JP6309958B2 - 芳香族カルボジイミドの硬化 - Google Patents
芳香族カルボジイミドの硬化 Download PDFInfo
- Publication number
- JP6309958B2 JP6309958B2 JP2015535778A JP2015535778A JP6309958B2 JP 6309958 B2 JP6309958 B2 JP 6309958B2 JP 2015535778 A JP2015535778 A JP 2015535778A JP 2015535778 A JP2015535778 A JP 2015535778A JP 6309958 B2 JP6309958 B2 JP 6309958B2
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- JP
- Japan
- Prior art keywords
- carbodiimide
- prepolymer
- weight
- group
- carboxylate
- 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.)
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- -1 aromatic carbodiimides Chemical class 0.000 title claims description 33
- 150000001718 carbodiimides Chemical class 0.000 claims description 69
- 238000000034 method Methods 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 21
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 claims description 15
- 229920005862 polyol Polymers 0.000 claims description 15
- 150000007942 carboxylates Chemical class 0.000 claims description 11
- 239000002775 capsule Substances 0.000 claims description 10
- 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 claims description 8
- 239000011342 resin composition Substances 0.000 claims description 8
- 150000003077 polyols Chemical class 0.000 claims description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 5
- 229920000570 polyether Polymers 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 238000000576 coating method Methods 0.000 description 15
- 229920005989 resin Polymers 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- 239000001993 wax Substances 0.000 description 14
- 239000011248 coating agent Substances 0.000 description 13
- 239000012948 isocyanate Substances 0.000 description 13
- 150000002513 isocyanates Chemical class 0.000 description 13
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 12
- 239000011257 shell material Substances 0.000 description 12
- 239000000758 substrate Substances 0.000 description 11
- 239000010408 film Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000004698 Polyethylene Substances 0.000 description 8
- 229920000573 polyethylene Polymers 0.000 description 8
- 239000011230 binding agent Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000012188 paraffin wax Substances 0.000 description 6
- 235000011056 potassium acetate Nutrition 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000005538 encapsulation Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000004200 microcrystalline wax Substances 0.000 description 4
- 235000019808 microcrystalline wax Nutrition 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 230000002028 premature Effects 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
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- 238000003475 lamination Methods 0.000 description 3
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- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000012178 vegetable wax Substances 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000006845 Michael addition reaction Methods 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 235000019383 crystalline wax Nutrition 0.000 description 2
- 238000007210 heterogeneous catalysis Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000012968 metallocene catalyst Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- IFZAHHXECWEMAO-UHFFFAOYSA-N 1-(3-methylphenyl)-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical group CC1=CC=CC(P2(=O)C=CCC2)=C1 IFZAHHXECWEMAO-UHFFFAOYSA-N 0.000 description 1
- YUQUHJGNZFFDAA-UHFFFAOYSA-N 1-phenyl-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound C=1C=CC=CC=1P1(=O)CCC=C1 YUQUHJGNZFFDAA-UHFFFAOYSA-N 0.000 description 1
- YMKWWHFRGALXLE-UHFFFAOYSA-N 4-methyl-1-phenyl-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound C1CC(C)=CP1(=O)C1=CC=CC=C1 YMKWWHFRGALXLE-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229910017107 AlOx Inorganic materials 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- SAJCVFNJOGNICP-UHFFFAOYSA-N C(C)P1(CC(=CC=C1)C)=O Chemical compound C(C)P1(CC(=CC=C1)C)=O SAJCVFNJOGNICP-UHFFFAOYSA-N 0.000 description 1
- MRBNJAMYAHSBFS-UHFFFAOYSA-N C1(=CC=CC=C1)P1(CC(=CC=C1)C)=O Chemical compound C1(=CC=CC=C1)P1(CC(=CC=C1)C)=O MRBNJAMYAHSBFS-UHFFFAOYSA-N 0.000 description 1
- IPCUUURCYULXHA-UHFFFAOYSA-N CP1(CC(=CC=C1)C)=O Chemical compound CP1(CC(=CC=C1)C)=O IPCUUURCYULXHA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- ZBVOEVQTNYNNMY-UHFFFAOYSA-N O=P1=CCCC1 Chemical class O=P1=CCCC1 ZBVOEVQTNYNNMY-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 229940117927 ethylene oxide Drugs 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011104 metalized film Substances 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- QJMMCGKXBZVAEI-UHFFFAOYSA-N tris(trimethylsilyl) phosphate Chemical compound C[Si](C)(C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C QJMMCGKXBZVAEI-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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4829—Polyethers containing 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
- 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
- C08G18/28—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
- C08G18/70—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
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
-
- 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
- C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine 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
- C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
-
- 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
- C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
- C08G18/025—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only the polymeric products containing carbodiimide groups
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
Landscapes
- 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)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyesters Or Polycarbonates (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Description
溶液粘度を、およそ25℃の温度で動作し、測定される粘度範囲に適切な付属品を有するブルックフィールド粘度計を用いて測定した。純樹脂粘度を、示される温度で、スピンドル#27を有する恒温装置少量サンプルアダプタおよびサンプルチャンバを用いて、ブルックフィールド粘度計で測定した。樹脂は以下の手順に記載のとおりに調製された。
酢酸エチル溶液10.0g中の実施例1のカルボジイミド樹脂10.0gに、エタノール中3.37%酢酸カリウムを0.20g混合して塗布し、1.0lbs/rm(1.628g/m2)のコーティング重量を得た。積層体は周囲条件で硬化された。結合強度は硬化時間の機能として観察され、以下のように報告される。
酢酸エチル溶液10.0g中の実施例2のカルボジイミドの樹脂10.0gに、エタノール中0.92%酢酸カリウムを2.0g混合して塗布し、1.0lbs/rm(1.628g/m2)のコーティング重量を得た。積層体は周囲条件で硬化された。結合強度は硬化時間の機能として観察され、以下のように報告される。
酢酸エチル溶液10.0g中の実施例3のカルボジイミドの樹脂10.0gに、エタノール中0.92%酢酸カリウム2.0gを混合して塗布し、1.0lbs/rm(1.628g/m2)のコーティング重量を得た。積層体は周囲条件で硬化された。結合強度は硬化時間の機能として観察され、以下のように報告される。
酢酸エチル溶液10.0g中の実施例4のカルボジイミドの樹脂10.0gに、エタノール中0.92%酢酸カリウム2.0gを混合して塗布し、1.0lbs/rm(1.628g/m2)のコーティング重量を得た。積層体は周囲条件で硬化された。結合強度は硬化時間の機能として観察され、以下のように報告される。
酢酸エチル溶液10.0g中の実施例5のカルボジイミドの樹脂10.0gに、エタノール中0.92%酢酸カリウムを2.0g混合して塗布し、1.0lbs/rm(1.628g/m2)のコーティング重量を得た。積層体は周囲条件で硬化された。結合強度は硬化時間の機能として観察され、以下のように報告される。
酢酸エチル溶液10.0g中の実施例6のカルボジイミド樹脂10.0gに、エタノール中0.92%酢酸カリウムを2.0g混合して塗布し、1.0lbs/rm(1.628g/m2)のコーティング重量を得た。積層体は周囲条件で硬化された。結合強度は硬化時間の機能として観察され、以下のように報告される。
Claims (3)
- 芳香族多官能カルボジイミドを重合する方法であって、前記芳香族多官能カルボジイミドをカルボン酸塩と15℃〜90℃の温度で接触させることを含み、前記芳香族多官能カルボジイミドが、1.3〜6の平均カルボジイミド官能価を有するカルボジイミドプレポリマーであり、前記カルボジイミドプレポリマーが、(i)ジフェニルメタンジイソシアネートおよび前記カルボジイミドプレポリマーの重量に基づいて31重量%〜45重量%の脂肪族ポリオールの重合残基、(ii)カルボジイミド基、ならびに(iii)脂肪族置換基を有するウレタン基を含み、前記カルボジイミドプレポリマーが、前記カルボジイミドプレポリマーの重量に基づいて2重量%〜5重量%のカルボジイミド基含量を有する、方法。
- カルボジイミドプレポリマーとカルボン酸塩とを含む硬化性樹脂組成物であって、前記カルボジイミドプレポリマーが、各カルボジイミド基に隣接する2つの芳香族置換基を有し、芳香族多官能カルボジイミドが、1.3〜6の平均カルボジイミド官能価を有するカルボジイミドプレポリマーであり、前記カルボジイミドプレポリマーが、(i)ジフェニルメタンジイソシアネートおよび前記カルボジイミドプレポリマーの重量に基づいて31重量%〜45重量%の脂肪族ポリオールの重合残基、(ii)カルボジイミド基、ならびに(iii)脂肪族置換基を有するウレタン基を含み、前記カルボジイミドプレポリマーが、前記カルボジイミドプレポリマーの重量に基づいて2重量%〜5重量%のカルボジイミド基含量および前記カルボジイミドプレポリマーの重量に基づいて1重量%以下の残留イソシアネート基含量を有し、前記カルボン酸塩の量が、硬化性樹脂組成物の合計に対する割合で、固形分に基づき0.03重量%〜0.3重量%である、硬化性樹脂組成物。
- 前記カルボジイミドプレポリマーが、前記カルボジイミドプレポリマーの重量に基づいて30重量%〜50重量%のポリエーテルポリオールの重合残基を含み、前記カルボン酸塩がカプセル内に収容されている、請求項2に記載の硬化性樹脂組成物。
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US201261710791P | 2012-10-08 | 2012-10-08 | |
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PCT/US2013/063204 WO2014058700A1 (en) | 2012-10-08 | 2013-10-03 | Curing of aromatic carbodiimides |
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US2800457A (en) | 1953-06-30 | 1957-07-23 | Ncr Co | Oil-containing microscopic capsules and method of making them |
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JPS56140354A (en) | 1980-04-04 | 1981-11-02 | Hitachi Ltd | Manufacture of composite type electrophotographic plate |
JPS6140354A (ja) * | 1984-08-01 | 1986-02-26 | Teijin Ltd | 樹脂組成物 |
JPS61268714A (ja) * | 1985-05-22 | 1986-11-28 | Nisshinbo Ind Inc | 耐熱性の高い熱硬化性樹脂の製造方法 |
DE3643238C2 (ja) * | 1985-03-29 | 1989-08-03 | Nisshinbo Industries, Inc., Tokio/Tokyo, Jp | |
US5271881A (en) | 1987-09-28 | 1993-12-21 | Redding Bruce K | Apparatus and method for making microcapsules |
IT1230705B (it) * | 1989-01-27 | 1991-10-29 | Boston Spa | Composizione di hot melt reticolabile |
JPH05320611A (ja) * | 1992-05-18 | 1993-12-03 | Nisshinbo Ind Inc | フィルム状接着剤組成物 |
US5574083A (en) * | 1993-06-11 | 1996-11-12 | Rohm And Haas Company | Aromatic polycarbodiimide crosslinkers |
US5357021A (en) | 1993-07-21 | 1994-10-18 | Basf Corporation | Reactive carbodimide compositions |
JP2002187932A (ja) * | 2000-12-19 | 2002-07-05 | Dainichiseika Color & Chem Mfg Co Ltd | ポリカルボジイミド化合物、その製造方法および物品の処理方法 |
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CN104704056A (zh) | 2015-06-10 |
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BR112015006952A2 (pt) | 2017-07-04 |
RU2015117392A (ru) | 2016-11-27 |
US9328189B2 (en) | 2016-05-03 |
TW201420677A (zh) | 2014-06-01 |
MX2015003858A (es) | 2015-07-17 |
EP2885351B1 (en) | 2019-06-26 |
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