CN108250332A - A kind of preparation method and applications of organometallic polymer - Google Patents
A kind of preparation method and applications of organometallic polymer Download PDFInfo
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- CN108250332A CN108250332A CN201810086814.XA CN201810086814A CN108250332A CN 108250332 A CN108250332 A CN 108250332A CN 201810086814 A CN201810086814 A CN 201810086814A CN 108250332 A CN108250332 A CN 108250332A
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- organometallic polymer
- preparation
- epoxy resin
- conductive adhesive
- thermosetting property
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing groups
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
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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
- C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
- C09J9/02—Electrically-conducting adhesives
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Epoxy Resins (AREA)
Abstract
The invention belongs to epoxide-resin glue technical fields, more particularly to a kind of preparation method and applications of organometallic polymer, the preparation method of organometallic polymer in the present invention, easy to operate, prepared organometallic polymer yield is high and purity is pure, and preparing epoxy resin thermosetting property conductive adhesive using the organometallic polymer includes the following raw material：Epoxy resin, toughener, curing agent, organometallic polymer, which easily disperses, storage stability is good and electric conductivity is good.
Description
Technical field
The invention belongs to epoxide-resin glue technical fields, and in particular to a kind of preparation method of organometallic polymer and its
Using.
Background technology
With the rapid development of semiconductor integrated circuit package industry, with having occupied the main body of domestic IC industry
Position, the problem of how selecting electronic package material, seem more important.According to data, most of integrated circuit and various at present
It will miscellaneous bonding material on electronic device.Wherein conducting resinl refers to the special gluing with certain electric conductivity
Agent is mainly obtained by adding in the curing such as curing agent, conductive filler and other additives in organic polymer matrix, and
With with metal similar in electric conductivity.
It is different by the type of conducting particles in conducting resinl, metal system and carbon series conductive glue can be divided into.Metal system conducting resinl has
There is good electric conductivity, but shortcoming is expensive, conductive metal and resin the shortcomings of easily layering and working life are short；Carbon system leads
Electric glue is of low cost, has an absolute price advantage, but there is the drawbacks such as conductive filler dispersion is difficult, electric conductivity is low.
Invention content
In order to overcome shortcoming and defect in the prior art, the purpose of the present invention is to provide a kind of organic metal to gather
The preparation method of object is closed, this method is easy to operate, and the organometallic polymer yield of preparation is high and purity is pure；The present invention's is another
A kind of epoxy resin thermosetting property conductive adhesive and preparation method thereof is designed to provide, the adhesive good dispersion, storage are steady
Fixed and electric conductivity is good, and the preparation method is simple to operation.
The purpose of the present invention is achieved through the following technical solutions：A kind of preparation method of organometallic polymer, feature
It is, includes the following steps：
A, it is vacuumized after mixing 1-5mmol polystyrene and 50-250mL toluene, 30- is stirred under the conditions of 90 DEG C
60min after solution clarification, adds in 1-10mL triethylamines and the bromo- 2- methyl propionyl bromides of 2- of 1-25mL, continues to stir 30-
60min, after solution becomes black, the reaction was continued 10-24 hours, is cooled to room temperature, obtains reaction liquid C, in the reaction liquid C
Add in methanol, precipitate, be filtered, washed, dry after obtain the polystyrene that end group contains bromine；
B, by absolute methanol solution and Na dissolved with 4- dimethylamino pyridines2NH4[Fe(CN)5Dmap] take out after mixing it is true
Sky, in N2It is reacted 10-24 hours after 40 DEG C are warming up under protection, is cooled to room temperature to obtain reaction solution D, after reaction solution D is rotated
It precipitated with dichloromethane and n-hexane mixed solvent, filter, obtain blue iron complex, wherein 4- dimethylamino pyridines after drying
With Na2NH4[Fe(CN)5Dmap] etc. quality；
C, end group described in step a is contained to the blue iron complex first described in the polystyrene of bromine and step b
The mixed solution of alcohol and toluene dissolves, and 72h is stirred at reflux at 80 DEG C, is filtered after reaction, obtains light-blue solid, then use
It is colourless that methanol, which is washed to filtrate, is dried in vacuo at 40 DEG C and for 24 hours, obtains the organometallic polymer that end group contains iron.
The preparation method of organometallic polymer is simple in the present invention, easy to operate, and yield is high.
Wherein, to be added dropwise when adding in the bromo- 2- methyl propionyl bromides of 2- in step a.
By the way that the bromo- 2- methyl propionyl bromides of 2- are added dropwise in step a in the present invention so that reaction is more abundant, does not occur
Team's phenomenon.
Wherein, the volume ratio of methanol and toluene described in step c is 1:1-3.
A kind of application of organometallic polymer prepares epoxy resin thermosetting property conduction using above-mentioned organometallic polymer
Adhesive.
A kind of epoxy resin thermosetting property conductive adhesive, including following raw material：
Organometallic polymer is added in thermosetting property conductive adhesive so that metal divides in adhesive in the present invention
It is good to dissipate property, effectively increases the electric conductivity of adhesive.
Further a kind of epoxy resin thermosetting property conductive adhesive, including following raw material：
Wherein, one or two of the epoxy resin for E44 or bisphenol F epoxy resin.
E44 or bisphenol F epoxy resin softening point are low, and processing forming is good, and the adhesive bonds using its preparation are more preferable,
It is and cost-effective.
Wherein, the curing agent is acid anhydride type curing agent.
Wherein, the curing agent is one or both of trimellitic anhydride or phthalic anhydride.
A kind of preparation method of epoxy resin thermosetting property conductive adhesive, includes the following steps：
(1) epoxy resin of the parts by weight, toughener, organometallic polymer and curing agent are mixed, with 20-25
DEG C/speed of min is heated to 60-70 DEG C, 60-120min is stirred, obtains reactant A；
(2) after reactant A ultrasonic wave being disperseed 60-120min, then deaeration 20-60min obtains epoxy under vacuum conditions
Resin thermoset conductive adhesive.
The method that epoxy resin thermosetting property conductive adhesive is prepared in the present invention is simple, easy to operate, prepares adhesive
Yield is high.
The beneficial effects of the present invention are：The preparation method of organometallic polymer in the present invention, it is easy to operate, prepared
Organometallic polymer yield it is high and purity is pure, prepared epoxy resin thermosetting property conductive adhesive easily disperses, store surely
Qualitative good and electric conductivity is good.
Specific embodiment
For the ease of the understanding of those skilled in the art, with reference to embodiment, the present invention is further illustrated, real
The content that the mode of applying refers to not is limitation of the invention.
Embodiment 1,
A kind of preparation method of organometallic polymer, includes the following steps：
A, it is vacuumized after mixing 1mmol polystyrene and 50mL toluene, stirs 30min under the conditions of 90 DEG C, treat solution
After clarification, 1mL triethylamines and the bromo- 2- methyl propionyl bromides of 2- of 1mL are added in, continues to stir 30min, after solution becomes black, after
Continuous reaction 10 hours, is cooled to room temperature, obtains reaction liquid C, methanol is added in the reaction liquid C, precipitate, be filtered, washed, do
The polystyrene that end group contains bromine is obtained after dry；
B, by absolute methanol solution and Na dissolved with 4- dimethylamino pyridines2NH4[Fe(CN)5Dmap] take out after mixing it is true
Sky, in N2It is reacted 10 hours after 40 DEG C are warming up under protection, is cooled to room temperature to obtain reaction solution D, with two after reaction solution D is rotated
Chloromethanes and n-hexane mixed solvent precipitation, filtering, it is dry after obtain blue iron complex, wherein 4- dimethylamino pyridines with
Na2NH4[Fe(CN)5Dmap] etc. quality；
C, end group described in step a is contained to the blue iron complex first described in the polystyrene of bromine and step b
The mixed solution of alcohol and toluene dissolves, and 72h is stirred at reflux at 80 DEG C, is filtered after reaction, obtains light-blue solid, then use
It is colourless that methanol, which is washed to filtrate, is dried in vacuo at 40 DEG C and for 24 hours, obtains the organometallic polymer that end group contains iron.
Further, to be added dropwise when adding in the bromo- 2- methyl propionyl bromides of 2- in step a.
Further, the volume ratio of methanol and toluene described in step c is 1:1.
A kind of application of organometallic polymer prepares epoxy resin thermosetting property conduction using the organometallic polymer
Adhesive.
A kind of epoxy resin thermosetting property conductive adhesive, including following raw material：
Further, epoxy resin is E44 and bisphenol F epoxy resin weight ratio is 1：1 mixture.
Further, the curing agent is trimellitic anhydride.
A kind of preparation method of epoxy resin thermosetting property conductive adhesive, includes the following steps：
(1) by the epoxy resin of the parts by weight, toughener, organometallic polymer and curing agent mix, with 20 DEG C/
The speed of min is heated to 60 DEG C, stirs 60min, obtains reactant A；
(2) after reactant A ultrasonic wave being disperseed 60min, then deaeration 20min obtains epoxy resin thermosetting under vacuum conditions
Property conductive adhesive.
Embodiment 2,
Embodiment 2 and embodiment 1 difference lies in：The preparation method of the organometallic polymer includes the following steps：
A, it is vacuumized after mixing 5mmol polystyrene and 250mL toluene, stirs 60min under the conditions of 90 DEG C, treat solution
After clarification, 10mL triethylamines and the bromo- 2- methyl propionyl bromides of 2- of 25mL are added in, continues to stir 60min, after solution becomes black,
The reaction was continued 24 hours, is cooled to room temperature, obtains reaction liquid C, and methanol is added in the reaction liquid C, precipitate, be filtered, washed,
The polystyrene that end group contains bromine is obtained after drying；
B, by absolute methanol solution and Na dissolved with 4- dimethylamino pyridines2NH4[Fe(CN)5Dmap] take out after mixing it is true
Sky, in N2It is reacted 24 hours after 40 DEG C are warming up under protection, is cooled to room temperature to obtain reaction solution D, with two after reaction solution D is rotated
Chloromethanes and n-hexane mixed solvent precipitation, filtering, it is dry after obtain blue iron complex, wherein 4- dimethylamino pyridines with
Na2NH4[Fe(CN)5Dmap] etc. quality；
C, end group described in step a is contained to the blue iron complex first described in the polystyrene of bromine and step b
The mixed solution of alcohol and toluene dissolves, and 72h is stirred at reflux at 80 DEG C, is filtered after reaction, obtains light-blue solid, then use
It is colourless that methanol, which is washed to filtrate, is dried in vacuo at 40 DEG C and for 24 hours, obtains the organometallic polymer that end group contains iron.
Embodiment 3,
Embodiment 3 and embodiment 1 difference lies in：A kind of preparation method of organometallic polymer, includes the following steps：
A, it is vacuumized after mixing 3mmol polystyrene and 150mL toluene, stirs 30-60min under the conditions of 90 DEG C, treat
After solution clarification, 5mL triethylamines and the bromo- 2- methyl propionyl bromides of 2- of 15mL are added in, continues to stir 45min, solution becomes black
Afterwards, the reaction was continued 15 hours, is cooled to room temperature, obtains reaction liquid C, and methanol is added in the reaction liquid C, precipitates, filters, washes
Wash, dry after obtain the polystyrene that end group contains bromine；
B, by absolute methanol solution and Na dissolved with 4- dimethylamino pyridines2NH4[Fe(CN)5Dmap] take out after mixing it is true
Sky, in N2It is reacted 15 hours after 40 DEG C are warming up under protection, is cooled to room temperature to obtain reaction solution D, with two after reaction solution D is rotated
Chloromethanes and n-hexane mixed solvent precipitation, filtering, it is dry after obtain blue iron complex, wherein 4- dimethylamino pyridines with
Na2NH4[Fe(CN)5Dmap] etc. quality；
C, end group described in step a is contained to the blue iron complex first described in the polystyrene of bromine and step b
The mixed solution of alcohol and toluene dissolves, and 72h is stirred at reflux at 80 DEG C, is filtered after reaction, obtains light-blue solid, then use
It is colourless that methanol, which is washed to filtrate, is dried in vacuo at 40 DEG C and for 24 hours, obtains the organometallic polymer that end group contains iron.
Further, to be added dropwise when adding in the bromo- 2- methyl propionyl bromides of 2- in step a.
Further, the volume ratio of methanol and toluene described in step c is 1:3.
Embodiment 4
Embodiment 4 and embodiment 1 difference lies in：A kind of epoxy resin thermosetting property conductive adhesive, including following weight
Part raw material：
Embodiment 5
Embodiment 5 and embodiment 1 difference lies in：A kind of epoxy resin thermosetting property conductive adhesive, including following weight
Part raw material：
Embodiment 6
Embodiment 6 and embodiment 1 difference lies in：A kind of epoxy resin thermosetting property conductive adhesive, including following weight
Part raw material：
Embodiment 6
Embodiment 6 and embodiment 1 difference lies in：The curing agent is phthalic anhydride.
Embodiment 7
Embodiment 7 and embodiment 1 difference lies in：The curing agent is trimellitic anhydride and phthalic anhydride weight
Part 1:1 mixture.
Embodiment 8
Embodiment 8 and embodiment 1 difference lies in：The epoxy resin is E44 and the parts by weight of bisphenol F epoxy resin are
1:1 mixture.
Embodiment 9
Embodiment 9 and embodiment 1 difference lies in：A kind of preparation method of epoxy resin thermosetting property conductive adhesive, packet
Include following steps：
(1) epoxy resin of the parts by weight, toughener, organometallic polymer and curing agent are mixed, with 5 DEG C/min
Speed be heated to 0 DEG C, stir 120min, obtain reactant A；
(2) after reactant A ultrasonic wave being disperseed 20min, then deaeration 60min obtains epoxy resin thermosetting under vacuum conditions
Property conductive adhesive.
Comparative example 1
A kind of epoxy resin thermosetting property conductive adhesive, including following raw material：
Further, epoxy resin is E44 and bisphenol F epoxy resin weight ratio is 1：1 mixture.
Further, the curing agent is trimellitic anhydride.
A kind of preparation method of epoxy resin thermosetting property conductive adhesive, includes the following steps：
(1) by the epoxy resin of the parts by weight, toughener, organometallic polymer and curing agent mix, with 20 DEG C/
The speed of min is heated to 60 DEG C, stirs 60min, obtains reactant A；
(2) after reactant A ultrasonic wave being disperseed 60min, then deaeration 20min obtains epoxy resin thermosetting under vacuum conditions
Property conductive adhesive.
Comparative example 2
Difference lies in a kind of epoxy resin thermosetting property conductive adhesives, including following weight with comparative example 1 for comparative example 2
Part raw material：
Highly conductive epoxyn prepared in above example and comparative example is tested, test data is such as
Table 1：
Instrument and equipment
RGT-30 type microcomputer controlled electronic universal testing machines, Shenzhen Rui Geer Co., Ltds；ZC36 meggers:Shanghai
Precision instrumentation Co., Ltd.Test index electrical property
Test index
Electrical property
With reference to national standard, the volume resistivity of casting resin sample is tested.
Mechanical property
By relevant national standard, the bending property of resin composite materials and compressive strength, aluminium/aluminium adhesive strength are tested.
Glue room temperature storage stability is investigated
Uncured composition epoxy resin at 25 DEG C it is closed preserve one week, then observe composition with the presence or absence of be layered or
Deposited phenomenon.
Table 1
As can be drawn from Table 1, the adhesive good dispersion and electric conductivity prepared in the present invention is good.
Above-described embodiment is the preferable implementation of the present invention, but the present invention is not limited to above-mentioned detailed raw material proportioning and tool
Body operating method, without departing from the inventive concept of the premise it is any it is obvious replacement protection scope of the present invention it
It is interior.
Claims (10)
1. a kind of preparation method of organometallic polymer, which is characterized in that include the following steps：
A, it is vacuumized after mixing 1-5mmol polystyrene and 50-250mL toluene, stirs 30-60min under the conditions of 90 DEG C, treat
After solution clarification, 1-10mL triethylamines and the bromo- 2- methyl propionyl bromides of 2- of 1-25mL are added in, continues to stir 30-60min, solution
After becoming black, the reaction was continued 10-24 hours, is cooled to room temperature, obtains reaction liquid C, and methanol is added in the reaction liquid C,
Precipitate, be filtered, washed, dry after obtain the polystyrene that end group contains bromine；
B, by absolute methanol solution and Na dissolved with 4- dimethylamino pyridines2NH4[Fe(CN)5Dmap] mixing after vacuumize,
N2It is reacted 10-24 hours after 40 DEG C are warming up under protection, is cooled to room temperature to obtain reaction solution D, dichloro is used after reaction solution D is rotated
Methane and n-hexane mixed solvent precipitation, filtering, it is dry after obtain blue iron complex, wherein 4- dimethylamino pyridines with
Na2NH4[Fe(CN)5Dmap] etc. quality；
C, by the end group described in step a contain blue iron complex methanol described in the polystyrene of bromine and step b and
The mixed solution dissolving of toluene, 72h is stirred at reflux at 80 DEG C, is filtered after reaction, obtains light-blue solid, again with methanol
Washing to filtrate is colourless, is dried in vacuo at 40 DEG C and for 24 hours, obtains the organometallic polymer that end group contains iron.
2. such as the preparation method of claim 1 organometallic polymer, it is characterised in that：The bromo- 2- methyl-props of 2- are added in step a
To be added dropwise during acylbromide.
3. such as the preparation method of claim 1 organometallic polymer, it is characterised in that：Methanol described in step c and toluene
Volume ratio is 1:1-3.
4. the application of organometallic polymer prepared by the preparation method as described in claim 1-3, which is characterized in that described in utilization
Organometallic polymer prepares epoxy resin thermosetting property conductive adhesive.
A kind of 5. application of organometallic polymer prepared by preparation method as claimed in claim 4, which is characterized in that asphalt mixtures modified by epoxy resin
Fat thermosetting property conductive adhesive, including following raw material：
A kind of 6. application of organometallic polymer prepared by preparation method as claimed in claim 5, which is characterized in that asphalt mixtures modified by epoxy resin
Fat thermosetting property conductive adhesive, including following raw material：
7. the application of organometallic polymer prepared by the preparation method as described in claim 5 or 6 is any, which is characterized in that ring
One or two of the oxygen resin for E44 or bisphenol F epoxy resin.
8. the application of organometallic polymer prepared by the preparation method as described in claim 5 or 6 is any, which is characterized in that institute
Curing agent is stated as acid anhydride type curing agent.
9. the application of organometallic polymer prepared by the preparation method as described in claim 5 or 6 is any, which is characterized in that institute
Curing agent is stated as one or both of trimellitic anhydride or phthalic anhydride.
10. a kind of preparation method of epoxy resin thermosetting property conductive adhesive, which is characterized in that include the following steps：
(1) epoxy resin of the parts by weight, toughener, organometallic polymer and curing agent are mixed, with 20-25 DEG C/min
Speed be heated to 60-70 DEG C, stir 60-120min, obtain reactant A；
(2) after reactant A ultrasonic wave being disperseed 60-120min, then deaeration 20-60min obtains epoxy resin under vacuum conditions
Thermosetting property conductive adhesive.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201810086814.XA CN108250332B (en) | 2018-01-30 | 2018-01-30 | Preparation method and application of organic metal polymer |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810086814.XA CN108250332B (en) | 2018-01-30 | 2018-01-30 | Preparation method and application of organic metal polymer |
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| CN108250332A true CN108250332A (en) | 2018-07-06 |
| CN108250332B CN108250332B (en) | 2020-06-05 |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4005248A (en) * | 1975-06-10 | 1977-01-25 | The Firestone Tire & Rubber Company | Smoke-inhibited polymer compositions |
| CN1616523A (en) * | 2003-09-29 | 2005-05-18 | 三洋电机株式会社 | Organometallic polymer material and process for preparing the same |
| CN102199407A (en) * | 2011-03-18 | 2011-09-28 | 中科院广州化学有限公司 | High-dispersing nanometer silver and high-performance conductive adhesive |
| CN103819904A (en) * | 2012-11-16 | 2014-05-28 | 陶氏环球技术有限责任公司 | Organometallic polymer composition, method for preparing it, and organic light-emitting diode made therefrom |
| CN103865220A (en) * | 2012-11-16 | 2014-06-18 | 陶氏环球技术有限责任公司 | Organometallic polymer composition, method for preparing it, and organic light-emitting diode made therefrom |
-
2018
- 2018-01-30 CN CN201810086814.XA patent/CN108250332B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4005248A (en) * | 1975-06-10 | 1977-01-25 | The Firestone Tire & Rubber Company | Smoke-inhibited polymer compositions |
| CN1616523A (en) * | 2003-09-29 | 2005-05-18 | 三洋电机株式会社 | Organometallic polymer material and process for preparing the same |
| CN102199407A (en) * | 2011-03-18 | 2011-09-28 | 中科院广州化学有限公司 | High-dispersing nanometer silver and high-performance conductive adhesive |
| CN103819904A (en) * | 2012-11-16 | 2014-05-28 | 陶氏环球技术有限责任公司 | Organometallic polymer composition, method for preparing it, and organic light-emitting diode made therefrom |
| CN103865220A (en) * | 2012-11-16 | 2014-06-18 | 陶氏环球技术有限责任公司 | Organometallic polymer composition, method for preparing it, and organic light-emitting diode made therefrom |
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| CN108250332B (en) | 2020-06-05 |
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Address after: Room 101, 201, Building 2, No. 178 Dingxing Road, Tangjiawan Town, High tech Zone, Zhuhai City, Guangdong Province, 519085 Patentee after: Dongguan City Heng Erlang Industrial Co.,Ltd. Address before: 523000 No.10, Lane 5, Shangnan Road, nanzha No.5 Industrial Zone, Humen Town, Dongguan City, Guangdong Province Patentee before: DONGGUAN HENGERLANG INDUSTRIAL CO.,LTD. |