JP6211012B2 - ポリエーテルエステルポリオールおよび硬質ポリウレタンフォームを製造するためのその使用方法 - Google Patents
ポリエーテルエステルポリオールおよび硬質ポリウレタンフォームを製造するためのその使用方法 Download PDFInfo
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- JP6211012B2 JP6211012B2 JP2014559147A JP2014559147A JP6211012B2 JP 6211012 B2 JP6211012 B2 JP 6211012B2 JP 2014559147 A JP2014559147 A JP 2014559147A JP 2014559147 A JP2014559147 A JP 2014559147A JP 6211012 B2 JP6211012 B2 JP 6211012B2
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- polyol
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- polyols
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- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 2
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- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 10
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- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 10
- 229940073769 methyl oleate Drugs 0.000 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 description 9
- 150000001875 compounds Chemical class 0.000 description 9
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- 238000009472 formulation Methods 0.000 description 6
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- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
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- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
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- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 239000012971 dimethylpiperazine Substances 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 1
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 239000008169 grapeseed oil Substances 0.000 description 1
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- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- VQPKAMAVKYTPLB-UHFFFAOYSA-N lead;octanoic acid Chemical compound [Pb].CCCCCCCC(O)=O VQPKAMAVKYTPLB-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 240000004308 marijuana Species 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- OONVMEUUWGEINX-UHFFFAOYSA-N n,n-dimethyl-2-piperidin-1-ylethanamine Chemical compound CN(C)CCN1CCCCC1 OONVMEUUWGEINX-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- HQXQMGOSPPGTGC-UHFFFAOYSA-N n-cyclohexyl-4,4-dimethylcyclohexan-1-amine Chemical compound C1CC(C)(C)CCC1NC1CCCCC1 HQXQMGOSPPGTGC-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
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- 229940049964 oleate Drugs 0.000 description 1
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- 235000008390 olive oil Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
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- 239000012188 paraffin wax Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000010471 pistachio oil Substances 0.000 description 1
- 229940082415 pistachio oil Drugs 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 235000013849 propane Nutrition 0.000 description 1
- 239000008171 pumpkin seed oil Substances 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
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- 238000005057 refrigeration Methods 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229940066675 ricinoleate Drugs 0.000 description 1
- WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
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- 235000011803 sesame oil Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000005628 tolylene group Chemical group 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- CWBIFDGMOSWLRQ-UHFFFAOYSA-N trimagnesium;hydroxy(trioxido)silane;hydrate Chemical compound O.[Mg+2].[Mg+2].[Mg+2].O[Si]([O-])([O-])[O-].O[Si]([O-])([O-])[O-] CWBIFDGMOSWLRQ-UHFFFAOYSA-N 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- ZYMLPCYLTMMPQE-UHFFFAOYSA-J tris(2,2-diethylhexanoyloxy)stannyl 2,2-diethylhexanoate Chemical compound [Sn+4].CCCCC(CC)(CC)C([O-])=O.CCCCC(CC)(CC)C([O-])=O.CCCCC(CC)(CC)C([O-])=O.CCCCC(CC)(CC)C([O-])=O ZYMLPCYLTMMPQE-UHFFFAOYSA-J 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000008170 walnut oil Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 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
- C08G18/28—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
- C08G18/36—Hydroxylated esters of higher fatty acids
-
- 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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- C08G18/40—High-molecular-weight compounds
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- C08G18/4804—Two or more polyethers of different physical or chemical nature
- C08G18/482—Mixtures of polyethers containing at least one polyether containing nitrogen
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/284—Compounds containing ester groups, e.g. oxyalkylated monocarboxylic acids
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- 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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- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4244—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups
-
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- 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
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- C08G18/40—High-molecular-weight compounds
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- C08G18/487—Polyethers containing cyclic groups
- C08G18/4883—Polyethers containing cyclic groups containing cyclic groups having at least one oxygen atom in the ring
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G18/5027—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups directly linked to carbocyclic groups
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- 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
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Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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Description
a1)5から63質量%の、2.5から8の平均官能基数を有する、1種または複数のポリオールもしくはポリアミンまたはこれらの混合物と、
a2)2から50質量%の、1種または複数の脂肪酸、脂肪酸モノエステルまたはこれらの混合物と、
a3)35から70質量%の、炭素原子2から4個の1種または複数のアルキレンオキシドと
の反応生成物を含むポリエーテルエステルポリオールによって達成されることを見い出した。
A)有機もしくは変性有機ポリイソシアナートまたはこれらの混合物と、
B)1種または複数の本発明のポリエーテルエステルポリオールと、
C)場合によりポリエステルポリオールと、
D)場合によりポリエーテルオールポリオールと、
E)1種または複数の発泡剤と、
F)触媒と、
G)場合により他の助剤および/または添加剤と
の反応によって硬質ポリウレタンフォームを製造する方法をさらに提供する。
B)1種または複数のポリエーテルエステルポリオール、
C)場合によりポリエステルポリオール、
D)場合によりポリエーテルポリオール、
E)1種または複数の発泡剤、
F)触媒、および
G)場合により他の助剤および/または添加剤
を含むポリオール混合物を提供する。
40から100質量%のポリエーテルエステルポリオールB)、
0質量%の他のポリエステルポリオールC)、
5から40質量%のポリエーテルポリオールD)、
10から25質量%の発泡剤E)、
1.0から3質量%の触媒F)、および
1から4質量%の助剤および/または添加剤G)
を含み、
ここで、成分B)およびD)からG)は、合計すると100質量%になる。
50から80質量%のポリエーテルエステルポリオールB)、
0質量%の他のポリエステルポリオールC)、
5から30質量%のポリエーテルポリオールD)、
10から20質量%の発泡剤E)、
1.0から2.5質量%の触媒F)、および
1.5から3質量%の他の助剤および/または添加剤G)
を含むことがより好ましく、ここで、成分B)およびD)からG)は、合計すると100質量%になる。
ペンタン溶解度
ペンタン溶解度が測定される成分に、ペンタンを斬増的に添加することによって、ペンタン溶解度を決定した。ペンタンを、試験をする正確に100gの成分に、起こり得るペンタン溶解度に従って添加し、成分と混合した。混合物が濁ってもおらず、2つの相も持たない場合、さらなるペンタンを添加し、再度混合することになる。
慣用のポリオールに対する本発明のポリエーテルエステルポリオールのペンタン相溶性
450のOH価および5.0の官能基数を有するスクロース/グリセロール/POポリオールが、比較ポリオールとしての機能を果たす。本発明の実施例は、出発材料スクロース/グリセロール/POに加えて、提示された割合(質量%単位)の脂肪酸または脂肪酸エステルを有する。
以下の成分を反応させた(すべての個々の項目は質量%単位)。
糖20.04%、グリセロール12.7%、PO41.2%、オレイン酸メチル25.6%からのポリオールB、OH価489mgKOH/g;
ビシナルTDA24.9%、PO75.1%からのポリオールC、OH価400mgKOH/g;
ビシナルTDA9.2%、EO8.6%、PO82.2からのポリオールD、OH価160mgKOH/g;
ポリオールEは、スクロース、グリセロールおよびプロピレンオキシドをベースとし、KOHで触媒されたポリエーテルオールであり、5.1の官能基数および450mgKOH/gのOH価を有する;
安定剤1:シリコーン含有泡安定剤(Evonik製Tegostab(登録商標)B8474)
安定剤2:シリコーン含有泡安定剤(Evonik製Tegostab(登録商標)B8491)
触媒1:ジメチルジシクロヘキシルアミン(DMCHA)
触媒2:ペンタメチルジエチレントリアミン(PMDETA)
触媒3:N,N,N−トリスジメチルアミノプロピルヘキサヒドロトリアジン
触媒4:ジメチルベンジルアミン
イソシアナート:31.5質量%のNCO含量を有するポリマーMDI(Lupranat(登録商標)M20)
20.2gのグリセロール、0.1gのイミダゾール、50.8gのスクロースならびに11.5gのオレイン酸メチルを最初に、25℃で300mlの反応器に投入した。次いで、反応器を窒素で不活性化した。ケトルを130℃まで加熱し、147.5gのプロピレンオキシドを計量供給した。9時間の反応時間後に、ケトルを100℃で30分間十分排気し、次いで25℃まで冷却して、217gの生成物を得た。
粘度(25℃):11324mPas
酸価:0.01mgKOH/g未満
水含量:0.01%未満
オレイン酸メチルによるポリエーテルエステルの製造
20.2gのグリセロール、0.1gのイミダゾール、50.8gのスクロースならびに27.6gのオレイン酸メチルを最初に、25℃で300mlの反応器に投入した。次いで、反応器を窒素で不活性化した。ケトルを130℃まで加熱し、131.4gのプロピレンオキシドを計量供給した。5時間の反応時間の後に、ケトルを100℃で40分間十分排気し、次いで25℃まで冷却して、219gの生成物を得た。
粘度(25℃):9453mPas
酸価:0.05mgKOH/g
水含量:0.04%
オレイン酸メチルによるポリエーテルエステルの製造
477.9gのグリセロール、2.5gのイミダゾール、1250.2gのスクロースならびに1250.2gのオレイン酸メチルを最初に、25℃で5Lの反応器に投入した。次いで、反応器を窒素で不活性化した。ケトルを130℃まで加熱し、2068.5gのプロピレンオキシドを計量供給した。3.5時間の反応時間の後に、ケトルを100℃で60分間十分排気し、次いで25℃まで冷却して、4834.8gの生成物を得た。
粘度(25℃):11892mPas
酸価:0.17mgKOH/g
水含量:0.021%
オレイン酸によるポリエーテルエステルの製造
14.9gのグリセロール、0.1gのイミダゾール、56.4gのスクロースならびに11.6gのオレイン酸を最初に、25℃で300mLの反応器に投入した。次いで、反応器を窒素で不活性化した。ケトルを130℃まで加熱し、147.1gのプロピレンオキシドを計量供給した。7時間の反応時間の後に、ケトルを100℃で40分間十分排気し、次いで25℃まで冷却して、216.9gの生成物を得た。
粘度(25℃):20212mPas
酸価:0.01mgKOH/g未満
水含量:0.01%未満
オレイン酸によるポリエーテルエステルの製造
244.4gのグリセロール、2.5gのイミダゾール、1309.5gのスクロースならびに425.1gのオレイン酸を最初に、25℃で5Lの反応器に投入した。次いで、反応器を窒素で不活性化した。ケトルを130℃まで加熱し、3019.1gのプロピレンオキシドを計量供給した。4.5時間の反応時間の後に、ケトルを100℃で40分間十分排気し、次いで25℃まで冷却して、4926.8gの生成物を得た。
粘度(25℃):20477mPas
酸価:0.01mgKOH/g未満
水含量:0.03%未満
オレイン酸によるポリエーテルエステルの製造
7.7gのグリセロール、0.1gのイミダゾール、64.0gのスクロースならびに27.6gのオレイン酸を最初に、25℃で300mLの反応器に投入した。次いで、反応器を窒素で不活性化した。ケトルを130℃まで加熱し、130.6gのプロピレンオキシドを計量供給した。7時間の反応時間の後に、ケトルを100℃で30分間十分排気し、次いで25℃まで冷却して、211.9gの生成物を得た。
粘度(25℃):41321mPas
酸価:0.13mgKOH/g未満
水含量:0.01%未満
オレイン酸メチルによるポリエーテルエステルの製造
50.7kgのグリセロール、0.2kgのイミダゾール、81.8kgのスクロースならびに102.4kgのオレイン酸メチルを最初に、25℃で600Lの反応器に投入した。次いで、反応器を窒素で不活性化した。ケトルを120℃まで加熱し、165.0kgのプロピレンオキシドを計量供給した。4時間の反応時間の後に、ケトルを120℃で30分間十分排気し、次いで25℃まで冷却して、377.0kgの生成物を得た。
粘度(25℃):8783mPas
酸価:0.01mgKOH/g未満
水含量:0.01%未満
オレイン酸によるポリエーテルエステルの製造
25.9kgのグリセロール、0.2kgのイミダゾール、98.0kgのスクロースならびに20.1kgのオレイン酸を最初に、25℃で600Lの反応器に投入した。次いで、反応器を窒素で不活性化した。ケトルを120℃まで加熱し、255.8kgのプロピレンオキシドを計量供給した。1時間の反応時間の後に、ケトルを120℃で30分間十分排気し、次いで25℃まで冷却して、390.0kgの生成物を得た。
粘度(25℃):17367mPas
酸価:0.01mgKOH/g未満
水含量:0.01%未満
Claims (10)
- a1)20から50質量%の、2.5から8の平均官能基数を有する、1種または複数のポリオールと、
a2)5から30質量%の、1種または複数の脂肪酸モノエステルと、
a3)35から50質量%の、炭素原子が2から4個の1種または複数のアルキレンオキシドと
の反応生成物を含み、
成分a1)のポリオールが、糖、ペンタエリトリトール、ソルビトール、トリメチロールプロパン、グリセロール、トリレンジアミン、エチレンジアミン、エチレングリコール、プロピレングリコールおよび水からなる群から選択され、及び
成分a2)が、オレイン酸、ステアリン酸、パルミチン酸、リノレン酸のモノエステルから成る群から選ばれることを特徴とするポリエーテルエステルポリオール。 - 前記成分a1)が、グリセロールとスクロースの混合物を含む、請求項1に記載のポリエーテルエステルポリオール。
- 成分a3)のアルキレンオキシドが、プロピレンオキシドである、請求項1又は2に記載のポリエーテルエステルポリオール。
- 300から800mgKOH/gのOH価を有する、請求項1から3のいずれか一項に記載のポリエーテルエステルポリオール。
- 2.5から8の官能基数を有する、請求項1から4のいずれか一項に記載のポリエーテルエステルポリオール。
- A)有機もしくは変性有機ポリイソシアナートまたはこれらの混合物と、
B)請求項1から5のいずれか一項に記載の1種または複数のポリエーテルエステルポリオールと、
C)場合により他のポリエステルポリオールと、
D)場合によりポリエーテルオールポリオールと、
E)1種または複数の発泡剤と、
F)触媒と、
G)場合により他の助剤および/または添加剤と
の反応によって硬質ポリウレタンフォームを製造する方法。 - 成分として
B)請求項1から5のいずれか一項に記載の1種または複数のポリエーテルエステルポリオール、
C)場合によりポリエステルポリオール、
D)場合によりポリエーテルオールポリオール、
E)1種または複数の発泡剤、
F)触媒、および
G)場合により他の助剤および/または添加剤
を含むポリオール混合物。 - 50から80質量%のポリエーテルエステルポリオールB)、
5から30質量%のポリエーテルポリオールD)、
10から20質量%の発泡剤E)、
1.0から2.5質量%の触媒F)、
1.5から3質量%の他の助剤および/または添加剤G)
を含み、ここで、成分B)およびD)からG)は、合計すると100質量%になる、請求項7に記載のポリオール混合物。 - さらなるポリエステルポリオールC)を含まない、請求項7または8に記載のポリオール混合物。
- ポリエーテルポリオールD)としてプロポキシル化トリレンジアミンを含む、請求項7から9のいずれか一項に記載のポリオール混合物。
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CA2931931C (en) | 2013-11-29 | 2022-11-01 | Basf Se | Polyurethane system with long pot life and rapid hardening |
CN103897200B (zh) * | 2014-03-31 | 2016-05-11 | 东南大学 | 一种制备聚氨酯聚合物网络的方法 |
CA2986802A1 (en) | 2015-05-27 | 2016-12-01 | Basf Se | Use of a composition for stabilizing a geological formation in oil fields, gas fields, water pumping fields, mining or tunnel constructions |
EP3334771B1 (en) | 2015-08-10 | 2019-07-31 | Construction Research & Technology GmbH | Process for producing a ring-opening polymerization product |
PL3368584T3 (pl) | 2015-10-28 | 2020-12-14 | Basf Se | Polieteroestry i ich zastosowanie do wytwarzania sztywnych poliuretanowych tworzyw piankowych |
DE102016122276A1 (de) | 2016-11-18 | 2018-05-24 | H & S Anlagentechnik Gmbh | Recyclingpolyol |
WO2020165135A1 (en) | 2019-02-11 | 2020-08-20 | Basf Se | Acrylic copolymer capsule designed to open up at < 90°c for controlled release of in-situ forming pu/pir catalyst |
CN110218293B (zh) * | 2019-06-26 | 2021-07-23 | 山东宏鑫源钢板有限公司 | 铝镁锰聚氨酯屋面板及其制备工艺 |
WO2020260235A1 (en) * | 2019-06-28 | 2020-12-30 | Basf Se | Polyol component and use thereof for the production of rigid polyurethane foams |
CN110591047A (zh) * | 2019-09-10 | 2019-12-20 | 华南理工大学 | 一种可降解聚醚型聚氨酯及其制备方法 |
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