JP2022528401A - ポリウレタン系熱界面材料 - Google Patents
ポリウレタン系熱界面材料 Download PDFInfo
- Publication number
- JP2022528401A JP2022528401A JP2021557893A JP2021557893A JP2022528401A JP 2022528401 A JP2022528401 A JP 2022528401A JP 2021557893 A JP2021557893 A JP 2021557893A JP 2021557893 A JP2021557893 A JP 2021557893A JP 2022528401 A JP2022528401 A JP 2022528401A
- Authority
- JP
- Japan
- Prior art keywords
- interface material
- thermal interface
- material composition
- diisocyanate
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000463 material Substances 0.000 title claims abstract description 37
- 239000004814 polyurethane Substances 0.000 title claims description 10
- 229920002635 polyurethane Polymers 0.000 title claims description 9
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims abstract description 29
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims description 43
- 239000005056 polyisocyanate Substances 0.000 claims description 19
- 229920001228 polyisocyanate Polymers 0.000 claims description 19
- 125000001931 aliphatic group Chemical group 0.000 claims description 18
- 239000011230 binding agent Substances 0.000 claims description 17
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000002245 particle Substances 0.000 claims description 14
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 13
- PLFFHJWXOGYWPR-HEDMGYOXSA-N (4r)-4-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-3-yl]pentan-1-ol Chemical compound C([C@]1(C)[C@H]2CC[C@H]34)CCC(C)(C)[C@@H]1CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@@H]1[C@@H](CCCO)C PLFFHJWXOGYWPR-HEDMGYOXSA-N 0.000 claims description 10
- 229920005862 polyol Polymers 0.000 claims description 10
- 150000003077 polyols Chemical class 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 8
- 239000012948 isocyanate Substances 0.000 claims description 8
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 8
- 150000002513 isocyanates Chemical class 0.000 claims description 7
- 125000005442 diisocyanate group Chemical group 0.000 claims description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 5
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical group O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 claims description 3
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 claims description 3
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims 1
- 239000000654 additive Substances 0.000 abstract description 8
- 230000000996 additive effect Effects 0.000 abstract description 4
- 238000010586 diagram Methods 0.000 abstract 1
- 230000000740 bleeding effect Effects 0.000 description 7
- 239000000843 powder Substances 0.000 description 6
- 239000000945 filler Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- -1 aliphatic isocyanate Chemical class 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- BYPFICORERPGJY-UHFFFAOYSA-N 3,4-diisocyanatobicyclo[2.2.1]hept-2-ene Chemical compound C1CC2(N=C=O)C(N=C=O)=CC1C2 BYPFICORERPGJY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 101710149792 Triosephosphate isomerase, chloroplastic Proteins 0.000 description 2
- 101710195516 Triosephosphate isomerase, glycosomal Proteins 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 2
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- YXRKNIZYMIXSAD-UHFFFAOYSA-N 1,6-diisocyanatohexane Chemical compound O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O YXRKNIZYMIXSAD-UHFFFAOYSA-N 0.000 description 1
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- 102100035474 DNA polymerase kappa Human genes 0.000 description 1
- 101710108091 DNA polymerase kappa Proteins 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 229920013701 VORANOL™ Polymers 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- FGPCETMNRYMFJR-UHFFFAOYSA-L [7,7-dimethyloctanoyloxy(dimethyl)stannyl] 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC(=O)O[Sn](C)(C)OC(=O)CCCCCC(C)(C)C FGPCETMNRYMFJR-UHFFFAOYSA-L 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- 230000002902 bimodal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000011231 conductive filler Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/60—Heating or cooling; Temperature control
- H01M10/65—Means for temperature control structurally associated with the cells
- H01M10/653—Means for temperature control structurally associated with the cells characterised by electrically insulating or thermally conductive materials
-
- 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
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- 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
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
-
- 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
-
- 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
- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
- C08G18/4841—Polyethers containing oxyethylene units and other oxyalkylene units containing oxyethylene end 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
- 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
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- 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
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
-
- 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
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
- C08L75/08—Polyurethanes from polyethers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/60—Heating or cooling; Temperature control
- H01M10/61—Types of temperature control
- H01M10/613—Cooling or keeping cold
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2227—Oxides; Hydroxides of metals of aluminium
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/002—Physical properties
- C08K2201/005—Additives being defined by their particle size in general
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/34—Arrangements for cooling, heating, ventilating or temperature compensation ; Temperature sensing arrangements
- H01L23/36—Selection of materials, or shaping, to facilitate cooling or heating, e.g. heatsinks
- H01L23/373—Cooling facilitated by selection of materials for the device or materials for thermal expansion adaptation, e.g. carbon
- H01L23/3737—Organic materials with or without a thermoconductive filler
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/60—Heating or cooling; Temperature control
- H01M10/62—Heating or cooling; Temperature control specially adapted for specific applications
- H01M10/625—Vehicles
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M2220/00—Batteries for particular applications
- H01M2220/20—Batteries in motive systems, e.g. vehicle, ship, plane
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Electrochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
・PU-Pre-1.040g/mlの密度及び1500mPa-sの粘度(動的)を有するメチレンジフェニルジイソシアネート(MDI)ベースのウレタンプレポリマー;
・ポリイソシアネート-Covestroから入手したヘキサメチレン-1,6-ジイソシアネート(HDI)ホモポリマー(HDI三量体);
・モノール-DowDuPontから入手した、C12~C14脂肪族アルコールで開始された完全にプロポキシル化された(プロピレンオキシドを含む)モノール(MW935g/mol、OH価:60.4、当量:927);
・DowDuPontから商品名Voranol(登録商標)1010Lとして入手した、ポリオール-1-ポリプロピレンオキシドポリオール(官能価:2、MW:1000g/mol);
・DowDuPontから商品名Voranol(登録商標)CP4610として入手した、ポリオール-2-グリセリンで開始されたエチレンオキシドベースのプロポキシル化トリオール(MW:1800g/mol、OH価:35KOH/g);
・ATH-二峰性に分布した水酸化アルミニウムであり、小さな粒子の平均粒子サイズは10μm未満であり、大きな粒子の平均粒子サイズは50μm超である;
・CaCO3-沈降炭酸カルシウム;
・触媒-1-Evonikから商品名DABCOTMT-12として入手したジブチルスズジラウレート(DBTDL);
・触媒-2-Momentiveから商品名FomrezTMUL28として入手したジメチルスズジネオデカノエート;
・脂肪酸-不飽和C16~C18脂肪酸のメチルエステル;
・可塑剤-1,2-ベンゼンカルボン酸のジ-C8~C10アルキルエステル
・DINP-Evonikから商品名VestinolTM9として入手したフタル酸ジ-イソノニル;
・シラン-ヘキサデシルトリメトキシシラン;
・PU(非反応性)-以下の処方及び特性(表1)を有する非反応性ポリウレタンプレポリマーは、1)反応器内でポリイソシアネートとモノールとを混合し、温度を60℃まで上げ;2)反応混合物に触媒-1を添加し;3)混合物を窒素雰囲気下で80℃で45分間撹拌し、続いて真空下で10分間撹拌し;4)反応生成物を室温まで冷却し、密閉容器に移す;ことによって調製した。
サンプルの準備
比較例CE1~CE13及び実施例E1~E14のそれぞれにおいて、表3又は表4に記載されている全ての成分(最初に液体成分、その後固体成分)をプラネタリーミキサー又は二重非対称遠心分離機に入れ、真空下で約30分間混合し、得られたTIM(ペースト形態)をカートリッジ、ペール缶、又はドラム缶の中に移して保管した。
各サンプルにおけるTIMペーストの圧入力は、張力計(Zwick)を使用して測定した。各サンプルからのTIMペーストを金属表面に配置した。直径40mmのアルミニウムピストンをサンプルペーストの上に配置し、サンプルペーストを5mm(初期厚さ)まで圧縮した。次いで、サンプルペーストを1mm/sの速度で0.3mmの厚さまで更に圧縮し、力のたわみ曲線を記録した。0.5mmの厚さにおける力(N)を圧入力として記録した。
各サンプルで得られたTIMペーストについての熱伝導率は、ZFW StuttgartのTIMテスターを使用してASTM 5470に従って測定した。測定は、厚さ1.8~1.2mmでSpaltplusモードで行い、絶対熱伝導率λ(W/m・K)を記録した。
各サンプルで得られたTIMペーストを厚さ2.0mmの試験板へと成形し、体積抵抗率(Ω.cm)を、DIN IEC 93/VDE 0303/HD 429 S1に従って100V且つ23℃でこれらの試験板を使用して測定した。
各サンプルについて、「e-コーティングされた鋼基材/TIM/ガラス」として構成されたサンドイッチパネルを作製した。e-コーティングされた鋼基材をイソプロパノールで洗浄し、その後上にTIMペーストを塗布した。次いで、TIMペーストをガラス基材で3.0mmまで圧縮(スペーサーで厚さを調整)し、直径60mmの試験サンプルを形成した。その後、試験サンプルを気候変化条件に曝露し、各サイクルは完了に12時間要し、-40℃(制御されていない湿度)で4時間、温度を80℃に調整するのに4時間、そして80重量%の相対湿度で80℃で4時間で構成された。その後、サンドイッチパネルを気候調整後に目視検査し、亀裂の形成、相分離、及び滑りのないサンプルを「ok」と評価し、それ以外を「Nok」と評価した。
Claims (11)
- a)少なくとも1種の非反応性ポリウレタンプレポリマーを含むウレタンベースのバインダー成分と、
b)約80~95重量%の水酸化アルミニウムとを含有する熱界面材料組成物であって、
組成物の総重量が合計100%重量であり、
前記少なくとも1種の非反応性ポリウレタンプレポリマーが、i)少なくとも1種のポリイソシアネートと少なくとも1種の脂肪族モノールとの反応生成物であり、ii)残留イソシアネート基を実質的に含まず、iii)平均分子量が2,000~50,000g/molであり、
ポリオールベースの材料が前記組成物中に存在する場合には、前記ポリオールベースの材料の含有量は前記ウレタンベースのバインダー成分の総含有量よりも少ない、熱界面材料組成物。 - 前記ウレタンベースのバインダー成分が、前記組成物の総重量を基準として約2~20重量%のレベルで存在する、請求項1に記載の熱界面材料組成物。
- 前記少なくとも1種の非反応性ポリウレタンプレポリマーが、前記少なくとも1種の非反応性ポリウレタンプレポリマーの重量を基準として約0.8重量%未満の前記残留イソシアネート基を含む、請求項1に記載の熱界面材料組成物。
- 前記少なくとも1種の非反応性ポリウレタンプレポリマーが、前記少なくとも1種の脂肪族ポリイソシアネートと少なくとも1種の脂肪族モノールとの反応生成物である、請求項1に記載の熱界面材料組成物。
- 前記少なくとも1種の脂肪族ポリイソシアネートが、エチレンジイソシアネート;ヘキサメチレン-1,6-ジイソシアネート(HDI);イソホロンジイソシアネート(IPDI);4,4’-、2,2’-、及び2,4’-ジシクロヘキシルメタンジイソシアネート(H12MDI);ノルボルネンジイソシアネート;1,3-及び1,4-(ビスイソシアナトメチル)シクロヘキサン(そのシス又はトランス異性体を含む);テトラメチレン-1,4-ジイソシアネート(TMXDI);1,12-ドデカンジイソシアネート;2,2,4-トリメチルヘキサメチレンジイソシアネート;及びそれらの2つ以上の組み合わせからなる群から選択される多官能性イソシアネートに基づくプレポリマーである、請求項4に記載の熱界面材料組成物。
- 前記少なくとも1種の脂肪族ポリイソシアネートがヘキサメチレン-1,6-ジイソシアネート(HDI)に基づくプレポリマーである、請求項5に記載の熱界面材料組成物。
- 前記ウレタンベースのバインダー成分が、前記非反応性ポリウレタンプレポリマーとは異なる少なくとも1種の他のポリウレタンを任意選択的に更に含んでいてもよく、その場合の前記少なくとも1種の非反応性ポリウレタンプレポリマーと前記少なくとも1種の他のポリウレタンとの重量比が約100:0~15:85の範囲である、請求項2に記載の熱界面材料組成物。
- 前記水酸化アルミニウムが約5~100μmの範囲の平均粒子サイズを有する、請求項1に記載の熱界面材料組成物。
- 前記水酸化アルミニウムが多峰性の粒子サイズ分布を有する、請求項8に記載の熱界面材料組成物。
- 請求項1に記載の熱界面材料組成物を含む物品。
- 1つ以上の電池セルと冷却ユニットとから形成される電池モジュールを更に含み、前記電池モジュールが、前記熱界面材料組成物を介して前記冷却ユニットに接続される、請求項10に記載の物品。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201962829817P | 2019-04-05 | 2019-04-05 | |
US62/829,817 | 2019-04-05 | ||
PCT/US2020/020892 WO2020205137A1 (en) | 2019-04-05 | 2020-03-04 | Polyurethane based thermal interface material |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2022528401A true JP2022528401A (ja) | 2022-06-10 |
Family
ID=69960760
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2021557893A Pending JP2022528401A (ja) | 2019-04-05 | 2020-03-04 | ポリウレタン系熱界面材料 |
Country Status (6)
Country | Link |
---|---|
US (1) | US20220209324A1 (ja) |
EP (1) | EP3947500B1 (ja) |
JP (1) | JP2022528401A (ja) |
KR (1) | KR20210153046A (ja) |
CN (1) | CN113631610B (ja) |
WO (1) | WO2020205137A1 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115386216A (zh) * | 2022-09-01 | 2022-11-25 | 深圳先进电子材料国际创新研究院 | 一种具有双重动态键的聚氨酯热界面材料及其制备方法 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4066578A (en) * | 1976-01-14 | 1978-01-03 | W. R. Grace & Co. | Heavily loaded flame retardant urethane and method |
DE3366944D1 (en) * | 1982-05-03 | 1986-11-20 | Bauer Schaum Chem | Improved polyurea foams |
US4863994A (en) * | 1988-06-24 | 1989-09-05 | The Dow Chemical Company | Use of monohydric alcohols in molded polyurethane resins |
JP2002015843A (ja) * | 2000-06-29 | 2002-01-18 | Ibiden Co Ltd | セラミックヒーターの製造方法 |
US7112631B2 (en) * | 2002-10-24 | 2006-09-26 | National Starch And Chemical Investment Holding Corporation | Moisture cured reactive hot melt adhesive with monofunctional reactants as grafting agents |
CN102792442A (zh) * | 2010-03-10 | 2012-11-21 | 日东电工株式会社 | 绝热散热片及装置内结构 |
JP5697755B2 (ja) * | 2011-10-12 | 2015-04-08 | サンユレック株式会社 | 電気絶縁用ポリウレタン樹脂組成物 |
CN102533200B (zh) * | 2012-02-29 | 2013-11-20 | 广州睿腾化工产品有限公司 | 双组份聚氨酯胶粘剂 |
ES2959454T3 (es) * | 2015-07-06 | 2024-02-26 | Dow Global Technologies Llc | Prepolímeros de poliuretano |
EP3487899B1 (de) * | 2016-07-21 | 2021-03-17 | Sika Technology AG | Flammhemmende kleb- und dichtstoffe mit verbesserten mechanischen eigenschaften |
JP6408738B1 (ja) * | 2018-05-23 | 2018-10-17 | 日清紡ホールディングス株式会社 | 放熱構造体の製造方法 |
-
2020
- 2020-03-04 JP JP2021557893A patent/JP2022528401A/ja active Pending
- 2020-03-04 EP EP20714084.9A patent/EP3947500B1/en active Active
- 2020-03-04 KR KR1020217031472A patent/KR20210153046A/ko unknown
- 2020-03-04 US US17/429,702 patent/US20220209324A1/en active Pending
- 2020-03-04 WO PCT/US2020/020892 patent/WO2020205137A1/en unknown
- 2020-03-04 CN CN202080023998.0A patent/CN113631610B/zh active Active
Also Published As
Publication number | Publication date |
---|---|
US20220209324A1 (en) | 2022-06-30 |
EP3947500B1 (en) | 2023-03-22 |
CN113631610B (zh) | 2023-06-27 |
EP3947500A1 (en) | 2022-02-09 |
WO2020205137A1 (en) | 2020-10-08 |
KR20210153046A (ko) | 2021-12-16 |
CN113631610A (zh) | 2021-11-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6693972B2 (ja) | ポリ(ブチレンオキシド)に基づくイソシアネート末端準プレポリマーを使用して作製された2液型ポリウレタン接着剤 | |
AU2008225757B2 (en) | Polyisocyanate-based adhesive | |
US9834711B2 (en) | One-pack moisture-curing composition | |
CN105308087B (zh) | 1液湿气固化型聚氨酯组合物 | |
RU2654064C2 (ru) | Синтез и применение композиций металлосодержащих полиэдрических олигомерных силсесквиоксановых катализаторов | |
CA1177196A (en) | Storable flowable polyurethane composition | |
JP6926522B2 (ja) | ポリウレタン樹脂形成性組成物 | |
CN111212861A (zh) | 氨基甲酸酯丙烯酸酯混合结构粘合剂 | |
JP2022528401A (ja) | ポリウレタン系熱界面材料 | |
JP6069576B2 (ja) | スプレーポリウレタンエラストマーの製造方法及び該方法で製造されたエラストマー | |
CN104837941B (zh) | 固体可自粘的含异氰酸酯有机聚合物和其使用方法 | |
CN115103867B (zh) | 包含硅烷封端的尿烷预聚物的基于聚氨酯的热界面材料 | |
CN108314766A (zh) | 一种微交联型ndi基聚氨酯弹性体的合成工艺 | |
JP7219797B2 (ja) | 封止用ポリウレタン樹脂組成物および封止物 | |
CN117897426A (zh) | 含异氰酸酯的组合物及二液反应型聚氨酯树脂组合物 | |
KR101787964B1 (ko) | 저장 안정성이 향상된 수분산 우레탄 바인더를 함유하는 친환경 도막형 바닥재 | |
JP5596921B2 (ja) | ポリウレタン樹脂組成物及びその硬化物 | |
CN104151201B (zh) | 一种多异氰酸酯加合物及其制备方法 | |
US20220145147A1 (en) | Moisture curable adhesive compositions | |
WO2023216153A1 (en) | Two-component polyurethane adhesive composition | |
WO2023216173A1 (en) | Two-component polyurethane adhesive composition | |
KR20240034207A (ko) | 내습성 2성분 접착제 조성물 | |
JP2016050216A (ja) | 二液常温硬化型ウレタン組成物 | |
KR20140145636A (ko) | 폴리이소시아네이트 기재 접착제 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
RD03 | Notification of appointment of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7423 Effective date: 20210930 |
|
RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20220126 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20230208 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20240208 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20240227 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20240419 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20240604 |