CA2172571A1 - Hydroxy-functional prepolymers containing hydantoin group precursors and their use in coating compositions - Google Patents
Hydroxy-functional prepolymers containing hydantoin group precursors and their use in coating compositionsInfo
- Publication number
- CA2172571A1 CA2172571A1 CA002172571A CA2172571A CA2172571A1 CA 2172571 A1 CA2172571 A1 CA 2172571A1 CA 002172571 A CA002172571 A CA 002172571A CA 2172571 A CA2172571 A CA 2172571A CA 2172571 A1 CA2172571 A1 CA 2172571A1
- Authority
- CA
- Canada
- Prior art keywords
- groups
- hydroxy
- functional prepolymers
- group precursors
- organic
- 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
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical group O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 title abstract 3
- 239000002243 precursor Substances 0.000 title abstract 2
- 239000008199 coating composition Substances 0.000 title 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 abstract 3
- 125000000962 organic group Chemical group 0.000 abstract 2
- 229920001228 polyisocyanate Polymers 0.000 abstract 2
- 239000005056 polyisocyanate Substances 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 150000001414 amino alcohols Chemical class 0.000 abstract 1
- 229920003180 amino resin Polymers 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 125000005442 diisocyanate group Chemical group 0.000 abstract 1
- 229920001971 elastomer Polymers 0.000 abstract 1
- 239000000806 elastomer Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 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
- C08G18/28—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
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3821—Carboxylic acids; Esters thereof with monohydroxyl compounds
-
- 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
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3823—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups
- C08G18/3829—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups containing ureum groups
Abstract
The present invention relates to hydroxy-functional prepolymers containing urea groups and corresponding to the formula see formula (I) wherein R represents the residue obtained by removing the isocyanate groups from an organic monomeric diisocyanate, a polyisocyanate adduct or an NCO prepolymer containing hydantoin groups or hydantoin group precursors, R1 and R2 may be identical or different and represent organic groups which are inert towards isocyanate groups at a temperature of 100°C or less, R3 and R4 may be identical or different and represent hydrogen or organic groups which are inert towards isocyanate groups at a temperature of 100°C or less, R5 represents the hydrocarbon radical obtained by removing the amino and hydroxyl groups from an amino alcohol, n has a value of 1 to 3 and m has a value of 2 to 6.
The present invention is also directed to compositions suitable for the production of coatings, adhesives or elastomers containing these polyhydantoin prepolymers in combination with optionally blocked polyisocyanates or aminoplast resins.
The present invention is also directed to compositions suitable for the production of coatings, adhesives or elastomers containing these polyhydantoin prepolymers in combination with optionally blocked polyisocyanates or aminoplast resins.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/443,502 | 1995-05-18 | ||
| US08/443,502 US5596044A (en) | 1995-05-18 | 1995-05-18 | Hydroxy-functional prepolymers containing hydantoin group precursors and their use in coating compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2172571A1 true CA2172571A1 (en) | 1996-11-19 |
| CA2172571C CA2172571C (en) | 2007-10-30 |
Family
ID=23761042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002172571A Expired - Fee Related CA2172571C (en) | 1995-05-18 | 1996-03-25 | Hydroxy-functional prepolymers containing hydantoin group precursors and their use in coating compositions |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5596044A (en) |
| EP (1) | EP0744419B1 (en) |
| JP (1) | JP3978247B2 (en) |
| AT (1) | ATE186927T1 (en) |
| CA (1) | CA2172571C (en) |
| DE (1) | DE69605242T2 (en) |
| ES (1) | ES2139979T3 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2172579A1 (en) * | 1995-05-18 | 1996-11-19 | E. Haakan Jonsson | Hydroxy-functional polyhydantoin prepolymers and their use in coating compositions |
| US5736604A (en) * | 1996-12-17 | 1998-04-07 | Bayer Corporation | Aqueous, two-component polyurea coating compositions |
| US6162938A (en) * | 1998-11-19 | 2000-12-19 | 3M Innovative Properties Company | Secondary amine-functional silanes, silane-functional polymers therefrom, and resulting cured polymers |
| US6355829B2 (en) * | 1999-09-02 | 2002-03-12 | Bayer Corporation | Aspartate-terminated urea/urethane prepolymers and their use in coating compositions |
| US6472493B1 (en) | 1999-11-23 | 2002-10-29 | E. I. Du Pont De Nemours And Company | Clear coating composition having improved early hardness and water resistance |
| EP1717254A1 (en) * | 2005-04-29 | 2006-11-02 | Sika Technology AG | Moisture-curable composition with improved elongation |
| EP3941958B1 (en) * | 2019-03-19 | 2023-06-07 | Covestro Intellectual Property GmbH & Co. KG | Secondary amino group containing binders based on cyclic ethers |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670813A1 (en) * | 1967-03-01 | 1971-03-11 | Bayer Ag | Polycarboxylic acid esters |
| US3549599A (en) * | 1967-03-01 | 1970-12-22 | Bayer Ag | Carboxylic acid ester substituted polyhydantions |
| DE2158945A1 (en) * | 1971-11-27 | 1973-05-30 | Horst Holfort | Nitrogen-contg coating resins - prepd from (n-carboxy) betaamino carboxylic acids (and derivs) and di/polyisocyanates or di/ |
| FR2656953B1 (en) * | 1990-01-05 | 1996-08-30 | Merlin Gerin | ELECTROMAGNETIC RELAY POLARIZED BY A PERMANENT MAGNET. |
| US5243012A (en) * | 1992-06-10 | 1993-09-07 | Miles Inc. | Polyurea coating compositions having improved pot lives |
-
1995
- 1995-05-18 US US08/443,502 patent/US5596044A/en not_active Expired - Lifetime
-
1996
- 1996-03-25 CA CA002172571A patent/CA2172571C/en not_active Expired - Fee Related
- 1996-05-06 AT AT96107062T patent/ATE186927T1/en not_active IP Right Cessation
- 1996-05-06 DE DE69605242T patent/DE69605242T2/en not_active Expired - Fee Related
- 1996-05-06 ES ES96107062T patent/ES2139979T3/en not_active Expired - Lifetime
- 1996-05-06 EP EP96107062A patent/EP0744419B1/en not_active Expired - Lifetime
- 1996-05-16 JP JP14485396A patent/JP3978247B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH08311009A (en) | 1996-11-26 |
| US5596044A (en) | 1997-01-21 |
| JP3978247B2 (en) | 2007-09-19 |
| DE69605242T2 (en) | 2000-04-13 |
| ES2139979T3 (en) | 2000-02-16 |
| ATE186927T1 (en) | 1999-12-15 |
| CA2172571C (en) | 2007-10-30 |
| EP0744419A1 (en) | 1996-11-27 |
| DE69605242D1 (en) | 1999-12-30 |
| EP0744419B1 (en) | 1999-11-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |