CN106632988B - A kind of modified MDI, polyurethane foam and preparation method thereof - Google Patents
A kind of modified MDI, polyurethane foam and preparation method thereof Download PDFInfo
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- CN106632988B CN106632988B CN201611237838.8A CN201611237838A CN106632988B CN 106632988 B CN106632988 B CN 106632988B CN 201611237838 A CN201611237838 A CN 201611237838A CN 106632988 B CN106632988 B CN 106632988B
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- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4804—Two or more polyethers of different physical or chemical nature
- C08G18/4816—Two or more polyethers of different physical or chemical nature mixtures of two or more polyetherpolyols having at least three hydroxy groups
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0025—Foam properties rigid
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0083—Foam properties prepared using water as the sole blowing agent
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention discloses a kind of modified MDI, polyurethane foam and preparation method thereof, after the preparation method of the modified MDI is the following steps are included: be warming up to certain temperature for isocyanates, acid anhydrides and epoxide are sequentially added, reaction is until-NCO content reaches requirement；The preparation method of the polyurethane foam of the modified MDI has been used the following steps are included: combined polyether and modified MDI are uniformly mixed post curing for a period of time.The present invention substantially increases the heat resistance of final hard polyurethane foam obtained, gained hard polyurethane foam product can be used for a long time under 200 DEG C of environment, have broad application prospects by introducing polyimides and oxazolidone structure in isocyanates.
Description
Technical field
The present invention relates to a kind of modified MDI, polyurethane foam and preparation method thereof.
Background technique
Hard polyurethane foam is the organic insulation material that one kind is used widely in recent years, light, heat-insulated, heat preservation, but
Defect is poor heat resistance, easy firing, easy to aging, fire savety is poor, and can largely have poison gas releasing in burning
Body and smog cause to seriously threaten to production safety.
In the prior art, the use temperature range of conventional polyurethanes hard bubble is generally at 120 DEG C hereinafter, after more than 120 DEG C
The structures such as the carbamate in foaming structure will appear decomposition；And if when used for a long time at 80 DEG C or more, will appear
Serious performance degradation.And polysiocyanurate rigid foams plastics modified are although heat resistance is improved,
150 DEG C or more can also decompose.In some fields for needing high-temperature resistant, the use of hard polyurethane foam is just restricted.
Summary of the invention
The present invention is to solve the poor problem of hard polyurethane foam heat resistance in the prior art, provides a kind of modification
MDI, polyurethane foam and preparation method thereof.
The present invention solves above-mentioned technical problem by following technical proposals:
The present invention provides the preparation methods of modified MDI a kind of comprising following steps: isocyanates is warming up to 120
~140 DEG C, acid anhydrides and epoxide are sequentially added, reaction is until when-NCO content is 15~25%；
Wherein, the dosage of the isocyanates is calculated by weight as 2541~7536 parts, the viscosity of the isocyanates
For 200mPas, the isocyanates-NCO content is 30.5-32%；
The dosage of the acid anhydrides is calculated by weight as 96~480 parts, and the acid anhydrides is phthalic anhydride, maleic acid
One of acid anhydride, acetic anhydride and trimellitic anhydride；
The dosage of the epoxide is calculated by weight as 170~850 parts；
The dosage molar ratio of the acid anhydrides and the epoxide is 1:5~5:1.
In the present invention, the isocyanates is isocyanates (MDI) of this field conventionally used for preparing combined polyether, generally
Refer to 4,4' methyl diphenylene diisocyanate (pure MDI), contain the pure MDI of certain proportion and polyphenyl polymethylene polyisocyanates
Mixture (polymeric MDI) and pure MDI and polymeric MDI modifier general name；The isocyanates is preferably trade mark PM-
200 isocyanates, manufacturer are Wanhua Chemical Group Co., Ltd..
In the present invention, the acid anhydrides is preferably trimellitic anhydride；The trimellitic anhydride is that field is conventional, molecular formula
For C9H4O5, molecular weight 192, appearance is white plates, and 164~166 DEG C of fusing point, 240~245 DEG C of boiling point, content is greater than
99%.
In the present invention, the acid anhydrides preferably divides 3~8 additions.
In the present invention, the epoxide be epoxide commonly used in the art, by epoxide with it is miscellaneous
It is this field routine that cumulene (heterocumulene), which carries out cycloaddition reaction with synthesizing heterocyclic compound such as oxazolidone,
One of organic synthesis means；The epoxide is preferably bisphenol A diglycidyl ether or ethylene glycol diglycidyl
Ether.
In the present invention, the epoxide preferably divides 3~8 additions.
The present invention also provides a kind of modification MDI as obtained by method made above.
The present invention also provides a kind of preparation methods of polyurethane foam for having used above-mentioned modified MDI comprising following
Step: combined polyether and modified MDI are uniformly mixed post curing；
Wherein, the mass parts ratio of the combined polyether and the modified MDI are 1:2~1:1；
The temperature of the curing is 40~60 DEG C, and the time of the curing is 5~15min.
In the present invention, the combined polyether is the raw material used when this field routinely prepares polyurethane foam, wherein type
It can be used according to this field conventional selection with dosage；The raw material of the combined polyether is preferably comprised according to parts by weight: 70
Part polyether polyol A, 20 parts of polyether polyol B, 10 parts of polyether polyol C, 2 parts of foam stabilisers, 1.5~2 parts of catalyst and
0.4 part of water；
The polyether polyol A be degree of functionality 4~5, hydroxyl value be 435~465mgKOH/g, viscosity (25 DEG C) 2000~
4000mPas, moisture content are less than the polyether polyol of 0.1wt%, the preferably polyether polyol of the trade mark 4110, life
Production producer is Shandong Inov New Material Co., Ltd.；
The polyether polyol B be degree of functionality 3, hydroxyl value be 330~350mgKOH/g, viscosity (25 DEG C) 200~
400mPas, moisture content are less than the polyether polyol of 0.1wt%, the preferably polyether polyol of the trade mark 305, production
Producer is Shandong Inov New Material Co., Ltd.；
The polyether polyol C is degree of functionality 2, and hydroxyl value is 270~290mgKOH/g, viscosity (25 DEG C) 60~80mPa
S, moisture content are less than the polyether polyol of 0.1wt%, the preferably polyether polyol of the trade mark 204, and manufacturer is mountain
An eastern Nowe new material Co., Ltd.
The foam stabiliser is foam stabiliser commonly used in the art, the preferably foam of trade mark B-8545
Stabilizer, manufacturer are Evonik Degussa (China) Co., Ltd..
The catalyst is catalyst commonly used in the art, preferably amines catalyst or metal organic catalysis
Agent is more preferably tertiary amine catalyst, more preferably contains N, N '-dimethyl cyclohexylamine is with quaternary ammonium salt catalyst TMR-2's
The mass ratio of composite catalyst, the N, N '-dimethyl cyclohexylamine and the quaternary ammonium salt catalyst TMR-2 be preferably 1:1~
2:1。
The water is water commonly used in the art, preferably deionized water.
In the present invention, the preparation method of the combined polyether is the combined polyether preparation method of this field routine, including with
Lower step: the raw material of the combined polyether is mixed, stirring；
Wherein, the whipping temp of the stirring is preferably 15~30 DEG C；
The stirring rate of the stirring is preferably 400~600r/min；
The mixing time of the stirring is preferably 0.8~1.2h.
In the present invention, the temperature of the curing is preferably 45 DEG C.
In the present invention, the time of the curing is preferably 10min.
On the basis of common knowledge of the art, above-mentioned each optimum condition, can any combination to get each preferable reality of the present invention
Example.
The reagents and materials used in the present invention are commercially available.
The positive effect of the present invention is that: the present invention is by introducing polyimides and oxazole in isocyanates (MDI)
Alkanone structure substantially increases the heat resistance of final hard polyurethane foam obtained, and products obtained therefrom hard polyurethane foam can be in 200 DEG C of rings
It is used for a long time under border.
Specific embodiment
The present invention is further illustrated below by the mode of embodiment, but does not therefore limit the present invention to the reality
It applies among a range.In the following examples, the experimental methods for specific conditions are not specified, according to conventional methods and conditions, or according to quotient
The selection of product specification.
In the following each embodiment and comparative examples of the present invention, raw material sources are as follows: it is mountain that polyether polyol A, which selects manufacturer,
An eastern Nowe new material Co., Ltd polyether polyol 4110, it is one Nowe green wood of Shandong that polyether polyol B, which selects manufacturer,
Expect Co., Ltd's polyether polyol 305, it is Shandong Inov New Material Co., Ltd.'s polyethers that polyether polyol C, which selects manufacturer,
Polyalcohol 204, it is the foam stabiliser B- of Evonik Degussa (China) Co., Ltd. that foam stabiliser, which selects manufacturer,
8545, catalyst select manufacturer be air chemical products (China) Investment Co., Ltd N, N '-dimethyl cyclohexylamine with
TMR-2, wet concentration self-control deionized water；It is the isocyanide of Wanhua Chemical Group Co., Ltd. that isocyanates, which selects manufacturer,
Acid esters PM-200, trimellitic anhydride are purchased from Guangdong Weng Jiang chemical reagent Co., Ltd, remaining reagent is commercially available.
In the following each embodiment and comparative examples of the present invention, the test of-NCO content is according to chemical industry standard HG/T 2409-
1992 " measurements of isocyanate group content in base polyurethane prepolymer for use as " carry out, and thermal weight loss is than test according to chinese national standard GB/T
27761-2011 " test method of thermogravimetric analyzer weightlessness and surplus " is carried out.
In the following each embodiment and comparative examples of the present invention, isocyanate index is 100.
Embodiment 1
A kind of modified MDI is present embodiments provided, the raw material of the modified MDI includes following components according to parts by weight:
2541 parts of PM-200,96 parts of (2.5mol) trimellitic anhydrides, 850 parts of (0.5mol) ethylene glycol diglycidylethers.
The modified MDI preparation method includes the following steps: that PM-200 is taken to be placed in three-necked flask, is heated to 140 DEG C, with
The revolving speed of 4000-5000r/min stirs, and then again successively by trimellitic anhydride point 5 times, ethylene glycol diglycidylether divides 5 times
It is added in three-necked flask, after reacting 1h, survey-NCO content, when-NCO content is 15%, stopping is reacted up to modified MDI.
The present embodiment additionally provides a kind of high-temperature resistant hard polyurethane foams, and preparation method includes the following steps: group
It closes polyethers and the modified MDI as made from the above method is uniformly mixed for 1:2.0 by mass fraction ratio and is placed in 45 DEG C of molds,
Up to high-temperature resistant hard polyurethane foams after curing 10min；
Wherein, the raw material of the combined polyether includes: that 70 parts of polyether polyol, 4110,20 parts of polyethers are more according to parts by weight
305,10 parts of first alcohol, 204,2 parts of polyether polyol foam stabiliser B-8545,1 part of catalyst n, N '-dimethyl cyclohexylamine, 0.5
Part catalyst TMR-2 and 0.4 part of water；
The preparation method of the combined polyether includes the following steps: said combination polyethers raw material stainless steel mixing kettle is added
It is interior, it is stirred 1 hour under the conditions of 25 DEG C with the revolving speed of 500r/min, blowing is up to high-temperature resistant use for hard bubble of polyurethane combined polyether.
Embodiment 2
A kind of modified MDI is present embodiments provided, the raw material of the modified MDI includes following components according to parts by weight:
2610 parts of PM-200,192 parts of (1mol) trimellitic anhydrides, 340 parts of (1mol) bisphenol A diglycidyl ethers.
The modified MDI preparation method includes the following steps: that PM-200 is taken to be placed in three-necked flask, is heated to 140 DEG C, with
The revolving speed of 4000-5000r/min stirs, and then again successively by trimellitic anhydride point 3 times, bisphenol A diglycidyl ether divides 3 times and adds
Enter into three-necked flask, after reacting 1h, survey-NCO content, when-NCO content is 20%, stopping is reacted up to modified MDI.
The present embodiment additionally provides a kind of high-temperature resistant hard polyurethane foams, and preparation method includes the following steps: group
It closes polyethers and the modified MDI as made from the above method is uniformly mixed for 1:1.5 by mass fraction ratio and is placed in 45 DEG C of molds,
Up to high-temperature resistant hard polyurethane foams after curing 10min；
Wherein, the raw material of the combined polyether includes: that 70 parts of polyether polyol, 4110,20 parts of polyethers are more according to parts by weight
305,10 parts of first alcohol, 204,2 parts of polyether polyol foam stabiliser B-8545,1 part of catalyst n, N '-dimethyl cyclohexylamine, 1 part
Catalyst TMR-2 and 0.4 part of water；
The preparation method of the combined polyether includes the following steps: said combination polyethers raw material stainless steel mixing kettle is added
It is interior, it is stirred 1 hour under the conditions of 25 DEG C with the revolving speed of 500r/min, blowing is up to high-temperature resistant use for hard bubble of polyurethane combined polyether.
Embodiment 3
A kind of modified MDI is present embodiments provided, the raw material of the modified MDI includes following components according to parts by weight:
7536 parts of PM-200,480 parts of (2.5mol) trimellitic anhydrides, 170 parts of (0.5mol) bisphenol A diglycidyl ethers.
The modified MDI preparation method includes the following steps: that PM-200 is taken to be placed in three-necked flask, is heated to 140 DEG C, with
The revolving speed of 4000-5000r/min stirs, and then again successively by trimellitic anhydride point 8 times, bisphenol A diglycidyl ether divides 8 times and adds
Enter into three-necked flask, after reacting 1h, survey-NCO content, when-NCO content is 25%, stopping is reacted up to modified MDI.
The present embodiment additionally provides a kind of high-temperature resistant hard polyurethane foams, and preparation method includes the following steps: group
It closes polyethers and the modified MDI as made from the above method is uniformly mixed for 1:1.25 by mass fraction ratio and is placed on 45 DEG C of molds
It is interior, up to high-temperature resistant hard polyurethane foams after curing 10min；
Wherein, the raw material of the combined polyether includes: that 70 parts of polyether polyol, 4110,20 parts of polyethers are more according to parts by weight
305,10 parts of first alcohol, 204,2 parts of polyether polyol foam stabiliser B-8545,0.5 part of catalyst n, N '-dimethyl cyclohexylamine, 1
Part catalyst TMR-2 and 0.4 part of water；
The preparation method of the combined polyether includes the following steps: said combination polyethers raw material stainless steel mixing kettle is added
It is interior, it is stirred 1 hour under the conditions of 25 DEG C with the revolving speed of 500r/min, blowing is up to high-temperature resistant use for hard bubble of polyurethane combined polyether.
Comparative example 1
Present embodiments provide a kind of hard polyurethane foams, preparation method include the following steps: combined polyether and
PM-200, which is that 1:1.0 is uniformly mixed by mass fraction ratio, to be placed in 45 DEG C of molds, is gathered after curing 10min up to high-temperature resistant hard
Urethane foam；
Wherein, the raw material of the combined polyether includes: that 70 parts of polyether polyol, 4110,20 parts of polyethers are more according to parts by weight
305,10 parts of first alcohol, 204,2 parts of polyether polyol foam stabiliser B-8545,1 part of catalyst n, N '-dimethyl cyclohexylamine, 0.5
Part catalyst TMR-2 and 0.4 part of water；
The preparation method of the combined polyether includes the following steps: said combination polyethers raw material stainless steel mixing kettle is added
It is interior, it is stirred 1 hour under the conditions of 25 DEG C with the revolving speed of 500r/min, blowing is up to use for hard bubble of polyurethane combined polyether.
Effect example 1
Examples 1 to 3 and 1 resulting materials of comparative example are placed in the conventional heating equipment of this field and are warming up to 200 DEG C, and
20min is kept the temperature at this temperature, measures its thermal weight loss ratio, acquired results such as following table.
1 Examples 1 to 3 of table and 1 weightlessness of comparative example are than test result summary sheet
| Detection project | Weightless ratio |
| Embodiment 1 | 1.5 |
| Embodiment 2 | 3.2 |
| Embodiment 3 | 6.1 |
| Comparative example 1 | 43.8 |
As can be seen from the above table, present invention gained high-temperature resistant hard polyurethane foams are relative to using conventional MDI made
The hard polyurethane foams obtained, high temperature resistance more preferably, can be used for a long time under 200 DEG C of environment.
Claims (11)
1. a kind of preparation method of modified MDI, which is characterized in that itself the following steps are included: isocyanates is warming up to 120~
140 DEG C, acid anhydrides and epoxide are sequentially added, reaction is until when-NCO content is 15~25%；
Wherein, the dosage of the isocyanates is calculated by weight as 2541~7536 parts, and the viscosity of the isocyanates is
200mPas, the isocyanates-NCO content be 30.5-32%；
The dosage of the acid anhydrides is calculated by weight as 96~480 parts, and the acid anhydrides is phthalic anhydride, maleic anhydride, second
One of acid anhydrides and trimellitic anhydride；
The dosage of the epoxide is calculated by weight as 170~850 parts；
The dosage molar ratio of the acid anhydrides and the epoxide is 1:5~5:1；
Wherein the isocyanates is the modifier of pure MDI, polymeric MDI or pure MDI and polymeric MDI.
2. preparation method as described in claim 1, which is characterized in that the isocyanates is the isocyanic acid of trade mark PM-200
Ester.
3. preparation method as described in claim 1, which is characterized in that the acid anhydrides is trimellitic anhydride；
3~8 additions of the acid anhydrides point.
4. preparation method as described in claim 1, which is characterized in that the epoxide is bisphenol A diglycidyl ether
Or ethylene glycol diglycidylether；
3~8 additions of the epoxide point.
5. a kind of as the modification MDI as obtained by Claims 1 to 4 described in any item preparation methods.
6. a kind of preparation method of polyurethane foam, which is characterized in that it is the following steps are included: by combined polyether and modified MDI
It is uniformly mixed post curing；
Wherein, the modified MDI is as obtained by the described in any item preparation methods of Claims 1 to 4；
The mass parts ratio of the combined polyether and the modified MDI are 1:2~1:1；
The temperature of the curing is 40~60 DEG C, and the time of the curing is 5~15min.
7. preparation method as claimed in claim 6, which is characterized in that the raw material of the combined polyether wraps according to parts by weight
It includes: 70 parts of polyether polyol A, 20 parts of polyether polyol B, 10 parts of polyether polyol C, 2 parts of foam stabilisers, 1.5~2 parts of catalysis
Agent and 0.4 part of water；
The polyether polyol A is degree of functionality 4~5, and hydroxyl value is 435~465mgKOH/g, viscosity 2000 at 25 DEG C~
4000mPas, moisture content are less than the polyether polyol of 0.1wt%；
The polyether polyol B is degree of functionality 3, and hydroxyl value is 330~350mgKOH/g, 200~400mPas of viscosity at 25 DEG C,
Moisture content is less than the polyether polyol of 0.1wt%；
The polyether polyol C is degree of functionality 2, and hydroxyl value is 270~290mgKOH/g, 60~80mPas of viscosity at 25 DEG C, water
The polyether polyol for dividing content to be less than 0.1wt%；
The foam stabiliser is the foam stabiliser of trade mark B-8545；
The catalyst is amines catalyst or organo-metallic catalyst；
The water is deionized water.
8. preparation method as claimed in claim 7, which is characterized in that the polyether polyol A is that the polyethers of the trade mark 4110 is more
First alcohol；
The polyether polyol B is the polyether polyol of the trade mark 305；
The polyether polyol C is the polyether polyol of the trade mark 204；
The catalyst is tertiary amine catalyst.
9. preparation method as claimed in claim 7, which is characterized in that the catalyst is to contain N, N '-dimethyl cyclohexylamine
With the composite catalyst of quaternary ammonium salt catalyst TMR-2, the N, N '-dimethyl cyclohexylamine and the quaternary ammonium salt catalyst TMR-2
Mass ratio be 1:1~2:1.
10. preparation method as claimed in claim 7, which is characterized in that the preparation method of the combined polyether includes following step
It is rapid: the raw material of the combined polyether to be mixed, stirring；
Wherein, the whipping temp of the stirring is 15~30 DEG C, and the stirring rate of the stirring is 400~600r/min, described
The mixing time of stirring is 0.8~1.2h.
11. preparation method as claimed in claim 6, which is characterized in that the temperature of the curing is 45 DEG C；
The time of the curing is 10min.
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| CN110563913A (en) * | 2019-08-30 | 2019-12-13 | 山东一诺威聚氨酯股份有限公司 | High heat-resistant thermoplastic polyurethane elastomer and preparation method thereof |
| CN113980223B (en) * | 2021-12-15 | 2023-03-31 | 上海东大聚氨酯有限公司 | Combined polyether for ultra-low-density, ultra-low-conductivity and ultra-fast-demoulding model refrigerator, heat-insulating material and preparation method of combined polyether |
| TWI841462B (en) * | 2023-07-28 | 2024-05-01 | 黑木股份有限公司 | Modified polyurethane material and method for manufacturing the same |
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