CA2111421A1 - Fast-curing, high strength, two-part sealants using acetoacetate-amine cure chemistry - Google Patents
Fast-curing, high strength, two-part sealants using acetoacetate-amine cure chemistryInfo
- Publication number
- CA2111421A1 CA2111421A1 CA002111421A CA2111421A CA2111421A1 CA 2111421 A1 CA2111421 A1 CA 2111421A1 CA 002111421 A CA002111421 A CA 002111421A CA 2111421 A CA2111421 A CA 2111421A CA 2111421 A1 CA2111421 A1 CA 2111421A1
- Authority
- CA
- Canada
- Prior art keywords
- terminated
- acetoacetate
- amine
- component
- molecular weight
- 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
- 239000000565 sealant Substances 0.000 title claims abstract description 67
- 239000000203 mixture Substances 0.000 claims abstract description 44
- 229920000570 polyether Polymers 0.000 claims abstract description 24
- 229920000728 polyester Polymers 0.000 claims abstract description 20
- 239000006229 carbon black Substances 0.000 claims abstract description 12
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical group CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims description 44
- 229920005862 polyol Polymers 0.000 claims description 42
- 150000003077 polyols Chemical class 0.000 claims description 42
- 229920000642 polymer Polymers 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 239000000463 material Substances 0.000 claims description 19
- 229920000768 polyamine Polymers 0.000 claims description 18
- 150000002009 diols Chemical class 0.000 claims description 17
- 239000002245 particle Substances 0.000 claims description 17
- 238000004132 cross linking Methods 0.000 claims description 14
- 238000002156 mixing Methods 0.000 claims description 11
- 239000003431 cross linking reagent Substances 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 4
- 150000004072 triols Chemical class 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims 2
- 229920001519 homopolymer Polymers 0.000 claims 2
- 239000004721 Polyphenylene oxide Substances 0.000 abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 13
- 239000007788 liquid Substances 0.000 abstract description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 6
- 239000003963 antioxidant agent Substances 0.000 abstract description 4
- 239000000654 additive Substances 0.000 abstract description 3
- 239000011248 coating agent Substances 0.000 abstract description 3
- 238000000576 coating method Methods 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 238000013329 compounding Methods 0.000 abstract description 2
- 239000003112 inhibitor Substances 0.000 abstract description 2
- 239000000306 component Substances 0.000 description 56
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 44
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 239000000047 product Substances 0.000 description 34
- 239000003054 catalyst Substances 0.000 description 33
- -1 alkyl acetoacetate Chemical compound 0.000 description 31
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 29
- 150000001412 amines Chemical class 0.000 description 29
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 21
- 238000004821 distillation Methods 0.000 description 18
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 16
- 229920002239 polyacrylonitrile Polymers 0.000 description 14
- 229940113165 trimethylolpropane Drugs 0.000 description 14
- 238000007792 addition Methods 0.000 description 13
- 235000019589 hardness Nutrition 0.000 description 13
- 238000010992 reflux Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 229960005419 nitrogen Drugs 0.000 description 11
- 229920002176 Pluracol® Polymers 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 241000894007 species Species 0.000 description 10
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000376 reactant Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical group 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- 239000003039 volatile agent Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 238000005576 amination reaction Methods 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 239000004632 polycaprolactone Substances 0.000 description 5
- 229920001451 polypropylene glycol Polymers 0.000 description 5
- 239000012763 reinforcing filler Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 4
- 241000557626 Corvus corax Species 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 229920005906 polyester polyol Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000002318 adhesion promoter Substances 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920001610 polycaprolactone Polymers 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 description 2
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 239000004594 Masterbatch (MB) Substances 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical class [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
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- 238000007254 oxidation reaction Methods 0.000 description 2
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- 150000002989 phenols Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000012744 reinforcing agent Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000012974 tin catalyst Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
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- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical class C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- BKUSIKGSPSFQAC-RRKCRQDMSA-N 2'-deoxyinosine-5'-diphosphate Chemical compound O1[C@H](CO[P@@](O)(=O)OP(O)(O)=O)[C@@H](O)C[C@@H]1N1C(NC=NC2=O)=C2N=C1 BKUSIKGSPSFQAC-RRKCRQDMSA-N 0.000 description 1
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- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- KFVIYKFKUYBKTP-UHFFFAOYSA-N 2-n-(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCNC1=NC(N)=NC(N)=N1 KFVIYKFKUYBKTP-UHFFFAOYSA-N 0.000 description 1
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- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
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- 239000003960 organic solvent Substances 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 239000004591 urethane sealant Substances 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/02—Polyamines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2003/1034—Materials or components characterised by specific properties
- C09K2003/1078—Fire-resistant, heat-resistant materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/02—Inorganic compounds
- C09K2200/0204—Elements
- C09K2200/0208—Carbon
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
- C09K2200/0615—Macromolecular organic compounds, e.g. prepolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09K2200/063—Polyacrylonitriles
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
- C09K2200/0645—Macromolecular organic compounds, e.g. prepolymers obtained otherwise than by reactions involving carbon-to-carbon unsaturated bonds
- C09K2200/0655—Polyesters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
- C09K2200/0645—Macromolecular organic compounds, e.g. prepolymers obtained otherwise than by reactions involving carbon-to-carbon unsaturated bonds
- C09K2200/0657—Polyethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
- C09K2200/0645—Macromolecular organic compounds, e.g. prepolymers obtained otherwise than by reactions involving carbon-to-carbon unsaturated bonds
- C09K2200/0657—Polyethers
- C09K2200/066—Polyester-polyethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
- C09K2200/0645—Macromolecular organic compounds, e.g. prepolymers obtained otherwise than by reactions involving carbon-to-carbon unsaturated bonds
- C09K2200/0657—Polyethers
- C09K2200/0662—Polyether-polyol
-
- 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
- Y10S524/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S524/906—Multipackage compositions
-
- 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
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/939—Multipackage system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Sealing Material Composition (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US99322692A | 1992-12-18 | 1992-12-18 | |
| US07/993,226 | 1992-12-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2111421A1 true CA2111421A1 (en) | 1994-06-19 |
Family
ID=25539266
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002111421A Abandoned CA2111421A1 (en) | 1992-12-18 | 1993-12-14 | Fast-curing, high strength, two-part sealants using acetoacetate-amine cure chemistry |
Country Status (8)
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9315092D0 (en) * | 1993-07-21 | 1993-09-01 | Zeneca Ltd | Crosslinkable coating compositions |
| DE19502833A1 (de) * | 1995-01-30 | 1996-08-01 | Schmalbach Lubeca | Dichtungsmassen für Verpackungen, insbesondere Metallverpackungen |
| CN1154700C (zh) * | 1995-05-26 | 2004-06-23 | 艾狄航空涂料公司 | 含有聚乙酰乙酸酯、交联剂和有机硅烷的涂料组合物 |
| US6833408B2 (en) * | 1995-12-18 | 2004-12-21 | Cohesion Technologies, Inc. | Methods for tissue repair using adhesive materials |
| US7883693B2 (en) * | 1995-12-18 | 2011-02-08 | Angiodevice International Gmbh | Compositions and systems for forming crosslinked biomaterials and methods of preparation of use |
| PT1704878E (pt) | 1995-12-18 | 2013-07-17 | Angiodevice Internat Gmbh | Composições de polímeros reticulados e métodos para a sua utilização |
| US5714563A (en) * | 1996-01-16 | 1998-02-03 | Depompei; Michael Frederick | One-part, low viscosity, moisture curable composition |
| WO1998012274A1 (en) * | 1996-09-23 | 1998-03-26 | Chandrashekar Pathak | Methods and devices for preparing protein concentrates |
| US20090324721A1 (en) * | 1996-09-23 | 2009-12-31 | Jack Kennedy | Hydrogels Suitable For Use In Polyp Removal |
| US8003705B2 (en) * | 1996-09-23 | 2011-08-23 | Incept Llc | Biocompatible hydrogels made with small molecule precursors |
| US5913970A (en) * | 1997-01-16 | 1999-06-22 | Eastman Chemical Company | Stabilized non-polymeric acetoacetate esters that promote adhesion to metallic and oxidized substrates |
| CA2348895C (en) | 1998-11-20 | 2005-04-12 | The Sherwin-Williams Company | Curable compositions comprising acetoacetoxy and imine functionality |
| EP1137373A4 (en) | 1998-12-04 | 2004-05-19 | Chandrashekhar P Pathak | BIOCOMPATIBLE, CROSSLINKED POLYMERS |
| ES2203482T3 (es) * | 1999-05-05 | 2004-04-16 | E.I. Du Pont De Nemours And Company | Composiciones de recubrimiento que contienen macromoleculas altamente estructuradas. |
| WO2003071986A2 (en) * | 2002-02-22 | 2003-09-04 | Control Delivery Systems, Inc. | Method for treating otic disorders |
| EP1431328A1 (de) * | 2002-12-19 | 2004-06-23 | Sika Technology AG | 3-(N-Silyalkyl)-amino-propenat-Gruppen enthaltendes Polymer und dessen Verwendung |
| US7776603B2 (en) * | 2003-04-01 | 2010-08-17 | Cabot Corporation | Methods of specifying or identifying particulate material |
| US7776602B2 (en) * | 2003-04-01 | 2010-08-17 | Cabot Corporation | Methods of providing product consistency |
| US20040197924A1 (en) * | 2003-04-01 | 2004-10-07 | Murphy Lawrence J. | Liquid absorptometry method of providing product consistency |
| US7776604B2 (en) * | 2003-04-01 | 2010-08-17 | Cabot Corporation | Methods of selecting and developing a particulate material |
| US7000457B2 (en) * | 2003-04-01 | 2006-02-21 | Cabot Corporation | Methods to control and/or predict rheological properties |
| CN101080246A (zh) | 2004-04-28 | 2007-11-28 | 安希奥设备国际有限责任公司 | 用于形成交联生物材料的组合物和系统及关联的制备方法与用途 |
| WO2006034128A2 (en) | 2004-09-17 | 2006-03-30 | Angiotech Biomaterials Corporation | Multifunctional compounds for forming crosslinked biomaterials and methods of preparation and use |
| US9707252B2 (en) * | 2005-02-09 | 2017-07-18 | Covidien Lp | Synthetic sealants |
| US7722713B2 (en) * | 2005-05-17 | 2010-05-25 | Cabot Corporation | Carbon blacks and polymers containing the same |
| DE102005058745A1 (de) | 2005-12-08 | 2007-06-14 | Wacker Chemie Ag | Enaminöle und Verfahren zu ihrer Herstellung |
| US8132958B2 (en) * | 2006-12-13 | 2012-03-13 | Renfro Charles K | Multi-chambered fluid mixing apparatus and method |
| US20090227981A1 (en) * | 2007-03-05 | 2009-09-10 | Bennett Steven L | Low-Swelling Biocompatible Hydrogels |
| US20090227689A1 (en) * | 2007-03-05 | 2009-09-10 | Bennett Steven L | Low-Swelling Biocompatible Hydrogels |
| ATE543520T1 (de) | 2007-04-13 | 2012-02-15 | Kuros Biosurgery Ag | Polymergewebeversiegelung |
| US8067028B2 (en) * | 2007-08-13 | 2011-11-29 | Confluent Surgical Inc. | Drug delivery device |
| US7562879B1 (en) * | 2008-04-30 | 2009-07-21 | Cnh America Llc | Method and apparatus for creating an auger arm and bearing seal |
| JP5890182B2 (ja) | 2009-02-12 | 2016-03-22 | インセプト エルエルシー | ヒドロゲルプラグによる薬物送達 |
| WO2012021258A1 (en) | 2010-08-10 | 2012-02-16 | 3M Innovative Properties Company | Epoxy structural adhesive |
| US10226417B2 (en) | 2011-09-16 | 2019-03-12 | Peter Jarrett | Drug delivery systems and applications |
| US9205150B2 (en) | 2011-12-05 | 2015-12-08 | Incept, Llc | Medical organogel processes and compositions |
| CN102875777B (zh) * | 2012-09-28 | 2015-03-04 | 湖南大学 | 一种新型环氧固化剂及其制备方法 |
| CN104449020B (zh) | 2013-09-20 | 2019-01-11 | 陶氏环球技术有限公司 | 用于涂料组合物的反应性多官能添加剂 |
| EP3050910B1 (de) * | 2015-01-28 | 2016-12-07 | Evonik Degussa GmbH | Modifizierte alkoxylierungsprodukte, die zumindest eine nicht-terminale alkoxysilylgruppe aufweisen, mit erhöhter lagerstabilität und verbesserter dehnung und der unter deren verwendung hergestellten polymere |
| JP2019515074A (ja) * | 2016-04-29 | 2019-06-06 | ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェンＨｅｎｋｅｌ ＡＧ ＆ Ｃｏ． ＫＧａＡ | アミン官能性ポリマーおよびそのようなポリマーの製造方法 |
| US11732165B2 (en) | 2017-06-13 | 2023-08-22 | Eastman Chemical Company | Low-temperature curable compositions |
| CN113166033B (zh) | 2018-12-11 | 2024-05-24 | 伊士曼化工公司 | 可固化涂料组合物 |
| EP3894509B1 (en) | 2018-12-11 | 2024-03-20 | Eastman Chemical Company | Self-curable and low temperature curable coating compositions |
| US20200181338A1 (en) * | 2018-12-11 | 2020-06-11 | Eastman Chemical Company | Bis-primary amines as cross-linkers for the curing of acetoacetylated resin compositions |
| CN114402007A (zh) * | 2019-10-15 | 2022-04-26 | Swimc有限公司 | 柔性涂料组合物 |
| US20210108023A1 (en) | 2019-10-15 | 2021-04-15 | Swimc Llc | Flexible coating composition |
| WO2021076102A1 (en) * | 2019-10-15 | 2021-04-22 | Swimc, Llc | Intumescent coating compositions effective at low temperatures |
| ES2929410T3 (es) * | 2020-05-06 | 2022-11-29 | Henkel Ag & Co Kgaa | Composición adhesiva curable para aplicaciones de unión de propósitos múltiples |
| US11713370B1 (en) | 2021-07-15 | 2023-08-01 | Hrl Laboratories, Llc | Adaptable thermoset polymers with internal dynamic bonds, and methods of making and using the same |
| US12275816B2 (en) | 2022-04-28 | 2025-04-15 | Westlake Epoxy Inc. | Epoxy resin compositions and coating systems |
| US12203265B2 (en) | 2023-01-11 | 2025-01-21 | Saudi Arabian Oil Company | Sulfur pit roof degradation mitigation |
| WO2025147405A1 (en) * | 2024-01-05 | 2025-07-10 | Swimc Llc | Acetoacetoxy functionalized polyalkylene glycols and uses thereof |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3017388A (en) * | 1958-04-17 | 1962-01-16 | Eastman Kodak Co | Resinous polymers from reaction of bis(acetoacetates) and bis(acetoacetamides) with diamines |
| JPS6178883A (ja) * | 1984-09-27 | 1986-04-22 | Hoechst Gosei Kk | 瞬硬化水性接着剤と接着方法 |
| DE3609928A1 (de) * | 1985-03-27 | 1986-10-09 | Hoechst Gosei K.K., Tokio/Tokyo | Waessrige gelzusammensetzung, verfahren zu ihrer herstellung und ihre verwendung in der metallbearbeitung |
| JPS61296078A (ja) * | 1985-06-25 | 1986-12-26 | Kanebo N S C Kk | 室温硬化型接着剤 |
| JP2639535B2 (ja) * | 1986-09-24 | 1997-08-13 | アクゾ・ナームローゼ・フェンノートシャップ | 水性のコーティング組成物 |
| JPH0757863B2 (ja) * | 1987-12-29 | 1995-06-21 | 日本合成化学工業株式会社 | 感圧性接着剤組成物 |
| US5017649A (en) * | 1988-01-19 | 1991-05-21 | Eastman Kodak Company | Low temperature Michael addition reactions |
| ATE123513T1 (de) * | 1988-10-17 | 1995-06-15 | Guertin Bros Coatings And Seal | Isocyanatfreie harze geeignet als ersatz für polyurethane. |
| US5051529A (en) * | 1988-12-12 | 1991-09-24 | Eastman Kodak Company | Method for functionalization of nucleophiles |
| US5017676A (en) * | 1989-12-18 | 1991-05-21 | Texaco Chemical Company | Acetoacetoxyethyl methacrylate in the cure of epoxy resins |
| US5021537A (en) * | 1990-04-27 | 1991-06-04 | Shell Oil Company | Polyacetoacetate-containing epoxy resin compositions |
| US5066824A (en) * | 1990-05-15 | 1991-11-19 | Mobay Corporation | Novel process for the preparation of amine-terminated compounds |
| DE4032751A1 (de) * | 1990-10-16 | 1992-04-23 | Hoechst Ag | Fluessiges beschichtungsmittel |
| DE4034279A1 (de) * | 1990-10-27 | 1992-04-30 | Bayer Ag | Verwendung von alkoxysilylaminen als haerter fuer acetoacetat- oder acetoacetamidgruppen aufweisende kunststoffvorlaeufer |
| EP0531850A2 (en) * | 1991-09-13 | 1993-03-17 | Bayer Corporation | A method of stabilizing blends of melamine and polyols |
-
1993
- 1993-12-13 AU AU52373/93A patent/AU675252B2/en not_active Ceased
- 1993-12-14 CA CA002111421A patent/CA2111421A1/en not_active Abandoned
- 1993-12-15 EP EP93120173A patent/EP0603716A1/en not_active Withdrawn
- 1993-12-15 TW TW082110630A patent/TW268044B/zh active
- 1993-12-17 MX MX9308176A patent/MX9308176A/es not_active IP Right Cessation
- 1993-12-18 KR KR1019930028787A patent/KR940014727A/ko not_active Withdrawn
- 1993-12-20 JP JP31986793A patent/JP3435199B2/ja not_active Expired - Fee Related
-
1994
- 1994-04-28 US US08/234,506 patent/US5426148A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU675252B2 (en) | 1997-01-30 |
| EP0603716A1 (en) | 1994-06-29 |
| US5426148A (en) | 1995-06-20 |
| JPH06220425A (ja) | 1994-08-09 |
| KR940014727A (ko) | 1994-07-19 |
| TW268044B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1996-01-11 |
| MX9308176A (es) | 1995-01-31 |
| AU5237393A (en) | 1994-06-30 |
| JP3435199B2 (ja) | 2003-08-11 |
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