CN117881713A - 双组分聚氨酯粘合剂组合物 - Google Patents
双组分聚氨酯粘合剂组合物 Download PDFInfo
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- CN117881713A CN117881713A CN202280056832.8A CN202280056832A CN117881713A CN 117881713 A CN117881713 A CN 117881713A CN 202280056832 A CN202280056832 A CN 202280056832A CN 117881713 A CN117881713 A CN 117881713A
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- component
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- polyamine
- polyol
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- 229920000768 polyamine Polymers 0.000 claims description 79
- 150000003077 polyols Chemical class 0.000 claims description 78
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 claims description 63
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- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 34
- 150000001412 amines Chemical class 0.000 claims description 34
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- 229920000570 polyether Polymers 0.000 claims description 31
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 25
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 25
- 150000002009 diols Chemical class 0.000 claims description 22
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 20
- 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 claims description 18
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- 125000005442 diisocyanate group Chemical group 0.000 claims description 14
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- 150000004072 triols Chemical class 0.000 claims description 9
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 claims description 8
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- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical group CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 8
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 claims description 6
- QSRJVOOOWGXUDY-UHFFFAOYSA-N 2-[2-[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]ethoxy]ethoxy]ethyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC(=O)OCCOCCOCCOC(=O)CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 QSRJVOOOWGXUDY-UHFFFAOYSA-N 0.000 claims description 6
- VFBJXXJYHWLXRM-UHFFFAOYSA-N 2-[2-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]ethylsulfanyl]ethyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCSCCOC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 VFBJXXJYHWLXRM-UHFFFAOYSA-N 0.000 claims description 6
- ZVVFVKJZNVSANF-UHFFFAOYSA-N 6-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]hexyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCCCCCOC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 ZVVFVKJZNVSANF-UHFFFAOYSA-N 0.000 claims description 6
- OKOBUGCCXMIKDM-UHFFFAOYSA-N Irganox 1098 Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)NCCCCCCNC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 OKOBUGCCXMIKDM-UHFFFAOYSA-N 0.000 claims description 6
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
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- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 claims description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 5
- PAUHLEIGHAUFAK-UHFFFAOYSA-N 1-isocyanato-1-[(1-isocyanatocyclohexyl)methyl]cyclohexane Chemical compound C1CCCCC1(N=C=O)CC1(N=C=O)CCCCC1 PAUHLEIGHAUFAK-UHFFFAOYSA-N 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims description 4
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 claims description 3
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 claims description 3
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- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
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- 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 claims description 3
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- 238000012360 testing method Methods 0.000 description 12
- JLZIIHMTTRXXIN-UHFFFAOYSA-N 2-(2-hydroxy-4-methoxybenzoyl)benzoic acid Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O JLZIIHMTTRXXIN-UHFFFAOYSA-N 0.000 description 11
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Classifications
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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
- 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
- C09J175/12—Polyurethanes from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202163238428P | 2021-08-30 | 2021-08-30 | |
| US63/238428 | 2021-08-30 | ||
| PCT/US2022/032098 WO2023033892A1 (en) | 2021-08-30 | 2022-06-03 | Two-component polyurethane adhesive composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117881713A true CN117881713A (zh) | 2024-04-12 |
Family
ID=82482837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202280056832.8A Pending CN117881713A (zh) | 2021-08-30 | 2022-06-03 | 双组分聚氨酯粘合剂组合物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20240271023A1 (https=) |
| EP (1) | EP4396251A1 (https=) |
| JP (1) | JP2024532236A (https=) |
| KR (1) | KR20240051134A (https=) |
| CN (1) | CN117881713A (https=) |
| WO (1) | WO2023033892A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2025104495A1 (en) * | 2023-11-14 | 2025-05-22 | Arkema France | 2k-low modulus polyurethane adhesive for bonding composites |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4743672A (en) * | 1987-02-26 | 1988-05-10 | Ashland Oil, Inc. | Sag resistant, two component urethane adhesives |
| US5922809A (en) | 1996-01-11 | 1999-07-13 | The Dow Chemical Company | One-part moisture curable polyurethane adhesive |
| AU2983200A (en) | 1999-02-05 | 2000-08-25 | Dow Chemical Company, The | Polyurethane sealant compositions |
| DE10226926A1 (de) * | 2002-06-17 | 2004-02-05 | Bayer Ag | Blockierte Polyisocyanate |
| DE102004043342A1 (de) * | 2004-09-08 | 2006-03-09 | Bayer Materialscience Ag | Blockierte Polyurethan-Prepolymere als Klebstoffe |
| RU2009115962A (ru) * | 2006-09-29 | 2010-11-10 | Циба Холдинг Инк. (Ch) | Фотолатентные основания для систем, основанных на блокированных изоцианатах |
| DE102007012908A1 (de) * | 2007-03-19 | 2008-09-25 | Momentive Performance Materials Gmbh | Neue Polyamid-Polysiloxan-Verbindungen |
| JP2012152725A (ja) * | 2011-01-28 | 2012-08-16 | Tosoh Corp | ブロックイソシアネート解離触媒及びその用途 |
| JP6814781B2 (ja) * | 2017-12-12 | 2021-01-20 | 三洋化成工業株式会社 | ２液硬化型ウレタン粘着剤用主剤及び２液硬化型ウレタン粘着剤 |
| JP6896052B2 (ja) * | 2019-12-10 | 2021-06-30 | 大日精化工業株式会社 | ブロックイソシアネート解離触媒、熱硬化性組成物、接着剤、塗工剤、物品 |
-
2022
- 2022-06-03 KR KR1020247005955A patent/KR20240051134A/ko active Pending
- 2022-06-03 CN CN202280056832.8A patent/CN117881713A/zh active Pending
- 2022-06-03 US US18/569,339 patent/US20240271023A1/en active Pending
- 2022-06-03 JP JP2024510660A patent/JP2024532236A/ja active Pending
- 2022-06-03 EP EP22740601.4A patent/EP4396251A1/en active Pending
- 2022-06-03 WO PCT/US2022/032098 patent/WO2023033892A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| JP2024532236A (ja) | 2024-09-05 |
| EP4396251A1 (en) | 2024-07-10 |
| KR20240051134A (ko) | 2024-04-19 |
| WO2023033892A1 (en) | 2023-03-09 |
| US20240271023A1 (en) | 2024-08-15 |
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