• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    1471101 Polymerisation catalyst UPJOHN CO 3 Jan 1975 [30 Jan 1974] 250/75 Heading B1E [Also in Divisions B5, C2 and C3] A catalyst composition for the trimerisation of a polyisocyanate and of use in the formation of cellular isocyanurate polymers comprises (a) 33 to 67 mole % of an amide salt of formula wherein: M is Li, Na or K; R 1 , R 2 and R 3 are H, C 1 -C 8 alkyl, aryl, aralkyl or cycloalkyl; R 4 is C 1 -C 8 alkyl or aryl, and (b) 33 to 67 mole % of a glycine salt of formula wherein: M is Li, Na or K; R 5 is H or C 1 -C 12 alkyl; R 6 is H, C 1 -C 12 alkyl or CH 2 COOM; and R 7 is H or CH 2 N(R 6 )CH 2 COOM. The composition may further comprise a tertiary amine isocyanate-trimerisation catalyst in an amount of 1 to 50% wt based on the total of components (a) and (b). Component (a) may be potassium N-phenyl-2-ethylhexamide and component (b) may be sodium N-(2-hydroxy- 5-nonylphenyl)-methyl-N-methylglycinate. The amide salt and glycine salts may be used as solutions in diluents, e.g. a mixture of ethylene glycol and dimethylformamide. The tertiary amine may be N, N-dimethyl-ethanolamine, -benzylamine or -cyclohexylamine; N, N, N', N'-tetramethyl-1, 3-butanediamine or -propanediamine; N-methylmorpholine or N-ethylmorpholine.
    公开号:SU946405A3
    申请号:SU752104655
    申请日:1975-01-29
    公开日:1982-07-23
    发明作者:Джон Локвуд Роберт；Юджин Реймоур Гарольд (Младший)；Джозеф Томпсон Эдвард
    申请人:Дзе Апджон Компани (Фирма)；
    IPC主号:
    专利说明:

    one
    The invention relates to the preparation of cellular polymers.
    A known method for the preparation of cellular polymers by mixing the polyester with a catalyst, emulsifier and water, followed by the addition of toluoyl diisocyanate with stirring. Phenolates, methyl and ethyl morpholines, pyridine, dimethylaniline are used as catalysts for the reaction of the reaction of diisocyanate with hydroxyl groups of polyether. The emulsifiers are sodium salts of sulfonic acids, various LO soaps The closest to the present is a method for preparing a cellular polymer, in which the main repeating unit is isocyanurate, by contacting the polyisocyanate with a trimerization catalyst in the presence of a polyhydric alcohol and a blowing agent 2.
    However, the cellular polymer obtained in a known manner has insufficiently high adhesion and physical strength.
    The purpose of the invention is to develop a method for producing a cellular polymer with 5 improved adhesion and physical strength.
    This goal is achieved in that the preparation of a cellular polymer, in which the main repeating unit 0 is isocyanurate, is carried out by co-contacting the polyisocyanate with a trimerization catalyst in the presence of a polyhydric alcohol and a blowing agent, with the following ingredients being used as a catalyst:
    a) amide salts of general formula
      E © RI CON
    20 R
    where M is an alkali metal; .tRlf identical or different radicals selected from the group consisting of hydrogen, lower alkyl, aryl, aralkyl, cycloalkyl; Take precautions to protect against atmospheric moisture. The preferred form of the amide salt is potassium M-phenyl-2-ethylhexamide. This salt is used in a catalyst in conjunction with a diluent, which can be a solvent or a mixture of solvents used in it. the preparation of an amide salt, for example ethylene glycol, diethylene glycol, polyethylene glycol-00.0, mixtures thereof, and also mixtures thereof with dimethylformamide. Particularly preferred is a mixture of ethylene glycol and dimethylformamide. The concentration of salt in the diluent is not critical and can range from 25 to 75 pounds. When using a mixture of diluents, one introduces in the amount of 10-90 wt., Another 25-75.% By weight. The second component of the catalyst, 20 namely the glycine salt, is obtained by contacting, under the reaction conditions, a Mannich-corresponding phenol of the formula with formaldehyde in a solvent medium with the corresponding alkali-metal glycine salt of the formula 25 S diethanolamine, triethanolamine; and dipolar aprotic solvents, such as dimethylmormamide, dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, and the like. and mixtures of any of these solvents. The salt obtained is expediently left in the reaction solution for use in the catalyst, but if desired it can be isolated from the solvent. Typical of the starting phenols are phenol, y1-cresol, H-butyl phenol, l-heptylphenol, i-octylphenol, i-nonylphenol, 1-decylphenol and ft-dodecylphenol. Typical glycine salts of sodium include sodium glycinate, potassium glycinate, lithium glycinate, sodium N-methylglycinate, sodium N-butylglycinate, sodium N-octylglycinate, sodium N-dodecylglycinate, disodium iminodiacetate, and the like. In the preparation of the glycine salt, the reagents are introduced in a phenol-formaldehyde ratio: a derivative of glycine 1: 1: 1 - 1: 2: 2. A particularly preferred salt of glyxine is N- (2-hydroxy-5-nonylphenyl) -methyl-M-sodium methylglycinate. The glycine salt is preferably used in combination with a thinning agent during combustion. Greater resistance to delamination and volume change under elevated temperature conditions allows the use of laminated tile material, in particular, for roofing, in cases where the material is exposed to temperatures over a wide range. The method is carried out as follows. Determination of acidity. 2 g of the isocyanate to be analyzed are mixed with 75 ml of toluene and 75 ml of methanol in a 250 ml beaker. The beaker was covered with a watch glass and the mixture was heated for 5 minutes at the boiling point with stirring. The mixture is then allowed to cool (% acidic acid equivalent. Preparation T. Sodium salt N- (, 2-Ci-5 Nonylphenyl) methyl-methyl glycine C // CHg-N-CHg- / Va) The apparatus for preparing this drug is A three-necked three-liter flask equipped with a stirrer, a nitrogen purge tube, a thermometer, and a cooler with a receiver. The flask was charged with 3.85 g of diethylene stake, 410 g (1.86 moles of nonylphenol, b75 g of an aqueous solution of sodium N-methylglycinate containing 32% by weight salts Ul6 g or 1.9 mol. The mixture is heated with vigorous stirring and atmospheric pressure to 135 D and most of the water is distilled. The flasks are heated to 110-120 ° 5 at room temperature. The mixture is titrated at a constant rate of 0.02 N. A solution of potassium hydroxide in methanol to a pH of 7.7. A standard blind ex- is carried out. Periment with a mixture of 75 ml of toluene and 75 ml of methanol (as described). The acid content of the isocyanate is calculated by the equation% acid (AB = 0.0365, where L is the amount of caustic potash consumed in the titration of the mixture with isocyanaton; B is the amount of caustic potash consumed in the titration of a standard blind sample,. Number of equivalents The acids contained in this sample of polyisocyanate are determined by the formula (s) grams. isocyanate -oZ-p at atmospheric pressure, while driving off most of the water. The vacuum is gradually connected, bringing the residual pressure to 3 mm Hg: and the temperature to 95-120 ° C, while the remainder of the water and volatile substances are distilled off. 255 g of diethylene glycol is poured in with a stirring, with quantitative yield M- (2-hydroxy-5 nonylphenyl) methyl cmethyl glycinate sodium in the form of a 50% solution in diethylene glycol. The hydroxyl equivalent is 90. The viscosity at 25 ° C is 13 ,. The solution of tlycinate can be used directly as a component of the catalyst. The salt is obtained as a semi-crystalline orange substance after the distillation of diethylene glycol from the solution in vacuo. Selected salt is also used as a component of the catalyst. Preparations 2-13. In the described manner, replacing phenols, amino acid salts and formaldehyde with solvents with the compounds listed in tab. 15 receive the corresponding salts of glycine and iminodiacetic acid. Note: 1- sodium glycinate; 2-35% solution of ethylene glycol in polyethylene glycol-400; 3-ethylene glycol; - sodium sarcosinate; 5 dipotassium iodine diacetate; 6 - butylcarbitol; 7 potassium glycinate; 8 - potassium sarcosinate ,,
    Preparation 14. The preparation conditions are the same as for Preparation 1. 201 g (1.86 mol (p-cresol, 180 g diethylene glycol, 675 g of an aqueous solution of sodium N-methylglycinate, containing 32 weight L salt (216 g or 1, 9 mol) and most of the water is distilled off. Within half an hour, 160 g of a 37% aqueous formaldehyde solution are poured in, which corresponds to 59.2 g (l, 95 mol) of formaldehyde. The reaction mixture is heated and the volatile substances are distilled off under vacuum. 250 g of diethylene glycol are added to the viscous residue with stirring to obtain N- (2-hydroxy-5 methylphenium L) methane -M-methyl glycinate sodium with a quantitative yield of v. A 50% solution in diethylene glycol. Hydroxyl equivalent 80. Preparation 15. 1 Phenyl-2-ethylhexamide potassium H.CW-CN The device for the preparation of this device is a three-necked flask, equipped with a mechanical stirrer, a thermometer, a charging funnel, a gas supply tube, the device is thoroughly dried, then 182.2 g (mol. of potassium ethyl hexanoate, dissolved in 168 g of ethylene glycol) are charged. Slowly, dropwise, while constantly stirring under weak addition of nitrogen, 119 (1 g (1 mol) of phenyl; isocyanate) are poured. The reaction is exothermic, the temperature rises until carbon dioxide is released.
    When cooled, small crystals begin to fall out of the resulting clear solution. However, with the addition of 1-75 g of dimethylformamide, a clear yellow solution is formed which has the following properties: equivalent weight 1I, acid number 3, viscosity at 53. This solution can be used directly as a component of the catalyst. The crude salt is obtained by distilling off ethylene glycol and dimethylformamide at the temperature of the steam bath and a residual pressure of 0.2 mm Hg. when protecting the product from atmospheric moisture. A semicrystalline orange residue weighing 275 g remains. It is stored in a vacuum desiccator until used as a component of the catalyst.
    Drug 1b. N-Butyl-2-etilexamide potassium.
    ®

    II1 1 -CH-C-N -C HQ
    182.2 g (1 mol) of potassium 2-ethylcapronate dissolved in 15 g of ethylene glycol are loaded into a one-liter three-neck flask similar to that described for preparation of preparation 15. Slowly, dropwise, with constant stirring, 99.1 g (1 mol of Putilisocyanate) are poured.
    As the temperature rises to 50 ° C, carbon dioxide is released. In the image of the yellow transparent solution, an increase in viscosity is noted compared with the initial solution. It has the following properties: equivalent weight 90, acid number 3.8. This solution can be used as a component of the catalyst. The crude salt is obtained by distilling off ethylene glycol by heating the solution at the temperature of the steam bath at a residual pressure of 0.2 mm Hg. and protection from atmospheric moisture. The residue is a semi-crystalline substance weighing 2–7 g. Until used as a component of the catalyst, it is kept in a vacuum desiccator.
    Preparations 17-28, using the preparation method of preparation 15, taking 168 g of ethylene glycol and 175 g of dimethylformamide as cosolvents as co-solvents, replacing the alkali metal salt of carboxylic acid and organic isocyanate with the compounds listed in table. 2, solamides are obtained. The solvent of salts consists of CH, wt.% Ethylene glycol and 51 wt.% Of dimethylformamide. Distillation of the solvent to obtain the crude amide salt is easily accomplished by heating the solution under vacuum.
    Thalum 2 N- (h-Tolyl) -2-ethylhexamide H- (alpha-Naphthyl) -2-ethylhexamide lithium N- ((-Biphenylyl) -decanoic potassium N-Phenyl-beta-phenylpropion 57 potassium
    13
    26
    Potassium Cyclohexylacetate Preparations. According to the procedure described for the preparation of the preparation 15 in 158 g of ethylene glycol as a solvent, replacing the potassium salt of carboxylic acid and organic isocyanate with those listed in Table. 2 compounds give the corresponding amide salts. Salts are characterized by a solvent content of ethylene glycol. Distillation of the solvent under vacuum gives the crude amide salt. Example 1. Highly resistant to temperature rigid laminated foams are prepared in accordance with the data given in Table. At the same time, the Admiral ... Incorp lamination machine is used with the temperatures of components A, B, and C, respectively, 15, 66, 15, 66, and 25, 26 C. Productivity 9, kg / min with a modified three-stage conical mixer operating at 4000 rev. / min, with a diameter of the exhaust nozzle of 6.35 mm. Conveyor speed 6.7-7.01 m / min. The air temperature in the curing chamber is 93.33 ° C. Laminated material 25 mm thick. Alumi
    and
    continuation of the table. 2
    - -N-Phenylcyclohexylacetamide57
    A 0.033 mm thick potassium foil is applied to both surfaces of the foam A using a capstock lining on the foam B and C. Given in Table. 3, physical foam test data relates to internal or core foam after removal of the facing material. Therefore, the facing material does not affect the indicated data. Component A, consisting of an organic polyisocyanate, is obtained by treating polymethylene polyphenyl polyisocyanate containing AO weight. methylenebis (phenyl isocyanate), a small amount of monomeric epoxy compound. The resulting polyisocyanate has an isocyanate equivalent and 0.07 acidity. Component A also contains a surfactant and freon. Component B is a polyol component, and component C contains a catalyst for producing polymer. Foams A, B and C in the table. 3 illustrates three laminated foams made using three different polyol components.
    Component L Polyisocyanate
    -zu
    g
    Freon -P-V
    Component B
    Polyester
    . Karbovaks-BPP Complex polyether Polyol Firol CiiF
    S
    DO-193
    Freon PB Component C
    Catalyst. I
    .
    Catalyst I
    PPC-1025
    Fi roll gray
    Sedimentation
    Initiation with
    Gelation, with
    Rise, min; with

    No stickiness
    Cure, min; s
    Density, g / cm
    Compressive stress
    l .
    And before lifting
    I to lift 1,237
    one
    Oxygen index 30.3
    j | 4 Fragility (weight loss,% 4.5
    Table 3
    13
    one
    25
    15 27
    ten
    1 9 1 8
    five
    1.7 19 54
    65
    B40
    1:75 0.033
    2.391 0.773 2.391 V
    Aging during dry drying at 93.3 C, I 1- 231 about k 56789101112131А 3 .5
    -1.5
    3.2
    5.2
    3.8
    -2,0
    3.6
    5, i note, Lj-53 0: hard surface-active polystyrene foam, supplied by Union Carbide Corp., freon PB: trichloromethane, manufactured by DuPont; polyester 1: a mixture of 24.8 parts of the ethereal product mol of chlorendic anhydride. 1.1 mol of diethylene glycol and 2.5 mol of hydroxy propylene with 2.2 parts of diethylene glycol; Carbowax-OO; polyethylene glycol mol. weight 570-630, manufactured by Union Carbide, a complex polyester-2: obtained by esterification of 1 mol of chlorendic anhydride, 1.1 mol of diethylene glycol and 2.5 mol of propylene oxide; polyol: consists of a mixture of 10 parts of a polyol obtained by reacting 3 Moles of ethylene oxide with trimethylolpropane (equivalent to EZ i and 10 hours of polyol with an equivalent of 133 and an average functionality of 5.3. which is a mixture of a) propylene oxide adduct and a mixture of polybenyl polyamine with a methylene bridge, representing the finished product of the condensation of aniline with formaldehyde in an acidic environment and adduct of glycerin b and propylene oxide; Firol CEF: Tris- (tetrachloroethyl) phosphato; DS-193: surface-active polysiloxane, manufactured by Dow Corning, catalyst 1: solution of h3 weight. | Potassium M-phenyl-2-ethylhexamide, 28% by weight ethylene glycol and 29% by weight of dimethylformamide; catalyst 2: solution of N- (2-hydroxy-5 nonylphenyl methyl-β-methylglycinate sodium in diethylene glycol; PPC-1025; propylene glycol, manufactured by Jefferson Chemical Co., with eV 500 and functionality 2; CP-3001: polypropoxylated glycerol with 1000, functionality 3 and partly with terminal-primary hydroxy groups. Dow Chemical Co., Ltd.; A5TM D-2863 flammability test. Determining the percentage of oxygen required to maintain the burning of the sample; xpyfiKOcTb (fragility): weight loss .% of sample, determined by ASTM C- (21. P, and measure 2. Foam P from the table is an example of a highly heat-resistant rigid laminated foam, obtained according to the method described in Example 1. The facing layer is aluminum foil of 0.038 mm, but test data is the same as for a heart-shaped foam (see example T.). In this case, a low-acid polyisocyanate is used (according to the described 7 and, moreover, a monomeric polyepoxide compound, which results in a material with a better resistance to aging when dry heated compared to the foam and from Example 1, Table
    Component C
    Catalyst 1
    Catalyst 2
    Settlement cream, with
    Initiation with
    Gelation, with
    Rise with
    Cure, with
    Lack of stickiness, with
    Note.
    polyester 3 consists of
    , 8 parts of the esterification product 1 mol of chloro-endic anhydride, 1.1 mol of diethylene glycol and 2.5 mol of propylene oxide mixed with 8 parts of polyol obtained by reacting 3 mol of ethylene oxide with trimethylpropane (equivalent to EZ) and 2.2 parts of diethylene glycol .
    DE-431: epoxidized Dow resin, viscosity / 6500 cP.
    Example 3. E and F foams from Table 5 are examples of highly heat-resistant rigid laminated foams obtained by the method described in Example 1. In both cases aluminum is the facing material. Aluminum foil is 1.5 mm thick. Upon receipt of the foam E and use a low acid polyisocyanate, similar to that used in the previous examples, and, in addition.
    21 lt6kOS22
    an additional component is added — more highly resistant to thermally tertiary amine, which catalyzes tricking deformation than previous foam formations. Foam material possesses bea materials.
    Component L
    Polyisocyanate
     ,
    Freon PB
    Firol r.EF Component B
    Polyester
    Carbovax-400
    SHE- (31
    DS-193
    Freon PB Component C
    Catalyst 1
    Catalyst 2
    N-Ethylmorpholine
    N, M-DimethylcycloKarbovax-AO Settlement cream Initiation, with Gelation, with Lifting, with Curing, with Lack of stickiness
    Density, g / cm
    Compressive stress, kg / cm
    Table5
    13
    25
    23
    IMECHANE
    Carbowax-tOO: polyethylene glycol with
    a pier weight. tOO, manufactured by Union Carbide,
    权利要求:
    Claims (2)
    [1]
    E-Hi + CfSR): sample flame spraying rate, determined according to ASTM E-8A (Tunnel Test). Claim 1. Method for preparing a cellular polymer, in which isocyanurate serves as the main repeating unit, by contacting the polyisocyanate with a trimerization catalyst in the presence of a polyhydric alcohol and a blowing agent, characterized in that, in order to obtain a polymer with improved adhesion and physical strength, as a catalyst use a combination of the following ingredients: a) amide salts of the general formula
    .®
    e,
    - C-CON R4
    /
    ) 24
    Continued table. 5 per ra and ap
    in which M is an alkali metal;
    Rj is hydrogen or alkyl with 1-12 carbon atoms. which And - alkali metal; .% identical or different diols selected from the group including hydrogen, lower alkyl, aryl, alkyl, cycloalkyl; R is lower alkyl or aryl b) salts of glycine of the general formula f N-6Hg – COOn 25 Rg are hydrogen or alkyl with 1–12 hazardous atoms or the group —CH.j. – COO M. R7 is hydrogen or the group 14 -CH-N-CHa-COO®AL® in the following ratio of ingredients: a) amide salts from 0.0017 to 0.026 equivalents per equivalent of polyisocyanate; b) a glycine salt of 0.0033 to 0.0 equivalent per equivalent of polyisocyanate, and polymethylene polyphenyl isocyanate containing 30-P5 methylenebis (phenyl isocyanate) is taken as polyisocyanate. 2. The method according to claim 1, characterized by the fact that M-phenyl-2-ethylhexyl potassium amide is used as co-amide. 3. The method according to claim 1, distinguishes y, and also with the fact that M- (2-hydroxy-3-nonylphenyl methyl-M-methyl glycinate sodium is used as the glycine salt. 5. The method of claim 1, about t and that with the fact that the amide salt is used in the form of a 25-75% solution in a mixture of ethylene glycol and dimethyl form of the amide, 5. The method according to claim 1, which is different from the fact that the salt of glycine is used in the form 25-75 - 6. A method according to claim 1, characterized in that it uses a blowing agent containing from 0.01 to 0.1 equivalents of monomeric polyepoxide per equivalent of polyisocyanate. 7. The method according to claim 6, is different using a blowing agent containing 0.0009-0.01 equivalents of tertiary, amine per equivalent of polyisation, Sources of information taken into account during the examination 1.Nikolaev AF Synthetic polymers and plastics based on them. Chemistry, pp. 6 + 9.
    [2]
    2. The patent of Germany No. 1720953, cl. C 08 F 22 / kk, published 1972 (prototype).
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    同族专利:
    公开号 | 公开日
    GB1471101A|1977-04-21|
    DD121122A5|1976-07-12|
    AU7692874A|1976-07-01|
    BE825012A|1975-07-30|
    US3896052A|1975-07-22|
    JPS50109295A|1975-08-28|
    CA1037647A|1978-08-29|
    JPS5243760B2|1977-11-01|
    DE2502330C2|1982-11-04|
    DE2502330A1|1975-08-07|
    DD121119A5|1976-07-12|
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    法律状态:
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    申请号 | 申请日 | 专利标题
    US437780A|US3896052A|1974-01-30|1974-01-30|Cocatalyst system for trimerizing polyisocyanates|
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