CN115651605A - Ultraviolet-curing organic silicon conductive adhesive and preparation method thereof - Google Patents
Ultraviolet-curing organic silicon conductive adhesive and preparation method thereof Download PDFInfo
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Abstract
The invention relates to the technical field of conductive adhesives, and discloses an ultraviolet curing organic silicon conductive adhesive and a preparation method thereof. The ultraviolet curing organosilicon conductive adhesive comprises the following components in parts by weight: 30-60 parts of acryloyl chloride modified polymethyl siloxane, 10-30 parts of active diluent, 10-40 parts of conductive filler, 2-6 parts of photoinitiator, 0.1-0.2 part of polymerization inhibitor, 1-5 parts of silane coupling agent and 1-5 parts of thixotropic agent. The organic silicon conductive adhesive prepared by utilizing the self-made acryloyl chloride modified polymethylsiloxane has the advantages of high curing speed, strong bonding effect, high toughness and good weather resistance, and meets the bonding requirements of devices in the electronic industry and the like.
Description
Technical Field
The invention relates to the technical field of conductive adhesives, in particular to an ultraviolet curing organic silicon conductive adhesive and a preparation method thereof.
Background
The conductive adhesive is an adhesive with certain conductive performance after being cured or dried. Compared with tin-lead solder, the conductive adhesive has lower use temperature and higher linear resolution, and avoids environmental pollution caused by heavy metal lead, so the conductive adhesive is an ideal choice for replacing lead-tin soldering to realize conductive connection.
The conductive adhesive mainly comprises a resin matrix, a conductive filler, an auxiliary agent and the like. Most of the conductive adhesives used in the current market are filler type. The resin matrix of the filler-type conductive adhesive can be made of various adhesive types, such as epoxy resin, acrylic resin, and silicone resin. Different resin matrixes have advantages and disadvantages, wherein the epoxy resin is rich in formula, but can be cured at high temperature generally, and is not beneficial to application of electronic devices sensitive to heat; acrylic has the advantage of fast curing speed, but has poor weather resistance; the organic silicon resin has better weather resistance and toughness, and has the defect of less reactive groups, which are commonly used for modification by utilizing terminal hydroxyl groups, so that the degree of the resin matrix participating in the curing reaction is not high.
Disclosure of Invention
Aiming at the defects and shortcomings of the prior art, the invention aims to provide the ultraviolet curing organic silicon conductive adhesive which has the advantages of high curing speed, strong bonding effect, high toughness and good weather resistance and can meet the bonding requirement between electronic components.
The invention also aims to provide a preparation method of the ultraviolet curing organosilicon conductive adhesive.
The invention further aims to provide application of the ultraviolet curing organic silicon conductive adhesive.
The purpose of the invention is realized by the following technical scheme:
the ultraviolet curing organic silicon conductive adhesive comprises the following components in parts by weight:
30-60 parts of acryloyl chloride modified polymethyl siloxane;
10-30 parts of an active diluent;
10-40 parts of conductive filler;
2-6 parts of a photoinitiator;
0.1-0.2 part of polymerization inhibitor;
1-5 parts of a silane coupling agent;
1-5 parts of thixotropic agent.
Preferably, the chemical structure general formula of the acryloyl chloride modified polymethylsiloxane is shown as formula I:
the molar content of vinyl in the acryloyl chloride modified polymethyl siloxane is 7-35%.
Preferably, the acryloyl chloride modified polymethylsiloxane is prepared by modifying acryloyl chloride with a random copolymer of two repeating structural units, namely aminopropyl methylsiloxane and dimethylsiloxane, and the random copolymer of the two repeating structural units, namely aminopropyl methylsiloxane and dimethylsiloxane, is shown as a formula II:
preferably, the molar content of the aminopropyl methyl siloxane is 7-35%.
Preferably, the preparation steps of the acryloyl chloride modified polymethylsiloxane are as follows:
(1) Under the protection of nitrogen at 50-70 ℃, adding 50g of octamethylcyclotetrasiloxane, 10-70g of aminopropylmethyldiethoxysilane, 0.1-0.2g of potassium hydroxide powder, 2-15g of water and 0.5-0.7g of dimethyl sulfoxide, heating to 90-100 ℃, balancing for 3-5h, removing water and ethanol generated by reaction for 1-2h, continuing to balance for 5-12h, cooling to 25-50 ℃, adding 0.11-0.21g of acetic acid to neutralize potassium hydroxide, heating to 130-150 ℃, and carrying out reduced pressure distillation for 1-2h to obtain a random copolymer of two repeated structural units of aminopropyl methylsiloxane and dimethylsiloxane;
(2) Mixing 100-200mL of solvent with 50g of random copolymer of two repeated structural units of aminopropyl methyl siloxane and dimethyl siloxane, dripping 4.1-16.9g of acryloyl chloride at 0-25 ℃, reacting for 4-8h, and removing the solvent to obtain the acryloyl chloride modified polymethyl siloxane.
Preferably, the solvent in step (2) is toluene.
Preferably, the reactive diluent is one or a mixture of more of a monofunctional diluent, a bifunctional diluent and a trifunctional diluent;
the conductive filler is one or a mixture of silver powder, silver-plated copper powder and copper powder.
Preferably, the monofunctional diluent is selected from one or a mixture of more than two of methyl acrylate, butyl acrylate, glycidyl acrylate, hydroxyethyl acrylate and hydroxypropyl acrylate; the difunctional diluent is selected from one or a mixture of more than two of diethylene glycol diacrylate phthalate, tripropylene glycol diacrylate phthalate, dipropylene glycol diacrylate, tripropylene glycol diacrylate, diethylene glycol acrylate triethylene glycol diacrylate, neopentyl glycol diacrylate, 1, 6-hexanediol diacrylate and 1, 4-butanediol diacrylate; the trifunctional diluent is one or a mixture of more of trimethylolpropane triacrylate, ethoxylated trimethylolpropane triacrylate, pentaerythritol triacrylate and propoxylated glycerol triacrylate;
the grain size of the silver powder is 10-50nm, the grain size of the silver-plated copper powder is 10-100nm, and the grain size of the copper powder is 10-100nm.
Preferably, the silane coupling agent is one or a mixture of more of 3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, gamma-aminoethylaminopropyltrimethoxysilane, methacryloxypropyltrimethoxysilane, vinyltriethoxysilane, vinyltrimethoxysilane and vinyltris (beta-methoxyethoxy) silane;
the photoinitiator is one selected from 1-hydroxycyclohexyl phenyl ketone, 2,4,6 (trimethylbenzoyl) diphenyl phosphine oxide, 2-methyl-2- (4-morpholinyl) -1- [4- (methylthio) phenyl ] -1-propanone, 2-hydroxy-2-methyl-1-phenyl acetone, thiopropoxy thioxanthone, 2-isopropyl thioxanthone, 6-cumeneferrocenium (II) hexafluorophosphate, diaryliodonium salt and triaryliodonium salt.
Preferably, the polymerization inhibitor is selected from one of hydroquinone, p-benzoquinone, p-hydroxyanisole and 2-tertiary butyl hydroquinone;
the thixotropic agent is selected from one of polyamide wax, fumed silica, organic bentonite, hydrogenated castor oil and metal soap.
A preparation method of a conductive adhesive comprises the following preparation steps:
uniformly mixing acryloyl chloride modified polymethyl siloxane, an active diluent, a polymerization inhibitor, a silane coupling agent and a thixotropic agent, adding a conductive filler, continuously and uniformly mixing, adding a photoinitiator in a light-tight state, uniformly mixing, and carrying out vacuum vibration defoaming to obtain the ultraviolet curing organosilicon conductive adhesive.
The application of the organic silicon conductive adhesive comprises the steps of coating the organic silicon conductive adhesive on the surface of a base material, and crosslinking and curing for 5-30min under the radiation of ultraviolet light with the wavelength of 280-400 nm.
Preferably, the substrate is one of plastic, glass and metal.
Compared with the prior art, the invention has the following advantages and beneficial effects:
(1) The acryloyl chloride modified polymethylsiloxane is prepared by a method of modification after random copolymerization. On the premise of ensuring that the main chain structure of the siloxane is not changed, the content of reactive double bonds is increased, which is beneficial to improving the degree of the organic silicon resin matrix participating in the curing reaction.
(2) According to the invention, the acryloyl chloride modified polymethylsiloxane is added into the conductive adhesive, so that the conductive adhesive has stronger toughness and weather resistance after being cured, after the conductive adhesive is placed in an oven with the shear strength of up to 15MPa and the temperature of 60 ℃ for 15 days, the shear strength and the resistivity of the conductive adhesive are basically unchanged, and the weather resistance is good.
(3) The conductive adhesive of the invention can be cured in 30min under the radiation of ultraviolet light because the resin matrix contains more reactive double bonds, and has higher curing speed.
Drawings
FIG. 1 is the NMR spectrum of acryloyl chloride modified polymethylsiloxane.
Fig. 2 is a schematic diagram of the tensile shear strength of the conductive adhesive.
Detailed Description
The present invention will be described in further detail with reference to specific examples. The following examples are intended to illustrate the invention but should not be construed as limiting it.
Example 1
Adding 40 parts of acryloyl chloride modified polymethyl siloxane, 30 parts of butyl acrylate, 0.2 part of hydroquinone, 4 parts of vinyl tri (beta-methoxyethoxy) silane and 3 parts of fumed silica into a homogenizer, mixing for 30min, then adding 20 parts of copper powder, continuously stirring for 30min, then adding 2 parts of 1-hydroxycyclohexyl phenyl ketone and 1 part of 2,4,6 (trimethylbenzoyl) diphenyl phosphine oxide in a light-shielding state, mixing for 15min at a low speed, and finally performing vacuum vibration defoaming to obtain the ultraviolet curing organosilicon conductive adhesive.
The acryloyl chloride modified polymethylsiloxane is prepared according to the following steps:
the reaction flask was preheated to 50 ℃, evacuated, and then replaced with nitrogen three times. Adding 50g of octamethylcyclotetrasiloxane, 20g of aminopropylmethyldiethoxysilane, 0.1g of potassium hydroxide powder, 4g of water and 0.5g of dimethyl sulfoxide into a reaction bottle, heating to 90 ℃, balancing for 3 hours, vacuumizing to remove water and ethanol generated by the reaction for about 1 hour, and continuing to balance for 6 hours. The temperature was reduced to 50 ℃ and 0.11g of acetic acid was added to neutralize the potassium hydroxide. Then heating to 150 ℃, and distilling under reduced pressure for 1h to obtain transparent viscous liquid, namely a random copolymer of aminopropyl methyl siloxane and dimethyl siloxane with two repeating structural units, wherein the molar content of the aminopropyl methyl siloxane is 13%.
100mL of toluene, 50g of random copolymer of aminopropyl methyl siloxane and dimethyl siloxane which are two kinds of repeated structural units are added into a reaction bottle, 7.4g of acryloyl chloride is dripped at the temperature of 0 ℃, and after 8 hours of reaction, the solvent is removed by decompression and rotary evaporation to obtain the acryloyl chloride modified polymethyl siloxane.
Cleaning the glass slide with ethanol, drying, uniformly coating the conductive adhesive on the glass slide by using a blade coating method, wherein the film thickness is about 100-120um, standing for 10min in a dark place, and then placing at 365nm 100mW/cm 2 Curing for 30min in an ultraviolet curing machine. The conductive adhesive has the shear strength of 8.95MPa and the volume resistivity of 6.2 multiplied by 10 measured by a four-probe method -3 Omega cm. After being placed in a blast oven at 60 ℃ for 15 days, the conductive adhesive of the invention is detected again to have the shear strength of 9.33MPa and the volume resistivity of 6.41 multiplied by 10 -3 Omega cm, the conductive adhesive has good weather resistance.
Example 2
Adding 50 parts of acryloyl chloride modified polymethylsiloxane, 15 parts of hydroxyethyl acrylate, 0.2 part of p-hydroxyanisole, 4 parts of methacryloxypropyltrimethoxysilane and 3 parts of polyamide wax into a homogenizer, mixing for 30min, then adding 25 parts of silver-plated copper powder, continuing stirring for 30min, then adding 2 parts of 1-hydroxycyclohexyl phenyl ketone and 1 part of 2-methyl-2- (4-morpholinyl) -1- [4- (methylthio) phenyl ] -1-acetone in a light-shielding state, mixing for 15min at a low speed, and finally carrying out vacuum vibration defoaming to obtain the ultraviolet curing organosilicon conductive adhesive.
The acryloyl chloride modified polymethylsiloxane is prepared according to the following steps:
the reaction flask was preheated to 50 ℃, evacuated, and then replaced with nitrogen three times. Adding 50g of octamethylcyclotetrasiloxane, 40g of aminopropylmethyldiethoxysilane, 0.15g of potassium hydroxide powder, 8g of water and 0.6g of dimethyl sulfoxide into a reaction bottle, heating to 90 ℃, balancing for 4 hours, vacuumizing to remove water and ethanol for about 2 hours, and continuing to balance for 9 hours. The temperature was reduced to 50 ℃ and 0.16g of acetic acid was added to neutralize the potassium hydroxide. And then heating to 150 ℃, and distilling under reduced pressure for 2 hours to obtain transparent viscous liquid, namely a random copolymer of two repeat structural units of aminopropyl methyl siloxane and dimethyl siloxane, wherein the molar content of the aminopropyl methyl siloxane is 23 percent.
200mL of toluene and 50g of random copolymer of two repeated structural units of aminopropyl methyl siloxane and dimethyl siloxane are added into a reaction bottle, 12.1g of acryloyl chloride is dripped at 0 ℃, and after 8 hours of reaction, the solvent is removed by decompression and rotary evaporation to obtain the acryloyl chloride modified polymethyl siloxane.
Cleaning the glass slide with ethanol, drying, uniformly coating the conductive adhesive on the glass slide by using a blade coating method, wherein the film thickness is about 100-120um, standing for 10min in a dark place, and then placing at 365nm 100mW/cm 2 Curing for 30min in an ultraviolet curing machine. The conductive adhesive of the invention is detected to have the shear strength of 12.61MPa and the volume resistivity of 3.3 multiplied by 10 -3 Ω·cm。
Example 3
Adding 50 parts of acryloyl chloride modified polymethyl siloxane, 10 parts of 1, 4-butanediol diacrylate, 0.2 part of 2-tert-butyl hydroquinone, 4 parts of vinyl triethoxysilane and 3 parts of hydrogenated castor oil into a homogenizer, mixing for 30min, then adding 30 parts of silver powder, continuously stirring for 30min, then adding 3 parts of 6-cumeneferrocene (II) hexafluorophosphate in a light-proof state, mixing for 15min at a low speed, and finally vibrating and defoaming in vacuum to obtain the ultraviolet curing organosilicon conductive adhesive.
The acryloyl chloride modified polymethylsiloxane is prepared according to the following steps:
the reaction flask was preheated to 50 ℃, evacuated and then replaced with nitrogen three times. Adding 50g of octamethylcyclotetrasiloxane, 60g of aminopropylmethyldiethoxysilane, 0.2g of potassium hydroxide powder, 12g of water and 0.7g of dimethyl sulfoxide into a reaction bottle, heating to 90 ℃, balancing for 5 hours, vacuumizing to remove water and ethanol for about 2 hours, and continuing to balance for 12 hours. The temperature was reduced to 50 ℃ and 0.21g of acetic acid was added to neutralize the potassium hydroxide. And then heating to 150 ℃, and distilling under reduced pressure for 2 hours to obtain transparent viscous liquid, namely a random copolymer of two repeat structural units of aminopropyl methyl siloxane and dimethyl siloxane, wherein the molar content of the aminopropyl methyl siloxane is 31 percent.
Adding 200mL of toluene, 50g of random copolymer of aminopropyl methyl siloxane and dimethyl siloxane which are two kinds of repeated structural units into a reaction bottle, dripping 15.4g of acryloyl chloride at 0 ℃, reacting for 8h, decompressing, and carrying out rotary evaporation to remove a solvent to obtain the acryloyl chloride modified polymethyl siloxane.
Cleaning the glass slide with ethanol, drying, uniformly coating the conductive adhesive on the glass slide by using a blade coating method, wherein the film thickness is about 100-120um, standing for 10min in a dark place, and then placing at 365nm 100mW/cm 2 Curing for 30min in an ultraviolet curing machine. The detection shows that the shear strength of the conductive adhesive is 15.72MPa, and the volume resistivity is 2.3 multiplied by 10 -3 Ω·cm。
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (10)
1. The ultraviolet curing organic silicon conductive adhesive is characterized by comprising the following components in parts by weight:
30-60 parts of acryloyl chloride modified polymethyl siloxane;
10-30 parts of an active diluent;
10-40 parts of conductive filler;
2-6 parts of a photoinitiator;
0.1-0.2 part of polymerization inhibitor;
1-5 parts of a silane coupling agent;
1-5 parts of thixotropic agent.
2. The ultraviolet-curable silicone conductive adhesive according to claim 1, wherein the chemical structural general formula of the acryloyl chloride modified polymethylsiloxane is as shown in formula I:
the molar content of vinyl in the acryloyl chloride modified polymethyl siloxane is 7-35%.
3. The ultraviolet-curing organic silicon conductive adhesive as claimed in claim 1 or 2, wherein the acryloyl chloride modified polymethylsiloxane is prepared by modifying acryloyl chloride with a random copolymer of two repeating structural units, namely aminopropyl methylsiloxane and dimethylsiloxane, and the random copolymer of the two repeating structural units, namely aminopropyl methylsiloxane and dimethylsiloxane, is represented by formula II:
4. the ultraviolet-curable silicone conductive adhesive according to claim 3, wherein the acryloyl chloride-modified polymethylsiloxane is prepared by the following specific steps:
(1) Under the protection of nitrogen at 50-70 ℃, adding 50g of octamethylcyclotetrasiloxane, 10-70g of aminopropylmethyldiethoxysilane, 0.1-0.2g of potassium hydroxide powder, 2-15g of water and 0.5-0.7g of dimethyl sulfoxide, heating to 90-100 ℃, balancing for 3-5h, removing water and ethanol generated by reaction for 1-2h, continuing to balance for 5-12h, cooling to 25-50 ℃, adding 0.11-0.21g of acetic acid to neutralize potassium hydroxide, heating to 130-150 ℃, and carrying out reduced pressure distillation for 1-2h to obtain a random copolymer of two repeated structural units of aminopropyl methylsiloxane and dimethylsiloxane;
(2) Mixing 100-200mL of solvent with 50g of random copolymer of two repeated structural units of aminopropyl methyl siloxane and dimethyl siloxane, dripping 4.1-16.9g of acryloyl chloride at 0-25 ℃, reacting for 4-8h, and removing the solvent to obtain the acryloyl chloride modified polymethyl siloxane.
5. The ultraviolet-curable silicone conductive adhesive according to claim 1, wherein the reactive diluent is one or a mixture of a monofunctional diluent, a difunctional diluent and a trifunctional diluent;
the conductive filler is one or a mixture of silver powder, silver-plated copper powder and copper powder.
6. The ultraviolet-curable silicone conductive adhesive according to claim 5, wherein the monofunctional diluent is selected from one or a mixture of methyl acrylate, butyl acrylate, glycidyl acrylate, hydroxyethyl acrylate and hydroxypropyl acrylate; the difunctional group diluent is selected from one or a mixture of more of diethylene glycol diacrylate phthalate, tripropylene glycol diacrylate phthalate, dipropylene glycol diacrylate, tripropylene glycol diacrylate, diethylene glycol diacrylate triethylene glycol diacrylate, neopentyl glycol diacrylate, 1, 6-hexanediol diacrylate and 1, 4-butanediol diacrylate; the trifunctional diluent is one or a mixture of more of trimethylolpropane triacrylate, ethoxylated trimethylolpropane triacrylate, pentaerythritol triacrylate and propoxylated glycerol triacrylate;
the particle size of the silver powder is 10-50nm, the particle size of the silver-plated copper powder is 10-100nm, and the particle size of the copper powder is 10-100nm.
7. The ultraviolet-curable organosilicon conductive adhesive according to claim 1, wherein the silane coupling agent is one or a mixture of 3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, gamma-aminoethylaminopropyltrimethoxysilane, methacryloxypropyltrimethoxysilane, vinyltriethoxysilane, vinyltrimethoxysilane and vinyltris (beta-methoxyethoxy) silane;
the photoinitiator is selected from one of 1-hydroxycyclohexyl phenyl ketone, 2,4,6 (trimethyl benzoyl) diphenyl phosphine oxide, 2-methyl-2- (4-morpholinyl) -1- [4- (methylthio) phenyl ] -1-acetone, 2-hydroxy-2-methyl-1-phenyl acetone, thiopropoxy thioxanthone, 2-isopropyl thioxanthone, 6-isopropylferrocene (II) hexafluorophosphate, diaryl iodonium salt and triaryl iodonium salt.
8. The ultraviolet-curable silicone conductive adhesive according to claim 1, wherein the polymerization inhibitor is one selected from hydroquinone, p-benzoquinone, p-hydroxyanisole, and 2-tert-butylhydroquinone;
the thixotropic agent is one selected from polyamide wax, fumed silica, organic bentonite, hydrogenated castor oil and metal soap.
9. A method for preparing a conductive paste according to any one of claims 1 to 8, comprising the steps of:
uniformly mixing acryloyl chloride modified polymethyl siloxane, a reactive diluent, a polymerization inhibitor, a silane coupling agent and a thixotropic agent, adding a conductive filler, continuously and uniformly mixing, adding a photoinitiator in a light-shading state, uniformly mixing, and carrying out vacuum vibration defoaming to obtain the ultraviolet curing organosilicon conductive adhesive.
10. The application of the organosilicon conductive adhesive according to any one of claims 1 to 8, characterized in that the organosilicon conductive adhesive is coated on the surface of a substrate and is crosslinked and cured for 5 to 30min under the radiation of ultraviolet light with the wavelength of 280nm to 400 nm.
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| CN103732656A (en) * | 2011-08-12 | 2014-04-16 | 莫门蒂夫性能材料股份有限公司 | Siloxane copolymer and solid polymer electrolyte comprising such siloxane copolymers |
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| CN113736087A (en) * | 2021-09-13 | 2021-12-03 | 北京天山新材料技术有限公司 | Organic silicon resin and preparation method thereof, organic silicon conductive adhesive composition and organic silicon conductive adhesive |
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| US6268404B1 (en) * | 1998-08-11 | 2001-07-31 | Th. Goldschmidt Ag | Radiation-curable organosiloxane coating compositions |
| CN103732656A (en) * | 2011-08-12 | 2014-04-16 | 莫门蒂夫性能材料股份有限公司 | Siloxane copolymer and solid polymer electrolyte comprising such siloxane copolymers |
| CN111440321A (en) * | 2020-04-10 | 2020-07-24 | 浙江新安化工集团股份有限公司 | Multifunctional alkoxy-terminated polysiloxane polymer and preparation method thereof |
| CN113736087A (en) * | 2021-09-13 | 2021-12-03 | 北京天山新材料技术有限公司 | Organic silicon resin and preparation method thereof, organic silicon conductive adhesive composition and organic silicon conductive adhesive |
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