CN107207722B - 具有低熔点的聚醚胺 - Google Patents
具有低熔点的聚醚胺 Download PDFInfo
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- CN107207722B CN107207722B CN201680007090.4A CN201680007090A CN107207722B CN 107207722 B CN107207722 B CN 107207722B CN 201680007090 A CN201680007090 A CN 201680007090A CN 107207722 B CN107207722 B CN 107207722B
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- China
- Prior art keywords
- substituted
- polyetheramines
- polyetheramine
- alkylene
- independently selected
- 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.)
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- 238000002844 melting Methods 0.000 title claims abstract description 12
- 230000008018 melting Effects 0.000 title claims abstract description 12
- 239000000203 mixture Substances 0.000 claims abstract description 44
- 150000001412 amines Chemical class 0.000 claims abstract description 30
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 18
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- 238000009472 formulation Methods 0.000 claims abstract description 8
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims abstract description 7
- 239000002537 cosmetic Substances 0.000 claims abstract description 5
- 239000010779 crude oil Substances 0.000 claims abstract description 5
- 239000006185 dispersion Substances 0.000 claims abstract description 4
- 239000000049 pigment Substances 0.000 claims abstract description 4
- 230000019635 sulfation Effects 0.000 claims description 18
- 238000005670 sulfation reaction Methods 0.000 claims description 18
- 238000005956 quaternization reaction Methods 0.000 claims description 17
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- -1 1, 2-propylene, 1, 2-butylene Chemical group 0.000 claims description 9
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 8
- 229920000570 polyether Polymers 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- SYURNNNQIFDVCA-UHFFFAOYSA-N 2-propyloxirane Chemical compound CCCC1CO1 SYURNNNQIFDVCA-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 238000009713 electroplating Methods 0.000 claims description 2
- 230000026731 phosphorylation Effects 0.000 claims description 2
- 238000006366 phosphorylation reaction Methods 0.000 claims description 2
- 230000005588 protonation Effects 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000005156 substituted alkylene group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 9
- 239000003973 paint Substances 0.000 abstract description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000004140 cleaning Methods 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000004094 surface-active agent Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000009833 condensation Methods 0.000 description 7
- 230000005494 condensation Effects 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 230000001180 sulfating effect Effects 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
Classifications
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- 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
- C08G65/2618—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 nitrogen
- C08G65/2621—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 nitrogen containing amine groups
- C08G65/2624—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 nitrogen containing amine groups containing aliphatic amine groups
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D17/00—Separation of liquids, not provided for elsewhere, e.g. by thermal diffusion
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- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/322—Polymers modified by chemical after-treatment with inorganic compounds containing hydrogen
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- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
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- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G33/00—Dewatering or demulsification of hydrocarbon oils
- C10G33/04—Dewatering or demulsification of hydrocarbon oils with chemical means
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- 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
- C11D1/38—Cationic compounds
- C11D1/42—Amino alcohols or amino ethers
- C11D1/44—Ethers of polyoxyalkylenes with amino alcohols; Condensation products of epoxyalkanes with amines
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- C08G2650/30—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type branched
- C08G2650/32—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type branched dendritic or similar
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- C08G2650/50—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing nitrogen, e.g. polyetheramines or Jeffamines(r)
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- Chemical & Material Sciences (AREA)
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- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
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Abstract
本发明涉及具有低熔点的取代聚醚胺，其可以通过使至少两种N‑(羟基烷基)胺缩合以得到聚醚胺并随后使所述聚醚胺的至少一个剩余羟基和/或若存在的话，至少一个仲氨基与氧化乙烯和至少一种其他氧化烯反应以得到取代聚醚胺而得到。本发明还涉及该类取代聚醚胺在化妆品配制剂领域中，作为原油破乳剂，在喷墨颜料分散体中，在电泳漆中或在水泥质组合物中的用途以及其中所述取代聚醚胺在所述领域中使用的方法。
Description
本发明涉及具有低熔点的取代聚醚胺，其可以通过使至少两种N-(羟基烷基)胺缩合以得到聚醚胺并随后使所述聚醚胺的至少一个剩余羟基和/或若存在的话，至少一个仲氨基与氧化乙烯和至少一种其他氧化烯反应以得到取代聚醚胺而得到。本发明还涉及该类取代聚醚胺在化妆品配制剂领域中，作为原油破乳剂(crude oil emulsion braker)，在喷墨颜料分散体中，在电泳漆中或在水泥质组合物中的用途以及其中所述取代聚醚胺在所述领域中使用的方法。
在WO 2009/060060中描述了烷氧基化聚链烷醇胺。该类聚链烷醇胺被描述为可以通过链烷醇胺的缩合得到。在WO 2009/060060中，将聚链烷醇胺用氧化乙烯(EO)、氧化丙烯(PO)、氧化丁烯(BuO)、氧化戊烯(PeO)、氧化己烷(HeO)或氧化苯乙烯烷氧基化。聚链烷醇胺被描述为与1-100mol至少一种氧化烯反应，后者又与在缩合反应中得到的聚醚的1mol剩余羟基以及若存在的话，仲氨基反应。聚链烷醇胺如WO 2009/060060或如US20140014004所述由链烷醇胺得到。
WO 2011/032640描述了通过链烷醇胺的碱催化得到并用1-200个C2-C4氧化烯/羟基烷氧基化的聚链烷醇胺。
聚醚胺的乙氧基化物如乙氧基化聚-三乙醇胺(聚TEA)在洗涤组合物中例如对矿物污垢(如粘土)呈现分散效果。该类产品的缺点是它们在室温下为固体(蜡状)且必须熔融或稀释以进一步加工。然而，用水稀释该类产品不仅涉及活性物质含量降低的缺点，而且涉及将水放入该洗涤组合物中的缺点。该水含量可能例如在洗涤组合物的单剂量(SUD)规格中是特别不希望的。
这一和其他技术问题通过如本文所述且如权利要求书中所定义的本发明克服。
本发明涉及取代的聚醚胺，其可以按如下得到：
(a)使至少两种N-(羟基烷基)胺缩合，其中所述N-(羟基烷基)胺分别独立地选自式Ia和Ib的N-(羟基烷基)胺：
其中
A独立地选自线性或支化C1亚烷基、C2亚烷基、C3亚烷基、C4亚烷基、C5亚烷基和C6亚烷基；
R3、R3*、R4、R4*、R5、R5*、R6、R6*、R7、R7*和R8独立地选自H；
取代或未取代的线性或支化烷基；取代或未取代的环烷基；以及取代或未取代的芳基，
得到聚醚胺；以及
(b)使在(a)中得到的聚醚胺的至少一个剩余羟基和/或若存在的话，至少一个仲氨基与氧化乙烯和至少一种选自氧化丙烯、氧化丁烯和氧化戊烯的其他氧化烯反应，
得到被至少一个亚烷氧基单元E取代的取代聚醚胺，
其中E为式II的亚烷氧基单元：
其中
R1独立地选自1,2-亚丙基、1,2-亚丁基和1,2-亚戊基；
R2独立地选自H、C1-C22烷基中的任一个和C7-C22芳烷基中的任一个；
m为独立地选自范围内的值的整数5-18；
n为独立地选自范围内的值的整数1-5；以及
p为独立地选自范围内的值的整数2-14。
正如本发明中惊人地发现的那样，在聚醚胺的亚烷氧基单元内氧化丙烯(PO)、氧化丁烯(BuO)或氧化戊烯(PeO)的内嵌段能够降低该聚醚胺的熔点。在本发明的一个实施方案中，在聚醚胺的亚烷氧基单元内氧化丙烯(PO)、氧化丁烯(BuO)或氧化戊烯(PeO)的该内嵌段能够将聚醚胺的熔点降至室温(例如20℃)以下。也就是说，本发明聚醚胺可以具有低于30℃，优选低于25℃，更优选低于22℃，更优选低于20℃，更优选低于18℃，更优选低于16℃，最优选低于15℃的熔点(在1巴环境压力下)。此外，已经惊人地发现该类含有PO-、BuO-或PeO-的聚醚胺在洗涤组合物中呈现所需分散效果。
在本发明的一个实施方案中，该聚醚胺通过主要缩合式Ia的N-(羟基烷基)胺且不缩合或者很少缩合式Ib的N-(羟基烷基)胺而制备，式Ia的N-(羟基烷基)胺与式Ib的N-(羟基烷基)胺在100:0-0:100，优选85:15，最优选100:0内变化。在本发明的一个实施方案中，该聚醚胺通过缩合式Ia的N-(羟基烷基)胺而不缩合式Ib的N-(羟基烷基)胺而制备。
对于待按照本发明缩合的式Ia或Ib的N-(羟基烷基)胺，A可以独立地选自线性或支化的C1亚烷基、C2亚烷基、C3亚烷基、C4亚烷基、C5亚烷基和C6亚烷基。所述线性或支化的亚烷基可以被取代或未被取代，优选它们未被取代。在本发明的一个实施方案中，A主要(优选至少或大于98％)或仅由C1亚烷基或C2亚烷基，优选C1亚烷基构成。此外，在一个实施方案中R3*、R4*、R5*、R6*和R7*为H且R3、R4、R5、R6、R7为H或甲基。因此，在本发明的一个实施方案中，待根据本发明缩合的N-(羟基烷基)胺主要(优选至少或大于85％，更优选至少或大于98％)为三乙醇胺或者仅为三乙醇胺和/或三异丙醇胺，优选三乙醇胺。
通常而言，除非本文另有说明，术语“取代的”是指特定基团的H原子可以被取代。也就是说，例如若提到“取代的烷基”，则所述烷基的H原子相应地可以被取代，而不是整个烷基本身。这经适当改变之后同样适用于如本文所述可以被取代的其他基团。
对于待按照本发明缩合的式Ia或Ib的N-(羟基烷基)胺，R3、R3*、R4、R4*、R5、R5*、R6、R6*、R7、R7*和R8可以独立地选自H；取代或未取代的线性或支化烷基；取代或未取代的环烷基；以及取代或未取代的芳基。就此而言，所述取代烷基例如可以被羟基、卤素、氰基或C1-C4烷氧基取代，并且所述取代环烷基和芳基例如可以被羟基、卤素、氰基、C1-C4烷基或C1-C4烷氧基取代。在本发明的一个实施方案中，R3、R3*、R4、R4*、R5、R5*、R6、R6*、R7和R7*中任一个或全部相互独立地为H、甲基或乙基，优选H或甲基。在另一实施方案中，R8选自H、甲基、乙基和丁基。
如本文所述且待按照本发明进行的缩合(步骤(a))可以如熟练技术人员已知的那样且例如如EP 0441198、US 5,939,463或WO 2014/012812所述进行。如本文所述且待按照本发明进行的烷氧基化(步骤(b))可以如熟练技术人员已知的那样且例如如WO 2009/060060所述进行。
根据本发明，在缩合步骤(a)之后，在步骤(b)中使在步骤(a)中的所述缩合之后得到的聚醚胺的至少一个剩余羟基和/或若存在的话，至少一个仲氨基与氧化乙烯(EO)和至少一种选自PO、BuO和PeO的其它氧化烯反应。正如熟练技术人员易于知晓的，在N-(羟基烷基)胺根据步骤(a)缩合之后，总是留下至少一个羟基，除非在长的反应时间内使用极高温度。然而，在其中在长的反应时间内使用该极高温度的后一情况下，将得到再也不能处理的固体物质。此外，也易于为熟练技术人员所理解的是，若根据本发明缩合式Ib化合物且至少一个R8选择为H，则可以存在所述至少一个仲氨基。在本发明的一个实施方案中，待与在缩合步骤(a)之后得到的聚醚胺反应的选自PO、BuO和PeO的所述氧化烯为1,2-氧化烯，即选自1,2-PO、1,2-BuO和1,2-PeO。在本发明的另一实施方案中，待与所述聚醚胺反应的所述氧化烯为1,2-PO。
因此，在本发明的一个实施方案中，式II的亚烷氧基单元的R1可以为1,2-亚丙基。在本发明的另一实施方案照中，对于式II的亚烷氧基单元的R2，可以选择H或C1-C4烷基，优选H。
在本发明的一个实施方案中，关于亚烷氧基单元E，m可以为7-14，优选8-12，更优选10-12。在本发明的另一实施方案照中，n可以为1-5，优选1-3，更优选2-3。在本发明的另一实施方案照中，p可以为5-12，优选6-11，更优选8-9。在本发明的一个实施方案中，亚烷氧基单元E的总长度m+n+p可以为15-30，优选18-24。
就本发明而言，可以如本文所述得到的取代聚醚胺可以由在本领域中已知且如本文所述的方法通过季化、质子化、硫酸化、转移硫酸化和/或磷酸化进一步改性。在本发明的一个实施方案中，该取代聚醚胺通过季化或具有额外转移硫酸化的季化改性。季化例如可以用烷基进行。季化程度就此而言例如可以高达100％，优选10-95％。
为了调节本发明的取代聚醚胺以适合本文所述的特定用途，例如用于其中要使用它们的化妆品组合物，并实现该配制剂的更好相容性和/或相稳定性，季化可能是有利的。
本发明取代聚醚胺的季化例如可以通过引入C1-C22烷基、C1-C4烷基和/或C7-C22芳烷基、芳基或烷芳基而实现并且可以通过与相应烷基卤化物、芳烷基卤化物和硫酸二烷基酯反应而以常规方式进行，例如如WO 2009/060059所述。
季化例如可以通过使本发明的取代聚醚胺与烷基化剂如C1-C4烷基卤化物，例如溴甲烷、氯甲烷、氯乙烷、碘甲烷、正丁基溴、异丙基溴，或者与芳烷基卤化物，例如苄基氯、苄基溴，或者与硫酸二-C1-C22烷基酯在碱存在下，尤其是与硫酸二甲酯或硫酸二乙酯反应而实现。合适的碱例如为氢氧化钠和氢氧化钾。
烷基化剂的量决定了该聚合物中氨基的季化量，即季化结构部分的量。
季化结构部分的量可以由非季化胺和季化胺中的胺值差计算。
胺值可以根据DIN 16945中所述方法测定。
该反应可以在没有溶剂下进行。然而，可以使用溶剂或稀释剂如水、乙腈、二甲亚砜、N-甲基吡咯烷酮等。反应温度可以为10-150℃，优选50-100℃。
在一个实施方案中，若式II中的R2为H，本发明季化或未季化的取代聚醚胺可以(额外地)硫酸化或转移硫酸化。例如，本发明季化的取代聚醚胺可以硫酸化或转移硫酸化。季化的取代聚醚胺可以按照本领域已知的方法，例如如WO 2005/092952所述硫酸化或转移硫酸化。硫酸化或转移硫酸化例如可以用硫酸二甲酯实现。
本发明聚合物的硫酸化可以通过与硫酸或硫酸衍生物反应而进行。合适的硫酸化剂例如包括硫酸(优选浓度为75-100％，更优选浓度为85-98％)、发烟硫酸、SO3、氯磺酸、磺酰氯、氨基硫酸等。若将磺酰氯用作硫酸化剂，则剩余的氯在硫酸化之后通过水解被置换。硫酸化剂可以以等摩尔量或过量使用，例如以1-1.5mol/该聚合物中存在的OH基团使用。然而，硫酸化剂还可以以不足等摩尔量使用。硫酸化可以在溶剂存在下进行。合适的溶剂例如包括甲苯。在硫酸化之后，可以以本领域已知的常规方式中和并后处理反应混合物。
如上所述，还可以季化并转移硫酸化可以按照本发明得到的取代聚醚胺。硫酸化方法可以描述为转移硫酸化方法，其中烷氧基化多胺或烷氧基化聚亚烷基亚胺首先与硫酸二-C1-C4烷基酯反应而形成季化多胺和作为抗衡离子的硫酸化物质，然后使羟基与硫酸化物质反应，导致季化和硫酸化。转移硫酸化方法的实例尤其描述于WO 2004/024858或WO2002/012180中。
组合的季化和硫酸化例如可以通过首先使取代聚醚胺与硫酸二-C1-C4烷基酯在碱存在下反应，然后例如用羧酸如甲磺酸或用无机酸如磷酸、磷酸或盐酸酸化由季化得到的反应混合物而实现。该过程可以在pH小于6，优选pH小于3下在0-200℃，优选50-150℃的温度下进行。在转移硫酸化之后，可以如本领域已知那样中和反应混合物。
本发明进一步涉及可以根据本发明得到的取代聚醚胺在化妆品配制剂中，作为原油破乳剂，在喷墨颜料分散体中，在电镀中或者在水泥质组合物中的用途。在本文中还描述且例举了可以根据本发明得到的取代聚醚胺在洗涤和清洁组合物中的用途。
本文所用术语“清洁组合物”包括设计用于清洁染污材料的组合物和配制剂。该类组合物包括但不限于洗衣清洁组合物和洗涤剂、织物软化组合物、织物增强组合物、织物清新组合物、洗衣预洗剂、洗衣预处理剂、洗衣添加剂、喷雾产品、干清洁剂或组合物、洗衣漂洗添加剂、洗涤添加剂、漂洗后织物处理剂、熨烫助剂、洗碟组合物、硬表面清洁组合物、单位剂量配制剂、延迟释放配制剂、含于多孔基材或非织造片材之上或之中的洗涤剂以及鉴于本文的教导可以为本领域熟练技术人员明了的其他合适形式。该类组合物可以用作预洗衣处理剂、洗衣后处理剂，或者可以在洗衣操作的漂洗或洗涤循环过程中加入。清洁组合物可以具有选自液体、粉末、单相或多相单位剂量、小袋、片剂、凝胶、糊、条或薄片的形式。
清洁组合物以足以提供所需清洁性能的量包含表面活性剂体系。在一些实施方案中，该清洁组合物基于该组合物的重量包含约1-70％表面活性剂体系。在其他实施方案中，该液体清洁组合物基于该组合物的重量包含约2-60％表面活性剂体系。在其他实施方案中，该液体清洁组合物基于该组合物的重量包含约5-30％表面活性剂体系。该表面活性剂体系可以包含选自阴离子表面活性剂、非离子表面活性剂、阳离子表面活性剂、两性离子表面活性剂、两性表面活性剂、两性表面活性剂及其混合物的洗涤表面活性剂。本领域普通技术人员应理解的是洗涤表面活性剂包括对染污材料提供清洁、去污或洗衣益处的任何表面活性剂或表面活性剂混合物。
下列实施例说明本文提供和描述的发明且不能理解为将本发明限制到实施例中所述参数和实施方案。
实施例
在实施例中使用下列缩写：
EO 氧化乙烯
PO 氧化丙烯
x EO/OH x摩尔氧化乙烯/摩尔聚醚胺中的羟基
y PO/OH y摩尔氧化丙烯/摩尔聚醚胺中的羟基
根据DIN 51007用来自Mettler Toledo的差示扫描量热法823/700/229测定熔点。
实施例1：聚三乙醇胺+11EO/OH+2PO/OH+8EO/OH
1(a)聚三乙醇胺
向装有搅拌器、蒸馏桥、气体入口管和内部温度计的四颈烧瓶中加入1500g三乙醇胺和20g 50重量％H3PO2水溶液。将该混合物在氮气下加热至200℃。将反应混合物在200℃下搅拌15.5小时，其间借助温和N2气流汽提气体经由蒸馏桥除去该反应中形成的缩合物。在所示反应时间结束时降温至140℃。在100毫巴的压力下除去残留低分子量产物。然后将反应混合物冷却至环境温度，得到聚三乙醇胺(OH值：585mg KOH/g，胺值：423mg KOH/g，在60℃下的动态粘度：431mPas，Mn＝4450g/mol，Mw＝8200g/mol。分子量通过使用折光仪作为检测器的凝胶渗透色谱法测定。所用移动相为六氟异丙醇(HFIP)，用于测定分子量的标样是聚甲基丙烯酸甲酯(PMMA)。
1(b)聚三乙醇胺+11EO/OH+2PO/OH+8EO/OH
在2L高压釜中混合90.0g在实施例1(a)中得到的聚三乙醇胺和3.9g氢氧化钾(50％水溶液)并在真空(<10毫巴)和120℃下搅拌2小时。将该高压釜用氮气吹扫并加热至140℃。在5小时内加入453.8g氧化乙烯，然后在1小时内加入108.7g氧化丙烯以及随后在3小时内加入330.0g氧化乙烯。为了使该反应完全，使该混合物在下额外后反应10小时140℃。将反应混合物用氮气汽提并在80℃下真空除去挥发性化合物。得到984.0g浅褐色液体(熔点：14.6℃)。
实施例2：聚三乙醇胺+11EO/OH+3PO/OH+8EO/OH
在2L高压釜中混合90.0g在实施例1(a)中得到的聚三乙醇胺和4.2g氢氧化钾(50％水溶液)并在真空(<10毫巴)和120℃下搅拌2小时。将该高压釜用氮气吹扫并加热至140℃。在5小时内加入453.8g氧化乙烯，然后在1小时内加入163.1g氧化丙烯以及随后在3小时内加入330.0g氧化乙烯。为了使该反应完全，使该混合物在下额外后反应10小时140℃。将反应混合物用氮气汽提并在80℃下真空除去挥发性化合物。得到1038.0g浅褐色液体(熔点：13.5℃)。
对比例1：聚三乙醇胺+20氧化乙烯/OH
在2L高压釜中混合66.0g在实施例1(a)中得到的聚三乙醇胺和2.7g氢氧化钾(50％水溶液)并在真空(<10毫巴)和120℃下搅拌2小时。将该高压釜用氮气吹扫并加热至140℃。在6小时内加入605.6g氧化乙烯。为了使该反应完全，使该混合物在140℃下额外后反应10小时。将反应混合物用氮气汽提并在80℃下真空除去挥发性化合物。得到653.6g浅褐色固体(熔点：33.0℃)。
Claims (20)
1.取代聚醚胺，其可以按如下得到：
(a)使至少两种N-(羟基烷基)胺缩合，其中所述N-(羟基烷基)胺分别独立地选自式Ia和Ib的N-(羟基烷基)胺：
其中
A独立地选自C1亚烷基，C2亚烷基，线性或支化的C3亚烷基、C4亚烷基、C5亚烷基和C6亚烷基，
R3、R3*、R4、R4*、R5、R5*、R6、R6*、R7、R7*和R8独立地选自H；
取代或未取代的线性或支化烷基；取代或未取代的环烷基；以及取代或未取代的芳基，
得到聚醚胺；以及
(b)使在(a)中得到的所述聚醚胺的至少一个剩余羟基和/或若存在的话，至少一个仲氨基与氧化乙烯和至少一种选自氧化丙烯、氧化丁烯和氧化戊烯的其他氧化烯反应，
得到被至少一个亚烷氧基单元E取代的取代聚醚胺，
其中E为式II的亚烷氧基单元：
其中
R1独立地选自1,2-亚丙基、1,2-亚丁基和1,2-亚戊基；
R2独立地选自H、C1-C22烷基中的任一个和C7-C22芳烷基中的任一个；
m为独立地选自5-18范围内的值的整数；
n为独立地选自1-5范围内的值的整数；以及
p为独立地选自2-14范围内的值的整数，
其中取代聚醚胺具有在1巴环境压力下低于30℃的熔点。
2.根据权利要求1的取代聚醚胺，其中所述取代聚醚胺通过季化、质子化、硫酸化、转移硫酸化和/或磷酸化而进一步改性。
3.根据权利要求1的取代聚醚胺，其中A为C1亚烷基。
4.根据权利要求2的取代聚醚胺，其中A为C1亚烷基。
5.根据权利要求1-4中任一项的取代聚醚胺，其中缩合式Ia的N-(羟基烷基)胺而不缩合式Ib的N-(羟基烷基)胺。
6.根据权利要求1-4中任一项的取代聚醚胺，其中R3、R3*、R4、R4*、R5、R5*、R6、R6*、R7和R7*中的任一个或全部相互独立地为H、甲基或乙基。
7.根据权利要求5的取代聚醚胺，其中R3、R3*、R4、R4*、R5、R5*、R6、R6*、R7和R7*中的任一个或全部相互独立地为H、甲基或乙基。
8.根据权利要求1-4中任一项的取代聚醚胺，其中R8选自H、甲基、乙基和丁基。
9.根据权利要求7的取代聚醚胺，其中R8选自H、甲基、乙基和丁基。
10.根据权利要求1-4中任一项的取代聚醚胺，其中R1为1,2-亚丙基。
11.根据权利要求9的取代聚醚胺，其中R1为1,2-亚丙基。
12.根据权利要求1-4中任一项的取代聚醚胺，其中R2为H或C1-C4烷基。
13.根据权利要求11的取代聚醚胺，其中R2为H或C1-C4烷基。
14.根据权利要求1-4中任一项的取代聚醚胺，其中m为10-12，n为2-3和/或p为8-9。
15.根据权利要求13的取代聚醚胺，其中m为10-12，n为2-3和/或p为8-9。
16.根据权利要求2-4中任一项的取代聚醚胺，其中所述取代聚醚胺通过季化或具有额外硫酸化的季化进一步改性。
17.根据权利要求15的取代聚醚胺，其中所述取代聚醚胺通过季化或具有额外硫酸化的季化进一步改性。
18.根据权利要求1-4中任一项的取代聚醚胺，其中R3*、R4*、R5*、R6*和R7*为H且R3、R4、R5、R6、R7为H或甲基。
19.根据权利要求17的取代聚醚胺，其中R3*、R4*、R5*、R6*和R7*为H且R3、R4、R5、R6、R7为H或甲基。
20.根据权利要求1-19中任一项的取代聚醚胺在化妆品配制剂中，作为原油破乳剂，在喷墨颜料分散体中，在电镀中或者在水泥质组合物中的用途。
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| PCT/EP2016/051176 WO2016120141A1 (en) | 2015-01-26 | 2016-01-21 | Polyetheramines with low melting point |
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| AU2003272333A1 (en) | 2002-09-12 | 2004-04-30 | The Procter And Gamble Company | Polymer systems and cleaning compositions comprising same |
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| AR069243A1 (es) | 2007-11-09 | 2010-01-06 | Basf Se | Polialquileniminas alcoxiladas anfifilicas solubles en agua que tienen un bloque de oxido de polietileno interno y un bloque de oxido de polipropileno externo |
| WO2009061980A1 (en) * | 2007-11-09 | 2009-05-14 | The Procter & Gamble Company | Cleaning compositions comprising a multi-polymer system comprising at least one alkoxylated grease cleaning polymer |
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| MX2017009721A (es) | 2017-11-17 |
| WO2016120141A1 (en) | 2016-08-04 |
| RU2017130185A (ru) | 2019-02-28 |
| TR201819486T4 (tr) | 2019-01-21 |
| BR112017014193B8 (pt) | 2022-01-11 |
| RU2705994C2 (ru) | 2019-11-13 |
| PL3250628T3 (pl) | 2019-05-31 |
| RU2017130185A3 (zh) | 2019-04-12 |
| US10266649B2 (en) | 2019-04-23 |
| BR112017014193B1 (pt) | 2021-11-09 |
| CA2971017A1 (en) | 2016-08-04 |
| EP3250628A1 (en) | 2017-12-06 |
| ES2710014T3 (es) | 2019-04-22 |
| EP3250628B1 (en) | 2018-11-14 |
| KR20170108018A (ko) | 2017-09-26 |
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