CN110959036A - 洗涤剂添加剂 - Google Patents
洗涤剂添加剂 Download PDFInfo
- Publication number
- CN110959036A CN110959036A CN201880049833.3A CN201880049833A CN110959036A CN 110959036 A CN110959036 A CN 110959036A CN 201880049833 A CN201880049833 A CN 201880049833A CN 110959036 A CN110959036 A CN 110959036A
- Authority
- CN
- China
- Prior art keywords
- detergent additive
- diacrylate
- cyanoacetate
- michael
- group
- 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
- 239000000654 additive Substances 0.000 title claims abstract description 37
- 230000000996 additive effect Effects 0.000 title claims abstract description 32
- 239000003599 detergent Substances 0.000 title claims abstract description 32
- 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 claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 10
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 5
- HRSYISMFWLVXAQ-UHFFFAOYSA-N n-[2-(diacetylamino)ethyl]acetamide Chemical compound CC(=O)NCCN(C(C)=O)C(C)=O HRSYISMFWLVXAQ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000004729 acetoacetic acid derivatives Chemical class 0.000 claims abstract description 4
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000002690 malonic acid derivatives Chemical class 0.000 claims abstract description 4
- 238000005538 encapsulation Methods 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- -1 malonate ester Chemical class 0.000 claims description 6
- MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 claims description 5
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 claims description 4
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 claims description 4
- 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
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims description 4
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical compound C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 claims description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000004386 diacrylate group Chemical group 0.000 claims description 4
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 3
- LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 claims description 3
- PCLLJCFJFOBGDE-UHFFFAOYSA-N (5-bromo-2-chlorophenyl)methanamine Chemical compound NCC1=CC(Br)=CC=C1Cl PCLLJCFJFOBGDE-UHFFFAOYSA-N 0.000 claims description 2
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 claims description 2
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 claims description 2
- VRWWRSQIOZLGAM-UHFFFAOYSA-N 2,2-bis(3-oxobutanoyloxymethyl)butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC(CC)(COC(=O)CC(C)=O)COC(=O)CC(C)=O VRWWRSQIOZLGAM-UHFFFAOYSA-N 0.000 claims description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims description 2
- BCFBCLJFXYLWCI-UHFFFAOYSA-N 2,3-bis(3-oxobutanoyloxy)propyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC(OC(=O)CC(C)=O)COC(=O)CC(C)=O BCFBCLJFXYLWCI-UHFFFAOYSA-N 0.000 claims description 2
- PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 claims description 2
- YIJYFLXQHDOQGW-UHFFFAOYSA-N 2-[2,4,6-trioxo-3,5-bis(2-prop-2-enoyloxyethyl)-1,3,5-triazinan-1-yl]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCN1C(=O)N(CCOC(=O)C=C)C(=O)N(CCOC(=O)C=C)C1=O YIJYFLXQHDOQGW-UHFFFAOYSA-N 0.000 claims description 2
- GTELLNMUWNJXMQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO GTELLNMUWNJXMQ-UHFFFAOYSA-N 0.000 claims description 2
- ZNYBQVBNSXLZNI-UHFFFAOYSA-N 2-ethylhexyl 2-cyanoacetate Chemical compound CCCCC(CC)COC(=O)CC#N ZNYBQVBNSXLZNI-UHFFFAOYSA-N 0.000 claims description 2
- QAUIAXORENGBSN-UHFFFAOYSA-N 2-ethylhexyl 3-oxobutanoate Chemical compound CCCCC(CC)COC(=O)CC(C)=O QAUIAXORENGBSN-UHFFFAOYSA-N 0.000 claims description 2
- IHSFHIUGYHMYNR-UHFFFAOYSA-N 4-(3-oxobutanoyloxy)butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCCCOC(=O)CC(C)=O IHSFHIUGYHMYNR-UHFFFAOYSA-N 0.000 claims description 2
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 claims description 2
- PVVNFQFWDCPPNQ-UHFFFAOYSA-N 6-(3-oxobutanoyloxy)hexyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCCCCCOC(=O)CC(C)=O PVVNFQFWDCPPNQ-UHFFFAOYSA-N 0.000 claims description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 2
- REIYHFWZISXFKU-UHFFFAOYSA-N Butyl acetoacetate Chemical compound CCCCOC(=O)CC(C)=O REIYHFWZISXFKU-UHFFFAOYSA-N 0.000 claims description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- MXHUVJDCDLWMKY-UHFFFAOYSA-N [1-(3-oxobutanoyloxymethyl)cyclohexyl]methyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC1(COC(=O)CC(C)=O)CCCCC1 MXHUVJDCDLWMKY-UHFFFAOYSA-N 0.000 claims description 2
- RASITSWSKYLIEX-UHFFFAOYSA-N [2,2-dimethyl-3-(3-oxobutanoyloxy)propyl] 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC(C)(C)COC(=O)CC(C)=O RASITSWSKYLIEX-UHFFFAOYSA-N 0.000 claims description 2
- AUHWLIZFLUXUDG-UHFFFAOYSA-N [3-(3-oxobutanoyloxy)-2,2-bis(3-oxobutanoyloxymethyl)propyl] 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC(COC(=O)CC(C)=O)(COC(=O)CC(C)=O)COC(=O)CC(C)=O AUHWLIZFLUXUDG-UHFFFAOYSA-N 0.000 claims description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 claims description 2
- YSRBRMMHTQOUDW-UHFFFAOYSA-N bis(2-ethylhexyl) propanedioate Chemical compound CCCCC(CC)COC(=O)CC(=O)OCC(CC)CCCC YSRBRMMHTQOUDW-UHFFFAOYSA-N 0.000 claims description 2
- AOESAXAWXYJFNC-UHFFFAOYSA-N bis(prop-2-enyl) propanedioate Chemical compound C=CCOC(=O)CC(=O)OCC=C AOESAXAWXYJFNC-UHFFFAOYSA-N 0.000 claims description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 2
- DJACTCNGCHPGOI-UHFFFAOYSA-N butyl 2-cyanoacetate Chemical compound CCCCOC(=O)CC#N DJACTCNGCHPGOI-UHFFFAOYSA-N 0.000 claims description 2
- NFKGQHYUYGYHIS-UHFFFAOYSA-N dibutyl propanedioate Chemical compound CCCCOC(=O)CC(=O)OCCCC NFKGQHYUYGYHIS-UHFFFAOYSA-N 0.000 claims description 2
- LKNAVAQNRCASPT-UHFFFAOYSA-N didodecyl propanedioate Chemical compound CCCCCCCCCCCCOC(=O)CC(=O)OCCCCCCCCCCCC LKNAVAQNRCASPT-UHFFFAOYSA-N 0.000 claims description 2
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 claims description 2
- RYFZYSKTNJAFQD-UHFFFAOYSA-N dodecyl 2-cyanoacetate Chemical compound CCCCCCCCCCCCOC(=O)CC#N RYFZYSKTNJAFQD-UHFFFAOYSA-N 0.000 claims description 2
- KCHWKBCUPLJWJA-UHFFFAOYSA-N dodecyl 3-oxobutanoate Chemical compound CCCCCCCCCCCCOC(=O)CC(C)=O KCHWKBCUPLJWJA-UHFFFAOYSA-N 0.000 claims description 2
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 claims description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 claims description 2
- 150000007530 organic bases Chemical group 0.000 claims description 2
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- WXKCRCGKCOKJEF-UHFFFAOYSA-N prop-2-enyl 2-cyanoacetate Chemical compound C=CCOC(=O)CC#N WXKCRCGKCOKJEF-UHFFFAOYSA-N 0.000 claims description 2
- AXLMPTNTPOWPLT-UHFFFAOYSA-N prop-2-enyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC=C AXLMPTNTPOWPLT-UHFFFAOYSA-N 0.000 claims description 2
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 claims description 2
- GAFINJXANQZOKT-UHFFFAOYSA-N cyano acetate Chemical compound CC(=O)OC#N GAFINJXANQZOKT-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 229910001868 water Inorganic materials 0.000 description 15
- 239000000203 mixture Substances 0.000 description 12
- 238000009472 formulation Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- WNYIBZHOMJZDKN-UHFFFAOYSA-N n-(2-acetamidoethyl)acetamide Chemical compound CC(=O)NCCNC(C)=O WNYIBZHOMJZDKN-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 6
- 239000000975 dye Substances 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000013543 active substance Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 239000007844 bleaching agent Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000010419 fine particle Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 238000006957 Michael reaction Methods 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000008406 cosmetic ingredient Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 229940039227 diagnostic agent Drugs 0.000 description 1
- 239000000032 diagnostic agent Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 235000002864 food coloring agent Nutrition 0.000 description 1
- 239000000989 food dye Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000009775 high-speed stirring Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011785 micronutrient Substances 0.000 description 1
- 235000013369 micronutrients Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 230000003711 photoprotective effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
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- 230000004224 protection Effects 0.000 description 1
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- 230000002940 repellent Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
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- 239000013042 solid detergent Substances 0.000 description 1
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- 238000012360 testing method Methods 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
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Classifications
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/32—Amides; Substituted amides
-
- 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
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/0039—Coated compositions or coated components in the compositions, (micro)capsules
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2093—Esters; Carbonates
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
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- C—CHEMISTRY; METALLURGY
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Abstract
一种包含活性物质的洗涤剂添加剂,所述活性物质包含四乙酰乙二胺或三乙酰乙二胺中的一种或两种;以及充当迈克尔供体的化合物与充当迈克尔受体的化合物的反应产物;其中,充当迈克尔供体的化合物选自由以下组成的组:乙酰乙酸酯、氰基乙酸酯和丙二酸酯;充当迈克尔受体的化合物是多官能丙烯酸酯;并且洗涤剂添加剂中的四乙酰乙二胺的重量%是10至90%。
Description
背景技术
有许多应用希望包封活性物质。例如,纺织品(如可穿戴织物)典型地通过使纺织品与洗涤剂配方接触来进行洗涤,所述洗涤剂配方是洗涤剂组分和其它任选的活性物质(如漂白剂)的组合。为了容易使用,许多洗涤剂配方用户更喜欢多合一产品,从而将洗涤剂和任选的活性物质合并成单一产品。此外,相比于固体或颗粒状产品,许多用户更喜欢此产品为液体。
一种常见的洗涤剂活性物质是四乙酰乙二胺(TAED)。TAED充当过氧漂白活化剂和微生物控制剂。TAED已广泛地用于固体洗涤剂产品中。在部分含有水的液体洗涤剂配方中,TAED将经历水解并且失去作为洗涤剂活性物质的有效性,因为TAED反应形成N,N′二乙酰乙二胺(DAED),其不具有作为洗涤剂活性物质的有效性。因此,当在不修饰的情况下使用时,TAED作为水性洗涤剂配方的活性物质并不理想。三乙酰乙二胺(TriAED)是另一种洗涤剂活性物质。期望一种含有活性物质的添加剂,所述活性物质适用于含有水的配方中。
发明内容
一种包含活性物质的洗涤剂添加剂,所述活性物质包含四乙酰乙二胺或三乙酰乙二胺中的一种或两种;以及充当迈克尔供体的化合物与充当迈克尔受体的化合物的反应产物;其中,充当迈克尔供体的化合物选自由以下组成的组:乙酰乙酸酯、氰基乙酸酯和丙二酸酯;充当迈克尔受体的化合物是多官能丙烯酸酯;并且洗涤剂添加剂中的四乙酰乙二胺的重量%是10至90%。
具体实施方式
本公开描述了一种添加剂,其包含四乙酰乙二胺(TAED)或三乙酰乙二胺(TriAED)中的一种或两种以及充当迈克尔供体的化合物与充当迈克尔受体的化合物作为迈克尔反应的一部分而形成的反应产物。充当迈克尔供体的化合物与充当迈克尔受体的化合物作为迈克尔反应的一部分而形成的反应产物在本文中通常称为迈克尔产物。迈克尔反应是亲核试剂(充当迈克尔供体的化合物)在迈克尔催化剂存在下1,4-加成到活化烯烃(充当迈克尔受体的化合物),例如α,β-不饱和羰基化合物(例如丙烯酸酯)。
用作迈克尔供体的化合物选自由乙酰乙酸酯、氰基乙酸酯和丙二酸酯组成的组。在一个实例中,乙酰乙酸酯是单乙酰乙酸酯、二乙酰乙酸酯、三乙酰乙酸酯或四乙酰乙酸酯,并且优选以下中的一种:乙酰乙酸乙酯、乙酰乙酸1-丁酯、乙酰乙酸甲酯、乙酰乙酸2-乙基己酯、乙酰乙酸月桂酯、乙酰乙酸烯丙酯、1,4-丁二醇二乙酰乙酸酯、1,6-己二醇二乙酰乙酸酯、新戊二醇二乙酰乙酸酯、环己烷二甲醇二乙酰乙酸酯、乙氧基化双酚A二乙酰乙酸酯、三羟甲基丙烷三乙酰乙酸酯、甘油三乙酰乙酸酯或季戊四醇四乙酰乙酸酯。在一个实例中,氰基乙酸酯是单或双氰基乙酸酯,并且优选以下中的一种:氰基乙酸乙酯、氰基乙酸丁酯、氰基乙酸甲酯、氰基乙酸2-乙基己酯、氰基乙酸月桂酯、氰基乙酸烯丙酯和1,4-丁二醇双(氰基乙酸酯)。在一个实例中,丙二酸酯是以下中的一种:丙二酸二乙酯、丙二酸二甲酯、丙二酸二丁酯、丙二酸双(2-乙基己基)酯、丙二酸二月桂酯或丙二酸二烯丙酯。
充当迈克尔受体的化合物是多官能丙烯酸酯。在一个实例中,多官能丙烯酸酯是二丙烯酸酯,其优选选自以下中的一种:1,4-丁二醇二丙烯酸酯、二丙二醇二丙烯酸酯、环己烷二甲醇二丙烯酸酯、烷氧基化己二醇二丙烯酸酯、双酚A二丙烯酸酯、二乙二醇二丙烯酸酯、乙氧基化双酚A二丙烯酸酯、1,6-己二醇二丙烯酸酯、新戊二醇二丙烯酸酯、聚乙二醇二丙烯酸酯、丙氧基化新戊二醇二丙烯酸酯、四乙二醇二丙烯酸酯、三乙二醇二丙烯酸酯,和三丙二醇二丙烯酸酯。在一个实例中,多官能丙烯酸酯是三丙烯酸酯,优选选自以下中的一种:三羟甲基丙烷三丙烯酸酯、乙氧基化三羟甲基丙烷三丙烯酸酯、三(2-羟乙基)异氰尿酸酯三丙烯酸酯、丙氧基化甘油三丙烯酸酯和季戊四醇三丙烯酸酯。在一个实例中,多官能丙烯酸酯是丙氧基化三羟甲基丙烷、丙烯酸化聚酯低聚物或丙烯酸化氨基甲酸酯低聚物。
迈克尔反应在反应混合物中进行,所述反应混合物包括充当迈克尔催化剂的化合物。迈克尔催化剂优选有机或无机碱。充当迈克尔催化剂的化合物实例包括1,1,3,3-四甲基胍、1,8-二氮杂双环[5.4.0]十一碳-7-烯、NaOH、KOH、K2CO3。
充当迈克尔催化剂的化合物优选在反应混合物中以充当迈克尔供体的化合物的0.1至10总摩尔当量存在。反应混合物可以在溶剂的存在或不存在下进行,所述溶剂包括水、醇、醚、烃或氯化烃。温度可以在-10℃至150℃范围内。充当迈克尔供体的化合物相对于充当迈克尔受体的化合物优选以0.5∶1至2.0∶1范围内的比率存在。
本文所述的添加剂如下制备:首先提供分散相。分散相含有水和乳化剂。在一个实例中,乳化剂是水溶性聚合物。在一个实例中,乳化剂是表面活性剂。在一个实例中,乳化剂是聚乙烯醇或取代的纤维素。适合乳化剂的实例包括甲基纤维素、脂肪醇的乙氧基化物、去水山梨醇酯、聚甘油脂肪酸酯,和有机酸单甘油酯{。在反应混合物中分别地合并充当迈克尔供体的化合物、充当迈克尔受体的化合物和活性物质。将分散相加入反应混合物中并且混合形成乳液。然后将充当迈克尔催化剂对化合物加入乳液中混合,直到添加剂以悬浮于乳液中的珠粒形式形成为止。分离固体添加剂珠粒并且形成细颗粒,例如过筛形成。
添加剂是90重量%或更少的活性物质和10重量%或更多的迈克尔产物。添加剂是75重量%或更少的活性物质和25重量%或更多的迈克尔产物。优选地,添加剂是50重量%或更少的活性物质和50重量%或更多的迈克尔产物。
本文所述的添加剂在水性系统中的稳定性比单独的活性物质(例如TAED)更好。例如,当添加剂是洗涤剂添加剂并且用于洗衣机中时,活性物质从共聚物中释放出来,从而让活性物质在洗涤系统中用于发挥其洗涤剂强化功能。
添加剂颗粒可任选地碾磨或研磨成粉末形式而得到固体活性成分,所述固体活性成分具有可控或延迟的释放特征。
如本文所述,添加剂包封或部分地包封活性物质。如本文所用,“包封”是指活性物质结合于或滞留于迈克尔产物网状结构中。本文所述的添加剂经设计以在触发事件期间释放活性物质(在本公开的上下文中,触发事件可用于洗衣机中)。当提及活性物质被包封时,是指在触发事件之前,活性物质滞留于迈克尔产物网状结构内。根据本公开的方法制备的添加剂具有30到100%的包封效率。优选地,根据本公开的方法制备的添加剂具有60到100%的包封效率。更优选地,根据本公开的方法制备的添加剂具有90到100%的包封效率。如本文所用,“包封效率”是指预期的活性物质包封于添加剂的迈克尔产物网状结构中的百分比。
本文所述的方法适合于制备其它类型的固体粉末系统。例如,本文所述的方法可以包括但不限于包封织物软化剂、洗涤剂活性物质、漂白剂活性物质、肥料、微量营养素、农药(杀真菌剂、杀细菌剂、杀昆虫剂、杀螨剂、杀线虫剂等)、杀生物剂、微生物控制剂、聚合物润滑剂、阻燃剂、颜料、染料、尿素抑制剂、食品添加剂、调味剂、医药剂、组织、抗氧化剂、化妆品成分(芳香剂、香料等)、土壤改良剂(土壤拒斥剂、土壤释放剂等)、催化剂、诊断剂和光保护剂(紫外阻隔剂等)。
选择在水中具有极低溶解度的活性物质,以便与本文所述的包封方法相容。优选地,活性物质在水中的溶解度在25℃下是1%(w/w)或更小。优选地,活性物质在水中的溶解度在25℃下是0.5%(w/w)或更小。如本文所用,(w/w)是指在特定的水温下,单位重量水中的活性物质重量。
实例
材料和包封实例
实例1
季戊四醇三丙烯酸酯(SR444)获自Sartomer公司。TAED获自Alfa Aesar。所有其它化学品均获自Sigma-Aldrich并且原样使用。去离子(DI)水无需进一步提纯即使用。
表1:实例1的配方
按照表1所列的配方,在小玻璃罐中用搅棒搅拌2分钟来制备分散相(去离子水、甲基纤维素)。
如表1所示,将预定量的迈克尔供体、迈克尔受体和TAED加入配备有搅棒和两个玻璃塞的100ml 3颈烧瓶中。迈克尔供体和迈克尔受体的总量是20克,因此TAED相对于迈克尔受体与迈克尔供体组合的重量比为1∶2。将搅棒连接至顶置式高速搅拌器并且缓慢开启混合器。搅拌2分钟后,停止搅拌并且将分散相加入烧瓶中。开启搅拌器并且将rpm逐渐增加到最大值2500rpm。继续高速搅拌2分钟,然后减慢至2000rpm再维持2分钟。将1,1,3,3-四甲基胍(TMG)逐滴加入经搅拌的乳液中。搅拌2小时后获得聚合物珠粒。分离出固体颗粒并且用去离子水洗涤并且离心。收集固体颗粒并且在35℃的真空烘箱中干燥2小时。经由通过200微米筛,固体容易碎裂成细颗粒。
实例2
表2:实例2的配方
按照实例2的配方重复实例1的程序。经由通过500微米筛,所得固体产物容易碎裂成细颗粒。TAED相对于迈克尔供体和迈克尔受体组合的重量比是3∶1。
包封性能评估
方法1:蓝色食用染料的漂白(氧化)
将5滴蓝色水性食用染料(FD&C蓝#1,三芳基甲烷染料)加入500ml水中且混合1小时,产生均匀的染料/水溶液。将1克染料/水溶液、购自Sigma-Aldrich的1克H2O230%水溶液和目标量的TAED(如表3中所列)加入小瓶中并且混合5分钟,如表3中所详列。
12小时后评估指示漂白(氧化)性能的蓝色损失并且与对照样品和比较样品进行比较。对照样品和比较样品按照表3中提供的配方制备(注意:比较样品中提供的TAED未包封,而是直接提供到小瓶中;对照样品是缺乏TAED的H2O2)。
表3:食用彩色染料评估的样品配方
如表3所示,在室温下放置整夜(12小时)后,含有未包封的TAED的比较瓶的蓝色已漂白(褪色)。含有过氧化氢且无TAED的对照瓶未发生可观察到的颜色变化。观察到含有已包封的TAED的样品瓶1在12小时后具有相似的蓝色,表明包封效率良好。
方法2:用于测定TAED水解成DAED的HPLC分析
将选自表1和2中所列实例的0.5g无包封TAED和已包封TAED粉末各自个别地加入含有20g AllTMMighty PacTM洗涤剂的小瓶中,并且振荡10分钟。将1滴(约0.1g)得自各小瓶的混合物个别地加入含有10g 1∶3乙腈/H2O溶剂的单独瓶中,并且声波处理15分钟以完全溶解固体TAED。使用配有四元泵和二极管阵列检测器的Agilent 1100高效液相色谱(HPLC)测量所制样品中的二乙酰乙二胺(DAED)浓度。HPLC方法的条件概述于表4中。
表4:HPLC测试条件
表5:DAED浓度(%)的HPLC评估结果
首日 | 第2天 | 第7天 | 第20天 | 第36天 | |
未包封的TAED | 0.0000 | 0.1162 | 0.2845 | 0.5928 | 0.7602 |
实例1 | 0.0000 | 0.0000 | 0.0345 | 0.0753 | 0.0594 |
实例2 | 0.0000 | 0.0488 | 0.1247 | 0.2072 | 0.2670 |
如表5所示,对于无任何包封的TAED。DAED浓度急剧增加,而其它实例的DAED缓慢增加。由于DAED是由TAED降解产生的,因此DAED的缓慢释放特征表明包封壳的良好包封效率和有效保护。
Claims (11)
1.一种洗涤剂添加剂,其包含:
活性物质,所述活性物质包含四乙酰乙二胺或三乙酰乙二胺中的一种或两种;和
充当迈克尔供体的化合物与充当迈克尔受体的化合物的反应产物;其中,
充当迈克尔供体的所述化合物选自由以下组成的组:乙酰乙酸酯、氰基乙酸酯和丙二酸酯;
充当迈克尔受体的所述化合物是多官能丙烯酸酯;并且
所述洗涤剂添加剂中的四乙酰乙二胺重量%是10至90%。
2.根据权利要求1所述的洗涤剂添加剂,其中所述多官能丙烯酸酯是选自由以下组成的组的二丙烯酸酯:1,4-丁二醇二丙烯酸酯、二丙二醇二丙烯酸酯、环己烷二甲醇二丙烯酸酯、烷氧基化己二醇二丙烯酸酯、双酚A二丙烯酸酯、二乙二醇二丙烯酸酯、乙氧基化双酚A二丙烯酸酯、1,6-己二醇二丙烯酸酯、新戊二醇二丙烯酸酯、聚乙二醇二丙烯酸酯、丙氧基化新戊二醇二丙烯酸酯、四乙二醇二丙烯酸酯、三乙二醇二丙烯酸酯,和三丙二醇二丙烯酸酯。
3.根据权利要求1所述的洗涤剂添加剂,其中所述多官能丙烯酸酯是选自由以下组成的组的三丙烯酸酯:三羟甲基丙烷三丙烯酸酯、乙氧基化三羟甲基丙烷三丙烯酸酯、三(2-羟乙基)异氰尿酸酯三丙烯酸酯、丙氧基化甘油基三丙烯酸酯和季戊四醇三丙烯酸酯。
4.根据权利要求1所述的洗涤剂添加剂,其中所述多官能丙烯酸酯选自由以下组成的组:丙氧基化三羟甲基丙烷、丙烯酸化聚酯低聚物,和丙烯酸化氨基甲酸酯低聚物。
5.根据权利要求1所述的洗涤剂添加剂,其中所述乙酰乙酸酯是选自由以下组成的组的单乙酰乙酸酯、二乙酰乙酸酯、三乙酰乙酸酯或四乙酰乙酸酯:乙酰乙酸乙酯、乙酰乙酸1-丁酯、乙酰乙酸甲酯、乙酰乙酸2-乙基己酯、乙酰乙酸月桂酯、乙酰乙酸烯丙酯、1,4-丁二醇二乙酰乙酸酯、1,6-己二醇二乙酰乙酸酯、新戊二醇二乙酰乙酸酯、环己烷二甲醇二乙酰乙酸酯、乙氧基化双酚A二乙酰乙酸酯、三羟甲基丙烷三乙酰乙酸酯、甘油三乙酰乙酸酯,和季戊四醇四乙酰乙酸酯。
6.根据权利要求1所述的洗涤剂添加剂,其中所述氰基乙酸酯是选自由以下组成的组的单氰基乙酸酯或双氰基乙酸酯:氰基乙酸乙酯、氰基乙酸丁酯、氰基乙酸甲酯、氰基乙酸2-乙基己酯、氰基乙酸月桂酯、氰基乙酸烯丙酯,和1,4-丁二醇双(氰基乙酸酯)。
7.根据权利要求1所述的洗涤剂添加剂,其中所述丙二酸酯选自由以下组成的组:丙二酸二乙酯、丙二酸二甲酯、丙二酸二丁酯、丙二酸双(2-乙基己基)酯、丙二酸二月桂酯,和丙二酸二烯丙酯。
8.根据权利要求1所述的洗涤剂添加剂,其中所述反应产物是在充当迈克尔催化剂的化合物存在下反应的。
9.根据权利要求8所述的洗涤剂添加剂,其中充当迈克尔催化剂的所述化合物是有机或无机碱。
10.根据权利要求8所述的洗涤剂添加剂,其中充当所述迈克尔催化剂的所述化合物选自由以下组成的组:1,1,3,3-四甲基胍、1,8-二氮杂双环[5.4.0]十一碳-7-烯、NaOH、KOH、K2CO3。
11.根据权利要求1到10中任一项所述的洗涤剂添加剂,其中所述洗涤剂添加剂中的所述活性物质的包封效率是60至100%。
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