WO2021196332A1 - Substituted bisphenol phosphate ester aluminum salt nucleating agent, manufacturing method therefor, and application thereof - Google Patents
Substituted bisphenol phosphate ester aluminum salt nucleating agent, manufacturing method therefor, and application thereof Download PDFInfo
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- WO2021196332A1 WO2021196332A1 PCT/CN2020/087932 CN2020087932W WO2021196332A1 WO 2021196332 A1 WO2021196332 A1 WO 2021196332A1 CN 2020087932 W CN2020087932 W CN 2020087932W WO 2021196332 A1 WO2021196332 A1 WO 2021196332A1
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- WIPO (PCT)
- Prior art keywords
- aluminum salt
- acid
- nucleating agent
- substituted bisphenol
- bisphenol phosphate
- Prior art date
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- 229930185605 Bisphenol Natural products 0.000 title claims abstract description 43
- 239000002667 nucleating agent Substances 0.000 title claims abstract description 36
- -1 bisphenol phosphate ester aluminum salt Chemical class 0.000 title abstract description 18
- 229910019142 PO4 Inorganic materials 0.000 title abstract description 15
- 239000010452 phosphate Substances 0.000 title abstract description 15
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 229920000098 polyolefin Polymers 0.000 claims abstract description 7
- 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 39
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 claims description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 18
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 12
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000005639 Lauric acid Substances 0.000 claims description 7
- 235000021355 Stearic acid Nutrition 0.000 claims description 7
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 7
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 7
- 239000008117 stearic acid Substances 0.000 claims description 7
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 claims description 6
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 6
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 6
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 claims description 6
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 6
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 6
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 6
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 claims description 6
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 claims description 6
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 claims description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 6
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 claims description 6
- 150000007519 polyprotic acids Polymers 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 150000005846 sugar alcohols Polymers 0.000 claims description 6
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 claims description 6
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- CNNRPFQICPFDPO-UHFFFAOYSA-N octacosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCO CNNRPFQICPFDPO-UHFFFAOYSA-N 0.000 claims description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 3
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims description 3
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000005642 Oleic acid Substances 0.000 claims description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 3
- 235000021314 Palmitic acid Nutrition 0.000 claims description 3
- 235000021319 Palmitoleic acid Nutrition 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 3
- 150000001348 alkyl chlorides Chemical class 0.000 claims description 3
- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 claims description 3
- 229960000541 cetyl alcohol Drugs 0.000 claims description 3
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 claims description 3
- 150000001924 cycloalkanes Chemical class 0.000 claims description 3
- 229960000735 docosanol Drugs 0.000 claims description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 3
- 229960002446 octanoic acid Drugs 0.000 claims description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 3
- 235000021313 oleic acid Nutrition 0.000 claims description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims description 3
- 229940057402 undecyl alcohol Drugs 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- 229960002666 1-octacosanol Drugs 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
- 229940043348 myristyl alcohol Drugs 0.000 claims 1
- 230000006911 nucleation Effects 0.000 abstract description 3
- 238000010899 nucleation Methods 0.000 abstract description 3
- 239000006185 dispersion Substances 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- HGPXWXLYXNVULB-UHFFFAOYSA-M lithium stearate Chemical compound [Li+].CCCCCCCCCCCCCCCCCC([O-])=O HGPXWXLYXNVULB-UHFFFAOYSA-M 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 229910000162 sodium phosphate Inorganic materials 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
- C08K5/523—Esters of phosphoric acids, e.g. of H3PO4 with hydroxyaryl compounds
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65744—Esters of oxyacids of phosphorus condensed with carbocyclic or heterocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0083—Nucleating agents promoting the crystallisation of the polymer matrix
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/24—Crystallisation aids
Definitions
- the invention relates to a substituted bisphenol phosphate aluminum salt nucleating agent, a preparation method and application thereof, and belongs to the technical field of nucleating agents.
- Organophosphate is a type of polyolefin nucleating agent that has been rapidly developed in recent years and has been widely used. These products are mainly organic phosphate ester salts and phosphate ester basic salts.
- the organic phosphate ester salt nucleating agent is in a relatively low concentration. It can give polypropylene resin good rigidity, transparency, surface gloss and heat deformation resistance.
- the organic phosphate salt nucleating agent is mainly represented by the products of Asahi Denka, Japan. It can be divided into three generations.
- the first generation product name is bis(p-tert-butylphenoxy) sodium phosphate
- the second generation product name is 2,2'-methylenebis(4,6-di-tert-butylphenoxy) sodium phosphate
- the third generation product is 2,2'-methylenebis(4,6-di-tert-butylphenoxy) Base
- a compound of basic salt of aluminum phosphate and lithium stearate Due to the higher melting point of the phosphate salt, it is a dispersive nucleating agent.
- the molecular weight of the above third-generation phosphate salt nucleating agent becomes larger, and the main purpose of the compounding method is to improve its dispersibility in the resin, thereby increasing its composition. Nuclear performance.
- the publication number is 110734463A
- the patent name is a preparation method of bisphenol phosphate hydroxyaluminum salt nucleating agent
- the publication number is 110684049A
- the patent name is a one-pot type of bisphenol phosphate hydroxyaluminum salt nucleating agent
- the Chinese patent for the preparation method respectively discloses the preparation process of bisphenol phosphate aluminum salt.
- this application studies the preparation process of long-chain alkyl carboxylic acid substitution and long-chain alcohol substituted bisphenol phosphate aluminum salt.
- the present invention provides a substituted bisphenol phosphate aluminum salt nucleating agent and a preparation method and application thereof.
- the substituted bisphenol phosphate aluminum salt nucleating agent has a higher molecular weight and has a higher molecular weight.
- Polyolefin has better dispersibility, greater addition, and higher nucleation efficiency.
- the technical solution adopted by the present invention is a substituted bisphenol phosphate aluminum salt nucleating agent, which contains a compound of the following general formula (I),
- a method for preparing a substituted bisphenol phosphate aluminum salt nucleating agent The isopropoxy-substituted bisphenol phosphate aluminum salt and compound RH are heated in an organic solvent to fully react to obtain the substituted bisphenol phosphate aluminum salt.
- the compound RH is C 4 -C 30 saturated or unsaturated aliphatic monobasic acid or polybasic acid, C 4 -C 30 aromatic group or substituted aromatic group monobasic acid or polybasic acid, C 4 -C 30 saturated or unsaturated Saturated aliphatic monohydric alcohol or polyhydric alcohol, C 4 -C 30 aromatic group or substituted aromatic monohydric alcohol or polyhydric alcohol.
- the compound RH is butyric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, arachidic acid, propanol, butanol, pentanol Alcohol, hexanol, heptanol, nonanol, decanol, undecyl alcohol, dodecanol, tetradecanol, cetyl alcohol, stearyl alcohol, eicosanol, behenyl alcohol and twenty One or more mixtures of octanol.
- the organic solvent is a chloroalkane such as alkane, cycloalkane, alcohol, benzene, toluene, xylene, dichloromethane or chloroform.
- a chloroalkane such as alkane, cycloalkane, alcohol, benzene, toluene, xylene, dichloromethane or chloroform.
- reaction molar ratio of the isopropoxy-substituted bisphenol phosphate aluminum salt and the compound RH is 1:0.9-1.1.
- it is heated to 25°C to 140°C in an organic solvent.
- it is heated to 65°C to 110°C in an organic solvent.
- the present invention has the following technical effects: the third-generation phosphoric acid ester salt 2,2'-methylene bis(4,6-di-tert-butylphenoxy) aluminum phosphate basic salt molecule
- the hydroxyl group in the structure is replaced by a long-chain carboxylic acid or a long-chain alkoxy group.
- the purpose is to lower the melting point of the product and further improve its dispersibility in the resin.
- the produced long-chain substituted bisphenol phosphate aluminum salt nucleating agent has a higher molecular weight and a lower melting point.
- Figure 1 is an infrared spectrum of samples of different substitutions in the present invention.
- a substituted bisphenol phosphate aluminum salt nucleating agent which contains a compound of the following general formula (I),
- a method for preparing a substituted bisphenol phosphate aluminum salt nucleating agent The isopropoxy-substituted bisphenol phosphate aluminum salt and compound RH are heated in an organic solvent to fully react to obtain the substituted bisphenol phosphate aluminum salt.
- the compound RH is C 4 -C 30 saturated or unsaturated aliphatic monobasic acid or polybasic acid, C 4 -C 30 aromatic group or substituted aromatic group monobasic acid or polybasic acid, C 4 -C 30 saturated or unsaturated aliphatic group Monohydric alcohol or polyhydric alcohol, C 4 -C 30 aromatic group or substituted aromatic group monohydric alcohol or polyhydric alcohol.
- the organic solvent can be chloroalkanes such as alkanes, cycloalkanes, alcohols, benzene, toluene, xylene, dichloromethane, or chloroform.
- the reaction molar ratio of isopropoxy-substituted bisphenol phosphate aluminum salt and compound RH is 1:0.9-1.1. Heat to 25°C ⁇ 140°C in organic solvent. It is best to heat to 65°C ⁇ 110°C.
- the substituted bisphenol phosphate aluminum salt nucleating agent is applied to polyolefins, which can increase the crystallization temperature of the polymer, accelerate the crystallization speed and improve the mechanical properties of the polymer.
- Example 1 Add 36 g of 2,2′-methylene bis(4,6-di-tert-butylphenoxy) phosphate, 3.34 g of sodium hydroxide and 100 ml of water into the reaction flask, stir and heat to 80 The reaction was kept at the temperature of Celsius for two hours, and the bisphenol phosphate sodium salt was obtained after suction filtration and drying.
- Comparative example 1 Add 24.3 g of 2,2'-methylene bis(4,6-di-tert-butylphenoxy) phosphate, 5.1 g of aluminum isopropoxide and 100 ml of toluene into the reaction flask, stir and heat to reflux for reaction After 2 hours, 7.1 g of stearic acid was added to continue the reflux reaction for 1 hour. After the reaction is completed, 100 ml of water is added to distill toluene to be recovered, filtered and dried to obtain the product stearic acid substituted aluminum bisphenol phosphate.
- Comparative Example 2 Add 24.3 g of 2,2'-methylene bis(4,6-di-tert-butylphenoxy) phosphate, 5.1 g of aluminum isopropoxide and 100 ml of toluene into the reaction flask, stir and heat to reflux for reaction 2 hours, then add 5.0 g of lauric acid to continue the reflux reaction for 1 hour. After the reaction is completed, 100 ml of water is added to distill to recover toluene, filtered and dried to obtain the product lauric acid substituted aluminum bisphenol phosphate.
- Comparative Example 3 Add 24.3 g of 2,2'-methylene bis(4,6-di-tert-butylphenoxy) phosphate, 5.1 g of aluminum isopropoxide and 100 ml of toluene into the reaction flask, stir and heat to reflux for reaction After 2 hours, 6.8 g of stearyl alcohol was added to continue the reflux reaction for 1 hour. After the completion of the reaction, 100 ml of water was added to distill toluene to recover, filtered and dried to obtain the product stearyl alcohol substituted bisphenol phosphate aluminum salt.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The present invention belongs to the technical field of nucleating agents and involves a substituted bisphenol phosphate ester aluminum salt nucleating agent, a manufacturing method therefor, and an application thereof, and specifically, said substituted bisphenol phosphate ester aluminum salt nucleating agent includes a compound as shown in general formula (I). The substituted bisphenol phosphate ester aluminum salt nucleating agent in the present invention has a higher molecular mass, dispersion is better among polyolefins, has a greater add amount, and has a higher nucleation efficiency.
Description
本发明涉及一种取代双酚磷酸酯铝盐成核剂及其制备方法以及其应用，属于成核剂技术领域。The invention relates to a substituted bisphenol phosphate aluminum salt nucleating agent, a preparation method and application thereof, and belongs to the technical field of nucleating agents.
有机磷酸盐是近年来快速发展并得到广泛应用的一类聚烯烃成核剂，这些产品主要是有机磷酸酯盐和磷酸酯碱式盐，有机磷酸酯盐类成核剂在相对较低的浓度下能够赋予聚丙烯树脂良好的刚性、透明性、表面光泽和耐热变形性。有机磷酸酯盐成核剂主要是以日本旭电化公司的产品为代表，可分为三代产品，第一代产品名称为双(对叔丁基苯氧基)磷酸钠，第二代产品名称为2,2′-亚甲基双(4,6-二叔丁基苯氧基)磷酸钠，第三代产品是2,2′-亚甲基双(4,6-二叔丁基苯氧基)磷酸铝的碱式盐和硬脂酸锂的复配物。由于磷酸酯盐的熔点较高，属于分散型成核剂，上面三代磷酸酯盐成核剂分子量依次变大，并且经过复配方法主要目的是提高其在树脂中的分散性能，从而提高其成核性能。Organophosphate is a type of polyolefin nucleating agent that has been rapidly developed in recent years and has been widely used. These products are mainly organic phosphate ester salts and phosphate ester basic salts. The organic phosphate ester salt nucleating agent is in a relatively low concentration. It can give polypropylene resin good rigidity, transparency, surface gloss and heat deformation resistance. The organic phosphate salt nucleating agent is mainly represented by the products of Asahi Denka, Japan. It can be divided into three generations. The first generation product name is bis(p-tert-butylphenoxy) sodium phosphate, and the second generation product name is 2,2'-methylenebis(4,6-di-tert-butylphenoxy) sodium phosphate, the third generation product is 2,2'-methylenebis(4,6-di-tert-butylphenoxy) Base) A compound of basic salt of aluminum phosphate and lithium stearate. Due to the higher melting point of the phosphate salt, it is a dispersive nucleating agent. The molecular weight of the above third-generation phosphate salt nucleating agent becomes larger, and the main purpose of the compounding method is to improve its dispersibility in the resin, thereby increasing its composition. Nuclear performance.
目前，公开号为110734463A，专利名称为一种双酚磷酸酯羟基铝盐成核剂的制备方法和公开号为110684049A，专利名称为一种双酚磷酸酯羟基铝盐成核剂的一锅式制备方法的中国专利，其分别公开了制备双酚磷酸酯铝盐的工艺，本申请在此基础上研究长链烷基羧酸取代和长链醇取代双酚磷酸酯铝盐的制备工艺。Currently, the publication number is 110734463A, the patent name is a preparation method of bisphenol phosphate hydroxyaluminum salt nucleating agent and the publication number is 110684049A, the patent name is a one-pot type of bisphenol phosphate hydroxyaluminum salt nucleating agent The Chinese patent for the preparation method respectively discloses the preparation process of bisphenol phosphate aluminum salt. On this basis, this application studies the preparation process of long-chain alkyl carboxylic acid substitution and long-chain alcohol substituted bisphenol phosphate aluminum salt.
发明内容Summary of the invention
为解决现有技术存在的技术问题，本发明提供了一种取代双酚磷酸酯铝盐成核剂及其制备方法以及其应用，该取代双酚磷酸酯铝盐成核剂分子量更高，在聚烯烃中的分散性更好，添加量更大，成核效率更高。In order to solve the technical problems existing in the prior art, the present invention provides a substituted bisphenol phosphate aluminum salt nucleating agent and a preparation method and application thereof. The substituted bisphenol phosphate aluminum salt nucleating agent has a higher molecular weight and has a higher molecular weight. Polyolefin has better dispersibility, greater addition, and higher nucleation efficiency.
为实现上述目的，本发明所采用的技术方案为一种取代双酚磷酸酯铝盐成核剂，其含有下述通式(I)的化合物，In order to achieve the above object, the technical solution adopted by the present invention is a substituted bisphenol phosphate aluminum salt nucleating agent, which contains a compound of the following general formula (I),
一种取代双酚磷酸酯铝盐成核剂的制备方法，将异丙氧基取代双酚磷酸酯铝盐和化合物RH在有机溶剂中加热，充分反应得到取代双酚磷酸酯铝盐，A method for preparing a substituted bisphenol phosphate aluminum salt nucleating agent. The isopropoxy-substituted bisphenol phosphate aluminum salt and compound RH are heated in an organic solvent to fully react to obtain the substituted bisphenol phosphate aluminum salt.
其合成反应方程式如下：The synthesis reaction equation is as follows:
优选的，所述化合物RH为C
4-C
30饱和或不饱和脂肪基一元酸或多元酸、C
4-C
30芳香基或取代芳香基一元酸或多元酸、C
4-C
30饱和或不饱和脂肪基一元醇或多元醇、C
4-C
30芳香基或取代芳香基一元醇或多元醇。
Preferably, the compound RH is C 4 -C 30 saturated or unsaturated aliphatic monobasic acid or polybasic acid, C 4 -C 30 aromatic group or substituted aromatic group monobasic acid or polybasic acid, C 4 -C 30 saturated or unsaturated Saturated aliphatic monohydric alcohol or polyhydric alcohol, C 4 -C 30 aromatic group or substituted aromatic monohydric alcohol or polyhydric alcohol.
优选的，所述化合物RH为丁酸、己酸、辛酸、癸酸、月桂酸、肉豆蔻酸、棕榈酸、棕榈油酸、硬脂酸、油酸、花生酸、丙醇、丁醇、戊醇、己醇、庚醇、壬醇、癸醇、十一烷醇、十二烷醇、十四烷醇、十六烷醇、十八烷醇、二十烷醇、二十二醇和二十八烷醇中的一种或多种的混合物。Preferably, the compound RH is butyric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, arachidic acid, propanol, butanol, pentanol Alcohol, hexanol, heptanol, nonanol, decanol, undecyl alcohol, dodecanol, tetradecanol, cetyl alcohol, stearyl alcohol, eicosanol, behenyl alcohol and twenty One or more mixtures of octanol.
优选的，所述有机溶剂为烷烃、环烷烃、醇、苯、甲苯、二甲苯、二氯甲 烷或氯仿等氯烷烃。Preferably, the organic solvent is a chloroalkane such as alkane, cycloalkane, alcohol, benzene, toluene, xylene, dichloromethane or chloroform.
优选的，所述异丙氧基取代双酚磷酸酯铝盐和化合物RH的反应摩尔比为1:0.9～1.1。Preferably, the reaction molar ratio of the isopropoxy-substituted bisphenol phosphate aluminum salt and the compound RH is 1:0.9-1.1.
优选的，在有机溶剂中加热至25℃～140℃。Preferably, it is heated to 25°C to 140°C in an organic solvent.
优选的，在有机溶剂中加热至65℃～110℃。Preferably, it is heated to 65°C to 110°C in an organic solvent.
一种取代双酚磷酸酯铝盐成核剂的应用，取代双酚磷酸酯铝盐成核剂应用于聚烯烃。An application of a substituted bisphenol phosphate aluminum salt nucleating agent, and a substituted bisphenol phosphate aluminum salt nucleating agent used in polyolefins.
与现有技术相比，本发明具有以下技术效果：将第三代磷酸酯盐2,2′-亚甲基双(4,6-二叔丁基苯氧基)磷酸铝的碱式盐分子结构中的羟基使用长链羧酸跟或长链烷氧基取代，目的是降低产品熔点并进一步提高其在树脂中的分散性。生成的长链取代双酚磷酸酯铝盐成核剂分子量更高，熔点更低，其和硬脂酸锂复配作为成核剂在聚烯烃中的分散性更好，添加量更大且不团聚，成核效率更高，并且能够提高聚合物结晶温度、加快结晶速度和提高聚合物机械性能。Compared with the prior art, the present invention has the following technical effects: the third-generation phosphoric acid ester salt 2,2'-methylene bis(4,6-di-tert-butylphenoxy) aluminum phosphate basic salt molecule The hydroxyl group in the structure is replaced by a long-chain carboxylic acid or a long-chain alkoxy group. The purpose is to lower the melting point of the product and further improve its dispersibility in the resin. The produced long-chain substituted bisphenol phosphate aluminum salt nucleating agent has a higher molecular weight and a lower melting point. It is compounded with lithium stearate as a nucleating agent to have better dispersibility in polyolefins, and the addition amount is larger and does not Agglomeration, nucleation efficiency is higher, and can increase the crystallization temperature of the polymer, accelerate the crystallization speed and improve the mechanical properties of the polymer.
图1为本发明中不同取代的样品红外谱图。Figure 1 is an infrared spectrum of samples of different substitutions in the present invention.
为了使本发明所要解决的技术问题、技术方案及有益效果更加清楚明白，以下结合附图及实施例，对本发明进行进一步详细说明。应当理解，此处所描述的具体实施例仅仅用以解释本发明，并不用于限定本发明。In order to make the technical problems, technical solutions and beneficial effects to be solved by the present invention clearer, the following further describes the present invention in detail with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described here are only used to explain the present invention, but not used to limit the present invention.
一种取代双酚磷酸酯铝盐成核剂，其含有下述通式(I)的化合物，A substituted bisphenol phosphate aluminum salt nucleating agent, which contains a compound of the following general formula (I),
一种取代双酚磷酸酯铝盐成核剂的制备方法，将异丙氧基取代双酚磷酸酯铝盐和化合物RH在有机溶剂中加热，充分反应得到取代双酚磷酸酯铝盐，A method for preparing a substituted bisphenol phosphate aluminum salt nucleating agent. The isopropoxy-substituted bisphenol phosphate aluminum salt and compound RH are heated in an organic solvent to fully react to obtain the substituted bisphenol phosphate aluminum salt.
其合成反应方程式如下：The synthesis reaction equation is as follows:
其中，化合物RH为C
4-C
30饱和或不饱和脂肪基一元酸或多元酸、C
4-C
30芳香基或取代芳香基一元酸或多元酸、C
4-C
30饱和或不饱和脂肪基一元醇或多元醇、C
4-C
30芳香基或取代芳香基一元醇或多元醇。最好为丁酸、己酸、辛酸、癸酸、月桂酸、肉豆蔻酸、棕榈酸、棕榈油酸、硬脂酸、油酸、花生酸、丙醇、丁醇、戊醇、己醇、庚醇、壬醇、癸醇、十一烷醇、十二烷醇、十四烷醇、十六烷醇、十八烷醇、二十烷醇、二十二醇和二十八烷醇中的一种或多种的混合物。
Among them, the compound RH is C 4 -C 30 saturated or unsaturated aliphatic monobasic acid or polybasic acid, C 4 -C 30 aromatic group or substituted aromatic group monobasic acid or polybasic acid, C 4 -C 30 saturated or unsaturated aliphatic group Monohydric alcohol or polyhydric alcohol, C 4 -C 30 aromatic group or substituted aromatic group monohydric alcohol or polyhydric alcohol. Preferably, butyric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, arachidic acid, propanol, butanol, pentanol, hexanol, Among heptyl alcohol, nonanol, decanol, undecyl alcohol, dodecanol, tetradecanol, cetyl alcohol, stearyl alcohol, eicosanol, behenyl alcohol, and octacosanol One or more mixtures.
此外，有机溶剂可以采用为烷烃、环烷烃、醇、苯、甲苯、二甲苯、二氯甲烷或氯仿等氯烷烃。异丙氧基取代双酚磷酸酯铝盐和化合物RH的反应摩尔比为1:0.9～1.1。在有机溶剂中加热至25℃～140℃。最好加热至65℃～110℃。In addition, the organic solvent can be chloroalkanes such as alkanes, cycloalkanes, alcohols, benzene, toluene, xylene, dichloromethane, or chloroform. The reaction molar ratio of isopropoxy-substituted bisphenol phosphate aluminum salt and compound RH is 1:0.9-1.1. Heat to 25℃～140℃ in organic solvent. It is best to heat to 65℃～110℃.
一种取代双酚磷酸酯铝盐成核剂的应用，取代双酚磷酸酯铝盐成核剂应用 于聚烯烃，其能够提高聚合物结晶温度、加快结晶速度和提高聚合物机械性能。An application of a substituted bisphenol phosphate aluminum salt nucleating agent. The substituted bisphenol phosphate aluminum salt nucleating agent is applied to polyolefins, which can increase the crystallization temperature of the polymer, accelerate the crystallization speed and improve the mechanical properties of the polymer.
下面结合实例1、对比例1、对比例2和对比例3对取代双酚磷酸酯铝盐做进一步说明。In the following, the substituted bisphenol phosphate aluminum salt will be further described in conjunction with Example 1, Comparative Example 1, Comparative Example 2 and Comparative Example 3.
实例1：将36克2,2′-亚甲基双(4,6-二叔丁基苯氧基)磷酸酯、3.34克氢氧化钠和100毫升水加入反应瓶中，搅拌并加热至80摄氏度保持反应两小时，抽滤并干燥后得双酚磷酸酯钠盐。将上述钠盐加入170毫升酒精水混合液中，升温至60摄氏度左右，将8.4克三氯化铝和10毫升水制备的溶液加到上述反应液中，保温反应两小时，然后向釜中加入1.56克片碱，反应半小时，降温放料、抽滤并干燥后得到产品双酚磷酸酯羟基铝盐。Example 1: Add 36 g of 2,2′-methylene bis(4,6-di-tert-butylphenoxy) phosphate, 3.34 g of sodium hydroxide and 100 ml of water into the reaction flask, stir and heat to 80 The reaction was kept at the temperature of Celsius for two hours, and the bisphenol phosphate sodium salt was obtained after suction filtration and drying. Add the above sodium salt to 170 ml of alcohol-water mixture, heat up to about 60 degrees Celsius, add a solution prepared by 8.4 g of aluminum trichloride and 10 ml of water to the above reaction solution, keep it warm and react for two hours, and then add it to the kettle 1.56 g of caustic soda, reacted for half an hour, cooled and discharged, suction filtered and dried to obtain the product bisphenol phosphate hydroxyaluminum salt.
对比例1：将24.3克2,2′-亚甲基双(4,6-二叔丁基苯氧基)磷酸酯5.1克异丙醇铝和100毫升甲苯加入反应瓶中，搅拌加热回流反应2小时，然后加入7.1克硬脂酸继续回流反应1小时。反应完毕后加入100毫升水蒸馏回收甲苯，过滤并干燥得到产品硬脂酸取代双酚磷酸酯铝盐。Comparative example 1: Add 24.3 g of 2,2'-methylene bis(4,6-di-tert-butylphenoxy) phosphate, 5.1 g of aluminum isopropoxide and 100 ml of toluene into the reaction flask, stir and heat to reflux for reaction After 2 hours, 7.1 g of stearic acid was added to continue the reflux reaction for 1 hour. After the reaction is completed, 100 ml of water is added to distill toluene to be recovered, filtered and dried to obtain the product stearic acid substituted aluminum bisphenol phosphate.
对比例2：将24.3克2,2′-亚甲基双(4,6-二叔丁基苯氧基)磷酸酯5.1克异丙醇铝和100毫升甲苯加入反应瓶中，搅拌加热回流反应2小时，然后加入5.0克月桂酸继续回流反应1小时。反应完毕后加入100毫升水蒸馏回收甲苯，过滤并干燥得到产品月桂酸取代双酚磷酸酯铝盐。Comparative Example 2: Add 24.3 g of 2,2'-methylene bis(4,6-di-tert-butylphenoxy) phosphate, 5.1 g of aluminum isopropoxide and 100 ml of toluene into the reaction flask, stir and heat to reflux for reaction 2 hours, then add 5.0 g of lauric acid to continue the reflux reaction for 1 hour. After the reaction is completed, 100 ml of water is added to distill to recover toluene, filtered and dried to obtain the product lauric acid substituted aluminum bisphenol phosphate.
对比例3：将24.3克2,2′-亚甲基双(4,6-二叔丁基苯氧基)磷酸酯5.1克异丙醇铝和100毫升甲苯加入反应瓶中，搅拌加热回流反应2小时，然后加入6.8克十八醇继续回流反应1小时。反应完毕后加入100毫升水蒸馏回收甲苯，过滤并干燥得到产品十八醇取代双酚磷酸酯铝盐。Comparative Example 3: Add 24.3 g of 2,2'-methylene bis(4,6-di-tert-butylphenoxy) phosphate, 5.1 g of aluminum isopropoxide and 100 ml of toluene into the reaction flask, stir and heat to reflux for reaction After 2 hours, 6.8 g of stearyl alcohol was added to continue the reflux reaction for 1 hour. After the completion of the reaction, 100 ml of water was added to distill toluene to recover, filtered and dried to obtain the product stearyl alcohol substituted bisphenol phosphate aluminum salt.
具体分析如下：The specific analysis is as follows:
1、元素分析1. Elemental analysis
表1样品的元素含量Table 1 The element content of the sample
从上表的元素分析数据可知，对比例与实例1在同种元素的含量上有显著性的差别，说明对比例的取代结构和实例1有区别，从对比例的元素理论含量和实测值的对比可知，两者数据相差较小，说明目标取代结构已成功取代上。From the element analysis data in the above table, it can be seen that there is a significant difference in the content of the same element between the comparative example and the example 1, which shows that the substitution structure of the comparative example is different from that of the example 1. The comparison shows that the difference between the two data is small, indicating that the target substitution structure has been successfully replaced.
2、红外分析2. Infrared analysis
如图1所示，1750cm
-1是C＝O的特征峰，说明月桂酸和硬脂酸已成功取代上，谱图上对比例全部出现715cm
-1特征峰，而实例没有，这是(-CH
2)n的特征峰位置，说明月桂酸、硬脂酸、十八醇已成功取代上。1380cm
-1处裂分成两个峰，且前低后高，这个位置是叔丁基的特征峰位，1100cm
-1处是多价金属取代的特征峰位置，945cm
-1是P-O的伸缩振动，这些峰位置表明磷酸羟基铝盐的主体结构已合成。
As shown in Figure 1, 1750cm -1 is the characteristic peak of C=O, indicating that lauric acid and stearic acid have been successfully replaced. All the characteristic peaks of 715cm -1 appear in the comparative example on the spectrum, but the example does not. This is (- The characteristic peak positions of CH 2 )n indicate that lauric acid, stearic acid, and stearyl alcohol have been successfully substituted. At 1380cm -1 split into two peaks, and low to high, this position is tert-butyl characteristic peaks, 1100cm -1 is a polyvalent metal substituted at the characteristic peak positions, 945 cm -1 is the stretching vibration of the PO, These peak positions indicate that the main structure of hydroxyaluminum phosphate has been synthesized.
3、熔点测试3. Melting point test
以上所述仅为本发明的较佳实施例而已，并不用以限制本发明，凡在本发明的精神和原则之内所作的任何修改、等同替换和改进等，均应包在本发明范围内。The above are only the preferred embodiments of the present invention and are not intended to limit the present invention. Any modification, equivalent replacement and improvement made within the spirit and principle of the present invention should be included in the scope of the present invention. .
Claims (9)
- 一种取代双酚磷酸酯铝盐成核剂，其特征在于：其含有下述通式(I)的化合物，A substituted bisphenol phosphate aluminum salt nucleating agent, characterized in that it contains a compound of the following general formula (I),
- 一种取代双酚磷酸酯铝盐成核剂的制备方法，其特征在于：将异丙氧基取代双酚磷酸酯铝盐和化合物RH在有机溶剂中加热，充分反应得到取代双酚磷酸酯铝盐，A preparation method of substituted bisphenol phosphate aluminum salt nucleating agent, characterized in that: isopropoxy substituted bisphenol phosphate aluminum salt and compound RH are heated in an organic solvent to fully react to obtain substituted bisphenol phosphate aluminum Salt,其合成反应方程式如下：The synthesis reaction equation is as follows:
- 根据权利要求2所述的一种取代双酚磷酸酯铝盐成核剂的制备方法，其特征在于：所述化合物RH为C 4-C 30饱和或不饱和脂肪基一元酸或多元酸、C 4-C 30芳香基或取代芳香基一元酸或多元酸、C 4-C 30饱和或不饱和脂肪基一元醇或多元醇、C 4-C 30芳香基或取代芳香基一元醇或多元醇。 The method for preparing a substituted bisphenol phosphate aluminum salt nucleating agent according to claim 2, wherein the compound RH is C 4 -C 30 saturated or unsaturated aliphatic monobasic acid or polybasic acid, C 4- C 30 aromatic group or substituted aromatic monobasic acid or polybasic acid, C 4 -C 30 saturated or unsaturated aliphatic monobasic alcohol or polyhydric alcohol, C 4 -C 30 aromatic group or substituted aromatic monobasic alcohol or polyhydric alcohol.
- 根据权利要求2所述的一种取代双酚磷酸酯铝盐成核剂，其特征在于：所述化合物RH为丁酸、己酸、辛酸、癸酸、月桂酸、肉豆蔻酸、棕榈酸、棕榈油酸、硬脂酸、油酸、花生酸、丙醇、丁醇、戊醇、己醇、庚醇、壬醇、癸醇、 十一烷醇、十二烷醇、十四烷醇、十六烷醇、十八烷醇、二十烷醇、二十二醇和二十八烷醇中的一种或多种的混合物。A substituted bisphenol phosphate aluminum salt nucleating agent according to claim 2, wherein the compound RH is butyric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, Palmitoleic acid, stearic acid, oleic acid, arachidic acid, propanol, butanol, pentanol, hexanol, heptanol, nonanol, decanol, undecyl alcohol, dodecanol, myristyl alcohol, A mixture of one or more of cetyl alcohol, stearyl alcohol, eicosanol, behenyl alcohol, and octacosanol.
- 根据权利要求2-4任一项所述的一种取代双酚磷酸酯铝盐成核剂的制备方法，其特征在于：所述有机溶剂为烷烃、环烷烃、醇、苯、甲苯、二甲苯、二氯甲烷或氯仿等氯烷烃。The method for preparing a substituted bisphenol phosphate aluminum salt nucleating agent according to any one of claims 2-4, wherein the organic solvent is alkane, cycloalkane, alcohol, benzene, toluene, xylene , Dichloromethane or chloroform and other chloroalkanes.
- 根据权利要求2-4任一所述的一种取代双酚磷酸酯铝盐成核剂的制备方法，其特征在于：所述异丙氧基取代双酚磷酸酯铝盐和化合物RH的反应摩尔比为1:0.9～1.1。The preparation method of a substituted bisphenol phosphate aluminum salt nucleating agent according to any one of claims 2-4, wherein the reaction between the isopropoxy-substituted bisphenol phosphate aluminum salt and the compound RH The ratio is 1:0.9～1.1.
- 根据权利要求2-4任一项所述的一种取代双酚磷酸酯铝盐成核剂的制备方法，其特征在于：在有机溶剂中加热至25℃～140℃。The method for preparing a substituted bisphenol phosphate aluminum salt nucleating agent according to any one of claims 2 to 4, characterized in that: heating in an organic solvent to 25°C to 140°C.
- 根据权利要求7任一项所述的一种取代双酚磷酸酯铝盐成核剂的制备方法，其特征在于：在有机溶剂中加热至65℃～110℃。The method for preparing a substituted bisphenol phosphate aluminum salt nucleating agent according to any one of claim 7, characterized in that: heating in an organic solvent to 65°C to 110°C.
- 一种取代双酚磷酸酯铝盐成核剂的应用，其特征在于：取代双酚磷酸酯铝盐成核剂应用于聚烯烃。An application of a substituted bisphenol phosphate aluminum salt nucleating agent is characterized in that the substituted bisphenol phosphate aluminum salt nucleating agent is applied to polyolefin.
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| CN102807582A (en) * | 2011-06-02 | 2012-12-05 | 中国石油化工股份有限公司 | Preparation methods of organic phosphate ester and organic phosphate nucleating agent |
| CN102827205A (en) * | 2011-06-17 | 2012-12-19 | 中国石油化工股份有限公司 | Preparation method of nucleating agent |
| CN110734463A (en) * | 2019-10-16 | 2020-01-31 | 山西省化工研究所（有限公司） | Preparation method of bisphenol phosphate hydroxyl aluminum salt nucleating agents |
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| JPH08134260A (en) * | 1994-11-07 | 1996-05-28 | Asahi Denka Kogyo Kk | Crystalline synthetic resin composition |
| CN102807582A (en) * | 2011-06-02 | 2012-12-05 | 中国石油化工股份有限公司 | Preparation methods of organic phosphate ester and organic phosphate nucleating agent |
| CN102827205A (en) * | 2011-06-17 | 2012-12-19 | 中国石油化工股份有限公司 | Preparation method of nucleating agent |
| CN110734463A (en) * | 2019-10-16 | 2020-01-31 | 山西省化工研究所（有限公司） | Preparation method of bisphenol phosphate hydroxyl aluminum salt nucleating agents |
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