TWI494420B - 可膨脹聚合物於密封上之用途 - Google Patents
可膨脹聚合物於密封上之用途 Download PDFInfo
- Publication number
- TWI494420B TWI494420B TW097125590A TW97125590A TWI494420B TW I494420 B TWI494420 B TW I494420B TW 097125590 A TW097125590 A TW 097125590A TW 97125590 A TW97125590 A TW 97125590A TW I494420 B TWI494420 B TW I494420B
- Authority
- TW
- Taiwan
- Prior art keywords
- polymer
- meth
- acrylate
- composition
- sealing
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 27
- 238000007789 sealing Methods 0.000 title claims description 19
- 239000000203 mixture Substances 0.000 claims abstract description 26
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 19
- 229920001515 polyalkylene glycol Polymers 0.000 claims abstract description 10
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 3
- -1 polyethylene Polymers 0.000 claims description 18
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 15
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 7
- 230000002950 deficient Effects 0.000 claims description 7
- 239000003999 initiator Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000003512 tertiary amines Chemical class 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 239000004698 Polyethylene Substances 0.000 claims description 4
- 238000007334 copolymerization reaction Methods 0.000 claims description 4
- 229920000573 polyethylene Polymers 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000178 monomer Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000002202 Polyethylene glycol Substances 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000003792 electrolyte Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 3
- 239000003566 sealing material Substances 0.000 description 3
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- OQFVHQAYAMECDW-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=NC=CN1 OQFVHQAYAMECDW-UHFFFAOYSA-N 0.000 description 1
- QUKAQDGLTMHMAL-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCC1=NC=CN1 QUKAQDGLTMHMAL-UHFFFAOYSA-N 0.000 description 1
- UATUCIKYJLUTBD-UHFFFAOYSA-N 2-(dibutylamino)ethyl 2-methylprop-2-enoate Chemical compound CCCCN(CCCC)CCOC(=O)C(C)=C UATUCIKYJLUTBD-UHFFFAOYSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- UAYUPCNOUDRHFB-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOCCOC(=O)C(C)=C UAYUPCNOUDRHFB-UHFFFAOYSA-N 0.000 description 1
- SHDIPWPAGQDYTH-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol;prop-2-enoic acid Chemical compound OC(=O)C=C.OCCN(CCO)CCO SHDIPWPAGQDYTH-UHFFFAOYSA-N 0.000 description 1
- IEVADDDOVGMCSI-UHFFFAOYSA-N 2-hydroxybutyl 2-methylprop-2-enoate Chemical compound CCC(O)COC(=O)C(C)=C IEVADDDOVGMCSI-UHFFFAOYSA-N 0.000 description 1
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 1
- KFTHUBZIEMOORC-UHFFFAOYSA-N 2-methylbut-2-enamide Chemical compound CC=C(C)C(N)=O KFTHUBZIEMOORC-UHFFFAOYSA-N 0.000 description 1
- ZXQOBTQMLMZFOW-UHFFFAOYSA-N 2-methylhex-2-enamide Chemical compound CCCC=C(C)C(N)=O ZXQOBTQMLMZFOW-UHFFFAOYSA-N 0.000 description 1
- QNSJBEIOQAHJLM-UHFFFAOYSA-N 2-piperazin-1-ylethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCN1CCNCC1 QNSJBEIOQAHJLM-UHFFFAOYSA-N 0.000 description 1
- UFQHFMGRRVQFNA-UHFFFAOYSA-N 3-(dimethylamino)propyl prop-2-enoate Chemical compound CN(C)CCCOC(=O)C=C UFQHFMGRRVQFNA-UHFFFAOYSA-N 0.000 description 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- YKXAYLPDMSGWEV-UHFFFAOYSA-N 4-hydroxybutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCO YKXAYLPDMSGWEV-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- GURGWUSKSSGTID-UHFFFAOYSA-N 5-(dimethylamino)pentyl 2-methylprop-2-enoate Chemical compound CN(C)CCCCCOC(=O)C(C)=C GURGWUSKSSGTID-UHFFFAOYSA-N 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical class CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical class CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical group N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- LYDDHZFBGNQJTB-UHFFFAOYSA-N n-(2,2-dimethylpropyl)-n',n'-dimethylprop-2-enehydrazide Chemical compound CC(C)(C)CN(N(C)C)C(=O)C=C LYDDHZFBGNQJTB-UHFFFAOYSA-N 0.000 description 1
- OSVIOFVAMHTXBO-UHFFFAOYSA-N n-(3-morpholin-4-ylpropyl)prop-2-enamide Chemical compound C=CC(=O)NCCCN1CCOCC1 OSVIOFVAMHTXBO-UHFFFAOYSA-N 0.000 description 1
- ADTJPOBHAXXXFS-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]prop-2-enamide Chemical compound CN(C)CCCNC(=O)C=C ADTJPOBHAXXXFS-UHFFFAOYSA-N 0.000 description 1
- KUTYRKSEXLKSTE-UHFFFAOYSA-N n-[5-(diethylamino)pentan-2-yl]prop-2-enamide Chemical compound CCN(CC)CCCC(C)NC(=O)C=C KUTYRKSEXLKSTE-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 125000005385 peroxodisulfate group Chemical group 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001012 protector Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 238000007717 redox polymerization reaction Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 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
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-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
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
-
- 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
- C09K2003/104—Water-swellable 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
- C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
- C09K2200/0615—Macromolecular organic compounds, e.g. prepolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09K2200/0625—Polyacrylic esters or derivatives thereof
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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
已經知道可膨脹聚合物及其於密封上之用途。例如，日本專利申請案JP 62－129376提出一種適合用於防止廢水通道的密封失效且不會釋出廢水之組成物。此組成物包含(甲基)丙烯酸鹽(特別是鎂或鈉鹽)、聚二(甲基)丙烯酸乙二醇酯(特別是水溶性聚(甲基)丙烯酸乙二醇酯，其可含有20－30重量%的單(甲基)丙烯酸酯單元)和聚合反應觸媒(特別是氧化還原引發劑)。
歐洲專利申請案EP 0 376 094描述一種形成凝膠的射出介質，其用以密封管線或建築物，或用以形成以丙烯酸或甲基丙烯酸的羥基烷酯和交聯用單體為基礎之水無法穿透的基層。此介質應含有至少2重量%之衍生自丙烯酸或甲基丙烯酸的三級胺，及過氧二硫酸鹽，形成引發劑系統。所提出之此交聯用的多烯系不飽和自由基可聚合的單體特別是聚乙二醇的二丙烯酸酯和二甲基丙烯酸酯，其必須儘可能地含有1－10個環氧乙烷單元，亦為所提及之聚乙二醇的伸甲基雙丙烯醯胺或甲基丙烯醯胺、丙烯醯胺甲醚和甲基丙烯醯胺甲醚。
日本專利申請案JP 02－206657使用液體混合物用於密封有缺陷的水密封，該液體混合物包含單體(例如，丙烯
醯胺、聚二甲基丙烯酸乙二醇酯或正－羥甲基丙醇)、吸水性聚合物樹脂和分散水的橡膠乳膠(例如，SBR、NBR、天然橡膠或氯丁二烯橡膠)。此液體混合物與反應觸媒反應，以提供所欲的水密封材料。
日本專利申請案JP 2003193032 A揭示一種以含水溶液為基礎的水密封組成物，其包含水溶性聚二(甲基)丙烯酸伸烷二醇酯、陰離子性電解質單體、具有二或更多個羥基的醇和聚合反應觸媒。聚二(甲基)丙烯酸伸烷二醇酯相對於陰離子性電解質單體的重量比必須在98：2至40：60的範圍內。以溶液總重計，此陰離子性電解質單體的比例為5－70重量%。
日本專利申請案JP 62－022882 A描述一種水密封組成物，其包含氧化還原聚合反應引發劑、具有2至50個重覆單元的聚二(甲基)丙烯酸乙二醇酯、特別量比例的陰離子性電解質單體和陽離子性電解質單體。
國際專利申請案WO 97/03151係關於一種潤滑劑，其包含可聚合的液態丙烯酸酯單體和過氧基聚合反應引發劑。較佳地，使用聚二甲基丙烯酸乙二醇酯作為可聚合的聚丙烯酸酯。
歐洲專利申請案EP 0 470 008 A1係關於以至少一種水可溶解或水可分散之不飽和羧酸的烷氧基烷酯為基礎之組成物。此組成物包含至少一種聚甲基丙烯酸或丙烯酸烷氧基甲氧基乙酯、至少一種引發劑(選自過硫酸鹼金屬鹽、過硫酸銨和過氧化氫)、至少一種聚合反應加速劑和水
。此組成物特別可用於地下(underground)密封。
DE 1974 86 31描述一般密封材料並在列表中亦提及，聚甲基丙烯酸乙二醇酯，但其亦為單官能性化合物。其中缺乏與化合物分子量有關的資訊。
DE 422 61 98描述水可膨脹的密封劑，其由甲基丙烯酸酯單體(例如，乙氧化的TMPTMA(此例中，MW＝1000，但無進一步數據))所組成；此混合物額外包含未共聚合的聚乙二醇酯。
專利申請案EP 1 616 906係關於由甲基丙烯酸酯單體形成之水可膨脹的密封劑；實例中，僅發現(甲基)丙烯酸，其經共擠壓。
就以前的技術觀之，本發明的目的係提供使得有缺陷的密封位置具較佳密封的方式。同時，密封材料必須特別具有改良的膨賬性和非常良好的機械性質。此外，此密封必須可以非常簡單和迅速的方式完成。最後，本發明的目的亦為達到非常有效和持久的密封。
藉由使用具有本申請專利範圍第1項之所有特徵的可膨脹聚合物，達到這些目的和未特別陳述但由引言所討論的關聯而無可避免的進一步目的。特別適當的程序述於關於申請專利範圍第1項的附屬項中。另受到保護者為用於有缺陷的密封位置之密封的方法。
藉由使用藉由使包含至少一種重均分子量大於2500克/莫耳的聚二(甲基)丙烯酸伸烷二醇酯之組成物聚合可得之可膨脹的聚合物，可以並非立即可預知的方式獲致有缺陷的密封位置之較佳密封。同時，此密封材料之特點在於改良的膨脹性、機械性(特別是抗張強度和破裂時的拉伸率)相對較佳。此外，此密封可以極簡單和相對迅速的方式達成，且其可獲致非常有效率和持久的密封。此外，根據本發明使用之聚合物在生態和健康方面皆無疑慮。
本發明之說明中，可膨脹的聚合物用於密封。此處，“可膨脹”是指在溶劑的作用下，聚合物改變其形狀和增加其體積。本發明目的上之較佳溶劑為在25℃測得之相對介電常數大於10的極性化合物，特別是水和具1至4個碳原子的醇類，特別佳者是水。適當地，可達到的膨脹率至少150%，特別是至少200%。
根據本發明使用之聚合物可藉由使包含至少一種重均分子量大於2500克/莫耳(以在2500至10,000克/莫耳的範圍內為佳，大於5000克/莫耳更佳，特別是大於8000克/莫耳)的聚二(甲基)丙烯酸伸烷二醇酯之組成物聚合而得。
分子量可以目前已知的方式藉凝膠滲透(GPC)或光散射測定。發現特別有用的方法為藉GPC測定。
此聚二(甲基)丙烯酸伸烷二醇酯以包含乙二醇單元和/或丙二醇單元為佳，以每一情況中之聚合物總重計，
這些單元的比例以至少50.0重量%為佳，適當地為至少75.0重量%，特別是至少90.0重量%。特別佳者係聚二(甲基)丙烯酸乙二醇酯單元。
此聚合物可視情況而定地具有其他共聚合單體單元。較佳地，聚合物可藉由與可共聚合的胺和/或羥烷酯共聚合而得。極佳之可共聚物的胺係式(I)的三級胺CH2
＝CR’－CO－X－(R”－O)n
－R”－NR2
(I)其中R是烷基、羥烷基或烷氧烷基，各者於烷基或烷氧基中具有1至4個碳原子，或者兩個R基團一起與氮原子形成雜環，R’是氫原子或甲基，X是氧原子或－NR－或－NH－基團，R”是具有2至4個碳原子的伸烷基，及n是0至4的整數。
此式所指的三級胺較佳為水溶性之丙烯酸和/或甲基丙烯酸之經取代的酯或醯胺。在丙烯酸衍生物的情況中，R’＝H；在甲基丙烯酸衍生物的情況中，R’＝CH3
。醯胺由於較高的水解安定性而優於酯類。較佳地，它們含有的X基團為NH。可用的R”基團是，例如，1,2－伸丙基、1,2－和1,4－伸丁基，以1,2－伸乙基和1,3－伸丙基為佳。通常，n＝0。在前式的酯類化合物中(即，X＝O時)，n以0至4為佳，特別是0至2。三級胺氮原子上的R基以具有1至4個碳原子的烷基或羥烷基為佳，特別是甲基。兩個R基團可以，與氮原子一起，較佳地，形成5－或6－員雜環，例
如，吡咯烷、哌啶或嗎啉環。
特別佳的三級胺為丙烯酸和甲基丙烯酸2－二甲胺基乙酯、丙烯酸和甲基丙烯酸3－(N,N－二甲胺基)丙酯、丙烯酸和甲基丙烯酸4－(N,N－二甲胺基)丁酯、3－(N,N－二甲胺基)丙基丙烯醯胺和－甲基丙烯醯胺、三乙醇胺單丙烯酸酯和單甲基丙烯酸酯、丙烯酸和甲基丙烯酸2－(二甲胺基乙氧基)乙酯、丙烯酸和甲基丙烯酸2－咪唑基乙酯、丙烯酸和甲基丙烯酸2－哌嗪基乙酯、2－哌嗪基乙基丙烯醯胺和甲基丙烯醯胺、丙烯酸和甲基丙烯酸N,N－二甲胺基新戊酯、N,N－二甲胺基新戊基丙烯醯胺和－甲基丙烯醯胺、丙烯酸和甲基丙烯酸(1,2,2,6,6－五甲基哌啶基－4)酯、3－嗎啉基丙基丙烯醯胺和－甲基丙烯醯胺、丙烯酸和甲基丙烯酸2－嗎啉基乙酯、丙烯酸和甲基丙烯酸2－(N,N－二丁胺基)乙酯、4－二乙胺基－1－甲基丁基丙烯醯胺和－甲基丙烯醯胺。
可使用之丙烯酸和/或甲基丙烯酸的羥烷酯特別是羥烷基中具有2至4個碳原子的水溶性酯類，如，丙烯酸和甲基丙烯酸羥乙酯、丙烯酸和甲基丙烯酸2－羥丙酯、丙烯酸和甲基丙烯酸2－或4－羥丁酯。結構CH2
＝CR－CO－O－(Alk－O)x
－H的羥基(聚烷氧基烷基)酯(其中R＝H或CH3
，Alk是具有2至4個碳原子的伸烷基，x是0至10的整數)亦適用。
較佳地，所用單體之水溶性使得它們於20℃共形成至少10重量%(以20重量%至60重量%為佳)的含水溶液
。由於在一些情況中，溶解的單體互相作為助溶劑，所以也可以使用或額外使用在單獨使用時不完全與水互溶的單體。但是，特別佳的單體是在－5℃至＋40℃的溫度範圍內，與水完全互溶的單體。
根據本發明之特別有利之可用的聚合物係藉由使包含分子量M至少等於2500克/莫耳(大於5000克/莫耳較佳)的聚二甲基丙烯酸乙二醇酯與至少一種其他的(甲基)丙烯酸單體(特別是(甲基)丙烯酸和胺基(甲基)丙烯酸)之組成物聚合而得者。
藉由將此聚合物施用於欲密封的位置，此聚合物可用於以目前已知方式密封之有缺陷的密封位置之密封。但特別有利的程序係包含至少一種重均分子量大於1200克/莫耳的聚二(甲基)丙烯酸伸烷二醇酯之組成物施用於有缺陷的密封位置並聚合。
此聚合反應以使用自由基形成用引發劑於0℃至100℃的溫度範圍內聚合為佳。
較佳地，此組成物藉由添加以組成物總重計為1重量%至7重量%的水溶性無機過氧基二硫酸鹽(如，過氧基二硫酸鹼金屬鹽或過氧基二硫酸銨)於高於0℃的溫度(以5℃至40℃為佳)，在短時間內形成軟性凝膠。硬化時間以20秒鐘至120秒鐘為佳，低於60秒鐘更佳。除了過氧基二硫酸鹽以外或代替過氧基二硫酸鹽，也可以使用有效量的其他水溶性自由基形成用引發劑(如，第三丁基過氧化氫)，只要它們能夠在低溫與三級胺形成氧化還原系
統即可。
由於即使於低溫亦非常迅速地固化，在添加引發劑之後，將此組成物運送至其必須固化成凝膠的使用位置時須特別小心。以使用低容量混合槽為佳，組成物和引發劑水溶液(以此為佳)加至此混合槽中，使得它們立刻充分混合並於之後直接到達施用位置。
此組成物的使用濃度應儘可能地使得自由基聚合反應直接形成具有所欲性質的凝膠。適當濃度是，例如，可聚合的化合物之10重量%至60重量%，以20重量%至40重量%為佳。
下文中，以實例和比較例進一步說明本發明，但無意以此對本發明之範圍造成任何限制。
0.20重量%(0.12克)的2,2’－偶氮基雙異丁腈(AIBN)49.9重量%(29.94克)的聚二甲基丙烯酸乙二醇酯29.94重量%(17.96克)丙烯酸19.96重量%(11.98克)的甲基丙烯酸2－二甲胺基乙酯
在玻璃板製的槽中，以平板槽法製得平板聚合物。使用的間隔器為4毫米圓繩。此聚合反應在60℃水浴中進行
7小時。移除上方玻璃板和圓繩之後，在強制通風乾燥箱中於100℃熱處理18小時。
欲測定機械性質，聚合物儲存於蒸餾水中三天。自膨脹狀態的聚合物平板打孔取得試樣。
自平板聚合物切下尺寸為20x15x4毫米的試樣。這些於真空乾燥箱中於100℃ 18小時以適應條件。冷卻至室溫之後，試樣經稱重並儲存在位於23℃之環境控制室中之蒸餾水(100毫升)中之透明玻璃瓶中的不銹鋼網上。於規則的時間間隔取出，以吸收紙吸收黏著性液體，聚合物片再度稱重。持續此測定直到達到最大膨脹率。
此結果顯示本發明之實例的膨脹率獲明顯提高。破裂時的拉伸率測試顯示明顯改良的值。反之，抗張強度略差
但於相仿程度(ISO 527－3/2/25，夾具長度25毫米)。
Claims (8)
- 一種可膨脹聚合物於密封上之用途，其特徵在於此聚合物可藉由使包含至少一種重均分子量大於5000克/莫耳的聚二(甲基)丙烯酸伸烷二醇酯之組成物聚合而得。
- 如申請專利範圍第1項之用途，其中聚二(甲基)丙烯酸伸烷二醇酯包含乙二醇單元和/或丙二醇單元。
- 如申請專利範圍第2項之用途，其中使用聚二(甲基)丙烯酸乙二醇酯。
- 如申請專利範圍第1至3項中任一項之用途，其中此聚合物可由使包含可與聚二(甲基)丙烯酸伸烷二醇酯共聚合的胺和/或羥烷酯之組成物共聚合而得。
- 如申請專利範圍第4項之用途，其中此聚合物可藉由與至少一種式(I)的三級胺共聚合而得，CH2 =CR’-CO-X-(R”-O)n -R”-NR2 (I)其中R是烷基、羥烷基或烷氧烷基，各者於烷基或烷氧基中具有1至4個碳原子，或者兩個R基團一起與氮原子形成雜環，R’是氫原子或甲基，X是氧原子或-NR-或-NH-基團，R”是具有2至4個碳原子的伸烷基，及n是0至4的整數。
- 如申請專利範圍第4項之用途，其中此聚合物可 藉由與至少一種丙烯酸和/或甲基丙烯酸的羥烷酯共聚合而得。
- 一種用於將有缺陷的密封位置密封的方法，包括將包含至少一種重均分子量大於5000克/莫耳的聚二(甲基)丙烯酸伸烷二醇酯之組成物施用於有缺陷的密封位置並聚合。
- 如申請專利範圍第7項之方法，其中該組成物係使用自由基形成用引發劑於0℃至100℃的溫度範圍內聚合。
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007032403A DE102007032403A1 (de) | 2007-07-10 | 2007-07-10 | Verwendung eines quellbaren Polymers zum Abdichten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200918652A TW200918652A (en) | 2009-05-01 |
| TWI494420B true TWI494420B (zh) | 2015-08-01 |
Family
ID=39743142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW097125590A TWI494420B (zh) | 2007-07-10 | 2008-07-07 | 可膨脹聚合物於密封上之用途 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8309669B2 (zh) |
| EP (1) | EP2164881B1 (zh) |
| JP (1) | JP5523315B2 (zh) |
| KR (1) | KR101546547B1 (zh) |
| CN (1) | CN101343527B (zh) |
| AT (1) | ATE522554T1 (zh) |
| AU (1) | AU2008274524B2 (zh) |
| BR (1) | BRPI0814045A2 (zh) |
| CA (1) | CA2693440C (zh) |
| DE (1) | DE102007032403A1 (zh) |
| ES (1) | ES2371301T3 (zh) |
| RU (1) | RU2496795C2 (zh) |
| TW (1) | TWI494420B (zh) |
| WO (1) | WO2009007154A1 (zh) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102702987B (zh) * | 2012-03-21 | 2015-02-18 | 北京京东方光电科技有限公司 | 封框胶组合物、防止液晶污染方法、液晶面板及显示装置 |
| EP2945994B1 (en) | 2013-01-18 | 2018-07-11 | Basf Se | Acrylic dispersion-based coating compositions |
| BR112017025558A2 (pt) | 2015-06-03 | 2018-08-07 | Sika Tech Ag | pré-polímeros terminados com vinil com baixa viscosidade e boa solubilidade em água |
| EP3344721B1 (de) | 2015-09-02 | 2019-11-06 | Sika Technology AG | Korrosionsinhibierende, radikalisch aushärtbare zusammensetzung |
| TWI875875B (zh) * | 2019-11-29 | 2025-03-11 | 日商力森諾科股份有限公司 | 含有具有聚氧化烯鏈之化合物之組成物套組 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6222882B2 (zh) * | 1983-12-29 | 1987-05-20 | Yokohama Rubber Co Ltd |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1907666A1 (de) * | 1969-02-15 | 1970-10-15 | Merck Patent Gmbh | Quellfaehige Polymerisate |
| JPS57119972A (en) * | 1981-01-19 | 1982-07-26 | Asahi Denka Kogyo Kk | Water-swelling, water-stopping material |
| JPS58206680A (ja) * | 1982-05-26 | 1983-12-01 | Mitsui Toatsu Chem Inc | 止水剤 |
| JPS61221281A (ja) * | 1985-03-27 | 1986-10-01 | Nitto Chem Ind Co Ltd | 止水剤 |
| JPS61231081A (ja) * | 1985-04-06 | 1986-10-15 | Mitsui Toatsu Chem Inc | 止水剤 |
| JPH0623380B2 (ja) | 1985-07-24 | 1994-03-30 | 日東化学工業株式会社 | 止水剤 |
| JPS6234977A (ja) * | 1985-08-08 | 1987-02-14 | Mitsui Toatsu Chem Inc | 止水剤 |
| JPS62129376A (ja) | 1985-12-02 | 1987-06-11 | Toagosei Chem Ind Co Ltd | 漏水管の補修方法 |
| DE3843440A1 (de) | 1988-12-23 | 1990-06-28 | Roehm Gmbh | Gelbildendes injektionsmittel |
| JPH02206657A (ja) | 1989-02-03 | 1990-08-16 | Showa Electric Wire & Cable Co Ltd | 止水材料 |
| JPH02302488A (ja) * | 1989-05-18 | 1990-12-14 | Teijin Chem Ltd | 防曇性組成物 |
| FR2665164B1 (fr) | 1990-07-30 | 1994-05-06 | Rhone Poulenc Chimie | Compositions aqueuses polymerisables a base d'un ester d'alcoxyalkyle et preparation dudit ester d'alcoxyalkyle. |
| DE4103969A1 (de) * | 1991-02-09 | 1992-08-13 | Basf Ag | Verfahren zur herstellung von feinteiligen, wasserloeslichen oder wasserquellbaren polymerisaten |
| RU2036947C1 (ru) * | 1991-12-28 | 1995-06-09 | Государственный научно-исследовательский институт химии и технологии полимеров им.акад.В.А.Каргина с опытным заводом | Анаэробная герметизирующая композиция |
| DE4226198A1 (de) * | 1992-05-08 | 1993-11-11 | Betonbau Zubehoer Handel | Dichtungsmaterial |
| WO1997003151A1 (en) | 1993-09-27 | 1997-01-30 | Vincent Larry W | Compressible graphite lubricant and anaerobic pipe sealant |
| JPH08283697A (ja) * | 1995-04-11 | 1996-10-29 | Nippon Shokubai Co Ltd | 光ケーブル用止水剤および複合止水材 |
| JP3621210B2 (ja) * | 1996-10-09 | 2005-02-16 | 三菱レイヨン株式会社 | 止水用薬液及びそれを用いた止水工法 |
| DE19748631A1 (de) * | 1997-11-04 | 1999-05-06 | Fraunhofer Ges Forschung | Sicherheitsabdichtung für flüssige Systeme unter Einsatz von quellfähigen Polymeren |
| JP3970604B2 (ja) | 2001-12-26 | 2007-09-05 | 三菱レイヨン株式会社 | 止水剤および止水工法 |
| DE102004032694A1 (de) * | 2004-07-06 | 2006-02-02 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Quellfähige Materialzusammensetzung und deren Verwendung |
| JP4916695B2 (ja) * | 2005-10-05 | 2012-04-18 | 吉佳株式会社 | 止水剤組成物 |
-
2007
- 2007-07-10 DE DE102007032403A patent/DE102007032403A1/de not_active Withdrawn
-
2008
- 2008-05-09 KR KR1020107000460A patent/KR101546547B1/ko active Active
- 2008-05-09 US US12/663,709 patent/US8309669B2/en active Active
- 2008-05-09 ES ES08750216T patent/ES2371301T3/es active Active
- 2008-05-09 RU RU2010104102/04A patent/RU2496795C2/ru not_active IP Right Cessation
- 2008-05-09 JP JP2010515434A patent/JP5523315B2/ja active Active
- 2008-05-09 AU AU2008274524A patent/AU2008274524B2/en not_active Ceased
- 2008-05-09 WO PCT/EP2008/055725 patent/WO2009007154A1/de not_active Ceased
- 2008-05-09 EP EP08750216A patent/EP2164881B1/de active Active
- 2008-05-09 CA CA2693440A patent/CA2693440C/en not_active Expired - Fee Related
- 2008-05-09 AT AT08750216T patent/ATE522554T1/de active
- 2008-05-09 BR BRPI0814045-6A2A patent/BRPI0814045A2/pt not_active IP Right Cessation
- 2008-07-07 TW TW097125590A patent/TWI494420B/zh not_active IP Right Cessation
- 2008-07-09 CN CN2008101356569A patent/CN101343527B/zh active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6222882B2 (zh) * | 1983-12-29 | 1987-05-20 | Yokohama Rubber Co Ltd |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20100043181A (ko) | 2010-04-28 |
| US8309669B2 (en) | 2012-11-13 |
| TW200918652A (en) | 2009-05-01 |
| JP5523315B2 (ja) | 2014-06-18 |
| JP2010532806A (ja) | 2010-10-14 |
| RU2010104102A (ru) | 2011-08-20 |
| BRPI0814045A2 (pt) | 2015-02-10 |
| HK1125965A1 (zh) | 2009-08-21 |
| CN101343527A (zh) | 2009-01-14 |
| CN101343527B (zh) | 2013-04-17 |
| CA2693440A1 (en) | 2009-01-15 |
| ES2371301T3 (es) | 2011-12-29 |
| ATE522554T1 (de) | 2011-09-15 |
| KR101546547B1 (ko) | 2015-08-21 |
| WO2009007154A1 (de) | 2009-01-15 |
| EP2164881A1 (de) | 2010-03-24 |
| EP2164881B1 (de) | 2011-08-31 |
| CA2693440C (en) | 2015-11-17 |
| DE102007032403A1 (de) | 2009-01-22 |
| US20100163177A1 (en) | 2010-07-01 |
| AU2008274524B2 (en) | 2013-09-12 |
| RU2496795C2 (ru) | 2013-10-27 |
| AU2008274524A1 (en) | 2009-01-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Hao et al. | Mechanical behavior of hybrid hydrogels composed of a physical and a chemical network | |
| TWI494420B (zh) | 可膨脹聚合物於密封上之用途 | |
| JP5556174B2 (ja) | ハイドロゲルおよびその製造方法 | |
| RU2013134327A (ru) | Вспененная клейкая лента для наклеивания на неполярные поверхности | |
| JP2019085521A (ja) | ポリビニルアルコール系相互貫入型ゲル | |
| WO2021058122A1 (en) | Method for producing a polymeric composition and polymeric composition thus produced as well as applications thereof, especially as or in pressure-sensitive adhesives | |
| JP2009057508A (ja) | 水性エマルション接着剤 | |
| CN108912288B (zh) | 一种高熔融指数的热塑性弹性体及其制备方法 | |
| JP2019203065A (ja) | 有機無機複合ヒドロゲル前駆体組成物、及び有機無機複合ヒドロゲル | |
| JP5544719B2 (ja) | ゲルおよびその製造方法 | |
| JP2590006B2 (ja) | 塗膜防水用組成物 | |
| JP6713224B2 (ja) | コンクリート構造体用充填材のための分散液、コンクリート構造体用充填材の製造方法、及びコンクリート構造体の製造方法 | |
| HK1125965B (zh) | 可溶胀的聚合物用於密封的用途 | |
| CN119219829B (zh) | 高耐热柔性石墨双极板微孔堵漏剂 | |
| JPH1150046A (ja) | シーリング材組成物 | |
| JP2709710B2 (ja) | ラジカル硬化性水溶性重合体 | |
| Shams Es-haghi | Mechanics of Tough Chemically Cross-linked Hydrogels | |
| JP2024175854A (ja) | （メタ）アクリル系グラフト共重合体、樹脂組成物、粘着剤、及び粘着シート | |
| JP2024090619A (ja) | 組成物、粘着剤組成物、粘着剤、及び粘着シート | |
| CN115461417A (zh) | 具有改进的低温柔韧性的膨胀型涂层 | |
| JP2001354829A (ja) | 水系樹脂組成物及びこれを用いた水系コーティング剤 | |
| JP2002053845A (ja) | 密着性の良好な止水材、止水工法用鋼矢板およびそれらを利用した止水工法 | |
| JP2001348409A (ja) | 水系樹脂組成物及びこれを用いた水系コーティング剤 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |