CN115044005A - Foaming material prepared by adopting environment-friendly amine catalyst - Google Patents
Foaming material prepared by adopting environment-friendly amine catalyst Download PDFInfo
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- CN115044005A CN115044005A CN202210775467.8A CN202210775467A CN115044005A CN 115044005 A CN115044005 A CN 115044005A CN 202210775467 A CN202210775467 A CN 202210775467A CN 115044005 A CN115044005 A CN 115044005A
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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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/1833—Catalysts containing secondary or tertiary amines or salts thereof having ether, acetal, or orthoester groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
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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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
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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
- C08G18/28—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
- C08G18/4833—Polyethers containing oxyethylene units
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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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
- C08G18/6677—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203 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
- C08G2101/00—Manufacture of cellular products
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention discloses a foaming material prepared by adopting an environment-friendly amine catalyst, wherein the environment-friendly amine catalyst is 2- [ [2- [2- (dimethylamino) ethoxyethyl ] methylamino ] -ethanol, the catalyst is a polyurethane foaming catalyst with high-efficiency reactivity and small smell, has low emission and a very wide processing technology, and is used for preparing the foaming material.
Description
Technical Field
The invention relates to the technical field of polyurethane material preparation, in particular to a foaming material prepared by adopting an environment-friendly amine catalyst.
Background
Polyurethane foam is prepared by polymerizing and foaming isocyanate and hydroxyl compound, and can be divided into soft and hard according to the hardness, wherein the soft is the main variety. In general, it has excellent elasticity, softness, elongation and compressive strength; good chemical stability and resistance to many solvents
And oils; the wear resistance is excellent and is 20 times larger than that of natural sponge; and also has excellent processability, heat insulation property, adhesiveness and the like, and is a cushioning material with excellent performance. The reaction is complex in the preparation process of polyurethane, and the materials used need to be added with other auxiliary agents such as amine catalysts, tin catalysts, cell opening agents, crosslinking agents and the like besides the main reaction raw materials such as organic isocyanate, polyol and the like.
The performance of polyurethane is influenced by the technological parameters of milky white time, gel time, debonding time and the like in the preparation process. The amine catalyst can adjust the process parameters, improve the processing process of polyurethane, and influence the structure of the polyurethane, thereby improving the service performance of the material. In different polyurethane systems, suitable amine catalysts are often different, and for a specific amine catalyst, an optimal application scenario also exists. From the viewpoint of molecular structure, common amine catalysts are mainly classified into tertiary amines, ether amines and alcohol amines.
CN112029133A discloses a polyurethane foam material and a preparation method thereof, wherein the polyurethane foam material is prepared by taking 10-90 parts by mass of a thermoplastic polyurethane elastomer as a framework material, reacting with 10-90 parts by mass of isocyanate-terminated polyurethane, water, a catalyst and a selectively added functional auxiliary agent for foaming, and extruding; the mass ratio of water to isocyanate-terminated polyurethane is 0.1-10%; the mass ratio of the catalyst to the isocyanate-terminated polyurethane is 0.1-3%; the mass ratio of the functional additive to the polyurethane foaming material is 0-10%; the isocyanate content of the isocyanate-terminated polyurethane is 1 to 25 weight percent. The polyurethane foam material has the characteristics of simple production process, low density, high/low temperature resistance, extremely low VOC (volatile organic compounds), extremely low compression deformation and the like, and can have better application prospects in the fields of sealing, shock absorption, weight reduction, shoe materials and the like. However, the catalyst used in the invention is a small molecular product which is easy to emit, has offensive amine odor, and can continuously migrate out in the construction process or from a foam finished product, thereby causing harm to human health.
Disclosure of Invention
In view of the above-mentioned drawbacks of the prior art, the technical problem to be solved by the present invention is to provide an environmentally friendly amine catalyst with low emission, and to use the amine catalyst in the preparation of foam materials.
In order to achieve the purpose, the invention provides a foaming material prepared by adopting an environment-friendly low-emission amine catalyst, the low-emission amine catalyst is an efficient low-odor reactive polyurethane foaming catalyst, has low emission and a wide processing technology, and the prepared polyurethane foaming material has the characteristics of low emission of organic volatile matters and odor reduction.
In order to achieve the purpose of the invention, the invention adopts the following technical scheme:
a foaming material prepared by adopting an environment-friendly amine catalyst comprises the following components: isocyanate, polyether polyol, a foaming agent, an amine catalyst, a chain extender, a cross-linking agent, a foam stabilizer and a surfactant.
Preferably, the foaming material prepared by adopting the environment-friendly amine catalyst comprises the following components in parts by mass: 60-120 parts of isocyanate, 80-120 parts of polyether polyol, 1-5 parts of foaming agent, 1-6 parts of amine catalyst, 3-10 parts of chain extender, 1-3 parts of cross-linking agent, 1-3 parts of foam stabilizer and 2-8 parts of surfactant.
Preferably, the isocyanate is one or a mixture of two or more of toluene diisocyanate, diphenylmethane diisocyanate, and polymethylene polyphenyl polyisocyanate.
Preferably, the foaming agent is one of trifluoroiodomethane and 1,1,1,3, 3-pentafluoropropane.
Preferably, the amine catalyst is 2- [ [2- [2- (dimethylamino) ethoxyethyl ] methylamino ] -ethanol, and the catalyst is prepared by taking dimethylamine, dichloroethane and N-methyldiethanolamine as raw materials and tetramethylethylenediamine as an acid-binding agent.
Further preferably, the preparation method of the 2- [ [2- [2- (dimethylamino) ethoxyethyl ] methylamino ] -ethanol comprises the following steps:
(1) in N 2 Under the atmosphere, adding 50-150g of 30-35 wt% dimethylamine aqueous solution, 200-400g dichloroethane and 60-100g of tetramethylethylenediamine into a high-pressure reaction kettle, stirring and mixing uniformly, raising the temperature of a reaction system to 30-80 ℃, and keeping the system pressure at 1-2 MPa; reacting for 4-6 h; cooling to the temperature after the reaction is finishedRoom temperature; layering the reaction solution; distilling the organic layer under normal pressure and reduced pressure; collecting the fraction N, N-dimethyl ammonium chloride at the temperature of 55-65 ℃;
(2) mixing 8-12g N N-dimethylammonium chloride, 30-38g N-methyldiethanolamine, 10-13g tetramethylethylenediamine and 60-100mL toluene, heating to 120 ℃ at 100 ℃, reacting for 4-6h, and naturally cooling to room temperature; filtering, collecting filtrate, carrying out reduced pressure rectification on the filtrate, and collecting the fraction at 160-170 ℃, namely 2- [ [2- [2- (dimethylamino) ethoxyethyl ] methylamino ] -ethanol.
2- [ [2- [2- (dimethylamino) ethoxyethyl group]Methylamino radical]Ethanol, ZF-10 for short, is a high-efficiency, low-odor, reactive polyurethane foaming catalyst, has low emission and wide processing technology, is commonly used for preparing polyether polyurethane soft foams, molded foams, packaging hard foams and the like, and can be fixed in a polyurethane molecule in a chemical bond form due to the fact that the catalyst contains reactive groups (hydroxyl, amino and the like) which react with isocyanate so as to inhibit volatilization of amine. However, the currently reported process for preparing ZF-10 by using N, N-di -ethanolamine and N-methyldiethanolamine as raw materials through steps of chlorination, condensation and the like has the following problems: (1) production of large amounts of SO from N, N-dimethylethanolamine by thionyl chloride 2 (ii) a (2) The preparation of the sodium monoalcohol by the N-methyldiethanolamine consumes equivalent sodium hydroxide and the sodium monoalcohol is not easy to preserve; (3) the condensation reaction of the sodium monoalcohol and the N, N-di chloroethyl amine generates a large amount of sodium chloride solid waste, and the treatment is difficult.
The preparation of ZF-10 is bimolecular nucleophilic substitution reaction, during the reaction process, a pair of lone-pair electrons are actually carried with affinity to attack electron-deficient central atoms with electrophilicity, a leaving group leaves at the same time of forming a transition state, and carbonium ions are not generated in the reaction; in addition, the organic alkali replaces the traditional sodium hydroxide acid-binding agent, so that the generation of sodium chloride is avoided, the emission of solid waste is reduced, and the green chemical concept is met.
Preferably, the chain extender is one or more of ethylene glycol, 1, 3-propylene glycol and pentanediol.
Preferably, the cross-linking agent is 2, 2-dimethylolbutanol.
Preferably, the foam stabilizer is a modified silicone polyether emulsion.
Preferably, the surfactant is a silicone oil.
The preparation method of the foaming material prepared by adopting the environment-friendly amine catalyst comprises the following steps:
s1, weighing the raw materials according to the formula, mixing polyether polyol, amine catalyst, surfactant, chain extender and cross linker, and stirring for 20-50min at 50-60 ℃ and at 600-800 r/min; adding 1/3-1/2 foaming agent, and continuously stirring for 20-30min to obtain a mixture 1;
s2 mixing isocyanate and foam stabilizer, stirring at 60-70 deg.C and 300-400rpm for 20-30 min; then adding the rest foaming agent and continuously stirring for 10-20min to obtain a mixture 2;
s3, mixing the mixture 1 and the mixture 2 through a gun head, injecting the mixture into a foaming target cavity for foaming, and curing to obtain the foaming material prepared by the environment-friendly amine catalyst.
Compared with the prior art, the invention has the following beneficial effects:
the foaming material prepared by adding the high-efficiency low-emission reactive polyurethane foaming catalyst 2- [ [2- [2- (dimethylamino) ethoxyethyl ] methylamino ] -ethanol has the characteristics of excellent physical property, low emission of volatile organic compounds, low odor and the like, and can meet the environmental protection requirement in the world at present; compared with the traditional preparation process of 2- [ [2- [2- (dimethylamino) ethoxyethyl ] methylamino ] -ethanol, the preparation method of the invention does not need to prepare pure sodium salt with extremely strong activity, and solves the problem that alkoxide is not easy to store; in addition, the organic alkali replaces the traditional sodium hydroxide acid-binding agent, so that the generation of sodium chloride is avoided, the emission of solid waste is reduced, and the green chemical concept is met.
Detailed Description
The present invention will be described in further detail with reference to the following specific examples. The procedures, conditions, experimental methods and the like for carrying out the present invention are common knowledge and common general knowledge in the art except for the contents specifically mentioned below, and the present invention is not particularly limited.
The invention uses part of raw materials with the following sources:
polypropylene glycol with hydroxyl value of 51-62mgKOH/g, acid value less than or equal to 0.5mgKOH/g, water content less than or equal to 0.5%, Shandong Changyao new materials Co.
Silicone oil, model DC-193, was manufactured by Queen chemical Co., Ltd.
The modified silicone resin polyether emulsion contains 55% of polyether, and is produced by Jining biruey-Yi chemical Co.
Example 1
The preparation method of the foam material prepared by adopting the environment-friendly amine catalyst comprises the following steps:
s1 mixing 100g polypropylene glycol, 5g 2- [ [2- [2- (dimethylamino) ethoxyethyl ] methylamino ] -ethanol, 3g silicone oil, 5g pentanediol, 2g2, 2-dimethylolbutanol, and stirring at 50 deg.C and 700r/min for 30 min; adding 2g of trifluoroiodomethane, and continuously stirring for 20min to obtain a mixture 1;
s2, mixing 80g of diphenylmethane diisocyanate and 2g of modified silicone resin polyether emulsion, and stirring at 60 ℃ and 400rpm for 25 min; then adding 2g of trifluoroiodomethane, and continuously stirring for 15min to obtain a mixture 2;
s3, mixing the mixture 1 and the mixture 2 through a gun head, injecting the mixture into a foaming target cavity for foaming, and curing to obtain the foaming material prepared by the environment-friendly amine catalyst.
The preparation method of the 2- [ [2- [2- (dimethylamino) ethoxyethyl ] methylamino ] -ethanol comprises the following steps:
(1) in N 2 Under the atmosphere, 86.56g of 30-35 wt% dimethylamine aqueous solution, 248.5g of dichloroethane and 76.35g of tetramethylethylenediamine are added into a high-pressure reaction kettle and stirred and mixed uniformly, the temperature of a reaction system is raised to 35 ℃, and the pressure of the system is kept at 1.5 MPa; reacting for 5 hours; cooling to room temperature after the reaction is finished; layering the reaction solution; distilling the organic layer under normal pressure and reduced pressure; collecting the fraction N, N-dimethyl ammonium chloride at 60 ℃;
(2) mixing 10.75g N N-dimethyl ammonium chloride, 35.7g N-methyl diethanolamine, 12.76g tetramethyl ethylenediamine and 80mL toluene, heating to 110 ℃, reacting for 5h, and naturally cooling to room temperature; filtering, collecting filtrate, rectifying the filtrate under reduced pressure, and collecting 165 deg.C fraction which is 2- [ [2- [2- (dimethylamino) ethoxyethyl ] methylamino ] -ethanol.
Comparative example 1
A preparation method of a foaming material prepared by adopting an amine catalyst comprises the following steps:
s1 mixing 100g polypropylene glycol, 5g triethylene imine, 3g silicone oil, 5g pentanediol, 2g2, 2-dimethylol butanol, stirring at 50 deg.C and 700r/min for 30 min; adding 2g of trifluoroiodomethane, and continuously stirring for 20min to obtain a mixture 1;
s2, mixing 80g of diphenylmethane diisocyanate and 2g of modified silicone resin polyether emulsion, and stirring at 60 ℃ and 400rpm for 25 min; then adding 2g of trifluoroiodomethane, and continuously stirring for 15min to obtain a mixture 2;
s3, mixing the mixture 1 and the mixture 2 through a gun head, injecting the mixture into a foaming target cavity for foaming, and curing to obtain the foaming material prepared by the amine catalyst.
Test example 1
Odor and VOC testing:
the foams obtained in example 1 and comparative example 1 were tested according to the method PV3900-2000, odor test for parts of the interior of automobiles, with the rating given in Table 1:
TABLE 1 Scoring level Table
5 persons evaluate the foam material, and the average value is obtained, and the experimental result shows that the foam material prepared in the example 1 is scored for 2.2 points; the foam obtained in comparative example 1 scored 3.8, which is probably due to the fact that the environmentally friendly amine catalyst 2- [ [2- [2- (dimethylamino) ethoxyethyl ] methylamino ] -ethanol added in example 1 had a lower emission than the common amine catalyst triethyleneimine used in comparative example 1.
Test example 2
And (3) testing the rebound rate:
according to GB/T6670-2008 'determination of rebound resilience by falling ball method for soft foam polymer material', the foam materials prepared in example 1 and comparative example 1 are cut into 100mm × 100mm × 50mm, and then placed on a foam rebound coefficient determinator, a steel ball with diameter of 16mm and mass of 17.0g is freely dropped onto the surface of a sample from a fixed height of 500mm, the height H (unit is mm) of the sigh of the steel ball is measured, and the rebound ratio R is calculated according to the following formula:
R＝H/500×100％
the test results are shown in table 2:
TABLE 2 rebound resilience test results for foamed materials
| Rebound resilience (%) | |
| Example 1 | 63.8 |
| Comparative example 1 | 52.4 |
The experimental results in table 2 show that the foaming material prepared in example 1 has better resilience, and the possible reason is that the reactive amine catalyst 2- [ [2- [2- (dimethylamino) ethoxyethyl ] methylamino ] -ethanol used in example 1 can be fixed in the form of chemical bond in the polyurethane molecule, and can be better crosslinked with the polyurethane molecule, and the dense crosslinking structure improves the mechanical property of the foaming material, so that the resilience is better.
Claims (10)
1. The foaming material prepared by adopting the environment-friendly amine catalyst is characterized by comprising the following components: isocyanate, polyether polyol, a foaming agent, an amine catalyst, a chain extender, a cross-linking agent, a foam stabilizer and a surfactant.
2. The foam material prepared by adopting the environment-friendly amine catalyst as claimed in claim 1, which is characterized by comprising the following components in parts by mass: 60-120 parts of isocyanate, 80-120 parts of polyether polyol, 1-5 parts of foaming agent, 1-6 parts of amine catalyst, 3-10 parts of chain extender, 1-3 parts of cross-linking agent, 1-3 parts of foam stabilizer and 2-8 parts of surfactant.
3. The foam material prepared by the environment-friendly amine catalyst as claimed in claim 1 or 2, wherein: the isocyanate is one or a mixture of more than two of toluene diisocyanate, diphenylmethane diisocyanate and polymethylene polyphenyl polyisocyanate.
4. The foam material prepared by the environment-friendly amine catalyst as claimed in claim 1 or 2, wherein: the foaming agent is one of trifluoroiodomethane and 1,1,1,3, 3-pentafluoropropane.
5. The foam material prepared by the environment-friendly amine catalyst as claimed in claim 1 or 2, wherein: the amine catalyst is 2- [ [2- [2- (dimethylamino) ethoxy ethyl ] methylamino ] -ethanol, and is prepared by taking dimethylamine, dichloroethane and N-methyldiethanolamine as raw materials and tetramethylethylenediamine as an acid-binding agent.
6. The foam material prepared by the environment-friendly amine catalyst as claimed in claim 5, wherein: the preparation method of the 2- [ [2- [2- (dimethylamino) ethoxyethyl ] methylamino ] -ethanol comprises the following steps:
(1) in N 2 Stirring and mixing 50-150g of 30-35 wt% dimethylamine aqueous solution, 200-400g dichloroethane and 60-100g of tetramethylethylenediamine under the atmosphereMixing uniformly, raising the temperature of a reaction system to 30-80 ℃, and keeping the pressure of the system at 1-2 MPa; reacting for 4-6 h; cooling to room temperature after the reaction is finished; layering the reaction solution; distilling the organic layer under normal pressure and reduced pressure; collecting the fraction N, N-dimethyl ammonium chloride at the temperature of 55-65 ℃;
(2) mixing 8-12g N N-dimethylammonium chloride, 30-38g N-methyldiethanolamine, 10-13g tetramethylethylenediamine and 60-100mL toluene, heating to 120 ℃ at 100 ℃, reacting for 4-6h, and naturally cooling to room temperature; filtering, collecting filtrate, carrying out reduced pressure rectification on the filtrate, and collecting the fraction at 160-170 ℃, namely 2- [ [2- [2- (dimethylamino) ethoxyethyl ] methylamino ] -ethanol.
7. The foam material prepared by the environment-friendly amine catalyst as claimed in claim 1 or 2, wherein: the chain extender is one or more of ethylene glycol, 1, 3-propylene glycol and pentanediol.
8. The foam material prepared by the environment-friendly amine catalyst as claimed in claim 1 or 2, wherein: the cross-linking agent is 2, 2-dimethylolbutanol.
9. The foam material prepared by the environment-friendly amine catalyst as claimed in claim 1 or 2, wherein: the surfactant is silicone oil.
10. The method for preparing the foam material prepared by adopting the environment-friendly amine catalyst according to any one of claims 1 to 9, which comprises the following steps:
s1, weighing the raw materials according to the formula, mixing polyether polyol, amine catalyst, surfactant, chain extender and cross-linking agent, and stirring for 20-50min at 50-60 ℃ and at 600-800 r/min; adding foaming agent with the mass of 1/3-1/2, and continuously stirring for 20-30min to obtain a mixture 1;
s2 mixing isocyanate and foam stabilizer, stirring at 60-70 deg.C and 300-400rpm for 20-30 min; then adding the rest foaming agent and continuously stirring for 10-20min to obtain a mixture 2;
s3, mixing the mixture 1 and the mixture 2 through a gun head, injecting the mixture into a foaming target cavity for foaming, and curing to obtain the foaming material prepared by the environment-friendly amine catalyst.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104341313A (en) * | 2013-08-02 | 2015-02-11 | 史小鸣 | Synthesis of N,N,N'-trimethyl-N'-hydroxyethyl diethyl ether |
| CN111393833A (en) * | 2020-04-02 | 2020-07-10 | 张家港长泰汽车饰件材料有限公司 | High-opening-rate hydrolysis-resistant polyurethane foam and preparation method and application thereof |
-
2022
- 2022-07-01 CN CN202210775467.8A patent/CN115044005A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104341313A (en) * | 2013-08-02 | 2015-02-11 | 史小鸣 | Synthesis of N,N,N'-trimethyl-N'-hydroxyethyl diethyl ether |
| CN111393833A (en) * | 2020-04-02 | 2020-07-10 | 张家港长泰汽车饰件材料有限公司 | High-opening-rate hydrolysis-resistant polyurethane foam and preparation method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| 林友文 等: "《有机化学》", vol. 1, 中国医药科技出版社, pages: 86 - 89 * |
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