CN106854219A - A kind of phenyl phosphonyl chloride and meta-xylylene diamine epoxy resin curing agent and preparation method thereof - Google Patents
A kind of phenyl phosphonyl chloride and meta-xylylene diamine epoxy resin curing agent and preparation method thereof Download PDFInfo
- Publication number
- CN106854219A CN106854219A CN201611108187.2A CN201611108187A CN106854219A CN 106854219 A CN106854219 A CN 106854219A CN 201611108187 A CN201611108187 A CN 201611108187A CN 106854219 A CN106854219 A CN 106854219A
- Authority
- CN
- China
- Prior art keywords
- curing agent
- epoxy resin
- phosphonyl chloride
- meta
- phenyl phosphonyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 44
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 37
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 37
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 title claims abstract description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 title claims abstract description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 27
- 125000005499 phosphonyl group Chemical group 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 239000003063 flame retardant Substances 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 239000007787 solid Substances 0.000 claims abstract description 7
- 238000005406 washing Methods 0.000 claims abstract description 6
- 238000001914 filtration Methods 0.000 claims abstract description 5
- 239000011261 inert gas Substances 0.000 claims abstract description 5
- 239000002994 raw material Substances 0.000 claims abstract description 3
- 238000003756 stirring Methods 0.000 claims abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 44
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 13
- 229910052698 phosphorus Inorganic materials 0.000 claims description 13
- 239000011574 phosphorus Substances 0.000 claims description 13
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 238000003786 synthesis reaction Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical class ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 229910052786 argon Inorganic materials 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 239000001307 helium Substances 0.000 claims description 2
- 229910052734 helium Inorganic materials 0.000 claims description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims 5
- 230000000694 effects Effects 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000004593 Epoxy Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 238000013019 agitation Methods 0.000 description 3
- 231100000053 low toxicity Toxicity 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- 235000019504 cigarettes Nutrition 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 238000004100 electronic packaging Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910021389 graphene Inorganic materials 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002341 toxic gas Substances 0.000 description 1
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
- C07F9/4461—Amides thereof the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/448—Amides thereof the amide moiety containing a substituent or a structure which is considered as characteristic of aralkylamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/504—Amines containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Fireproofing Substances (AREA)
Abstract
A kind of phenyl phosphonyl chloride and meta-xylylene diamine epoxy resin curing agent and preparation method thereof.It is related to a kind of curing agent and preparation method thereof, preparing raw material includes：Phenyl phosphonyl chloride and m-xylene diamine, the method for preparing the fire retardant be by phenyl phosphonyl chloride (DCPPO) and m-xylene diamine (MXDA) under inert gas importing stirring reaction certain hour, product obtains white solid through the treatment such as filtering, washing, dry.The compound and epoxy resin have good compatibility, can solidify with epoxy resin be integrated, it is smaller to the Effect on Mechanical Properties of solidfied material, both can effectively improve the fire resistance of epoxy resin again as the curing agent of epoxy resin.Present invention process working condition is simple, product purity and yield is higher, last handling process is easy.
Description
Technical field
The present invention relates to a kind of curing agent and preparation method thereof, more particularly to a kind of phenyl phosphonyl chloride and isophthalic diformazan
Amine epoxy curing agent and preparation method thereof.
Background technology
Epoxy resin is a kind of quite varied high polymer of application, is widely used in casting, coating, adhesive and is combined
In material, excellent mechanical property and electric property are shown.Even so, their inflammability limits it in electronics (print
Circuit board processed, Electronic Packaging etc.) and transport aspect (automobile, train and aircraft) application.Therefore the hair of fire-retardant epoxy resin
Exhibition has a very important role for widening its application field.
At present, many technologies have been widely used in the flame-retarded technology of epoxy resin, and wherein halogenated flame retardant is excellent because of its
Elegant flame retardant effect is widely used in the fire-retardant of epoxy resin, but can be produced in combustion perhaps due to halogen epoxy resin
More poisonous and corrosive gas, produces huge injury to human body incessantly, and also resulting in cannot be reclaimed using the product of halogenated flame retardant
Recycle or thoroughly destroy, cause the environmental pollution and the wasting of resources that cannot be made up.Therefore, the research of halogen-free flame retardants is right
The future development of epoxy resin is significant.
The direction of the fire-retardant research of epoxy resin increasingly tends to non-halogen.How to replace halogen, develop efficiently, low toxicity,
The halogen-free environment-friendly type flame-proof agent of low cigarette and novel flame-retardant epoxide resin material become the study hotspot of domestic and foreign scholars.
Many technologies have been applied to the fire-retardant of epoxy resin.Due to there is the phase with matrix in traditional additive flame retardant
Capacitive is poor, easily migration, and the generation of the mechanical property of matrix can be had a strong impact on, although there are some researches show Graphene, CNT
Its mechanicalness can not be destroyed while fire-retardant Deng as addition type filler, but it is expensive by nanometer additive, limit
It is widely applied.Therefore, it can be reacted with epoxy resin, in being linked into epoxy resin in the form of the chemical bond, to ring
The reaction-type flame-retarding curing agent of smaller or reinforced epoxy the mechanical property of influence of the mechanical property of oxygen tree fat just shows
Big advantage.In addition except the problem that the mechanical property that additive flame retardant can be overcome to bring is reduced, while can be notable
Increase the fire resistance of epoxy resin.
The content of the invention
It is an object of the invention to provide a kind of phenyl phosphonyl chloride and meta-xylylene diamine epoxy resin curing agent and its system
Preparation Method, curing agent contains phosphorus, two kinds of ignition-proof elements of nitrogen, can both participate in the solidification of epoxy resin, meanwhile, with flame retarding efficiency
The features such as high and Halogen, low cigarette, low toxicity, can not only reduce toxic gas and corrosion when additive amount can also reduce its burning
The generation of property gas, meets contemporary environmental requirement.
The purpose of the present invention is achieved through the following technical solutions：
A kind of phenyl phosphonyl chloride and meta-xylylene diamine epoxy resin curing agent, described phosphorus, nitrogen epoxy resin flame retardant curing agent
Preparing raw material includes：Phenyl phosphonyl chloride and m-xylene diamine, the flame retardant curing agent have following structure：
。
A kind of phenyl phosphonyl chloride and meta-xylylene diamine epoxy resin curing agent preparation method, the preparation of the flame retardant curing agent
The step of method one can be completed, by phenyl phosphonyl chloride and m-xylene diamine under inert gas importing stirring reaction, product passes through
Filter, washing, dried process, obtain white solid.
Said process is expressed as with chemical equation：
。
A kind of described phenyl phosphonyl chloride and meta-xylylene diamine epoxy resin curing agent preparation method, in synthesis phosphorus, nitrogen
In flame retardant curing agent, phenyl phosphonyl chloride and m-xylene diamine molar ratio are 1:2.5 to 1:3.5；Solvent for use is N, N '-
The mixture of one kind or its arbitrary proportion in dimethylformamide, dichloromethane, 1,2 dichloroethanes.
A kind of described phenyl phosphonyl chloride and meta-xylylene diamine epoxy resin curing agent preparation method, in synthesis phosphorus, nitrogen
In flame retardant curing agent, reaction temperature is controlled at 20 ~ 40 DEG C；Reaction time is 6 ~ 8h.
A kind of described phenyl phosphonyl chloride and meta-xylylene diamine epoxy resin curing agent preparation method, in synthesis phosphorus, nitrogen
In flame retardant curing agent, inert gas used is the one kind in nitrogen, argon gas or helium.
A kind of described phenyl phosphonyl chloride and meta-xylylene diamine epoxy resin curing agent preparation method, in synthesis phosphorus, nitrogen
In flame retardant curing agent, cleaning solvent is dichloromethane.
A kind of described phenyl phosphonyl chloride and meta-xylylene diamine epoxy resin curing agent preparation method, in synthesis phosphorus, nitrogen
In flame retardant curing agent, drying temperature is 50 ~ 70 DEG C.
Advantages of the present invention is with effect：
1. the present invention provide a kind of phosphorous, nitrogen epoxy curing agent, both can as a kind of curing agent of epoxy resin, and
Tool flame retardant effect, while the good mechanical properties of solidfied material.
2nd, a kind of phosphorous, the nitrogen epoxy curing agent that the present invention is provided, have the advantages that low toxicity, high-efficiency environment friendly, favorably
In sustainable development.
3rd, the preparation method that the present invention is provided is simple, and mild condition, it is easy to control, the product purity of gained is high, post processing
It is convenient.
Specific embodiment
With reference to embodiment, the present invention is described in detail.
Embodiment 1：
Equipped with condenser pipe, nitrogen conduit, DCPPO19.498g is added in the 250ml there-necked flasks of thermometer and magnetic agitation
(0.1mol), 1,2 dichloroethanes 100ml and DMF10ml makees solvent, accurately measures MXDA 40.850g (0.3mol), 1,2 dichloros
Ethane 10ml is added in constant pressure funnel, controls drop rate, completion of dropping in 2h, the nitrogen protection reaction 6h at 20 DEG C
Terminate.Then product dries 12h through filtering, washing in 60 DEG C of vacuum drying chambers, obtains white solid powder.
Embodiment 2：
Equipped with condenser pipe, nitrogen conduit, DCPPO19.498g is added in the 250ml there-necked flasks of thermometer and magnetic agitation
(0.1mol), dichloromethane 110ml makees solvent, accurately measures MXDA 40.850g (0.3mol), controls drop in drop rate, 2h
Add it is complete, at 20 DEG C nitrogen protection reaction 6h terminate.Then product dries through filtering, washing in 60 DEG C of vacuum drying chambers
12h, obtains white solid powder.
Embodiment 3
Equipped with condenser pipe, nitrogen conduit, DCPPO19.498g is added in the 250ml there-necked flasks of thermometer and magnetic agitation
(0.1mol), dichloromethane 110ml makees solvent, accurately measures MXDA 47.659g (0.35mol), drop rate is controlled, in 2h
Completion of dropping, nitrogen protection reaction 6h terminates at 20 DEG C.Then product dries through filtering, washing in 60 DEG C of vacuum drying chambers
12h, obtains white solid powder.
Claims (7)
1. a kind of phenyl phosphonyl chloride and meta-xylylene diamine epoxy resin curing agent, it is characterised in that described phosphorus, azo-cycle oxygen tree
Fat flame retardant curing agent preparing raw material includes：Phenyl phosphonyl chloride and m-xylene diamine, the flame retardant curing agent have following structure：
。
2. a kind of phenyl phosphonyl chloride and meta-xylylene diamine epoxy resin curing agent preparation method, it is characterised in that this is fire-retardant solid
The step of preparation method one of agent can be completed, and by phenyl phosphonyl chloride and m-xylene diamine, stirring is anti-under inert gas importing
Should, product obtains white solid through filtering, washing, dried process；
Said process is expressed as with chemical equation：
。
3. a kind of phenyl phosphonyl chloride according to claim 2 and meta-xylylene diamine epoxy resin curing agent preparation method,
Characterized in that, in synthesis phosphorus, nitrogen flame retardant curing agent, phenyl phosphonyl chloride and m-xylene diamine molar ratio are 1:2.5
To 1:3.5；Solvent for use is N, one kind or its arbitrary proportion in N '-dimethyl formamide, dichloromethane, 1,2 dichloroethanes
Mixture.
4. a kind of phenyl phosphonyl chloride according to claim 2 and meta-xylylene diamine epoxy resin curing agent preparation method,
Characterized in that, in synthesis phosphorus, nitrogen flame retardant curing agent, reaction temperature is controlled at 20 ~ 40 DEG C；Reaction time is 6 ~ 8h.
5. a kind of phenyl phosphonyl chloride according to claim 2 and meta-xylylene diamine epoxy resin curing agent preparation method,
Characterized in that, in synthesis phosphorus, nitrogen flame retardant curing agent, inert gas used is the one kind in nitrogen, argon gas or helium.
6. a kind of phenyl phosphonyl chloride according to claim 2 and meta-xylylene diamine epoxy resin curing agent preparation method,
Characterized in that, in synthesis phosphorus, nitrogen flame retardant curing agent, cleaning solvent is dichloromethane.
7. a kind of phenyl phosphonyl chloride according to claim 2 and meta-xylylene diamine epoxy resin curing agent preparation method,
Characterized in that, in synthesis phosphorus, nitrogen flame retardant curing agent, drying temperature is 50 ~ 70 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611108187.2A CN106854219A (en) | 2016-12-06 | 2016-12-06 | A kind of phenyl phosphonyl chloride and meta-xylylene diamine epoxy resin curing agent and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611108187.2A CN106854219A (en) | 2016-12-06 | 2016-12-06 | A kind of phenyl phosphonyl chloride and meta-xylylene diamine epoxy resin curing agent and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106854219A true CN106854219A (en) | 2017-06-16 |
Family
ID=59127042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201611108187.2A Pending CN106854219A (en) | 2016-12-06 | 2016-12-06 | A kind of phenyl phosphonyl chloride and meta-xylylene diamine epoxy resin curing agent and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106854219A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107474222A (en) * | 2017-07-20 | 2017-12-15 | 沈阳化工大学 | A kind of response type phosphorous epoxy resin flame retardant curing agent and preparation method thereof |
| CN107501606A (en) * | 2017-07-20 | 2017-12-22 | 沈阳化工大学 | A kind of phosphorous, nitrogen Fire Retardant of The Expoxy Resin and preparation method thereof |
| CN111484645A (en) * | 2019-01-25 | 2020-08-04 | 唐雪平 | Novel fireproof heat-preservation polyurethane insulation board for refrigeration house |
| CN111763295A (en) * | 2020-07-02 | 2020-10-13 | 安徽喜宝高分子材料有限公司 | Preparation method of epoxy resin curing agent |
| CN112898927A (en) * | 2021-01-22 | 2021-06-04 | 东莞市派乐玛新材料技术开发有限公司 | Epoxy resin composition and preparation method and application thereof |
| CN113956484A (en) * | 2021-11-17 | 2022-01-21 | 南京工业大学 | Melamine cyanurate derivative covalent triazine frame flame retardant, and preparation method and application thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104945658A (en) * | 2015-06-03 | 2015-09-30 | 南京立汉化学有限公司 | Reaction-type halogen-free flame retardant bis-(p-aminocarboxyphenyl)phenylphosphine oxide and synthetic method thereof |
-
2016
- 2016-12-06 CN CN201611108187.2A patent/CN106854219A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104945658A (en) * | 2015-06-03 | 2015-09-30 | 南京立汉化学有限公司 | Reaction-type halogen-free flame retardant bis-(p-aminocarboxyphenyl)phenylphosphine oxide and synthetic method thereof |
Non-Patent Citations (1)
| Title |
|---|
| ISARA JIRASUTSAKUL ET AL.: "Aromatic phosphorodiamidate curing agent for epoxy resin coating with flame-retarding properties", 《PROGRESS IN ORGANIC COATINGS》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107474222A (en) * | 2017-07-20 | 2017-12-15 | 沈阳化工大学 | A kind of response type phosphorous epoxy resin flame retardant curing agent and preparation method thereof |
| CN107501606A (en) * | 2017-07-20 | 2017-12-22 | 沈阳化工大学 | A kind of phosphorous, nitrogen Fire Retardant of The Expoxy Resin and preparation method thereof |
| CN111484645A (en) * | 2019-01-25 | 2020-08-04 | 唐雪平 | Novel fireproof heat-preservation polyurethane insulation board for refrigeration house |
| CN111763295A (en) * | 2020-07-02 | 2020-10-13 | 安徽喜宝高分子材料有限公司 | Preparation method of epoxy resin curing agent |
| CN112898927A (en) * | 2021-01-22 | 2021-06-04 | 东莞市派乐玛新材料技术开发有限公司 | Epoxy resin composition and preparation method and application thereof |
| CN113956484A (en) * | 2021-11-17 | 2022-01-21 | 南京工业大学 | Melamine cyanurate derivative covalent triazine frame flame retardant, and preparation method and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106854219A (en) | A kind of phenyl phosphonyl chloride and meta-xylylene diamine epoxy resin curing agent and preparation method thereof | |
| CN102391545B (en) | Nitrogen and phosphorus containing flame retardant agent and preparation method thereof as well as application thereof | |
| CN107501606A (en) | A kind of phosphorous, nitrogen Fire Retardant of The Expoxy Resin and preparation method thereof | |
| CN106009040A (en) | Flame retardant containing phosphorus, nitrogen and sulfur and used for epoxy resin and preparation method of flame retardant | |
| CN107474223B (en) | A kind of siliceous nitrogen benzimidazole type epoxy curing agent and preparation method thereof | |
| CN104788647A (en) | Phosphorous-containing epoxy resin amine curing agent and preparation method thereof | |
| CN105111687B (en) | A kind of halogen-free ethoxyline resin antiflaming agent and preparation method thereof | |
| CN102838778A (en) | Preparation method of nitrogen and phosphorus fire retardant, nitrogen and phosphorus fire retardant and application thereof | |
| CN105111688B (en) | A kind of phosphorus, nitrogen expansion type Fire Retardant of The Expoxy Resin and preparation method thereof | |
| JP2014111773A5 (en) | ||
| CN105237957B (en) | A kind of nano flame retardant epoxy resin composite material and preparation method thereof | |
| CN105924674A (en) | Epoxy resin flame retardant containing phosphorus and nitrogen and preparation method of epoxy resin flame retardant | |
| CN104817685A (en) | Reactive epoxy resin flame-retardant curing agent containing phosphorus and nitrogen and preparation method thereof | |
| CN103044708A (en) | High-efficiency N/P flame retardant, as well as preparation method and application thereof | |
| CN103073889B (en) | Flame retardant thermosetting resin and preparation method thereof | |
| CN106750183A (en) | A kind of DOPO modified anhydrides ethoxyline resin antiflaming curing agent and preparation method thereof | |
| CN107474222A (en) | A kind of response type phosphorous epoxy resin flame retardant curing agent and preparation method thereof | |
| CN105384781B (en) | Phenylol bridged rings phosphonitrile additive flame retardant and preparation method thereof | |
| CN105218812A (en) | Insoluble halogen-free flame retardants of a kind of cross-linking type and its preparation method and application | |
| CN105924624B (en) | A kind of phosphorous, nitrogen ethoxyline resin antiflaming curing agent and preparation method thereof | |
| CN103059265A (en) | Halogen-free flame retardant epoxy resin containing naphthalene ring structure and preparation method thereof | |
| CN107090100B (en) | A kind of environmental protection phosphorus-nitrogen one-component expansion type flame retardant and preparation method thereof | |
| CN108084660B (en) | A kind of expansion type fire retarding epoxide resin and preparation method thereof | |
| CN104311818B (en) | A kind of phosphorous, nitrogen aggretion type fire retardant and preparation method thereof | |
| CN107057039A (en) | A kind of phosphorous, nitrogen epoxy resin flame retardant curing agent and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20170616 |
|
| RJ01 | Rejection of invention patent application after publication |