JP4199384B2 - オレフィン変性ポリオール及びその製造方法 - Google Patents
オレフィン変性ポリオール及びその製造方法 Download PDFInfo
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- JP4199384B2 JP4199384B2 JP25826199A JP25826199A JP4199384B2 JP 4199384 B2 JP4199384 B2 JP 4199384B2 JP 25826199 A JP25826199 A JP 25826199A JP 25826199 A JP25826199 A JP 25826199A JP 4199384 B2 JP4199384 B2 JP 4199384B2
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- Prior art keywords
- olefin
- modified
- compound
- polyol
- weight
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- 229920005862 polyol Polymers 0.000 title claims description 226
- 238000004519 manufacturing process Methods 0.000 title claims description 24
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- -1 phosphazene compound Chemical class 0.000 claims description 124
- 150000001875 compounds Chemical class 0.000 claims description 71
- 238000012644 addition polymerization Methods 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 44
- 239000003054 catalyst Substances 0.000 claims description 39
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 150000007514 bases Chemical class 0.000 claims description 17
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 14
- 239000005977 Ethylene Substances 0.000 claims description 14
- 239000004711 α-olefin Substances 0.000 claims description 14
- 229920001577 copolymer Polymers 0.000 claims description 12
- 150000001336 alkenes Chemical class 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 8
- 238000010559 graft polymerization reaction Methods 0.000 claims description 6
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 4
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- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 46
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 41
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- 230000007423 decrease Effects 0.000 description 18
- 239000003463 adsorbent Substances 0.000 description 16
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 8
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- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical class CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
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- 239000004698 Polyethylene Substances 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 5
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
- 239000000391 magnesium silicate Substances 0.000 description 4
- 229910052919 magnesium silicate Inorganic materials 0.000 description 4
- 235000019792 magnesium silicate Nutrition 0.000 description 4
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 4
- 239000002685 polymerization catalyst Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 3
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229920005830 Polyurethane Foam Polymers 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
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- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
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- 239000000395 magnesium oxide Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- JHSPKDZISQMYPX-UHFFFAOYSA-N n-[bis[[tris(dimethylamino)-$l^{5}-phosphanylidene]amino]phosphorylimino-bis(dimethylamino)-$l^{5}-phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(N(C)C)(N(C)C)=NP(=O)(N=P(N(C)C)(N(C)C)N(C)C)N=P(N(C)C)(N(C)C)N(C)C JHSPKDZISQMYPX-UHFFFAOYSA-N 0.000 description 3
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- 229920006395 saturated elastomer Polymers 0.000 description 1
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- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- STOAEWOKLCPIFX-UHFFFAOYSA-N tetrakis[[tris(dimethylamino)-$l^{5}-phosphanylidene]amino]phosphanium Chemical compound CN(C)P(N(C)C)(N(C)C)=N[P+](N=P(N(C)C)(N(C)C)N(C)C)(N=P(N(C)C)(N(C)C)N(C)C)N=P(N(C)C)(N(C)C)N(C)C STOAEWOKLCPIFX-UHFFFAOYSA-N 0.000 description 1
- NYTYWTQXLWNFFQ-UHFFFAOYSA-M tetrakis[[tris(dimethylamino)-$l^{5}-phosphanylidene]amino]phosphanium;chloride Chemical compound [Cl-].CN(C)P(N(C)C)(N(C)C)=N[P+](N=P(N(C)C)(N(C)C)N(C)C)(N=P(N(C)C)(N(C)C)N(C)C)N=P(N(C)C)(N(C)C)N(C)C NYTYWTQXLWNFFQ-UHFFFAOYSA-M 0.000 description 1
- GLBZKFGGCHCGAG-UHFFFAOYSA-M tetrakis[[tris(dimethylamino)-$l^{5}-phosphanylidene]amino]phosphanium;hydroxide Chemical compound [OH-].CN(C)P(N(C)C)(N(C)C)=N[P+](N=P(N(C)C)(N(C)C)N(C)C)(N=P(N(C)C)(N(C)C)N(C)C)N=P(N(C)C)(N(C)C)N(C)C GLBZKFGGCHCGAG-UHFFFAOYSA-M 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000009849 vacuum degassing Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
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- Compositions Of Macromolecular Compounds (AREA)
- Polyethers (AREA)
- Polyurethanes Or Polyureas (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25826199A JP4199384B2 (ja) | 1999-09-13 | 1999-09-13 | オレフィン変性ポリオール及びその製造方法 |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25826199A JP4199384B2 (ja) | 1999-09-13 | 1999-09-13 | オレフィン変性ポリオール及びその製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2001081183A JP2001081183A (ja) | 2001-03-27 |
| JP2001081183A5 JP2001081183A5 (https=) | 2006-06-29 |
| JP4199384B2 true JP4199384B2 (ja) | 2008-12-17 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP25826199A Expired - Fee Related JP4199384B2 (ja) | 1999-09-13 | 1999-09-13 | オレフィン変性ポリオール及びその製造方法 |
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| Country | Link |
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| JP (1) | JP4199384B2 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020041139A (ja) * | 2018-09-11 | 2020-03-19 | 国立大学法人神戸大学 | エーテル誘導体の製造方法 |
| JP2025078318A (ja) * | 2023-11-08 | 2025-05-20 | 東洋アルミニウム株式会社 | 効果顔料調製物、効果顔料調製物を含む熱可塑性樹脂組成物および効果顔料調製物を含む塗料又はインキの製造方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6015409A (ja) * | 1983-07-07 | 1985-01-26 | Sumitomo Chem Co Ltd | ポリウレタンとポリオレフィンの接着方法 |
| JPS61126120A (ja) * | 1984-11-22 | 1986-06-13 | Mitsui Petrochem Ind Ltd | 液状変性エチレン系ランダム共重合体 |
| DE3622825A1 (de) * | 1986-07-08 | 1988-01-21 | Bayer Ag | Poly-(alpha)-alkyl-olefin-/ polyurethan-blockcopolymere, verfahren zu ihrer herstellung und ihre verwendung |
| JP2993060B2 (ja) * | 1990-06-29 | 1999-12-20 | 宇部興産株式会社 | ポリプロピレン樹脂組成物 |
| JPH0468015A (ja) * | 1990-07-10 | 1992-03-03 | Ube Ind Ltd | ポリプロピレン樹脂組成物 |
| JP3703261B2 (ja) * | 1997-08-19 | 2005-10-05 | 三井化学株式会社 | ケイ素基含有ポリアルキレンオキサイド重合体の製造方法及び湿気硬化性組成物 |
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| JP2001081183A (ja) | 2001-03-27 |
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