EA017131B1 - Композиция удлинителя цепи на основе диамина, полимер и способ его получения - Google Patents
Композиция удлинителя цепи на основе диамина, полимер и способ его получения Download PDFInfo
- Publication number
- EA017131B1 EA017131B1 EA200970324A EA200970324A EA017131B1 EA 017131 B1 EA017131 B1 EA 017131B1 EA 200970324 A EA200970324 A EA 200970324A EA 200970324 A EA200970324 A EA 200970324A EA 017131 B1 EA017131 B1 EA 017131B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- diamine
- aliphatic
- group
- aromatic
- ring
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 78
- 239000004970 Chain extender Substances 0.000 title claims abstract description 23
- 238000000034 method Methods 0.000 title claims abstract description 21
- 229920000642 polymer Polymers 0.000 title claims description 31
- 125000004427 diamine group Chemical group 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 83
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 78
- 150000004985 diamines Chemical class 0.000 claims abstract description 70
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 claims abstract description 62
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 44
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims abstract description 35
- 229910000071 diazene Inorganic materials 0.000 claims abstract description 35
- 125000001841 imino group Chemical group [H]N=* 0.000 claims abstract description 27
- -1 3,3dimethyl-2-butyl Chemical group 0.000 claims description 61
- 125000003277 amino group Chemical group 0.000 claims description 58
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 229920005862 polyol Polymers 0.000 claims description 22
- 150000003077 polyols Chemical class 0.000 claims description 22
- 239000012948 isocyanate Substances 0.000 claims description 16
- 150000002513 isocyanates Chemical class 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 11
- 229920001228 polyisocyanate Polymers 0.000 claims description 11
- 239000005056 polyisocyanate Substances 0.000 claims description 11
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 claims description 10
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 10
- 229920000570 polyether Polymers 0.000 claims description 10
- RQEOBXYYEPMCPJ-UHFFFAOYSA-N 4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N RQEOBXYYEPMCPJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000004615 ingredient Substances 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 8
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 claims description 7
- QMJFEXXFZLBNAC-UHFFFAOYSA-N 7,8,8-trimethylnonane-1,6-diamine Chemical compound CC(C)(C)C(C)C(N)CCCCCN QMJFEXXFZLBNAC-UHFFFAOYSA-N 0.000 claims description 5
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000012634 fragment Substances 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229920002396 Polyurea Polymers 0.000 abstract description 24
- 229920002635 polyurethane Polymers 0.000 abstract description 17
- 239000004814 polyurethane Substances 0.000 abstract description 17
- 125000002312 hydrocarbylidene group Chemical group 0.000 abstract description 4
- 239000000306 component Substances 0.000 description 38
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
- 239000000126 substance Substances 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
- 150000004984 aromatic diamines Chemical class 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000001879 gelation Methods 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 230000003068 static effect Effects 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 3
- JGYUBHGXADMAQU-UHFFFAOYSA-N 2,4,6-triethylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(CC)=C1N JGYUBHGXADMAQU-UHFFFAOYSA-N 0.000 description 3
- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 description 3
- NGRMNIHDBVGDOO-UHFFFAOYSA-N 4,6-di(butan-2-yl)-2-methylbenzene-1,3-diamine Chemical compound CCC(C)C1=CC(C(C)CC)=C(N)C(C)=C1N NGRMNIHDBVGDOO-UHFFFAOYSA-N 0.000 description 3
- NWIVYGKSHSJHEF-UHFFFAOYSA-N 4-[(4-amino-3,5-diethylphenyl)methyl]-2,6-diethylaniline Chemical compound CCC1=C(N)C(CC)=CC(CC=2C=C(CC)C(N)=C(CC)C=2)=C1 NWIVYGKSHSJHEF-UHFFFAOYSA-N 0.000 description 3
- 125000001118 alkylidene group Chemical group 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- CUJPFPXNDSIBPG-UHFFFAOYSA-N 1,3-propanediyl Chemical group [CH2]C[CH2] CUJPFPXNDSIBPG-UHFFFAOYSA-N 0.000 description 2
- FHMPFSKGDPKPDJ-UHFFFAOYSA-N 2,3,6-trimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1C FHMPFSKGDPKPDJ-UHFFFAOYSA-N 0.000 description 2
- AKZOLEPNYXGNEH-UHFFFAOYSA-N 4-methyl-2,6-di(propan-2-yl)benzene-1,3-diamine Chemical compound CC(C)C1=CC(C)=C(N)C(C(C)C)=C1N AKZOLEPNYXGNEH-UHFFFAOYSA-N 0.000 description 2
- JFQJDZQPICZGJF-UHFFFAOYSA-N 4-tert-butylbenzene-1,3-diamine Chemical compound CC(C)(C)C1=CC=C(N)C=C1N JFQJDZQPICZGJF-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 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 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
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- 230000009466 transformation Effects 0.000 description 2
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- IFKPLJWIEQBPGG-QGZVFWFLSA-N (5s)-6-(dimethylamino)-5-methyl-4,4-diphenylhexan-3-one Chemical compound C=1C=CC=CC=1C([C@H](C)CN(C)C)(C(=O)CC)C1=CC=CC=C1 IFKPLJWIEQBPGG-QGZVFWFLSA-N 0.000 description 1
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- JIABEENURMZTTI-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatophenyl)methyl]benzene Chemical class O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O JIABEENURMZTTI-UHFFFAOYSA-N 0.000 description 1
- BQJNDFXBOSXMLM-UHFFFAOYSA-N 2,3,5,6-tetraethylbenzene-1,4-diamine Chemical compound CCC1=C(N)C(CC)=C(CC)C(N)=C1CC BQJNDFXBOSXMLM-UHFFFAOYSA-N 0.000 description 1
- HNEIEUKJFTUIBM-UHFFFAOYSA-N 2,3,5-tripropylbenzene-1,4-diamine Chemical compound CCCC1=CC(N)=C(CCC)C(CCC)=C1N HNEIEUKJFTUIBM-UHFFFAOYSA-N 0.000 description 1
- RTJHFPLPPWYGIF-UHFFFAOYSA-N 2,3-di(butan-2-yl)aniline Chemical compound CCC(C)C1=CC=CC(N)=C1C(C)CC RTJHFPLPPWYGIF-UHFFFAOYSA-N 0.000 description 1
- ABQQPHFTJYCSIA-UHFFFAOYSA-N 2,3-diethylbenzene-1,4-diamine Chemical compound CCC1=C(N)C=CC(N)=C1CC ABQQPHFTJYCSIA-UHFFFAOYSA-N 0.000 description 1
- USRBRYHXYFBBHZ-UHFFFAOYSA-N 2,3-dihexylaniline Chemical compound CCCCCCC1=CC=CC(N)=C1CCCCCC USRBRYHXYFBBHZ-UHFFFAOYSA-N 0.000 description 1
- OKHJOGBJBSEFMP-UHFFFAOYSA-N 2,4,5,6-tetrapropylbenzene-1,3-diamine Chemical compound CCCC1=C(N)C(CCC)=C(CCC)C(CCC)=C1N OKHJOGBJBSEFMP-UHFFFAOYSA-N 0.000 description 1
- JWTVQZQPKHXGFM-UHFFFAOYSA-N 2,5-dimethylhexane-2,5-diamine Chemical compound CC(C)(N)CCC(C)(C)N JWTVQZQPKHXGFM-UHFFFAOYSA-N 0.000 description 1
- OBEARTBLLJIVLW-UHFFFAOYSA-N 2,5-dioctylbenzene-1,4-diamine Chemical compound CCCCCCCCC1=CC(N)=C(CCCCCCCC)C=C1N OBEARTBLLJIVLW-UHFFFAOYSA-N 0.000 description 1
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- DDTKYVBFPULMGN-UHFFFAOYSA-N 2-methyl-6-propan-2-ylaniline Chemical compound CC(C)C1=CC=CC(C)=C1N DDTKYVBFPULMGN-UHFFFAOYSA-N 0.000 description 1
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- HLOXRRSFYXEJMC-UHFFFAOYSA-N 2-propan-2-ylbenzene-1,3-diamine Chemical compound CC(C)C1=C(N)C=CC=C1N HLOXRRSFYXEJMC-UHFFFAOYSA-N 0.000 description 1
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- BVSIOHHIXOTRME-UHFFFAOYSA-N 3-[(3-amino-2,6-diphenylphenyl)methyl]-2,4-diphenylaniline Chemical compound C1=CC=C(C=C1)C2=C(C(=C(C=C2)N)C3=CC=CC=C3)CC4=C(C=CC(=C4C5=CC=CC=C5)N)C6=CC=CC=C6 BVSIOHHIXOTRME-UHFFFAOYSA-N 0.000 description 1
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- HWDBTRIBMNSAOG-UHFFFAOYSA-N 5-[[3-amino-4,5-di(propan-2-yl)phenyl]methyl]-2,3-di(propan-2-yl)aniline Chemical compound NC1=C(C(C)C)C(C(C)C)=CC(CC=2C=C(C(C(C)C)=C(N)C=2)C(C)C)=C1 HWDBTRIBMNSAOG-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- 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
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- 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
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- 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
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Landscapes
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- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/534,968 US7964695B2 (en) | 2005-03-28 | 2006-09-25 | Chain extenders |
| PCT/US2007/068384 WO2008039571A1 (en) | 2006-09-25 | 2007-05-07 | Diamine chain extender compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200970324A1 EA200970324A1 (ru) | 2009-08-28 |
| EA017131B1 true EA017131B1 (ru) | 2012-10-30 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200970324A EA017131B1 (ru) | 2006-09-25 | 2007-05-07 | Композиция удлинителя цепи на основе диамина, полимер и способ его получения |
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| Country | Link |
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| US (2) | US7964695B2 (enExample) |
| EP (1) | EP2078048A1 (enExample) |
| JP (1) | JP2010504400A (enExample) |
| KR (1) | KR20090074159A (enExample) |
| CN (1) | CN101516948B (enExample) |
| AU (1) | AU2007300409B2 (enExample) |
| BR (1) | BRPI0716043A2 (enExample) |
| CA (1) | CA2661513A1 (enExample) |
| EA (1) | EA017131B1 (enExample) |
| WO (1) | WO2008039571A1 (enExample) |
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| EP2143707B1 (en) * | 2005-03-28 | 2018-04-11 | Line-X LLC | Secondary diamine |
| US8076518B2 (en) * | 2005-03-28 | 2011-12-13 | Albemarle Corporation | Chain extenders |
| US7964695B2 (en) * | 2005-03-28 | 2011-06-21 | Albemarle Corporation | Chain extenders |
| BRPI0809262A2 (pt) * | 2007-01-10 | 2014-10-07 | Albemarle Corp | Revestimento por aspersão; processo para formação de um revestimento por aspersão; artigo formado através da moldagem por injeção de reação; e processo para preparação de um produto de moldagem por injeção de reação. |
| US20090035350A1 (en) | 2007-08-03 | 2009-02-05 | John Stankus | Polymers for implantable devices exhibiting shape-memory effects |
| US9259515B2 (en) | 2008-04-10 | 2016-02-16 | Abbott Cardiovascular Systems Inc. | Implantable medical devices fabricated from polyurethanes with grafted radiopaque groups |
| WO2014144539A2 (en) * | 2013-03-15 | 2014-09-18 | The Board Of Trustees Of The University Of Illinois | Dynamic urea bonds for reversible and self-healing polymers |
| US10507621B2 (en) * | 2014-06-11 | 2019-12-17 | Basf Se | Polyurethane compound for producing an integrated insulation component |
| CN107663671B (zh) * | 2017-08-16 | 2020-07-28 | 东华大学 | 一种耐热聚氨酯弹性纤维及其制备方法 |
| CN107686548B (zh) * | 2017-08-22 | 2021-12-10 | 山西省建筑科学研究院 | 水性纯聚脲的制备方法 |
| JP7171956B1 (ja) | 2022-03-29 | 2022-11-15 | アイカ工業株式会社 | コンクリート床用目地材組成物及びその施工方法及びコンクリート床 |
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2007
- 2007-05-07 WO PCT/US2007/068384 patent/WO2008039571A1/en not_active Ceased
- 2007-05-07 BR BRPI0716043-7A patent/BRPI0716043A2/pt not_active IP Right Cessation
- 2007-05-07 KR KR1020097005110A patent/KR20090074159A/ko not_active Withdrawn
- 2007-05-07 JP JP2009529282A patent/JP2010504400A/ja active Pending
- 2007-05-07 CN CN2007800354095A patent/CN101516948B/zh not_active Expired - Fee Related
- 2007-05-07 CA CA002661513A patent/CA2661513A1/en not_active Abandoned
- 2007-05-07 AU AU2007300409A patent/AU2007300409B2/en not_active Ceased
- 2007-05-07 EP EP07783397A patent/EP2078048A1/en not_active Withdrawn
- 2007-05-07 EA EA200970324A patent/EA017131B1/ru not_active IP Right Cessation
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2011
- 2011-02-16 US US13/028,579 patent/US8080626B2/en not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| US20070270566A1 (en) | 2007-11-22 |
| BRPI0716043A2 (pt) | 2013-01-08 |
| US8080626B2 (en) | 2011-12-20 |
| CN101516948A (zh) | 2009-08-26 |
| AU2007300409B2 (en) | 2010-10-14 |
| US7964695B2 (en) | 2011-06-21 |
| EP2078048A1 (en) | 2009-07-15 |
| WO2008039571A1 (en) | 2008-04-03 |
| AU2007300409A1 (en) | 2008-04-03 |
| KR20090074159A (ko) | 2009-07-06 |
| CA2661513A1 (en) | 2008-04-03 |
| JP2010504400A (ja) | 2010-02-12 |
| CN101516948B (zh) | 2012-08-15 |
| US20110137005A1 (en) | 2011-06-09 |
| EA200970324A1 (ru) | 2009-08-28 |
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