US20120035391A1 - Process for the preparation of polyisocyanates and use thereof - Google Patents

Process for the preparation of polyisocyanates and use thereof Download PDF

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Publication number
US20120035391A1
US20120035391A1 US13/193,189 US201113193189A US2012035391A1 US 20120035391 A1 US20120035391 A1 US 20120035391A1 US 201113193189 A US201113193189 A US 201113193189A US 2012035391 A1 US2012035391 A1 US 2012035391A1
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US
United States
Prior art keywords
catalyst
process according
isocyanate
atom
optionally
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
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US13/193,189
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English (en)
Inventor
Frank Richter
Martin Brahm
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Covestro Deutschland AG
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Bayer MaterialScience AG
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Filing date
Publication date
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Assigned to BAYER MATERIALSCIENCE AG reassignment BAYER MATERIALSCIENCE AG ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: RICHTER, FRANK, BRAHM, MARTIN
Publication of US20120035391A1 publication Critical patent/US20120035391A1/en
Priority to US14/509,202 priority Critical patent/US9458097B2/en
Assigned to COVESTRO DEUTSCHLAND AG reassignment COVESTRO DEUTSCHLAND AG CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: BAYER MATERIALSCIENCE AG
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C263/00—Preparation of derivatives of isocyanic acid
    • C07C263/16—Preparation of derivatives of isocyanic acid by reactions not involving the formation of isocyanate groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
    • C07F9/5435—Cycloaliphatic phosphonium compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
    • C08G18/022—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only the polymeric products containing isocyanurate groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/166—Catalysts not provided for in the groups C08G18/18 - C08G18/26
    • C08G18/168—Organic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/83—Chemically modified polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds

Definitions

  • the invention relates to the use of specific phosphonium salts as catalysts for isocyanate modification (oligomerisation or polymerisation), and to a process for the preparation of correspondingly modified isocyanates.
  • modified polyisocyanates contain free NCO groups, which may optionally also have been temporarily deactivated with blocking agents, they are extraordinarily high-quality starting materials for the production of a large number of polyurethane plastics and coating compositions.
  • (hydrogen poly)fluorides optionally also in the form of their phosphonium salts, for isocyanate modification is known inter alia from EP-A 962455, EP-A 962454, EP-A 896009, EP-A 798299, EP-A 447074, EP-A 379914, EP-A 339396, EP-A 315692, EP-A 295926 and EP-A 235388.
  • the tetraorganylphosphonium (hydrogen poly)fluorides of the prior art exhibit the disadvantage that occasionally, when they are used, the reaction can be maintained only by the continuous metered addition of catalyst, that is to say the decomposition of the catalyst in the isocyanate medium takes place unacceptably quickly in technical terms as compared with the modification reaction.
  • the object underlying the invention was to develop a modification process using phosphonium salts as catalysts which is not to be encumbered with the above-mentioned disadvantages.
  • the invention provides a catalyst for isocyanate modification comprising phosphonium salts containing at least one cycloalkyl substituent bonded directly to the P atom of the phosphonium cation.
  • Preferred phosphonium salts for isocyanate modification are those whose cation corresponds to the general formula I:
  • Preferred cations of formula I are those in which R 1 to R 4 independently of one another represent identical or different organic radicals from the group C 1 - to C 20 -alkyl, cyclopentyl and cyclohexyl, wherein the alkyl radicals can be branched and the cycloalkyl radicals can be substituted,
  • Particularly preferred phosphonium salts for isocyanate modification are those of the above-mentioned type wherein the following species are used as anions X ⁇ to the phosphonium cation of the general formula (I): fluoride (F), di- and/or poly-(hydrogen)fluorides ([F ⁇ ⁇ (HF) m ], wherein m represents whole or fractional numbers from 0.001 to 20, preferably from 0.1 to 20, particularly preferably from 0.5 to 20, most particularly preferably from 0.5 to 5.
  • the catalysts can be used individually or in arbitrary mixtures with one another.
  • Another embodiment of the invention further provides a process for isocyanate modification, in which
  • the modification process according to the invention very generally yields, in a simple manner, a broad range of polyisocyanates which are of high quality and are therefore very valuable for the polyurethane sector.
  • the process according to the invention yields polyisocyanates of the so-called isocyanate trimer type (i.e. containing isocyanurate and/or iminooxadiazinedione structures) with a small proportion of uretdione groups (isocyanate dimers).
  • the proportion of the latter in the process products increases as the reaction temperature rises.
  • any known mono-, di- or poly-isocyanates of the prior art can in principle be used, individually or in arbitrary mixtures with one another.
  • hexamethylene diisocyanate (HDI), 2-methylpentane-1,5 -diisocyanate, 2,4,4-trimethyl-1,6-hexane diisocyanate, 2,2,4-trimethyl-1,6-hexane diisocyanate, 4-isocyanatomethyl-1,8-octane diisocyanate, 3(4)-isocyanatomethyl-1-methylcyclohexyl isocyanate (IMCI), isophorone diisocyanate (IPDI), 1,3- and 1,4-bis(isocyanatomethyl)benzene (XDI), 1,3- and 1,4-bis(isocyanatomethyl)cyclohexane (H6XDI), 2,4- and 2,6-toluene diisocyanate (TDI), bis(4-isocyanatophenyl)methane (4,4′MDI), 4-isocyanatophenyl-2-isocyanatophen
  • aliphatic, cycloaliphatic or araliphatic diisocyanates is particularly preferred.
  • Hexamethylene diisocyanate (HDI), 2-methylpentane-1,5-diisocyanate, 2,4,4-trimethyl-1,6-hexane diisocyanate, 2,2,4-trimethyl-1,6-hexane diisocyanate, 4-isocyanatomethyl-1,8-octane diisocyanate, 3 (4)-isocyanatomethyl-1-methylcyclohexyl isocyanate (IMCI), isophorone diisocyanate (IPDI), 1,3- and 1,4-bis(isocyanatomethyl)benzene (XDI), 1,3- and 1,4-bis(isocyanatomethyl)cyclohexane (H6XDI) are most particularly preferred.
  • IMCI isophorone diisocyanate
  • XDI 1,3- and 1,4-bis(isocyanatomethyl)benzene
  • H6XDI 1,3- and 1,4-bis(isocyanatomethyl)cycl
  • the amount of catalyst to be used in the process according to the invention is governed primarily by the isocyanate used and the desired rate of reaction and is in the range from 0.001 to 5 mol %, based on the sum of the amounts of the isocyanate used and of the catalyst. Preferably from 0.002 to 2 mol % catalyst are used.
  • the catalyst can be used in the process according to the invention undiluted or dissolved in solvents.
  • Suitable solvents are any compounds that do not react with the catalyst and are capable of dissolving it to a sufficient degree, for example aliphatic or aromatic hydrocarbons, alcohols, ketones, esters as well as ethers. Alcohols are preferably used.
  • the process according to the invention can be carried out in the temperature range from 0° C. to +250° C., preferably from 20 to 180° C., particularly preferably from 40 to 150° C., and can be terminated at any desired degree of conversion, preferably after from 5 to 80%, particularly preferably from 10 to 60%, of the monomeric diisocyanate used have been converted.
  • the unconverted monomer and any solvent used concomitantly can be separated off by means of any known separation techniques such as, for example, distillation, optionally in the specific form of thin-layer distillation, extraction or crystallisation/filtration. Combinations of two or more of these techniques can, of course, also be used.
  • polyisocyanate prepared according to the invention is still to contain free, unconverted monomer, as is of interest, for example, for further processing to NCO-blocked products, separation of the monomers following deactivation of the catalyst can be omitted.
  • the unconverted monomer is preferably separated off. After separation, the products according to the invention preferably have a residual monomer content ⁇ 0.5%, preferably ⁇ 0.1 wt. %.
  • the unconverted monomer is preferably separated off by distillation.
  • TOF A *( B*t ) ⁇ 1 [mol*(mol*sec) ⁇ 1 ].
  • the oligomerisation can be carried out in a tubular reactor or a multi-vessel cascade.
  • advantage is gained in particular from the significantly lower tendency of the catalysts according to the invention, as compared with the known catalysts of the prior art, spontaneously to form gel particles in the product even when applied in a highly concentrated solution or in the form of the pure active ingredient.
  • the products and product mixtures obtainable by the process according to the invention are starting materials which can be used in many ways for the production of foamed and unfoamed plastics as well as surface coatings, coating compositions, adhesives and additives.
  • the process products according to the invention can be used in pure form or in conjunction with other isocyanate derivatives of the prior art, such as, for example, polyisocyanates containing uretdione, biuret, allophanate, isocyanurate and/or urethane groups, the free NCO groups of which have optionally been deactivated with blocking agents.
  • isocyanate derivatives of the prior art such as, for example, polyisocyanates containing uretdione, biuret, allophanate, isocyanurate and/or urethane groups, the free NCO groups of which have optionally been deactivated with blocking agents.
  • Mol % were determined by NMR spectroscopy and are always based, unless indicated otherwise, on the sum of the NCO secondary products. Measurements were carried out using DPX 400 and DRX 700 devices from Brucker on approximately 5% ( 1 H-NMR) and approximately 50% ( 13 C-NMR) samples in dry C 6 D 6 at a frequency of 400 and 700 MHz ( 1 H-NMR) or 100 and 176 MHz ( 13 C-NMR). As reference for the ppm scale there were used small amounts of tetramethylsilane in the solvent with 0 ppm 1 H-NMR chem. shift. Alternatively, reference was made to the signal of the C 6 D 5 H contained in the solvent: 7.15 ppm 1 H-NMR chem.
  • the dynamic viscosities were determined at 23° C. using a VT 550 viscometer from Haake. By means of measurements at different shear rates it was ensured that the flow behaviour of the described polyisocyanate mixtures according to the invention as well as that of the comparison products corresponds to that of ideal Newtonian fluids. Mention of the shear rate can therefore be omitted.
  • the residual monomer contents were determined by gas chromatography.
  • the diisocyanates used are products from Bayer MaterialScience AG, D-51368 Leverkusen, all other commercially available chemicals were obtained from Aldrich, D-82018 Taufmaschinen.
  • the catalyst was deactivated by addition of an amount, equivalent to the catalyst, of p-toluenesulfonic acid (as a 40% solution in isopropanol); stirring was then carried out for a further 30 minutes at the reaction temperature, followed by working up.
  • the time between the first addition of catalyst and addition of the deactivator solution was used to calculate the TOF (turnover frequency, [mol converted NCO groups/(mol catalys* reaction time in seconds)]) indicated in Table 1.
  • Comparison Example 1 The procedure described in Comparison Example 1 was followed, except that IPDI was used instead of HDI and the conversion of NCO groups was adjusted to about 2 mol. At a reaction temperature of 60° C. (Comparison Example 7), a TOF of from 0.002 to 0.005 was obtained. If the reaction temperature is raised to 100° C. (Comparison Example 8), it is not possible to achieve a uniform reaction procedure despite the continuous addition of catalyst. After 1.26 mol of NCO groups had been converted, the TOF was 0.0005.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
US13/193,189 2010-08-03 2011-07-28 Process for the preparation of polyisocyanates and use thereof Abandoned US20120035391A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US14/509,202 US9458097B2 (en) 2010-08-03 2014-10-08 Process for the preparation of polyisocyanates and use thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102010038845A DE102010038845A1 (de) 2010-08-03 2010-08-03 Verfahren zur Herstellung von Polyisocyanaten und deren Verwendung
DE102010038845.9 2010-08-03

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US14/509,202 Division US9458097B2 (en) 2010-08-03 2014-10-08 Process for the preparation of polyisocyanates and use thereof

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US20120035391A1 true US20120035391A1 (en) 2012-02-09

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US13/193,189 Abandoned US20120035391A1 (en) 2010-08-03 2011-07-28 Process for the preparation of polyisocyanates and use thereof
US14/509,202 Active US9458097B2 (en) 2010-08-03 2014-10-08 Process for the preparation of polyisocyanates and use thereof

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Country Status (7)

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US (2) US20120035391A1 (de)
EP (1) EP2415795B1 (de)
JP (1) JP5972538B2 (de)
KR (1) KR101845560B1 (de)
CN (1) CN102442959B (de)
DE (1) DE102010038845A1 (de)
ES (1) ES2442798T3 (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4098678A1 (de) * 2021-06-02 2022-12-07 Basf Se Verfahren zur modifizierung von isocyanaten unter verwendung von difluorosilikatsalzen als katalysator

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Publication number Priority date Publication date Assignee Title
EP3107922B1 (de) 2014-02-18 2018-04-25 Covestro Deutschland AG Verfahren zur isocyanatmodifizierung unter verwendung von katalysatoren mit n-p-n-sequenz
US9850338B2 (en) 2014-02-18 2017-12-26 Covestro Deutschland Ag Process for isocyanate modification using spirocyclic ammonium salts as catalyst
KR20180041665A (ko) 2015-08-17 2018-04-24 코베스트로 도이칠란트 아게 촉매로서 시클릭 암모늄 염을 사용하는 이소시아네이트의 개질 방법
WO2018095869A1 (de) 2016-11-22 2018-05-31 Basf Se Verfahren zur herstellung von trimeren isocyanaten
WO2018153801A1 (de) 2017-02-22 2018-08-30 Covestro Deutschland Ag Verfahren zur modifizierung von mindestens pentamethylendiisocyanat unter verwendung von spirocyclischen ammoniumsalzen als katalysator
CN107868226B (zh) * 2017-12-07 2020-08-28 万华化学集团股份有限公司 一种窄分布二异氰酸酯三聚体的制备方法
EP3885385A1 (de) 2020-03-23 2021-09-29 Basf Se Verfahren zur modifizierung von isocyanaten unter verwendung von guanidiniumsalzen als katalysator
CN111548288A (zh) * 2020-05-09 2020-08-18 深圳市前海博扬研究院有限公司 一种异氰酸酯改性的uv单体及其制备方法
CN111793182B (zh) * 2020-07-15 2022-04-22 万华化学集团股份有限公司 一种多异氰酸酯组合物
EP3985044A1 (de) 2020-10-13 2022-04-20 Basf Se Verfahren zur modifizierung von isocyanaten
WO2023088793A1 (en) 2021-11-16 2023-05-25 Basf Se Preparation of polyisocyanates containing iminooxadiazinedione groups and their use

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Publication number Priority date Publication date Assignee Title
EP4098678A1 (de) * 2021-06-02 2022-12-07 Basf Se Verfahren zur modifizierung von isocyanaten unter verwendung von difluorosilikatsalzen als katalysator

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ES2442798T3 (es) 2014-02-13
US20150025268A1 (en) 2015-01-22
EP2415795B1 (de) 2013-11-13
KR101845560B1 (ko) 2018-04-04
DE102010038845A1 (de) 2012-02-09
JP5972538B2 (ja) 2016-08-17
EP2415795A1 (de) 2012-02-08
US9458097B2 (en) 2016-10-04
JP2012036186A (ja) 2012-02-23
KR20120012953A (ko) 2012-02-13
CN102442959B (zh) 2016-07-27
CN102442959A (zh) 2012-05-09

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