CA1209524A - Copolymere hydrophile de l'acide acrylique et d'un acrylate - Google Patents

Copolymere hydrophile de l'acide acrylique et d'un acrylate

Info

Publication number: CA1209524A
Authority: CA; Canada
Prior art keywords: film; weight percent; acrylate; comonomer; methacrylate
Prior art date: 1980-07-08
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

Application number

CA000379531A

Other languages

English (en)

Inventor

Paul J. George

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Noveon IP Holdings Corp

Original Assignee

BF Goodrich Corp

Priority date (The priority date 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 date listed.)

1980-07-08

Filing date

1981-06-11

Publication date

1986-08-12

1981-06-11 Application filed by BF Goodrich Corp filed Critical BF Goodrich Corp

1986-08-12 Application granted granted Critical

1986-08-12 Publication of CA1209524A publication Critical patent/CA1209524A/fr

Status Expired legal-status Critical Current

Links

NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 10
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 title claims abstract description 9
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title description 8
239000000178 monomer Substances 0.000 claims abstract description 44
239000000203 mixture Substances 0.000 claims abstract description 26
-1 phenoxyalkyl acrylate Chemical compound 0.000 claims abstract description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
238000006116 polymerization reaction Methods 0.000 claims abstract description 15
239000002250 absorbent Substances 0.000 claims abstract description 12
230000002745 absorbent Effects 0.000 claims abstract description 12
125000000217 alkyl group Chemical group 0.000 claims abstract description 12
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims abstract description 9
239000003431 cross linking reagent Substances 0.000 claims description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 claims description 4
239000002585 base Substances 0.000 claims description 4
DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 3
239000002202 Polyethylene glycol Substances 0.000 claims description 3
229910021529 ammonia Inorganic materials 0.000 claims description 3
ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 3
125000004386 diacrylate group Chemical group 0.000 claims description 3
STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 3
229920001223 polyethylene glycol Polymers 0.000 claims description 3
KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 claims description 2
VDYWHVQKENANGY-UHFFFAOYSA-N 1,3-Butyleneglycol dimethacrylate Chemical compound CC(=C)C(=O)OC(C)CCOC(=O)C(C)=C VDYWHVQKENANGY-UHFFFAOYSA-N 0.000 claims description 2
SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 claims description 2
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 2
DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical group CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 claims description 2
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 2
244000028419 Styrax benzoin Species 0.000 claims description 2
235000000126 Styrax benzoin Nutrition 0.000 claims description 2
235000008411 Sumatra benzointree Nutrition 0.000 claims description 2
OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 claims description 2
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
229960002130 benzoin Drugs 0.000 claims description 2
239000012965 benzophenone Substances 0.000 claims description 2
VVYDVQWJZWRVPE-UHFFFAOYSA-L dimethyltin(2+);diiodide Chemical compound C[Sn](C)(I)I VVYDVQWJZWRVPE-UHFFFAOYSA-L 0.000 claims description 2
229940052303 ethers for general anesthesia Drugs 0.000 claims description 2
235000019382 gum benzoic Nutrition 0.000 claims description 2
ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 2
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 claims 1
AAMTXHVZOHPPQR-UHFFFAOYSA-N 2-(hydroxymethyl)prop-2-enoic acid Chemical group OCC(=C)C(O)=O AAMTXHVZOHPPQR-UHFFFAOYSA-N 0.000 claims 1
150000008366 benzophenones Chemical class 0.000 claims 1
FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 claims 1
229920000642 polymer Polymers 0.000 abstract description 26
230000005855 radiation Effects 0.000 abstract description 14
239000011953 free-radical catalyst Substances 0.000 abstract description 2
OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 abstract 1
WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 abstract 1
230000000379 polymerizing effect Effects 0.000 abstract 1
239000000835 fiber Substances 0.000 description 12
239000002270 dispersing agent Substances 0.000 description 11
239000000463 material Substances 0.000 description 10
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 9
229940048053 acrylate Drugs 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 9
229920001577 copolymer Polymers 0.000 description 9
239000007788 liquid Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000012530 fluid Substances 0.000 description 8
229940063557 methacrylate Drugs 0.000 description 8
238000000034 method Methods 0.000 description 8
150000001408 amides Chemical class 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
229910052783 alkali metal Inorganic materials 0.000 description 6
150000001340 alkali metals Chemical class 0.000 description 6
125000005250 alkyl acrylate group Chemical group 0.000 description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Substances [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
150000003863 ammonium salts Chemical class 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000002904 solvent Substances 0.000 description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
238000012669 compression test Methods 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000003999 initiator Substances 0.000 description 3
150000002825 nitriles Chemical class 0.000 description 3
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-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
BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 2
VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 2
KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-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
FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
XWCDCDSDNJVCLO-UHFFFAOYSA-N Chlorofluoromethane Chemical compound FCCl XWCDCDSDNJVCLO-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
229920001131 Pulp (paper) Polymers 0.000 description 2
DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
230000009471 action Effects 0.000 description 2
239000012190 activator Substances 0.000 description 2
239000003513 alkali Substances 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
125000000129 anionic group Chemical group 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
ITQTTZVARXURQS-UHFFFAOYSA-N beta-methylpyridine Natural products CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 2
150000001735 carboxylic acids Chemical class 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
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000010894 electron beam technology Methods 0.000 description 2
239000004744 fabric Substances 0.000 description 2
NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
230000003472 neutralizing effect Effects 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
239000000843 powder Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
230000000717 retained effect Effects 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
230000008719 thickening Effects 0.000 description 2
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
229940096522 trimethylolpropane triacrylate Drugs 0.000 description 2
210000002700 urine Anatomy 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
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
SWFHGTMLYIBPPA-UHFFFAOYSA-N (4-methoxyphenyl)-phenylmethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 SWFHGTMLYIBPPA-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
PIMNFNXBTGPCIL-UHFFFAOYSA-N 1-(2-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=CC=C1Br PIMNFNXBTGPCIL-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
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
ZVHZPFSWZWSDEN-UHFFFAOYSA-N 1-bromo-1-fluoroethane Chemical compound CC(F)Br ZVHZPFSWZWSDEN-UHFFFAOYSA-N 0.000 description 1
YACLCMMBHTUQON-UHFFFAOYSA-N 1-chloro-1-fluoroethane Chemical compound CC(F)Cl YACLCMMBHTUQON-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
HXRNFNBDZBGDMQ-UHFFFAOYSA-N 2,2-bis(2-ethylhexoxy)-1-phenylethanone Chemical compound CCCCC(CC)COC(OCC(CC)CCCC)C(=O)C1=CC=CC=C1 HXRNFNBDZBGDMQ-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
IJQUDFHICLYBSO-UHFFFAOYSA-N 2,2-dihexoxy-1-phenylethanone Chemical compound CCCCCCOC(OCCCCCC)C(=O)C1=CC=CC=C1 IJQUDFHICLYBSO-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
SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 1
JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
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238000005456 ore beneficiation Methods 0.000 description 1
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238000010998 test method Methods 0.000 description 1
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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
- 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
- C08F20/00—Homopolymers and 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
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- 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

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Polymers & Plastics (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
Materials Engineering (AREA)
Hematology (AREA)
Dispersion Chemistry (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Absorbent Articles And Supports Therefor (AREA)

CA000379531A 1980-07-08 1981-06-11 Copolymere hydrophile de l'acide acrylique et d'un acrylate Expired CA1209524A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US16693680A	1980-07-08	1980-07-08
US166,936		1980-07-08

Publications (1)

Publication Number	Publication Date
CA1209524A true CA1209524A (fr)	1986-08-12

Family

ID=22605280

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000379531A Expired CA1209524A (fr)	1980-07-08	1981-06-11	Copolymere hydrophile de l'acide acrylique et d'un acrylate

Country Status (12)

Country	Link
EP (1)	EP0055728A4 (fr)
JP (1)	JPS57500930A (fr)
KR (1)	KR830006364A (fr)
BE (1)	BE889553A (fr)
BR (1)	BR8108674A (fr)
CA (1)	CA1209524A (fr)
DK (1)	DK160259C (fr)
ES (1)	ES503685A0 (fr)
GR (1)	GR75718B (fr)
IT (1)	IT1137264B (fr)
MX (1)	MX160466A (fr)
WO (1)	WO1982000147A1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
USRE32649E (en) *	1985-06-18	1988-04-19	The Procter & Gamble Company	Hydrogel-forming polymer compositions for use in absorbent structures
US4654039A (en) *	1985-06-18	1987-03-31	The Proctor & Gamble Company	Hydrogel-forming polymer compositions for use in absorbent structures
JP2817923B2 (ja) *	1987-10-30	1998-10-30	デヴァーズ・エムエス・カンパニー	ソリッドステート電池
CA2136674A1 (fr) *	1994-06-30	1995-12-31	William G. Reeves	Polymere generateur d'hydrogel a proprietes de fracturation utiles
EP1035142A1 (fr) *	1999-03-09	2000-09-13	Nidek Co., Ltd.	Copolymères acrylates pour dispositifs ophtalmiques
FR2876374B1 (fr) *	2004-10-11	2007-02-23	Arkema Sa	Utilisation d'esters phosphoriques comme agents anti-depots lors de la synthese, la purification ou la regeneration de monomeres (meth) acryliques
US7838610B2 (en)	2005-09-30	2010-11-23	Nippon Shokubai Co., Ltd.	Ion-sensitive super-absorbent polymer
JP4994175B2 (ja) *	2007-09-28	2012-08-08	富士フイルム株式会社	平版印刷版原版、及びそれに用いる共重合体の製造方法
CN112094372B (zh) *	2019-06-17	2023-07-14	荒川化学工业株式会社	锂离子电池用粘合剂水溶液、负极用浆料、负极、负极用材料以及锂离子电池及其制造方法

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2511880A (en) *		1950-06-20		Resins of alkyl-substituted cyclo
US2473544A (en) *	1946-03-29	1949-06-21	Chessie E Rehberg	Polyalkyl-cyclohexanol acrylates
US2882261A (en) *	1954-07-21	1959-04-14	Du Pont	Thermoplastic molding composition of cyclohexyl methacrylate, methyl methacrylate and an acrylic acid ester of a saturated alcohol having less than 3 carbon atoms
US2945013A (en) *	1956-03-22	1960-07-12	Monsanto Chemicals	Water-soluble interpolymers of acrylic acids and 2-ethylhexyl esters of acrylic acids and method of making same
US3090736A (en) *	1960-01-27	1963-05-21	Dow Chemical Co	Insoluble polyacrylic acid salts and method of preparing the same
DE1495381B2 (de) *	1963-09-07	1971-06-24	Czeskoslovenska akademie ved , Prag	Verfahren zur herstellung von kontaktlinsen oder kontakt linsenrohlingen aus quellfaehigen hydrogelen
US3468980A (en) *	1966-01-17	1969-09-23	Rohm & Haas	Flame resistant acrylic sheet containing cyclohexyl acrylate or methacrylate copolymer
US3634366A (en) *	1968-05-23	1972-01-11	Daicel Ltd	Polymerizing method
DE1965740C3 (de) *	1969-12-31	1979-11-22	Bayer Ag, 5090 Leverkusen	Verfahren zur Herstellung von pulverisierbaren Acryl-Harzen
US3764502A (en) *	1971-08-12	1973-10-09	Ici America Inc	Water soluble sodium acrylate polymers of high molecular weight
GB1439132A (en) *	1972-03-13	1976-06-09	Special Polymers Ltd	Method for the production of a hydrophilic polymer product
DE2236513C3 (de) *	1972-07-26	1978-12-07	Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt	Einbrennpulverlack
US4115331A (en) *	1973-05-31	1978-09-19	Sanyo Chemical Industries, Ltd.	Surface sizing compositions for paper
US3915921A (en) *	1974-07-02	1975-10-28	Goodrich Co B F	Unsaturated carboxylic acid-long chain alkyl ester copolymers and tri-polymers water thickening agents and emulsifiers
US4172177A (en) *	1975-06-17	1979-10-23	Kyowa Gas Chemical Industry Co., Ltd.	Water insoluble hydrophilic polymer composition
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
US4167464A (en) *	1978-10-16	1979-09-11	The B. F. Goodrich Company	Photopolymerized hydrophilic interpolymers of unsaturated carboxylic acid and esters

1981
- 1981-06-08 WO PCT/US1981/000764 patent/WO1982000147A1/fr not_active Ceased
- 1981-06-08 JP JP56502263A patent/JPS57500930A/ja active Pending
- 1981-06-08 EP EP19810901866 patent/EP0055728A4/fr not_active Withdrawn
- 1981-06-08 BR BR8108674A patent/BR8108674A/pt not_active IP Right Cessation
- 1981-06-11 CA CA000379531A patent/CA1209524A/fr not_active Expired
- 1981-06-25 GR GR65338A patent/GR75718B/el unknown
- 1981-06-29 IT IT22628/81A patent/IT1137264B/it active
- 1981-07-03 KR KR1019810002426A patent/KR830006364A/ko not_active Abandoned
- 1981-07-03 ES ES503685A patent/ES503685A0/es active Granted
- 1981-07-08 MX MX188207A patent/MX160466A/es unknown
- 1981-07-08 BE BE0/205351A patent/BE889553A/fr not_active IP Right Cessation
1982
- 1982-03-05 DK DK098082A patent/DK160259C/da not_active IP Right Cessation

Also Published As

Publication number	Publication date
WO1982000147A1 (fr)	1982-01-21
DK160259C (da)	1991-07-22
JPS57500930A (fr)	1982-05-27
EP0055728A1 (fr)	1982-07-14
IT8122628A0 (it)	1981-06-29
BE889553A (fr)	1981-11-03
EP0055728A4 (fr)	1982-08-11
ES8300804A1 (es)	1982-11-01
DK98082A (da)	1982-03-05
MX160466A (es)	1990-03-08
KR830006364A (ko)	1983-09-24
ES503685A0 (es)	1982-11-01
DK160259B (da)	1991-02-18
GR75718B (fr)	1984-08-02
IT1137264B (it)	1986-09-03
BR8108674A (pt)	1982-05-25

Legal Events

Date	Code	Title	Description
2003-08-12	MKEX	Expiry

Publication	Publication Date	Title
US4167464A (en)	1979-09-11	Photopolymerized hydrophilic interpolymers of unsaturated carboxylic acid and esters
US4486489A (en)	1984-12-04	Films of hydrophilic interpolymers of neutralized acrylic acid, hydroxyalkyl methacrylate or dialkylaminoalkyl (meth)acrylate and optionally a cross-linking agent
EP1682194B1 (fr)	2008-07-09	Particules polymeres absorbant le sang et/ou des liquides organiques
EP0372981B1 (fr)	1995-09-13	Procédé de préparation d'une résine absorbante à longue durabilité
US6414214B1 (en)	2002-07-02	Mechanically stable hydrogel-forming polymers
CA1100748A (fr)	1981-05-12	Traduction non-disponible
WO2002053199A1 (fr)	2002-07-11	Hydrogels revetus de separateurs steriques ou electrostatiques
GB1597613A (en)	1981-09-09	Interpolymers of unsaturated carboxylic acids
EP0068189A1 (fr)	1983-01-05	Copolymères réticulés gonflables à l'eau et leur utilisation comme moyens d'absorption de liquides aqueux corporels, tels que l'urine et d'autres liquides aqueux contenant des électrolytes
DE2734298A1 (de)	1978-10-05	Verbesserte copolymerisate olefinisch ungesaettigter carbonsaeureverbindungen
CA1209524A (fr)	1986-08-12	Copolymere hydrophile de l'acide acrylique et d'un acrylate
WO1999055767A1 (fr)	1999-11-04	Hydrogels a stabilite mecanique
EP0042406B1 (fr)	1985-06-19	Films du fibres hydrophiles photopolymerises constitues d'acide acrylique et d'agents polyfonctionnels de liaison transversale
EP0047009A1 (fr)	1982-03-10	Copolymères hydrophiles d'acide acrylique et une oléfine ou un styrène
CN108948258A (zh)	2018-12-07	吸水性树脂及其制造方法
DE19628863A1 (de)	1997-01-23	Verfahren zur Herstellung von wasserabsorbierendem Harz
JP2003088554A (ja)	2003-03-25	吸収体およびそれを用いた吸収性物品
EP0035538A1 (fr)	1981-09-16	Copolymeres hydrophiles polymerises par irradiation d'acide carboxylique non sature et d'esters
DE10351267A1 (de)	2005-06-02	Blut und/oder Körperflüssigkeiten absorbierendes Hydrogel
WO1990015825A1 (fr)	1990-12-27	Polymere relativement souple et pliable, pouvant se gonfler dans l'eau