CN114096582B - 倾点下降剂 - Google Patents
倾点下降剂 Download PDFInfo
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- CN114096582B CN114096582B CN202080049893.2A CN202080049893A CN114096582B CN 114096582 B CN114096582 B CN 114096582B CN 202080049893 A CN202080049893 A CN 202080049893A CN 114096582 B CN114096582 B CN 114096582B
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- 230000000994 depressogenic effect Effects 0.000 title description 5
- 229920000642 polymer Polymers 0.000 claims abstract description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 27
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 25
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 125000005647 linker group Chemical group 0.000 claims abstract description 12
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims abstract description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 7
- 150000002430 hydrocarbons Chemical class 0.000 claims description 33
- 239000004215 Carbon black (E152) Substances 0.000 claims description 22
- 239000010779 crude oil Substances 0.000 claims description 22
- 239000012530 fluid Substances 0.000 claims description 22
- 229930195733 hydrocarbon Natural products 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000005442 diisocyanate group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
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- 125000003277 amino group Chemical group 0.000 claims description 7
- 239000002199 base oil Substances 0.000 claims description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 7
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- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical group O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
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- 229920002873 Polyethylenimine Polymers 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
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- 239000002184 metal Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 229920000768 polyamine Polymers 0.000 description 6
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- 239000012188 paraffin wax Substances 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
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- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 238000006068 polycondensation reaction Methods 0.000 description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
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- 238000006482 condensation reaction Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
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- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
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- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
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- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 235000019809 paraffin wax Nutrition 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 235000019271 petrolatum Nutrition 0.000 description 2
- 229920013639 polyalphaolefin Polymers 0.000 description 2
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- 150000003077 polyols Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- 150000003673 urethanes Chemical class 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- DLYLVPHSKJVGLG-UHFFFAOYSA-N 4-(cyclohexylmethyl)cyclohexane-1,1-diamine Chemical compound C1CC(N)(N)CCC1CC1CCCCC1 DLYLVPHSKJVGLG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- OXIKYYJDTWKERT-UHFFFAOYSA-N [4-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCC(CN)CC1 OXIKYYJDTWKERT-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
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- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
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- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
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- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
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- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
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- 230000008030 elimination Effects 0.000 description 1
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- 239000003623 enhancer Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 229920006150 hyperbranched polyester Polymers 0.000 description 1
- 229920000587 hyperbranched polymer Polymers 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
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- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
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- 150000002596 lactones Chemical class 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- AQGNVWRYTKPRMR-UHFFFAOYSA-N n'-[2-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCNCCN AQGNVWRYTKPRMR-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
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- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- YLLIGHVCTUPGEH-UHFFFAOYSA-M potassium;ethanol;hydroxide Chemical compound [OH-].[K+].CCO YLLIGHVCTUPGEH-UHFFFAOYSA-M 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/024—Polyamines containing oxygen in the form of ether bonds in the main chain
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
- C08G18/2825—Alkanols, cycloalkanols or arylalkanols including terpenealcohols having at least 6 carbon atoms
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3271—Hydroxyamines
- C08G18/3278—Hydroxyamines containing at least three hydroxy groups
- C08G18/3281—Hydroxyamines containing at least three hydroxy groups containing three hydroxy groups
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- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/60—Polyamides or polyester-amides
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- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/60—Polyamides or polyester-amides
- C08G18/603—Polyamides
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- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
- C08G18/6415—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63 having nitrogen
- C08G18/6423—Polyalkylene polyamines; polyethylenimines; Derivatives thereof
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
-
- C—CHEMISTRY; METALLURGY
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Abstract
本发明涉及一种聚合物或低聚物,其包含a)低聚或聚合的核,其包含碳原子以及氧原子和氮原子的至少一种,和b)至少三个具有12至100个碳原子的烃基端基和/或侧基,其中所述烃基经由c)连接部分连接到所述核,c)连接部分,其包含i)氨酯基团和ii)选自氨酯基团、脲基团和缩二脲基团的基团。
Description
本发明涉及一种聚合物或低聚物,其包含低聚或聚合的核和至少三个连接到所述核的具有12至100个碳原子的烃基.本发明进一步涉及所述聚合物或低聚物用于改进烃基流体的冷流性质的用途,涉及减少烃基流体中的固体沉淀物的量的方法,涉及包含所述聚合物或低聚物和烃基流体的组合物,并涉及制备所述聚合物或低聚物的方法。
烃基流体有时在低温下遭受固体材料,特别是石蜡的沉淀。沉淀物最初作为浑浊变得可见的温度被称为浊点。在进一步冷却时,形成更多的沉淀物直至达到倾点。在一些情况下,压力变化同样可引发烃基流体中的固体材料的沉淀。
EP 1557441描述了基于具有多个烃基端基的超支化聚合物的成核剂。成核剂通常通过羟基官能的超支化聚酯与脂肪酸的缩合反应制备。该试剂被描述为倾点下降剂。
WO 2018/162403涉及疏水改性的聚烷醇胺作为蜡抑制剂、倾点下降剂和润滑剂添加剂的用途。疏水改性的聚烷醇胺通过两步法制备。在第一反应中,三烷醇胺在缩聚反应中彼此反应,以产生包含末端OH基团的支化聚烷醇胺。在第二步骤中,所得聚烷醇胺通过使末端OH基团与包含烃基的合适反应物反应而改性。通常,脂肪酸用作第二步骤中的反应物。
US 2013/0232858涉及特定的取代脲或氨酯用于进一步改进矿物油和原油的冷流性质的用途。在典型的实施方案中,取代脲通过二异氰酸酯与脂肪胺的反应制备,而取代氨酯通过二异氰酸酯与脂肪醇的反应制备。
仍然需要适用于改进烃基流体的冷流性质的其它材料。优选地,该材料应该在低用量下有效。
本发明提供一种聚合物或低聚物,其包含
a)低聚或聚合的核,其包含碳原子以及氧原子和氮原子的至少一种,和
b)至少三个具有12至100个碳原子的烃基端基和/或侧基,其中所述烃基经由c)连接部分连接到所述核,
c)连接部分,其包含i)氨酯基团和ii)选自氨酯基团、脲基团和缩二脲基团的基团。
低聚物是指具有中等相对分子质量的分子,其结构基本包含实际上或概念上衍生自较低相对分子质量的分子的少量单元。低聚物或聚合物通常包含平均至少三个重复单元,并具有分子量分布,即重均分子量与数均分子量的商大于1.0。
本发明的聚合物或低聚物具有至少三个烃基。烃基可作为连接到低聚或聚合的核的端基或侧基存在。当低聚或聚合的核是支化或超支化结构时,烃基通常作为侧接于核的基团存在。当聚合或低聚的核是线性或基本线性时,烃基可作为端基以及以侧基形式存在。
优选地,烃基是直链或支链的脂族基团。在一些实施方案中,具有12至50个碳原子的烃基是优选的。烃基可以相同或不同。在一些实施方案中,优选的是,烃基的碳原子数不同或支化程度或支化位置不同。
通常,本发明的聚合物或低聚物包含3至600个,优选3至300个,更优选3至100个烃基,最优选3至60个烃基b)。在一些实施方案中,聚合物或低聚物包含6至60个烃基b)。
烃基经由连接部分连接到低聚或聚合的核,所述连接部分包含i)氨酯基团和ii)选自氨酯基团、脲基团和缩二脲基团的基团。在优选实施方案中,连接部分基于有机二异氰酸酯。在一些优选实施方案中,选自氨酯基团、脲基团和缩二脲基团的基团ii)位于低聚或聚合的核和氨酯基团i)之间。
在本发明的聚合物或低聚物的优选实施方案中,连接部分包含位于氨酯基团i)和选自氨酯基团、脲基团和缩二脲基团的基团ii)之间的脂环族或芳族基团。脂环族基团优选是异佛尔酮二异氰酸酯的烃基。芳族基团优选是2,4-或2,6-甲苯二异氰酸酯的烃基。合适地,氨酯基团i)位于具有12至100个碳原子的烃基和选自氨酯基团、脲基团和缩二脲基团的基团ii)之间。
低聚或聚合的核合适地是基于平均官能度高于2.0的单体的支化或超支化结构。平均官能度高于2.0意味着单体可与其它单体形成多于2个连接。或者,低聚或聚合的核可以是线性或基本线性的结构。
在一些实施方案中,核是乙烯亚胺的聚合物或低聚物。优选地,核是支化聚乙烯亚胺。聚乙烯亚胺的重均分子量合适地在250至70.000g/mol,优选280至60.000g/mol的范围内。合适的聚乙烯亚胺可购得,例如以商品名来自BASF或以商品名Epomin来自Nippon Shokubai。分子量参考由聚乙烯亚胺的供应商提供的数据。
任选地,低聚或聚合的核,特别是聚乙烯亚胺核,可通过与胺反应性基团的反应改性。改性剂的实例是环氧化物,如缩水甘油醚、内酯、羧酸和丙烯酰基官能化合物。
在一些实施方案中,核是烷醇胺的低聚物或聚合物,被称为聚烷醇胺。烷醇胺的低聚物或聚合物通过烷醇胺缩合得到醚键而获得。如果需要,可以使用烷醇胺的混合物。通常,使用三烷醇胺,例如三乙醇胺。
聚烷醇胺可通过通式N(R1-OH)3(la)的三烷醇胺在缩聚反应中与彼此反应以产生具有末端OH基团的支化聚烷醇胺的反应阶段获得。任选地,其它单体可用于该缩聚。术语“缩聚”以通常方式表示通过消除小分子而组装聚合物反应单体。在本情况下,OH基团与彼此反应,以释放水并形成醚键。由于每个三烷醇胺(la)包含三个OH基团,形成支化聚烷醇胺。聚烷醇胺的制备是众所周知的。US 8540885从col.3、l.1至col.5、l.40描述了聚烷醇胺的制备。
在一些实施方案中,核是聚酰胺。聚酰胺合适地通过多胺与羧酸或其衍生物的反应制备。合适的羧酸具有一个、两个或更多个羧酸基团。也可能使用羧酸的混合物。也可使用羧酸酐。适当的多胺化合物的实例是脂族线性多胺,如1,6-六亚甲基二胺、二亚乙基三胺(DETA)、三亚乙基四胺(TETA)、四乙基五胺(TEPA)、五亚乙基六胺、六亚乙基七胺和更高分子量的同系物,根据n>5的式NH2-(C2H4NH)n-C2H4-NH2的线性缩合产物、二亚丙基三胺、(3-(2-氨基乙基)氨基丙胺、N,N-双(3-氨基丙基)甲胺、N,N-二甲基二亚丙基三胺,和N,N'-双(3-氨基丙基)乙二胺、三(3-氨基丙基)胺、三(2-氨基乙基)胺;进一步的实例是异佛尔酮二胺、4,4'-二氨基二苯甲烷、1,3-和1,4-二甲苯二胺、4,4'-二氨基二环己基甲烷、1,4-双(氨基甲基)环己烷、1-哌嗪乙胺、N,N'-双-(2-氨基乙基)哌嗪、N-[(2-氨基乙基)2-氨基乙基]哌嗪、基于聚环氧烷的二和/或多胺。在合适的聚酰胺核的制备中,必须确保所得聚酰胺具有至少三个选自羟基、伯胺和仲胺的反应性基团。这可通过胺基团与羧酸基团的摩尔比的选择或通过控制胺基团和羧酸基团的转化度来实现。
在一些实施方案中,核是支化聚酯。具有羟基端基的支化聚酯合适地通过具有2至6个羟基的多元醇和羧酸的缩合反应制备。合适的支化聚酯可通过多元醇与二羟甲基丙酸的缩合反应获得。这样的支化聚酯的制备描述在US 5418301中。合适的支化聚酯可以商品名Boltorn购自Perstorp。支化聚酯可任选通过单羧酸,例如饱和或不饱和脂肪酸的共缩合改性。
在一些优选实施方案中,聚合物或低聚物包含被具有6至24个碳原子的羧酸中和的胺基。已经发现,当其包含被这样的羧酸中和的胺基时,该聚合物或低聚物作为倾点下降剂或沉淀抑制剂的有效性改进。
已经发现本发明的聚合物或低聚物改变和/或减少在低温下烃基流体中的石蜡和/或蜡沉淀。这改进了烃基流体的冷流性质。因此,本发明进一步涉及所述聚合物或低聚物用于改进烃基流体的冷流性质的用途。本发明的聚合物也非常适合作为烃基流体中的倾点下降剂。
本发明还涉及一种减少在温度降低或压力变化时烃基流体中的固体沉淀物的量的方法,其包含向烃基流体中加入本发明的聚合物或低聚物。
在另一方面,本发明涉及一种组合物,其包含
i)本发明的聚合物或低聚物,和
ii)烃基流体。
烃基流体的实例包括原油、原油馏分、柴油燃料、金属加工流体、加热燃料、润滑剂基础油和润滑剂。
American Petroleum Institute(API)将润滑剂基础油分成五类。第I类基础油由进一步用溶剂萃取法精制以改进某些性质,如抗氧化性和除去蜡的分馏石油组成。第II类基础油由已加氢裂化以进一步精制和纯化的分馏石油组成。第III类基础油具有与第II类基础油类似的特性,只是第III类基础油具有更高粘度指数。第IV类基础油是聚α-烯烃(PAO)。第V类是第I至IV类没有描述的任何基础油的合并类。
当相对于烃基流体以相对低量使用时,聚合物或低聚物有效地改进冷流性质、降低倾点和减少固体沉淀物的量。合适地,本发明的低聚物或聚合物i)在组合物中的量在基于组合物的总重量计算0.001至1.000,优选0.010至0.800,更优选0.010至0.400重量%的范围内。
根据本发明的组合物可包含至少一种附加添加剂,如抗氧化剂、氧化抑制剂、腐蚀抑制剂、摩擦改进剂、金属钝化剂、防锈剂、消泡剂、粘度指数增强剂、分散剂、清净剂、极压剂或另外的倾点下降剂。
本发明进一步涉及一种制备本发明的聚合物或低聚物的方法。所述方法包含步骤i)使具有含12至100个碳原子的烃基的单醇与二异氰酸酯反应以提供具有一个异氰酸酯基团、一个氨酯基团和一个含12至100个碳原子的烃基的中间体,
ii)提供低聚或聚合的核,其包含碳原子以及氧原子和氮原子的至少一种,并具有至少三个选自羟基、伯胺、仲胺及其混合物的反应性基团,
iii)使步骤i)中制备的中间体与步骤ii)中提供的低聚或聚合的核反应。
在第一步骤中,使具有含12至100个碳原子的烃基的单醇与二异氰酸酯反应以提供具有一个异氰酸酯基团、一个氨酯基团和一个含12至100个碳原子的烃基的中间体。为了选择性地获得中间体,优选使用具有两个反应性不同的异氰酸酯基团的二异氰酸酯。这样的二异氰酸酯的实例是异佛尔酮二异氰酸酯和2,4-甲苯二异氰酸酯,以及它们的混合物。替代性地或附加地,在第一反应步骤中有可能使用相对于单醇摩尔过量的二异氰酸酯。如果需要,有可能在第一步骤后例如通过蒸馏除去未反应的二异氰酸酯。在一些实施方案中,在第一反应步骤中使用不同单醇的混合物。混合物中的单醇可在烃基的碳原子数以及在烃基的支化程度或支化位置方面不同。
在第二步骤中,提供如上所述的低聚或聚合的核。低聚或聚合的核官能团选自羟基、伯胺基、仲胺基或其组合,其能够与异氰酸酯基团反应。低聚或聚合的核具有至少三个这样的基团。通常,在低聚或聚合的核上存在3至600个这样的基团。
在第三步骤中,使步骤i)中制备的中间体与低聚或聚合的核反应。在这一步骤中,中间体的异氰酸酯基团与羟基和/或伯胺或仲胺基团反应,以分别形成氨酯或脲基团。选择中间体与低聚核的摩尔比以确保至少3个中间体分子连接到各个低聚或聚合的核。通常,3至600个中间分子连接到各个低聚或聚合的核。在第三步骤中,低聚或聚合的核的异氰酸酯反应性羟基或胺基的全部或仅一部分与异氰酸酯官能中间体反应,条件是至少3个中间体分子连接到各个低聚或聚合的核。
其中连接部分c)包含i)氨酯基团和ii)缩二脲基团的根据本发明的聚合物或低聚物可通过包含以下步骤的方法获得
i)使具有含12至100个碳原子的烃基的单醇与具有脲二酮基团的单异氰酸酯或二异氰酸酯反应以提供具有脲二酮基团、一个或两个氨酯基团和一个或两个含12至100个碳原子的烃基的中间体,
ii)提供低聚或聚合的核,其包含碳原子以及氧原子和氮原子的至少一种,并具有至少三个选自伯胺、仲胺及其组合的反应性基团,
iii)使步骤i)中制备的中间体与步骤ii)中提供的低聚或聚合的核反应。
实施例
一般方法
分子量
在分子不一致的物质的情况下,下文指定的分子量-如上文的描述中那样-代表数值平均值。借助对照聚苯乙烯标样的凝胶渗透色谱法测定分子量或数均分子量Mn。
羟值
通过用过量乙酸酐乙酰化而使醇式羟基反应。通过加水使过量乙酸酐水解成乙酸并使用KOH乙醇溶液反滴定。羟值是与1克物质中存在的羟基数相当的以毫克计的KOH量(根据DIN ISO 4629)。
胺值
在乙酸中的高氯酸(HClO4)已证实是适用于含有氮以及伯、仲和叔胺基团的有机碱的滴定剂。酸溶剂,如乙酸在该试验中可用于测定弱有机碱(良好的溶解性质,给质子的酸溶剂)。惰性溶剂,如环己烷、二氧杂环己烷、氯苯、丙酮和甲乙酮的添加可改进极弱碱的滴定(根据DIN 16945)。
NCO值
根据EN ISO 9369通过与二丁胺反应和随后滴定过量胺测定所用多异氰酸酯的游离NCO含量以及NCO加成反应的进程。
NMR
在Bruker DPX 300上在300MHz(1H)或75MHz(13C)下进行NMR测量。所用溶剂是氘代氯仿(CDCl3)和氘代二甲亚砜(DMSO-d6)。
中间产物的制备
中间产物A的制备
在配有冷凝器、搅拌器、温度传感器和氮气线路的干净干燥四颈烧瓶(500毫升)中装载异氰酸酯组分并加热到80℃。加入在二甲苯中的醇溶液以使温度不超过85℃。NCO基团与OH基团的摩尔比为2:1。在完全添加后在该温度下搅拌反应混合物。作为反应控制测量NCO值(DIN EN ISO 9369)。
表1:中间产物A的制备
中间产物B的制备(基于聚乙烯亚胺的聚合或低聚的核)
在配有冷凝器、KPG搅拌器、温度传感器和氮气线路的干净干燥四颈烧瓶(500毫升)中装载多胺(具有表中所示的不同分子量)并加热到100℃。加入改性组分(己内酯、环氧化物、丙烯酸酯或月桂酸)以使温度不超过120℃。在完全添加后在该温度下搅拌反应混合物直至改性组分完全反应(借助NMR控制)。
表2:中间产物B的制备(基于聚乙烯亚胺的聚合或低聚的核)
中间产物C的制备(基于聚三乙醇胺的聚合或低聚的核)
在配有冷凝器、KPG搅拌器、温度传感器和氮气线路的干净干燥四颈烧瓶(500毫升)中装载三乙醇胺和次膦酸(50%在H2O中)。
将混合物加热到230℃并在减压下除去反应水。在4小时的反应时间后,在减压(500毫巴)下除去剩余水。在3小时后,将反应混合物在100毫巴下冷却到140℃并在30分钟后将其冷却到室温。作为反应控制测量胺值(根据DIN 16945)和羟值(根据DIN ISO 4629)。
表3:中间产物C的制备(基于聚三乙醇胺的聚合或低聚的核)
中间产物D的制备(基于多胺和羧酸的聚酰胺聚合或低聚的核)
在配有具有水分离器的冷凝器、KPG搅拌器、温度传感器和氮气线路的干净干燥四颈烧瓶(500毫升)中装载己二酸和妥尔油脂肪酸并加热到80℃。将四亚乙基五胺添加到这种混合物中。在完全添加后将其加热到180℃并在减压下除去反应水。通过测量酸值和胺值来监测反应。
表4:中间产物D的制备
根据本发明的产物的制备
最终产物AB、AC和AD的制备
在配有冷凝器、KPG搅拌器、温度传感器和氮气线路的干净干燥四颈烧瓶(500毫升)中装载中间体B、C或D和二甲苯(将活性物质调节到40%)并加热到80℃。另外加入中间体A以使温度不超过85℃。在完全添加后,在该温度下搅拌反应混合物直至无法再检测到异氰酸酯基团。
表5:产物AB的制备
表6:产物AC的制备
表7:产物AD的制备
根据本发明的产物作为具有40重量%的不挥发物含量的在二甲苯中的溶液提供。
应用试验
原材料
Exxsol D 100:烃,C13-C16,异烷烃,环状化合物,<2%芳烃,购自ShellChemicals Europe
Sasolwax 5203:购自Sasol的链烷烃
Sasolwax 5803:购自Sasol的链烷烃
Sasolwax C80:合成蜡,购自Sasol的链烷烃
表8:合成原油制剂的制备
4%wt.蜡 | 15%wt.蜡 | 5%wt.蜡 | |
原材料 | 合成原油1[g] | 合成原油2[g] | 合成原油3[g] |
Exxsol D 100(1) | 460.80 | 408.00 | 456.00 |
二甲苯(2) | 307.20 | 272.00 | 304.00 |
Sasolwax 5203(3) | 16.00 | 40.00 | 32.00 |
Sasolwax 5803(4) | 16.00 | 40.00 | - |
Sasolwax C80(5) | - | 40.00 | 8.00 |
为了制备合成原油1,将所有原材料混合并在炉中在60℃(140℉)下放置2小时。
为了制备合成原油2和3,将所有原材料混合并在炉中在80℃(176℉)下放置4小时。
将温热的合成原油装在烧杯中以用于进一步的应用试验。
操作方法:冷指试验
装置:PSL Systemtechnik冷指设备CF15
使用冷指试验测定制备的添加剂的蜡抑制性质。通过在存在/不存在蜡抑制剂的情况下使原油暴露于冷金属手指表面来测定蜡抑制。在试验开始时,测定金属手指的初始重量。将在不存在蜡抑制剂的情况下在冷金属手指表面上的沉积物设定为100%。使用公式1计算抑制
Wa:在不存在蜡抑制剂的情况下在冷金属手指表面上的蜡沉积物的重量(以克计)
Wp:在蜡抑制剂存在下在冷金属手指表面上的蜡沉积物的重量(以克计)
将63.2克原油装在烧杯中并加热到80℃1小时。然后用Eppendorf移液管将40/20/16微升添加剂加入63.2克原油中。将原油与添加剂的混合物加热到80℃30分钟。向每个烧杯中加入磁搅拌棒。将带有制备的样品的烧杯置于机架中,并将金属手指插入制备的样品中。然后开启磁搅拌器(750rpm)。将带有沉积物的冷指称重。
用于不同合成原油的参数:
冷指装置合成原油2
-机架温度57℃
-指温度45℃
-试验程序时间:2小时
-搅拌速度:750rpm
冷指装置合成原油3
-机架温度44℃
-指温度24℃
-试验程序时间:2小时
-搅拌速度:750rpm
应用结果:冷指试验
在合成原油2(含15%wt.蜡)和合成原油3(含5%wt.蜡)中进行应用试验。使用根据本发明制备的样品在这两个原油体系中都实现优异的蜡抑制性质。
表9:合成原油2中的冷指试验
表10:合成原油3中的冷指试验
由表9和10中的结果可以得出结论,本发明的低聚物和聚合物在各种制剂中引起蜡沉淀的显著减少。
操作方法2:倾点试验
装置:水浴
作为起始温度和原油仍可流动的最后温度之间的差值测定倾点下降温度[℃]。
试验程序合成原油1
将合成原油在60℃(140℉)下加热1小时。在室温下根据ASTM Norm D 5853将50毫升原油置于试验广口瓶中。用Eppendorf移液管将添加剂加入原油样品中。将样品在60℃(140℉)下储存30分钟。此后将试验广口瓶置于冷浴(15℃(59℉))中。在冷浴中30分钟后,将试验广口瓶从水浴中缓慢取出并保持水平5秒。当观察到运动时,立即将试验广口瓶放回60℃(140℉)水浴中30分钟。此后将样品再次放入比之前低3℃(5℉)的冷浴中。重复这一程序,直至水平放置的原油在5秒内没有可见运动。可见运动的最后温度被视为倾点。
试验程序合成原油2&3
将合成原油在80℃(176℉)下加热1小时。在室温下将50毫升原油置于试验广口瓶中(ASTM Norm D 5853)。用Eppendorf移液管将添加剂加入原油样品中。将样品在80℃(176℉)下储存30分钟。此后将试验广口瓶置于冷浴(对于合成原油2为45℃(113℉),对于合成原油3为12℃(54℉)。在冷浴中30分钟后,将样品从水浴中缓慢取出并保持水平5秒。当观察到运动时,立即将试验广口瓶放回60℃(140℉)水浴中30分钟。此后将样品再次放入比之前低3℃(5℉)的冷浴中。重复这一程序,直至水平放置的原油在5秒内没有可见运动。可见运动的最后温度被视为倾点。
应用结果:倾点试验
在合成原油1(含4%wt.蜡)、合成原油2(含15%wt.蜡)和合成原油3(含5%wt.蜡)中进行应用试验。使用基于改性聚乙烯亚胺的根据本发明制备的样品观察到所有3个体系中的显著倾点下降。
表11:合成原油1中的倾点试验
表12:合成原油3中的倾点试验
表13:合成原油2中的倾点试验
由表11、12和13中的结果可以得出结论,本发明的低聚物和聚合物在低剂量下和在各种制剂中引起显著的倾点下降。
Claims (16)
1.一种聚合物或低聚物,其包含
a)低聚或聚合的核,其包含碳原子以及氧原子和氮原子的至少一种,和
b)至少三个具有12至100个碳原子的烃基端基和/或侧基,其中所述烃基经由c)连接部分连接到所述核,
c)连接部分,其包含i)氨酯基团和ii)选自氨酯基团、脲基团和缩二脲基团的基团。
2.根据权利要求1的聚合物或低聚物,其中所述烃基是直链或支链的脂族基团。
3.根据权利要求1的聚合物或低聚物,其中聚合物或低聚物包含3至600个烃基b)。
4.根据权利要求2的聚合物或低聚物,其中聚合物或低聚物包含3至600个烃基b)。
5.根据前述权利要求1-4任一项的聚合物或低聚物,其中所述连接部分包含位于氨酯基团和选自氨酯基团、脲基团和缩二脲基团的基团之间的芳族基团。
6.根据前述权利要求1-4任一项的聚合物或低聚物,其中所述核选自乙烯亚胺的聚合物或低聚物、三烷醇胺的聚合物或低聚物、支化聚酯和聚酰胺。
7.根据权利要求5的聚合物或低聚物,其中所述核选自乙烯亚胺的聚合物或低聚物、三烷醇胺的聚合物或低聚物、支化聚酯和聚酰胺。
8.根据前述权利要求1-4任一项的聚合物或低聚物,其中所述聚合物或低聚物包含被具有6至24个碳原子的羧酸中和的胺基。
9.根据权利要求7的聚合物或低聚物,其中所述聚合物或低聚物包含被具有6至24个碳原子的羧酸中和的胺基。
10.根据前述权利要求任一项的聚合物或低聚物用于改进烃基流体的冷流性质的用途。
11.一种减少在温度降低时烃基流体中的固体沉淀物的量的方法,其包含向烃基流体中加入根据前述权利要求1至9任一项的聚合物或低聚物。
12.一种组合物,其包含
i)根据前述权利要求1至9任一项的聚合物或低聚物,和
ii)烃基流体。
13.根据权利要求12的组合物,其中所述烃基流体是或包含原油、金属加工流体、柴油燃料、加热燃料、润滑剂和润滑剂基础油的至少一种。
14.根据权利要求12的组合物,其中低聚物或聚合物i)的量在基于组合物的总重量计算0.001至1.000重量%的范围内。
15.一种制备根据前述权利要求1至9任一项的聚合物或低聚物的方法,其包含步骤
i)使具有含12至100个碳原子的烃基的单醇与二异氰酸酯反应以提供具有一个异氰酸酯基团、一个氨酯基团和一个含12至100个碳原子的烃基的中间体,
ii)提供低聚或聚合的核,其包含碳原子以及氧原子和氮原子的至少一种,并具有至少三个选自羟基、伯胺和仲胺的反应性基团,
iii)使步骤i)中制备的中间体与步骤ii)中提供的低聚或聚合的核反应。
16.一种制备根据前述权利要求1至9任一项的聚合物或低聚物的方法,其中连接部分c)包含i)氨酯基团和ii)缩二脲基团,其包含步骤
i)使具有含12至100个碳原子的烃基的单醇与具有脲二酮基团的单异氰酸酯或二异氰酸酯反应以提供具有脲二酮基团、一个或两个氨酯基团和一个或两个含12至100个碳原子的烃基的中间体,
ii)提供低聚或聚合的核,其包含碳原子以及氧原子和氮原子的至少一种,并具有至少三个选自伯胺、仲胺及其组合的反应性基团,
iii)使步骤i)中制备的中间体与步骤ii)中提供的低聚或聚合的核反应。
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US (1) | US12054584B2 (zh) |
EP (1) | EP3997154B1 (zh) |
CN (1) | CN114096582B (zh) |
BR (1) | BR112022000234A2 (zh) |
CA (1) | CA3145615C (zh) |
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CN116333712B (zh) * | 2023-05-30 | 2023-08-11 | 新疆科力新技术发展股份有限公司 | 原油降凝剂及其制备方法 |
CN116333711B (zh) * | 2023-05-30 | 2023-08-11 | 新疆科力新技术发展股份有限公司 | 降凝剂及其制备方法 |
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ES2954622T3 (es) | 2023-11-23 |
US12054584B2 (en) | 2024-08-06 |
EP3997154B1 (en) | 2023-06-07 |
CA3145615A1 (en) | 2021-01-14 |
BR112022000234A2 (pt) | 2022-02-22 |
CN114096582A (zh) | 2022-02-25 |
US20220267523A1 (en) | 2022-08-25 |
EP3997154A1 (en) | 2022-05-18 |
WO2021004991A1 (en) | 2021-01-14 |
CA3145615C (en) | 2024-02-13 |
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