CN102061011A - Intercalator and preparation method thereof - Google Patents
Intercalator and preparation method thereof Download PDFInfo
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- CN102061011A CN102061011A CN 201010593288 CN201010593288A CN102061011A CN 102061011 A CN102061011 A CN 102061011A CN 201010593288 CN201010593288 CN 201010593288 CN 201010593288 A CN201010593288 A CN 201010593288A CN 102061011 A CN102061011 A CN 102061011A
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Abstract
The invention relates to a preparation method of an intercalator. The preparation method is characterized by comprising the following steps of: adding an amine compound into a reactor, dripping formaldehyde at a stirring speed of 20-500 turns/min and a controlled temperature of 25-45 DEG C and finishing the dripping within 0.5-4 h; continuously reacting for 0.5-2 h after the dripping is finished; adding a phenolic compound into the reactor, increasing the temperature to 50-60 DEG C and reacting for 0.5-2 h; increasing the temperature to 80-100 DEG C and reacting for 2-6 h; and increasing the temperature to 120-150 DEG C and reacting for 2-6 h to evaporate water content and obtain the intercalator. Compared with a traditional intercalator, the intercalator structure provided by the invention contains phenyl or phenyl sulfide for intercalating montmorillonite layers to not only increase the distance among the montmorillonite layers and the possibility for epoxy and a curing agent to enter the interlamination, but also effectively promote the reaction activity of the epoxy groups and the amino of the interlamination and preferentially carry out the interlamination reaction to the whole system so as to stimulate the interlamination stripping of the montmorillonite.
Description
Technical field
The present invention relates to a kind of intercalator, especially a kind of intercalator of preparing organic montmorillonoid and preparation method thereof that is used to belongs to chemical field.
Background technology
Resins, epoxy is the thermosetting polymer synthetic materials that a class has excellent properties, is widely used in fields such as matrix material, electrical apparatus insulation material, coating and sizing agent with its excellent mechanical property, electric property and adhesiveproperties.Conventional epoxies curing system fragility is bigger, and is shock-resistant poor with resistance to fatigue, limited its Application Areas to a great extent.In recent years, development along with wind energy and big aircraft industries, large-scale composite materials such as megawatt level wind power generation blade and fuselage are had higher requirement for the mechanical property of material, Resins, epoxy conduct crucial starting material are wherein also had higher requirement to intensity, toughness and fatigue performance after its curing.
Both at home and abroad researcher has carried out a large amount of research to Resins, epoxy toughness reinforcing.The Resins, epoxy and the solidifying agent kind of practical application now increase greatly, can obtain toughness cured product preferably, but higher cost have limited its Application Areas.General method of modifying but can reduce other physicalies in the toughness that improves epoxy resin cured product, shock resistance.
Resins, epoxy-Nano composite material of montmorillonite is a kind ofly to add the polynite that organic intercalation agent handled carry out thorough mixing in epoxy-resin systems, and the polynite that obtains of curing reaction is with nanoscale dispersive material then.The Epoxy Resin nano composite material of preparation gained when not influencing other physicalies, but can improve physicalies such as toughness behind the epoxy resin cure, shock resistance greatly.
The preparation of Resins, epoxy-montmorillonite composite material is a laminate structure of utilizing polynite, will have the inorganic metal ion (Na that cationic organic intercalation agent replaces the polynite surface
+, Ca
2+, Mg
2+), change the polarity on montmorillonite layer surface, reduce its surface energy, and the support large interlamellar spacing from, help entering of Resins, epoxy and solidifying agent molecule, heat effect when utilizing curing reaction is destroyed the laminate structure of polynite, the laminate structure of the nanoscale that formation is peeled off, be dispersed in the polymeric matrix, thereby form nanoscale compound of Resins, epoxy and polynite, reach the ideal toughening effect.In this process, the selection of the selection of organic intercalation agent and intercalation method is very crucial, in relevant patent, have much for this content aspect two to have proposed claim, as: publication number is " a kind of Antiflowing epoxy resin/mentmorillonite compound and preparation method thereof " of " CN1250790A ".CH is adopted in this invention
3(CH
2)
nNR
3 +Be intercalator, carry out ion-exchange in the aqueous solution, obtained organically-modified polynite, selecting DDM for use is solidifying agent, has finally obtained intercal type polynite/epoxy resin composite material.
Publication number be " CN1250064A's " " a kind of preparation method of Epoxy Resin intercalation composite material ", CH is adopted in this invention
3(CH
2)
11NR
3 +Be intercalator, carry out ion-exchange in the aqueous solution, obtained organically-modified polynite, selecting dimethyl benzyl amine for use is solidifying agent, has obtained intercal type polynite/epoxy resin composite material.
Publication number be " CN1354198A's " " a kind of Epoxy Resin nano composite material and preparation method thereof ", it is intercalator that hexanediamine, n-octyl amine, n-Decylamine, amino dodecane, dihydroxy ethyl methyl octadecyl bromination amine are adopted in this invention, in the aqueous solution, carry out ion-exchange, obtained organically-modified polynite, selecting low molecular polyamides or tetrahydrophthalic anhydride for use is solidifying agent, has obtained intercal type polynite/epoxy resin composite material.
Publication number be " CN1978525A's " " a kind of epoxy/laminated nm-silicate composite material and preparation method thereof ", CH is adopted in this invention
3(CH
2)
nNH
2Be intercalator, in the aqueous solution, carry out ion-exchange, obtained organically-modified polynite.
Publication number be " US5554670's " " Method of preparing layered silicate-epoxy nancomposites ", this invention has adopted organic ammonium salt as properties-correcting agent, contain hydroxyl, epoxy group(ing) or carboxyl on the organic main chain that links to each other with ammonium salt, make it can participate in crosslinking reaction, finally make polynite can be connected in the cross-linked network strongthener performance by chemical bond-linking.
Publication number be " US5801216's " " Flexible resin-clay composite; method ofpreparation and use ", this invention has adopted ammonium salt that main chain contains 3～22 carbon atoms as properties-correcting agent, and the ion exchange process of polynite carries out in 1: 1 ethanol/water solution.
Publication number be " US6251980's " " Nan composites formed by onium ion-intercalatedclay and rigid anhydride-cured epoxy resins ", this invention adopts salt as intercalator, salt such as N, P, O and S have been contained, the reactionless activity of its molecular chain and epoxy.
Polynite is for the toughening effect of polymeric system, depends on the existence-intercal type of polynite in system or exfoliated, and exfoliated polynite is the most obvious for the toughening effect of system.For epoxy systems, can finally form exfoliated montmorillonite composite material, key depends on 2 points: whether (1) interlayer reaction liberated heat can overcome magnetism between cheating engaging layer; (2) before reaching gelation point, whole system can finish stripping process.Analyze existing patent, what most systems adopted is that long-chain fat family ammonium salt is as organic modifiers, increase the cheating engaging layer spacing, help Resins, epoxy and solidifying agent to enter the interlayer reaction, such properties-correcting agent can not react between promoting layer, therefore the epoxy and the solidifying agent molecule that enter interlayer are reacted prior to whole system, thereby help to obtain exfoliated polynite-epoxy composite material, therefore, adopt the technology of this type of intercalator, often need to adopt high temperature or strong shearing force could help to obtain exfoliated matrix material in preparation process, this has just increased the complicacy of technology and the unstable of material property." US5801216 " selected to contain the properties-correcting agent of active group, but its effect be with the polynite binding in cross-linking system, can not help peeling off of polynite.
Summary of the invention
The objective of the invention is to overcome the deficiencies in the prior art, a kind of intercalator and preparation method thereof is provided, can increase the montmorillonite layer spacing, increase the possibility that epoxy and solidifying agent molecule enter interlayer, and can in solidification process, help montmorillonite layer effectively to peel off.
According to technical scheme provided by the invention, described intercalator is the intercalator that contains phenolic group or thiophenol base, and the structure of described intercalator is:
Wherein X be-OH or-SH;
A is H or OH;
B is H or CH
3
Y be H, OH, the tertiary butyl, nonyl,
In a kind of;
R is a kind of in the following structure: the alkane structure C of straight chain or side chain
nH
2n, n=1～18;
X=1～10 or x=0, y=1～10 or y=0;
The component of described intercalator comprises aminated compounds, formaldehyde and phenolic compound, and the mol ratio of each component is 1: 0.5～1: 0.5～1;
Described aminated compounds is the aminated compounds that contains two primary aminos in the structure, and the structure of described aminated compounds is:
N=4～18;
X=1～10 or x=0, y=1～10 or y=0;
X=1～10 or x=0, y=1～10 or y=0; 2,2,4-trimethylammonium-1,6-hexanediamine; M-xylene diamine or 1,3-two (aminomethyl) hexanaphthene;
Described phenolic compound is phenol, Resorcinol, Resorcinol, dihydroxyphenyl propane, Bisphenol F, p-tert-butylphenol, nonyl phenol, thiophenol or 2 (4)-methyl thiophenols.
Contain primary amino and phenolic group or thiophenol base in the structure of described intercalator simultaneously.
A kind of preparation method of intercalator, feature are to comprise following processing step:
A, when the Tc of aminated compounds smaller or equal to 25 ℃:
Aminated compounds is added in the reactor, and low whipping speed is to be added dropwise to formaldehyde under 20～500 rev/mins the condition, and controlled temperature is 25～45 ℃, is added dropwise to complete in 0.5～4 hour; After being added dropwise to complete, continue reaction 0.5～2 hour; In reactor, add phenolic compound, be warming up to 50～60 ℃, reacted 0.5～2 hour; Be warming up to 80～100 ℃, reacted 2～6 hours; Be warming up to 120 ℃～150 ℃, react 2～6 hours, obtain described intercalator to steam moisture;
B, when the aminated compounds Tc greater than 25 ℃:
Aminated compounds is mixed in reactor with phenolic compound, and controlled temperature is 25～75 ℃, and low whipping speed is to drip formaldehyde under 20～500 rev/mins the condition, is added dropwise to complete in 0.5～4 hour; After being added dropwise to complete, continue reaction 0.5～2 hour; Reactor is warming up to 80～100 ℃, reacted 2～6 hours; Be warming up to 120 ℃～140 ℃, react 2～6 hours, obtain intercalator to steam moisture.
The present invention and traditional intercalator are relatively, contain phenolic group or thiophenol base in the intercalator structure of the present invention, carry out intercalation with it for montmorillonite layer, except increasing the montmorillonite layer spacing, increase epoxy and solidifying agent molecule and enter outside the possibility of interlayer, effectively the reactive behavior of epoxide group and amido between promoting layer makes the interlayer reaction carry out prior to whole system, before whole system reaches gelation point, emit reaction heat, thereby make montmorillonite layer realize peeling off.
Embodiment
The invention will be further described below in conjunction with specific embodiment.
Embodiment 1, and the 232g hexanediamine is mixed in reactor with 169.2g phenol, and controlled temperature is 50 ℃, and low whipping speed is that to drip concentration under 200 rev/mins the condition be 37% formaldehyde 146g, is added dropwise to complete in 2 hours; After being added dropwise to complete, continue reaction 1 hour; Reactor is warming up to 95 ℃, reacted 4 hours; Be warming up to 140 ℃, reacted 2 hours, water outlet 120.5g obtains the intercalator of 419g, and the molecular structural formula of the intercalator that obtains is:
The intercalator that obtains is used to prepare the organic modification polynite: the intercalator that obtains is mixed according to 1: 10 ratio of weight ratio with deionized water, and dripping concentration is the hydrochloric acid soln of 5mol/L, to the pH value be between 6～7, obtain the intercalator salts solution;
The 20g polynite is scattered in the ionized water of 500g, stirs 30min under the condition that low whipping speed is 300 rev/mins, obtain the suspension liquid of polynite, the pH value of described polynite suspension liquid is between 7～8; The polynite suspension liquid is warming up to 80 ℃, adds intercalator salts solution (containing intercalator salt 6g), stirred 12 hours under the condition that low whipping speed is 300 rev/mins, the positively charged ion between intercalator and polynite is fully exchanged;
The gained suspension liquid carries out centrifuging, with deionized water the solid that filtration obtains is carried out repeated washing, with silver nitrate solution the deionized water after washing is detected, and generates until no white precipitate.The solid that obtains is-0.1 in vacuum tightness～-carry out vacuum-drying under the condition of 0.09MPa, vacuum drying temperature is 40 ℃, the vacuum-drying time is 48 hours; Solid after the vacuum-drying pulverized to be ground to can pass through 200 mesh sieves,, promptly obtain the organic modification polynite;
Embodiment 2, and 460g Amino Terminated polyether(ATPE) D-230 is added in the reactor, and low whipping speed is to be added dropwise to 146g formaldehyde under 200 rev/mins the condition, and controlled temperature is no more than 45 ℃, is added dropwise to complete in 1 hour; After being added dropwise to complete, continue reaction 1 hour; In reactor, add phenol 169.2g, be warming up to 60 ℃, reacted 2 hours; Be warming up to 95 ℃, reacted 4 hours; Be warming up to 140 ℃, reacted 2.5 hours, water outlet 118.6g obtains the intercalator of 638.5g, and the intercalator structure that obtains is:
Embodiment 3, and the 272g m-xylene diamine is added in the reactor, and low whipping speed is to be added dropwise to formaldehyde 146g under 200 rev/mins the condition, and controlled temperature is no more than 45 ℃, is added dropwise to complete in 2 hours; After being added dropwise to complete, continue reaction 1 hour; In reactor, add phenol, be warming up to 60 ℃, reacted 2 hours; Be warming up to 95 ℃, reacted 4 hours; Be warming up to 120 ℃, reacted 2 hours, water outlet 119.3g obtains the intercalator of 458g, and the intercalator structure that obtains is:
Embodiment 4, and the 232g hexanediamine is mixed in reactor with the 374g nonyl phenol, and controlled temperature is 50 ℃, and low whipping speed is to drip formaldehyde 137.9g under 200 rev/mins the condition, is added dropwise to complete in 2 hours; After being added dropwise to complete, continue reaction 1 hour; Reactor is warming up to 95 ℃, reacted 4 hours; Be warming up to 140 ℃, reacted 2 hours, water outlet 115.1g obtains the intercalator of 624g, and the structure of the intercalator that obtains is:
Embodiment 5, and the 272g m-xylene diamine is added in the reactor, and low whipping speed is to be added dropwise to 129.7g formaldehyde under 200 rev/mins the condition, and controlled temperature is no more than 45 ℃, is added dropwise to complete in 2 hours; After being added dropwise to complete, continue reaction 1 hour; In reactor, add nonyl phenol, be warming up to 60 ℃, reacted 2 hours; Be warming up to 95 ℃, reacted 4 hours; Be warming up to 140 ℃, reacted 2 hours, water outlet 109.0g obtains the intercalator of 632g, and the intercalator structure that obtains is:
Embodiment 6, and with 2,2 of 316g, 4-trimethylammonium-1,6-hexanediamine aminated compounds add in the reactor, and low whipping speed is to be added dropwise to formaldehyde 146g under 200 rev/mins the condition, and controlled temperature is no more than 45 ℃, is added dropwise to complete in 2 hours; After being added dropwise to complete, continue reaction 1 hour; In reactor, add phenol, be warming up to 60 ℃, reacted 2 hours; Be warming up to 95 ℃, reacted 4 hours; Be warming up to 140 ℃, reacted 2 hours, water outlet 121.5g obtains the intercalator of 495g, and the intercalator structure that obtains is:
Embodiment 7, and with 1 of 284g, 3-two (aminomethyl) hexanaphthene adds in the reactor, and low whipping speed is to be added dropwise to formaldehyde 146g under 200 rev/mins the condition, and controlled temperature is no more than 45 ℃, is added dropwise to complete in 2 hours; After being added dropwise to complete, continue reaction 1 hour; In reactor, add phenol, be warming up to 60 ℃, reacted 2 hours; Be warming up to 95 ℃, reacted 4 hours; Be warming up to 140 ℃, reacted 2 hours, water outlet 118.8g obtains the intercalator of 465g, and the intercalator structure that obtains is:
Claims (4)
1. an intercalator is characterized in that, described intercalator is the intercalator that contains phenolic group or thiophenol base, and the structure of described intercalator is:
Wherein X be-OH or-SH;
A is H or OH;
B is H or CH
3
Y is H, OH, and the tertiary butyl, nonyl,
In a kind of;
R is a kind of in the following structure: the alkane structure C of straight chain or side chain
nH
2n, n=1～18;
2. intercalator as claimed in claim 1 is characterized in that its component comprises aminated compounds, formaldehyde and phenolic compound, and the mol ratio of each component is 1: 0.5～1: 0.5～1;
Described aminated compounds is the aminated compounds that contains two primary aminos in the structure, and the structure of described aminated compounds is:
N=4～18;
X=0～10, y=0～10;
X=0～10, y=0～10; 2,2,4-trimethylammonium-1,6-hexanediamine; M-xylene diamine or 1,3-two (aminomethyl) hexanaphthene;
Described phenolic compound is phenol, Resorcinol, Resorcinol, dihydroxyphenyl propane, Bisphenol F, p-tert-butylphenol, nonyl phenol, thiophenol or 2 (4)-methyl thiophenols.
3. intercalator as claimed in claim 1 is characterized in that, contains primary amino and phenolic group or thiophenol base in the structure of described intercalator simultaneously.
4. the preparation method as claim 1,2 or 3 described intercalators is characterized in that, comprises following processing step:
A, when the Tc of aminated compounds during smaller or equal to 25 ℃:
Aminated compounds is added in the reactor, and low whipping speed is to be added dropwise to formaldehyde under 20～500 rev/mins the condition, and controlled temperature is 25～45 ℃, is added dropwise to complete in 0.5～4 hour; After being added dropwise to complete, continue reaction 0.5～2 hour; In reactor, add phenolic compound, be warming up to 50～60 ℃, reacted 0.5～2 hour; Be warming up to 80～100 ℃, reacted 2～6 hours; Be warming up to 120 ℃～150 ℃, react 2～6 hours, obtain described intercalator to steam moisture;
B, when aminated compounds Tc during greater than 25 ℃:
Aminated compounds is mixed in reactor with phenolic compound, and controlled temperature is 25～75 ℃, and low whipping speed is to drip formaldehyde under 20～500 rev/mins the condition, is added dropwise to complete in 0.5～4 hour; After being added dropwise to complete, continue reaction 0.5～2 hour; Reactor is warming up to 80～100 ℃, reacted 2～6 hours; Be warming up to 120 ℃～150 ℃, react 2～6 hours, obtain intercalator to steam moisture.
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| CN201010593288XA CN102061011B (en) | 2010-12-17 | 2010-12-17 | Intercalator and preparation method thereof |
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| CN102061011B CN102061011B (en) | 2012-08-08 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102504338A (en) * | 2011-11-07 | 2012-06-20 | 上海工程技术大学 | Branch-shaped damping agent and preparation method and use thereof |
| JP2014531496A (en) * | 2011-09-23 | 2014-11-27 | エア プロダクツ アンド ケミカルズ インコーポレイテッドＡｉｒ Ｐｒｏｄｕｃｔｓ Ａｎｄ Ｃｈｅｍｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | Benzylated polyamine curing agent |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004299238A (en) * | 2003-03-31 | 2004-10-28 | Jfe Steel Kk | Polyolefin-coated steel |
-
2010
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004299238A (en) * | 2003-03-31 | 2004-10-28 | Jfe Steel Kk | Polyolefin-coated steel |
Non-Patent Citations (1)
| Title |
|---|
| 《化学与黏合》 20050720 鹿桂芳等 "酚醛改性胺环氧树脂固化剂研究进展" 233-236 2,4 第27卷, 第4期 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014531496A (en) * | 2011-09-23 | 2014-11-27 | エア プロダクツ アンド ケミカルズ インコーポレイテッドＡｉｒ Ｐｒｏｄｕｃｔｓ Ａｎｄ Ｃｈｅｍｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | Benzylated polyamine curing agent |
| CN102504338A (en) * | 2011-11-07 | 2012-06-20 | 上海工程技术大学 | Branch-shaped damping agent and preparation method and use thereof |
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| CN102061011B (en) | 2012-08-08 |
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