CA2174085A1 - Reactive diluent aldimine oxazolidines - Google Patents
Reactive diluent aldimine oxazolidinesInfo
- Publication number
- CA2174085A1 CA2174085A1 CA002174085A CA2174085A CA2174085A1 CA 2174085 A1 CA2174085 A1 CA 2174085A1 CA 002174085 A CA002174085 A CA 002174085A CA 2174085 A CA2174085 A CA 2174085A CA 2174085 A1 CA2174085 A1 CA 2174085A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- hydrogen atoms
- groups
- composition
- compound
- 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.)
- Abandoned
Links
- -1 aldimine oxazolidines Chemical class 0.000 title claims abstract description 25
- 239000003085 diluting agent Substances 0.000 title description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 33
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 19
- 150000003573 thiols Chemical group 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 17
- 150000002367 halogens Chemical group 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- 125000000524 functional group Chemical group 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 14
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 14
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 12
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 11
- 125000000732 arylene group Chemical group 0.000 claims abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 125000002993 cycloalkylene group Chemical group 0.000 claims abstract description 8
- 239000011248 coating agent Substances 0.000 claims description 28
- 238000000576 coating method Methods 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 17
- 150000004705 aldimines Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
- 239000000853 adhesive Substances 0.000 claims description 6
- 230000001070 adhesive effect Effects 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- 239000003822 epoxy resin Substances 0.000 claims description 4
- 229920000647 polyepoxide Polymers 0.000 claims description 4
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 3
- 239000000976 ink Substances 0.000 claims description 3
- 239000000565 sealant Substances 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- 241001024304 Mino Species 0.000 description 2
- 241000282320 Panthera leo Species 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 229920000582 polyisocyanurate Polymers 0.000 description 2
- 239000011495 polyisocyanurate Substances 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 241001136792 Alle Species 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- YFONKFDEZLYQDH-OPQQBVKSSA-N N-[(1R,2S)-2,6-dimethyindan-1-yl]-6-[(1R)-1-fluoroethyl]-1,3,5-triazine-2,4-diamine Chemical compound C[C@@H](F)C1=NC(N)=NC(N[C@H]2C3=CC(C)=CC=C3C[C@@H]2C)=N1 YFONKFDEZLYQDH-OPQQBVKSSA-N 0.000 description 1
- 101150050192 PIGM gene Proteins 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 235000014328 Schoenoplectus acutus var occidentalis Nutrition 0.000 description 1
- 244000136421 Scirpus acutus Species 0.000 description 1
- 235000014326 Scirpus californicus Nutrition 0.000 description 1
- 235000017913 Scirpus lacustris Nutrition 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000007982 azolidines Chemical class 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004710 electron pair approximation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
Classifications
-
- 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
- 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
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3271—Hydroxyamines
- C08G18/3296—Hydroxyamines being in latent form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/143,470 | 1993-10-26 | ||
| US08/143,470 US5466769A (en) | 1993-10-26 | 1993-10-26 | Reactive diluent aldimine oxazolidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2174085A1 true CA2174085A1 (en) | 1995-05-04 |
Family
ID=22504227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002174085A Abandoned CA2174085A1 (en) | 1993-10-26 | 1994-10-21 | Reactive diluent aldimine oxazolidines |
Country Status (8)
| Country | Link |
|---|---|
| US (4) | US5466769A (en:Method) |
| EP (1) | EP0748344A1 (en:Method) |
| JP (1) | JPH09504328A (en:Method) |
| KR (1) | KR960705864A (en:Method) |
| AU (1) | AU8051194A (en:Method) |
| CA (1) | CA2174085A1 (en:Method) |
| TW (1) | TW287161B (en:Method) |
| WO (1) | WO1995011933A1 (en:Method) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5466769A (en) * | 1993-10-26 | 1995-11-14 | Angus Chemical Company | Reactive diluent aldimine oxazolidines |
| US5977285A (en) * | 1997-08-07 | 1999-11-02 | Akzo Nobel N.V. | Sprayable coating compositions comprising oxazolidines, isocyanates and hydroxyl or amine functional resins |
| US6545117B1 (en) | 1997-08-07 | 2003-04-08 | Akzo Noble N.V. | Sprayable coating compositions comprising an oxazolidine functional compound, an isocyanate functional compound, and a compound selected from a mercapto and a sulfonic acid functional compound |
| US5955199A (en) * | 1997-09-26 | 1999-09-21 | Ashland Inc. | Imine-containing curative for two component polyurethane structural adhesives |
| US6001274A (en) * | 1999-01-04 | 1999-12-14 | Gabriel J. Farkas | Composition to detoxify and to convert formaldehyde in gaseous state and in aqueous and non-aqueous solutions |
| CA2284342C (en) | 1999-09-29 | 2011-11-01 | Meaney, Daniel J., Jr. | Method, solution and paint for forming a metallic mirror surface or metallic luster |
| US7111950B2 (en) * | 1999-09-29 | 2006-09-26 | American Spray Coatings | Method for forming a metallic mirror surface on a receiving surface |
| WO2001023103A1 (en) * | 1999-09-29 | 2001-04-05 | American Spray Coatings | Method, solution and paint for forming a metallic mirror surface or metallic luster |
| US6362302B1 (en) | 1999-11-29 | 2002-03-26 | Carl E. Boddie | Method and compositions for spray molding polyurethane three dimensional objects |
| KR100366564B1 (ko) * | 2000-05-23 | 2003-01-09 | 삼화페인트공업주식회사 | 잠재성 경화재의 제조방법 및 그 경화제를 포함하는폴리우레탄 일액형도료 조성물 |
| ES2314717T3 (es) * | 2004-09-17 | 2009-03-16 | Akzo Nobel Coatings International Bv | Composicion de revestimiento basada en curadi de tiol-nco. |
| KR100777429B1 (ko) * | 2005-08-04 | 2007-11-28 | 에스케이씨 주식회사 | 저장성이 우수한 습기경화형 폴리우레탄 조성물 및 그제조방법 |
| EP1772447A1 (de) * | 2005-09-30 | 2007-04-11 | Sika Technology AG | Aldimine mit aktivem Wasserstoff aufweisenden Reaktivgruppen sowie deren Verwendung |
| US20090227758A1 (en) * | 2008-03-07 | 2009-09-10 | Yoshiaki Miyazaki | Polyurethanes having low levels of aldehyde emissions |
| EP2358462A1 (en) * | 2008-11-17 | 2011-08-24 | Dow Global Technologies LLC | Methods for reducing airborne formaldehyde |
| EP2327733A1 (en) * | 2009-10-30 | 2011-06-01 | Sika Technology AG | Non-Crystallising Bis-Oxazolidines |
| EP2948490B1 (en) | 2013-01-22 | 2020-01-15 | Sika Technology AG | Liquid-applied waterproofing membrane for roofs comprising two different aldimines |
| EP2948485B1 (en) | 2013-01-22 | 2019-09-11 | Sika Technology AG | Liquid-applied waterproofing membrane comprising oxazolidine and aldimine |
| EP2948492B1 (en) * | 2013-01-22 | 2020-03-18 | Sika Technology AG | Liquid-applied waterproofing membrane for roofs comprising a trialdimine |
| CN104903377B (zh) | 2013-01-22 | 2019-07-05 | Sika技术股份公司 | 包含长链醛亚胺的屋顶用液体施加的防水膜 |
| EP3039047B1 (en) | 2013-08-26 | 2021-10-13 | Huntsman Petrochemical LLC | Reduction of aldehyde content in amine catalysts |
| US10131737B2 (en) | 2013-10-01 | 2018-11-20 | Huntsman Petrochemical Llc | Reduction of aldehydes in amine catalysts |
| JP6778196B2 (ja) | 2014-12-31 | 2020-10-28 | ハンツマン ペトロケミカル エルエルシーＨｕｎｔｓｍａｎ Ｐｅｔｒｏｃｈｅｍｉｃａｌ ＬＬＣ | アミン触媒中のアルデヒドの削減 |
| IL243898B (en) * | 2015-02-03 | 2020-04-30 | Seagrave Coatings Corp | Coating compositions |
| BR112019016446A2 (pt) | 2017-02-09 | 2020-04-07 | Dow Global Technologies Llc | espuma de poliuretano com baixos níveis de emissões de aldeído |
| CN110446732A (zh) | 2017-02-20 | 2019-11-12 | 陶氏环球技术有限责任公司 | 具有降低的醛排放的聚氨酯 |
| CN107043447B (zh) * | 2017-04-19 | 2019-12-03 | 江苏湘园化工有限公司 | 一种非对称潜伏性聚氨酯固化剂及其制备方法 |
| KR102649156B1 (ko) | 2018-08-02 | 2024-03-20 | 다우 글로벌 테크놀로지스 엘엘씨 | 폴리우레탄 폼에서 알데히드 방출을 감소시키는 방법 |
| JP7247320B2 (ja) | 2018-08-02 | 2023-03-28 | ダウ グローバル テクノロジーズ エルエルシー | ポリウレタン発泡体のアルデヒド排出量を減少させるための方法 |
| WO2020024231A1 (en) | 2018-08-02 | 2020-02-06 | Dow Global Technologies Llc | Methods for reducing aldehyde emissions in polyurethane foams |
| EP3830166A4 (en) | 2018-08-02 | 2022-03-23 | Dow Global Technologies LLC | PROCESS FOR REDUCING ALDEHYDE EMISSIONS IN POLYURETHANE FOAM MATERIALS |
| CN112638974B (zh) | 2018-08-02 | 2023-08-01 | 陶氏环球技术有限责任公司 | 减少聚氨酯泡沫中醛排放的方法 |
| CN114341224B (zh) | 2019-08-30 | 2024-07-30 | 陶氏环球技术有限责任公司 | 减少聚酯多元醇和聚氨酯泡沫中醛排放的方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3743626A (en) * | 1968-10-18 | 1973-07-03 | Rohm & Haas | Hydrocurable oxazolidine-isocyanate compositions |
| US4054717A (en) * | 1975-11-19 | 1977-10-18 | Rohm And Haas Company | Mineral paper coating compositions containing latex and amphoteric polymer |
| US4046744A (en) * | 1976-07-28 | 1977-09-06 | Rohm And Haas Company | Thermosetting coatings based on ketoxime-blocked isocyanates and oxazolidines |
| JPS6029730B2 (ja) * | 1977-08-06 | 1985-07-12 | 三菱電機株式会社 | エポキシ樹脂組成物 |
| DE3019356A1 (de) * | 1980-05-21 | 1981-11-26 | Sika AG, vorm. Kaspar Winkler & Co., 8048 Zürich | Neue, adimin- und oxazolidingruppen aufweisende verbindungen sowie verfahren zu deren herstellung und ihre verwendung als haerter fuer polyisocyanate |
| US4772716A (en) * | 1986-07-14 | 1988-09-20 | Ciba-Geigy Corporation | Oxazolidines containing silane groups |
| US5104955A (en) * | 1987-04-27 | 1992-04-14 | The Sherwin-Williams Company | Hydroxy-functional polyester diluents as additives in coating compositions |
| US5223174A (en) * | 1991-08-15 | 1993-06-29 | Angus Chemical Company | Moisture-scavenging iminoalcohol-oxazolidine mixtures |
| US5214086A (en) * | 1991-09-04 | 1993-05-25 | Basf Corporation | Coating compositions which may be ambient cured |
| US5466769A (en) * | 1993-10-26 | 1995-11-14 | Angus Chemical Company | Reactive diluent aldimine oxazolidines |
-
1993
- 1993-10-26 US US08/143,470 patent/US5466769A/en not_active Expired - Fee Related
-
1994
- 1994-10-11 US US08/321,436 patent/US5506329A/en not_active Expired - Fee Related
- 1994-10-11 US US08/321,227 patent/US5591819A/en not_active Expired - Fee Related
- 1994-10-21 CA CA002174085A patent/CA2174085A1/en not_active Abandoned
- 1994-10-21 JP JP7512721A patent/JPH09504328A/ja active Pending
- 1994-10-21 WO PCT/US1994/012041 patent/WO1995011933A1/en not_active Application Discontinuation
- 1994-10-21 AU AU80511/94A patent/AU8051194A/en not_active Abandoned
- 1994-10-21 KR KR1019960702093A patent/KR960705864A/ko not_active Withdrawn
- 1994-10-21 EP EP94931423A patent/EP0748344A1/en not_active Withdrawn
- 1994-10-27 TW TW083109916A patent/TW287161B/zh active
-
1995
- 1995-11-13 US US08/556,025 patent/US5571922A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU8051194A (en) | 1995-05-22 |
| WO1995011933A1 (en) | 1995-05-04 |
| US5466769A (en) | 1995-11-14 |
| TW287161B (en:Method) | 1996-10-01 |
| US5506329A (en) | 1996-04-09 |
| US5571922A (en) | 1996-11-05 |
| US5591819A (en) | 1997-01-07 |
| JPH09504328A (ja) | 1997-04-28 |
| KR960705864A (ko) | 1996-11-08 |
| EP0748344A1 (en) | 1996-12-18 |
| EP0748344A4 (en) | 1996-09-19 |
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