiator total mass 2/3 and obtains monomer mixture, 1/5~2/5 the mixture of getting described mixture total mass mixes with the organic solvent that occupies machine solvent total mass 1/2 and adds reactor, make and be warming up to 82~85 ℃ in the reactor, reacted 0.5~1 hour, remaining described monomer mixture was added dropwise in 2~4 hours in the reaction system in the reactor, after being added dropwise to complete, in remaining solvent-borne type radical initiator and the remaining organic solvent reaction system that average mark joins in the reactor for three times by weight, make and be warming up to 88~90 ℃ in the reactor, be incubated 2~3 hours, be cooled to 40~50 ℃, add silane coupling agent and stirred 0.5 hour, discharging promptly gets this tackiness agent.
Embodiment 3
Present embodiment provides a kind of silane coupling agent modified acrylic class pressure sensitive adhesive, and this tackiness agent according to the form below proportioning is got each raw material:
Raw material | Weight percent (%) |
Isooctyl acrylate monomer (esters of acrylic acid soft monomer) | 19 |
Ethyl propenoate (esters of acrylic acid soft monomer) | 8 |
Jia Jibingxisuanyizhi or methyl methacrylate (hard monomer) | 13 |
Methacrylic acid (esters of acrylic acid function monomer) | 1.7 |
Isobornyl acrylate (esters of acrylic acid function monomer) | 3 |
Glycidyl acrylate (esters of acrylic acid function monomer) | |
Vinyl three tert.-butoxy silane (allyl silicane coupling agent) | 2.5 |
Diisopropyl azodicarboxylate (solvent-borne type radical initiator) | 1.2 |
Lauryl mercaptan (mercaptan type chain transfer agent) | 0.1 |
Ethyl acetate (organic solvent) | 41 |
Dimethylbenzene (organic solvent) | 9 |
γ-An Bingjisanjiayangjiguiwan (silane coupling agent) | 1.5 |
The preparation method of above-mentioned tackiness agent is substantially the same manner as Example 2, can no longer repeat at this referring to embodiment 2.
Embodiment 3
Raw material | Weight percent (%) |
Butyl acrylate (esters of acrylic acid soft monomer) | 13 |
Isooctyl acrylate monomer (esters of acrylic acid soft monomer) | 18 |
Jia Jibingxisuanyizhi or methyl methacrylate (hard monomer) | 10 |
Isobornyl acrylate (acrylic acid or the like function monomer) | 3 |
Glycidyl acrylate (acrylic acid or the like function monomer) | 2 |
Vinyltriethoxysilane (silylene group silane coupling agent) | 4 |
Benzoyl peroxide (solvent-borne type radical initiator) | 0.6 |
Lauryl mercaptan (mercaptan type chain transfer agent) | 0.1 |
Ethyl acetate (organic solvent) | 36 |
Dimethylbenzene (organic solvent) | 12 |
γ-An Bingjisanjiayangjiguiwan (silane coupling agent) | 1.4 |
The preparation method of above-mentioned tackiness agent is substantially the same manner as Example 2, can no longer repeat at this referring to embodiment 2.Adherent performance test such as following table that the foregoing description 2~4 is made:
Specific performance | Embodiment 2 | Embodiment 3 | Embodiment 4 | Certain foreign brand name pressure sensitive adhesive |
Transmittance | 96% | 99% | 97% | 91% |
Hold viscous force (h/1.5kg) | 104 | 93 | 112 | 79 |
As can be seen from the above table, the tackiness agent cleanliness factor height of the embodiment of the invention, transmittance height after the film forming, regulate the structure of functional group in the silylene group tackiness agent, can improve non-polar plastic base material and the splendid sticking power of polarity metal base, compare with similar tackiness agent, its transmittance improves 5~10%, hold viscous force 〉=96h/1.5kg, be better than the most high-grade pressure sensitive adhesive of existing market.Can be applied on high-grade household electrical appliances protective membrane and the electronic product, as the surface protection film class of notebook computer etc.
In sum, the tackiness agent of the embodiment of the invention participates in the radical polymerization of acrylate copolymer molecular backbone chain by adopting the allyl silicane coupling agent, open two keys by the silane main chain, participate in radical polymerization and be connected to and carry out modification on the polymer molecule main chain, make polymer architecture more stable, improve the internal cohesive energy of polymkeric substance greatly, made the viscous force of holding of polymkeric substance be significantly improved compared with similar products; Organosilicon makes the polymkeric substance cleanliness factor obviously improve in the existence of main polymer chain
The above; only for the preferable embodiment of the present invention, but protection scope of the present invention is not limited thereto, and anyly is familiar with those skilled in the art in the technical scope that the present invention discloses; the variation that can expect easily or replacement all should be encompassed within protection scope of the present invention.Therefore, protection scope of the present invention should be as the criterion with the protection domain of claims.
Claims (10)
1. a silane coupling agent modified acrylic class pressure sensitive adhesive is characterized in that, this tackiness agent is a raw material with following each component by mass percentage, comprising:
Esters of acrylic acid soft monomer: 15~35%
Hard monomer: 10~20%
Acrylic acid or the like function monomer: 1~5%
Silylene group silane coupling agent 1.0~5.0%
Solvent-borne type radical initiator: 0.1~2.0%
Organic solvent: 45~60%
Mercaptan type chain transfer agent: 0.05~0.5%
Silane coupling agent: 0.5~2.0%;
Above-mentioned each raw material after carrying out radical polymerization, reactor is obtained this tackiness agent.
2. silane coupling agent modified acrylic class pressure sensitive adhesive according to claim 1, it is characterized in that described esters of acrylic acid soft monomer adopts: any two kinds mixture in ethyl propenoate, butyl acrylate, ethyl acrylate, the Isooctyl acrylate monomer;
Described hard monomer adopts: any one in methyl acrylate, methyl methacrylate, Jia Jibingxisuanyizhi, the butyl methacrylate;
Described esters of acrylic acid function monomer adopts: in methacrylic acid, Hydroxyethyl acrylate, hydroxyethyl methylacrylate, Propylene glycol monoacrylate, Rocryl 410, glycidyl acrylate, glycidyl methacrylate, the isobornyl acrylate any one or several arbitrarily.
3. silane coupling agent modified acrylic class pressure sensitive adhesive according to claim 1 is characterized in that the general formula of described allyl silicane coupling agent is: CH
2=CH (CH
2) nSiX
3
In the above-mentioned general formula, X is any in chlorine, methoxyl group, oxyethyl group, methoxy ethoxy or the acetoxyl group.
4. according to claim 1 or 3 described silane coupling agent modified acrylic class pressure sensitive adhesives, it is characterized in that described allyl silicane coupling agent adopts: any one in vinyl trichloro silane, vinyltrimethoxy silane, vinyltriethoxysilane, vinyl trimethoxy Ethoxysilane, vinyl three tert.-butoxy silane, vinyl silane tri-butyl peroxy, vinyltriacetoxy silane, allyltrimethoxysilanis, allyltriethoxysilane, the allyltrichlorosilane etc. or several arbitrarily.
5. silane coupling agent modified acrylic class pressure sensitive adhesive according to claim 1 is characterized in that, described solvent-borne type radical initiator adopts: any one in benzoyl peroxide, the Diisopropyl azodicarboxylate or any two kinds;
Described organic solvent adopts: any one in ethyl acetate and toluene, the dimethylbenzene.
6. silane coupling agent modified acrylic class pressure sensitive adhesive according to claim 1 is characterized in that, described mercaptan type chain transfer agent adopts lauryl mercaptan.
7. silane coupling agent modified acrylic class pressure sensitive adhesive according to claim 1 is characterized in that, described silane coupling agent adopts amino silicane coupling agent.
8. silane coupling agent modified acrylic class pressure sensitive adhesive according to claim 7, it is characterized in that, described amino silicane coupling agent adopts: any one in γ-An Bingjisanjiayangjiguiwan, γ-An Bingjisanyiyangjiguiwan, aminopropyl methyldiethoxysilane, 3-(2, the 3-epoxy third oxygen) propyl trimethoxy silicane.
9. silane coupling agent modified acrylic class pressure sensitive adhesive according to claim 1 is characterized in that, describedly above-mentioned each raw material is obtained this tackiness agent comprises after reactor carries out radical polymerization:
With the esters of acrylic acid soft monomer in the raw material, hard monomer, the acrylic acid or the like function monomer, the silylene group silane coupling agent, mercaptan type chain transfer agent mixes with the solvent-borne type radical initiator that accounts for solvent-borne type radical initiator total mass 2/3 and obtains monomer mixture, 1/5~2/5 the mixture of getting described mixture total mass mixes with the organic solvent that occupies machine solvent total mass 1/2 and adds reactor, make and be warming up to 82~85 ℃ in the reactor, reacted 0.5~1 hour, remaining described monomer mixture was added dropwise in 2~4 hours in the reaction system in the reactor, after being added dropwise to complete, remaining solvent-borne type radical initiator and remaining organic solvent are divided in the reaction system that joins in the reactor for three times, make and be warming up to 88~90 ℃ in the reactor, be incubated 2~3 hours, be cooled to 40~50 ℃, add silane coupling agent and stirred 0.5 hour, discharging promptly gets this tackiness agent.
10. the preparation method of a silane coupling agent modified acrylic class pressure sensitive adhesive is characterized in that, comprising:
Each prescription that provides silane coupling agent modified acrylic class pressure sensitive adhesive is got each raw material by claim 1~8;
With the esters of acrylic acid soft monomer in the raw material, hard monomer, the acrylic acid or the like function monomer, the silylene group silane coupling agent, mercaptan type chain transfer agent mixes with the solvent-borne type radical initiator that accounts for solvent-borne type radical initiator total mass 2/3 and obtains monomer mixture, 1/5~2/5 the mixture of getting described mixture total mass mixes with the organic solvent that occupies machine solvent total mass 1/2 and adds reactor, make and be warming up to 82~85 ℃ in the reactor, reacted 0.5~1 hour, remaining described monomer mixture was added dropwise in 2~4 hours in the reaction system in the reactor, after being added dropwise to complete, remaining solvent-borne type radical initiator and remaining organic solvent are divided in the reaction system that joins in the reactor for three times, make and be warming up to 88~90 ℃ in the reactor, be incubated 2~3 hours, be cooled to 40~50 ℃, add silane coupling agent and stirred 0.5 hour, discharging promptly gets this tackiness agent.
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CN114350276A (en) * | 2021-12-31 | 2022-04-15 | 深圳深汕特别合作区昌茂粘胶新材料有限公司 | Substrate-free flame-retardant heat-conducting double-sided adhesive tape and preparation method and application thereof |
CN114350276B (en) * | 2021-12-31 | 2023-09-12 | 深圳深汕特别合作区昌茂粘胶新材料有限公司 | Base material-free flame-retardant heat-conducting double faced adhesive tape, and preparation method and application thereof |
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