JP2013525272A - ポリマー界面活性剤 - Google Patents
ポリマー界面活性剤 Download PDFInfo
- Publication number
- JP2013525272A JP2013525272A JP2013500168A JP2013500168A JP2013525272A JP 2013525272 A JP2013525272 A JP 2013525272A JP 2013500168 A JP2013500168 A JP 2013500168A JP 2013500168 A JP2013500168 A JP 2013500168A JP 2013525272 A JP2013525272 A JP 2013525272A
- Authority
- JP
- Japan
- Prior art keywords
- carboxylic acid
- residue
- group
- oil
- hydroxyalkyl
- 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.)
- Granted
Links
- 239000004094 surface-active agent Substances 0.000 title description 54
- 229920000642 polymer Polymers 0.000 title description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- -1 hydroxyalkenyl carboxylic acid Chemical class 0.000 claims abstract description 38
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 28
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 19
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 15
- 239000002270 dispersing agent Substances 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 14
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 11
- 125000002252 acyl group Chemical group 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 9
- 235000000346 sugar Nutrition 0.000 claims description 8
- 239000003599 detergent Substances 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000000080 wetting agent Substances 0.000 claims description 4
- 150000002772 monosaccharides Chemical class 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 description 44
- 239000000203 mixture Substances 0.000 description 33
- 239000003921 oil Substances 0.000 description 23
- 239000000047 product Substances 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 238000009472 formulation Methods 0.000 description 18
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 17
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 17
- 239000000600 sorbitol Substances 0.000 description 17
- 235000010356 sorbitol Nutrition 0.000 description 17
- 239000007787 solid Substances 0.000 description 16
- 235000019198 oils Nutrition 0.000 description 14
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 12
- 239000006185 dispersion Substances 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- 239000000049 pigment Substances 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 239000012530 fluid Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 229920002401 polyacrylamide Polymers 0.000 description 9
- 238000005553 drilling Methods 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 238000007720 emulsion polymerization reaction Methods 0.000 description 5
- NMJORVOYSJLJGU-UHFFFAOYSA-N methane clathrate Chemical compound C.C.C.C.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O NMJORVOYSJLJGU-UHFFFAOYSA-N 0.000 description 5
- 239000012860 organic pigment Substances 0.000 description 5
- 150000008163 sugars Chemical class 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 239000002360 explosive Substances 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 239000001023 inorganic pigment Substances 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 230000000475 sunscreen effect Effects 0.000 description 4
- 239000000516 sunscreening agent Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229920001400 block copolymer Polymers 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 239000007764 o/w emulsion Substances 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- NGCDGPPKVSZGRR-UHFFFAOYSA-J 1,4,6,9-tetraoxa-5-stannaspiro[4.4]nonane-2,3,7,8-tetrone Chemical compound [Sn+4].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O NGCDGPPKVSZGRR-UHFFFAOYSA-J 0.000 description 2
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-Hydroxyoctadecanoic acid Natural products CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- 229930091371 Fructose Natural products 0.000 description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
- 239000005715 Fructose Substances 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 239000005662 Paraffin oil Substances 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 239000007957 coemulsifier Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000003974 emollient agent Substances 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 239000004088 foaming agent Substances 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 239000000832 lactitol Substances 0.000 description 2
- VQHSOMBJVWLPSR-JVCRWLNRSA-N lactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-JVCRWLNRSA-N 0.000 description 2
- 235000010448 lactitol Nutrition 0.000 description 2
- 229960003451 lactitol Drugs 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000004530 micro-emulsion Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 239000005648 plant growth regulator Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- FRPJTGXMTIIFIT-UHFFFAOYSA-N tetraacetylethylenediamine Chemical compound CC(=O)C(N)(C(C)=O)C(N)(C(C)=O)C(C)=O FRPJTGXMTIIFIT-UHFFFAOYSA-N 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- RMTFNDVZYPHUEF-XZBKPIIZSA-N 3-O-methyl-D-glucose Chemical compound O=C[C@H](O)[C@@H](OC)[C@H](O)[C@H](O)CO RMTFNDVZYPHUEF-XZBKPIIZSA-N 0.000 description 1
- AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 description 1
- 239000004910 After sun product Substances 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000004382 Amylase Substances 0.000 description 1
- 102000013142 Amylases Human genes 0.000 description 1
- 108010065511 Amylases Proteins 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- SHBUUTHKGIVMJT-UHFFFAOYSA-N Hydroxystearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OO SHBUUTHKGIVMJT-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical group CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000004909 Moisturizer Substances 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000003855 acyl compounds Chemical class 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001963 alkali metal nitrate Inorganic materials 0.000 description 1
- 229910001964 alkaline earth metal nitrate Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- OXQKEKGBFMQTML-UHFFFAOYSA-N alpha-Glucoheptitol Chemical group OCC(O)C(O)C(O)C(O)C(O)CO OXQKEKGBFMQTML-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 235000019418 amylase Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000001166 anti-perspirative effect Effects 0.000 description 1
- 239000003213 antiperspirant Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- SNCZNSNPXMPCGN-UHFFFAOYSA-N butanediamide Chemical compound NC(=O)CCC(N)=O SNCZNSNPXMPCGN-UHFFFAOYSA-N 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000008271 cosmetic emulsion Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000002173 cutting fluid Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- HEBKCHPVOIAQTA-NGQZWQHPSA-N d-xylitol Chemical compound OC[C@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-NGQZWQHPSA-N 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical group O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- VTIIJXUACCWYHX-UHFFFAOYSA-L disodium;carboxylatooxy carbonate Chemical compound [Na+].[Na+].[O-]C(=O)OOC([O-])=O VTIIJXUACCWYHX-UHFFFAOYSA-L 0.000 description 1
- 238000012674 dispersion polymerization Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010556 emulsion polymerization method Methods 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000005020 hydroxyalkenyl group Chemical group 0.000 description 1
- 229940072106 hydroxystearate Drugs 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000012688 inverse emulsion polymerization Methods 0.000 description 1
- 239000001034 iron oxide pigment Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940059904 light mineral oil Drugs 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical compound NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 235000019808 microcrystalline wax Nutrition 0.000 description 1
- 238000012703 microemulsion polymerization Methods 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000002482 oligosaccharides Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- 230000005501 phase interface Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000015227 regulation of liquid surface tension Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000010731 rolling oil Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- 229940045872 sodium percarbonate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000005482 strain hardening Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/08—Saturated oxiranes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
- C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/667—Neutral esters, e.g. sorbitan esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/22—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the initiator used in polymerisation
- C08G2650/24—Polymeric initiators
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Saccharide Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
Abstract
R1[(AO)n−A−OR2]m (I)
式中、R1は、少なくともm個の活性水素原子を有する基の残基であり、mは少なくとも2である;AOは、アルキレンオキシド残基である;それぞれのnは、独立して0〜100である;そして、それぞれのR2は、独立してHまたはアシル基COR3、それぞれのR3は、独立してポリヒドロキシアルキルもしくはポリヒドロキシアルケニルカルボン酸の残基、ヒドロキシアルキルもしくはヒドロキシアルケニルカルボン酸の残基および/またはヒドロキシアルキルもしくはヒドロキシアルケニルカルボン酸のオリゴマーの残基であり、平均で少なくとも2つのR2は、アシル基である、で表される化合物。この化合物は、乳化剤および/または分散剤としての使用に特に好適である。
Description
本願は、2010年3月17日に出願された米国特許仮出願第61/282,689号からの優先権の利益を主張するものである。前記の関連出願を参照することにより本明細書の内容とする。
R1[(AO)n−A−OR2]m (I)
式中、
R1は、少なくともm個の活性水素原子を有する基の残基であり、mは少なくとも2である;
AOは、アルキレンオキシド残基である;
それぞれのnは、独立して0〜100である;そして
それぞれのR2は、独立してHまたはアシル基COR3、ここでそれぞれのR3は、独立してポリヒドロキシアルキルもしくはポリヒドロキシアルケニルカルボン酸の残基、ヒドロキシアルキルもしくはヒドロキシアルケニルカルボン酸の残基および/またはヒドロキシアルキルもしくはヒドロキシアルケニルカルボン酸のオリゴマーの残基であり、平均して少なくとも2つのR2は、アシル基である。
1)グリセロールおよびポリグリセロール、特にジグリセロールおよびトリグリセロール、それらの部分エステル、またはいずれかの複数のヒドロキシル基を含むトリグリセリド、例えばひまし油;
2)トリおよび更に高級なポリメチロールアルカン、例えばトリメチロールエタン、トリメチロールプロパンおよびペンタエリスリトール、およびそれらの部分エステル;
3)糖、特には非還元糖、例えばソルビトール、マンニトール、およびラクチトール、糖のエーテル化誘導体、例えばソルビタン(ソルビトールの環式デヒドロ−エーテル)、糖の部分的アルキルアセタール、例えばメチルグルコースおよびアルキル(ポリ)サッカリド、および他の糖のオリゴマー/ポリマー、例えばデキストリン、糖の部分エステル化誘導体、例えば、脂肪酸エステル、例えばラウリン酸、パルミチン酸、オレイン酸、ステアリン酸およびベヘン酸のエステル、ソルビタンのエステル、ソルビトール、およびスクロース、アミノサッカリド、例えば、N−アルキルグルカミンおよびそれらのそれぞれのN−アルキル−N−アルケノイルグルカミド;
4)ポリヒドロキシカルボン酸、特にはクエン酸および酒石酸;
5)アミン、例えばジ−および多官能性アミン、特にはアルキルアミン、例えばアルキルジアミン、例えばエチレンジアミン(1,2−ジアミノエタン);
6)アミノ−アルコール、特にはエタノールアミン、2−アミノエタノール、ジ−エタノールアミンおよびトリエタノールアミン;
7)カルボン酸アミド、例えば尿素、マロンアミドおよびスクシンアミド;ならびに
8)アミドカルボン酸、例えばスクシナミン酸。
<アルコキシル化R基の調製>
<PEG−50ソルビトール>
ステンレス鋼製反応容器中で、ソルビトール70(33.09質量%)を95%まで乾燥し、そしてエチレンオキシド(66.50質量%)と、水酸化カリウムの存在下で反応させた。生成品(27.2質量%)を、次いで水酸化カリウムの存在下で、更なるエチレンオキシド(72.8質量%)と反応させて、PEG−50ソルビトールを生成させた。
<化合物(I)の調製>
12−ヒドロキシステアリン酸(16.5質量%)、Hypermer LP1(15.7質量%、Crodaから販売)、PEG−50ソルビトール(67.7質量%)および蓚酸スズ触媒(Tegokat 160、Goldschmidtから販売)を、ガラス製反応器へと加え、そして窒素圧の下で、190℃にゆっくりと加熱した。反応を、12〜24時間継続し、次いで100℃未満に冷却し、そして生成品を排出した。この化合物は、化合物Aと標示し、そして13.5のHLBを備えた液体であった。
<化合物(I)の調製>
12−ヒドロキシステアリン酸(68.7質量%)、PEG−50ソルビトール(31.3質量%)および蓚酸スズ触媒(Tegokat 160、Goldschmidtから販売)を、ガラス製反応器へと加え、そして窒素圧の下で、190℃にゆっくりと加熱した。反応を、12〜24時間継続し、次いで100℃未満に冷却し、そして生成品を排出した。この化合物は、化合物Bと標示し、そして6.3のHLBを備えた液体であった。
例3の化合物Bの3.2gを、共乳化剤(Crodaから入手可能なTween(登録商標)80)0.8gと混合し、そして2オンスのガラス製ネジ蓋付きの広口ビン中に容れた。40gの軽質鉱油を加え、そしてこの混合物を均一になるまで振とうした。56gの水を加えて、そしてこの混合物を20回振とうした。水中油エマルジョンが形成され、これは、室温で48時間安定であった。
乳化剤混合物を、例2の化合物Aを2.8gと共乳化剤(Crodaから入手可能なSpan(登録商標)80)を1.2gに置き換えて、例4を繰り返した。水中油エマルジョンが形成され、これは、室温で21日間安定であった。
Claims (8)
- 下記の式(I):
R1[(AO)n−A−OR2]m (I)
式中、
R1は、少なくともm個の活性水素原子を有する基の残基であり、mは少なくとも2である;
AOは、アルキレンオキシド残基である;
それぞれのnは、独立して0〜100である;そして
それぞれのR2は、独立してHまたはアシル基COR3、それぞれのR3は、独立してポリヒドロキシアルキルもしくはポリヒドロキシアルケニルカルボン酸の残基、ヒドロキシアルキルもしくはヒドロキシアルケニルカルボン酸の残基および/またはヒドロキシアルキルもしくはヒドロキシアルケニルカルボン酸のオリゴマーの残基であり、平均で少なくとも2つのR2は、アシル基である、
で表される化合物。 - R1が、少なくとも3個の遊離のヒドロキシルおよび/またはアミノ基を有する基の残基である、請求項1記載の化合物。
- R1が、糖、好ましくは単糖の残基である、請求項1または2記載の化合物。
- 3000〜8000の分子量を有する、請求項1〜3のいずれか1項記載の化合物。
- 1.3〜15のHLBを有する、請求項1〜4のいずれか1項記載の化合物。
- 請求項1〜5のいずれか1項記載の化合物の、油中水乳化剤、湿潤剤、水中油乳化剤、洗剤、分散剤および/または可溶化剤としての使用方法。
- 化合物(I)の製造方法であって、基R1を、アルキレンオキシドと反応させ、次いで、該反応のアルコキシル化された生成物を、ポリヒドロキシアルキルもしくはアルケニルカルボン酸および/またはヒドロキシアルキルもしくはアルケニルカルボン酸でエステル化することを含む、方法。
- 前記アルコキシル化された生成品の、ポリヒドロキシアルキルもしくはアルケニルカルボン酸および/またはヒドロキシアルキルもしくはアルケニルカルボン酸に対するモル比が、1:2〜1:40の範囲である、請求項7記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US28268910P | 2010-03-17 | 2010-03-17 | |
US61/282,689 | 2010-03-17 | ||
PCT/US2011/028601 WO2011116049A1 (en) | 2010-03-17 | 2011-03-16 | Polymeric surfactant |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2013525272A true JP2013525272A (ja) | 2013-06-20 |
JP2013525272A5 JP2013525272A5 (ja) | 2014-04-10 |
JP5876467B2 JP5876467B2 (ja) | 2016-03-02 |
Family
ID=44649566
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013500168A Active JP5876467B2 (ja) | 2010-03-17 | 2011-03-16 | ポリマー界面活性剤 |
Country Status (5)
Country | Link |
---|---|
US (1) | US9315621B2 (ja) |
EP (1) | EP2547701B1 (ja) |
JP (1) | JP5876467B2 (ja) |
ES (1) | ES2688798T3 (ja) |
WO (1) | WO2011116049A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014147926A (ja) * | 2013-01-09 | 2014-08-21 | Nof Corp | 非水系分散剤、および非水系分散体組成物 |
KR20160078410A (ko) * | 2013-10-29 | 2016-07-04 | 크로다 인코포레이티드 | 히드록시카르복실 산 유래 마찰 조정제를 포함하는 윤활제 조성물 |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016061760A1 (en) * | 2014-10-22 | 2016-04-28 | Dow Global Technologies Llc | Preparation of sorbate ester |
GB201506948D0 (en) | 2015-04-23 | 2015-06-10 | Croda Int Plc | Emulsions for injectable formulations |
CN107660122A (zh) * | 2015-05-12 | 2018-02-02 | 禾大公司 | 农业化学乳液 |
US10723929B2 (en) | 2015-11-19 | 2020-07-28 | Cnpc Usa Corporation | Thinner for oil-based drilling fluids |
US10723931B2 (en) | 2015-11-19 | 2020-07-28 | Cnpc Usa Corporation | Thinner for oil-based drilling fluids |
AU2017288924B2 (en) * | 2016-07-01 | 2021-05-13 | Croda, Inc. | Spray drift reduction |
JP7178987B2 (ja) * | 2016-08-22 | 2022-11-28 | トレヴィ システムズ インコーポレイテッド | 浸透流体精製及びその駆動化合物 |
US20180071198A1 (en) * | 2016-09-14 | 2018-03-15 | Applechem Inc. | Liquid thickener composition comprising polyalkoxylated polyols polyester for personal care, dermatological, and pharmaceutical preparations |
US20180072817A1 (en) * | 2016-09-15 | 2018-03-15 | Applechem Inc. | Topical preparations comprising polyalkoxylated polyols polyester |
US20230346683A1 (en) * | 2016-09-15 | 2023-11-02 | Applechem Inc. | Topical preparations comprising biodegradable polyalkoxylated polyols polyester |
SG11202001271PA (en) | 2017-08-15 | 2020-03-30 | Saudi Arabian Oil Co | Thermally stable surfactants for oil based drilling fluids |
US10876039B2 (en) | 2017-08-15 | 2020-12-29 | Saudi Arabian Oil Company | Thermally stable surfactants for oil based drilling fluids |
US10988659B2 (en) | 2017-08-15 | 2021-04-27 | Saudi Arabian Oil Company | Layered double hydroxides for oil-based drilling fluids |
US10745606B2 (en) | 2017-08-15 | 2020-08-18 | Saudi Arabian Oil Company | Oil-based drilling fluid compositions which include layered double hydroxides as rheology modifiers |
US10676658B2 (en) | 2017-08-15 | 2020-06-09 | Saudi Arabian Oil Company | Oil-based drilling fluids for high pressure and high temperature drilling operations |
US10793762B2 (en) | 2017-08-15 | 2020-10-06 | Saudi Arabian Oil Company | Layered double hydroxides for oil-based drilling fluids |
US10640696B2 (en) | 2017-08-15 | 2020-05-05 | Saudi Arabian Oil Company | Oil-based drilling fluids for high pressure and high temperature drilling operations |
US10647903B2 (en) | 2017-08-15 | 2020-05-12 | Saudi Arabian Oil Company | Oil-based drilling fluid compositions which include layered double hydroxides as rheology modifiers and amino amides as emulsifiers |
US20210100177A1 (en) * | 2019-10-04 | 2021-04-08 | Milliken & Company | Horticulture Additive |
US11155748B2 (en) * | 2019-10-14 | 2021-10-26 | Baker Hughes Oilfield Operations Llc | Star polymers and methods of use for downhole fluids |
FR3104608B1 (fr) | 2019-12-13 | 2021-12-24 | Total Marketing Services | Composition lubrifiante pour limiter le frottement |
JP2024519183A (ja) * | 2021-05-28 | 2024-05-08 | カーギル・バイオインダストリアル・ユーケイ・リミテッド | トラクション係数添加剤を含む潤滑剤組成物 |
EP4292580A1 (en) | 2022-06-13 | 2023-12-20 | Applechem Inc. | Preparations comprising biodegradable polyalkoxylated polyols polyester |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS49108012A (ja) * | 1972-02-15 | 1974-10-14 | ||
JPS5418898A (en) * | 1977-07-12 | 1979-02-13 | Ici Ltd | Block or graft copolymer and surfactant containing it |
JPH06340598A (ja) * | 1993-05-28 | 1994-12-13 | Lion Corp | 新規なジエステルジアミン化合物、その中間体及びその製造方法と柔軟剤 |
JPH08245527A (ja) * | 1995-03-16 | 1996-09-24 | Kao Corp | 新規な第4級アンモニウム塩及びその製造法 |
JPH1112125A (ja) * | 1997-06-07 | 1999-01-19 | Imperial Chem Ind Plc <Ici> | 界面活性剤を含むパーソナルケア組成物 |
JP2000502743A (ja) * | 1996-03-15 | 2000-03-07 | エルフ アンタル フランス | 乳化燃料及びその製造方法 |
JP2000210504A (ja) * | 1999-01-27 | 2000-08-02 | Sannopuko Kk | 耐水性消泡剤組成物 |
JP2003500368A (ja) * | 1999-05-24 | 2003-01-07 | ソーナス ファーマシューティカルス,インコーポレイテッド | 溶解度が不十分な薬剤のためのエマルジョンビヒクル |
JP2005041819A (ja) * | 2003-07-23 | 2005-02-17 | Asahi Denka Kogyo Kk | アシル基と水酸基とを有する脂肪族化合物及びそのアルキレンオキシド付加物及びこれらの製造方法 |
WO2005059042A2 (en) * | 2003-12-17 | 2005-06-30 | Imperial Chemical Industries Plc | Surfactant |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5343787A (en) | 1976-10-01 | 1978-04-20 | Kao Corp | Emulsifier for emulsion polymerization |
GB8410393D0 (en) | 1984-04-24 | 1984-05-31 | Ici Plc | Fluid compositions |
US4687843A (en) | 1985-07-16 | 1987-08-18 | Amerchol Corporation | Esterified propoxylated glucose compositions |
GB9704126D0 (en) | 1997-02-27 | 1997-04-16 | Ici Plc | Surfactants |
DE10150725A1 (de) | 2001-10-13 | 2003-04-17 | Cognis Deutschland Gmbh | Aniontensidfreie niedrigviskose Trübungsmittel |
DE10211801B4 (de) | 2002-03-16 | 2004-09-30 | Clariant Gmbh | Kosmetische und pharmazeutische Zubereitungen enthaltend einen oxalkylierten Polyglycerinester |
US6797685B2 (en) | 2002-04-26 | 2004-09-28 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Liquid laundry detergent with emulsion layer |
DE102005026522B4 (de) | 2005-06-08 | 2007-04-05 | Henkel Kgaa | Verstärkung der Reinigungsleistung von Waschmitteln durch Polymer |
-
2011
- 2011-03-16 ES ES11756898.0T patent/ES2688798T3/es active Active
- 2011-03-16 JP JP2013500168A patent/JP5876467B2/ja active Active
- 2011-03-16 EP EP11756898.0A patent/EP2547701B1/en active Active
- 2011-03-16 US US13/634,652 patent/US9315621B2/en active Active
- 2011-03-16 WO PCT/US2011/028601 patent/WO2011116049A1/en active Application Filing
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS49108012A (ja) * | 1972-02-15 | 1974-10-14 | ||
JPS5418898A (en) * | 1977-07-12 | 1979-02-13 | Ici Ltd | Block or graft copolymer and surfactant containing it |
JPH06340598A (ja) * | 1993-05-28 | 1994-12-13 | Lion Corp | 新規なジエステルジアミン化合物、その中間体及びその製造方法と柔軟剤 |
JPH08245527A (ja) * | 1995-03-16 | 1996-09-24 | Kao Corp | 新規な第4級アンモニウム塩及びその製造法 |
JP2000502743A (ja) * | 1996-03-15 | 2000-03-07 | エルフ アンタル フランス | 乳化燃料及びその製造方法 |
JPH1112125A (ja) * | 1997-06-07 | 1999-01-19 | Imperial Chem Ind Plc <Ici> | 界面活性剤を含むパーソナルケア組成物 |
JP2000210504A (ja) * | 1999-01-27 | 2000-08-02 | Sannopuko Kk | 耐水性消泡剤組成物 |
JP2003500368A (ja) * | 1999-05-24 | 2003-01-07 | ソーナス ファーマシューティカルス,インコーポレイテッド | 溶解度が不十分な薬剤のためのエマルジョンビヒクル |
JP2005041819A (ja) * | 2003-07-23 | 2005-02-17 | Asahi Denka Kogyo Kk | アシル基と水酸基とを有する脂肪族化合物及びそのアルキレンオキシド付加物及びこれらの製造方法 |
WO2005059042A2 (en) * | 2003-12-17 | 2005-06-30 | Imperial Chemical Industries Plc | Surfactant |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014147926A (ja) * | 2013-01-09 | 2014-08-21 | Nof Corp | 非水系分散剤、および非水系分散体組成物 |
KR20160078410A (ko) * | 2013-10-29 | 2016-07-04 | 크로다 인코포레이티드 | 히드록시카르복실 산 유래 마찰 조정제를 포함하는 윤활제 조성물 |
KR102190754B1 (ko) | 2013-10-29 | 2020-12-15 | 크로다 인코포레이티드 | 히드록시카르복실 산 유래 마찰 조정제를 포함하는 윤활제 조성물 |
Also Published As
Publication number | Publication date |
---|---|
EP2547701A1 (en) | 2013-01-23 |
JP5876467B2 (ja) | 2016-03-02 |
US9315621B2 (en) | 2016-04-19 |
WO2011116049A1 (en) | 2011-09-22 |
CN102918065A (zh) | 2013-02-06 |
EP2547701B1 (en) | 2018-07-04 |
EP2547701A4 (en) | 2015-10-28 |
ES2688798T3 (es) | 2018-11-07 |
US20130079536A1 (en) | 2013-03-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5876467B2 (ja) | ポリマー界面活性剤 | |
KR101108824B1 (ko) | 계면활성제 화합물 | |
US8097564B2 (en) | Surfactant compounds | |
EP2454296B1 (de) | Copolymere, ihre verwendung als verdicker, und verfahren zu ihrer herstellung | |
AU2004205651A1 (en) | Low color polyisobutylene succinic anhydride-derived emulsifiers | |
JP2007528431A (ja) | 界面活性剤およびコサーファクタントを含有する混合物 | |
Agach et al. | Acyl poly (glycerol-succinic acid) Oligoesters: synthesis, physicochemical and functional properties, and biodegradability | |
US7696146B2 (en) | Mixture, comprising a surfactant and a cosurfactant | |
JP2008522796A (ja) | 添加剤による界面活性剤及び乳化剤の効果向上方法 | |
CN102918065B (zh) | 聚合物表面活性剂 | |
Bognolo | Nonionic surfactants | |
WO2022148662A1 (fr) | Composition détergente comprenant comme agent épaississant une composition qui présente des propriétés épaississantes de milieux polaires | |
JP5162157B2 (ja) | 親油性成分含有粉末 | |
EP3517177A1 (en) | Composition for increasing the viscosity of an oil | |
WO2014150782A1 (en) | Ketal adducts, methods of manufacture, and uses thereof | |
KR20060111181A (ko) | 생분해성이 우수한 제미니형 계면활성제 및 이의 제조방법 | |
WO2007051632A2 (en) | Surfactant precursor |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140219 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20140219 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20150227 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20150303 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20150602 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20150826 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20160105 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20160121 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5876467 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |