• 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:
    1486790 Polyurethanes; polyureas SCHERING AG 8 Nov 1974 [10 Nov 1973] 48484/74 Addition to 1394732 Heading C3R [Also in Division C2] A compound (C) is obtainable by reacting a polyisocyanate (I) with a compound containing #1 ketimine group and #1 OH group, but not containing an enamine group, mole ratio NCO : OH being 1 : 1. A prepolymer (P) is made by reacting a compound containing #1 NH 2 and #1 OH group with an aliphatic or cyclic ketone and removing the water formed and any excess carbonyl compounds, and reacting the product with a polyisocyanate (I), mole ratio NCO : OH being 1 : 1. (I) may be an aliphatic diisocyanate, or an adduct of a polyhydroxy compound and excess of a polyisocyanate. A polyurea may be made from a preparation comprising a polyisocyanate and compound (C) or prepolymer (P) by mixing with water or exposure to water or water vapour, e.g. as atmospheric moisture. Examples employ ethanolamine, diethyleneglycolamine, hexanolamine-1,6, MIK, cyclohexanone, trifunctional polypropylene glycol, and isophorone diisocyanate; ketimines have formulµ
    公开号:SU743583A3
    申请号:SU742061351
    申请日:1974-09-18
    公开日:1980-06-25
    发明作者:Бринкманн Бернд；Грибш Ойген
    申请人:Шеринг Аг (Фирма)；
    IPC主号:
    专利说明:

    (54) METHOD FOR OBTAINING A POLYMER MATERIAL The invention relates to the preparation of a polymeric material that can be widely used in various industries. A method of producing a polymeric material by reacting a polyisocyanate with a compound containing one imine and one hydroxyl group and ketone in solvent 1 is known. However, with the simultaneous introduction of ketimines containing a hydroxyl group with a polyisocyanate and ketoi, the structure of ketimine does not preserve the urethia group. not formed. The aim of the invention is to reduce the curing time. This is achieved by first performing a reaction between a compound containing one imine and one g of oxyl group and a ketone, then introducing a polyisocyanate at an NCO / OH-rpynn ratio of 1 followed by treating the ketimine with a polyisocyanate in the presence of atmospheric moisture or with the addition of an equivalent amount in this process, ketimines containing hydroxy groups are attached to the isocyanates to form urethane groups while maintaining the structure of ketimine. The preparation of ketimines occurs so that the primary ones are mixed with an excess of the carbonyl component and, after adding the appropriate solvent (toluene, benzene), is heated in a nitrogen atmosphere with water separation until the evolution of water is complete. In some cases, the carbonyl containing component itself may serve as a carrier. Destilli q ketimine is beneficial. The feed may be applied directly after removing the excess carbonyl containing component and solvent. Aliphatic and cyclic ketones are particularly suitable as carbonyl-containing component. Ketones that are beneficial for the preparation of ketimine: cyclopentanone, trimethylcyclopentanone, cyclohexanone, trimethylcyclohexanone and other substituted cyclohexanone and cyclopentatones, as well as methyl isobutyl ketone, methyl ethyl ketone, diethyl ketone, diisopropyl ketone, etc. For addition of ketimines containing hydroxyl groups, pre-adducts of polypropylene glycols and excess aliphatic diisocyanates can be used. In polypropylene glycols, these are linear or branched products with an average molecular weight ranging from 500 to 10,000. It is advantageous to use aliphatic diisocyanates with isocyanate groups of different reactivity, since this eliminates chain elongation. Such diisocyanates are, for example, isophorone diisocyanate and trimethyl hexamethylene diisocyanate. In cases where chain extension is desired, hexamethylene diisocyanate, 1-methyl-2,4 diisocyanic tocyclohexane or 4,4-di-eocyanatodicyclohexylmethane can also be used.
    Diisocyanates are added predominantly at a ratio of isocyanate groups to hydroxyl groups 1.8-2. It is advisable to mix the components while cooling at 0-30 ° C and add a catalyst, for example organic tin compounds or tertiary amines. After that, the mixture is heated to elevated temperatures, preferably 50-100s, until the isocyanate content determined analytically corresponds to the calculated value.
    Ketimines, the content of the hydroxyl group, are mixed with the pre-adduct of the isocyanate predominantly in the ratio of NCO / OH equal to 1. The introduction into the mixture should take place with vigorous stirring and, if necessary, during cooling at temperatures as low as. This occurs as long as infrared spectroscopy is not possible - more than about. expose free isocyanate.
    Ketimine adducts can be used as amine-cleaving compounds, for example, for wet curable polyurethane materials. For this purpose, they are mixed with modified aromatic polyisocyanates in an approximately stoichiometric ratio. For example, addition products from trimethylolpropane and 2,4-toluene diisocyanate in a 151th ratio of 1: 3 are used as modified polyisocyanates, and free isocyanate groups can be modified with phenol.
    Example.
    A. A 1 L three-necked flask with a water trap and a stirrer is charged with 91.5 g of ethanolamine, 225 g of methyl isobutyl ketone and 100 ml of benzene. The mixture is heated at reflux until a calculated amount of water is released. The excess ketone is then withdrawn and
    the solvents and the precipitate are distilled in vacuo. Cr. 5 mm.
    Calculated,%: with 67; H 11.0; N 9,8
    Found,%: C 66.8; H 12.1; N 9.8.
    3 infrared spectrum is
    -i ketimine band strong at 1655 cm
    Reaction product formula
    , SI,
    . “H
    BUT-CH-CHA-M S
    Sn, -Snz B. A mixture containing 5040 g of three O functional polypropylene glycol with the number OH 35.6 and 711 g of isophorone diisocyanate is mixed with 5.7 g of dibutyl tin dilaurate and stirred for 3 hours at 75 ° C under a nitrogen atmosphere 5. The reaction product has an isocyanate content of 2.2 wt.%, In accordance with the atomic weight of 1914.
    C. 1000 g of prepolymers containing the obtained. In Example 1B of the Q group of the isocyanate are mixed, with cooling, with 74.83 g of ketimine containing the hydroxyl groups obtained in Example 1A. With vigorous stirring should pay attention to - so that the temperature does not exceed 30 ° C. After 4-5 hours of stirring in the infrared spectrum, free isocyanate cannot be detected anymore. In contrast, the kathimine band is maintained. The product has an equivalent weight of 2057. 0 Example2.A. A mixture containing 105 g of diglycolamine and 150 g of cyclohexanoHa is mixed with 100 ml of benzene and heated on a water separator for 4 hours. 17.6 g 5 of water are released. The excess ketone and solvent are liberated and the residue (residue) is distilled in vacuo. Cr. 103C / 0.2 mm. Calculated,%: C 64.8; H 10.3; N 7.6. Found.%: C 64.8; .H10.3; N 8,0, 0 The reaction product has the formula
    НО-СН „СН2 О-СН, ССН, К-О. c, 1000 g of the prepolymer containing the isocyanate groups prepared according to example 1B are mixed, with cooling and vigorous stirring, with 96.6 g of ketimine prepared according to example 2A. The temperature during the reaction is established. below. After 5 hours of stirring in the infrared spectrum, it is not possible to detect free isocyanate more. The product has an equivalent weight of 2100.
    PRI me R 3.
    A, 324 g of diglycolamine are mixed. with 300.5 g of methyl isobutyl ketone and 55 300 ml of benzene. The mixture is heated at a water separator under a nitrogen atmosphere until the evolution of water is complete. The solvent is removed and the precipitate is distilled in vacuo. The reaction product has the Formula
    CH
    BUT-SNG-CHGO-SNG-m with / CH CHj-CH.
    权利要求:
    Claims (1)
    [1]
    B, lOOOr prepolymer containing the eosocyanate groups prepared according to example 1B, is mixed with stirring and cooling with 97.8 g ketimy prepared according to example 3a. After 4 hours of stirring by examination. in the infrared spectrum, free isocyanate cannot be detected. The product has an equivalent weight of 2012. EXAMPLE 4. A 117 g of hexanolamine-1, b is heated together with 150 g of cyclohexanone and 100 ml of benzene at a water separator until more reaction water is formed. Reaction finish approximately After V6 hours. The remaining (surplus) ketone and benzene are removed by vacuum and the residue is distilled in vacuum. Cr. 153 ° C / 0.8 mm. Found,%: C 73.5; H 11.7; N 6 Calculated: С 73.0; H 11.7; N 7 The infrared spectrum detects a strong band at 1660 cm. The reaction product has the formula HO- (CH) g -NO. B. 1536 branched polypropylene glycol with an OH number of 35.6 is mixed with 221 g of isophorone diisocyanate. and 1.8 g of dibutyl tin dilaurate. The reaction mixture is heated to 2.5 hours with thorough stirring; 1 is kept at this temperature. The reaction product has an isocyanate content of 2.39%. at. 1000 g of prepolymer isocyanate obtained in Example 4B are mixed with 112.2 g of ketimine containing the hydroxyl groups obtained in Example 4A at room temperature. After the mixture has been standing for approximately 12 hours, no free isocyanate can be detected in the infrared spectrum. DETAILED DESCRIPTION OF THE INVENTION A method for producing a polymeric material is hereby reacting a polyisocyanate with a compound containing one amine and one hydroxyl group and a ketone in a solvent medium, characterized in that, in order to shorten the curing process, the reaction between the compound containing one amine and one is first performed. hydroxyl groups, and ketone, then the polyisocyanate is introduced with an NCO / OH-rpynn ratio of 1 followed by. treatment of ketimine with a polyisocyanate in the presence of atmospheric moisture or with the addition of an equivalent amount of water. Sources of information taken into account in the examination 1. Patent of England 1064841, cl. C 3 R, pub. 1967 (prototype).
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    同族专利:
    公开号 | 公开日
    JPS5079599A|1975-06-28|
    GB1486790A|1977-09-21|
    AT339606B|1977-10-25|
    DE2356213A1|1975-05-15|
    SE421523B|1982-01-04|
    FR2257620B2|1978-06-23|
    BE822013A|1975-05-09|
    DE2356213C2|1986-11-13|
    SE7414020L|1975-05-11|
    FR2257620A2|1975-08-08|
    NL7414636A|1975-05-13|
    JPS5811894B2|1983-03-05|
    ATA890474A|1977-02-15|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    DE2125247C3|1971-04-06|1981-07-23|Schering Ag Berlin Und Bergkamen, 1000 Berlin|Process for the application of paints, casting compounds, leveling compounds, coverings and coating compounds|DE2546536A1|1975-10-17|1977-04-28|Bayer Ag|HIGH MOLECULAR POLYAMINE AND THE PROCESS FOR THEIR PRODUCTION|
    DE2651479C2|1976-11-11|1986-03-20|Schering AG, 1000 Berlin und 4709 Bergkamen|Elastic adhesive|
    JPS59161292U|1983-03-24|1984-10-29|
    JPS64720Y2|1983-03-24|1989-01-09|
    DE4311901A1|1993-04-10|1994-10-13|Huels Chemische Werke Ag|New azeomethines, a process for their preparation and their use|
    US20140275464A1|2005-09-15|2014-09-18|The Government Of The United States Of America, As Represented By The Secretary Of The Navy|Polyenureas and method of making the same|
    US8735526B2|2005-09-15|2014-05-27|The United States Of America, As Represented By The Secretary Of The Navy|Polyenureas and method of making the same|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE19732356213|DE2356213C2|1973-11-10|1973-11-10|Prepolymers terminated by ketimine groups and processes for their preparation|
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