JP2013512322A5 - - Google Patents
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- Publication number
- JP2013512322A5 JP2013512322A5 JP2012541461A JP2012541461A JP2013512322A5 JP 2013512322 A5 JP2013512322 A5 JP 2013512322A5 JP 2012541461 A JP2012541461 A JP 2012541461A JP 2012541461 A JP2012541461 A JP 2012541461A JP 2013512322 A5 JP2013512322 A5 JP 2013512322A5
- Authority
- JP
- Japan
- Prior art keywords
- resin system
- pultrusion
- acid
- polybasic acid
- isocyanate
- 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
- 150000007519 polyprotic acids Polymers 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000012948 isocyanate Substances 0.000 claims description 8
- 150000002513 isocyanates Chemical class 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims 12
- 229920005989 resin Polymers 0.000 claims 12
- 239000002657 fibrous material Substances 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 238000009835 boiling Methods 0.000 claims 2
- 229920001228 polyisocyanate Polymers 0.000 claims 2
- 239000005056 polyisocyanate Substances 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- -1 and isomers thereof Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical class OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 1
- BRHDHVCWMWMETM-UHFFFAOYSA-N hexane-1,6-diamine;propane-1,3-diamine Chemical compound NCCCN.NCCCCCCN BRHDHVCWMWMETM-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 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
- 150000007522 mineralic acids Chemical class 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09177603 | 2009-12-01 | ||
| EP09177603.9 | 2009-12-01 | ||
| PCT/EP2010/068518 WO2011067246A1 (de) | 2009-12-01 | 2010-11-30 | Pultrusionsharzsystem auf basis von polyurethan |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013512322A JP2013512322A (ja) | 2013-04-11 |
| JP2013512322A5 true JP2013512322A5 (enExample) | 2014-08-28 |
| JP5684827B2 JP5684827B2 (ja) | 2015-03-18 |
Family
ID=43530955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012541461A Expired - Fee Related JP5684827B2 (ja) | 2009-12-01 | 2010-11-30 | ポリウレタン−ベースのプルトルージョン樹脂系 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8663414B2 (enExample) |
| EP (1) | EP2507041B1 (enExample) |
| JP (1) | JP5684827B2 (enExample) |
| KR (1) | KR101830203B1 (enExample) |
| CN (1) | CN102639314B (enExample) |
| CA (1) | CA2782010A1 (enExample) |
| DK (1) | DK2507041T3 (enExample) |
| ES (1) | ES2453268T3 (enExample) |
| MX (1) | MX2012006281A (enExample) |
| WO (1) | WO2011067246A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015510011A (ja) * | 2012-02-28 | 2015-04-02 | ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェンＨｅｎｋｅｌ ＡＧ ＆ Ｃｏ．ＫＧａＡ | 高いガラス転移温度を有する２ｋポリウレタン系 |
| WO2013127850A1 (en) | 2012-02-29 | 2013-09-06 | Bayer Intellectual Property Gmbh | 2-k pultrusion formulation and process |
| DE102014208353A1 (de) | 2014-05-05 | 2015-11-05 | Henkel Ag & Co. Kgaa | Mehrphasige Polyurethan-Zusammensetzung mit reduzierter Schaumentwicklung |
| CN105778038B (zh) | 2014-12-24 | 2021-02-23 | 科思创德国股份有限公司 | 聚氨酯拉挤成型制品 |
| US9757905B2 (en) * | 2015-05-11 | 2017-09-12 | Covestro Llc | Filament winding processes using polyurethane resins and systems for making composites |
| CN106700015B (zh) * | 2015-11-18 | 2020-04-10 | 万华化学集团股份有限公司 | 一种聚氨酯树脂体系及其用于制备拉挤成型纤维复合材料的方法 |
| EP3445571B1 (de) | 2016-04-21 | 2020-02-26 | Basf Se | Verfahren zur herstellung von pultrudaten auf basis von polyurethan |
| US20180169974A1 (en) * | 2016-12-16 | 2018-06-21 | Siemens Energy, Inc. | Method and system for making slot cells by pultrusion |
| EP3392284A1 (de) | 2017-04-18 | 2018-10-24 | Covestro Deutschland AG | Pultrudat, dessen herstellung und verwendung |
| CN111183166B (zh) | 2017-09-29 | 2022-07-26 | 巴斯夫欧洲公司 | 聚氨酯复合材料 |
| WO2019105914A1 (en) | 2017-12-01 | 2019-06-06 | Basf Se | Polyurethane composition having improved processing time |
| KR102030394B1 (ko) * | 2017-12-22 | 2019-10-11 | 하대환 | 인발성형용 속경화성 이액형 폴리우레탄 수지 조성물 |
| DK4182370T3 (da) | 2020-07-15 | 2025-07-21 | Covestro Deutschland Ag | Polyurethan-reaktivt system til pultrusion |
| CN113637130B (zh) * | 2021-08-18 | 2024-04-30 | 四川东树新材料有限公司 | 风电叶片拉挤板用改性聚氨酯 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS501147B1 (enExample) * | 1970-12-28 | 1975-01-16 | ||
| JPS54143306A (en) * | 1978-04-27 | 1979-11-08 | Arakawa Rinsan Kagaku Kogyo | Binder for aqueous printing ink |
| JPS5560554A (en) * | 1978-10-31 | 1980-05-07 | Sanyo Chem Ind Ltd | Stable polyurethane solution |
| US4260538A (en) * | 1979-09-27 | 1981-04-07 | The Budd Company | Matured moldable thermosetting dual polyester resin system |
| US4711912A (en) | 1982-04-29 | 1987-12-08 | The Celotex Corporation | Polyisocyanurate foams from digestion products of polyalkylene terephthalate polymers and polyols |
| DE3247756A1 (de) * | 1982-12-23 | 1984-06-28 | Herberts Gmbh, 5600 Wuppertal | Waessriges ueberzugsmittel |
| US4868224A (en) * | 1988-10-21 | 1989-09-19 | Mobay Corporation | Process for the production of molded products using internal mold release agents |
| US4954537A (en) * | 1989-06-08 | 1990-09-04 | Mobay Corporation | Internal mold release agent for use in polyurea rim systems |
| DE19644017A1 (de) * | 1996-10-31 | 1998-05-07 | Basf Ag | Naturfaser-verstärkte Polyisocyanat-Polyaddidionsprodukte, Verfahren zu deren Herstellung und deren Verwendung |
| HK1042313A1 (zh) * | 1998-11-16 | 2002-08-09 | 亨茨曼国际有限公司 | 聚异氰脲酸酯组合物及复合材料 |
| PL212979B1 (pl) * | 2000-02-10 | 2012-12-31 | Dow Global Technologies Inc | Sposób wytwarzania elastycznej pianki poliuretanowej, autokatalityczna kompozycja poliolowa i prepolimer |
| CY2010012I2 (el) | 2000-05-25 | 2020-05-29 | Novartis Ag | Μιμητικα θρομβοποιητινης |
| JP2003122001A (ja) * | 2001-10-15 | 2003-04-25 | Nippon Kayaku Co Ltd | 感光性樹脂、及びそれを用いた感光性樹脂組成物、並びにその硬化物 |
| JP2005015834A (ja) * | 2003-06-25 | 2005-01-20 | Nippon Steel Corp | 耐食性に優れ溶接可能な高耐食性塗装鋼板 |
| JP4153859B2 (ja) | 2003-10-15 | 2008-09-24 | 株式会社島精機製作所 | 刺繍データ作成装置と刺繍データの作成方法及び刺繍データの作成プログラム |
| EP1687128A2 (en) | 2003-11-17 | 2006-08-09 | Huntsman International Llc | Pultrusion systems and process |
| JP4438944B2 (ja) * | 2004-07-12 | 2010-03-24 | 日東紡績株式会社 | ジグザグ形状の繊維強化樹脂成形品の製造法 |
| US20060173128A1 (en) * | 2004-11-15 | 2006-08-03 | Huntsman International Llc | Pultrusion systems and process |
| US7875675B2 (en) | 2005-11-23 | 2011-01-25 | Milgard Manufacturing Incorporated | Resin for composite structures |
| US8597016B2 (en) | 2005-11-23 | 2013-12-03 | Milgard Manufacturing Incorporated | System for producing pultruded components |
| US7901762B2 (en) | 2005-11-23 | 2011-03-08 | Milgard Manufacturing Incorporated | Pultruded component |
| JP4850551B2 (ja) * | 2006-03-22 | 2012-01-11 | 京セラケミカル株式会社 | 搬送用シャフト |
| US20080090921A1 (en) | 2006-10-12 | 2008-04-17 | Hayes John E | DMC-catalyzed polyol containing polyurethane pultrusion formulations and processes |
| US20080087373A1 (en) | 2006-10-12 | 2008-04-17 | Hayes John E | Polymer polyol-containing polyurethane pultrusion formulations and processes |
| US20080090966A1 (en) | 2006-10-12 | 2008-04-17 | Hayes John E | Immiscible polyurethane pultrusion formulations and processes |
-
2010
- 2010-11-30 KR KR1020127016655A patent/KR101830203B1/ko not_active Expired - Fee Related
- 2010-11-30 EP EP10784534.9A patent/EP2507041B1/de active Active
- 2010-11-30 DK DK10784534.9T patent/DK2507041T3/da active
- 2010-11-30 US US13/513,471 patent/US8663414B2/en active Active
- 2010-11-30 CA CA2782010A patent/CA2782010A1/en not_active Abandoned
- 2010-11-30 JP JP2012541461A patent/JP5684827B2/ja not_active Expired - Fee Related
- 2010-11-30 WO PCT/EP2010/068518 patent/WO2011067246A1/de not_active Ceased
- 2010-11-30 MX MX2012006281A patent/MX2012006281A/es active IP Right Grant
- 2010-11-30 ES ES10784534.9T patent/ES2453268T3/es active Active
- 2010-11-30 CN CN201080054523.4A patent/CN102639314B/zh active Active
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