JP5021469B2 - アミン組成物 - Google Patents
アミン組成物 Download PDFInfo
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- JP5021469B2 JP5021469B2 JP2007519808A JP2007519808A JP5021469B2 JP 5021469 B2 JP5021469 B2 JP 5021469B2 JP 2007519808 A JP2007519808 A JP 2007519808A JP 2007519808 A JP2007519808 A JP 2007519808A JP 5021469 B2 JP5021469 B2 JP 5021469B2
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- epoxy
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- 239000000203 mixture Substances 0.000 title claims description 54
- 150000001412 amines Chemical class 0.000 title claims description 34
- 239000003795 chemical substances by application Substances 0.000 claims description 24
- 229920005989 resin Polymers 0.000 claims description 18
- 239000011347 resin Substances 0.000 claims description 18
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 claims description 12
- 229920000647 polyepoxide Polymers 0.000 claims description 12
- 239000004593 Epoxy Substances 0.000 claims description 11
- 239000003822 epoxy resin Substances 0.000 claims description 11
- -1 glycol alkyl ether Chemical class 0.000 claims description 11
- 238000000576 coating method Methods 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 6
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 6
- BYLSIPUARIZAHZ-UHFFFAOYSA-N 2,4,6-tris(1-phenylethyl)phenol Chemical compound C=1C(C(C)C=2C=CC=CC=2)=C(O)C(C(C)C=2C=CC=CC=2)=CC=1C(C)C1=CC=CC=C1 BYLSIPUARIZAHZ-UHFFFAOYSA-N 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000003700 epoxy group Chemical group 0.000 claims description 5
- 239000006260 foam Substances 0.000 claims description 5
- ZETYUTMSJWMKNQ-UHFFFAOYSA-N n,n',n'-trimethylhexane-1,6-diamine Chemical compound CNCCCCCCN(C)C ZETYUTMSJWMKNQ-UHFFFAOYSA-N 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 claims description 3
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 238000006735 epoxidation reaction Methods 0.000 claims 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 8
- 229920001187 thermosetting polymer Polymers 0.000 description 8
- 150000004985 diamines Chemical class 0.000 description 7
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- 235000013162 Cocos nucifera Nutrition 0.000 description 4
- 244000060011 Cocos nucifera Species 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 238000004382 potting Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- BUZMJVBOGDBMGI-UHFFFAOYSA-N 1-phenylpropylbenzene Chemical compound C=1C=CC=CC=1C(CC)C1=CC=CC=C1 BUZMJVBOGDBMGI-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- DPQHRXRAZHNGRU-UHFFFAOYSA-N 2,4,4-trimethylhexane-1,6-diamine Chemical compound NCC(C)CC(C)(C)CCN DPQHRXRAZHNGRU-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 1
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 1
- ZAXCZCOUDLENMH-UHFFFAOYSA-N 3,3,3-tetramine Chemical compound NCCCNCCCNCCCN ZAXCZCOUDLENMH-UHFFFAOYSA-N 0.000 description 1
- KRPRVQWGKLEFKN-UHFFFAOYSA-N 3-(3-aminopropoxy)propan-1-amine Chemical compound NCCCOCCCN KRPRVQWGKLEFKN-UHFFFAOYSA-N 0.000 description 1
- UIOLCZFGHGKMDD-UHFFFAOYSA-N 3-[12-(3-aminopropoxy)dodecoxy]propan-1-amine Chemical compound NCCCOCCCCCCCCCCCCOCCCN UIOLCZFGHGKMDD-UHFFFAOYSA-N 0.000 description 1
- POTQBGGWSWSMCX-UHFFFAOYSA-N 3-[2-(3-aminopropoxy)ethoxy]propan-1-amine Chemical compound NCCCOCCOCCCN POTQBGGWSWSMCX-UHFFFAOYSA-N 0.000 description 1
- BVUDKBBYMKCBAM-UHFFFAOYSA-N 4-[2-[2-(3-aminopropoxy)ethoxy]ethoxy]butan-1-amine Chemical compound NCCCCOCCOCCOCCCN BVUDKBBYMKCBAM-UHFFFAOYSA-N 0.000 description 1
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical class CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical class C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 235000013849 propane Nutrition 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
- C08G18/6685—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3225 or polyamines of C08G18/38
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1444—Monoalcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Emergency Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
外部から加えられる弾性化剤は、反応性ではなく、熱硬化性樹脂網状構造体に組み込まれる。この改良法は、ある種の用途についてのみ適している。これらは、空間を満たすことによってのみ網状構造体を膨張させる。外部から加えられる可塑剤としては、タール;フタル酸エステル類;高沸点アルコール類;グリコール類;ケトン樹脂;ビニルポリマー;および、エポキシ樹脂およびアミン硬化剤と反応性ではない同様の製品が挙げられる。エポキシ樹脂の内部弾性化は、例えば、DE-A 2 200 717に記載されているように、硬化剤の官能性を低下させることによって達成することができる。
比較的高粘度が厄介であることが見出されている。硬化性混合物の脱泡は、高粘度で乏しく、自己均一塗膜における使用が極めて難しい。
本発明は、したがって、
a) 一般式(I):
で表されるポリエーテルジアミン30〜70重量%、好ましくは、40〜60重量%;
b) 一般式R1-NH2[式中、R1は、5〜22個の炭素原子を有する炭化水素かまたは分子量400g/molまでを有する単官能性ポリエーテルアミンかの直鎖または分岐、飽和または、好ましくは、不飽和基である。]で表されるモノアミン3〜30重量%、好ましくは、5〜20重量%;
c) ジ-またはトリアミン3〜30重量%、好ましくは、5〜20重量%;および、
d) 一般式(II):
で表されるアルキルフェノール5〜40重量%、好ましくは、10〜30重量%;
を含む組成物に係る。
本発明に従うアミン組成物それら自体と硬化性組成物との両方は、公知のポリウレタンアミン類およびポリエーテルアミン付加体ならびにそれらから調製される硬化性組成物より実質的により低い粘度を有する。本発明に従う硬化性組成物を使用して得られる熱硬化性樹脂は、硬化完了後の優れた低温柔軟性が際立っている。
上記バインダーから出発して、充填弾性床カバー、埋め込み用樹脂および弾性化された接着剤ならびに弾性エポキシ樹脂/硬化剤発泡体を製造することもまた可能である。
実施例1:(本発明に従う)
液体密封亀裂面架橋膜の例
a) 51.75gのポリオキシプロピレンジアミンJeffamin R D 2000;
b) 9.14gのココナッツ脂肪アミン;
c) 9.14gのトリメチルヘキサメチレンジアミン(異性体混合物);および、
d) 26.73gのノニルフェノールおよび3.25gのトリス(2,4,4-ジメチルアミノメチル)フェノールを互いに混合する。粘度:275mPa・s;理論(Th.)アミン当量:約250。
WO 02/44240の実施例14に従う硬化剤。
粘度:約1000mPa・s;Th.アミン当量:約230。
Aradur R 76(高度に柔軟なバインダー用のHuntsmanからのポリエーテルポリアミン)
粘度:1500 mPa・s;Th.アミン当量:約250。
a) 51.75gのポリオキシプロピレンジアミンJeffamine D 2000;
b) 18.28gのココナッツ脂肪アミン;
d) 26.73gのノニルフェノールおよび3.25gのトリス(2,4,4-ジメチルアミノメチル)フェノールを互いに混合する。粘度:248 mPa・s;アミン当量:353。
a) 51.75gのポリオキシプロピレンJeffamine D 2000;
c) 18.28gのトリメチルヘキサメチレンジアミン(異性体混合物);
d) 26.73gのノニルフェノールおよび3.25gのトリス(2,4,4-ジメチルアミノメチル)フェノールを互いに混合する。粘度:320 mPa・s;アミン当量:178。
実施例1に対応するが、ノニルフェノールの代わりにスチレン化されたフェノールを含む組成物。粘度:260 mPa・s;アミン当量:250。
DE-A 2 200 717の実施例1a)に従う硬化剤:
a) 50gのココナッツ脂肪アミン;
b) 50gのトリメチルヘキサメチレンジアミン;および、
c) 147gのp-ノニルフェノールを互いに混合した。
使用例
各場合に:
131gの本実施例1からのアミン組成物、
122gのWO 02/44240 A1の実施例14(本実施例2)の硬化剤、
131gの硬化剤Aradur 76(本実施例3)、
185gの本実施例4からの硬化剤、
94gの本実施例5からの硬化剤、
131gの本実施例6からの硬化剤、および、
73gの本実施例7からの硬化剤、
の各々を、エポキシ価0.52当量/100g樹脂を有するジアン樹脂(ビスフェノールA)86重量%とエポキシ価0.33を有するC12-C14脂肪アルコールを基体とする長鎖単官能反応性希釈剤14重量%との混合物100gと完全に混合する。混合物は、ついで、約3mmの厚さで試験型に分布させる。室温で約24時間後、膜は、使用するのに適し、23℃で7日間(7dと略す)の硬化期間後、室温および-10℃で、以下の物理的値が測定される(表1参照):
表1から明らかなように、実施例1および6からの本発明に従う硬化剤は、それぞれ、比較的低い粘度275mPa・sおよび260 mPa・sを有する。さらに、実施例1および6からの硬化された熱硬化性樹脂は、室温(7d)にて、比較的高い引張強さと引裂抵抗性と合わさった伸び値を有する。-10℃にて、本発明に従う実施例は、驚くべきことに、なお、非常に高い伸び値を有するのに対して、他方、比較実施例の伸び値は、幾つかの場合に、実質的に減少した。特に比較実施例7(DE-A 2 200 717からの実施例1)にて、-10℃での伸び値は、特に鋭く減少した。伸び値におけるこのような減少は、本発明に従う硬化剤でさえ予想されるか、あるいは、より低い強さの値が、高い伸び値と合わさって予想されるであろう。この結果は、したがって、驚きであり、予想だにしえなかった。記載したような、ポリエーテルジアミン類、モノアミン類、ジアミン類およびアルキルフェノール類を含む本発明に従う組成物は、結果から明らかなように、また、さらなる比較実施例によって示されるように、非常に有益である。実施例4にて、硬化剤は、ジアミンまたはトリアミンなしで配合した。生成物は、なお、室温にて7d後でさえ、完全に硬化せず、したがって、工業的にほとんど使用することができない。実施例5にて、再度、硬化剤をジアミンと配合したが、モノアミンの添加はしなかった。硬化した熱硬化性樹脂の伸びは、特に、-10℃にて、比較的低い。
Claims (11)
- a) 一般式(I):
で表されるポリエーテルジアミン30〜70重量%;
b) 一般式R1−NH2
[式中、R1は、5〜22個の炭素原子を有する炭化水素または400g/molまでの分子量を有する単官能性ポリエーテルアミンである、直鎖または分岐、飽和または不飽和の基である]
で表されるモノアミン3〜30重量%;
c) イソホロンジアミン、アミノエチルピペラジン、キシリレンジアミンおよびトリメチルヘキサメチレンジアミンから選択されるジまたはトリアミン3〜30重量%;および、
d) 一般式(II):
で表されるアルキルフェノール5〜40重量%;
を含む組成物。 - a) 一般式(I)で表されるポリエーテルジアミン40〜60重量%;
b) 一般式R1−NH2で表されるモノアミン5〜20重量%;
c) ジまたはトリアミン5〜20重量%;および、
d) 一般式(II)で表されるアルキルフェノール10〜30重量%;
を含む、請求項1に記載の組成物。 - ポリエーテルアミンa)が、n=16〜40を有するポリオキシプロピレンジアミンであることを特徴とする、請求項1に記載の組成物。
- モノアミンb)が、8〜18個の炭素原子を有する脂肪アミンであることを特徴とする、請求項1に記載の組成物。
- モノアミンb)が、不飽和脂肪アミンであることを特徴とする、請求項4に記載の組成物。
- アルキルフェノールが、ノニルフェノールおよび/またはスチレン化されたフェノールである、請求項1に記載の組成物。
- アルキルフェノールが、スチレン化されたフェノールである、請求項6に記載の組成物。
- 平均で分子中に1つより多いエポキシ基を有するエポキシ化合物;硬化剤としての請求項1に記載の組成物;および、場合によっては、エポキシ樹脂技術にて慣用的な1つ以上の助剤および添加剤;を含む硬化性組成物。
- エポキシ化合物が、1価または多価フェノールを有するグリシジルエーテル類、4〜18個の炭素原子を有する1価または多価脂肪族アルコールを有するグリシジルエーテル類、ポリオキシアルキレングリコールを有するグリシジルエーテル類またはアルキレングリコールアルキルエーテルを有するグリシジルエーテル類から選択されるグリシジルエーテルであるか;または、直接エポキシ化によって製造されるエポキシ化合物である、請求項8に記載の硬化性組成物。
- エポキシ化合物が、ビスフェノールA樹脂;および/または、グリシジル化されたC12−C14アルコールを有するビスフェノールF樹脂を含むエポキシ樹脂混合物である、請求項9に記載の硬化性組成物。
- 造形された物品、塗膜および発泡体を製造するための、請求項8に記載の硬化性組成物の使用。
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