CA1143499A - Photopolymerized hydrophilic interpolymers of unsaturated carboxylic acid and esters - Google Patents
Photopolymerized hydrophilic interpolymers of unsaturated carboxylic acid and estersInfo
- Publication number
- CA1143499A CA1143499A CA000335929A CA335929A CA1143499A CA 1143499 A CA1143499 A CA 1143499A CA 000335929 A CA000335929 A CA 000335929A CA 335929 A CA335929 A CA 335929A CA 1143499 A CA1143499 A CA 1143499A
- Authority
- CA
- Canada
- Prior art keywords
- weight percent
- interpolymer
- methacrylate
- percent
- acrylate
- 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.)
- Expired
Links
- 150000002148 esters Chemical class 0.000 title claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
- 239000000835 fiber Substances 0.000 claims abstract description 19
- 239000002250 absorbent Substances 0.000 claims abstract description 15
- 230000002745 absorbent Effects 0.000 claims abstract description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 14
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims abstract description 9
- 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 8
- 125000005250 alkyl acrylate group Chemical group 0.000 claims abstract description 7
- 239000000178 monomer Substances 0.000 claims description 38
- -1 acrylic ester Chemical class 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 25
- 229920000642 polymer Polymers 0.000 claims description 22
- 239000002270 dispersing agent Substances 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 12
- 150000001408 amides Chemical class 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical group COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 150000001340 alkali metals Chemical class 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 5
- 239000012965 benzophenone Substances 0.000 claims description 5
- 239000003431 cross linking reagent Substances 0.000 claims description 5
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical group C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 claims description 4
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- XOALFFJGWSCQEO-UHFFFAOYSA-N tridecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C=C XOALFFJGWSCQEO-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 229940048053 acrylate Drugs 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
- 210000001124 body fluid Anatomy 0.000 claims 1
- 239000010839 body fluid Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 12
- 238000002360 preparation method Methods 0.000 abstract description 4
- 150000003839 salts Chemical class 0.000 abstract description 3
- 229940063557 methacrylate Drugs 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 1
- 239000010408 film Substances 0.000 description 26
- 229920001577 copolymer Polymers 0.000 description 17
- 239000012530 fluid Substances 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 6
- 150000002334 glycols Chemical class 0.000 description 6
- 210000002700 urine Anatomy 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000008719 thickening Effects 0.000 description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- SWFHGTMLYIBPPA-UHFFFAOYSA-N (4-methoxyphenyl)-phenylmethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 SWFHGTMLYIBPPA-UHFFFAOYSA-N 0.000 description 2
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- VZMLJEYQUZKERO-UHFFFAOYSA-N 2-hydroxy-1-(2-methylphenyl)-2-phenylethanone Chemical compound CC1=CC=CC=C1C(=O)C(O)C1=CC=CC=C1 VZMLJEYQUZKERO-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920001131 Pulp (paper) Polymers 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000012669 compression test Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 229940086559 methyl benzoin Drugs 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- OJLABXSUFRIXFL-UHFFFAOYSA-N (2-benzoylphenyl)-phenylmethanone Chemical compound C=1C=CC=C(C(=O)C=2C=CC=CC=2)C=1C(=O)C1=CC=CC=C1 OJLABXSUFRIXFL-UHFFFAOYSA-N 0.000 description 1
- CKGKXGQVRVAKEA-UHFFFAOYSA-N (2-methylphenyl)-phenylmethanone Chemical compound CC1=CC=CC=C1C(=O)C1=CC=CC=C1 CKGKXGQVRVAKEA-UHFFFAOYSA-N 0.000 description 1
- QRWAIZJYJNLOPG-UHFFFAOYSA-N (2-oxo-1,2-diphenylethyl) acetate Chemical compound C=1C=CC=CC=1C(OC(=O)C)C(=O)C1=CC=CC=C1 QRWAIZJYJNLOPG-UHFFFAOYSA-N 0.000 description 1
- MSMAPCFQRXQMRL-UHFFFAOYSA-N (2-oxo-1,2-diphenylethyl) prop-2-enoate Chemical compound C=1C=CC=CC=1C(OC(=O)C=C)C(=O)C1=CC=CC=C1 MSMAPCFQRXQMRL-UHFFFAOYSA-N 0.000 description 1
- CPLWKNRPZVNELG-UHFFFAOYSA-N (3-chlorophenyl)-phenylmethanone Chemical compound ClC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 CPLWKNRPZVNELG-UHFFFAOYSA-N 0.000 description 1
- VMFJVWPCRCAWBS-UHFFFAOYSA-N (3-methoxyphenyl)-phenylmethanone Chemical compound COC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 VMFJVWPCRCAWBS-UHFFFAOYSA-N 0.000 description 1
- URBLVRAVOIVZFJ-UHFFFAOYSA-N (3-methylphenyl)-phenylmethanone Chemical compound CC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 URBLVRAVOIVZFJ-UHFFFAOYSA-N 0.000 description 1
- OZDCBKYPNBVRSA-UHFFFAOYSA-N (4,4-dimethoxycyclohexa-1,5-dien-1-yl)-phenylmethanone Chemical compound C1=CC(OC)(OC)CC=C1C(=O)C1=CC=CC=C1 OZDCBKYPNBVRSA-UHFFFAOYSA-N 0.000 description 1
- ZRIPJJWYODJTLH-UHFFFAOYSA-N (4-benzylphenyl)-(4-chlorophenyl)methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C(C=C1)=CC=C1CC1=CC=CC=C1 ZRIPJJWYODJTLH-UHFFFAOYSA-N 0.000 description 1
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- PIMNFNXBTGPCIL-UHFFFAOYSA-N 1-(2-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=CC=C1Br PIMNFNXBTGPCIL-UHFFFAOYSA-N 0.000 description 1
- UWMVGWBKNREGBO-UHFFFAOYSA-N 1-(2-methylpropyl)naphthalene;sodium Chemical compound [Na].C1=CC=C2C(CC(C)C)=CC=CC2=C1 UWMVGWBKNREGBO-UHFFFAOYSA-N 0.000 description 1
- JYAQYXOVOHJRCS-UHFFFAOYSA-N 1-(3-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(Br)=C1 JYAQYXOVOHJRCS-UHFFFAOYSA-N 0.000 description 1
- BAYUSCHCCGXLAY-UHFFFAOYSA-N 1-(3-methoxyphenyl)ethanone Chemical compound COC1=CC=CC(C(C)=O)=C1 BAYUSCHCCGXLAY-UHFFFAOYSA-N 0.000 description 1
- SKBBQSLSGRSQAJ-UHFFFAOYSA-N 1-(4-acetylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(C(C)=O)C=C1 SKBBQSLSGRSQAJ-UHFFFAOYSA-N 0.000 description 1
- WYECURVXVYPVAT-UHFFFAOYSA-N 1-(4-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Br)C=C1 WYECURVXVYPVAT-UHFFFAOYSA-N 0.000 description 1
- HDMHXSCNTJQYOS-UHFFFAOYSA-N 1-(4-prop-2-enylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(CC=C)C=C1 HDMHXSCNTJQYOS-UHFFFAOYSA-N 0.000 description 1
- ZIAQIHPONXZRSW-UHFFFAOYSA-N 1-(bromomethyl)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2CBr ZIAQIHPONXZRSW-UHFFFAOYSA-N 0.000 description 1
- MQAPIKRRBOTIMD-UHFFFAOYSA-N 1-(chloromethyl)benzo[b]phenalen-7-one Chemical compound ClCC1=CC=C2C=CC=C3C(=O)C4=CC=CC=C4C1=C23 MQAPIKRRBOTIMD-UHFFFAOYSA-N 0.000 description 1
- XMWGTKZEDLCVIG-UHFFFAOYSA-N 1-(chloromethyl)naphthalene Chemical compound C1=CC=C2C(CCl)=CC=CC2=C1 XMWGTKZEDLCVIG-UHFFFAOYSA-N 0.000 description 1
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- GXGACIKXINYLAR-UHFFFAOYSA-N 2,2-dibutoxy-1-phenylethanone Chemical compound CCCCOC(OCCCC)C(=O)C1=CC=CC=C1 GXGACIKXINYLAR-UHFFFAOYSA-N 0.000 description 1
- LNBMZFHIYRDKNS-UHFFFAOYSA-N 2,2-dimethoxy-1-phenylethanone Chemical compound COC(OC)C(=O)C1=CC=CC=C1 LNBMZFHIYRDKNS-UHFFFAOYSA-N 0.000 description 1
- ZWNMRZQYWRLGMM-UHFFFAOYSA-N 2,5-dimethylhexane-2,5-diol Chemical compound CC(C)(O)CCC(C)(C)O ZWNMRZQYWRLGMM-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- RFIMISVNSAUMBU-UHFFFAOYSA-N 2-(hydroxymethyl)-2-(prop-2-enoxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC=C RFIMISVNSAUMBU-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- COBPKKZHLDDMTB-UHFFFAOYSA-N 2-[2-(2-butoxyethoxy)ethoxy]ethanol Chemical compound CCCCOCCOCCOCCO COBPKKZHLDDMTB-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 description 1
- GTAKOUPXIUWZIA-UHFFFAOYSA-N 2-[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]ethanol Chemical compound CCOCCOCCOCCOCCO GTAKOUPXIUWZIA-UHFFFAOYSA-N 0.000 description 1
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 1
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- 239000010409 thin film Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- JVYCFGPPVMLAAL-UHFFFAOYSA-N triacontyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCOC(=O)C=C JVYCFGPPVMLAAL-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/60—Liquid-swellable gel-forming materials, e.g. super-absorbents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/923—Ethylenic monomers containing at least one salt group
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dispersion Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Hematology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Absorbent Articles And Supports Therefor (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/951,906 US4167464A (en) | 1978-10-16 | 1978-10-16 | Photopolymerized hydrophilic interpolymers of unsaturated carboxylic acid and esters |
| US951,906 | 1992-09-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1143499A true CA1143499A (en) | 1983-03-22 |
Family
ID=25492307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000335929A Expired CA1143499A (en) | 1978-10-16 | 1979-09-19 | Photopolymerized hydrophilic interpolymers of unsaturated carboxylic acid and esters |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4167464A (https=) |
| EP (1) | EP0020529B1 (https=) |
| JP (1) | JPH0245643B2 (https=) |
| BE (1) | BE879256A (https=) |
| CA (1) | CA1143499A (https=) |
| DE (1) | DE2964823D1 (https=) |
| DK (1) | DK160881C (https=) |
| ES (1) | ES485070A0 (https=) |
| IE (1) | IE49730B1 (https=) |
| IT (1) | IT1193244B (https=) |
| MX (1) | MX153748A (https=) |
| WO (1) | WO1980000844A1 (https=) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4267103A (en) * | 1978-12-07 | 1981-05-12 | The B. F. Goodrich Company | Solvent polymerization of carboxyl containing monomers |
| BR8008821A (pt) * | 1979-09-11 | 1981-06-23 | Goodrich Co B F | Interpolimeros hidrofilos fotopolimerizados de acidos e esteres carboxilicos insaturados |
| EP0042406B1 (en) * | 1979-12-26 | 1985-06-19 | The B.F. GOODRICH Company | Photopolymerized hydrophilic filmsor fibers of acrylic acid and polyfunctional cross-linking agents |
| EP0055728A4 (en) * | 1980-07-08 | 1982-08-11 | Goodrich Co B F | HYDROPHILIC INTERPOLYMERS OF ACRYLIC ACIDS AND AN ACRYLATE. |
| US4486489A (en) * | 1980-07-08 | 1984-12-04 | The B. F. Goodrich Company | Films of hydrophilic interpolymers of neutralized acrylic acid, hydroxyalkyl methacrylate or dialkylaminoalkyl (meth)acrylate and optionally a cross-linking agent |
| GR75761B (https=) * | 1980-09-02 | 1984-08-02 | Goodrich Co B F | |
| DE3101892A1 (de) * | 1981-01-22 | 1982-08-26 | Röhm GmbH, 6100 Darmstadt | Verfahren zur herstellung von waessrigen kunststoffdispersionen mit hohem pigmentbindevermoegen |
| AU7328581A (en) * | 1981-03-16 | 1982-10-06 | Hwa, S.C.P. | Novel protein curd product and process of preparation |
| DE3239476C2 (de) * | 1981-10-26 | 1984-06-20 | Arakawa Kagaku Kogyo K.K., Osaka | Verfahren zur Herstellung eines festen, trockenen und wasserabsorbierenden harzes |
| US4466993A (en) * | 1983-02-07 | 1984-08-21 | The B. F. Goodrich Company | Preparation of film of web-reinforced photopolymerized hydrophilic interpolymer |
| US4519883A (en) * | 1983-06-06 | 1985-05-28 | Stauffer Chemical Company | Sensitization of glyoxylate photoinitiators using a terphenyl compound |
| JPS6121104A (ja) * | 1984-07-10 | 1986-01-29 | Adeka Argus Chem Co Ltd | 光重合開始剤 |
| EP0214089B1 (en) * | 1985-07-22 | 1990-05-09 | Prutec Limited | A photo-hardenable composition for bioactive coatings |
| DE3545250A1 (de) * | 1985-12-20 | 1987-06-25 | Stockhausen Chem Fab Gmbh | Verfahren zur herstellung von mit wasser quellbaren, wasserunloeslichen synthesefasern und ihre verwendung als absorptionsmaterial |
| CA1326416C (en) * | 1986-08-25 | 1994-01-25 | Ralph Xavier Ewall | Polymeric wound dressings |
| NO880552L (no) * | 1987-08-25 | 1989-02-27 | Goodrich Co B F | Saarbandasje basert paa polymermateriale. |
| US4914170A (en) * | 1987-11-17 | 1990-04-03 | Rohm And Haas Company | Superabsorbent polymeric compositions and process for producing the same |
| FR2623516B1 (fr) * | 1987-11-19 | 1994-04-15 | Saint Gobain Vitrage | Composition pour revetement antibuee, produit revetu de cette composition et procede de preparation de ce produit |
| US5035892A (en) * | 1988-05-09 | 1991-07-30 | Dow Corning Corporation | Antimicrobial superabsorbent compositions and methods |
| US4990338A (en) * | 1988-05-09 | 1991-02-05 | Dow Corning Corporation | Antimicrobial superabsorbent compositions and methods |
| US5241009A (en) * | 1990-05-07 | 1993-08-31 | Kimberly-Clark Corporation | Polymeric composition containing carboxy nueutralized with lithium or potassium |
| JPH06220336A (ja) * | 1992-12-04 | 1994-08-09 | W R Grace & Co | 安定なプラスチゾル |
| JPH06240155A (ja) * | 1992-12-22 | 1994-08-30 | W R Grace & Co | 耐熱性に優れたフィルムを与える安定なプラスチゾル |
| CA2114815C (en) * | 1993-02-24 | 2005-06-14 | Mark Kevin Melius | Absorbent composite |
| US5358611A (en) * | 1993-05-17 | 1994-10-25 | Rohm And Haas Company | Method of reducing impurities in aqueous monomer solutions |
| US5674917A (en) * | 1995-03-30 | 1997-10-07 | Woodbridge Foam Corporation | Superabsorbent hydrophilic isocyanate-based foam and process for production thereof |
| US5719201A (en) * | 1995-03-30 | 1998-02-17 | Woodbridge Foam Corporation | Superabsorbent hydrophilic isocyanate-based foam and process for production thereof |
| IL118372A0 (en) * | 1995-05-23 | 1996-09-12 | Kobe Steel Ltd | Water-blocking composite and its preparation |
| US5744509A (en) * | 1996-07-01 | 1998-04-28 | Woodbridge Foam Corporation | Foamed polymer and process for production thereof |
| US5624971A (en) * | 1996-07-01 | 1997-04-29 | Woodbridge Foam Corporation | Foamed polymer and process for production thereof |
| US5817703A (en) * | 1996-09-30 | 1998-10-06 | Woodbridge Foam Corporation | Rebond foam and process for production thereof |
| US6649099B2 (en) | 1998-10-30 | 2003-11-18 | Kimberly-Clark Worldwide, Inc. | Method of incorporating fluid treatment agents into absorbent composites |
| US6350711B1 (en) | 1998-10-30 | 2002-02-26 | Kimberly-Clark Worldwide, Inc. | Absorbent article with fluid treatment agent |
| US6867344B2 (en) * | 1998-10-30 | 2005-03-15 | Kimberly-Clark Worldwide, Inc. | Absorbent article with fluid treatment agent |
| GB0013839D0 (en) | 2000-06-07 | 2000-07-26 | Ciba Spec Chem Water Treat Ltd | Water swellable compositions |
| GB0013845D0 (en) * | 2000-06-07 | 2000-07-26 | Campbell Dussek Ltd | A cable or cable component coated with a water swellable material |
| US6403674B1 (en) | 2000-11-17 | 2002-06-11 | Eveready Battery Company, Inc. | Solvent-free method for synthesizing superabsorbent polymers |
| EP1537260B1 (en) * | 2002-09-13 | 2009-11-04 | Cerex Advanced Fabrics, Inc. | Method of reducing static in a spunbond process |
| US7838610B2 (en) * | 2005-09-30 | 2010-11-23 | Nippon Shokubai Co., Ltd. | Ion-sensitive super-absorbent polymer |
| CN102405063B (zh) | 2009-02-18 | 2015-12-09 | 奎克-麦德技术公司 | 含有过氧化物的超吸收材料 |
| US9580639B2 (en) * | 2011-07-18 | 2017-02-28 | Saudi Arabian Oil Company | Controlled release of surfactants for enhanced oil recovery |
| US12128144B2 (en) | 2018-04-02 | 2024-10-29 | Polygreen Ltd | Process for the production of biodegradable superabsorbent polymer with high absorbency under load based on styrene maleic acid copolymers and biopolymer |
| CN112512470B (zh) | 2018-04-02 | 2023-05-05 | 聚合物绿色有限责任公司 | 用于处理非织造网的液体聚合物溶液 |
| WO2020102227A1 (en) | 2018-11-13 | 2020-05-22 | Green Polymers Ltd. | Polymeric composition for use as soil conditioner with improved water absorbency during watering of the agricultural crops |
| CN112679667B (zh) * | 2020-12-09 | 2022-08-02 | 沧州师范学院 | 一种含有硅氧烷基团的柔性高分子针头及其制备方法和应用 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2064729A5 (https=) * | 1969-10-22 | 1971-07-23 | Progil | |
| IL36796A (en) * | 1970-05-13 | 1974-12-31 | Hydrophilics Int Inc | Hydrophilic acrylic copolymers and viscosity control agent and film made therefrom |
| US4069124A (en) * | 1971-07-29 | 1978-01-17 | Ceskoslovenska Akademie Ved | Method for controlled radiation polymerization of olefinic monomers |
| US3948740A (en) * | 1973-05-04 | 1976-04-06 | Hercules Incorporated | Polymerization of water soluble monomers with radiation and chemical initiator |
| CH606154A5 (https=) * | 1974-07-02 | 1978-11-15 | Goodrich Co B F | |
| US3966573A (en) * | 1974-10-31 | 1976-06-29 | Sun Chemical Corporation | Photopolymerization co-initiator systems |
| JPS5539170B2 (https=) * | 1975-01-16 | 1980-10-08 | ||
| US4190562A (en) * | 1977-04-04 | 1980-02-26 | The B. F. Goodrich Company | Improved water absorbent copolymers of copolymerizable carboxylic acids and acrylic or methacrylic esters |
| US4062817A (en) * | 1977-04-04 | 1977-12-13 | The B.F. Goodrich Company | Water absorbent polymers comprising unsaturated carboxylic acid, acrylic ester containing alkyl group 10-30 carbon atoms, and another acrylic ester containing alkyl group 2-8 carbon atoms |
| US4066583A (en) * | 1977-05-16 | 1978-01-03 | The B. F. Goodrich Company | Flexible water absorbent polymer compositions comprising (a) unsaturated carboxylic acid, acrylic ester containing alkyl group 10-30 carbon atoms, additional monomer plus (b) aliphatic diol |
-
1978
- 1978-10-16 US US05/951,906 patent/US4167464A/en not_active Expired - Lifetime
-
1979
- 1979-09-14 DE DE7979901403T patent/DE2964823D1/de not_active Expired
- 1979-09-14 WO PCT/US1979/000728 patent/WO1980000844A1/en not_active Ceased
- 1979-09-14 JP JP54501800A patent/JPH0245643B2/ja not_active Expired - Lifetime
- 1979-09-19 CA CA000335929A patent/CA1143499A/en not_active Expired
- 1979-10-08 BE BE0/197519A patent/BE879256A/fr not_active IP Right Cessation
- 1979-10-11 MX MX179639A patent/MX153748A/es unknown
- 1979-10-12 IT IT26487/79A patent/IT1193244B/it active
- 1979-10-15 IE IE1955/79A patent/IE49730B1/en unknown
- 1979-10-16 ES ES485070A patent/ES485070A0/es active Granted
-
1980
- 1980-05-07 EP EP79901403A patent/EP0020529B1/en not_active Expired
- 1980-06-13 DK DK255680A patent/DK160881C/da active
Also Published As
| Publication number | Publication date |
|---|---|
| DE2964823D1 (en) | 1983-03-24 |
| IE791955L (en) | 1980-04-16 |
| IE49730B1 (en) | 1985-12-11 |
| JPH0245643B2 (https=) | 1990-10-11 |
| US4167464A (en) | 1979-09-11 |
| DK160881C (da) | 1991-10-14 |
| IT7926487A0 (it) | 1979-10-12 |
| EP0020529A1 (en) | 1981-01-07 |
| DK255680A (da) | 1980-06-13 |
| BE879256A (fr) | 1980-02-01 |
| ES8100312A1 (es) | 1980-11-01 |
| EP0020529B1 (en) | 1983-02-16 |
| WO1980000844A1 (en) | 1980-05-01 |
| IT1193244B (it) | 1988-06-15 |
| EP0020529A4 (en) | 1981-01-23 |
| ES485070A0 (es) | 1980-11-01 |
| DK160881B (da) | 1991-04-29 |
| JPS55500802A (https=) | 1980-10-16 |
| MX153748A (es) | 1986-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |