CN106589373A - Super-hydrophobic polyimide foam and production method thereof - Google Patents
Super-hydrophobic polyimide foam and production method thereof Download PDFInfo
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- CN106589373A CN106589373A CN201611126780.XA CN201611126780A CN106589373A CN 106589373 A CN106589373 A CN 106589373A CN 201611126780 A CN201611126780 A CN 201611126780A CN 106589373 A CN106589373 A CN 106589373A
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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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
- C08G73/106—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing silicon
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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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1035—Preparatory processes from tetracarboxylic acids or derivatives and diisocyanates
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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 relates to a super-hydrophobic polyimide foam and a production method thereof, and belongs to the technical field of polymeric materials. The super-hydrophobic polyimide foam comprises, by mass, 80-120 parts of aromatic dianhydride, 20-90 parts of a polar solvent, 5-100 parts of hydrosilicone oil, 5-20 parts of low molecular alcohol, 5-20 parts of polyether modified silicone oil, 5-10 parts of a catalyst and 150-300 parts of polyisocyanate. Compared with polyimide foams in the prior art, the super-hydrophobic polyimide foam has the advantages of excellent hydrophobicity, good heat resistance, good stability and good flame retardation property; and the method has the advantages of simple process flow, and facilitation of industrial production and promotion.
Description
Technical field
The present invention relates to a kind of super-hydrophobic polyimide foam and preparation method thereof, belongs to technical field of polymer materials.
Background technology
Polyimide foam because of its excellent fire resistance, heat-insulating property, sound insulation value, low-smoke low-toxicity performance, in the world
On be widely used for naval vessel, aircraft carrier, submarine, aircraft as exhausted heat-insulated and deadener.
NCO polyimide foam is sent out in the presence of a catalyst by aromatic dianhydride or aromatic esters
Raw polycondensation reaction, using the low-molecular material for producing, such as carbon dioxide, as a kind of Thermocurable polyimide bubble obtained in foaming agent
Foam plastics.Due to adopting room temperature free foaming in technical process, and the purity requirement to raw material is relatively low therefore with very
Obvious industrialized production advantage.
As heat-barrier material, if its water suction, can greatly improve heat conductivity, effect of heat insulation is reduced, lose heat-insulated material
The effect of material.The water absorption rate of NCO polyimide foam is very low, but water can also be penetrated in foam, one
Its using effect is also affected to a certain extent under a little special environments.So, improve its hydrophobicity promoting the use of for the material
It is significant.
The content of the invention
In order to solve foregoing problems, the present invention provides a kind of super-hydrophobic polyimide foam and preparation method thereof.
Super-hydrophobic polyimide foam in the present invention includes the component of following mass fraction：Aromatic dianhydride 80-120 part,
Polar solvent 20-90 parts, containing hydrogen silicone oil 5-100 parts, low mass molecule alcohol 5-20 parts, polyether modified silicon oil 5-20 parts, catalyst 5-10
Part, polyisocyanates 150-300 parts.
The aromatic dianhydride is pyromellitic acid dianhydride, 3,3 ', 4,4 '-benzophenone tetracarboxylic dianhydride, 3,3 ', 4,4 '-biphenyl
Base tetracarboxylic dianhydride, 3,3 ', 4,4 '-benzophenone tetracarboxylic dianhydride, 3,3 ', 4,4 '-diphenyl sulphone (DPS) tetracarboxylic dianhydride, 3,3 ', 4,
One or more in 4 '-oxydiphthalic.
The polar solvent be N, N '-dimethyl Methanamide, N, N '-dimethyl acetamide, METHYLPYRROLIDONE,
In dimethyl sulfoxide, tetrahydrofuran one or more.
The containing hydrogen silicone oil, hydrogen content is 0.01-1.6%.In the Si -- H bond of containing hydrogen silicone oil active hydrogen can and isocyanates
In-NCO group reacts in the presence of catalyst, forms Si-C keys, and poly dimethyl silicon is introduced in polyimide molecule chain
Oxygen alkane side chain, gives the ultra-hydrophobicity of product.
The polyether modified silicon oil is one or two in SiOC types silicone oil or SiC type silicone oil as foam stabiliser
Combination, play a part of it is even bubble and stable foam, allow product abscess evenly with it is fine and closely woven.
The catalyst is the one kind or several in triethanolamine, triethylenediamine, stannous octoate, the fourth stannum of dilaurate two
Kind.
The polyisocyanates is polyphenyl polymethylene polyisocyanates, xylene diisocyanate or toluene
One or more of diisocyanate.
The preparation process of the super-hydrophobic polyimide foam in the present invention is as follows：（1）Aromatic dianhydride is molten in reactor
In polar solvent, low mass molecule alcohol is then proportionally added into, is heated to 80-120 DEG C of reaction 1-2 hour, be then cooled to room temperature,
It is proportionally added into containing hydrogen silicone oil, catalyst, polyether modified silicon oil successively again, stirs, obtains foam precursors；（2）By foam
Precursor is uniform by stirring or high-pressure atomization collisional mixing with polyisocyanates, pours foaming in mould into and obtains in the middle of foam
Body；（3）Foam intermediate is placed in microwave oven, with microwave heating 0.5-2 hours so as to further solidification, then by foam
It is placed in infrared baking oven and is heated to 150-300 DEG C, after 0.5-2 hours finished product is obtained.
The invention provides a kind of super-hydrophobic polyimide foam and preparation method thereof, compared with prior art, this
The containing hydrogen silicone oil that introduces in formula of bright novelty participates in chemical reaction, because the Si-H in containing hydrogen silicone oil strand contains vivaciously
Hydrogen, can in the presence of catalyst with isocyanates in-NCO group reacted, so as in polyimide foam molecule
The side chain of longer polydimethylsiloxane is introduced in chain, super-hydrophobic group is formed, the super-hydrophobicity of product is given, is absorbed water under room temperature
Rate can be less than 0.30%.Hydrophobic performance of the present invention is excellent, and thermostability, stability, anti-flammability are all preferable, while technological process is simple,
Be conducive to industrialized production and popularization.
Specific embodiment
Technical scheme is described in detail with reference to embodiment.
Embodiment 1.
（1）By mass fraction, 100 parts of pyromellitic acid dianhydrides are dissolved in into 80 parts of polar solvent N, N- dimethyl in reactor
In Methanamide, be subsequently adding 10 parts of ethylene glycol, be heated to 110 DEG C and react 1.5 hours, be then cooled to room temperature, then press successively than
Example adds containing hydrogen silicone oil, 10 parts of triethylenediamine catalyst, 5 parts of SiC type polyether modified silicon oils of 5 parts of hydrogen contents 0.2%, stirs
Mix uniform, obtain foam precursors.
（2）Obtained foam precursors and many methyl polyisocyanates of phenyl more than 160 parts are stirred by paddle mixer
Mix homogeneously, pours foaming in mould into and obtains foam intermediate.
（3）Foam intermediate is placed in microwave oven, with microwave heating 1 hour so as to further solidification.Then by foam
It is placed in infrared baking oven and is heated to 250 DEG C, after 2 hours finished product is obtained.
Obtained foam density is 10kg/m3, with super-hydrophobicity, water absorption rate is less than 0.30% under room temperature.
Embodiment 2.
（1）By mass fraction, 100 parts of pyromellitic acid dianhydrides are dissolved in into 80 parts of polar solvent N, N- dimethyl in reactor
In Methanamide, be subsequently adding 10 parts of ethylene glycol, be heated to 110 DEG C and react 1.5 hours, be then cooled to room temperature, then press successively than
Example adds containing hydrogen silicone oil, 10 parts of triethylenediamine catalyst, 5 parts of SiC type polyether modified silicon oils of 30 parts of hydrogen contents 0.2%, stirs
Mix uniform, obtain foam precursors.
（2）Obtained foam precursors and many methyl polyisocyanates of phenyl more than 160 parts are stirred by paddle mixer
Mix homogeneously, pours foaming in mould into and obtains foam intermediate.
（3）Foam intermediate is placed in microwave oven, with microwave heating 1 hour so as to further solidification.Then by foam
It is placed in infrared baking oven and is heated to 250 DEG C, after 2 hours finished product is obtained.
Obtained foam density is 10kg/m3, with super-hydrophobicity, water absorption rate is less than 0.25% under room temperature.
Embodiment 3.
（1）By mass fraction, by 80 part 3,3 ', 4,4 '-benzophenone tetracarboxylic dianhydride is dissolved in 20 parts of polarity in reactor
In Solvents N-methyl -2-Pyrrolidone, 5 parts of ethylene glycol are subsequently adding, are heated to 110 DEG C and react 1.5 hours, be then cooled to room
Temperature, then be proportionally added into the containing hydrogen silicone oil of 40 parts of hydrogen contents 0.8%, 5 parts of triethylenediamine catalyst, 5 parts of SiC types successively and gather
Ether modified silicon oil, stirs, and obtains foam precursors.
（2）Obtained foam precursors and many methyl polyisocyanates of phenyl more than 150 parts are stirred by paddle mixer
Mix homogeneously, pours foaming in mould into and obtains foam intermediate.
（3）Foam intermediate is placed in microwave oven, with microwave heating 1 hour so as to further solidification.Then by foam
It is placed in infrared baking oven and is heated to 250 DEG C, after 2 hours finished product is obtained.Obtained foam density is 15kg/m3, with super thin
Aqueouss, water absorption rate is less than 0.16% under room temperature.
Embodiment 4.
（1）By mass fraction, by 120 parts equal 3,3 ', 4,4 '-oxydiphthalic is dissolved in 90 parts of polarity in reactor
In solvent DMF, 20 parts of ethylene glycol are subsequently adding, are heated to 110 DEG C and react 1.5 hours, be then cooled to room
Temperature, then the containing hydrogen silicone oil of 20 parts of hydrogen contents 1.6%, 10 parts of triethylenediamine catalyst, 20 parts of SiOC types are proportionally added into successively
Polyether modified silicon oil, stirs, and obtains foam precursors.
（2）Obtained foam precursors and many methyl polyisocyanates of phenyl more than 300 parts are stirred by paddle mixer
Mix homogeneously, pours foaming in mould into and obtains foam intermediate.
（3）Foam intermediate is placed in microwave oven, with microwave heating 1 hour so as to further solidification.Then by foam
It is placed in infrared baking oven and is heated to 250 DEG C, after 2 hours finished product is obtained.Obtained foam density is 8kg/m3, with super-hydrophobic
Property, water absorption rate is less than 0.1% under room temperature.
Embodiment 5.
（1）By mass fraction, by 110 part 3,3 ', 4,4 '-xenyl tetracarboxylic dianhydride is dissolved in 70 parts of polarity in reactor
In solvent DMF, 15 parts of ethylene glycol are subsequently adding, are heated to 110 DEG C and react 1.5 hours, be then cooled to room
Temperature, then the containing hydrogen silicone oil of 100 parts of hydrogen contents 0.18%, 8 parts of triethylenediamine catalyst, 15 parts of SiOC are proportionally added into successively
Type polyether modified silicon oil, stirs, and obtains foam precursors.
（2）Obtained foam precursors and many methyl polyisocyanates of phenyl more than 250 parts are stirred by paddle mixer
Mix homogeneously, pours foaming in mould into and obtains foam intermediate.
（3）Foam intermediate is placed in microwave oven, with microwave heating 1 hour so as to further solidification.Then by foam
It is placed in infrared baking oven and is heated to 250 DEG C, after 2 hours finished product is obtained.
Obtained foam density is 8kg/m3, with super-hydrophobicity, water absorption rate is less than 0.1% under room temperature.
Comparative example.
A kind of hydrophobic type polyimide foam, the component comprising following mass fraction：70 parts of aromatic dianhydride, polar solvent
140 parts of part, 20 parts of low mass molecule alcohol, 15 parts of polyether modified silicon oil, 0.5 part of catalyst, 90 parts of polyisocyanates.
Wherein：Aromatic dianhydride be 3,3 ', 4,4 '-benzophenone tetracarboxylic dianhydride, polar solvent be dimethylformamide, low molecule
Alcohol is ethylene glycol, polyether modified silicon oil is SiOC type polyether modified silicon oils, catalyst is stannous octoate, polyisocyanates is Asia
Methylxylene diisocyanate.
By said components and proportioning, obtained foam density is 9kg/m3, water absorption rate is 2.1% under room temperature.
Can be seen that component of the present invention and proportioning can effectively reduce polyimide foam from the index of comparative example
Water absorption rate, improves its hydrophobic performance.
A kind of super-hydrophobic polyimide foam for being provided the embodiment of the present invention above and preparation method thereof has been carried out in detail
Thin to introduce, specific case used herein is set forth to the principle and embodiment of the present invention, and above example is said
It is bright to be only intended to help and understand the method for the present invention and its core concept；Simultaneously for one of ordinary skill in the art, foundation
The thought of the present invention, will change in specific embodiments and applications, and in sum, this specification content is not
It is interpreted as limitation of the present invention.
Claims (8)
1. a kind of super-hydrophobic polyimide foam, it is characterised in that including the component of following mass fraction：Aromatic dianhydride 80-120
Part, polar solvent 20-90 parts, containing hydrogen silicone oil 5-100 parts, low mass molecule alcohol 5-20 parts, polyether modified silicon oil 5-20 parts, catalyst 5-
10 parts, polyisocyanates 150-300 parts.
2. a kind of super-hydrophobic polyimide foam as claimed in claim 1, it is characterised in that：The aromatic dianhydride is equal benzene four
Acid dianhydride, 3,3 ', 4,4 '-benzophenone tetracarboxylic dianhydride, 3,3 ', 4,4 '-xenyl tetracarboxylic dianhydride, 3,3 ', 4,4 '-hexichol first
One kind or several in ketone tetracarboxylic dianhydride, 3,3 ', 4,4 '-diphenyl sulphone (DPS) tetracarboxylic dianhydride, 3,3 ', 4,4 '-oxydiphthalic
Kind.
3. a kind of super-hydrophobic polyimide foam as claimed in claim 1, it is characterised in that：The polar solvent be N, N '-
Dimethylformamide, N, it is a kind of in N '-dimethyl acetamide, METHYLPYRROLIDONE, dimethyl sulfoxide, tetrahydrofuran or
It is several.
4. a kind of super-hydrophobic polyimide foam as claimed in claim 1, it is characterised in that：The containing hydrogen silicone oil, hydrogen content
For 0.01-1.6%.
5. a kind of super-hydrophobic polyimide foam as claimed in claim 1, it is characterised in that：The polyether modified silicon oil is
One or two in SiOC types silicone oil or SiC type silicone oil.
6. a kind of super-hydrophobic polyimide foam as claimed in claim 1, it is characterised in that：The catalyst is three ethanol
One or more in amine, triethylenediamine, stannous octoate, the fourth stannum of dilaurate two.
7. a kind of super-hydrophobic polyimide foam as claimed in claim 1, it is characterised in that：The polyisocyanates is many benzene
One or more of Quito methylene polyisocyanates, xylene diisocyanate or toluene di-isocyanate(TDI).
8. a kind of preparation method of super-hydrophobic polyimide foam, it is characterised in that preparation process is as follows：（1）Aromatic dianhydride is existed
It is dissolved in reactor in polar solvent, is then proportionally added into low mass molecule alcohol, is heated to 80-120 DEG C of reaction 1-2 hour, then
Room temperature is cooled to, then is proportionally added into containing hydrogen silicone oil, catalyst, polyether modified silicon oil successively, stirred, before obtaining foam
Body；（2）Foam precursors and polyisocyanates are uniform by stirring or high-pressure atomization collisional mixing, pour foaming in mould into
Obtain foam intermediate；（3）Foam intermediate is placed in microwave oven, with microwave heating 0.5-2 hours so as to further solid
Change, then foam is placed in infrared baking oven and is heated to 150-300 DEG C, after 0.5-2 hours finished product is obtained.
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| CN201611126780.XA CN106589373B (en) | 2016-12-09 | 2016-12-09 | A kind of super-hydrophobic polyimide foam and preparation method thereof |
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| CN201611126780.XA CN106589373B (en) | 2016-12-09 | 2016-12-09 | A kind of super-hydrophobic polyimide foam and preparation method thereof |
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| CN106589373B CN106589373B (en) | 2019-03-29 |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108715636A (en) * | 2018-06-12 | 2018-10-30 | 常州天晟新材料股份有限公司 | A kind of halogen-free flameproof Polyimide foams and preparation method thereof |
| CN110229340A (en) * | 2019-06-17 | 2019-09-13 | 中国科学院宁波材料技术与工程研究所 | A kind of polyimide aerogels and preparation method thereof based on silane hydrophobically modified |
| CN112480353A (en) * | 2020-11-30 | 2021-03-12 | 山东一诺威聚氨酯股份有限公司 | Super-oil-resistant heat-resistant TPU material and preparation method thereof |
| CN112574408A (en) * | 2020-11-12 | 2021-03-30 | 南北兄弟药业投资有限公司 | Preparation method of polyimide foam material |
| CN112592454A (en) * | 2020-12-14 | 2021-04-02 | 南京大学 | Amino silicone oil modified polyimide foam material and preparation method thereof |
| CN114316193A (en) * | 2021-11-25 | 2022-04-12 | 江苏德恩医疗器械有限公司 | Slow-resilience sponge, manufacturing process and application |
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| CN104829835A (en) * | 2015-04-22 | 2015-08-12 | 哈尔滨工程大学 | Preparation method of isocyanate-based polyimide foam |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108715636A (en) * | 2018-06-12 | 2018-10-30 | 常州天晟新材料股份有限公司 | A kind of halogen-free flameproof Polyimide foams and preparation method thereof |
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| CN112480353A (en) * | 2020-11-30 | 2021-03-12 | 山东一诺威聚氨酯股份有限公司 | Super-oil-resistant heat-resistant TPU material and preparation method thereof |
| CN112592454A (en) * | 2020-12-14 | 2021-04-02 | 南京大学 | Amino silicone oil modified polyimide foam material and preparation method thereof |
| CN112592454B (en) * | 2020-12-14 | 2021-12-17 | 南京大学 | Amino silicone oil modified polyimide foam material and preparation method thereof |
| CN114316193A (en) * | 2021-11-25 | 2022-04-12 | 江苏德恩医疗器械有限公司 | Slow-resilience sponge, manufacturing process and application |
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| CN106589373B (en) | 2019-03-29 |
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Effective date of registration: 20210624 Address after: 266000 Room 401, unit 1, building 6, Jinding garden, 868 Tong'an Road, Laoshan District, Qingdao City, Shandong Province Patentee after: Qingdao Sixian Chemical Technology Co.,Ltd. Address before: 213012 No.98, Zhidong Road, industrial concentration zone, Zhixi Town, Jintan District, Changzhou City, Jiangsu Province Patentee before: JIANGSU WELLSAFE Co.,Ltd. |