ES2625878T3 - Copolímero soluble en agua o desintegrable en agua - Google Patents
Copolímero soluble en agua o desintegrable en agua Download PDFInfo
- Publication number
- ES2625878T3 ES2625878T3 ES10189433.5T ES10189433T ES2625878T3 ES 2625878 T3 ES2625878 T3 ES 2625878T3 ES 10189433 T ES10189433 T ES 10189433T ES 2625878 T3 ES2625878 T3 ES 2625878T3
- Authority
- ES
- Spain
- Prior art keywords
- copolymer
- weight
- shock resistance
- acrylic acid
- ester
- 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.)
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 174
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title description 34
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 37
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 36
- 150000002148 esters Chemical class 0.000 claims abstract description 16
- 238000005227 gel permeation chromatography Methods 0.000 claims abstract description 9
- 239000003607 modifier Substances 0.000 claims description 46
- 230000035939 shock Effects 0.000 claims description 46
- 229920000642 polymer Polymers 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 19
- -1 alkyl alkoxy ester Chemical class 0.000 claims description 18
- 230000009477 glass transition Effects 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 9
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 7
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 6
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 6
- 230000007935 neutral effect Effects 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 4
- 230000004927 fusion Effects 0.000 claims description 4
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 3
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 3
- YXYJVFYWCLAXHO-UHFFFAOYSA-N 2-methoxyethyl 2-methylprop-2-enoate Chemical compound COCCOC(=O)C(C)=C YXYJVFYWCLAXHO-UHFFFAOYSA-N 0.000 claims description 2
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims 2
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000002763 monocarboxylic acids Chemical class 0.000 abstract 1
- 229920001897 terpolymer Polymers 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- 230000008901 benefit Effects 0.000 description 13
- 239000000178 monomer Substances 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 125000003700 epoxy group Chemical group 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 229920002125 Sokalan® Polymers 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 229920001169 thermoplastic Polymers 0.000 description 5
- 239000004416 thermosoftening plastic Substances 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- XEBWQGVWTUSTLN-UHFFFAOYSA-M phenylmercury acetate Chemical compound CC(=O)O[Hg]C1=CC=CC=C1 XEBWQGVWTUSTLN-UHFFFAOYSA-M 0.000 description 4
- 229920000774 poly(2-methoxyaniline-5-sulfonic acid) polymer Polymers 0.000 description 4
- 229920000058 polyacrylate Polymers 0.000 description 4
- 239000004584 polyacrylic acid Substances 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- 238000010146 3D printing Methods 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 125000005250 alkyl acrylate group Chemical group 0.000 description 3
- 150000008064 anhydrides Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229920003169 water-soluble polymer Polymers 0.000 description 3
- FWWXYLGCHHIKNY-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate Chemical compound CCOCCOC(=O)C=C FWWXYLGCHHIKNY-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 2
- 229920002873 Polyethylenimine Polymers 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- FACXGONDLDSNOE-UHFFFAOYSA-N buta-1,3-diene;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 FACXGONDLDSNOE-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000005553 drilling Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229920005615 natural polymer Polymers 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229920006132 styrene block copolymer Polymers 0.000 description 2
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 2
- 229920001059 synthetic polymer Polymers 0.000 description 2
- IAXXETNIOYFMLW-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) 2-methylprop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C(=C)C)CC1C2(C)C IAXXETNIOYFMLW-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical group C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- PEXNXOXCZLFQAO-ODZAUARKSA-N (z)-but-2-enedioic acid;ethenyl acetate Chemical compound CC(=O)OC=C.OC(=O)\C=C/C(O)=O PEXNXOXCZLFQAO-ODZAUARKSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- VXASQTMYWZHWMX-UHFFFAOYSA-N 4-ethoxybutyl 2-methylprop-2-enoate Chemical compound CCOCCCCOC(=O)C(C)=C VXASQTMYWZHWMX-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 238000003723 Smelting Methods 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 150000001253 acrylic acids Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- NBZANZVJRKXVBH-GYDPHNCVSA-N alpha-Cryptoxanthin Natural products O[C@H]1CC(C)(C)C(/C=C/C(=C\C=C\C(=C/C=C/C=C(\C=C\C=C(/C=C/[C@H]2C(C)=CCCC2(C)C)\C)/C)\C)/C)=C(C)C1 NBZANZVJRKXVBH-GYDPHNCVSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- WJAKXPUSJAKPHH-UHFFFAOYSA-N buta-1,3-diene;ethene;styrene Chemical compound C=C.C=CC=C.C=CC1=CC=CC=C1 WJAKXPUSJAKPHH-UHFFFAOYSA-N 0.000 description 1
- WWNGFHNQODFIEX-UHFFFAOYSA-N buta-1,3-diene;methyl 2-methylprop-2-enoate;styrene Chemical compound C=CC=C.COC(=O)C(C)=C.C=CC1=CC=CC=C1 WWNGFHNQODFIEX-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000011960 computer-aided design Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000000551 dentifrice Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- DZZVFJCQWKGPNY-UHFFFAOYSA-N ethyl 2-methylprop-2-eneperoxoate Chemical compound CCOOC(=O)C(C)=C DZZVFJCQWKGPNY-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000003676 hair preparation Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N hexanedioic acid Natural products OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid group Chemical group C(\C=C/C(=O)O)(=O)O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical group O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical group 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 210000000633 nuclear envelope Anatomy 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002432 poly(vinyl methyl ether) polymer Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000867 polyelectrolyte Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QROGIFZRVHSFLM-UHFFFAOYSA-N prop-1-enylbenzene Chemical class CC=CC1=CC=CC=C1 QROGIFZRVHSFLM-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- 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
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/02—Homopolymers or copolymers of acids; Metal 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
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
-
- 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
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10189433.5A EP2447292B1 (de) | 2010-10-29 | 2010-10-29 | Wasserlösliches bzw. in wasser desintegrierbares copolymer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2625878T3 true ES2625878T3 (es) | 2017-07-20 |
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| ES10189433.5T Active ES2625878T3 (es) | 2010-10-29 | 2010-10-29 | Copolímero soluble en agua o desintegrable en agua |
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| EP (1) | EP2447292B1 (OSRAM) |
| JP (2) | JP2013540874A (OSRAM) |
| CN (2) | CN106883339B (OSRAM) |
| ES (1) | ES2625878T3 (OSRAM) |
| TW (1) | TW201229066A (OSRAM) |
| WO (1) | WO2012055972A1 (OSRAM) |
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| ES2625878T3 (es) * | 2010-10-29 | 2017-07-20 | Bellandtechnology Ag | Copolímero soluble en agua o desintegrable en agua |
| WO2014076519A1 (fr) | 2012-10-29 | 2014-05-22 | Debiotech S.A. | Dispositif de traitement extra corporel du sang |
| GB201317626D0 (en) * | 2013-10-04 | 2013-11-20 | Schlumberger Holdings | Solids in borehole fluids |
| EP3107735B1 (de) * | 2014-02-20 | 2018-05-02 | Gallus Ferd. Rüesch AG | Siebdruckschablone und verfahren zu deren bebilderung |
| JP2016013658A (ja) * | 2014-07-02 | 2016-01-28 | セイコーエプソン株式会社 | 三次元造形物の製造方法、三次元造形物および三次元造形用組成物 |
| JP6491467B2 (ja) | 2014-10-14 | 2019-03-27 | 花王株式会社 | 三次元造形用可溶性材料 |
| JP5972335B2 (ja) | 2014-10-14 | 2016-08-17 | 花王株式会社 | 三次元造形用可溶性材料 |
| WO2016106062A1 (en) | 2014-12-23 | 2016-06-30 | Bridgestone Americas Tire Operations, Llc | Actinic radiation curable polymeric mixtures, cured polymeric mixtures and related processes |
| EP3251818B1 (en) * | 2015-01-26 | 2019-12-11 | KJ Chemicals Corporation | Active energy ray-curable resin composition for three-dimensional model supporting material |
| KR102064816B1 (ko) | 2015-06-19 | 2020-01-10 | 스트래터시스,인코포레이티드 | 적층 제조에 사용되는 수계 분산형 중합체 |
| WO2017020020A1 (en) * | 2015-07-30 | 2017-02-02 | Wildcat Dp Llc | Material and method for 3-d fabrication |
| US11097531B2 (en) | 2015-12-17 | 2021-08-24 | Bridgestone Americas Tire Operations, Llc | Additive manufacturing cartridges and processes for producing cured polymeric products by additive manufacturing |
| WO2018081053A1 (en) | 2016-10-27 | 2018-05-03 | Bridgestone Americas Tire Operations, Llc | Processes for producing cured polymeric products by additive manufacturing |
| US11220062B2 (en) | 2017-10-10 | 2022-01-11 | Stratasys, Inc. | Water-dispersible thermoplastic material comprising sulfonated copolymer for use in additive manufacturing |
| FR3074181B1 (fr) | 2017-11-28 | 2020-11-06 | Arkema France | Composition copolymerique hydrosoluble a ph neutre |
| JP2021507957A (ja) * | 2017-12-22 | 2021-02-25 | ディーエスエム アイピー アセッツ ビー．ブイ．Ｄｓｍ Ｉｐ Ａｓｓｅｔｓ Ｂ．Ｖ． | 接着剤組成物及び３ｄ印刷におけるその使用 |
| WO2020077127A1 (en) | 2018-10-10 | 2020-04-16 | Stratasys, Inc. | Water dispersible sulfonated thermoplastic copolymer for use in additive manufacturing |
| FR3088327B1 (fr) | 2018-11-08 | 2021-11-05 | Arkema France | Composition copolymerique hydrosoluble |
| CN111574655B (zh) * | 2020-06-08 | 2022-05-20 | 中国石油化工股份有限公司 | 一种水溶崩解型投球笼及其制备方法 |
| US12157800B2 (en) | 2021-04-12 | 2024-12-03 | Stratasys, Inc. | Method for underwater processing of water-dispersible materials |
Family Cites Families (25)
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| GB833571A (en) * | 1956-03-22 | 1960-04-27 | Monsanto Chemicals | Interpolymers and interpolymerisation processes employing the same |
| US4196272A (en) * | 1978-11-27 | 1980-04-01 | Nalco Chemical Company | Continuous process for the preparation of an acrylic acid-methyl acrylate copolymer in a tubular reactor |
| JPS6131333A (ja) * | 1984-07-20 | 1986-02-13 | 花王株式会社 | セメント混和剤 |
| US4711725A (en) * | 1985-06-26 | 1987-12-08 | Rohm And Haas Co. | Method of stabilizing aqueous systems |
| JPH0713115B2 (ja) * | 1986-12-02 | 1995-02-15 | ライオン株式会社 | 水溶性ポリマ− |
| DE3818425A1 (de) * | 1988-05-31 | 1989-12-07 | Basf Ag | Verwendung von wasserloeslichen polymerisaten als klebstoff |
| CN1154375A (zh) * | 1995-10-27 | 1997-07-16 | 罗姆和哈斯公司 | 用于自动洗碗洗涤剂的聚羧酸盐 |
| CA2240711C (en) * | 1995-12-22 | 2003-09-16 | Janice E. Losasso | Low molecular weight structured polymers |
| US6013421A (en) * | 1996-07-19 | 2000-01-11 | Fuji Photo Film Co., Ltd. | Silver halide photographic light-sensitive material and image-forming method |
| DE19639347A1 (de) | 1996-09-25 | 1998-03-26 | Belland Ag | Zweiphasige, in wäßrigem Alkali auflösbare Polymerkombination und Verfahren zu ihrer Herstellung |
| JP3031327B2 (ja) | 1998-03-26 | 2000-04-10 | 日本電気株式会社 | スペクトラム拡散通信システムおよびその過負荷制御方法 |
| US7754807B2 (en) * | 1999-04-20 | 2010-07-13 | Stratasys, Inc. | Soluble material and process for three-dimensional modeling |
| JP3648704B2 (ja) * | 2000-02-14 | 2005-05-18 | タムラ化研株式会社 | 活性エネルギー線硬化性組成物及びプリント配線板 |
| US6890989B2 (en) * | 2001-03-12 | 2005-05-10 | Kimberly-Clark Worldwide, Inc. | Water-responsive biodegradable polymer compositions and method of making same |
| JP2007241071A (ja) * | 2006-03-10 | 2007-09-20 | Fujifilm Corp | 反射透過型液晶表示装置 |
| JP2008101201A (ja) * | 2006-09-20 | 2008-05-01 | Toray Ind Inc | カルボキシル基含有アクリル共重合体の製造方法 |
| JP5157251B2 (ja) * | 2007-05-21 | 2013-03-06 | 東亞合成株式会社 | 炭酸カルシウム用分散剤 |
| JP2009191089A (ja) * | 2008-02-12 | 2009-08-27 | Toray Ind Inc | 熱可塑性樹脂組成物、その製造方法および成形品 |
| JP5417600B2 (ja) * | 2008-02-15 | 2014-02-19 | 大塚化学株式会社 | 水性顔料分散体及びコーティング剤 |
| US8876513B2 (en) * | 2008-04-25 | 2014-11-04 | 3D Systems, Inc. | Selective deposition modeling using CW UV LED curing |
| FR2937149B1 (fr) * | 2008-10-13 | 2010-12-03 | Commissariat Energie Atomique | Dispositif de mesure en ligne d'un flux de neutrons rapides et epithermiques |
| US8246888B2 (en) | 2008-10-17 | 2012-08-21 | Stratasys, Inc. | Support material for digital manufacturing systems |
| CN102458633A (zh) | 2009-06-11 | 2012-05-16 | 东亚合成株式会社 | 颜料用分散剂及其用途 |
| EA025196B1 (ru) * | 2010-07-21 | 2016-11-30 | Басф Се | Способ получения ароматических соединений из метана |
| ES2625878T3 (es) * | 2010-10-29 | 2017-07-20 | Bellandtechnology Ag | Copolímero soluble en agua o desintegrable en agua |
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2010
- 2010-10-29 ES ES10189433.5T patent/ES2625878T3/es active Active
- 2010-10-29 EP EP10189433.5A patent/EP2447292B1/de active Active
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2011
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- 2011-10-27 CN CN201180051582.0A patent/CN103314022B/zh active Active
- 2011-10-27 WO PCT/EP2011/068879 patent/WO2012055972A1/de not_active Ceased
- 2011-10-27 JP JP2013535441A patent/JP2013540874A/ja active Pending
- 2011-10-28 TW TW100139491A patent/TW201229066A/zh unknown
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Also Published As
| Publication number | Publication date |
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| US20130225779A1 (en) | 2013-08-29 |
| JP6343598B2 (ja) | 2018-06-13 |
| US9399691B2 (en) | 2016-07-26 |
| US20160297910A1 (en) | 2016-10-13 |
| CN106883339B (zh) | 2019-07-23 |
| EP2447292A1 (de) | 2012-05-02 |
| JP2016135589A (ja) | 2016-07-28 |
| CN103314022B (zh) | 2016-11-09 |
| TW201229066A (en) | 2012-07-16 |
| US20180022847A1 (en) | 2018-01-25 |
| US10308743B2 (en) | 2019-06-04 |
| EP2447292B1 (de) | 2017-03-29 |
| WO2012055972A1 (de) | 2012-05-03 |
| JP2013540874A (ja) | 2013-11-07 |
| CN103314022A (zh) | 2013-09-18 |
| US9777090B2 (en) | 2017-10-03 |
| CN106883339A (zh) | 2017-06-23 |
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