CN107177168A - A kind of hydridization is grafted anti-oxidant flame retardant epoxy material and preparation method thereof - Google Patents
A kind of hydridization is grafted anti-oxidant flame retardant epoxy material and preparation method thereof Download PDFInfo
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- CN107177168A CN107177168A CN201710511426.7A CN201710511426A CN107177168A CN 107177168 A CN107177168 A CN 107177168A CN 201710511426 A CN201710511426 A CN 201710511426A CN 107177168 A CN107177168 A CN 107177168A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/32—Phosphorus-containing compounds
- C08K2003/321—Phosphates
- C08K2003/322—Ammonium phosphate
- C08K2003/323—Ammonium polyphosphate
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- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/38—Boron-containing compounds
- C08K2003/387—Borates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/02—Flame or fire retardant/resistant
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Fireproofing Substances (AREA)
- Organic Insulating Materials (AREA)
Abstract
Anti-oxidant flame retardant epoxy material is grafted the invention discloses a kind of hydridization, it is made up of the raw material of following weight parts：APP 34, 9, the oxide 68 of 10 dihydro, 9 oxa-, 10 phospho hetero phenanthrene 10, vinyltrimethoxy silane 12, azodiisobutyronitrile 0.1 0.2, three-glycidyl chlorinated isocyanurates 23, appropriate dimethylformamide, 3 aminopropyltriethoxywerene werenes 0.8 2, 10 13% hydrochloric acid solution 17 20, methylhexahydrophthalic anhydride 58, epoxy resin E40100 120, di-n-octyl sebacate 34, diisocyanate 0.8 1, DAAM 12, appropriate amount of ethanol, the tert-butyl group is to biphenol 0.4 1, olefin conversion 35, myristic acid soda soap 23, line borate 12.The tert-butyl group that the present invention is added can be effectively to biphenol etc. raising finished-product material antioxygenic property, improve finished product bin stability.
Description
Technical field
The present invention relates to epoxy material technical field, more particularly to a kind of hydridization be grafted anti-oxidant flame retardant epoxy material and its
Preparation method.
Background technology
Polymer inorganic thing composite is caused with its excellent heat endurance, oxidative resistance, mechanical performance and hardness
Extensive concern, macromolecule matrix is to obtain the challenge with excellent properties composite with inorganic alternate incompatibility,
Therefore interfacial interaction between enhancing inorganic matter and macromolecule matrix is so that the dispersiveness for lifting inorganic substances is to solve the problems, such as
Key.Sol-gal process is a kind of conventional method for preparing organic-inorganic hybrid material.It is different in sol-gel process
Silicon burns precursor and collosol and gel condition imparts the great flexibility of sol-gal process.Pass through sol-gel process, inorganic phase
Hydrolysis and condensation that can be through silane be formed, and the interconnection of inorganic phase and organic phase can be realized by chemical bond.Inorganic matter
The fire resistance and heat endurance of polymer can be lifted, and organic group can be lifted between inorganic substances and macromolecule matrix
Interfacial interaction power, so as to improve scattered situation of the inorganic substances in macromolecule matrix；
Epoxide resin material is wide due to its excellent mechanical strength and Firmware, good solvent resistance and excellent cohesive
It is general be used as coating, adhesive, laminate, semiconductor sealing material and other functional materials however epoxy resin and epoxy third refine acid
The anti-flammability of resin limits their application.Containing the light base for being available for reaction on epoxy main chains, and these light bases can be
The flame-retardant modified basic site that chemical reaction is provided；
In phosphorus flame retardant, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide is due to excellent in epoxy resin-base
Different fire-retardant performance is got the attention.But miscellaneous -10- phospho hetero phenanthrenes -10- the oxides of 9,10- dihydro-9-oxies and its derivative
It is solid-state under normal circumstances, this causes itself and macromolecule matrix poor compatibility, so as to cause to ooze out during bad dispersibility, use
The shortcomings of with other aspect performances of reduction macromolecule matrix；In order to solve the above problems, one kind based on 9,10- dihydro-9-oxies it is miscellaneous-
10- phospho hetero phenanthrene -10- oxides and can have with macromolecule matrix excellent compatibility liquid flame retardant be designed exploitation piece be applied to
In epoxy resin；
High polymer material is widely used in the life of people, and such as plastics, rubber, fiber, coating and adhesive are each in the world
Ground is in great demand.Although high polymer material has many advantages relative to traditional material, its combustion property makes it some special
The application in field is restricted, therefore it is the inevitable approach for extending its application that flame retardant treatment is carried out to high polymer material；
Phosphorus is added to fire-retardant in polymeric matrix have many good qualities as ignition-proof element.In higher flame retarding efficiency, combustion process
The menace less to ecological environment turns into phosphorus flame retardant to be most hopeful to replace during less flue gas release and use
The fire retardant of halogenated flame retardant status in industrialized production.Usual inorganic silicon as additive be added in macromolecule matrix with
Lift the flame retarding efficiency of material.In the thermal degradation process of composite, these silicon matters can be with macromolecule matrix phase interaction
With, and silicon due to relatively low surface can and migrated to polymer surfaces, so as to form the firm layer of charcoal that surface is rich in silicon.Work as silicon
Combined with phosphorus when being added in macromolecule matrix, composite due to phosphorus silicon cooperative flame retardant effect and show higher
Flame retarding efficiency.Therefore the fire-retardant application study of the organic-inorganic hybrid material based on phosphorus and silicon is carried out, by MOLECULE DESIGN system
The organic inorganic hybridization fire retardant of standby phosphorous and silicon, and pass through various technologies such as expansion type flame-retarding technology, sol-gel technique
The flame retarding efficiency for lifting phosphorus silicon fire retardant with nanometer technology is significant.
The content of the invention
The object of the invention is exactly to be grafted anti-oxidant flame retardant epoxy material there is provided a kind of hydridization to make up the defect of prior art
Material and preparation method thereof.
The present invention is achieved by the following technical solutions：
A kind of hydridization is grafted anti-oxidant flame retardant epoxy material, and it is made up of the raw material of following weight parts：
APP 3-4,9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide 6-8, vinyltrimethoxy silane 1-
2nd, azodiisobutyronitrile 0.1-0.2, three-glycidyl chlorinated isocyanurates 2-3, appropriate dimethylformamide, the second of 3- aminopropyls three
TMOS 0.8-2,10-13% hydrochloric acid solution 17-20, methylhexahydrophthalic anhydride 5-8, epoxy resin E40100-
120th, di-n-octyl sebacate 3-4, diisocyanate 0.8-1, DAAM 1-2, appropriate amount of ethanol, the tert-butyl group are to biphenol
0.4-1, olefin conversion 3-5, myristic acid soda soap 2-3, line borate 1-2.
A kind of described hydridization is grafted the preparation method of anti-oxidant flame retardant epoxy material, comprises the following steps：
（1）Above-mentioned APP, line borate are mixed, in the deionized water for being added to 25-30 times of compound weight, stirring is equal
It is even, add above-mentioned DAAM, insulated and stirred 4-7 minutes at 50-60 DEG C, acid amides dispersion liquid；
（2）Above-mentioned azodiisobutyronitrile is added in 20-30 times of dimethylformamide of its weight, stirs, obtains initiator
Solution；
（3）Above-mentioned 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, vinyltrimethoxy silane are mixed, added
Into the dimethylformamide of 10-14 times of compound weight, nitrogen is passed through, rise temperature is 76-80 DEG C, and above-mentioned initiator is added dropwise
Solution, insulated and stirred 20-25 hours, is distilled off dimethylformamide, obtains silane oxide；
（4）Above-mentioned three-glycidyl chlorinated isocyanurates is added in the dimethylformamide of 20-30 times of its weight, nitrogen is passed through
Gas, rise temperature is 50-60 DEG C, insulated and stirred 10-11 after above-mentioned APTES, completion of dropping is added dropwise small
When, dimethylformamide is distilled off, silane glyceride is obtained；
（5）In the absolute ethyl alcohol that the above-mentioned tert-butyl group is added to 18-20 times of its weight to biphenol, stir, add above-mentioned
Silane oxide, insulated and stirred 3-5 minutes at 70-75 DEG C, adds above-mentioned myristic acid soda soap, stirs to normal temperature, obtain silane
Oxidate dispersion solution；
（6）Above-mentioned diisocyanate, silane glyceride are mixed, in the absolute ethyl alcohol for being added to 40-50 times of compound weight, plus
Enter above-mentioned silane oxide dispersion liquid, stir, be passed through nitrogen, add above-mentioned 10-13% hydrochloric acid solution, 10- is stirred at room temperature
12 hours, powder is distilled to obtain, powder is washed 2-3 times with absolute ethyl alcohol, dried 1-2 hours at 50-60 DEG C of vacuum, obtain hydridization fire-retardant
Agent；
（7）Above-mentioned Hybrid fire retardant is added in acid amides dispersion liquid, stirred, above-mentioned olefin conversion is added, at 60-65 DEG C
Insulated and stirred 10-20 minutes, obtains fire-retardant dispersion liquid；
（8）Above-mentioned fire-retardant dispersion liquid is mixed with above-mentioned epoxy resin E40, rise temperature is 100-105 DEG C, insulated and stirred 20-
30 minutes, mix, stir with remaining each raw material, be sent in polytetrafluoroethylene (PTFE) template, rise temperature is 110-120 DEG C,
Insulation 120-130 minutes, rise temperature is 140-150 DEG C, is incubated 1-2 hours, is cooled to room temperature, is stripped, produces.
It is an advantage of the invention that：
P elements in the silane oxide structure of the present invention departing from original structure and form other new under the high temperature conditions
Type phosphorus structure, the New Phosphorus structure can react with epoxy matrix, can play a part of hydroperoxyl radical capture in the gas phase, and
The effect of this capture free radical can suppress the burning of material, degrade under cryogenic and form lewis acid, and these are sour
The carbonization of epoxy resin can be promoted to degrade, more volatile small molecules, such as water, alkane chain so that polymer are formed
Surface forms firm protection type layer of charcoal, and these layer of charcoal are due to the crosslinked action of organophosphor and the humidification of silicon, Neng Gouqi
To the effect of more preferable heat-insulated oxygen barrier, while during layer of charcoal is formed, silane glyceride structure is degraded and discharged non-ignitable
Property gas, non-flammable gases, which can assist in, to form intumescent layer of charcoal, and intumescent layer of charcoal can play heat-insulated oxygen barrier, prevents flammable
Property gaseous volatilization effect, the present invention mixes Hybrid fire retardant with epoxy resin, because the catalytic crosslinking of phosphorus, silicon are burned
In journey to polymer layer of charcoal table and be enriched with and serve certain layer of charcoal humidification, the foamed char of nitrogen interact so that
The burning breeze of composite occurs in that a certain degree of expansion and the breeze relative to pure epoxy resin has necessarily firm
Property, fine and close and complete layer of charcoal is shown, good fire retardant performance is served；
The tert-butyl group that the present invention is added to biphenol etc. can be effectively raising finished-product material antioxygenic property, improve finished product
Bin stability.
Embodiment
A kind of hydridization is grafted anti-oxidant flame retardant epoxy material, and it is made up of the raw material of following weight parts：
The dihydro oxa- phospho hetero phenanthrene oxide 6 of APP 3,9,10, vinyltrimethoxy silane 1, azodiisobutyronitrile 0.1,
Three-glycidyl chlorinated isocyanurates 2, appropriate dimethylformamide, the hydrochloric acid solution of 3 aminopropyltriethoxywerene werenes 0.8,10%
17th, methylhexahydrophthalic anhydride 5, epoxy resin E40100, di-n-octyl sebacate 3, diisocyanate 0.8, diacetone third
Acrylamide 1, appropriate amount of ethanol, the tert-butyl group are to biphenol 0.4, olefin conversion 3, myristic acid soda soap 2, line borate 1.
A kind of described hydridization is grafted the preparation method of anti-oxidant flame retardant epoxy material, comprises the following steps：
（1）Above-mentioned APP, line borate are mixed, in the deionized water for being added to 25 times of compound weight, stirred, plus
Enter above-mentioned DAAM, insulated and stirred 4 minutes at 50 DEG C, acid amides dispersion liquid；
（2）Above-mentioned azodiisobutyronitrile is added in 20 times of dimethylformamides of its weight, stirs, obtains initiator molten
Liquid；
（3）Above-mentioned 9,10 dihydro oxa- phospho hetero phenanthrene oxides, vinyltrimethoxy silane are mixed, compound weight is added to
In 10 times of dimethylformamide, nitrogen is passed through, rise temperature is 76 DEG C, above-mentioned initiator solution is added dropwise, insulated and stirred 20 is small
When, dimethylformamide is distilled off, silane oxide is obtained；
（4）In the dimethylformamide that above-mentioned three-glycidyl chlorinated isocyanurates is added to 20 times of its weight, nitrogen is passed through, is risen
High-temperature is 50 DEG C, and insulated and stirred 10 hours after above-mentioned 3 aminopropyltriethoxywerene werene, completion of dropping are added dropwise, are distilled off
Dimethylformamide, obtains silane glyceride；
（5）In the absolute ethyl alcohol that the above-mentioned tert-butyl group is added to 18 times of its weight to biphenol, stir, add above-mentioned silane
Oxide, insulated and stirred 3 minutes at 70 DEG C add above-mentioned myristic acid soda soap, stir to normal temperature, obtain silane oxide and disperse
Liquid；
（6）Above-mentioned diisocyanate, silane glyceride are mixed, in the absolute ethyl alcohol for being added to 40 times of compound weight, added
Above-mentioned silane oxide dispersion liquid, stirs, and is passed through nitrogen, adds above-mentioned 10% hydrochloric acid solution, is stirred at room temperature 10 hours,
Powder is distilled to obtain, powder is washed 2 times with absolute ethyl alcohol, is dried 1 hour at 50 DEG C of vacuum, obtains Hybrid fire retardant；
（7）Above-mentioned Hybrid fire retardant is added in acid amides dispersion liquid, stirred, above-mentioned olefin conversion is added, protected at 60 DEG C
Temperature stirring 10 minutes, obtains fire-retardant dispersion liquid；
（8）Above-mentioned fire-retardant dispersion liquid is mixed with above-mentioned epoxy resin E40, rise temperature is 100 DEG C, insulated and stirred 20 minutes,
Mix, stir with remaining each raw material, be sent in polytetrafluoroethylene (PTFE) template, rise temperature is 110 DEG C, is incubated 120 minutes,
It is 140 DEG C to raise temperature, is incubated 1 hour, is cooled to room temperature, is stripped, produces.
Claims (2)
1. a kind of hydridization is grafted anti-oxidant flame retardant epoxy material, it is characterised in that it is made up of the raw material of following weight parts：
APP 3-4,9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide 6-8, vinyltrimethoxy silane 1-
2nd, azodiisobutyronitrile 0.1-0.2, three-glycidyl chlorinated isocyanurates 2-3, appropriate dimethylformamide, the second of 3- aminopropyls three
TMOS 0.8-2,10-13% hydrochloric acid solution 17-20, methylhexahydrophthalic anhydride 5-8, epoxy resin E40100-
120th, di-n-octyl sebacate 3-4, diisocyanate 0.8-1, DAAM 1-2, appropriate amount of ethanol, the tert-butyl group are to biphenol
0.4-1, olefin conversion 3-5, myristic acid soda soap 2-3, line borate 1-2.
2. a kind of hydridization as claimed in claim 1 is grafted the preparation method of anti-oxidant flame retardant epoxy material, it is characterised in that bag
Include following steps：
（1）Above-mentioned APP, line borate are mixed, in the deionized water for being added to 25-30 times of compound weight, stirring is equal
It is even, add above-mentioned DAAM, insulated and stirred 4-7 minutes at 50-60 DEG C, acid amides dispersion liquid；
（2）Above-mentioned azodiisobutyronitrile is added in 20-30 times of dimethylformamide of its weight, stirs, obtains initiator
Solution；
（3）Above-mentioned 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, vinyltrimethoxy silane are mixed, added
Into the dimethylformamide of 10-14 times of compound weight, nitrogen is passed through, rise temperature is 76-80 DEG C, and above-mentioned initiator is added dropwise
Solution, insulated and stirred 20-25 hours, is distilled off dimethylformamide, obtains silane oxide；
（4）Above-mentioned three-glycidyl chlorinated isocyanurates is added in the dimethylformamide of 20-30 times of its weight, nitrogen is passed through
Gas, rise temperature is 50-60 DEG C, insulated and stirred 10-11 after above-mentioned APTES, completion of dropping is added dropwise small
When, dimethylformamide is distilled off, silane glyceride is obtained；
（5）In the absolute ethyl alcohol that the above-mentioned tert-butyl group is added to 18-20 times of its weight to biphenol, stir, add above-mentioned
Silane oxide, insulated and stirred 3-5 minutes at 70-75 DEG C, adds above-mentioned myristic acid soda soap, stirs to normal temperature, obtain silane
Oxidate dispersion solution；
（6）Above-mentioned diisocyanate, silane glyceride are mixed, in the absolute ethyl alcohol for being added to 40-50 times of compound weight, plus
Enter above-mentioned silane oxide dispersion liquid, stir, be passed through nitrogen, add above-mentioned 10-13% hydrochloric acid solution, 10- is stirred at room temperature
12 hours, powder is distilled to obtain, powder is washed 2-3 times with absolute ethyl alcohol, dried 1-2 hours at 50-60 DEG C of vacuum, obtain hydridization fire-retardant
Agent；
（7）Above-mentioned Hybrid fire retardant is added in acid amides dispersion liquid, stirred, above-mentioned olefin conversion is added, at 60-65 DEG C
Insulated and stirred 10-20 minutes, obtains fire-retardant dispersion liquid；
（8）Above-mentioned fire-retardant dispersion liquid is mixed with above-mentioned epoxy resin E40, rise temperature is 100-105 DEG C, insulated and stirred 20-
30 minutes, mix, stir with remaining each raw material, be sent in polytetrafluoroethylene (PTFE) template, rise temperature is 110-120 DEG C,
Insulation 120-130 minutes, rise temperature is 140-150 DEG C, is incubated 1-2 hours, is cooled to room temperature, is stripped, produces.
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Cited By (4)
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|---|---|---|---|---|
| CN109735157A (en) * | 2018-12-24 | 2019-05-10 | 东南大学 | A kind of fireproof flame-retardant coating silicon nitrogen phosphorus efficiency halogen-free flame retardants and its preparation method and application |
| CN109824868A (en) * | 2019-01-23 | 2019-05-31 | 盐城艾肯科技有限公司 | A kind of preparation method and application with DOPO structure photosensitive resin |
| CN113024980A (en) * | 2021-05-06 | 2021-06-25 | 海梦城文化科技股份有限公司 | Acrylic material and preparation method thereof |
| CN113045800A (en) * | 2021-04-06 | 2021-06-29 | 什邡市太丰新型阻燃剂有限责任公司 | Novel flame retardant based on APP and DOPO and preparation method thereof |
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| CN106832778A (en) * | 2017-02-13 | 2017-06-13 | 广州仑利奇合成树脂有限公司 | A kind of halogen-free flameproof epoxy systems and preparation method thereof |
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| CN106008919A (en) * | 2016-06-12 | 2016-10-12 | 福州大学 | Phosphorus-containing flame-retardant epoxy resin having undergone hydrophobic modification by silane, and preparation method thereof |
| CN106832778A (en) * | 2017-02-13 | 2017-06-13 | 广州仑利奇合成树脂有限公司 | A kind of halogen-free flameproof epoxy systems and preparation method thereof |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109735157A (en) * | 2018-12-24 | 2019-05-10 | 东南大学 | A kind of fireproof flame-retardant coating silicon nitrogen phosphorus efficiency halogen-free flame retardants and its preparation method and application |
| CN109735157B (en) * | 2018-12-24 | 2020-11-03 | 东南大学 | Silicon-nitrogen-phosphorus efficient halogen-free flame retardant for fireproof flame-retardant coating, and preparation method and application thereof |
| CN109824868A (en) * | 2019-01-23 | 2019-05-31 | 盐城艾肯科技有限公司 | A kind of preparation method and application with DOPO structure photosensitive resin |
| CN109824868B (en) * | 2019-01-23 | 2021-01-29 | 盐城艾肯科技有限公司 | Preparation method and application of photosensitive resin with DOPO structure |
| CN113045800A (en) * | 2021-04-06 | 2021-06-29 | 什邡市太丰新型阻燃剂有限责任公司 | Novel flame retardant based on APP and DOPO and preparation method thereof |
| CN113024980A (en) * | 2021-05-06 | 2021-06-25 | 海梦城文化科技股份有限公司 | Acrylic material and preparation method thereof |
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