JP6791981B2 - カルビノール官能トリシロキサンを含む洗剤組成物 - Google Patents
カルビノール官能トリシロキサンを含む洗剤組成物 Download PDFInfo
- Publication number
- JP6791981B2 JP6791981B2 JP2018555524A JP2018555524A JP6791981B2 JP 6791981 B2 JP6791981 B2 JP 6791981B2 JP 2018555524 A JP2018555524 A JP 2018555524A JP 2018555524 A JP2018555524 A JP 2018555524A JP 6791981 B2 JP6791981 B2 JP 6791981B2
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- detergent composition
- trisiloxane
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- reaction
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 178
- ZQTYRTSKQFQYPQ-UHFFFAOYSA-N trisiloxane Chemical compound [SiH3]O[SiH2]O[SiH3] ZQTYRTSKQFQYPQ-UHFFFAOYSA-N 0.000 title claims description 170
- 239000003599 detergent Substances 0.000 title claims description 156
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title claims description 28
- 125000000524 functional group Chemical group 0.000 claims description 53
- 239000004094 surface-active agent Substances 0.000 claims description 52
- 239000004593 Epoxy Substances 0.000 claims description 46
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 239000004615 ingredient Substances 0.000 claims description 20
- 125000003277 amino group Chemical group 0.000 claims description 17
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 15
- 239000002270 dispersing agent Substances 0.000 claims description 14
- 238000004140 cleaning Methods 0.000 claims description 13
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- 238000004851 dishwashing Methods 0.000 claims description 9
- 239000002736 nonionic surfactant Substances 0.000 claims description 8
- 239000003945 anionic surfactant Substances 0.000 claims description 7
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 5
- 150000002894 organic compounds Chemical class 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000000306 component Substances 0.000 description 137
- 238000006243 chemical reaction Methods 0.000 description 91
- -1 metalryl Chemical group 0.000 description 65
- 239000000463 material Substances 0.000 description 48
- 238000000034 method Methods 0.000 description 40
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000003054 catalyst Substances 0.000 description 29
- 238000006459 hydrosilylation reaction Methods 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 23
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- 239000007806 chemical reaction intermediate Substances 0.000 description 18
- 125000001183 hydrocarbyl group Chemical group 0.000 description 18
- 239000000126 substance Substances 0.000 description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 15
- 229910052801 chlorine Inorganic materials 0.000 description 15
- 239000002612 dispersion medium Substances 0.000 description 15
- 235000019441 ethanol Nutrition 0.000 description 15
- 229920000570 polyether Polymers 0.000 description 15
- 229920001451 polypropylene glycol Polymers 0.000 description 15
- 238000010926 purge Methods 0.000 description 15
- 229910052697 platinum Inorganic materials 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000004721 Polyphenylene oxide Substances 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 229920001296 polysiloxane Polymers 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- 229920002125 Sokalan® Polymers 0.000 description 11
- 239000007844 bleaching agent Substances 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 11
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 10
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000000499 gel Substances 0.000 description 9
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- LZDXRPVSAKWYDH-UHFFFAOYSA-N 2-ethyl-2-(prop-2-enoxymethyl)propane-1,3-diol Chemical compound CCC(CO)(CO)COCC=C LZDXRPVSAKWYDH-UHFFFAOYSA-N 0.000 description 7
- GCYHRYNSUGLLMA-UHFFFAOYSA-N 2-prop-2-enoxyethanol Chemical compound OCCOCC=C GCYHRYNSUGLLMA-UHFFFAOYSA-N 0.000 description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 7
- 229940043276 diisopropanolamine Drugs 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- SWGZAKPJNWCPRY-UHFFFAOYSA-N methyl-bis(trimethylsilyloxy)silicon Chemical compound C[Si](C)(C)O[Si](C)O[Si](C)(C)C SWGZAKPJNWCPRY-UHFFFAOYSA-N 0.000 description 7
- 239000000693 micelle Substances 0.000 description 7
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- 238000002360 preparation method Methods 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical group NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000004115 Sodium Silicate Substances 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000002015 acyclic group Chemical group 0.000 description 6
- 150000001412 amines Chemical group 0.000 description 6
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 238000006065 biodegradation reaction Methods 0.000 description 5
- 230000003247 decreasing effect Effects 0.000 description 5
- 239000003752 hydrotrope Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 238000007142 ring opening reaction Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 238000005292 vacuum distillation Methods 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000005708 Sodium hypochlorite Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 150000008051 alkyl sulfates Chemical class 0.000 description 4
- 238000004061 bleaching Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 239000013256 coordination polymer Substances 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
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- 239000004744 fabric Substances 0.000 description 4
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- 239000011976 maleic acid Substances 0.000 description 4
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- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 4
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 4
- 229910052911 sodium silicate Inorganic materials 0.000 description 4
- QUCDWLYKDRVKMI-UHFFFAOYSA-M sodium;3,4-dimethylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1C QUCDWLYKDRVKMI-UHFFFAOYSA-M 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 3
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- 239000010703 silicon Substances 0.000 description 3
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 3
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- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
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Images
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
- C11D3/162—Organic compounds containing Si
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- 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
- C11D1/02—Anionic compounds
-
- 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
-
- 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
- C11D1/83—Mixtures of non-ionic with anionic compounds
-
- 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
- C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
-
- 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
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Description
(R1 3SiO1/2)(R1R3SiO2/2)(R1 3SiO1/2) (I)
のものである。
トリシロキサンを含む洗剤組成物が提供される。洗剤組成物は、単に洗剤と呼ばれ得る。「洗剤」という用語は、一般的に、洗い及びクリーニングプロセスを意図されている、石鹸及び/若しくは他の界面活性剤を含有する任意の物質、組成物、製剤又は調製物を意味する。適切な洗剤組成物は、任意の形態(例えば液体、ゲル、粉末、ペースト、バー、ケーキ、成形片、造形品など)であってよく、家庭用、業務用、又は産業用の目的のために、市場に出されてよく、又はその目的で使用されてよい。
トリシロキサンは、洗剤添加剤と呼ばれ得る。多くの実施形態において、トリシロキサンは、欧州議会及び洗剤審議会の法令(EC)No.648/2004による要件を満たし、これは、EC No.907/2006及び551/2009を含めた、それに後続するあらゆる修正事項/添付書類と共に、参照により本明細書に組み込む。トリシロキサンは、概して、EC No.648/2004に従って定義される「界面活性剤」ではない。「界面活性剤」という用語は、具体的には、EC No.648/2004を参照すると、一般的には、表面活性を有し、水の表面張力の低下、並びに水/空気界面における拡散単層又は吸着単層の形成、並びにエマルション及び/又はマイクロエマルション及び/又はミセルの形成、並びに水−固体界面での吸着が可能な性質及び大きさの、1個以上の親水性、及び1個以上の疎水性基からなる洗剤に使用される任意の有機物質及び/又は調製物と定義される。この点において、追加の態様は、以下の実施例のセクションを参照して認識され得る。
成分(A)は、ペンダントケイ素結合官能基を有する。ペンダントケイ素結合官能基は、一般的に、水素原子、エポキシ含有基、エチレン性不飽和基及びアミン基から選択される。「ペンダント」ケイ素結合官能基は、トリシロキサンのDユニットに連結する。
(R1 3SiO1/2)(R1R2SiO2/2)(R1 3SiO1/2) (A1)
のものである。
成分(B)は、少なくとも1個のヒドロキシル(−OH)官能基を有する。ヒドロキシル官能基は、成分(A)に関して一般的に不活性である。「一般的に不活性」は、ヒドロキシル官能基(複数可)の反応が意図されていないことを意味する。具体的には、ヒドロキシル官能基は、例えばSi−H基と反応性であるが、反応は、トリシロキサンの形成中に最小化される、又は一般的に避けられ、その結果、すべてのヒドロキシル基の大多数が遊離したままである。成分(B)のヒドロキシル官能基(複数可)は、当業界で理解されている方法により、例えば、反応条件の管理、添加の順序、一時的なブロッキング/キャッピングなどにより、トリシロキサンの形成中の副反応から保護され得る。トリシロキサンのカルビノール官能基(複数可)は、典型的には、トリシロキサンのDユニットに連結し、一般的には、少なくとも成分(B)のヒドロキシル官能基(複数可)、任意選択で、開いたエポキシ環(エポキシ環は、成分(A)及び(B)の反応前に存在する)により付与される。ヒドロキシル官能基(複数可)は、末端及び/又はペンダント(トリシロキサンのDユニットから吊り下がった基/部分に対する)であってよい。
様々な実施形態において、トリシロキサンは、以下の一般式(I):
(R1 3SiO1/2)(R1R3SiO2/2)(R1 3SiO1/2) (I)
のものである。
トリシロキサンを形成する方法も提供される。この方法は、1)成分(A)を準備するステップ、及び2)成分(B)を準備するステップを含む。この方法は、3)成分(A)及び(B)を反応させて、トリシロキサンを形成するステップを更に含む。成分(A)及び(B)は、上に記載されている通りである。成分(A)及び(B)のそれぞれを、得ることができる、又は形成することができる。例えば、成分(A)及び(B)の一方又は両方は、化学物質の供給業者、例えばMidland、MIのDow Corningから商業的に得られる。そうでなければ、成分(A)及び(B)の一方又は両方は、それぞれの出発原料から形成できる。
例えばSi−Hとエチレン性不飽和基の間のヒドロシリル化(又は添加)反応は、典型的には、(C)ヒドロシリル化触媒の存在下で起こる。ヒドロシリル化触媒は、当技術分野の従来のものであってよい。例えば、ヒドロシリル化触媒は、白金族金属を含有する触媒であってよい。「白金族」は、ルテニウム、ロジウム、パラジウム、オスミウム、イリジウム及び白金、並びにそれらの錯体を意味する。本明細書において有用なヒドロシリル化触媒の非限定的な例は、米国特許第3,159,601号、第3,220,972号、第3,296,291号、第3,419,593号、第3,516,946号、第3,715,334号、第3,814,730号、第3,923,705号、第3,928,629号、第3,989,668号、第5,036,117号、第5,175,325号及び第6,605,734号に記載されており、そのそれぞれは、開示されているヒドロシリル化触媒に関して参照することにより、本明細書に組み込む。
トリシロキサン及び/又はそれらの成分は、典型的には、(D)分散媒中に形成される、及び/又は得られる。適切な分散媒(又は担体、希釈剤、溶媒又はビヒクル)は、直鎖状及び環状両方のシリコーン、有機油、有機溶媒並びにそれらの混合物を含む。溶媒の具体的な例は、米国特許第6,200,581号で見出すことができ、これは、この目的のために参照することにより本明細書に組み込む。様々な実施形態において、分散媒は、揮発性シロキサン、有機溶媒又はそれらの組み合わせを含む。
洗剤組成物は、様々な用途に利用され得、一般的には、特定の用途に限定されない。例えば、洗剤組成物は、食器洗い用洗剤組成物(例えば自動食器洗い用(auto dishwashing detergent、ADW)洗剤組成物)、洗濯洗剤組成物、染着除去/前処理組成物又は硬質表面用洗剤組成物(例えば自動車ケア用洗剤)であってよい。更なる洗剤用途は:個人用ケア及び個人用クレンジング製品(例えばボディウォッシュ、シャンプー及びコンディショナー)、食器手洗い用、自動食器洗い用及び食器洗い用添加剤を含む食器洗い用製品、洗濯洗剤(例えば手洗い用/自動洗濯機用洗剤)、織物柔軟剤、カーペットクリーナー及び洗濯助剤(例えばしみ及び染着除去剤)を含む洗濯ケア製品、多目的クリーナー、オーブン、窓/ガラス、金属、台所、床、浴室面のクリーナー、デスケーラー、排水管洗浄剤、精練剤、家庭用殺菌剤/消毒剤、並びに家庭用ケアワイプ及びフロアクリーニングシステムを含む表面ケア製品と、トイレ用ケアのためのシスタン内デバイス、リムブロック及び液体、並びに液体、フォーム、ゲル及びタブレットを含むトイレ用ケア製品が挙げられる。
洗剤組成物は、様々な方法により形成され得る。典型的には、洗剤組成物は、単に、すべての成分を一緒に組み合わせること、例えば混合することにより形成される。洗剤組成物は、特定の製造方法に一切限定されない。当業者は、特定の洗剤組成物、形態及び/又はそれらの最終使用に基づき、適切な製造方法を容易に決定できる。
13.29gのヘプタメチルトリシロキサン(98%、TCI America)及び20gのトルエン(≧99.5%、Fisher Scientific)を、窒素パージ下で反応フラスコに添加し、電磁撹拌機で混合した。混合物を、窒素パージ下で保持し、40℃に加熱した。シリンジに、7.87gの2−アリルオキシエタノール(98%、Aldrich)を充填し、シリンジポンプに入れた。一旦40℃にて、2−アリルオキシエタノールを、〜250μL/分で反応に計量供給した。〜5%の2−アリルオキシエタノールを添加した後で、ヘキサメチルジシロキサン中の108.8μLの1%白金錯体を添加した。反応物は最初に発熱し、残りの2−アリルオキシエタノールを添加すると、59.5℃の最高温度に到達した。合計6.82gの2−アリルオキシエタノールを添加した。反応を60℃にて3時間保ち、次いで冷却した。
10.75gのヘプタメチルトリシロキサン(98%、TCI America)及び20gのトルエン(≧99.5%、Fisher Scientific)を、窒素パージ下で反応フラスコに添加し、電磁撹拌機で混合した。混合物を、窒素パージ下で保持し、40℃に加熱した。シリンジに、11.37gのトリメチロールプロパンアリルエーテル(98%、Aldrich)を充填し、シリンジポンプに入れた。一旦40℃にて、トリメチロールプロパンアリルエーテルを、〜250μL/分で反応に計量供給した。〜5%のトリメチロールプロパンアリルエーテルを添加した後で、87.9μLのヘキサメチルジシロキサン中の1%白金錯体を添加した。反応物は最初に発熱し、残りのトリメチロールプロパンアリルエーテルを添加すると58.9℃の最高温度に到達した。合計9.44gのトリメチロールプロパンアリルエーテルを添加した。反応を60℃にて3時間保ち、次いで冷却した。
125.58gの1,1,1,3,5,5,5−ヘプタメチルトリシロキサン(BisH)、22.5gのアリルグリセロール及び168gのイソプロピルアルコール(isopropyl alcohol、IPA)を、窒素パージ下で反応フラスコに添加し、かき混ぜ機で混合した。混合物を、窒素パージ下で保持し、70℃に加熱した。0.3gのヘキサメチルジシロキサン/IPA中の1.1%白金錯体を添加した。反応物は最初に発熱した。25.2gのアリルグリセロール、16.8gのIPA、及び0.3gのヘキサメチルジシロキサン/IPA中の1.1%白金錯体を、第2のステップとして添加した。25.2gのアリルグリセロール、12.6gのIPA、及び0.3gのヘキサメチルジシロキサン/IPA中の1.1%白金錯体を、第3のステップとして添加した。16.8gのアリルグリセロール、12.6gのIPA、及び0.209gのヘキサメチルジシロキサン/IPA中の1.1%白金錯体を、第4のステップとして添加した。合計89.7gのアリルグリセロールを合計125.58gのBisHに対して添加した。反応を70℃にて6時間保ち、次いで冷却した。
12.096gのBisH及び20.00gのIPAを、窒素パージ下で、反応フラスコ中において混合し、40℃に加熱した。シリンジに、7.904gのアリルグリセロールを充填し、次いでシリンジポンプに入れた。一旦40℃にて、アリルグリセロールを、669μL/分で反応に計量供給した。〜5%のアリルグリセロールを添加した後で、ヘキサメチルジシロキサン中のKarstedt触媒の1%溶液(98.98μL)を添加して、18ppm Pt触媒を得た。反応物を発熱させ、アリルグリセロールをすべて添加した後で60℃に冷却した。次いで、反応を60℃にて3時間保ち、次いで冷却した。
71.22gのBisH及び43.78gのアリルグリシジルエーテル(allyl glycidyl ether、AGE)を、窒素パージ下で、反応フラスコ中において混合し、60℃に加熱した。一旦60℃にて、この溶液(24.42μL)にIPA中のKarstedt触媒の1%溶液を添加して、8ppm Ptを得た。反応物を発熱させ、75℃に冷却した。反応を、75℃にて3時間保ち、次いで冷却した。
実施例5で生成された83.430gのエポキシ官能トリシロキサン中間体、26.056gのジエタノールアミン(DEA)及び30.000gのIPAを、反応フラスコに添加した。反応は、反応溶液越しに窒素パージを使用して、不活性雰囲気中で行った。次いで、反応を75℃に加熱し、これらの条件で完了まで保った。
実施例5で生成された、65.849gのエポキシ官能トリシロキサン中間体、26.052gのジイソプロパノールアミン(DIPA)、及び30.000gのIPAを、反応フラスコに添加した。反応は、反応溶液越しに窒素パージを使用して、不活性雰囲気中で行った。次いで、反応を75℃に加熱し、これらの条件で完了まで保った。
56.81gのBisH及びアリルジグリセロールの合計(合計71.19g)の半分を、窒素パージ下で反応フラスコ中において混合し、45℃に加熱した。一旦45℃にて、IPA中の1%溶液のKarstedt触媒(25.48μL)を添加して、8ppm Ptを得た。反応物を発熱させ、80℃に冷却した。アリルジグリセロールのもう半分を反応溶液に添加した。一旦、反応を再度発熱し、70℃に冷却した。次いで、反応を70℃にて4時間保ち、次いで、冷却した。
9.739gのアリルキシリトール及び20.017gのIPAを、窒素パージ下で、反応フラスコ中において混合し、50℃に加熱した。シリンジに、10.261gのBisHを充填し、次いでシリンジポンプに入れた。一旦50℃にて、BisHを881μL/分で反応に計量供給した。〜5%のBisHを添加した後で、ヘキサメチルジシロキサン中のKarstedt触媒の1%溶液(83.96μL)を添加して、16ppm Ptを得た。反応物を発熱させ、すべてのBisHを添加した後で、60℃に冷却した。次いで、反応を、60℃にて3時間保ち、次いで冷却した。
実施例5で生成された5.516gのエポキシ官能トリシロキサン中間体、1.984gのトリス(ヒドロキシメチル)アミノメタン(トリス)、5.250gのメタノール及び12.250gのIPAを、反応フラスコに添加した。反応は、反応溶液越しに窒素パージを使用して、不活性雰囲気中で行った。次いで、反応を75℃に加熱し、反応が完了するまでこれらの条件で保った。
実施例5で生成された15.824gのエポキシ官能トリシロキサン中間体、9.176gのn−メチルグルカミン(n−methylglucamine、NMG)、8.750gのメタノール及び16.250gのIPAを、反応フラスコに添加した。反応は、反応溶液越しに窒素パージを使用して、不活性雰囲気中で行った。次いで、反応を75℃に加熱し、反応が完了するまでこれらの条件で保った。
12.855gのAGE、12.500gのDIPA及び24.645gのトルエンを、反応フラスコに添加した。反応は、反応溶液越しに窒素パージを使用して、不活性雰囲気中で行った。次いで、反応を75℃に加熱し、これらの条件で完了まで保った。
1.2594gのBisH、実施例12で生成された1.266gのアリルAGE−DIPA材料、及び2.052gのIPAは、窒素パージ下で、反応フラスコ中において混合し、60℃に加熱した。一旦60℃にて、この溶液に、ヘキサメチルジシロキサン中のKarstedt触媒の1%溶液(20.26μL)を添加して、30ppm Ptを得た。反応物を発熱させ、70℃に冷却した。次いで、反応は70℃にて完了まで保った。
10.3gのアリルソルビトール及び20.017gのIPAは、窒素パージ下で、反応フラスコ中において混合し、50℃に加熱する。シリンジに、10.3gのBisHを充填し、次いでシリンジポンプに入れる。一旦50℃にて、BisHを反応容器に881μL/分で計量供給する。〜5%のBisHを添加した後で、ヘキサメチルジシロキサン中のKarstedt触媒の1%溶液(83.96μL)を添加して、16ppm Ptを得る。反応物を発熱させ、BisHのすべてを添加した後で、60℃に冷却する。次いで、反応を60℃にて3時間保ち、次いで冷却する。
トリシロキサンポリエーテル材料を含む様々なトリシロキサン材料を、EUの洗剤に関する指示(「指示」、EC No.648/2004)の観点において研究した。多くのトリシロキサンポリエーテル材料、とりわけ高レベルのポリエチレンオキシドを含有するものは、指示によれば「界面活性剤」として分類可能であったことが見出された。したがって、そのような界面活性剤は、この指示の対応する生分解性要件により制限を受ける。対照的に、他のトリシロキサン材料は、この指示によれば分類可能な界面活性剤の範囲外になることが見出された。したがって、そのような「非界面活性剤」は、一般的には、非水溶性流体である、又は水中で固体微粒子を形成するとみなされ、それ自体は、この指示の対応する生分解性要件により制限を受けない。このように、ある非界面活性トリシロキサンは、欧州では洗剤組成物として利用されるが、その理由は、このトリシロキサンが指示に従っているためである。
1)水中に材料が0.5重量%の濃度で、水の表面張力を≦45ダイン/cmに低下させること(又は≦45mN/m)、
2)空気/水界面において拡散又は吸着単層を形成すること、
3)エマルション、マイクロエマルション及び/又はミセルを形成すること、
4)並びに水/固体界面で吸着することが可能である材料と定義されていた。
Claims (10)
- 少なくとも1個のカルビノール官能基を有するトリシロキサンを含む洗剤組成物であって、前記トリシロキサンが、
(A)エポキシ含有基であるペンダントケイ素結合官能基を有する初期トリシロキサンと
(B)成分(A)の前記ペンダントケイ素結合官能基と反応性の官能基及び少なくとも1個のヒドロキシル官能基を有する有機化合物との反応生成物を含み、
成分(A)が、水素原子、エポキシ含有基、エチレン性不飽和基及びアミン基から選択される末端ケイ素結合官能基を含まず、
成分(A)が、ポリオキシアルキレン基を含まず、
成分(A)が、以下の一般式(A1):
(R 1 3 SiO 1/2 )(R 1 R 2 SiO 2/2 )(R 1 3 SiO 1/2 ) (A1)、
(式中、各R 1 は、独立して選択されるC 1 〜C 6 アルキル基であり、R 2 が、上で定義されている前記ペンダントケイ素結合官能基である)のものであり、
前記トリシロキサンが、100重量部の前記洗剤組成物を基準として、0.001〜20重量部の量で存在し、
成分(B)が、以下の成分(B7)〜(B9):
- 成分(B)が、成分(B8)である、請求項1に記載の洗剤組成物。
- R 3 が(ii)の基である、請求項3に記載の洗剤組成物。
- 各R 1 がメチル基である、請求項1〜3のいずれか一項に記載の洗剤組成物。
- 少なくとも1つの分散剤を更に含む、任意選択でプロピレングリコールを更に含む、請求項1〜5のいずれか一項に記載の洗剤組成物。
- 前記分散剤が、100重量部の洗剤組成物を基準として、0.01〜50重量部の量、任意選択で0.1〜40重量部の量で存在する、請求項6に記載の洗剤組成物。
- 水を更に含み、水性洗剤組成物と更に定義される、請求項1〜7のいずれか一項に記載の洗剤組成物。
- 少なくとも1つの界面活性剤を更に含む、任意選択で少なくとも1つのアニオン性界面活性剤及び少なくとも1つの非イオン性界面活性剤を更に含む、請求項1〜8のいずれか一項に記載の洗剤組成物。
- 食器洗い用洗剤組成物、洗濯洗剤組成物、染着除去/前処理組成物又は硬質表面用クリーニング組成物と更に定義される、任意選択で自動食器洗い用(ADW)洗剤組成物と更に定義される、請求項1〜9のいずれか一項に記載の洗剤組成物。
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- 2017-04-26 CN CN201780033525.7A patent/CN109196085B/zh active Active
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EP3448974B1 (en) | 2021-07-07 |
US10829718B2 (en) | 2020-11-10 |
CN109196085A (zh) | 2019-01-11 |
US20190112549A1 (en) | 2019-04-18 |
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WO2017189703A1 (en) | 2017-11-02 |
EP3448974A1 (en) | 2019-03-06 |
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