WO2010021335A1 - Procédé de fabrication d'un mélange d'isocyanate - Google Patents

Procédé de fabrication d'un mélange d'isocyanate Download PDF

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Publication number
WO2010021335A1
WO2010021335A1 PCT/JP2009/064493 JP2009064493W WO2010021335A1 WO 2010021335 A1 WO2010021335 A1 WO 2010021335A1 JP 2009064493 W JP2009064493 W JP 2009064493W WO 2010021335 A1 WO2010021335 A1 WO 2010021335A1
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Prior art keywords
isocyanate mixture
inert solvent
adsorbent
reaction
mixture
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PCT/JP2009/064493
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English (en)
Japanese (ja)
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保武 若林
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日本ポリウレタン工業株式会社
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Publication of WO2010021335A1 publication Critical patent/WO2010021335A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C263/00—Preparation of derivatives of isocyanic acid
    • C07C263/10—Preparation of derivatives of isocyanic acid by reaction of amines with carbonyl halides, e.g. with phosgene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C263/00—Preparation of derivatives of isocyanic acid
    • C07C263/18—Separation; Purification; Stabilisation; Use of additives

Definitions

  • the present invention relates to a method for producing an isocyanate mixture. More specifically, the present invention relates to an efficient method for producing an isocyanate mixture having a low metal content.
  • the process for producing an isocyanate mixture includes a condensation process for synthesizing an amine mixture by condensing aniline and formaldehyde in the presence of an acid catalyst, or a process for obtaining an amine mixture by a hydrogenation reaction of a nitro compound or a nitrile compound.
  • the industrial production process of the isocyanate mixture is generally performed using metal equipment mainly composed of iron or stainless steel in terms of cost and maintenance. In regular repairs of this manufacturing facility, etc., equipment and piping are opened and inspected, so that the metals that make up them come into contact with oxygen in the air and are oxidized to form metal oxides, for example, iron. It remains in the manufacturing process as iron. The metal oxide remaining in the production process is insoluble in the isocyanate mixture.
  • the reaction process liquid containing an isocyanate mixture will be in an acidic state by an acidic compound as mentioned above.
  • the reflux equipment is corroded and / or eroded by the acid, and metal components such as iron are mixed in the solvent.
  • the metal content in the reaction step liquid is further increased.
  • the concentration step part of the recovered solvent is returned to the concentration step again in order to prevent the yield from being lowered due to the isocyanate mixture accompanying the solvent separated from the reaction step solution.
  • the storage stability of the isocyanate mixture may be affected.
  • the isocyanate mixture is used as a starting material of polyurethane, the reactivity of the isocyanate mixture with a polyol compound or the like is affected by the amount of iron contained in the isocyanate mixture.
  • by-products such as water produced by the reaction between the acidic compound and the metal oxide are mixed in the isocyanate mixture, it may cause modification and alteration. For the above reasons, it is desirable that the iron content in the isocyanate mixture is as low as possible.
  • the iron content in the isocyanate mixture is 10 ppm or less, it is said that the storage stability of the isocyanate mixture and the reactivity when used as a raw material for producing polyurethane are not adversely affected.
  • the iron content contained in the isocyanate mixture obtained by the above production process is usually 10 ppm or less, which greatly affects the storage stability of the isocyanate mixture and the reactivity when used as a polyurethane production raw material. is not.
  • the iron content may reach several hundred ppm, its storage stability and reactivity with polyol compounds, etc. May be adversely affected.
  • Patent Document 1 discloses a method of treating diphenylmethane diisocyanate or diphenylmethane polyisocyanate with a microporous adsorbent having an internal surface area of at least 100 m 2 / g.
  • Patent Document 2 discloses a technique for treating an organic polyisocyanate composition with a basic adsorbent.
  • Patent Document 1 can reduce the iron content in the isocyanate mixture to a level that does not cause a problem in practice, it introduces a new problem that the microporous adsorbent is mixed in the isocyanate mixture. Further, in the method of Patent Document 2, since a basic adsorbent is used, there is a concern about modification and alteration of the organic polyisocyanate composition after treatment, and there is a problem in storage stability.
  • Patent Document 3 discloses a method for removing mercury contained in hydrocarbon oils such as naphtha and condensate oil, which are mixed base materials for petroleum products, using activated carbon.
  • Patent Documents 4 and 5 disclose a method in which water or a chlorine-containing compound is added to a hydrocarbon oil containing heavy metal to remove the heavy metal by the porous adsorbent.
  • Patent Document 6 discloses a method of adsorbing and removing heavy metal by adding a chelating agent to hydrocarbon oil containing heavy metal and bringing it into contact with activated carbon.
  • these methods are not efficient because it is necessary to modify heavy metals using additives such as chlorine-containing compounds, chelating agents, and water.
  • the present invention has been made in view of the above circumstances, and has an object to provide a method for producing an isocyanate mixture in which the amount of mixed metals including iron is reduced, which affects the reactivity of the isocyanate mixture. To do.
  • the present inventor has recovered an inert organic solvent refluxed in the reaction step or a concentration step in a general isocyanate mixture production step, and again enters the concentration step.
  • the present inventors have found that the metal content in the isocyanate mixture as the final product can be efficiently reduced by treating the returned inert organic solvent with an adsorbent, thereby completing the present invention.
  • the present invention 1.
  • a concentration step of concentrating a reaction step liquid comprising an acidic compound such as hydrogen and / or excess phosgene in a concentration tank to distill off the inert solvent and the acidic compound from the reaction step solution In the method for producing an isocyanate mixture, the reaction is performed under a condition where the inert solvent is refluxed, and in the concentration step, at least a part of the distilled inert solvent is again returned to the concentration tank. And at least one of the refluxing inert solvent and the inert solvent returned back into the concentration tank is Method for producing isocyanate mixtures, characterized in that it is treated with an adsorbent prior to being introduced into les in the tank, 2.
  • a process for producing one isocyanate mixture wherein both the refluxing inert solvent and the inert solvent returned back into the concentration tank are treated with an adsorbent before being introduced into the respective tank; 3.
  • the method for producing an isocyanate mixture at least one of the inert solvent refluxed in the reaction step and the inert solvent returned to the concentration step is treated with the adsorbent before returning to the reaction vessel or the concentration vessel.
  • the amount of metal mixed into the reaction tank or the concentration tank from other equipment is reduced, and as a result, the amount of metal mixed into the isocyanate mixture can be greatly reduced.
  • work processes such as adjustment (reduction) of iron content required when using as a polyurethane raw material, become unnecessary.
  • the isocyanate mixture itself is not a method of treating with an adsorbent, the adsorbent is not mixed into the final product isocyanate mixture.
  • the method for producing an isocyanate mixture according to the present invention includes an amine mixture, phosgene and an inert solvent introduced into a reaction vessel, and a reaction step of reacting the amine mixture and phosgene to synthesize an isocyanate mixture, and the isocyanate mixture, inert
  • the reaction is performed under a condition where the inert solvent is refluxed, and in the concentration step, at least a part of the distilled inert solvent is returned again into the concentration tank.
  • at least one of the refluxing inert solvent and the inert solvent returned back into the concentration tank is It is intended to be processed by the adsorbent prior to being introduced into the
  • the solvent containing the metal refluxed in the reaction step, and the isocyanate mixture separated in the concentration step At least one of the solvent containing the metal recovered and returned to the concentration step is treated with an adsorbent.
  • the treatment with the adsorbent hereinafter referred to as adsorption treatment
  • count of the adsorption process in a reaction process and a concentration process is arbitrary, Each may be 1 time or multiple times.
  • the method for the adsorption treatment is not particularly limited, and may be a method in which an adsorbent is added to each solvent, or a method in which each solvent is passed through a packed column or column packed with the adsorbent.
  • a method of passing a solvent through a packed tower or column when performing the adsorption treatment a plurality of times, both the serial processing in which the packed tower and column are arranged in series, and the parallel processing in which they are arranged in parallel, A combination of these may be used.
  • the adsorbent used in the present invention is not particularly limited as long as it is a microporous adsorbent capable of adsorbing metals such as iron, chromium, nickel and molybdenum contained in the solvent during the production process, particularly iron.
  • a microporous adsorbent include activated carbon, carbon fiber, activated clay, zeolite, silica gel and the like. Among these, activated carbon, activated clay, and zeolite are preferable in view of metal adsorption ability and cost, and activated carbon is particularly optimal.
  • the average particle size of the adsorbent is not particularly limited, but is preferably 0.01 to 20 mm, more preferably 0.05 to 20 mm, and still more preferably 0.1 to 20 mm.
  • the average particle diameter can be measured by a known method. For example, activated carbon can be measured according to JIS K 1474. Further, a sieving method, a light scattering method, or the like can be used.
  • the average particle diameter in the present invention is a value measured by a sieving method for activated carbon for JIS K 1474 and other adsorbents.
  • the water contained in the adsorbent may be mixed with the solvent in contact with the adsorbent and introduced into the reaction process or the concentration process together with the solvent.
  • the water content in the adsorbent is preferably 5% by mass or less, more preferably 3% by mass or less.
  • the moisture contained in the adsorbent may be removed by a known technique in advance before use, or may be removed simultaneously with the removal of moisture in the process of producing the isocyanate mixture after filling in a packed tower or the like.
  • the water content can be measured by a known method. For example, it can be measured using a loss on drying method or an infrared moisture meter which is an official standard measurement method.
  • the water content in the present invention is a value measured by the loss on drying method.
  • the amount of adsorbent used varies depending on the particle size of the adsorbent and the amount of metal in the solvent, but cannot be defined unconditionally. However, it is possible to treat 100 to 10,000 kg of inert solvent, preferably 100 to 5000 kg per kg of adsorbent. preferable.
  • the treatment temperature is 20 to 200 ° C., preferably 50 to 200 ° C.
  • the treatment pressure is 0.01 to 5 MPa, preferably 0.03 to 3 MPa.
  • the treatment time is 1 to 200 minutes, preferably 1 to 120 minutes.
  • the method for producing an isocyanate mixture according to the present invention is characterized in that the solvent refluxed in the reaction step and / or the solvent reused in the concentration step is adsorbed, so that the other steps are conventionally known.
  • the isocyanate mixture include aliphatic diisocyanate mixtures such as hexamethylene diisocyanate (HDI); alicyclic diisocyanate mixtures such as isophorone diisocyanate; aromatic diisocyanate mixtures such as toluene diisocyanate (TDI) and diphenylmethane diisocyanate (MDI), and the like.
  • a suitable amine mixture is used.
  • an MDI mixture in which the influence of iron is particularly problematic specifically, 20 to 70% by mass of an isocyanate having two benzene rings and two isocyanate groups in one molecule, and a benzene ring and an isocyanate group in one molecule. It is effective to use the method of the present invention for an MDI mixture containing 80 to 30% by mass of an isocyanate-based multinuclear condensate having 3 or more of each.
  • the inert solvent is arbitrary as long as it is generally used for the production of isocyanate mixtures, and benzene, toluene, xylene, chlorobenzene, dichlorobenzene, methyl ethyl ketone, methyl isobutyl ketone, ethyl acetate, butyl acetate, cyclohexane, etc. are used. be able to.
  • After the concentration step it can be purified by a conventional method such as distillation to obtain a pure isocyanate mixture (purification step).
  • a conventional method such as distillation to obtain a pure isocyanate mixture (purification step).
  • purification step purification step.
  • adopt conventionally well-known conditions suitably for other manufacturing conditions, for example, conditions, such as phosgenation reaction conditions, concentration conditions, and distillation conditions, according to the isocyanate mixture to manufacture.
  • FIG. 1 shows a production apparatus 1 used in the method for producing an isocyanate mixture of the present invention.
  • the amine mixture A and phosgene B are introduced into the reaction vessel 10 together with chlorobenzene, which is an inert solvent, and a phosgenation reaction is performed under heating and reflux conditions (reaction step).
  • the chlorobenzene is sent to the first heat exchanger 11 together with the hydrogen chloride produced as a by-product from the reaction of the amine mixture A and phosgene B, and the excess acidic compound such as phosgene B, and then the first solvent recovery tank. 12 is recovered.
  • the recovered chlorobenzene and acidic compound are introduced from the lower part of the first adsorbent packed tower 13 packed with 500 kg of activated carbon 13A having an average particle diameter of 2 mm, and are adsorbed by the activated carbon 13A (liquid passing speed 60 kg / Min, processing temperature 80 ° C.).
  • metal components such as iron eluted in the chlorobenzene from the heat exchanger 11 and the recovery tank 12 are removed by corrosion and erosion by acidic compounds.
  • the chlorobenzene after the adsorption treatment is discharged from the upper part of the first adsorbent packed tower 13 and returned to the reaction vessel 10 again.
  • the produced reaction mixture containing the isocyanate mixture, acidic compound and chlorobenzene is sent to the concentration tank 20 and concentrated (concentration process).
  • the chlorobenzene and acidic compound distilled off in this step are sent to the second heat exchanger 21 and then recovered in the second solvent recovery tank 22.
  • the recovered chlorobenzene and acidic compound are introduced from the lower part of the second adsorbent packed tower 23 packed with 500 kg of activated carbon 23A having an average particle diameter of 2 mm, and are adsorbed by the activated carbon 23A in the same manner as in the reaction step. (Flow rate 60 kg / min, treatment temperature 80 ° C.).
  • the adsorption process is performed only once in the reaction step and the concentration step, but the present invention is not limited to this. That is, a plurality of adsorbent packed towers can be provided and subjected to adsorption treatment a plurality of times. In this case, the plurality of packed towers may be arranged in series or in parallel. Further, the liquid passing speed and the treatment temperature during the adsorption treatment are not limited to the above values, and can be set as appropriate. Furthermore, although the reaction process and the concentration process were performed in separate tanks, they can be performed in the same tank, that is, the concentration process can be performed in the reaction tank. In addition, the configuration of the manufacturing equipment, the manufacturing conditions, and the like can be appropriately changed as long as the object of the present invention can be achieved.
  • Example 1 Polymethylene polyphenyl polyamine and phosgene B, which are the amine mixture A, were introduced into the reaction vessel 10 together with chlorobenzene, and a phosgenation reaction was performed according to a conventional method. Subsequently, the reaction process liquid after phosgenation was introduced into the concentration tank 20, and excess phosgene, by-produced hydrogen chloride and chlorobenzene were separated from the isocyanate mixture to obtain an isocyanate mixture. Subsequently, this concentrated liquid was introduced into the distillation column 30, and an MDI mixture C was obtained by separating a distillate and a residue by distillation.
  • the first adsorbent packed tower 13 and the second adsorbent packed tower 23 are filled with 500 kg of activated carbon (activated carbon KW manufactured by Kuraray Chemical Co., Ltd., average particle diameter 2 mm, water content 3.0 mass%), respectively, and chlorobenzene (Iron content 50 ppm) was adsorbed through the first adsorbent packed tower 13 and the second adsorbent packed tower 23 at 80 ° C. and 60 kg / min.
  • activated carbon activated carbon KW manufactured by Kuraray Chemical Co., Ltd., average particle diameter 2 mm, water content 3.0 mass
  • chlorobenzene Iron content 50 ppm
  • Example 2 An isocyanate mixture was produced in the same manner as in Example 1 except that activated carbon (spherical activated carbon manufactured by Kureha Co., Ltd., average particle diameter 1 mm, water content 2.9% by mass) was used. As a result, the production amount of the MDI mixture containing 10 ppm or more of iron in 6 days was 30% of the total production amount, and the average iron content in all MDI mixtures produced in 6 days was 12 ppm.
  • activated carbon spherical activated carbon manufactured by Kureha Co., Ltd., average particle diameter 1 mm, water content 2.9% by mass
  • Example 3 An isocyanate mixture was produced in the same manner as in Example 1 except that activated carbon (Kuraray Chemical 4GS, Kuraray Chemical Co., Ltd., average particle size 4 mm, water content 3.0 mass%) was used. As a result, the production amount of the MDI mixture containing 10 ppm or more of iron in 6 days was 40% of the total production amount, and the average iron content in all MDI mixtures produced in 6 days was 15 ppm.
  • activated carbon Karl Chemical 4GS, Kuraray Chemical Co., Ltd., average particle size 4 mm, water content 3.0 mass%
  • Example 4 An isocyanate mixture was produced in the same manner as in Example 1 except that activated carbon (Tsurumi Coal 4GV manufactured by Turumi Coal Co., Ltd., average particle diameter 4 mm, water content 3.0 mass%) was used. As a result, the production amount of the MDI mixture containing 10 ppm or more of iron in 6 days was 40% of the total production amount, and the average iron content in all MDI mixtures produced in 6 days was 15 ppm.
  • activated carbon Troumi Coal 4GV manufactured by Turumi Coal Co., Ltd., average particle diameter 4 mm, water content 3.0 mass%
  • Example 5 An isocyanate mixture was produced in the same manner as in Example 1 except that activated carbon (Kuraray Chemical 7GS, Kuraray Chemical Co., Ltd., average particle diameter 7 mm, water content 2.4 mass%) was used. As a result, the production amount of the MDI mixture containing 10 ppm or more of iron in 6 days was 50% of the total production amount, and the average iron content in all MDI mixtures produced in 6 days was 20 ppm.
  • activated carbon Karl Chemical 7GS, Kuraray Chemical Co., Ltd., average particle diameter 7 mm, water content 2.4 mass%
  • Example 6 The same treatment as in Example 1 was performed except that the chlorobenzene containing 50 ppm of iron was not treated in the first adsorbent packed tower 13 and returned to the reaction vessel 10 as it was. As a result, the production amount of the isocyanate mixture containing 10 ppm or more of iron in 6 days was 50% of the production amount of the total isocyanate mixture, and the average content of iron in the total isocyanate mixture produced in 6 days was 18 ppm. It was.
  • Example 7 The same treatment as in Example 1 was performed except that the chlorobenzene containing 50 ppm of iron was not treated in the second adsorbent packed tower 23 and returned to the concentration tank 20 as it was. As a result, the production amount of the isocyanate mixture containing 10 ppm or more of iron in 6 days was 60% of the production amount of the total isocyanate mixture, and the average content of iron in the total isocyanate mixture produced in 6 days was 25 ppm. It was.
  • Example 8 Example except that activated clay (made by Mizusawa Chemical Co., Ltd., galeonite, particle size 2 mm, water content 3.0 mass%) was packed in the first adsorbent packed tower 13 and the second adsorbent packed tower 23 instead of the activated carbon. 1 was performed. As a result, the production amount of the isocyanate mixture containing 10 ppm or more of iron in 6 days was 50% of the production amount of the total isocyanate mixture, and the average content of iron in the total isocyanate mixture produced in 6 days was 18 ppm. It was.
  • activated clay made by Mizusawa Chemical Co., Ltd., galeonite, particle size 2 mm, water content 3.0 mass
  • Example 9 Except for charging the first adsorbent packed tower 13 and the second adsorbent packed tower 23 with zeolite (manufactured by Tosoh Corporation, HSZ-930-HOA, particle size 2 mm, water content 2.9 mass%) instead of activated carbon. The same processing as in Example 1 was performed. As a result, the production amount of the isocyanate mixture containing 10 ppm or more of iron in 6 days was 40% of the production amount of the total isocyanate mixture, and the average content of iron in the total isocyanate mixture produced in 6 days was 15 ppm. It was.
  • zeolite manufactured by Tosoh Corporation, HSZ-930-HOA, particle size 2 mm, water content 2.9 mass

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention porte sur un procédé de fabrication d'un mélange d'isocyanate (C). Le procédé comprend une étape de réaction consistant à introduire un mélange d'amine (A), du phosgène (B) et un solvant inerte dans un réservoir de réaction (10) et la réaction du mélange d'amine (A) avec du phosgène (B) pour synthétiser un mélange d'isocyanate, et une étape de concentration consistant à concentrer un liquide, qui est obtenu dans l'étape de réaction et comprend le mélange d'isocyanate, le solvant inerte et les composés acides tels que le chlorure d'hydrogène obtenu comme sous-produit et le phosgène en excès, dans un réservoir de concentration (20) pour éliminer le solvant inerte et les composés acides par évaporation à partir du liquide obtenu dans l'étape de réaction. Dans l'étape de réaction, la réaction est effectuée sous reflux du solvant inerte. Dans l'étape de concentration, au moins une partie du solvant inerte retiré par l'évaporation est à nouveau renvoyée dans le réservoir de concentration (20). Au moins l'un du solvant inerte devant être porté au reflux et du solvant inerte devant être à nouveau renvoyé au réservoir de concentration (20) est traité par un adsorbant (13A) ou un adsorbant (23A) avant l'introduction des solvants inertes dans les réservoirs respectifs (10, 20). Le procédé peut produire un mélange d'isocyanate ayant une teneur réduite d'un métal qui affecte la réactivité du mélange d'isocyanate.
PCT/JP2009/064493 2008-08-20 2009-08-19 Procédé de fabrication d'un mélange d'isocyanate WO2010021335A1 (fr)

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JP2008212109A JP2010047503A (ja) 2008-08-20 2008-08-20 イソシアネート混合物の製造方法
JP2008-212109 2008-08-20

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9266824B2 (en) 2014-01-13 2016-02-23 Warsaw Orthopedic, Inc. Methods and compositions for making an amino acid triisocyanate
CN109641175A (zh) * 2016-09-01 2019-04-16 科思创德国股份有限公司 制备异氰酸酯的方法

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017007341A (ja) * 2016-08-09 2017-01-12 株式会社リコー 画像形成方法及び画像形成装置
JP2018177273A (ja) * 2017-04-07 2018-11-15 三井化学株式会社 ペンタメチレンジイソシアネート入り容器、および、ペンタメチレンジイソシアネートの保存方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50126644A (fr) * 1974-03-22 1975-10-04
JPH0899946A (ja) * 1994-09-19 1996-04-16 Bayer Ag ジフェニルメタンジイソシアネートまたはジフェニルメタン系ポリイソシアネート混合物中の鉄含有量の減少方法
JPH11343275A (ja) * 1998-05-29 1999-12-14 Nippon Polyurethane Ind Co Ltd 多官能芳香族ポリイソシアネート組成体の製造方法
JP2002003462A (ja) * 2000-06-20 2002-01-09 Kyowa Yuka Co Ltd リジンエステルトリイソシアネートの製造法
WO2004022527A1 (fr) * 2002-09-09 2004-03-18 Kyowa Hakko Chemical Co., Ltd Ester triisocyanate de lysine et son procede de production
JP2006160684A (ja) * 2004-12-09 2006-06-22 Nippon Polyurethane Ind Co Ltd 有機ポリイソシアネート組成物、該有機ポリイソシアネートの製造方法、接着剤組成物及び塗料用組成物

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50126644A (fr) * 1974-03-22 1975-10-04
JPH0899946A (ja) * 1994-09-19 1996-04-16 Bayer Ag ジフェニルメタンジイソシアネートまたはジフェニルメタン系ポリイソシアネート混合物中の鉄含有量の減少方法
JPH11343275A (ja) * 1998-05-29 1999-12-14 Nippon Polyurethane Ind Co Ltd 多官能芳香族ポリイソシアネート組成体の製造方法
JP2002003462A (ja) * 2000-06-20 2002-01-09 Kyowa Yuka Co Ltd リジンエステルトリイソシアネートの製造法
WO2004022527A1 (fr) * 2002-09-09 2004-03-18 Kyowa Hakko Chemical Co., Ltd Ester triisocyanate de lysine et son procede de production
JP2006160684A (ja) * 2004-12-09 2006-06-22 Nippon Polyurethane Ind Co Ltd 有機ポリイソシアネート組成物、該有機ポリイソシアネートの製造方法、接着剤組成物及び塗料用組成物

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9266824B2 (en) 2014-01-13 2016-02-23 Warsaw Orthopedic, Inc. Methods and compositions for making an amino acid triisocyanate
US9573889B2 (en) 2014-01-13 2017-02-21 Warsaw Orthopedic, Inc. Methods and compositions for making an amino acid triisocyanate
CN109641175A (zh) * 2016-09-01 2019-04-16 科思创德国股份有限公司 制备异氰酸酯的方法
CN109641175B (zh) * 2016-09-01 2021-07-30 科思创德国股份有限公司 制备异氰酸酯的方法

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