JP2005511873A - モノマー含有量の少ないポリウレタン−プレポリマーの製造方法 - Google Patents
モノマー含有量の少ないポリウレタン−プレポリマーの製造方法 Download PDFInfo
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- JP2005511873A JP2005511873A JP2003552827A JP2003552827A JP2005511873A JP 2005511873 A JP2005511873 A JP 2005511873A JP 2003552827 A JP2003552827 A JP 2003552827A JP 2003552827 A JP2003552827 A JP 2003552827A JP 2005511873 A JP2005511873 A JP 2005511873A
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- JP
- Japan
- Prior art keywords
- polyol
- diisocyanate
- polyurethane
- prepolymer
- acid
- 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.)
- Pending
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- 229920001730 Moisture cure polyurethane Polymers 0.000 title claims abstract description 52
- 239000000178 monomer Substances 0.000 title claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- 229920005862 polyol Polymers 0.000 claims abstract description 74
- 150000003077 polyols Chemical class 0.000 claims abstract description 72
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 51
- 238000000034 method Methods 0.000 claims abstract description 35
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 29
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 29
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 27
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 24
- 230000008569 process Effects 0.000 claims abstract description 19
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- 239000004831 Hot glue Substances 0.000 claims abstract description 4
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- 229920000570 polyether Polymers 0.000 claims description 33
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 24
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 claims description 22
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 21
- 229920005906 polyester polyol Polymers 0.000 claims description 20
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 12
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- 239000004823 Reactive adhesive Substances 0.000 claims description 3
- 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 claims description 3
- 238000004382 potting Methods 0.000 claims 1
- 239000006227 byproduct Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000013466 adhesive and sealant Substances 0.000 abstract 1
- -1 aromatic primary amines Chemical class 0.000 description 34
- 239000004814 polyurethane Substances 0.000 description 27
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- 150000001875 compounds Chemical class 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000012948 isocyanate Substances 0.000 description 17
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 13
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- 230000001070 adhesive effect Effects 0.000 description 13
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 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 11
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 9
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000000010 aprotic solvent Substances 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
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- 150000001991 dicarboxylic acids Chemical class 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 238000013329 compounding Methods 0.000 description 5
- 239000012975 dibutyltin dilaurate Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- 235000013772 propylene glycol Nutrition 0.000 description 5
- 238000007789 sealing Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000001361 adipic acid Substances 0.000 description 4
- 235000011037 adipic acid Nutrition 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 230000001588 bifunctional effect Effects 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
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- 150000002009 diols Chemical class 0.000 description 4
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- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
-
- 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
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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
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation 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
- C08G2101/00—Manufacture of cellular products
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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
- C08G2190/00—Compositions for sealing or packing joints
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Sealing Material Composition (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10162144 | 2001-12-18 | ||
| PCT/EP2002/014399 WO2003051951A1 (de) | 2001-12-18 | 2002-12-17 | Verfahren zur herstellung von monomerarmen polyurethan-prepolymeren |
Publications (2)
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| JP2005511873A true JP2005511873A (ja) | 2005-04-28 |
| JP2005511873A5 JP2005511873A5 (enExample) | 2006-01-05 |
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| JP2003552827A Pending JP2005511873A (ja) | 2001-12-18 | 2002-12-17 | モノマー含有量の少ないポリウレタン−プレポリマーの製造方法 |
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| EP (1) | EP1456265A1 (enExample) |
| JP (1) | JP2005511873A (enExample) |
| KR (1) | KR20040068953A (enExample) |
| CN (1) | CN1604926A (enExample) |
| AU (1) | AU2002358740A1 (enExample) |
| BR (1) | BR0215060A (enExample) |
| CA (1) | CA2471252A1 (enExample) |
| DE (1) | DE10259248A1 (enExample) |
| HU (1) | HUP0402474A3 (enExample) |
| MX (1) | MXPA04005750A (enExample) |
| PL (1) | PL369173A1 (enExample) |
| RU (1) | RU2004122092A (enExample) |
| WO (1) | WO2003051951A1 (enExample) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009535465A (ja) * | 2006-05-02 | 2009-10-01 | バイエル・マテリアルサイエンス・アクチェンゲゼルシャフト | 湿分硬化性の接着剤およびシーラント |
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| WO2016010132A1 (ja) * | 2014-07-18 | 2016-01-21 | Dic株式会社 | 太陽電池バックシート用接着剤、太陽電池バックシート接着剤用ポリオール組成物、太陽電池バックシート、及び太陽電池モジュール |
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| DE3401129A1 (de) * | 1984-01-14 | 1985-07-18 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur herstellung gemischter polyurethan-prepolymerer |
| CA2198388A1 (en) * | 1994-08-22 | 1996-02-29 | Michael Krebs | Polyurethane compositions with a low content of monomeric diisocyanates |
| CA2214311A1 (en) * | 1996-09-06 | 1998-03-06 | Air Products And Chemicals, Inc. | Hot melt adhesives comprising low free monomer, low oligomer isocyanate prepolymers |
| DE19700014A1 (de) * | 1997-01-02 | 1998-07-09 | Henkel Kgaa | Monomerenarmes PU-Prepolymer |
| US5925781A (en) * | 1997-11-03 | 1999-07-20 | Bayer Corporation | Prepolymers with low monomeric TDI content |
| WO2001040342A1 (de) * | 1999-11-29 | 2001-06-07 | Henkel Kommanditgesellschaft Auf Aktien | Haftungsverstärker für monomerfreie reaktive polyurethane |
| DE10015891A1 (de) * | 2000-03-30 | 2001-10-11 | Degussa | Monomerarme NCO-haltige Prepolymere auf der Basis von 1,4-Diisocyanato-2,2,6-trimethylcyclohexan, ein Verfahren zu deren Herstellung, sowie Verwendung |
| DE10157488A1 (de) * | 2000-12-15 | 2002-06-20 | Henkel Kgaa | Polyurethan-Prepolymere mit NCO-Gruppen und niedrigem Gehalt an monomeren Polyisocyanat |
-
2002
- 2002-12-17 WO PCT/EP2002/014399 patent/WO2003051951A1/de not_active Ceased
- 2002-12-17 JP JP2003552827A patent/JP2005511873A/ja active Pending
- 2002-12-17 MX MXPA04005750A patent/MXPA04005750A/es unknown
- 2002-12-17 PL PL02369173A patent/PL369173A1/xx not_active Application Discontinuation
- 2002-12-17 RU RU2004122092/04A patent/RU2004122092A/ru not_active Application Discontinuation
- 2002-12-17 DE DE10259248A patent/DE10259248A1/de not_active Withdrawn
- 2002-12-17 CN CNA028252063A patent/CN1604926A/zh active Pending
- 2002-12-17 CA CA002471252A patent/CA2471252A1/en not_active Abandoned
- 2002-12-17 AU AU2002358740A patent/AU2002358740A1/en not_active Abandoned
- 2002-12-17 BR BR0215060-3A patent/BR0215060A/pt not_active IP Right Cessation
- 2002-12-17 KR KR10-2004-7009549A patent/KR20040068953A/ko not_active Withdrawn
- 2002-12-17 EP EP02793051A patent/EP1456265A1/de not_active Withdrawn
- 2002-12-17 HU HU0402474A patent/HUP0402474A3/hu unknown
-
2004
- 2004-06-18 US US10/871,343 patent/US20050020706A1/en not_active Abandoned
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009535465A (ja) * | 2006-05-02 | 2009-10-01 | バイエル・マテリアルサイエンス・アクチェンゲゼルシャフト | 湿分硬化性の接着剤およびシーラント |
| JP2013537922A (ja) * | 2010-09-07 | 2013-10-07 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 耐光性発泡ポリウレタン成形品 |
| JP2014189639A (ja) * | 2013-03-27 | 2014-10-06 | Dic Corp | ラミネート用２液混合接着剤組成物 |
| WO2015046453A1 (ja) * | 2013-09-30 | 2015-04-02 | Dic株式会社 | ポリイソシアネート混合物、ポリオール混合物、接着剤、及び積層フィルム |
| WO2016010132A1 (ja) * | 2014-07-18 | 2016-01-21 | Dic株式会社 | 太陽電池バックシート用接着剤、太陽電池バックシート接着剤用ポリオール組成物、太陽電池バックシート、及び太陽電池モジュール |
| JPWO2016010132A1 (ja) * | 2014-07-18 | 2017-04-27 | Dic株式会社 | 太陽電池バックシート用接着剤、太陽電池バックシート接着剤用ポリオール組成物、太陽電池バックシート、及び太陽電池モジュール |
| JP2016074780A (ja) * | 2014-10-03 | 2016-05-12 | Dic株式会社 | ウレタン化触媒、ポリオール混合物、接着剤、及び積層フィルム |
| KR101814295B1 (ko) | 2016-11-17 | 2018-01-03 | 황진상 | 높은 내충격성을 가진 폴리우레탄 수지 조성물 및 이를 이용한 모바일 기기용 접착 테이프 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2471252A1 (en) | 2003-06-26 |
| AU2002358740A1 (en) | 2003-06-30 |
| MXPA04005750A (es) | 2004-09-10 |
| US20050020706A1 (en) | 2005-01-27 |
| KR20040068953A (ko) | 2004-08-02 |
| PL369173A1 (en) | 2005-04-18 |
| EP1456265A1 (de) | 2004-09-15 |
| BR0215060A (pt) | 2004-11-23 |
| HUP0402474A3 (en) | 2005-10-28 |
| RU2004122092A (ru) | 2006-01-20 |
| HUP0402474A2 (hu) | 2005-03-29 |
| CN1604926A (zh) | 2005-04-06 |
| WO2003051951A1 (de) | 2003-06-26 |
| DE10259248A1 (de) | 2003-07-10 |
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