WO2007051377A1 - Hydrotalcite incorporant en couche un ou plusieurs anions organiques comprenant une double liaison et utilisation de celle-ci en tant que stabilisateur thermique - Google Patents

Hydrotalcite incorporant en couche un ou plusieurs anions organiques comprenant une double liaison et utilisation de celle-ci en tant que stabilisateur thermique Download PDF

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WO2007051377A1
WO2007051377A1 PCT/CN2006/001233 CN2006001233W WO2007051377A1 WO 2007051377 A1 WO2007051377 A1 WO 2007051377A1 CN 2006001233 W CN2006001233 W CN 2006001233W WO 2007051377 A1 WO2007051377 A1 WO 2007051377A1
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hydrotalcite
pvc
double bond
organic anion
intercalated
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PCT/CN2006/001233
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English (en)
Chinese (zh)
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Xue Duan
Dianqing Li
Yanjun Lin
Jianrong Wang
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Beijing University Of Chemical Technology
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Publication of WO2007051377A1 publication Critical patent/WO2007051377A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
    • C01F7/00—Compounds of aluminium
    • C01F7/78—Compounds containing aluminium and two or more other elements, with the exception of oxygen and hydrogen
    • C01F7/784—Layered double hydroxide, e.g. comprising nitrate, sulfate or carbonate ions as intercalating anions
    • C01F7/785—Hydrotalcite
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2002/00—Crystal-structural characteristics
    • C01P2002/20—Two-dimensional structures
    • C01P2002/22—Two-dimensional structures layered hydroxide-type, e.g. of the hydrotalcite-type
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2002/00—Crystal-structural characteristics
    • C01P2002/70—Crystal-structural characteristics defined by measured X-ray, neutron or electron diffraction data
    • C01P2002/72—Crystal-structural characteristics defined by measured X-ray, neutron or electron diffraction data by d-values or two theta-values, e.g. as X-ray diagram
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2002/00—Crystal-structural characteristics
    • C01P2002/80—Crystal-structural characteristics defined by measured data other than those specified in group C01P2002/70
    • C01P2002/82—Crystal-structural characteristics defined by measured data other than those specified in group C01P2002/70 by IR- or Raman-data
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2002/00—Crystal-structural characteristics
    • C01P2002/80—Crystal-structural characteristics defined by measured data other than those specified in group C01P2002/70
    • C01P2002/88—Crystal-structural characteristics defined by measured data other than those specified in group C01P2002/70 by thermal analysis data, e.g. TGA, DTA, DSC

Definitions

  • the present invention relates to a novel supramolecular intercalated hydrotalcite, in particular to a double bond organic anion intercalated hydrotalcite, and the hydrotalcite as a composite heat stabilizer for PVC.
  • PVC and other chlorine-containing polymers can undergo auto-catalytic reaction of de-HC1 under high temperature or under the influence of high-energy rays (such as ultraviolet rays).
  • the thermal decomposition mechanism is generally considered to be of three types: (1) Freedom in an oxygen-containing environment Base mechanism; (2) Ion mechanism in a nitrogen atmosphere; (3) Single molecule mechanism under vacuum conditions.
  • the thermal degradation of PVC is a very complicated process. The direct consequence of degradation is that the color becomes darker and the structure and properties of the product are greatly damaged.
  • Heat stabilizers are one of the main additives that are indispensable for the processing of PVC and other chlorine-containing polymers.
  • the heat stabilizer should have the following functions: 1. It can absorb and neutralize the HC1 released by PVC during the process, preventing its autocatalysis in the presence of oxygen, and generating non-ionic products; 2. It can stop the growth of unsaturated silent bonds by means of addition, reduction, oxidation or free radical reaction; 3. It has light stabilizing effect, can absorb and reflect ultraviolet rays, such as light shielding agent, ultraviolet absorber, quencher, Free radical trapping agent and other substances; 4, with PVC has good solubility, easy to manufacture transparent products; 5, should be colorless, odorless, non-toxic, non-migratory, moderate price, does not affect the rheology of PVC resin and its basic feature.
  • thermal stabilizers can be mainly classified into salt-based lead salts, metal soaps, organotins, rare earths and composite stabilizers according to their chemical structures.
  • PVC heat stabilizers are developing towards low toxicity, pollution-free and high efficiency. It is of great significance to develop and develop a new generation of environmentally-friendly PVC heat stabilizers.
  • Hydrotalcite also known as Layered Double Hydroxides (LDHs)
  • LDHs Layered Double Hydroxides
  • Interlayer C0 3 2 - can be exchanged with HC1 entering the layer to achieve absorption of HC1, stable PVC and other chlorine-containing polymers.
  • the cations of the laminate and the interlayer anions are modulated, and the elements which are beneficial to improve the thermal stability of the PVC are added, and a novel structure of the supramolecular intercalated hydrotalcite having a better thermal stability to PVC can be formed.
  • An object of the present invention is to provide an organic anion intercalated hydrotalcite containing a double bond; another object of the present invention is to use the hydrotalcite as a PVC heat stabilizer.
  • the double bond organic anion intercalated hydrotalcite provided by the invention has the chemical composition formula:
  • M 2+ represents one or both of divalent metal cations Mg 2+ , Zn 2+ , Ca 2+ , Cu 2 Ni 2+ , Co 2+ , Fe 2+ , Mn 2+ , Cd 2+ Preferred as one or both of Mg 2+ , Zn 2+ , and Ca 2+ ;
  • M 3+ represents one of a trivalent metal cation Al 3+ , Ni 3+ , Co 3+ , Fe 3+ , Mn 3+ , Cr 3+ , V 3+ , Ti 3+ , preferably Al 3 + or Ni 3+ ;
  • ⁇ ⁇ ⁇ is one of a double bond organic anion maleate, acrylate, butenoate, aminobutenoate, oleate, linoleate, linolenate, preferably maleate, acrylate or Butenoate
  • X is the mole fraction of M 3+ ions, and its value ranges from 0.2 ⁇ x 0.33 ;
  • m is the amount of crystal water, and its value ranges from 0 m ⁇ 2.
  • the preparation method of the organic-organic intercalated hydrotalcite containing the silent bond according to the present invention is as follows:
  • A. Dissolving M 2+ soluble nitrate and M 3+ soluble nitrate in a molar ratio of M 2+ /M 3+ of about 2 ⁇ 4 in deionized water de C0 2 to form a mixed salt solution , the concentration of M 2+ is 0.1 ⁇ 1.6mol / L; the ratio of the number of moles of NaOH to the total number of moles of metal ions in the mixed solution a ratio of about 1.8 to 2.5, dissolving NaOH in deionized water de C0 2 to prepare an equal volume of alkali solution with the mixed salt solution; adding the above two solutions to the reactor at the same time, reacting at room temperature for about 0.5-6 min, The obtained slurry is crystallized under the protection of N 2 at 60 to 100 ° C for about 3 to 8 hours, filtered, and washed with deco 2 deionized water to obtain a nitrate-type hydrotalcite precursor filter cake;
  • step B Dissolving a double-bond organic acid in ethylene glycol to prepare a solution having an organic acid content of about 10 to 50% by mass, and dispersing the nitrate-type hydrotalcite precursor prepared in step A in ethylene glycol.
  • the preparation of the hydrotalcite precursor has a mass percentage of 10% to 70%, and the ethylene glycol solution containing the organic acid is in a ratio of the organic acid to the hydrotalcite precursor in a molar ratio of about 1:1 to 5
  • the mixture is added dropwise to an ethylene glycol dispersion containing an aqueous talc precursor, and the reaction system is controlled to have a pH of 4.0, heated to a reflux temperature, and reacted for 0.5 to 6 hours. After washing and drying, an intercalated hydrotalcite is obtained.
  • M 2+ represents one of divalent metal cations Mg 2+ , Zn 2+ , Ca 2+ , Cu 2+ , Ni 2+ , Co 2+ , Fe 2+ , Mn 2+ , Cd 2+ Or two, preferably one or two of Mg 2+ , Zn 2+ , Ca 2+ ;
  • M 3+ represents a trivalent metal cation Al 3+ , Ni 3+ , Co 3+ , Fe 3+ One of Mn 3+ , Cr 3+ , V 3+ , Ti 3+ , preferably Al 3+ or Ni 3+ ;
  • the double bond-containing organic acid in the step B may be one of maleic acid, acrylic acid, crotonic acid, aminobutenoic acid, oleic acid, linoleic acid, and linolenic acid, preferably maleic acid or acrylic acid. Or butenoic acid.
  • the double bond-containing organic anion intercalated hydrotalcite prepared above was mixed with calcium stearate and zinc stearate and added to PVC for static heat aging test.
  • the results are shown in Table 1, indicating that the supramolecular insertion prepared by the present invention
  • the layer structure hydrotalcite can effectively improve the thermal stability of PVC, and is an excellent PVC heat stabilizer.
  • the reason is that the double bond in the molecule can react with the conjugated double bond generated by the decomposition of PVC to form a diene addition reaction, blocking the conjugate.
  • the continuation of the double bond destroys the autocatalytic decomposition of PVC and can significantly improve the thermal stability of PVC.
  • the present invention provides an organic anion intercalated hydrotalcite containing a double bond, which is used as a hydrotalcite
  • PVC heat stabilizer can significantly improve the thermal stability of PVC.
  • Fig. 1 is an XRD spectrum of a hydrotalcite precursor and a maleate intercalated hydrotalcite prepared in Example 1, wherein a is a curve of a hydrotalcite precursor and b is a curve of a maleate intercalated hydrotalcite.
  • Example 2 is an IR spectrum of a hydrotalcite precursor, maleic acid intercalated hydrotalcite, and maleic acid prepared in Example 2, wherein a is a curve of a hydrotalcite precursor, and b is a maleate intercalated hydrotalcite.
  • the curve, c is the curve of maleic acid.
  • Figure 3 is a TG-DTA spectrum of the maleate intercalation MgZnAl-LDHs prepared in Example 2. detailed description
  • Step B Disperse the above hydrotalcite precursor filter cake in 20 ml of ethylene glycol, dissolve 2.32 g of maleic acid in 3.0 ml of ethylene glycol, control pH>4.0, and add the ethylene glycol solution of maleic acid dropwise.
  • the ethylene glycol dispersion of the hydrotalcite precursor is heated to reflux temperature for 6 hours, washed and dried to obtain a maleic acid intercalated hydrotalcite.
  • the chemical formula is as follows: Mg 0 . 67 Al 0 . 33 (OH) 2 (C 4 H 2 O 4 ) 0 . 17 '0.6H 2 O.
  • Step A 8.20 g of Mg(N0 3 ) 2 ⁇ 6H 2 0, 3.17 g of Zn(N0 3 ) 2 ⁇ 6H 2 0 and 8.00 g of A1(N0 3 ) 3 ⁇ 9H 2 0 are dissolved in deionized C0 2 80 ml of a mixed salt solution was prepared in water, and 4.70 g of NaOH was dissolved in deionized water de-C0 2 to prepare 80 ml of an alkali solution.
  • Step B Disperse the above MgZnAl-N0 3 -LDHs precursor filter cake in 10 ml of ethylene glycol, and dissolve 4.96 g of maleic acid in 10 ml of ethylene glycol to control pH>4.0, maleic acid
  • the ethylene glycol solution is added dropwise to the ethylene glycol dispersion of the hydrotalcite precursor, heated to reflux, and reacted for 1 hour. After washing and drying, the maleic acid intercalated hydrotalcite is obtained and determined by elemental analysis.
  • the chemical formula is: M g0 50 Zn 0 . 17 Al 0 . 33 (OH) 2 (C 4 H 2 O 4 ) 0 . 17 . 0.53 ⁇ 4O.
  • Step A Dissolve 7.68 g of Mg(N0 3 ) 2 ⁇ 6H 2 0, 8.92 g of Zn(N0 3 ) 2 ' 6H 2 0 and 11.25 g of A1(N0 3 ) 3 ⁇ 9H 2 0 in deionized C0 2
  • 40 ml of a mixed salt solution was prepared in water, and 7.28 g of NaOH was dissolved in deionized water de C0 2 to prepare 40 ml of an alkali solution.
  • the two solutions were simultaneously added to the reactor for 4 min, and recrystallized at 100 ° C for 6 hours under N 2 protection.
  • Step B Disperse the above MgZnA O r LDHs precursor filter cake in 13 ml of ethylene glycol, dissolve 5.22 g of maleic acid in 9 ml of ethylene glycol, control pH>4.0, and drop the ethylene glycol solution of maleic acid.
  • the ethylene glycol dispersion of the hydrotalcite precursor was added, heated to reflux, and reacted for 4 hours, and washed and dried to obtain a maleic acid intercalated hydrotalcite.
  • the chemical formula is determined by elemental analysis: Mg 0 . 33 Zn 0 . 33 Al 0 . 33 (OH) 2 (C 4 H 2 O 4 ) 0 . 17 ⁇ 0 ⁇ 63 ⁇ 4 ⁇ .
  • Example 4 Example 4:
  • Step ⁇ 8.20 g Mg(N0 3 ) 2 ⁇ 6H 2 0, 3.17 g Zn(N0 3 ) 2 ⁇ 6H 2 0 and 4.00 g A1(N0 3 ) 3 ⁇ 9H 2 0 are dissolved in C ( 3 ⁇ 4 ) dubbed 40ml DI water mixed salt solution, 4.59 g NaOH dissolved in deionized water and C0 2 removal formulated 40ml of alkali solution.
  • Step B Disperse the above MgZnAl-N0 3 -LDHs precursor filter cake in 38 ml of ethylene glycol, and dissolve 3.09 g of maleic acid in 3.10 ml of ethylene glycol to control pH>4.0, and the maleic acid of ethylene
  • the alcohol solution was added dropwise to the ethylene glycol dispersion of the hydrotalcite precursor, heated to reflux, and reacted for 2 hours, and washed and dried to obtain a maleic acid intercalated hydrotalcite.
  • the chemical formula was determined by elemental analysis: Mgo.6oZno.2oAlo.2o(OH) 2 (C 4 H 2 04)on ⁇ 0.4H 2 O.
  • Example 5 Example 5:
  • Step A 8.20 g of Mg(N0 3 ) 2 ⁇ 6H 2 0, 2.53 g of Ca(N0 3 ) 2 ' 4H 2 0 and 5.14 g of Ni(N0 3 ) 3 were dissolved in deionized water de C0 2 to prepare 210.
  • the salt solution was mixed with ml, and 6.10 g of NaOH was dissolved in deionized water de C0 2 to prepare 210 ml of an alkali solution.
  • Step B Disperse the above MgCaNi-NO LDHs precursor filter cake in 30 ml of ethylene glycol, dissolve 4.05 g of maleic acid in 5.05 ml of ethylene glycol, control pH>4.0, and add ethylene glycol solution of maleic acid. The mixture was added dropwise to the ethylene glycol dispersion of the hydrotalcite precursor, heated to reflux, and reacted for 3 hours. After washing, the maleic acid intercalated hydrotalcite was obtained. The chemical formula was determined by elemental analysis: Mgo.5oCao.i7 io.33(OH) 2 (C 4 H 2 04)o. 1 7 ⁇ 0.7H 2 O.
  • Step B Disperse the above MgZnAl-N0 3 -LDHs precursor filter cake in 10 ml of ethylene glycol, dissolve 2.5 g of acrylic acid in 5 ml of ethylene glycol, control pH>4.0, and drop the ethylene glycol solution of acrylic acid. Adding to the ethylene glycol dispersion of the hydrotalcite precursor, heating to reflux, reacting for 6 hours, washing and drying to obtain an acrylic intercalated hydrotalcite, which is determined by elemental analysis and has the chemical formula: Mg 0 . 50 Zn 0 . 17 Al 0 . 33 (OH) 2 (C 3 H 2 O 4 ) 0 . 17 ' 0.53 ⁇ 4O.
  • Example 7 Example 7
  • Step B Disperse the above hydrotalcite precursor filter cake in 20 ml of ethylene glycol, dissolve 1.44 g of acrylic acid in 7.0 ml of ethylene glycol, control pH > 4.0, and add the ethylene glycol solution of acrylic acid to the hydrotalcite precursor.
  • the ethylene glycol dispersion was heated to reflux temperature for 6 hours, washed and dried to obtain an acrylic intercalated hydrotalcite.
  • the chemical formula is as follows: Mg 0 . 67 Al 0 . 33 (OH) 2 (C 3 H 2 O 4 ) 0 . 17 ⁇ 0 ⁇ 6 ⁇ 2 ⁇ . Comparative example:
  • the double bond anion intercalated hydrotalcite obtained in Examples 1-7 and the common magnesium aluminum hydrotalcite were respectively obtained.
  • the chemical formula is Mgo. 67 Alo. 33 (OH)(C0 3 )o. 17 ⁇ 0.4H 2 O ) is added to 100 parts of PVC according to the amount listed in Table 1, and 50 parts of phthalic acid is added.
  • a 1 mm sheet was cut into pieces of 1 cm x 1 cm.
  • the test piece was placed in a heat aging test chamber at 180 ⁇ 1 ° C for static aging test, and the time at which the black decomposition of the test piece began to appear was set as the heat stabilization time, and the results are shown in Table 1.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • Inorganic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)

Abstract

L’invention concerne une hydrotalcite incorporant en couche un ou plusieurs anions organiques comprenant une double liaison, laquelle répond à la formule suivante : [M2+1-xM3+x(OH)2]An-x/n mH2O, dans laquelle An- représente un ou plusieurs anions organiques comprenant une double liaison sélectionnés parmi un maléate, un acrylate et un vinylacétate. Comme la double liaison contenue dans l'hydrotalcite peut réagir avec les doubles liaisons conjuguées produites par la décomposition du PVC, l'hydrotalcite de l'invention peut améliorer remarquablement la stabilité thermique à long terme du PVC. Le résultat de l'essai de vieillissement thermique en statique effectué sur du PVC incorporant l'hydrotalcite, du stéarate de calcium et du stéarate de zinc, montre que l'hydrotalcite peut accroître sensiblement la stabilité thermique du PVC et qu'elle est donc un excellent stabilisateur thermique du PVC.
PCT/CN2006/001233 2005-11-03 2006-06-07 Hydrotalcite incorporant en couche un ou plusieurs anions organiques comprenant une double liaison et utilisation de celle-ci en tant que stabilisateur thermique WO2007051377A1 (fr)

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Cited By (1)

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US8088349B2 (en) 2007-01-12 2012-01-03 Beijing University Of Chemical Technology Clean method for preparing layered double hydroxides

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CN108193552A (zh) * 2017-12-07 2018-06-22 常州市沃兰特电子有限公司 一种水溶性纸张纤维用光稳定剂的制备方法
CN114806674A (zh) * 2022-04-24 2022-07-29 北京化工大学 一种稠化剂插层水滑石及制备方法和作为润滑脂稠化剂的应用

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