CN115386216A - Polyurethane thermal interface material with double dynamic bonds and preparation method thereof - Google Patents
Polyurethane thermal interface material with double dynamic bonds and preparation method thereof Download PDFInfo
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- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
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Abstract
The invention discloses a polyurethane thermal interface material with double dynamic bonds and a preparation method thereof, and the preparation raw materials of the polyurethane thermal interface material comprise: 8.08-8.74 parts of polyurethane prepolymer, 0-0.86 part (not 0) of Schiff base chain extender containing hydroxyl and imino, 90.0-92.0 parts of heat-conducting filler and 0.06-0.30 part of cross-linking agent, wherein the polyurethane prepolymer is a reaction product of diisocyanate and polyol. The polyurethane thermal interface material containing dynamic chemical bonds is subjected to thermal reversible dissociation in the operation process of a device, so that the modulus of the thermal interface material can be effectively reduced, the thermal interface material is more attached to a chip and a heat sink in a contact manner, the contact thermal resistance is effectively reduced, and the total thermal resistance is further reduced. Meanwhile, the polyurethane resin contains a large amount of polar urethane bonds, so that the polyurethane resin has excellent adhesive property on the surface of a chip or a heat sink.
Description
Technical Field
The invention belongs to the technical field of heat conduction materials, and particularly relates to a polyurethane thermal interface material with double dynamic bonds and a preparation method thereof.
Background
The technology in the fields of new energy automobiles, 5G, artificial intelligence and the like is rapidly developed, the power density of electronic devices is continuously increased, and the heat dissipation becomes a prominent problem. Electronic devices typically have a suitable operating temperature range within which the electronic components can operate in a preferred state. Electronic equipment generates heat in the operation process, and if the heat is not removed in time, the operation temperature is higher, so that the operation speed of electronic components is reduced, the reliability of the components is reduced, the service life of the components is shortened, and the operating characteristics of the electronic components and the operation of the associated equipment are also adversely affected. Based on this, the thermal interface material becomes one of the key heat dissipation materials for electronic devices, power modules, communications, energy storage, and the like, which are applied to the above fields. Thermal Interface Materials (TIMs) are also called Thermal conductive Materials, thermal conductive Interface Materials or Interface Thermal conductive Materials, i.e., micro-voids and pores with uneven surfaces generated when an electronic component is joined or contacted with a substrate or the electronic component are filled to strengthen Interface heat transfer and reduce resistance of heat transfer. As long as the system generates heat and needs to dissipate heat, a thermal interface material is generally needed to improve heat dissipation.
According to different practical applications, there are six main types of TIMs, namely non-adhesive TIMs, including heat-conducting gaskets, heat-conducting pastes, heat-conducting phase-change materials, heat-conducting gels, adhesive heat-conducting adhesives and the like. Among them, polymer-based thermal interface materials using polymers (silicone, polyurethane, epoxy resin, etc.) as dispersion media have the advantages of low density, excellent dielectric properties, low raw material cost, easy processing, etc. At present, the mainstream thermal interface material in the market is an organic silicon heat conduction material, but the organic silicon heat conduction material is easy to separate out low-molecular siloxane, so that a circuit is short-circuited, and conduction is influenced. Therefore, silicone heat-conducting products are not generally used for compact components such as semiconductors. The polyurethane and epoxy resin heat conduction materials can well avoid the problem of low molecular siloxane precipitation of the organic silicon heat conduction materials, but the hardness and viscosity of the materials are very high, and the quantity of the heat conduction fillers added into the materials is limited, so that the improvement of the heat conductivity of the products is limited.
The factors influencing the heat-conducting property of the filled polyurethane composite material mainly comprise two factors: (1) a heat transfer network within the composite; (2) The interface thermal resistance inside the composite material, namely the contact thermal resistance between the filler and the resin and between the filler and the filler. For low-filling-amount polyurethane composite materials, the efficiency of an internal heat transfer network constructed by the filler plays a determining factor for the heat-conducting property of the polyurethane composite materials; for the polyurethane composite material with high filling amount, as the content of the filler is increased, the heat transfer network in the composite material tends to be perfect, so that the contact heat resistance becomes a main factor influencing the heat transfer effect of the composite material. Therefore, the method has important significance for improving the thermal conductivity of the polymer-based thermal interface material and reducing the contact thermal resistance of the thermal interface material. The conventional methods for reducing the thermal contact resistance of the thermal interface material mainly include: (1) increasing contact pressure on the contact surface; (2) reducing surface roughness or increasing surface flatness, etc.
Disclosure of Invention
In order to solve the defects in the prior art, the invention aims to provide a polyurethane thermal interface material with double dynamic bonds and a preparation method thereof.
The chemical bonding and topological structure of the traditional polymer are static, and the topological structure is difficult to change by changing the bonding mode of the main chain structure. And the dynamic covalent bond has lower bond dissociation energy, and the bonding mode is reversible. The polymer material containing dynamic covalent bonds can respond to external signals by adjusting the structure of the polymer material when being subjected to specific external stimuli, however, the modification of the polymer material is limited to single chemical functional group modification at present, so that the topological structure and the form change of the polymer material are very limited. Based on this, the switching of dynamic covalent bonding through dual dynamic covalent bonds such as imine bonds and urethane bonds is designed in polyurethane resin to realize the regulation of high molecular structure performance and the remodeling of topological structure. While the dynamic covalent bonds act as sacrificial bonds for enhancing the energy dissipation capability of the resin.
According to the invention, by introducing double dynamic covalent bonds into a polyurethane resin matrix and utilizing the reversible activity of the dynamic covalent bonds, the polymer-based thermal interface material shows a stimulus-response behavior, namely the dissociation and bonding of cross-linking points, when triggered by an external field, so that the modulus of the polymer-based thermal interface material is influenced, and the thermal contact resistance of the thermal interface material in the heat transfer process is further regulated and controlled. Total thermal resistance (R) of polymer-based thermal interface materials total ) Thermal contact resistance (R) c ) And modulus (G) are shown in FIG. 1, where BLT is the thickness of the thermal interface material, k TIM Is the thermal conductivity, R, of the material contact1 And R contact2 Respectively representing the contact thermal resistances of two surfaces of the thermal interface material in contact with the electronic device; c and n are empirical constants, P is packaging pressure, and sigma represents the surface roughness of the material; lambda [ alpha ] lim R 0 Respectively representing the tensile limit and fracture toughness of the material. The ability of the polyurethane resin to have network topology is provided by utilizing imine linkages and amino groupsDynamic reversible exchange reaction of formate bonds (fig. 2). Under the condition of certain filler content, polyurethane thermal interface materials with different molecular chain lengths are obtained by regulating and controlling the proportion and the content of imine bonds and urethane bonds, and the materials show stimulation-response behaviors, namely, the dissociation and bonding of cross-linking points when triggered by an external field, and the corresponding viscoelasticity is related to the proportion, the content and the molecular chain length of dynamic covalent bonds. The thermal conductivity (thermal conductivity and thermal contact resistance) of the material is regulated and controlled by regulating and controlling the viscoelastic response of the polyurethane thermal interface material, such as modulus, characteristic relaxation time, an energy dissipation mechanism and the like, so that the material has excellent thermal conductivity and low thermal contact resistance.
The specific technical scheme of the invention is as follows:
the invention provides a polyurethane thermal interface material with double dynamic bonds, which comprises the following raw materials in parts by weight:
the polyurethane prepolymer is a reaction product of diisocyanate and polyol.
Further, the diisocyanate is selected from one or more of isophorone diisocyanate, hexamethylene diisocyanate and trimethyl hexamethylene diisocyanate;
the polyalcohol is selected from one or more of polytetrahydrofuran glycol, polyethylene glycol, polypropylene glycol and polybutadiene glycol;
preferably, the diisocyanate is selected from isophorone diisocyanate;
preferably, the polyol is selected from polytetrahydrofuran diol;
preferably, the molecular weight of the polytetrahydrofuran glycol is 2000-3000g/mol, and the mass percentage of the hydroxyl is 0.1% -3.0%.
Further, the preparation method of the polyurethane prepolymer comprises the following steps: adding diisocyanate into the melted polyol, reacting at the temperature of 70.00-90.00 ℃ without solvent or catalyst for 5.00-7.00h, and obtaining a product, namely a polyurethane prepolymer after the reaction is finished;
preferably, the mass ratio of the diisocyanate to the polyol is (3-6): (6-8).
Further, the mass percentage of hydroxyl in the Schiff base chain extender containing hydroxyl and imino is 3-7%;
the Schiff base chain extender containing hydroxyl and imino provides that the molar content of hydroxyl in isocyanate groups provided by the polyurethane prepolymer is 0-75%;
preferably, the hydroxyl-containing schiff base chain extender is
Further, the heat conducting filler is selected from one or more of aluminum oxide, aluminum, zinc oxide, aluminum hydroxide and magnesium hydroxide;
preferably, the particle size of the heat conductive filler is 0.3-15 μm;
preferably, the heat-conducting filler is modified by adopting a silane coupling agent;
preferably, the silane coupling agent is selected from at least one of gamma-aminopropyltriethoxysilane, gamma-glycidoxypropyltrimethoxysilane, gamma-methacryloxypropyltrimethoxysilane, decyltrimethoxysilane, dodecyltrimethoxysilane, and hexadecyltrimethoxysilane.
Further, the specific operation of modifying the heat conductive filler by using a silane coupling agent is as follows: stirring and mixing the heat-conducting filler, the silane coupling agent, the water and the absolute ethyl alcohol at 60-70 ℃, then heating to 130-150 ℃, continuously stirring for 3-4h at the speed of 40-60rpm under the vacuum degree of-90.0 kPa, and cooling to room temperature after the stirring is finished, thus obtaining the heat-conducting silicone oil.
Further, the cross-linking agent is selected from at least one of triethanolamine or glycerol;
preferably, the cross-linking agent is selected from triethanolamine.
Further, the polyurethane thermal interface material also comprises 0-0.005 part of antioxidant;
preferably, the antioxidant is at least one of antioxidant 1010, antioxidant 1076, and antioxidant DLTP.
The invention also provides a preparation method of the polyurethane-based thermal interface material with the double dynamic bonds, which comprises the following steps: according to the mass parts, the polyurethane prepolymer, the Schiff base chain extender containing hydroxyl and imino, the heat-conducting filler and the cross-linking agent are stirred and mixed, and then the stirred and mixed materials are calendered and thermally cured to obtain the polyurethane heat-conducting resin.
Further, stirring for 1-5 min under vacuum at normal temperature;
the temperature of the heat curing is 90-150 ℃, and the curing time is 4-9 h;
preferably, the thermal curing is segmented thermal curing;
preferably, the segmented thermal curing is performed at 90 ℃ for 2h, at 120 ℃ for 3h and at 150 ℃ for 3h;
preferably, an antioxidant is added into the polyurethane prepolymer, the hydroxyl-containing Schiff base chain extender, the heat-conducting filler and the cross-linking agent.
The invention has the beneficial effects that:
the invention utilizes the reversible reaction activity of the dynamic covalent bond, introduces the dynamic covalent bond into the polyurethane resin, and utilizes the adjustment of the network topological structure of the polyurethane resin to regulate and control the hardness of the thermal interface material, thereby regulating and controlling the contact thermal resistance of the thermal interface material in the heat transfer process. The polyurethane thermal interface material containing dynamic chemical bonds is subjected to thermal reversible dissociation in the operation process of a device, so that the modulus of the thermal interface material can be effectively reduced, the thermal interface material is more attached to a chip and a heat sink in a contact manner, the contact thermal resistance is effectively reduced, and the total thermal resistance is further reduced. Meanwhile, the polyurethane resin contains a large amount of polar urethane bonds, so that the polyurethane resin has excellent adhesive property on the surface of a chip or a heat sink.
The invention is very convenient for regulating and controlling the heat-conducting performance parameters of the thermal interface material based on the dual dynamic keys, so that the thermal interface material is also very convenient to apply, can be manufactured into a proper shape through a die cutting process, and meets the fixing and sealing functions so as to be better attached to the surfaces of a chip and a heat sink. Meanwhile, due to the dynamic reversible covalent bond, the thermoplastic processing molding and solid state recycling of the polymer-based thermal interface material can be conveniently carried out, so that the strict limit between the traditional thermoplastic polymer-based thermal interface material and the thermosetting polymer-based thermal interface material is broken through to a great extent.
Drawings
FIG. 1 is a graph of the total thermal resistance (R) of a polymer-based thermal interface material total ) And contact thermal resistance (R) c ) A relationship;
FIG. 2 is a schematic diagram of a dynamic reversible exchange reaction occurring with a polyurethane resin having dual dynamic covalent bonds;
FIG. 3 is a process flow diagram of a polyurethane resin having dual dynamic covalent bonds.
Detailed Description
In order that the invention may be more clearly understood, it will now be further described with reference to the following examples and the accompanying drawings. The examples are for illustration only and do not limit the invention in any way. In the examples, each raw reagent material is commercially available, and the experimental method not specifying the specific conditions is a conventional method and a conventional condition well known in the art, or a condition recommended by an instrument manufacturer.
Example 1
Preparing a polyurethane prepolymer: weighing 10.00-20.00 g of polytetrahydrofuran glycol (Mw =3000 g/mol) in a three-neck flask, placing the three-neck flask with the polytetrahydrofuran glycol in an oil bath kettle, heating until the solid in the flask melts, and then weighing 7.50-15.00 g of isophorone diisocyanate (IPDI) in the three-neck flask. The reaction is carried out at the temperature of 70.00-90.00 ℃ without solvent or catalyst for 5.00-7.00h, after the reaction is finished, the product polyurethane prepolymer (PUP) is obtained, and the PUP is sealed and stored for standby, wherein the synthetic route is as shown in the following formula 1.
Preparing a Schiff base chain extender: 3.04g of Vanillin (VA) was weighed out and dissolved in ethanol to obtain a homogeneous solution, and the solution was transferred to a round-bottom flask. Placing the round-bottom flask into an oil bath pot, heating to 60.00 ℃, slowly dropwise adding 2.20g of diethylene glycol bis (3-aminopropyl) ether, after dropwise adding, preserving heat and continuing to react for 10.00-12.00h. After the reaction is finished, petroleum ether is adopted to extract the reaction solution, and viscous liquid which is not dissolved in the petroleum ether is used as a target product, namely a Schiff base chain extender (SBE). Removing the solvent from the SBE under vacuum to obtain the purified SBE, wherein the synthetic route is shown as the following formula 2.
Preparing the modified heat-conducting filler: 300.00g of aluminum with the particle size of 1-2 μm, 300.00g of aluminum with the particle size of 13-15 μm, 300.00g of zinc oxide with the particle size of 0.3 μm, 2.00g of dodecyl trimethoxy siloxane, 2.00g of water and 4.00 zxft 8978 of absolute ethyl alcohol are added into a 2.0L double-planet stirrer, the temperature is raised to 65.00 ℃, and the stirring is carried out for 4.00h. After stirring for 4.00h, the temperature was raised to 135.00 ℃ and stirring was continued for 4.00h at a vacuum of-90.0 kPa at a speed of 50.00 rpm. And cooling the mixture, namely the modified powder, to room temperature, sealing and storing for later use.
Stirring polyurethane prepolymer (PUP, 10.00 g), schiff base chain extender (0.18 g), cross-linking agent (0.25 g) and modified powder (104.80 g) for 1-5 min in vacuum at normal temperature, then calendering by a calender to obtain uncured polyurethane-based thermal interface material with the thickness of about 1.5mm, and putting the uncured polyurethane-based thermal interface material into an oven for curing. The curing mode is segmented curing, namely 90 ℃/2 h,120 ℃/3h and 150 ℃/3h, and the sample obtained after curing is recorded as SPU1-91wt%.
Example 2
The formula is different from that of the example 1, the hydroxyl groups provided by the SBE and the cross-linking agent respectively account for 25 percent and 75 percent of the molar content of the isocyanate groups of the prepolymer, the modified powder accounts for 91 percent of the mass of the polyurethane thermal interface material, the rest is the same as that of the example 1, and the sample obtained after curing is recorded as SPU2-91 percent by weight.
Example 3
The formula of the polyurethane thermal interface material is different from that of the embodiment 1 in that hydroxyl provided by SBE and a cross-linking agent respectively account for 50% and 50% of the molar content of isocyanate groups of a prepolymer, the mass fraction of the modified powder accounts for 91wt% of the polyurethane thermal interface material, the rest is the same as that of the embodiment 1, and a sample obtained after curing is marked as SPU3.
Example 4
The formula is different from that of example 1 in that hydroxyl groups provided by SBE and a cross-linking agent respectively account for 75% and 25% of the molar content of isocyanate groups of a prepolymer, the mass fraction of modified powder accounts for 91wt% of a polyurethane thermal interface material, the rest is the same as that of example 1, and a sample obtained after curing is marked as SPU4.
Comparative example 1
The formulation of example 1 differs in that polytetrahydrofuran diol (Mw =3000 g/mol) is substituted with polytetrahydrofuran diol (Mw =2000 g/mol) without schiff base chain extender (SBE) in the case that polytetrahydrofuran diol having a different molecular weight is used and its mass fraction is unchanged.
The thermal interface materials prepared in examples 1 to 4 and comparative example 1 were tested for thermal conductivity and tensile strength.
(1) And (3) testing the heat conductivity coefficient:
the transient plane heat source method (TPS) is adopted, which is the most convenient and accurate method in the current method for researching the heat conduction performance of the material, and is improved by a hot wire method. The heat conductivity coefficient of the polyurethane thermal interface material is tested by adopting the method (Hot Disk method), namely, an instant thermal plane probe (Hot Disk probe) is adopted, and the instrument type is TPS2500S. The specific implementation steps are as follows: the polyurethane thermal interface material was cut into 25.4mm by 25.4mm squares having a thickness of about-1.5 mm. Each sample was measured three times and the results averaged.
(2) Tensile property test of the thermal interface material:
the mechanical properties of the prepared thermal interface material are characterized by adopting an Shimadzu electronic universal tester, and the method comprises the following specific steps: cutting the thermal interface material into dumbbell-shaped sample strips, wherein the total length of the sample strips is as follows: 35mm, width: 6mm, the width of the narrowest part of the bar is 2mm, the stretching rate: 5mm/min, five measurements per sample, and the results averaged.
The thermal interface materials provided in examples 1 to 4 and comparative example 1 were tested for thermal conductivity and tensile strength according to the methods described above, and the test results are shown in table 1:
TABLE 1
| Coefficient of thermal conductivity (W/m. K) | Tensile Strength (MPa) | |
| Example 1 | 6.2 | 0.27 |
| Example 2 | 6.5 | 0.25 |
| Example 3 | 6.0 | 0.26 |
| Example 4 | 6.3 | 0.25 |
| Comparative example 1 | 5.8 | 0.35 |
The applicant states that the present invention provides a polyurethane-based thermal interface material with dual dynamic bonds and a preparation method thereof through the above examples, but the present invention is not limited to the above process steps, i.e. it does not mean that the present invention must rely on the above process steps to be implemented. It will be apparent to those skilled in the art that any modifications to the present invention, equivalent substitutions of selected materials and additions of auxiliary components, selection of specific forms, etc., are within the scope and disclosure of the present invention.
Claims (10)
1. The polyurethane thermal interface material with the double dynamic bonds is characterized in that the polyurethane thermal interface material with the double dynamic bonds is prepared from the following raw materials in parts by weight:
the polyurethane prepolymer is a reaction product of diisocyanate and polyol.
2. The polyurethane thermal interface material of claim 1 wherein the diisocyanate is selected from one or more of isophorone diisocyanate, hexamethylene diisocyanate, and trimethylhexamethylene diisocyanate;
the polyalcohol is selected from one or more of polytetrahydrofuran glycol, polyethylene glycol, polypropylene glycol and polybutadiene glycol;
preferably, the diisocyanate is selected from isophorone diisocyanate;
preferably, the polyol is selected from polytetrahydrofuran diol;
preferably, the molecular weight of the polytetrahydrofuran glycol is 2000-3000g/mol, and the mass percentage of the hydroxyl is 0.1% -3.0%.
3. The polyurethane thermal interface material of claim 1, wherein the polyurethane prepolymer is prepared by a method comprising: adding diisocyanate into the melted polyol, reacting at the temperature of 70.00-90.00 ℃ without solvent or catalyst for 5.00-7.00h, and obtaining a product, namely a polyurethane prepolymer after the reaction is finished;
preferably, the mass ratio of the diisocyanate to the polyol is (3-6): (6-8).
4. The polyurethane thermal interface material of claim 1, wherein the mass percentage of hydroxyl groups in the Schiff base chain extender containing hydroxyl groups and imino groups is 3-7%;
the Schiff base chain extender containing hydroxyl and imino provides that the molar content of hydroxyl in isocyanate groups provided by the polyurethane prepolymer is 0-75%;
preferably, the Schiff base chain extender containing hydroxyl is
5. The polyurethane thermal interface material of claim 1, wherein the thermally conductive filler is selected from one or more of aluminum oxide, aluminum, zinc oxide, aluminum hydroxide, and magnesium hydroxide;
preferably, the particle size of the heat conductive filler is 0.3-15 μm;
preferably, the heat-conducting filler is modified by a silane coupling agent;
preferably, the silane coupling agent is selected from at least one of gamma-aminopropyltriethoxysilane, gamma-glycidoxypropyltrimethoxysilane, gamma-methacryloxypropyltrimethoxysilane, decyltrimethoxysilane, dodecyltrimethoxysilane, and hexadecyltrimethoxysilane.
6. The polyurethane thermal interface material as claimed in claim 5, wherein the modification treatment of the thermally conductive filler with a silane coupling agent is carried out by: stirring and mixing the heat-conducting filler, the silane coupling agent, the water and the absolute ethyl alcohol at 60-70 ℃, then heating to 130-150 ℃, continuously stirring for 3-4h at the speed of 40-60rpm under the vacuum degree of-90.0 kPa, and cooling to room temperature after the stirring is finished, thus obtaining the heat-conducting silicone oil.
7. The polyurethane thermal interface material of claim 1 wherein the crosslinker is selected from the group consisting of at least one of triethanolamine or glycerol;
preferably, the cross-linking agent is selected from triethanolamine.
8. The polyurethane thermal interface material of claim 1, further comprising 0-0.005 parts of an antioxidant;
preferably, the antioxidant is at least one of antioxidant 1010, antioxidant 1076, and antioxidant DLTP.
9. The method for preparing the polyurethane-based thermal interface material having dual dynamic bonds as set forth in claim 1, comprising the steps of: according to the mass parts, the polyurethane prepolymer, the Schiff base chain extender containing hydroxyl and imino, the heat-conducting filler and the cross-linking agent are stirred and mixed, and then the stirred and mixed materials are calendered and thermally cured to obtain the polyurethane heat-conducting resin.
10. The preparation method according to claim 8, wherein the stirring is carried out for 1 to 5min under vacuum at normal temperature;
the temperature of the heat curing is 90-150 ℃, and the curing time is 4-9 h;
preferably, the thermal curing is segmented thermal curing;
preferably, the segmented thermal curing is performed at 90 ℃ for 2h, at 120 ℃ for 3h and at 150 ℃ for 3h;
preferably, an antioxidant is added into the polyurethane prepolymer, the hydroxyl-containing Schiff base chain extender, the heat-conducting filler and the cross-linking agent.
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Citations (5)
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|---|---|---|---|---|
| CN107033310A (en) * | 2017-04-25 | 2017-08-11 | 四川大学 | Containing dual dynamic it is covalently cross-linked weigh machined polyurethane and preparation method thereof |
| CN110573547A (en) * | 2017-05-12 | 2019-12-13 | 株式会社可乐丽 | Chain extender, polyurethane and modification method thereof, polishing layer, polishing pad and polishing method |
| WO2020205137A1 (en) * | 2019-04-05 | 2020-10-08 | DDP Specialty Electronic Materials US, Inc. | Polyurethane based thermal interface material |
| CN112662358A (en) * | 2020-12-09 | 2021-04-16 | 深圳市美信电子有限公司 | Single-component heat-conducting interface material and preparation method and application thereof |
| CN113861662A (en) * | 2021-09-30 | 2021-12-31 | 南昌航空大学 | Self-repairing polyurethane heat-conducting composite material and preparation method thereof |
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2022
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107033310A (en) * | 2017-04-25 | 2017-08-11 | 四川大学 | Containing dual dynamic it is covalently cross-linked weigh machined polyurethane and preparation method thereof |
| CN110573547A (en) * | 2017-05-12 | 2019-12-13 | 株式会社可乐丽 | Chain extender, polyurethane and modification method thereof, polishing layer, polishing pad and polishing method |
| WO2020205137A1 (en) * | 2019-04-05 | 2020-10-08 | DDP Specialty Electronic Materials US, Inc. | Polyurethane based thermal interface material |
| CN112662358A (en) * | 2020-12-09 | 2021-04-16 | 深圳市美信电子有限公司 | Single-component heat-conducting interface material and preparation method and application thereof |
| CN113861662A (en) * | 2021-09-30 | 2021-12-31 | 南昌航空大学 | Self-repairing polyurethane heat-conducting composite material and preparation method thereof |
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