DE10030684A1 - Polymere Aldehyd/Polyetheramin-Netzwerke - Google Patents
Polymere Aldehyd/Polyetheramin-NetzwerkeInfo
- Publication number
- DE10030684A1 DE10030684A1 DE2000130684 DE10030684A DE10030684A1 DE 10030684 A1 DE10030684 A1 DE 10030684A1 DE 2000130684 DE2000130684 DE 2000130684 DE 10030684 A DE10030684 A DE 10030684A DE 10030684 A1 DE10030684 A1 DE 10030684A1
- Authority
- DE
- Germany
- Prior art keywords
- optionally
- valent organic
- formaldehyde
- formula
- networks according
- 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.)
- Withdrawn
Links
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 56
- 150000001412 amines Chemical class 0.000 claims abstract description 23
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- 229920005862 polyol Polymers 0.000 claims abstract description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 12
- 150000003077 polyols Chemical class 0.000 claims abstract description 10
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 238000005576 amination reaction Methods 0.000 claims abstract description 8
- 239000002243 precursor Substances 0.000 claims abstract description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 147
- 229920000642 polymer Polymers 0.000 claims description 15
- -1 aliphatic polyols Chemical class 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000005549 heteroarylene group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 58
- 239000007795 chemical reaction product Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 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 4
- 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 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 229960002920 sorbitol Drugs 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- OYWRDHBGMCXGFY-UHFFFAOYSA-N 1,2,3-triazinane Chemical group C1CNNNC1 OYWRDHBGMCXGFY-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- LKLLNYWECKEQIB-UHFFFAOYSA-N 1,3,5-triazinane Chemical class C1NCNCN1 LKLLNYWECKEQIB-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- UNXHWFMMPAWVPI-QWWZWVQMSA-N D-threitol Chemical compound OC[C@@H](O)[C@H](O)CO UNXHWFMMPAWVPI-QWWZWVQMSA-N 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229920005628 alkoxylated polyol Polymers 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012430 organic reaction media Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/04—1,2,3-Triazines
-
- 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
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08G12/06—Amines
-
- 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
- C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
- C08G16/02—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes
- C08G16/0212—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds
- C08G16/0218—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds containing atoms other than carbon and hydrogen
- C08G16/0225—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds containing atoms other than carbon and hydrogen containing oxygen
-
- 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
- C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
- C08G16/02—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes
- C08G16/0212—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds
- C08G16/0218—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds containing atoms other than carbon and hydrogen
- C08G16/0231—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds containing atoms other than carbon and hydrogen containing nitrogen
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
- C08G73/0644—Poly(1,3,5)triazines
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
- C08G73/065—Preparatory processes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Emergency Medicine (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2000130684 DE10030684A1 (de) | 2000-06-23 | 2000-06-23 | Polymere Aldehyd/Polyetheramin-Netzwerke |
| AU2001283881A AU2001283881A1 (en) | 2000-06-23 | 2001-06-22 | Polymeric aldehyde/polyetheramine networks |
| PCT/EP2001/007134 WO2001098388A1 (fr) | 2000-06-23 | 2001-06-22 | Reseaux polymeres aldehyde / polyetheramine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2000130684 DE10030684A1 (de) | 2000-06-23 | 2000-06-23 | Polymere Aldehyd/Polyetheramin-Netzwerke |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10030684A1 true DE10030684A1 (de) | 2002-01-03 |
Family
ID=7646588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2000130684 Withdrawn DE10030684A1 (de) | 2000-06-23 | 2000-06-23 | Polymere Aldehyd/Polyetheramin-Netzwerke |
Country Status (3)
| Country | Link |
|---|---|
| AU (1) | AU2001283881A1 (fr) |
| DE (1) | DE10030684A1 (fr) |
| WO (1) | WO2001098388A1 (fr) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060135391A1 (en) | 2004-12-17 | 2006-06-22 | Scheibel Jeffrey J | Modified alkoxylated polyol compounds |
| CN1894306A (zh) * | 2003-12-19 | 2007-01-10 | 宝洁公司 | 改性的烷氧基化多元醇化合物 |
| CA2554379A1 (fr) | 2004-02-04 | 2005-08-25 | The Procter & Gamble Company | Polyol alcoxyle contenant des groupes fonctionnels de terminaison activateurs de blanchiment |
| CN101084298A (zh) | 2004-12-17 | 2007-12-05 | 宝洁公司 | 用于改善疏水性污垢清洁效果的亲水改性的多羟基化合物 |
| EP1838824A1 (fr) | 2004-12-17 | 2007-10-03 | The Procter and Gamble Company | Polyols modifies de maniere hydrophobe pour un meilleur nettoyage des salissures hydrophobes |
| US9243107B2 (en) | 2013-10-10 | 2016-01-26 | International Business Machines Corporation | Methods of preparing polyhemiaminals and polyhexahydrotriazines |
| US9120897B1 (en) | 2014-05-27 | 2015-09-01 | International Business Machines Corporation | Preparation of thioether polymers |
| US9592470B2 (en) | 2014-05-27 | 2017-03-14 | International Business Machines Corporation | Sulfur scavenging materials for filters and coatings |
| US9120899B1 (en) | 2014-06-02 | 2015-09-01 | International Business Machines Corporation | Preparation of functional polysulfones |
| US9469660B2 (en) | 2014-06-03 | 2016-10-18 | International Business Machines Corporation | Sulfur scavenging materials comprising hexahydrotriazine-modified particle |
| US9389181B2 (en) | 2014-06-06 | 2016-07-12 | International Business Machines Corporation | Methods and apparatus for detecting metals in liquids |
| US9656239B2 (en) | 2014-06-16 | 2017-05-23 | International Business Machines Corporation | Apparatus for controlling metals in liquids |
| US9296863B2 (en) | 2014-06-16 | 2016-03-29 | International Business Machines Corporation | Preparation of poly(octatriazacane) |
| US9271498B2 (en) | 2014-06-19 | 2016-03-01 | International Business Machines Corporation | Antimicrobial PHT coatings |
| US9352045B2 (en) | 2014-06-20 | 2016-05-31 | International Business Machines Corporation | Methods and materials for therapeutic delivery |
| US9512332B2 (en) | 2014-06-27 | 2016-12-06 | International Busuiness Machines Corporation | Soluble, processable polyhemiaminals and polyhexahydrotriazines |
| US9587073B2 (en) | 2014-07-24 | 2017-03-07 | International Business Machines Corporation | Thermoplastic toughening of PHT's |
| US9255172B1 (en) | 2014-08-05 | 2016-02-09 | International Business Machines Corporation | High-performance, filler-reinforced, recyclable composite materials |
| US10023735B2 (en) | 2014-08-18 | 2018-07-17 | International Business Machines Corporation | 3D printing with PHT/PHA based materials and polymerizable monomers |
| US9957345B2 (en) | 2014-08-18 | 2018-05-01 | International Business Machines Corporation | 3D printing with PHT based materials |
| US9790313B2 (en) | 2014-08-21 | 2017-10-17 | Hexion Inc. | Curing compositions and methods of preparing |
| US9453108B2 (en) | 2014-08-22 | 2016-09-27 | International Business Machines Corporation | Flame retardant PHT compositions |
| US9676891B2 (en) | 2014-08-22 | 2017-06-13 | International Business Machines Corporation | Synthesis of dynamic covalent 3D constructs |
| US9422378B2 (en) | 2014-10-09 | 2016-08-23 | International Business Machines Corporation | Hexahydrotriazine, dithiazine, and thioether functionalized materials |
| US9777116B2 (en) | 2014-10-16 | 2017-10-03 | International Business Machines Corporation | Porous/nanoporous PHT |
| US9303186B1 (en) | 2014-10-16 | 2016-04-05 | International Business Machines Corporation | PHT powder coating materials |
| US10080806B2 (en) | 2015-08-19 | 2018-09-25 | International Business Machines Corporation | Sulfur-containing polymers from hexahydrotriazine and dithiol precursors as a carrier for active agents |
| US9758620B2 (en) | 2015-09-03 | 2017-09-12 | International Business Machines Corporation | Tailorable viscoelastic properties of PEG-hemiaminal organogel networks |
| US9550863B1 (en) | 2015-10-05 | 2017-01-24 | International Business Machines Corporation | Polymers from stabilized imines |
| US9534084B1 (en) | 2015-11-02 | 2017-01-03 | International Business Machines Corporation | High molecular weight polythioaminals from a single monomer |
| US9873766B2 (en) | 2015-11-24 | 2018-01-23 | International Business Machines Corporation | Systems chemistry approach to polyhexahydrotriazine polymeric structures |
| US9862802B2 (en) | 2015-11-30 | 2018-01-09 | International Business Machines Corporation | Poly(thioaminal) probe based lithography |
| US9828467B2 (en) | 2016-02-05 | 2017-11-28 | International Business Machines Corporation | Photoresponsive hexahydrotriazine polymers |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB928112A (en) * | 1960-05-17 | 1963-06-06 | Ici Ltd | Condensation products |
| DE1215373B (de) * | 1962-07-12 | 1966-04-28 | Bayer Ag | Verfahren zur Herstellung von linearen oder verzweigten Polypropylenglykolaethern mit Aminogruppen |
| US3461100A (en) * | 1964-07-02 | 1969-08-12 | Tracor | Condensation products of aldehydes or ketones with diamines and monoamines |
| DE4006537A1 (de) * | 1990-03-02 | 1991-09-05 | Basf Ag | Zweikomponentenklebstoffe auf polyisocyanat-polyazomethinbasis und ihre verwendung |
| US5830243A (en) * | 1997-09-11 | 1998-11-03 | The Lubrizol Corporation | Fuel compositions containing N-substituted perahydro-s triazines |
-
2000
- 2000-06-23 DE DE2000130684 patent/DE10030684A1/de not_active Withdrawn
-
2001
- 2001-06-22 WO PCT/EP2001/007134 patent/WO2001098388A1/fr not_active Ceased
- 2001-06-22 AU AU2001283881A patent/AU2001283881A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO2001098388A1 (fr) | 2001-12-27 |
| AU2001283881A1 (en) | 2002-01-02 |
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