JP2012527508A - 二種のポリエーテルアミンと一種のプレポリマーから製造できるポリ尿素 - Google Patents
二種のポリエーテルアミンと一種のプレポリマーから製造できるポリ尿素 Download PDFInfo
- Publication number
- JP2012527508A JP2012527508A JP2012511279A JP2012511279A JP2012527508A JP 2012527508 A JP2012527508 A JP 2012527508A JP 2012511279 A JP2012511279 A JP 2012511279A JP 2012511279 A JP2012511279 A JP 2012511279A JP 2012527508 A JP2012527508 A JP 2012527508A
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- JP
- Japan
- Prior art keywords
- component
- amine
- polyurea
- catalyst
- pep1
- 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.)
- Granted
Links
- 229920002396 Polyurea Polymers 0.000 title claims abstract description 56
- 229920005862 polyol Polymers 0.000 claims abstract description 76
- 150000003077 polyols Chemical class 0.000 claims abstract description 76
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 49
- 229920000570 polyether Polymers 0.000 claims abstract description 49
- 150000001412 amines Chemical class 0.000 claims abstract description 43
- 239000012948 isocyanate Substances 0.000 claims abstract description 27
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 25
- 239000004970 Chain extender Substances 0.000 claims abstract description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 91
- 239000003054 catalyst Substances 0.000 claims description 52
- 238000004519 manufacturing process Methods 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- -1 polyoxypropylene Polymers 0.000 claims description 20
- 229920001451 polypropylene glycol Polymers 0.000 claims description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 13
- 239000007921 spray Substances 0.000 claims description 13
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical group C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 11
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 4
- 239000002131 composite material Substances 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 238000013329 compounding Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 9
- 229920001971 elastomer Polymers 0.000 description 9
- 239000000806 elastomer Substances 0.000 description 9
- 239000003999 initiator Substances 0.000 description 9
- 125000003277 amino group Chemical group 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- 230000021736 acetylation Effects 0.000 description 6
- 238000006640 acetylation reaction Methods 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 150000003141 primary amines Chemical class 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 5
- 238000005576 amination reaction Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 description 3
- RQEOBXYYEPMCPJ-UHFFFAOYSA-N 4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N RQEOBXYYEPMCPJ-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- MBAUOPQYSQVYJV-UHFFFAOYSA-N octyl 3-[4-hydroxy-3,5-di(propan-2-yl)phenyl]propanoate Chemical compound OC1=C(C=C(C=C1C(C)C)CCC(=O)OCCCCCCCC)C(C)C MBAUOPQYSQVYJV-UHFFFAOYSA-N 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 239000003380 propellant Substances 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 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 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 description 1
- FRCHKSNAZZFGCA-UHFFFAOYSA-N 1,1-dichloro-1-fluoroethane Chemical compound CC(F)(Cl)Cl FRCHKSNAZZFGCA-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 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 description 1
- ZYCRBOCGBKATBL-UHFFFAOYSA-N 3-tert-butyl-6-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(C(C)(C)C)C(N)=C1N ZYCRBOCGBKATBL-UHFFFAOYSA-N 0.000 description 1
- AOFIWCXMXPVSAZ-UHFFFAOYSA-N 4-methyl-2,6-bis(methylsulfanyl)benzene-1,3-diamine Chemical compound CSC1=CC(C)=C(N)C(SC)=C1N AOFIWCXMXPVSAZ-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- IIGAAOXXRKTFAM-UHFFFAOYSA-N N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C Chemical compound N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C IIGAAOXXRKTFAM-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical group OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 229920003226 polyurethane urea Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 238000010107 reaction injection moulding Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- BGXXXYLRPIRDHJ-UHFFFAOYSA-N tetraethylmethane Chemical compound CCC(CC)(CC)CC BGXXXYLRPIRDHJ-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4866—Polyethers having a low unsaturation value
-
- 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
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-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/185—Catalysts containing secondary or tertiary amines or salts thereof having cyano groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G18/3225—Polyamines
- C08G18/3237—Polyamines aromatic
- C08G18/324—Polyamines aromatic containing only one aromatic ring
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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- C08G18/48—Polyethers
- C08G18/4825—Polyethers containing two 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
- C08G18/28—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
- C08G18/50—Polyethers having heteroatoms other than oxygen
-
- 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
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- C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups
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- 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
- C08L75/02—Polyureas
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/02—Polyureas
-
- 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
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/50—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing nitrogen, e.g. polyetheramines or Jeffamines(r)
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Abstract
a)
a1)5〜40重量%の少なくとも一種の、少なくとも一種のポリエーテルポリオール1(PEP1)と少なくとも一種のアミン1とから得られるポリエーテルアミン1(PEA1)(ただし、PEP1の等価質量は≦500)と、
a2)30〜90重量%の少なくとも一種の、少なくとも一種のポリエーテルポリオール2(PEP2)と少なくとも一種のアミン2から得られるポリエーテルアミン2(PEA2)(ただし、PEP2の等価質量は>500)と、
a3)5〜30重量%の少なくとも一種のアミン鎖延長剤と、含む成分Aと、
b)
b1)少なくとも一種のポリエーテルポリオール(PEP3)及び
b2)少なくとも一種のイソシアネートと、から得られる、
プレポリマーである成分Bと、
から製造されるポリ尿素に関する。
【選択図】なし
Description
a)
a1)5〜40重量%の少なくとも一種の、少なくとも一種のポリエーテルポリオール1(PEP1)と少なくとも一種のアミン1とから得られるポリエーテルアミン1(PEA1)(ただし、PEP1の等価質量は≦500)と、
a2)30〜90重量%の少なくとも一種の、少なくとも一種のポリエーテルポリオール2(PEP2)と少なくとも一種のアミン2から得られるポリエーテルアミン2(PEA2)(ただし、PEP2の等価質量は>500)と、
a3)5〜30重量%の少なくとも一種のアミン鎖延長剤とからなる成分Aと
b)
b1)少なくとも一種のポリエーテルポリオール(PEP3)と
b2)少なくとも一種のイソシアネートとから得られるプレポリマーである
成分Bとから製造されるポリ尿素により達成される。
等価質量:56100をOH価で割った数値に相当する
分子量:公称官能価×等価質量
イソシアネート指数:イソシアネート使用量をイソシアネートの理論量で割り、100倍した値
不飽和数:ポリオール(ポリエーテルポリオール)中の不飽和末端基(例えばアリル)の
濃度の指標。1グラムのポリオール中の不飽和種に一致するミリ等価質量で表す。単位:meq/g
総アセチル化能:反応性基(−OH、−NH−、−NH2)の濃度の指標。1グラムのポリエーテルアミン中に存在する反応性基に一致するKOHのmg数で表す。単位:mg−KOH/g
総アミン価(アミン数):アミノ基(第三級と第二級と及び第一級のアミノ基)の濃度の指標。1グラムのポリエーテルアミン中に存在する反応性基と一致するKOHのmg数で表す。単位:mg−KOH/g
アミノ化率:[総アセチル化能/総アミン価]×100%
公称官能価:開始剤分子(開始剤)の官能価に相当
成分a2)は、少なくとも一種のポリエーテルポリオール2(PEP2)と少なくとも一種のアミン2から製造される、少なくとも一種のポリエーテルアミン2(PEA2)であり、PEP2の等価質量は>500である。
a)
a1)5〜40重量%の少なくとも一種の、少なくとも一種のポリエーテルポリオール1(PEP1)と少なくとも一種のアミン1とから得られるポリエーテルアミン1(PEA1)と(ただし、PEP1の等価質量は≦500で、PEP1の製造にアルカリ金属の水酸化物触媒(MOH触媒)が、特に水酸化カリウム触媒(KOH触媒)が用いられる)と
a2)30〜90重量%の少なくとも一種の、少なくとも一種のポリエーテルポリオール2(PEP2)と少なくとも一種のアミン2から得られるポリエーテルアミン2(PEA2)(ただし、PEP2の等価質量は>500で、PEP2の製造に二金属シアン化物複合触媒(DMC触媒)が用いられる)と
a3)5〜30重量%の少なくとも一種のアミン鎖延長剤とからなる成分Aと、
b)
b1)少なくとも一種のポリエーテルポリオール(PEP3)で(PEP3の等価質量が>500であり、PEP3の製造にDMC触媒が使用されている)と
b2)少なくとも一種のイソシアネート徒から得られるプレポリマーである
成分Bとから製造されるポリ尿素に関する。
ポリオール1(KOH触媒による):
合成は、洗浄乾燥後の10リットルの攪拌オートクレーブ中で行なう。0.525kgのジプロピレングリコールと0.034kgの47.5%KOH水溶液を、この攪拌反応器に投入する。この反応器の内部を窒素で不活性化させ、減圧下で120℃で合計1時間処理して水分濃度が約0.02%となるまで乾燥させる。次いで、6.167kgのプロピレンオキシドを4時間かけて投入する。投入完了後、混合物を定圧となるまで攪拌し、この反応混合物を105℃、10mbarで脱気させる。得られる生成物のOH価は59mg−KOH/gであり、これを500ppmのイルガノックス1135を酸化防止剤として用いて処理した後、他の用途に使用した。ポリオール1の不飽和数は0.048meq/gであり、その等価質量は950であった。
合成は、洗浄乾燥後の10リットルの攪拌オートクレーブ中で、DE102004047406の実施例1に準じて行なう。1.833kgの出発化合物をこの攪拌反応器に入れ、EP0862947の実施例1に準じて界面活性剤の存在下で、125ppmの酢酸亜鉛とヘキサシアノコバルト酸から合成した多金属シアン化物化合物で処理する。この出発化合物は、KOH触媒で合成し次いで塩基触媒を除いて得た二官能性プロピレングリコールプロポキシラートであり、そのOH価は240mg−KOH/gである。
合成は、洗浄乾燥後の10リットルの攪拌オートクレーブ中で行なう。2.56kgのジプロピレングリコールと0.034kgの47.5%のKOH水溶液を、この攪拌反応器に入れる。反応器の内部を窒素で不活性化し、減圧下120℃で合計1時間処理し、水分濃度が約0.02%となるまで乾燥させる。次いで、5.344kgのプロピレンオキシドを4時間かけて投入する。投入完了後、この混合物を定圧となるまで混合し、この反応混合物を105℃、10mbarで脱気させる。得られる生成物のOH価は278mg−KOH/gであり、これを500ppmのイルガノックス1135を酸化防止剤として用いて処理してから、他の用途に用いる。ポリオール3の不飽和数は0.004meq/gであり、その等価質量は200である。
本実施例においては、末端1級アミン基をもつポリオキシプロピレンジアミンを合成する。これらのポリエーテルアミンは、実施例1のポリオキシプロピレンポリエーテルポリオールを、遷移金属触媒の存在下、高温高圧下でアンモニアと水素に曝す方法により合成する。このアミノ化プロセスでは主に1級アミン基が合成されるため、第二級アミンと第三級アミンの含量はアミン含量の1%未満である。
プレポリマー1を、MDIとポリオキシプロピレンポリエーテルポリオール(実施例1のポリオール1)から合成する。このMDIは、いずれの場合も、最高で50重量%の2,4’−異性体と4,4’−異性体(51.0重量%)を含む。ポリオール1の公称官能価は2であり、OH価は59mg−KOH/gである。このポリマーは、触媒としてKOHの存在下(49重量%)で合成されたものである。ポリオール1の不飽和数は0.048meq/gであり、その等価質量は950である。
下の例では、用いるA成分が、以下の成分からなる基本配合物である。
ポリエーテルアミン1:PPDA3、最高で17.05重量%
アミン鎖延長剤:エタキュア100〜19.85重量%
Claims (10)
- a)
a1)5〜40重量%の少なくとも一種の、少なくとも一種のポリエーテルポリオール1(PEP1)と少なくとも一種のアミン1とから得られるポリエーテルアミン1(PEA1)と(ただし、PEP1の等価質量は≦500)
a2)30〜90重量%の少なくとも一種の、少なくとも一種のポリエーテルポリオール2(PEP2)と少なくとも一種のアミン2から得られるポリエーテルアミン2(PEA2)(ただし、PEP2の等価質量は>500)と、
a3)5〜30重量%の少なくとも一種のアミン鎖延長剤と、を含む成分Aと、
b)
b1)少なくとも一種のポリエーテルポリオール(PEP3)及び
b2)少なくとも一種のイソシアネートとから得られる、
プレポリマーである成分Bと、
から製造されるポリ尿素。 - ポリ尿素が噴霧組成物である請求項1に記載のポリ尿素。
- PEP2の製造に二金属シアン化物複合触媒(DMC触媒)が用いられる請求項1または2に記載のポリ尿素。
- PEP3の製造にDMC触媒が用いられる請求項1〜3のいずれか一項に記載のポリ尿素。
- PEP1の製造に、アルカリ金属の水酸化物触媒(MOH触媒)、特に水酸化カリウム触媒(KOH触媒)が用いられる請求項1〜4のいずれか一項に記載のポリ尿素。
- アミン1及び/又はアミン2がアンモニアである請求項1〜5のいずれか一項に記載のポリ尿素。
- PEP1、PEP2及び/又はPEP3がポリオキシプロピレンポリエーテルポリオールである請求項1〜6のいずれか一項に記載のポリ尿素。
- イソシアネートがジフェニルメタンジイソシアネート(MDI)である請求項1〜7のいずれか一項に記載のポリ尿素。
- 少なくとも一種の成分Aが少なくとも一種の成分Bと反応させられることを特徴とする請求項1〜8のいずれか一項に記載のポリ尿素の製造方法。
- 噴霧配合方法である請求項9に記載の方法。
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CN102428117A (zh) | 2012-04-25 |
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