CA1077515A - Polyurethane elastomers prepared from diamine curing agents - Google Patents
Polyurethane elastomers prepared from diamine curing agentsInfo
- Publication number
- CA1077515A CA1077515A CA222,001A CA222001A CA1077515A CA 1077515 A CA1077515 A CA 1077515A CA 222001 A CA222001 A CA 222001A CA 1077515 A CA1077515 A CA 1077515A
- Authority
- CA
- Canada
- Prior art keywords
- urethane
- curing agent
- moles
- isocyanate
- product
- 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.)
- Expired
Links
- 239000003795 chemical substances by application Substances 0.000 title claims description 45
- 150000004985 diamines Chemical class 0.000 title abstract description 24
- 229920003225 polyurethane elastomer Polymers 0.000 title description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000012948 isocyanate Substances 0.000 claims abstract description 26
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 26
- 239000004814 polyurethane Substances 0.000 claims abstract description 15
- 229920002635 polyurethane Polymers 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 22
- 229920000642 polymer Polymers 0.000 claims description 12
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000012943 hotmelt Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 229920000570 polyether Polymers 0.000 claims description 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 claims 1
- 229940126214 compound 3 Drugs 0.000 claims 1
- 238000001723 curing Methods 0.000 description 40
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 7
- 229940035437 1,3-propanediol Drugs 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 5
- HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 0.000 description 5
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- 229940043375 1,5-pentanediol Drugs 0.000 description 3
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 3
- 238000005915 ammonolysis reaction Methods 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- YPACMOORZSDQDQ-UHFFFAOYSA-N 3-(4-aminobenzoyl)oxypropyl 4-aminobenzoate Chemical compound C1=CC(N)=CC=C1C(=O)OCCCOC(=O)C1=CC=C(N)C=C1 YPACMOORZSDQDQ-UHFFFAOYSA-N 0.000 description 2
- DGEHMXCYTLBOBT-UHFFFAOYSA-N 3-(4-nitrobenzoyl)oxypropyl 4-nitrobenzoate Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)OCCCOC(=O)C1=CC=C([N+]([O-])=O)C=C1 DGEHMXCYTLBOBT-UHFFFAOYSA-N 0.000 description 2
- FPRLNMVVNVKDJM-UHFFFAOYSA-N 3-hydroxypropyl 1,4-diaminocyclohexa-2,4-diene-1-carboxylate Chemical compound NC1(C(=O)OCCCO)CC=C(C=C1)N FPRLNMVVNVKDJM-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- BVXQWCXVRCYRRZ-UHFFFAOYSA-N 4-(2-aminobenzoyl)oxybutyl 2-aminobenzoate Chemical compound NC1=CC=CC=C1C(=O)OCCCCOC(=O)C1=CC=CC=C1N BVXQWCXVRCYRRZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229940064734 aminobenzoate Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- -1 diamine compound Chemical class 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 238000007416 differential thermogravimetric analysis Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000011527 polyurethane coating Substances 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000004781 supercooling Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 230000004580 weight loss Effects 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S528/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S528/906—Fiber or elastomer prepared from an isocyanate reactant
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA342,444A CA1089594A (en) | 1974-03-14 | 1979-12-21 | Polyurethane elastomers prepared from diamine curing agents |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45107974A | 1974-03-14 | 1974-03-14 | |
| US05/462,763 US3932360A (en) | 1974-03-14 | 1974-04-22 | Polyurethane elastomers prepared from diamine curing agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1077515A true CA1077515A (en) | 1980-05-13 |
Family
ID=27036237
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA222,001A Expired CA1077515A (en) | 1974-03-14 | 1975-03-13 | Polyurethane elastomers prepared from diamine curing agents |
Country Status (7)
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4186257A (en) * | 1977-02-15 | 1980-01-29 | Bayer Aktiengesellschaft | Process for the preparation of new segmented polyurethane resins derived from block copolymers being linked together through ester and/or urethane and/or urea groups |
| JPS5480397A (en) * | 1977-12-09 | 1979-06-27 | Ihara Chem Ind Co Ltd | Production of polyurethane elastomer |
| SE440773B (sv) * | 1977-12-12 | 1985-08-19 | Bofors Ab | Sett att framstella 1,3-propandiol-di-p-aminobensoat |
| DE2902740A1 (de) * | 1979-01-25 | 1980-08-07 | Hoechst Ag | Verfahren zur herstellung von alkandiol-bis-amino-benzoesaeureestern |
| US4328322A (en) * | 1979-12-03 | 1982-05-04 | Polaroid Corporation | Synthetic polymers by polyisocyanate polyaddition process |
| WO1982001709A1 (en) * | 1980-11-10 | 1982-05-27 | Corp Polaroid | Synthetic polymers by polyisocyanate polyaddition process |
| US4401649A (en) * | 1981-07-20 | 1983-08-30 | Polaroid Corporation | Sunscreen method |
| US4404353A (en) * | 1981-08-20 | 1983-09-13 | Dataproducts Corporation | Urethane elastomer for printing belts and process therefor |
| JPS5989322A (ja) * | 1982-11-13 | 1984-05-23 | Toyo Tire & Rubber Co Ltd | ポリウレタンウレア重合体及びその製造法 |
| US4559400A (en) * | 1983-08-01 | 1985-12-17 | American Cyanamid Company | Polymer from aromatic diamine and N,N,N',N'-tetraglycidyl-1,3-propylene bis(p-aminobenzoate) |
| US4623681A (en) | 1983-08-01 | 1986-11-18 | American Cyanamid Company | Curable epoxy resin compositions |
| EP0133281A3 (en) * | 1983-08-01 | 1988-11-30 | American Cyanamid Company | Curable fibre reinforced epoxy resin composition |
| US4558078A (en) * | 1983-08-01 | 1985-12-10 | American Cyanamid Company | Curable epoxy resin compositions |
| US4636535A (en) * | 1983-08-01 | 1987-01-13 | American Cyanamid Company | Curable epoxy resin compositions |
| US4533686A (en) * | 1983-08-01 | 1985-08-06 | American Cyanamid Co. | Curable epoxy resin compositions |
| US4562217A (en) * | 1983-08-01 | 1985-12-31 | American Cyanamid | Curable epoxy resin compositions |
| US4518786A (en) * | 1983-08-01 | 1985-05-21 | American Cyanamid Company | N,N,N',N'-tetraglycidyl-1,3-propylene bis(p-aminobenzoate |
| US4623746A (en) | 1983-08-01 | 1986-11-18 | American Cyanamid Company | Alkyleneglycol-bis(4-methylaminobenzoates) |
| US4537945A (en) * | 1984-04-02 | 1985-08-27 | Toyo Tire & Rubber Company Limited | Polyether derivative and a poly(urethane)ureamide obtained therefrom |
| DE3534947A1 (de) * | 1985-10-01 | 1987-04-09 | Bayer Ag | Verfahren zur herstellung von polyaminen, polyamine und deren verwendung zur herstellung von polyurethanen |
| US4683333A (en) * | 1985-11-22 | 1987-07-28 | The Dow Chemical Company | Process for preparing substituted bis-ethers |
| US4851562A (en) * | 1986-12-03 | 1989-07-25 | Akzo N.V. | Aromatic amide groups-containing diamines and polymers in which these diamines are incorporated |
| US5183877A (en) * | 1991-10-25 | 1993-02-02 | H. B. Fuller Company | Polyurea or polyurea-urethane adhesive for bonding elastomers |
| US5233009A (en) * | 1991-11-07 | 1993-08-03 | Miles Inc. | Polyurethanes comprising the reaction of an isocyanate terminated prepolymer and a polyol mixture comprising triols and an organic diamine |
| US5192594A (en) * | 1991-11-07 | 1993-03-09 | Miles Inc. | Process for the preparation of a polyurethane structural support |
| JP3220873B2 (ja) * | 1992-07-02 | 2001-10-22 | イハラケミカル工業株式会社 | ポリウレタンウレアエラストマー |
| US5719307A (en) * | 1994-04-13 | 1998-02-17 | Air Products And Chemicals, Inc. | Diamine chain extenders and method of use |
| EP0677542B1 (en) * | 1994-04-13 | 1999-06-23 | Air Products And Chemicals, Inc. | Diamine chain extenders in polyurethane-ureas and process of manufacture |
| US5371288A (en) * | 1994-04-13 | 1994-12-06 | Air Products And Chemicals, Inc. | Branched alkyl-containing aminobenzamides as chain extenders in polyurethane-urea elastomers |
| US6127505A (en) * | 1995-02-02 | 2000-10-03 | Simula Inc. | Impact resistant polyurethane and method of manufacture thereof |
| US6258917B1 (en) | 1996-05-21 | 2001-07-10 | Simula, Inc. | Extrudable thermoplastic elastomeric urea-extended polyurethane |
| US5811506A (en) * | 1997-02-03 | 1998-09-22 | Simula Inc. | Extrudable thermoplastic elastomeric urea-extended polyurethane |
| US6111129A (en) * | 1998-11-04 | 2000-08-29 | Uniroyal Chemical Company, Inc. | Process for the preparation of alkanediol-diaminobenzoates |
| IL129583A (en) | 1999-04-25 | 2005-05-17 | Kenneth I Sawyer | Diesters of oligobutyleneglycol and amidine benzoic acid and their use for preparation of moisture-curable, storage-stable, one-part polyurethane/urea compositions |
| CN1261312C (zh) * | 2000-09-11 | 2006-06-28 | 陶氏环球技术公司 | 漏气保用轮胎支架 |
| US6887063B2 (en) * | 2000-09-11 | 2005-05-03 | Dow Global Technologies Inc. | Processing mold including unitary movable mandrel for preparing tire support |
| CA2447769C (en) * | 2001-06-13 | 2011-07-26 | Energy & Environmental International, L.C. | Bulk polymerization reactors and methods for polymerization |
| US20030212291A1 (en) * | 2002-05-02 | 2003-11-13 | Crompton Corporation | Diamine curing agents for the preparation of polyurethane-urea elastomers |
| US20040052690A1 (en) * | 2002-09-12 | 2004-03-18 | Eaton Gerald B. | Polymerization reactant injection system |
| US7572461B2 (en) * | 2004-03-05 | 2009-08-11 | Kenneth I. Sawyer | Borer-resistant wood, wood products, and wooden structures and methods |
| CA2566605A1 (en) * | 2004-05-14 | 2005-12-01 | Kenneth I. Sawyer | Polyurea compositions and compounds for the preparation thereof |
| CN101077904B (zh) * | 2006-05-25 | 2010-08-04 | 远东新世纪股份有限公司 | 热塑性聚氨酯及其使用 |
| GB201000182D0 (en) * | 2010-01-07 | 2010-02-24 | Hexcel Composites Ltd | Novel curable resins and curing agents therefor |
| CN108699214A (zh) | 2016-02-23 | 2018-10-23 | 伊士曼化工公司 | 异氰酸酯改性硬质热塑性聚合物组合物 |
| US11208520B2 (en) | 2016-02-23 | 2021-12-28 | Eastman Chemical Company | Isocyanate-modified rigid thermoplastic polymer compositions |
| CN120569421A (zh) | 2023-01-20 | 2025-08-29 | 赢创运营有限公司 | 生物基胺固化剂和聚脲组合物 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3817940A (en) * | 1970-08-17 | 1974-06-18 | Bayer Ag | Aromatic diamines |
-
1974
- 1974-04-22 US US05/462,763 patent/US3932360A/en not_active Expired - Lifetime
-
1975
- 1975-03-12 IT IT48580/75A patent/IT1032296B/it active
- 1975-03-13 FR FR7507883A patent/FR2264005B1/fr not_active Expired
- 1975-03-13 CA CA222,001A patent/CA1077515A/en not_active Expired
- 1975-03-13 DE DE2511093A patent/DE2511093C2/de not_active Expired
- 1975-03-13 DE DE2560419A patent/DE2560419C2/de not_active Expired
- 1975-03-13 DE DE2560030A patent/DE2560030C2/de not_active Expired
- 1975-03-14 GB GB10678/75A patent/GB1502471A/en not_active Expired
- 1975-03-14 GB GB38917/77A patent/GB1502472A/en not_active Expired
- 1975-03-14 JP JP3098775A patent/JPS5410030B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2560030C2 (de) | 1980-10-02 |
| JPS50132096A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-10-18 |
| DE2511093C2 (de) | 1985-03-14 |
| FR2264005B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-03-21 |
| DE2511093A1 (de) | 1975-09-18 |
| FR2264005A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-10-10 |
| US3932360A (en) | 1976-01-13 |
| IT1032296B (it) | 1979-05-30 |
| DE2560030B1 (de) | 1980-02-07 |
| GB1502471A (en) | 1978-03-01 |
| JPS5410030B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-05-01 |
| GB1502472A (en) | 1978-03-01 |
| DE2560419C2 (de) | 1985-10-03 |
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