RU2714313C2 - Полимер с высвобождаемым газом - Google Patents
Полимер с высвобождаемым газом Download PDFInfo
- Publication number
- RU2714313C2 RU2714313C2 RU2017106175A RU2017106175A RU2714313C2 RU 2714313 C2 RU2714313 C2 RU 2714313C2 RU 2017106175 A RU2017106175 A RU 2017106175A RU 2017106175 A RU2017106175 A RU 2017106175A RU 2714313 C2 RU2714313 C2 RU 2714313C2
- Authority
- RU
- Russia
- Prior art keywords
- polymerization
- polymer
- reaction mixture
- less
- compound
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 75
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims abstract description 58
- 239000000203 mixture Substances 0.000 claims abstract description 32
- 239000002245 particle Substances 0.000 claims abstract description 23
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 7
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 38
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 30
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical group C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 14
- 125000000524 functional group Chemical class 0.000 claims description 6
- 238000005342 ion exchange Methods 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001302 tertiary amino group Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 37
- 239000000126 substance Substances 0.000 abstract description 11
- 239000011347 resin Substances 0.000 abstract description 4
- 229920005989 resin Polymers 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 129
- 238000006116 polymerization reaction Methods 0.000 description 96
- 150000001875 compounds Chemical class 0.000 description 85
- 239000011541 reaction mixture Substances 0.000 description 82
- 239000000178 monomer Substances 0.000 description 69
- 239000003112 inhibitor Substances 0.000 description 52
- 230000002401 inhibitory effect Effects 0.000 description 36
- 238000010526 radical polymerization reaction Methods 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 32
- 229920002554 vinyl polymer Polymers 0.000 description 31
- 239000004615 ingredient Substances 0.000 description 30
- 239000002253 acid Substances 0.000 description 26
- 230000000052 comparative effect Effects 0.000 description 25
- 239000003999 initiator Substances 0.000 description 25
- 230000008859 change Effects 0.000 description 20
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 17
- 239000000872 buffer Substances 0.000 description 16
- 150000002826 nitrites Chemical class 0.000 description 16
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 14
- 239000002243 precursor Substances 0.000 description 14
- 150000003254 radicals Chemical class 0.000 description 14
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 10
- 239000004327 boric acid Substances 0.000 description 10
- 229920002451 polyvinyl alcohol Polymers 0.000 description 10
- 108010010803 Gelatin Proteins 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 229920000159 gelatin Polymers 0.000 description 9
- 239000008273 gelatin Substances 0.000 description 9
- 235000019322 gelatine Nutrition 0.000 description 9
- 235000011852 gelatine desserts Nutrition 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000004342 Benzoyl peroxide Substances 0.000 description 8
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- 235000019400 benzoyl peroxide Nutrition 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000004949 mass spectrometry Methods 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- 235000010288 sodium nitrite Nutrition 0.000 description 8
- 239000004372 Polyvinyl alcohol Substances 0.000 description 7
- 239000012736 aqueous medium Substances 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000012634 fragment Substances 0.000 description 7
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 7
- 229920003169 water-soluble polymer Polymers 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 6
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 6
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 6
- RZQXOGQSPBYUKH-UHFFFAOYSA-N 3-[[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]azaniumyl]-2-hydroxypropane-1-sulfonate Chemical compound OCC(CO)(CO)NCC(O)CS(O)(=O)=O RZQXOGQSPBYUKH-UHFFFAOYSA-N 0.000 description 5
- RINWGRJHXCCLOV-UHFFFAOYSA-N BPO Chemical compound BPO RINWGRJHXCCLOV-UHFFFAOYSA-N 0.000 description 5
- OWXMKDGYPWMGEB-UHFFFAOYSA-N HEPPS Chemical compound OCCN1CCN(CCCS(O)(=O)=O)CC1 OWXMKDGYPWMGEB-UHFFFAOYSA-N 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 230000003139 buffering effect Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- XCBLFURAFHFFJF-UHFFFAOYSA-N 3-[bis(2-hydroxyethyl)azaniumyl]-2-hydroxypropane-1-sulfonate Chemical compound OCCN(CCO)CC(O)CS(O)(=O)=O XCBLFURAFHFFJF-UHFFFAOYSA-N 0.000 description 3
- RZBCCAZHJQZKLL-UHFFFAOYSA-N 5-methoxy-12-methyl-11h-indolo[2,3-a]carbazole-6-carbonitrile Chemical compound N1C2=C3N(C)C4=CC=C[CH]C4=C3C(OC)=C(C#N)C2=C2[C]1C=CC=C2 RZBCCAZHJQZKLL-UHFFFAOYSA-N 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 150000007514 bases Chemical class 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical class [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 3
- 239000008241 heterogeneous mixture Substances 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229940005654 nitrite ion Drugs 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- YNLCVAQJIKOXER-UHFFFAOYSA-N N-[tris(hydroxymethyl)methyl]-3-aminopropanesulfonic acid Chemical compound OCC(CO)(CO)NCCCS(O)(=O)=O YNLCVAQJIKOXER-UHFFFAOYSA-N 0.000 description 2
- JOCBASBOOFNAJA-UHFFFAOYSA-N N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid Chemical compound OCC(CO)(CO)NCCS(O)(=O)=O JOCBASBOOFNAJA-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000006172 buffering agent Substances 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- -1 carboxymethyl methyl Chemical group 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- YMAWOPBAYDPSLA-UHFFFAOYSA-N glycylglycine Chemical compound [NH3+]CC(=O)NCC([O-])=O YMAWOPBAYDPSLA-UHFFFAOYSA-N 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 238000010979 pH adjustment Methods 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- LVQFQZZGTZFUNF-UHFFFAOYSA-N 2-hydroxy-3-[4-(2-hydroxy-3-sulfonatopropyl)piperazine-1,4-diium-1-yl]propane-1-sulfonate Chemical compound OS(=O)(=O)CC(O)CN1CCN(CC(O)CS(O)(=O)=O)CC1 LVQFQZZGTZFUNF-UHFFFAOYSA-N 0.000 description 1
- HRGUSFBJBOKSML-UHFFFAOYSA-N 3',5'-di-O-methyltricetin Chemical compound COC1=C(O)C(OC)=CC(C=2OC3=CC(O)=CC(O)=C3C(=O)C=2)=C1 HRGUSFBJBOKSML-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 108700016232 Arg(2)-Sar(4)- dermorphin (1-4) Proteins 0.000 description 1
- 108010008488 Glycylglycine Proteins 0.000 description 1
- 239000007996 HEPPS buffer Substances 0.000 description 1
- GIZQLVPDAOBAFN-UHFFFAOYSA-N HEPPSO Chemical compound OCCN1CCN(CC(O)CS(O)(=O)=O)CC1 GIZQLVPDAOBAFN-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-O Htris Chemical compound OCC([NH3+])(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-O 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
- IDDMFNIRSJVBHE-UHFFFAOYSA-N Piscigenin Natural products COC1=C(O)C(OC)=CC(C=2C(C3=C(O)C=C(O)C=C3OC=2)=O)=C1 IDDMFNIRSJVBHE-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 208000034953 Twin anemia-polycythemia sequence Diseases 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 239000012928 buffer substance Substances 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 1
- 235000005487 catechin Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- 229950001002 cianidanol Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- KCFYHBSOLOXZIF-UHFFFAOYSA-N dihydrochrysin Natural products COC1=C(O)C(OC)=CC(C2OC3=CC(O)=CC(O)=C3C(=O)C2)=C1 KCFYHBSOLOXZIF-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229940043257 glycylglycine Drugs 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229960004337 hydroquinone Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000013028 medium composition Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- BMCJATLPEJCACU-UHFFFAOYSA-N tricin Natural products COc1cc(OC)c(O)c(c1)C2=CC(=O)c3c(O)cc(O)cc3O2 BMCJATLPEJCACU-UHFFFAOYSA-N 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/16—Organic material
- B01J39/18—Macromolecular compounds
- B01J39/20—Macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
-
- 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
- C08F112/00—Homopolymers 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 an aromatic carbocyclic ring
- C08F112/02—Monomers containing only one unsaturated aliphatic radical
- C08F112/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F112/06—Hydrocarbons
- C08F112/08—Styrene
-
- 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
- C08F12/00—Homopolymers and 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 an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/06—Hydrocarbons
- C08F12/08—Styrene
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
- C08F2/42—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation using short-stopping agents
-
- 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
- C08F212/00—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 an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/04—Homopolymers or copolymers of styrene
-
- 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
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Polymerisation Methods In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Graft Or Block Polymers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462037337P | 2014-08-14 | 2014-08-14 | |
| US62/037,337 | 2014-08-14 | ||
| PCT/US2015/044766 WO2016025550A1 (en) | 2014-08-14 | 2015-08-12 | Polymer with releasable gas |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| RU2017106175A RU2017106175A (ru) | 2018-08-27 |
| RU2017106175A3 RU2017106175A3 (enExample) | 2019-02-11 |
| RU2714313C2 true RU2714313C2 (ru) | 2020-02-14 |
Family
ID=53901173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2017106175A RU2714313C2 (ru) | 2014-08-14 | 2015-08-12 | Полимер с высвобождаемым газом |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10221257B2 (enExample) |
| EP (1) | EP3180366B1 (enExample) |
| JP (1) | JP6723985B2 (enExample) |
| KR (1) | KR102427467B1 (enExample) |
| CN (1) | CN106574005B (enExample) |
| RU (1) | RU2714313C2 (enExample) |
| WO (1) | WO2016025550A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111278874B (zh) * | 2017-09-29 | 2023-12-22 | 罗门哈斯公司 | 制备具有径向变化的颗粒 |
| KR102621431B1 (ko) | 2017-09-29 | 2024-01-08 | 다우 글로벌 테크놀로지스 엘엘씨 | 반경방향 편차를 갖는 입자 |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1178751A1 (ru) * | 1984-05-10 | 1985-09-15 | Черкасское Отделение Научно-Исследовательского Института Пластических Масс | Способ получени сополимеров стирола с дивинилбензолом |
| US5994444A (en) * | 1997-10-16 | 1999-11-30 | Medtronic, Inc. | Polymeric material that releases nitric oxide |
| WO2007053578A2 (en) * | 2005-10-31 | 2007-05-10 | Amulet Pharmaceuticals, Inc. | Multi-phasic nitric oxide and drug co-eluting stent coatings |
| US20070196327A1 (en) * | 2005-12-06 | 2007-08-23 | Amulet Pharmaceuticals, Inc. | Nitric oxide releasing polymers |
| EP2119459A1 (en) * | 2005-02-11 | 2009-11-18 | NOLabs AB | Treatment of neuropathy involving nitric oxide |
| US20100255062A1 (en) * | 2007-06-01 | 2010-10-07 | Amulet Pharmaceuticals, Inc. | Compounds, polymers and methods for treating gastrointestinal dysfunction |
| US20120034169A1 (en) * | 2005-05-27 | 2012-02-09 | The University Of North Carolina At Chapel Hill | Nitric oxide-releasing particles for nitric oxide therapeutics and biomedical applications |
| US20140056957A1 (en) * | 2012-08-23 | 2014-02-27 | Nioxx Llc | Extended production of nitric oxide from microencapsulated chemical reactants |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1059698A (en) | 1974-09-30 | 1979-07-31 | B.F. Goodrich Company (The) | Controlling the mass polymerization of vinyl chloride monomer |
| US4070419A (en) * | 1975-12-01 | 1978-01-24 | Cosden Technology, Inc. | Polymerization of styrene |
| US4444960A (en) | 1980-06-30 | 1984-04-24 | Occidental Chemical Corporation | Polymer blends with improved hydrolytic stability |
| CA1166413A (en) | 1980-10-30 | 1984-05-01 | Edward E. Timm | Process and apparatus for preparing uniform size polymer beads |
| US4623706A (en) | 1984-08-23 | 1986-11-18 | The Dow Chemical Company | Process for preparing uniformly sized polymer particles by suspension polymerization of vibratorily excited monomers in a gaseous or liquid stream |
| US6323249B1 (en) | 1988-09-26 | 2001-11-27 | Purolite International, Ltd. | Macroporous resins having large pores but with high crush strength |
| US5405919A (en) * | 1992-08-24 | 1995-04-11 | The United States Of America As Represented By The Secretary Of Health And Human Services | Polymer-bound nitric oxide/nucleophile adduct compositions, pharmaceutical compositions and methods of treating biological disorders |
| US5650447A (en) * | 1992-08-24 | 1997-07-22 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Nitric oxide-releasing polymers to treat restenosis and related disorders |
| CA2106105C (en) * | 1993-09-14 | 2008-03-18 | Larry K. Keefer | Polymer-bound nitric oxide/nucleophile adduct compositions, pharmaceutical compositions incorporating same and methods of treating biological disorders using same |
| BE1007648A3 (fr) | 1993-10-21 | 1995-09-05 | Solvay | Procede pour la polymerisation radicalaire du chlorure de vinyle a ph acide en dispersion aqueuse. |
| DE69708896T2 (de) | 1996-09-25 | 2002-06-20 | Akzo Nobel N.V., Arnheim/Arnhem | Nitroso verbindungen zur pseudo-lebenden radikalpolymerisation |
| CN1210237C (zh) | 1998-03-03 | 2005-07-13 | 日本瑞翁公司 | 聚合防止性组合物,聚合防止剂和防止聚合的方法 |
| EP1236742A1 (en) | 2001-02-28 | 2002-09-04 | Bayer Ag | Controlled free-radical polymerization products using new control agents |
| DE10122896A1 (de) | 2001-05-11 | 2002-11-14 | Bayer Ag | Verfahren zur Herstellung von monodispersen gelförmigen Kationenaustauschern |
| US6703046B2 (en) * | 2001-10-04 | 2004-03-09 | Medtronic Ave Inc. | Highly cross-linked, extremely hydrophobic nitric oxide-releasing polymers and methods for their manufacture and use |
| JP2004250630A (ja) | 2003-02-21 | 2004-09-09 | Mitsubishi Chemicals Corp | 疎水性液滴の製造方法、ポリマービーズの製造方法及び製造装置、並びにイオン交換樹脂の製造方法 |
| DE102004006116A1 (de) | 2004-02-06 | 2005-08-25 | Bayer Chemicals Ag | Verfahren zur Herstellung von monodispersen porenhaltigen Ionenaustauschern |
| WO2005081752A2 (en) * | 2004-02-09 | 2005-09-09 | Amulet Pharmaceuticals, Inc. | Nitric oxide-releasing polymers |
| AU2005289414B2 (en) * | 2004-09-27 | 2010-12-09 | Government Of The United States Of America, Represented By The Secretary Department Of Health And Human Services | Nitric oxide-releasing diazeniumdiolated acrylonitrile-based polymers, and compositions, medical devices, and uses thereof |
| JP4815844B2 (ja) | 2005-04-04 | 2011-11-16 | 東洋インキＳｃホールディングス株式会社 | マイクロカプセルの製造方法 |
| EP1790335A1 (en) * | 2005-11-14 | 2007-05-30 | NOLabs AB | Composition and its use for the manufacture of a medicament for treating, prophylactically treating, preventing cancer and/or infections in the urinary tract |
| EP2154161B1 (en) | 2007-04-16 | 2012-01-04 | Kuraray Co., Ltd. | Dispersion stabilizer for suspension polymerization |
| CA2599082A1 (en) * | 2007-08-27 | 2009-02-27 | Ping I. Lee | Supramacromolecular polymer complexes providing controlled nitric oxide release for healing wounds |
| US20090232868A1 (en) * | 2008-03-17 | 2009-09-17 | Medtronic Vascular, Inc. | Nitric Oxide Releasing Polymer Composition |
| CA2671595A1 (en) * | 2009-07-09 | 2011-01-09 | Ping I. Lee | Controlled nitric oxide delivery from aqueous s-nitrosothiol conjugated polymers and their complexes |
| CA2879843C (en) * | 2012-07-17 | 2021-05-04 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Nitric oxide-releasing diazeniumdiolated polyvinylpyrrolidone-based polymers, and compositions, medical devices, and uses thereof |
| WO2016025549A1 (en) * | 2014-08-14 | 2016-02-18 | Rohm And Haas Company | Polymerization process |
-
2015
- 2015-08-12 CN CN201580043038.XA patent/CN106574005B/zh active Active
- 2015-08-12 EP EP15753580.8A patent/EP3180366B1/en active Active
- 2015-08-12 KR KR1020177005471A patent/KR102427467B1/ko active Active
- 2015-08-12 JP JP2017507830A patent/JP6723985B2/ja active Active
- 2015-08-12 US US15/503,516 patent/US10221257B2/en active Active
- 2015-08-12 RU RU2017106175A patent/RU2714313C2/ru active
- 2015-08-12 WO PCT/US2015/044766 patent/WO2016025550A1/en not_active Ceased
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1178751A1 (ru) * | 1984-05-10 | 1985-09-15 | Черкасское Отделение Научно-Исследовательского Института Пластических Масс | Способ получени сополимеров стирола с дивинилбензолом |
| US5994444A (en) * | 1997-10-16 | 1999-11-30 | Medtronic, Inc. | Polymeric material that releases nitric oxide |
| EP2119459A1 (en) * | 2005-02-11 | 2009-11-18 | NOLabs AB | Treatment of neuropathy involving nitric oxide |
| US20120034169A1 (en) * | 2005-05-27 | 2012-02-09 | The University Of North Carolina At Chapel Hill | Nitric oxide-releasing particles for nitric oxide therapeutics and biomedical applications |
| WO2007053578A2 (en) * | 2005-10-31 | 2007-05-10 | Amulet Pharmaceuticals, Inc. | Multi-phasic nitric oxide and drug co-eluting stent coatings |
| US20070196327A1 (en) * | 2005-12-06 | 2007-08-23 | Amulet Pharmaceuticals, Inc. | Nitric oxide releasing polymers |
| US20100255062A1 (en) * | 2007-06-01 | 2010-10-07 | Amulet Pharmaceuticals, Inc. | Compounds, polymers and methods for treating gastrointestinal dysfunction |
| US20140056957A1 (en) * | 2012-08-23 | 2014-02-27 | Nioxx Llc | Extended production of nitric oxide from microencapsulated chemical reactants |
Non-Patent Citations (1)
| Title |
|---|
| Amedea B. Seabra and Nelson Duran "Nitric oxide-releasing vehicle for biomedical applications" J. Mater. Chem., 2010, 20, pp.1624-1637. * |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2017106175A3 (enExample) | 2019-02-11 |
| KR102427467B1 (ko) | 2022-07-29 |
| US20170226239A1 (en) | 2017-08-10 |
| US10221257B2 (en) | 2019-03-05 |
| CN106574005B (zh) | 2020-07-21 |
| CN106574005A (zh) | 2017-04-19 |
| EP3180366A1 (en) | 2017-06-21 |
| JP2017524058A (ja) | 2017-08-24 |
| JP6723985B2 (ja) | 2020-07-15 |
| EP3180366B1 (en) | 2018-09-26 |
| WO2016025550A1 (en) | 2016-02-18 |
| KR20170042616A (ko) | 2017-04-19 |
| RU2017106175A (ru) | 2018-08-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6770948B2 (ja) | 重合プロセス | |
| JP4067405B2 (ja) | 安定化されたフォトクロミックラテックスを得る方法、該方法で得られたラテックスおよび該ラテックスの眼鏡レンズにおける使用 | |
| KR20160101976A (ko) | 다이비닐벤젠/말레산 무수물 중합체 재료 | |
| JP2017501279A (ja) | 加水分解ジビニルベンゼン／無水マレイン酸ポリマー材料 | |
| JP2004514181A (ja) | フォトクロミックラテックスを得る方法 | |
| CN106574005B (zh) | 具有可释放气体的聚合物 | |
| JP4922486B2 (ja) | 重合反応中の非常に速い開始剤の連続的配量 | |
| WO2001096424A1 (en) | Process for producing high-purity vinylpyrrolidone polymer | |
| KR101147877B1 (ko) | (코)폴리머를 제조하기 위한 중합 방법 | |
| JPS61141712A (ja) | Ｎ−ビニルカルボン酸アミド重合体の製造法 | |
| JP3986114B2 (ja) | ホスホモリブデン酸を用いる有機系ペルオキサイドの安定化 | |
| EP3130614B1 (en) | Method for producing vinyl-amine-unit-containing polymer, and polymerization product | |
| US5084498A (en) | Process for stabilizing copolymers of ethylenically unsaturated fluoro compounds with vinyl ethers | |
| EP3045479B1 (en) | Method for producing powdered n-vinylcarboxamide polymer composition and polyvinylamine aqueous solution | |
| US6025443A (en) | Process for the production of spherical polymers | |
| TWI794195B (zh) | 具有促進劑及抗氧化劑之樹脂 | |
| JPH0959305A (ja) | アクリル系重合体粒子の製造方法 | |
| JP2015067633A (ja) | 新規架橋重合体 | |
| RU2265617C2 (ru) | Малоразветвленный высокомолекулярный поливинилацетат, способ его получения и поливиниловый спирт на его основе | |
| JPH0627126B2 (ja) | 新規重合方法 | |
| JPH11349773A (ja) | アクリルアミド系重合体の安定化方法 |