• 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:
    METHOD OF OBTAINING POLYISOCYANATE-POLYISOCYANATE by cycling aliphatic diisocyanates of the general formula OCN-Z-NCO where Z is a normal or branched aliphatic radical containing 4–9 carbon atoms - (SNg) –CHN – OCH3 –CH –CH –CH –Cl –Cl –Cl –CH –CH –Cl –Cl –Cl –CH –CH –CH –Cl –Cl –Cl –CH –CH –CH –Cl –Cl –CH –CH – CHClOH –CHH –CH –CH –CH –CH –CH –CH –CH –CH –CH –CH –CH –CH –CH –CH –CH –CH –CH –CH –CH – C – I – C. CH2CH3 in the presence of a basic catalyst, at an elevated temperature, followed by deactivation of the catalyst after achieving the desired degree of conversion, characterized in that, to simplify the process, compounds with an aminosilyl group of forms are used as a catalyst mules p | “;; / WR R) K / n, where R is methyl, ethyl, H; R is normal () -allsh1, SKCHj), 31H (CH3) .2, cyclohexyl, octyl, carbamide radical —C — NHC / tH9 o o —Cf — NjCH,) 5 O (L is normal () -alkyl , hydrogen; R and R together can form butylene or pentylene; n 1.2, and the catalyst is used in an amount of 1-10 mol.%, the process is carried out at 80-130 ° C, and chloro-organic anhydride is used as a catalyst deactivator. 1-3 mol of deactivator per 1 mol of catalyst, the remaining monomer is removed by distillation, priority is given by signs: 03.02.81 with R SKCHj), or SiH (CHj) 2 and all Signs of values and radicals of the formula; 09.12,81 with R - normal.-Alkyl, cyclohexyl, octyl, carbamide radical (-C-NHCHj, -O-C-NHCi Hg or -C-N (CH.Jp. 66
    公开号:SU1189340A3
    申请号:SU823385205
    申请日:1982-02-02
    公开日:1985-10-30
    发明作者:Робэн Жан
    申请人:Рон-Пуленк Спесьялитэ Шимик (Фирма)；
    IPC主号:
    专利说明:

    1 The invention relates to chemistry, more specifically to an improved method for producing polyisocyanate-polyisocyanurates of varying degrees of polymerization, which are used as components of the bases of varnishes and paints. The aim of the invention is to simplify the process, which is easy to control, in contrast to the previously known ones, due to the use of catalysts containing an aminosilyl group. The invention is illustrated by the following examples. Example 1. In the flask load 537.6 g (3.2 mol) of hexamethylene diisocyanate. The temperature is brought to -100 ° C and 7.5 g (0.063 mol) N, N-dimethyl trimethylsilylamine is added to the isocyanate. After keeping the mixture at 100 ° C for 30 minutes, the content of NCO groups is reduced by 15%. The reaction is stopped by introducing into the reaction mixture 7 benzoyl chloride. Most of the remaining hexamethylene diisocyanate is distilled off at a pressure of 1.5 mm Hg. 184 g of product are obtained, which is subjected to distillation in a film stirring device. In this way, 103 g of cyclotrimer containing 0.546 NCO / 100 tons (according to the theory for hexamethylene diisocyanate trimer: 0.585) are obtained, the viscosity of which is 16 P at 25 ° C. Example 2. 134.4 g of hexamethylene diisocyanate (0, 8 mol) and 1.3 hexamethyldisilazane (0.008 mol), after which the reaction mixture is kept at 100 ° C for 7 hours. The content of NCO groups becomes 1.07 / / 100 g. The excess hexamethylene diisocyanate is distilled off and the residue is converted into film evaporator by stirring In this way, 19 g of product containing 0.55 NCO / 100 g (according to the theory for tris (isocyanathexamethylene) -isocyanurate: 0.59. The bands in the spectrum of known isothodianurates (1645 and 1690 cm and the NCO absorption band of 2270 cm –– 0. correspond to 25 P at 25 C and the spectrogram of gel permeation chromatography shows that it consists only of a trimer having mol. 504. The dimer content is less than 5%, and the content of free diisocyanate is less than 0.1%. Example 3. The reaction mixture consisting of 100 g (0.6 mol) of hexamethylene diisocyanate and 1.4 (0.013 mol) of catalyst (CHg) j is maintained for 3 hours. The reaction is stopped by adding 2 g (0.014 mol) of C HyCOCf. The degree of conversion of the isocyanate groups is 16%. After removal of excess isocyanate monomer, the compound is obtained. characterized as tris-1,3,5- (6-isocyanatohexyl) -isocyanurate, containing less than 5% dimer, in which the content of NCO-rpynn is 0.541 NCO / 100 g. Example 4 a mixture consisting of 100 g (0.6 mol) of hexamethylene diisocyanate and 2.8 g (0.014 mol) of the catalyst HH nSi (CH,),. a 17 J Stop the reaction by adding 2 g (0.014 mol) of CgHjCOCt. The degree of conversion of the isocyanate groups is 14%. After removal of excess monomeric isocyanate, a compound characterized as Tris-1,3,5- (6-isocyanatohexyl) -isocyanurate containing 0.560 NCO / 100 g is obtained. Example 5. The reaction mixture consisting of 100 g (0.6 mol) of hexamethylene diisocyanate and 2.5 g (0.016 mol) of the catalyst X TYAN-ZKSNz g. Stop the reaction by adding 2 g (0.014 mol) of C HyCOCt. The degree of conversion of the isocyanate groups is 18%. After removing the excess isocyanate monomer, a compound characterized as tris-1,3,5- (6-isocyanatohexyl) -isocyanurate containing 0.540 NCO / 100 g is obtained. Example 6. Hold the reaction mixture for 2.5 h at 10 ° C
    the amount of 100 g (0.6 mol) of methylenediislate and 1.6 g (0.008 mol) of catalyst
    (S.N5) 2 -Y-81 (SNZ) h.
    Stop the reaction by adding 0.6 g (0.02 mol) of gaseous HCt.
    The degree of conversion of the isocyanate groups is 20.5%.
    After removing the excess monomeric isocyanate, a compound characterized as tris-1, 8.5- (6-isocyanatohexyl) -isocyanurate containing 0.529 NCO / 100 g is obtained, Example 7. The reaction mixture consisting of 100 g (O, 6 mol) of hexamethylene diisocyanate and 2.1 g (0.014 mol) of catalyst
    - & 1 (dn) s
    Stop the reaction by adding 1.8 g (0.013 mol) of C HjCOCt.
    The conversion of isocyanate groups is 19.5%.
    After removing the excess isocyanate monomer, a compound characterized as tris-1,3,5- (b-isocyanatohexyl) isocyanurate containing 0.535 NCO / 100 g is obtained.
    Example 8. The reaction mixture consisting of 100 g (0.06 mol) of hexamethylene diisocyanate and 2.1 g (0.07 mol) of catalyst was agitated for 1.5 hours.
    SNS
    (C4H9) i-N-Si-N- (). CHj
    Stop the reaction by adding 2.8 g (0.02 mol) of C HjCOCt.
    The degree of conversion of the isocyanate groups is 21%.
    After removing the excess monomeric isocyanate, a compound characterized as tris1, 3.5- (6-isocyanatohexyl) -isocyanurate, containing 0.524 NCO / 100 g, is obtained.
    Example 9. The reaction mixture is maintained for 1.1 hours at 95 ° C, consisting of 100 g (0.6 mol) of hexamethylene diisocyanate and 2.4 g (0.012 mol) of catalyst
    SNS
    O-k-o
    SNS
    893404
    Stop the reaction by adding 1.6 g (0.012 mol).
    The degree of conversion of the isocyanate groups is 14%. 5 After removing the excess monomeric isocyanate, a compound characterized as tris-1, 3,5- (6-isocyanatohexyl) -isocyanurate containing 0.563 NCO / 100 g is obtained. 10 Example 10. A mixture of from 100 g (0.6 mol) of hexamethylene diisocyanate as a monomeric isocyanate and 1 g of 15 (0.007 mol) of catalyst
    SNZ SShch
    H-Si-NH-Si-H
    I I ° СНз СНз
    Stop the reaction by adding 0.9 g (0.008 mol).
    The degree of conversion of the isocyanate groups is 12%.
    After removal of excess monomeric isocyanate, a compound characterized as tris-1,355- (6-isocyanatohex1) 0-isocyanurate containing 0.569 NCO / 100 g is obtained.
    Example 11. Withstand 5 hours :. with a reaction mixture consisting of 100 g of hexamethylene diisocyanate and 3.8 g (0.016 mol) of a catalyst () 3-Si-Nn-Si- (C2 H5) h.
    Stop the reaction by adding 2.1 g (0.015 mol) .COCt.
    The degree of conversion of the isocyanate groups is 23%.
    After removal of excess monomeric isocyanate, a compound characterized as tris--1,3,5- (6-isocyanatohexyl) -is.O5 cyanurate containing 0.535 NCO / 100 g is obtained.
    Example 12. The reaction mixture consisting of 100 g (0.7 mol) of tetramethylene diisocyanate and 1 g of 0 (0.008 mol) of a catalyst of hexamethyldisilazane was agitated for 6 hours.
    Stop the reaction by adding 0.8 g (0.012 mol) of CHjCOCt.
    The degree of conversion of the isocyanate groups is 19%.
    After removing the excess monomeric isocyanate, a compound characterized as tris-1, 3.5- (4-butyl isocyanato) isocirate containing 0.597 NCO / 100 g is obtained. Example 13. Hold the reaction mixture consisting of 100 g for 7 h ( 0.6 mol) bis -1,2- (methylene isocyanato) -cyclobutane and 2.0 g (0.016 mol) of the catalyst (CHa), - Si-NH-Si- (CHa) -. The reaction is stopped by the addition of 1.5 g (0.02 mol) of SNDOC1. The degree of conversion of the isocyanate groups is 16%. After removal of the excess monomeric isocyanate, a compound characterized as a tris-1, 3,5- (2-methisisocyanatocyclobout1) -isocyanurate containing is obtained. 0.540 NCO / 100 g. Example 14. Hold the reaction mixture for 6 hours at 130 ° C consisting of 100 g (0.54 mol) of 3,5,5-trimethyl-3-isocyanatomethyl-1-isocyanatocyclohexane (INDI) and 1.4 g (0.012 mol) of catalyst (CH) 3Si-N- (CH3) 2 Stop the reaction by adding 2 g (0.014 mol) of C HjCOCt. The degree of conversion of the isocyanate groups is 14%. After removal of excess monomeric isocyanate, the compound is characterized as Tris-1,3,5- (3,5,5-trimethyl-3-isocyanatometry cyclohexyl) -isocyanurate, containing 0.410 N00 / 100 g. Example 15. Hold for 24 h at } 30 ° C, a reaction mixture consisting of 100 g (0.6 mol) of hexamethylene diisocyanate and 10 g (0.06 mol) of a catalyst of hexamethyldisilazane. Stop the reaction by adding 6 g (0.08 mol) of CHjCOCt. The degree of conversion of the isocyanate groups exceeds 90%. The compound obtained is a polyisocyanurate, insoluble and infusible, containing a very small amount of NCO-rpynn. The degree of conversion of the isocyanate groups is 95%. Example 16. A 7 h reaction was carried out with a reaction mixture consisting of 100 g (0.6 mol) of hexamethylene diisocyanate and 3 g (0.018 mol) of a catalyst of hexamethyldisilazane. Remove the reaction by adding 1 g (0.007 mol). The conversion is for isocyanate groups of 30%. After removal of the excess monomeric isocyanate, a compound characterized as a tris-1, 3,5- (6-isocyanatohexyl) -eiocyanurate containing 0.490 NCO / 100 is obtained. Example 17. A 5 h reaction was carried out with a reaction mixture consisting of 100 g (0.6 mol) of hexamethylene diisocyanate and 1 g (0.008 mol) of a catalyst (CH) h-81-HH-51- (CH). Stop the reaction by adding 0.8 g (0.012 mol) of CHjCOCt. The degree of conversion of the isocyanate groups is 5.2%. After removing the excess monomeric isocyanate, a compound characterized as tris-1,3,5- (b-isocyanatrhexyl) -isocyanurate containing 0.575 NCO / 100 g is obtained. Example 18. At 100 ° C, the reaction mixture consisting of 100 g ( 0.6 mol) of hexamethylene diisocyanate and 2 g (0.015 mol) of catalyst (CHj) -81-MH-51- (CH3) g. The reaction is carried out for 6.5 h, samples are taken from the reaction mass after 3 h, then 4 h 40 min and finally 6.5 hours. In each sample taken after removal of excess monomeric isocyanate, polyisocyanatisocyanurates are contained, the characteristics of which oryh are presented in the table. The pentamer is a polyisocyanate-polyisocyanurate containing 2 isocyanurate cycles per mole. Heptamer is a polyisocyanate-polyisocyanurate containing 11893 cycles of 3 isocyanurate cycles per mole. Example 19. 100 g (0.46 mol) of 2,2,4-trimethylhexylene-1 6-diisocyanates and 1 g of hexamethyldisyl-j zane (0.008 mol) are suspended at 6 h. The reaction is quenched by the addition of 1 g (0.013 mol) of CHjCOCt. . The degree of conversion of the isocyanate 10 groups is 18%. After removing the excess monomer, a compound characterized as a 1,3,5-tris (isocyanate-trimethyl 08 hexyl) isocyanurate containing 0.427 NCO / 100 g is obtained. Example 20. 100 g (0.5 mol) of lysine diisocyanate and 1 g (0.008 mol ) Hexamethyldisilazane is suspended for 6 hours. The reaction is stopped by adding 1 g (0.013 mol) of CHcCf. The degree of conversion of the isocyanate groups is 16%. After removal of the excess monomer, 1,3,5-tris- (4-isocyanato-2-methoxybutyl) -isocyanate, containing 0.443 N00 / 100 g, is obtained.
    权利要求:
    Claims (1)
    [1]
    METHOD FOR PRODUCING POLYISOCYANATE-POLYISOCYANOURATES by cyclic-trimerization of aliphatic diisocyanates of the general formula
    0CN-Z-NCO where Z is a normal or branched aliphatic radical containing 4-9 carbon atoms
    - (ODzSNSOOSNZ-CH2-P-CH g - sn 3 in the presence of a basic catalyst, at elevated temperature, followed by deactivation of the catalyst after reaching the desired conversion, characterized in that, in order to simplify the process, compounds with an aminosilyl group are used as a catalyst formulas where R 1 is methyl, ethyl, H;
    R 1 'is normal (C ^ -C ^) - alkyl,
    Si (CH 3 ) 5 , SiH (CH 3 ). z , cyclohexyl, octyl, carbamide radical
    -C-NHCIk - C-NHCJig
    II 0 II о о
    R n 'is normal (C., - 0 ^) - alkyl, hydrogen;
    R and R 1 ′ 1 together may form butylene or pentylene;
    η = 1.2, moreover, the catalyst is used in an amount of 1-10 mol. ^, the process is carried out ·. at 80-130 s , and as the deactivator of the catalyst using organic acid chloride or hydrogen chloride in an amount
    1-3 mol of deactivator per 1 mol of catalyst, the remaining monomer is removed by distillation.
    Priority by signs:
    02/03/81 at R = Si (CH 3 ) 3 or SiHiCHj /, and all other signs and values of radicals by the formula;
    12/9/81 at R - normal
    C ^ -C ^ -alkyl, cyclohexyl, octyl, carbamide radical (-C-NHCH 3 , z — х θ
    -C-NHC 4 H 9 or -CN (CH, A).
    0 0 'S>
    1 1189340 2
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    同族专利:
    公开号 | 公开日
    PL141806B1|1987-08-31|
    CA1183843A|1985-03-12|
    BR8200553A|1982-12-07|
    NO820287L|1982-08-04|
    DD202015A5|1983-08-24|
    EP0057653A2|1982-08-11|
    ES509255A0|1983-01-16|
    FI75813C|1988-08-08|
    EP0057653A3|1982-08-25|
    ES8302672A1|1983-01-16|
    FI820324L|1982-08-04|
    RO83836A|1984-04-12|
    KR890000379B1|1989-03-15|
    KR830009150A|1983-12-17|
    DE3263070D1|1985-05-23|
    BG42187A3|1987-10-15|
    US4412073A|1983-10-25|
    DK44882A|1982-08-04|
    NO158877B|1988-08-01|
    FI75813B|1988-04-29|
    EP0057653B1|1985-04-17|
    NO158877C|1988-11-09|
    RO83836B|1984-05-30|
    MX7482E|1989-03-27|
    YU43254B|1989-06-30|
    YU20882A|1987-02-28|
    CS248022B2|1987-01-15|
    PL234915A1|1982-09-27|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    CH422781A|1962-12-13|1966-10-31|Monsanto Co|Process for the preparation of silicon-containing heterocyclic triisocyanates|
    US3337510A|1964-05-28|1967-08-22|Gen Electric|Organosilicon compositions and methods for preparing the same|FR2522667B1|1982-03-04|1984-05-11|Rhone Poulenc Spec Chim|
    DE3339579A1|1983-11-02|1985-05-09|Bayer Ag, 5090 Leverkusen|NEW ISOCYANATO ISOCYANURATE, A METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS ISOCYANATE COMPONENT IN POLYURETHANE PAINTS|
    US4719245A|1984-03-08|1988-01-12|The Dow Chemical Company|Flexible polyisocyanurate-urethane foam|
    DE3507719A1|1985-03-05|1986-09-11|Bayer Ag, 5090 Leverkusen|POLYISOCYANATES CONTAINING ISOCYANURATE GROUPS, A METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS ISOCYANATE COMPONENTS IN POLYURETHANE PAINTS|
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    DE3541859A1|1985-11-27|1987-06-04|Bayer Ag|METHOD FOR PRODUCING POLYISOCYANATES CONTAINING ISOCYANURATE GROUPS AND THE USE THEREOF AS ISOCYANATE COMPONENTS IN POLYURETHANE PAINTS|
    US4640868A|1986-02-10|1987-02-03|Morton Thiokol Inc.|Clear, weather resistant adherent coating|
    GB2203159B|1987-04-03|1990-12-12|Asahi Chemical Ind|An isocyanurate polyisocyanate and its use as a curing agent for a two-component polyurethane composition|
    US6765111B1|1988-02-27|2004-07-20|Bayer Aktiengesellschaft|Process for the production of polyisocyanates containing isocyanurate groups and their use|
    DE3814167A1|1988-04-27|1989-11-09|Bayer Ag|METHOD FOR PRODUCING POLYISOCYANATES CONTAINING ISOCYANURATE GROUPS AND THE USE THEREOF|
    DE3827596A1|1988-08-13|1990-02-15|Bayer Ag|NEW CATALYSTS, A METHOD FOR THEIR PRODUCTION AND THE USE THEREOF FOR THE PRODUCTION OF POLYISOCYANATES CONTAINING ISOCYANURATE GROUPS|
    DE69025028T2|1989-05-16|1996-07-18|Nippon Polyurethane Kogyo Kk|METHOD FOR PRODUCING MODIFIED ORGANIC POLYISOCYANATES|
    DE4015155A1|1990-05-11|1991-11-14|Bayer Ag|METHOD FOR PRODUCING ISOCYANURATE POLYISOCYANATES, THE COMPOUNDS CONTAINED BY THIS METHOD AND THEIR USE|
    US5124427A|1991-01-22|1992-06-23|Miles Inc.|Polyisocyanates containing allophanate and isocyanurate groups, a process for their production and their use in two-component coating compositions|
    CA2072916C|1991-07-22|2003-02-11|Terry A. Potter|A process for the production of polyisocyanates containing allophanateand isocyanurate groups|
    US5235018A|1991-07-22|1993-08-10|Miles Inc.|Polyisocyanates containing allophanate and isocyanurate groups, a process for their production and their use in two-component coating compositions|
    US5298431A|1991-09-30|1994-03-29|Olin Corporation|Process for producing low viscosity isocyanate trimers|
    ES2087386T3|1991-10-02|1996-07-16|Bayer Ag|POLYISOCYANATES CONTAINING ALOPHANATE AND ISOCIANURATE GROUPS, A PROCEDURE FOR THEIR PRODUCTION AND USE IN TWO-COMPONENT COATING COMPOSITIONS.|
    US5221743A|1992-03-02|1993-06-22|Olin Corporation|Process for producing isocyanurates by cyclotrimerizing isocyanates using polymer-bound catalysts|
    US5258482A|1992-06-12|1993-11-02|Miles Inc.|Polyisocyanates containing allophanate and isocyanurate groups, a process for their production from a mixture of diisocyanates and their use in two-component coating compositions|
    US5905151A|1993-02-18|1999-05-18|Bayer Corporation|Trimer catalyst for aliphatic and aromatic isocyanates|
    US5370908A|1993-05-24|1994-12-06|Olin Corporation|Low VOC, heat-curable, one-component and two-component coating compositions based on organic polyisocyanates|
    US5290902A|1993-06-22|1994-03-01|Miles Inc.|Polyisocyanates containing allophanate and isocyanurate groups, a process for their production from cyclic diisocyanates and their use in two-component coating compositions|
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    US5691440A|1995-10-05|1997-11-25|Arco Chemical Technonogy, L.P.|Catalyst and process for producing isocyanate trimers|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    FR8102192A|FR2499085B1|1981-02-03|1981-02-03|
    FR8123135A|FR2517674B1|1981-12-09|1981-12-09|
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