CN102432813B - Method for preparing PIR (polyisocyanurate) material with ionic liquid catalyst - Google Patents
Method for preparing PIR (polyisocyanurate) material with ionic liquid catalyst Download PDFInfo
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- CN102432813B CN102432813B CN201110250760.4A CN201110250760A CN102432813B CN 102432813 B CN102432813 B CN 102432813B CN 201110250760 A CN201110250760 A CN 201110250760A CN 102432813 B CN102432813 B CN 102432813B
- Authority
- CN
- China
- Prior art keywords
- ionic liquid
- combined polyether
- pir
- use according
- pir material
- Prior art date
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- Expired - Fee Related
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- 239000000463 material Substances 0.000 title claims abstract description 38
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 21
- 239000003054 catalyst Substances 0.000 title claims abstract description 12
- 229920000582 polyisocyanurate Polymers 0.000 title abstract 8
- 239000011495 polyisocyanurate Substances 0.000 title abstract 8
- 229920000570 polyether Polymers 0.000 claims abstract description 38
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 37
- 238000005187 foaming Methods 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- -1 polyoxypropylene Polymers 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- 229920005862 polyol Polymers 0.000 claims description 7
- 150000003077 polyols Chemical class 0.000 claims description 7
- 229920001451 polypropylene glycol Polymers 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229920005906 polyester polyol Polymers 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- QVRCRKLLQYOIKY-UHFFFAOYSA-M 1-methyl-3-prop-2-enylimidazol-1-ium;chloride Chemical compound [Cl-].C[N+]=1C=CN(CC=C)C=1 QVRCRKLLQYOIKY-UHFFFAOYSA-M 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 abstract description 3
- 239000012948 isocyanate Substances 0.000 abstract 2
- 150000002513 isocyanates Chemical class 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 229920002635 polyurethane Polymers 0.000 description 5
- 239000004814 polyurethane Substances 0.000 description 5
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical group C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 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 description 1
- 229910014201 BMIMBF4 Inorganic materials 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000003915 liquefied petroleum gas Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002730 mercury Chemical class 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention discloses a method for preparing a PIR (polyisocyanurate) material with an ionic liquid catalyst. By utilizing the catalytic activity and other performances of an ionic liquid to prepare a PIR material, the method comprises: first mixing an ionic liquid with a combined polyether, then injecting the mixture and isocyanates into a mould for reaction by a high-pressure foaming machine, or directly injecting the ionic liquid, the combined polyether and isocyanates into a mould for reaction by a high-pressure foaming machine, conducting demoulding after reaction, thus obtaining a PIR material. The method of the invention accelerates the curing speed of PIR, avoids using a volatile catalyst, and also optimizes performances of the PIR material.
Description
Technical field
The invention belongs to PIR field of material preparation, be specifically related to a kind of method that adopts the ionic liquid-catalyzed PIR of preparation material.
Background technology
Polyurethane material has been widely used in the industry-by-industries such as automobile, building, household electrical appliances, the energy.Wherein PIR material (poly-isocyanuric acid fat) is with its good flame retardant resistance, the lower line style coefficient of expansion and thermal conductivity, in fields such as natural gas liquids, liquefied ethylene, liquefied petroleum gas storage transportation and building heat preservation are heat insulation, is widely used.But due to the reaction process complexity of PIR material, maturing process is slow, very strict to the requirement of complete processing.In addition, the catalyzer of traditional amine, tin class and mercury class also has certain pollution to environment.
Ionic liquid refers to the liquid being all comprised of ion.If the melting such as KCl, KOH under high temperature is liquid, this liquid is exactly ionic liquid.Usually said ionic liquid, refers to be at room temperature liquid, and the compound being all comprised of ion, claims again ionic liquid at room temperature.Ionic liquid is the green catalyst that a class of rising in recent years has application prospect, with the strong polarity of its uniqueness, non-volatile, the premium propertiess such as water and air is stable are widely used in to the research that electrochemistry, organic reaction, chemical separating, material such as prepare at the field, be acknowledged as the environmentally friendly catalyzer that can substitute in a lot of fields easy volatile.
In forming materials application, ionic liquid is used as solvent more, HeFei University of Technology has announced with ionic liquid as solvent, prepare the method (preparation of cellulose base polyurethane material in imidazolium ionic liquid of cellulose base polyurethane material, Wang Chuanhang etc., Guangdong chemical industry, 37 volumes, 205 phases).The method of preparing comb type polyurethane macromolecular ionic liquid material has been studied by University Of Science and Technology Of He'nan, and has submitted patent application (CN101628962A) to.And with the direct catalyze polyurethane reaction of ionic liquid, the especially application of PIR reaction, have no report.
Summary of the invention
The object of this invention is to provide the preparation method of the ionic liquid-catalyzed PIR material of a kind of use, specifically utilize catalytic activity, non-volatility and other characteristics of ionic liquid, prepare the method for PIR material, the defects such as the slaking that prior art exists is slow to make up, catalyst contamination sublimity.
Object of the present invention can reach by following measures:
A kind of ionic liquid-catalyzed method of preparing PIR material of use, catalytic activity and other performances of utilizing ionic liquid, preparation PIR material, the method is: first ionic liquid and combined polyether are mixed, via high pressure foaming machine, injecting mould again together with isocyanide ester reacts, or directly ionic liquid, combined polyether and isocyanide ester are injected to mould via high pressure foaming machine and react, after reaction, the demoulding obtains PIR material;
The mass ratio of described ionic liquid and combined polyether is 0.1～10: 90～99.9, and the mass ratio of described ionic liquid and isocyanide ester is 0.1～10: 90～99.9.Wherein said combined polyether comprises one or more in polyether glycol and polyester polyol; Further comprise two or more in polyoxypropylene polyol, polyoxyethylene polyvalent alcohol, polymer polyatomic alcohol and Aromatic Polyester Polyols.
Above-mentioned polyoxypropylene polyol, polyoxyethylene polyvalent alcohol, polymer polyatomic alcohol and the Aromatic Polyester Polyols mass content in combined polyether is preferably: polyoxypropylene polyol 45%～98%, (preferably 45%～90%, further preferably 55%～85%), polyoxyethylene polyvalent alcohol 2%～20% (preferably 2%～18%, further preferably 2%～10%), polymer polyatomic alcohol 10%～98% (preferably 10%～70%, further preferably 10%～30%), Aromatic Polyester Polyols 5%～60% (preferably 5%～50%, further preferably 20%～30%).
The mass ratio of intermediate ion liquid of the present invention and combined polyether is for being preferably 0.1～8: 92～99.9, and the mass ratio of ionic liquid and isocyanide ester is 0.1～8: 92～99.9.
This combined polyether can also comprise amines catalyst; Described amines catalyst is preferably triethylene diamine; The mass content of described amines catalyst in combined polyether is 0.4%～3%, is preferably 0.5%～2%.
This combined polyether can also comprise whipping agent; It (is CH that described whipping agent is preferably HCFC141b
3cCl
2f) whipping agent; The mass content of whipping agent in combined polyether is 5%～15%, is preferably 8%～11%, more preferably 9%～10%.
This combined polyether, not damaging in the scope of effect of the present invention, also can further contain mill base, fire retardant, cocatalyst, tensio-active agent or filler etc., and the consumption of aforementioned each component can be selected in the scope of prior art.
This combined polyether is not strict with hydroxyl value, but its hydroxyl value can reach better effect within the scope of 150～350mgKOH/g.
Isocyanide ester of the present invention can be MDI (diphenylmethanediisocyanate) or pMDI (polymerization diphenylmethanediisocyanate, also referred to as thick MDI).
The positively charged ion of ionic liquid of the present invention is alkyl imidazole ion:
Wherein R
1, R
2, R
3, R
4or R
5be H or C independently respectively
1-8alkyl.
The negatively charged ion of ionic liquid is selected from COOH
-, Cl
-, BF
4 -, PF
6 -, CF
3sO
3 -, CF
3cOO
-, CH
3cOO
-, Br
-, (CF
3sO
2)
2n
-, (CF
3sO
2)
2c
-one.
Ionic liquid of the present invention preferably adopts AMIMCl, BMIMBF
4or BMIMCH
3cOOH.
The mixing of present method intermediate ion liquid and combined polyether, or the mixing of ionic liquid, combined polyether and isocyanide ester are carried out at 10～50 ℃.
In present method, have a high pressure foaming machine and the mould that can control temperature at least.By high pressure foaming machine, the isocyanic ester that contains ionic liquid and combined polyether are mixed and inject mould.
The mass ratio of combined polyether and isocyanic ester is preferably: 2: 1 to 1: 5.
According to the quality of reactant, foaming machine pressure-controlling is at 10MPa to 900MPa.
According to the mass ratio of polyethers and isocyanic ester, die temperature is controlled at 10 ℃～90 ℃.
Demould time (reaction times) is controlled at 1 minute to 36 hours.Prior art middle-high density system demould time is longer, and common system demould time about 48 hours time, is used this ion liquid system can make demould time foreshorten in 36 hours.
The invention has the advantages that a kind of a kind of preparation method based on ionic liquid-catalyzed PIR material that utilizes is provided, accelerated the slaking speed of PIR, avoided use volatile catalyst, but also optimized the performance of PIR material.
Embodiment
Embodiment 1
3920g combined polyether, hydroxyl value is about 200mgKOH/g, wherein:
Fully mix under the condition of 40 ℃ with 80g ionic liquid AMIMCl, through high-pressure unit, inject mould with 6000g pMDI and react, 25 ℃ of temperature of charge, high-pressure unit pressure 15MPa, 40 ℃ of die temperatures.The demoulding after 30 minutes, obtaining density is 70kg/m
3pIR material.
Embodiment 2
7870g combined polyether, hydroxyl value is about 180mgKOH/g, wherein:
Fully mix under the condition of 20 ℃ with 130g ionic liquid BMIMBF4, through high-pressure unit, inject mould with 16000g pMDI and react, 25 ℃ of temperature of charge, high-pressure unit pressure 35MPa, 50 ℃ of die temperatures.The demoulding after 60 minutes, obtaining density is 50kg/m
3pIR material.
Embodiment 3
39200g combined polyether, hydroxyl value is about 300mgKOH/g, wherein:
Polyoxypropylene polyol 85%
Polyoxyethylene polyvalent alcohol 2%
Polymer polyatomic alcohol 13%
(hydroxyl value is about 240mgKOH/g) and 800g ionic liquid BMIMCH
3cOOH fully mixes under the condition of 20 ℃, injects mould and reacts, 25 ℃ of temperature of charge, high-pressure unit pressure 45MPa, 60 ℃ of die temperatures with 80000g pMDI through high-pressure unit.The demoulding after 600 minutes, obtaining density is 500kg/m
3pIR material.
Comparative example 1:
39200g combined polyether, hydroxyl value is about 300mgKOH/g, wherein:
Polyoxypropylene polyol 85%
Polyoxyethylene polyvalent alcohol 2%
Polymer polyatomic alcohol 13%
(hydroxyl value is about 240mgKOH/g) and 800g triethylene diamine fully mix under the condition of 20 ℃, inject mould and react, 25 ℃ of temperature of charge, high-pressure unit pressure 45MPa, 60 ℃ of die temperatures with 80000g pMDI through high-pressure unit.The demoulding after 1200 minutes, obtaining density is 500kg/m
3pIR material.
The PIR material property contrast that embodiment 3 and comparative example 1 obtain is as follows:
| Testing standard | Embodiment 3 | Comparative example 1 | |
| Demould time (minute) | 600 | 1200 | |
| Thermal conductivity (W*m -1K -1) | ASTM C177 | 0.078 | 0.096 |
| Compressive strength (MPa) | ASTM D1621 | 30.19 | 23.58 |
| Flame height (cm) | DIN 4102B2 | 9 | 14 |
As can be seen from the table, the PIR material of ionic liquid-catalyzed preparation, is all better than the PIR material of common amines catalyst system from all respects such as demould time, thermal conductivity, compressive strength and flame heights.
Claims (7)
1. one kind by the ionic liquid-catalyzed method of preparing PIR material, it is characterized in that: first ionic liquid and combined polyether are mixed, via high pressure foaming machine, injecting mould again together with isocyanic ester reacts, or directly ionic liquid, combined polyether and isocyanic ester are injected to mould via high pressure foaming machine and react, after reaction, the demoulding obtains PIR material;
The mass ratio of described ionic liquid and combined polyether is 0.1～10:90～99.9, and the mass ratio of described ionic liquid and isocyanic ester is 0.1～10:90～99.9; Described combined polyether comprises two or more in polyoxypropylene polyol, polyoxyethylene polyvalent alcohol, polymer polyatomic alcohol and Aromatic Polyester Polyols, described polyoxypropylene polyol, polyoxyethylene polyvalent alcohol, polymer polyatomic alcohol or the mass content of Aromatic Polyester Polyols in combined polyether are respectively 45%～98%, 2%～20%, 10%～98% or 5%～60%, and in described combined polyether, the quality sum of each component is 100%; Described ionic liquid is AMIMCl or BMIMBF
4.
2. the ionic liquid-catalyzed method of preparing PIR material of use according to claim 1, is characterized in that: described combined polyether also comprises amines catalyst, and the mass content of described amines catalyst in combined polyether is 0.4%～3%.
3. the ionic liquid-catalyzed method of preparing PIR material of use according to claim 1, is characterized in that: described combined polyether also comprises whipping agent; The mass content of described whipping agent in combined polyether is 5%～15%.
4. the ionic liquid-catalyzed method of preparing PIR material of use according to claim 1, is characterized in that: the hydroxyl value of described combined polyether is 150～350mgKOH/g; Described isocyanic ester is MDI or pMDI.
5. the ionic liquid-catalyzed method of preparing PIR material of use according to claim 1, is characterized in that: the mixing of described ionic liquid and combined polyether, or the mixing of ionic liquid, combined polyether and isocyanic ester, at 10～50 ℃, carry out.
6. the ionic liquid-catalyzed method of preparing PIR material of use according to claim 1, is characterized in that: the mass ratio of described combined polyether and isocyanic ester is 2:1～1:5.
7. the ionic liquid-catalyzed method of preparing PIR material of use according to claim 1, is characterized in that: the pressure of described high pressure foaming machine is 10MPa～900MPa; The temperature of described mould is 10 ℃～90 ℃, and the reaction times is 1 minute～36 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110250760.4A CN102432813B (en) | 2011-03-21 | 2011-08-29 | Method for preparing PIR (polyisocyanurate) material with ionic liquid catalyst |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110067368 | 2011-03-21 | ||
| CN201110067368.6 | 2011-03-21 | ||
| CN201110250760.4A CN102432813B (en) | 2011-03-21 | 2011-08-29 | Method for preparing PIR (polyisocyanurate) material with ionic liquid catalyst |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102432813A CN102432813A (en) | 2012-05-02 |
| CN102432813B true CN102432813B (en) | 2014-04-30 |
Family
ID=45981189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201110250760.4A Expired - Fee Related CN102432813B (en) | 2011-03-21 | 2011-08-29 | Method for preparing PIR (polyisocyanurate) material with ionic liquid catalyst |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102432813B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106633467B (en) * | 2015-11-04 | 2019-01-01 | 上海越科复合材料有限公司 | A method of preparing hard sandwich crosslinked PVC foamed material |
| CN108467468B (en) * | 2018-04-03 | 2021-02-26 | 江苏中昌绝热技术工程有限公司 | Polyisocyanurate material catalyzed by ionic liquid and preparation method thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10219227A1 (en) * | 2002-04-30 | 2003-11-13 | Bayer Ag | Ionic liquids |
| EP1551909A4 (en) * | 2002-07-18 | 2007-12-26 | Huntsman Spec Chem Corp | Catalyst combinations for increasing trimer content in foam |
| US20080262186A1 (en) * | 2004-05-19 | 2008-10-23 | University Of Utah Research Foundation | Catalysts for the Production of Polyisocyanates |
| EP2346919B1 (en) * | 2008-11-10 | 2013-09-04 | Dow Global Technologies LLC | Isocyanate trimerisation catalyst system, a precursor formulation, a process for trimerising isocyanates, rigid polyisocyanurate/polyurethane foams made therefrom, and a process for making such foams |
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2011
- 2011-08-29 CN CN201110250760.4A patent/CN102432813B/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN102432813A (en) | 2012-05-02 |
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