US20130274506A1 - Biobased carbodiimides, a process for preparation thereof and use thereof - Google Patents

Biobased carbodiimides, a process for preparation thereof and use thereof Download PDF

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Publication number
US20130274506A1
US20130274506A1 US13/698,755 US201113698755A US2013274506A1 US 20130274506 A1 US20130274506 A1 US 20130274506A1 US 201113698755 A US201113698755 A US 201113698755A US 2013274506 A1 US2013274506 A1 US 2013274506A1
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US
United States
Prior art keywords
biobased
carbodiimide
carbodiimides
hydroxy carboxylic
carbodiimides according
Prior art date
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Abandoned
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US13/698,755
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English (en)
Inventor
Wilhelm Laufer
Armin Eckert
Franco Orsini
Robert Eiben
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.)
Rhein Chemie Rheinau GmbH
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Rhein Chemie Rheinau GmbH
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Assigned to RHEIN CHEMIE RHEINAU GMBH reassignment RHEIN CHEMIE RHEINAU GMBH ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: LAUFER, WILHELM, ECKERT, ARMIN, EIBEN, ROBERT, ORSINI, FRANCO
Publication of US20130274506A1 publication Critical patent/US20130274506A1/en
Abandoned legal-status Critical Current

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    • 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C267/00—Carbodiimides
    • 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/36—Hydroxylated esters of higher fatty acids
    • 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4288—Polycondensates having carboxylic or carbonic ester groups in the main chain modified by higher fatty oils or their acids or by resin acids
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine groups
    • 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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds

Definitions

  • the present invention relates to novel biobased carbodiimides, a process for production thereof and use thereof.
  • the biobased carbodiimides according to the invention comprise the reaction product of at least one carbodiimide and at least one carbon acid compound isolated or produced from renewable raw materials and having a functionality >1 and/or a hydroxy carboxylic ester having 2-24 carbon atoms.
  • Organic carbodiimides are known and are used, for example, as a stabilizer against the hydrolytic degradation of compounds containing ester groups. They are used mainly, for example, in the field of polyaddition and polycondensation products, particularly polyurethanes and thermoplastic polyesters.
  • Polymers are increasingly required to be based on natural raw materials, for example biobased polyols (natural oil polyols, biopolyols).
  • biobased polyols natural oil polyols, biopolyols
  • the U.S. Government launched a new programme in 2002 whereby such products may be declared “green” if they include more than 7% of a biobased raw material in the herein contemplated use sector of polyurethanes for house insulation.
  • biopolyols cannot simply replace petropolyols since they can have disadvantages relating to viscosity, defined functionality (OH groups per molecule), ageing behaviour, odour and other factors.
  • the problem addressed by the present invention was therefore that of providing novel carbodiimides which are classifiable as “a green product” and have equivalent properties to prior art carbodiimides.
  • the present invention accordingly provides biobased carbodiimides obtainable from the reaction of at least one carbodiimide and at least one carbon acid compound isolated or produced from renewable raw materials and having a functionality >1 and more than 4 carbon atoms and/or a hydroxy carboxylic ester.
  • Suitable carbodiimides for the purposes of the present invention are, in particular, monomeric or polymeric carbodiimides.
  • Carbodiimides for the purposes of the invention are preferably compounds of the general formula
  • R represents an aromatic, aliphatic, cycloaliphatic or araliphatic radical which in the case of an aromatic or araliphatic radical may bear aliphatic and/or cycloaliphatic substituents having at least two carbon atoms, preferably branched or cyclic aliphatic radicals having at least 3 carbon atoms, more particularly isopropyl groups, in at least one position ortho, preferably in both positions ortho, to the aromatic carbon atom bearing the carbodiimide group,
  • R′ C 1 -C 18 -alkyl, C 5 -C 18 -cycloalkyl, aryl, C 7 -C 18 -aralkyl or R—NCO, R—NHCONHR 1 , R—NHCONR 1 R 2 or R—NHCOOR 3 , and
  • R′′ denotes —NCO, where, in R′, R 1 and R 2 are each independently the same or different and signify a C 1— C 6 -alkyl, C 6 -C 10 -cycloalkyl or C 7 -C 18 -aralkyl radical and R 3 has one of the meanings of R 1 or denotes a polyester or polyamide radical, for example acetate or butyl and/or benzoic ester, and m is an integer from 1 to 5000 and preferably from 1 to 500.
  • Aromatic R is preferably aryl.
  • Araliphatic R is preferably C 7 -C 18 -aralkyl, to which the “N ⁇ C ⁇ N” group can be attached not only via the alkyl radical but also via the aryl radical, aliphatic R is preferably linear or branched, optionally substituted C 1 -C 18 -alkyl, and cycloaliphatic R is preferably optionally substituted C 5 -C 19 cyclo or bicycloalkyl.
  • carbodiimides have the general formula (II) where the ortho positions relative to the carbodiimide group are substituted by isopropyl and the para position relative to the carbodiimide group is likewise substituted by isopropyl, for example
  • x 1 to 50, preferably 2-20.
  • the carbodiimide comprises a compound of formula (III)
  • the aforementioned carbodiimides comprise commercially available compounds which are commercially available for example from Rhein Chemie Rheinau GmbH under the trade names Stabaxol® P100 (N—C—N content: 13-14%), Stabaxol® P400, (N—C—N content: 13-14%) and Stabaxol® P 220 (N—C—N content: 13-14%).
  • Stabaxol® P100 N—C—N content: 13-14%)
  • Stabaxol® P400 N—C—N content: 13-14%)
  • Stabaxol® P 220 N—C—N content: 13-14%).
  • the products available from Raschig as Stabilisator 9000 and 11000 can also be used for the purposes of the present invention.
  • any isocyanate is useful for producing the carbodiimides and/or polycarbodiimides used, although the carbodiimides and/or polycarbodiimides preferably used in the context of the present invention are based on aromatic isocyonates substituted by C 1 - to C 4 -alkyl, for example 2,6-diisopropylphenyl isocyanate, 2,4,6-triisopropylphenyl 1,3-diisocyanate, 2,4,6-triethylphenyl 1,3-diisocyanate, 2,4,6-trimethylphenyl 1,3-diisocyanate, 2,4′-diisocyanatodiphenylmethane, 3,3′,5,5′-tetraisopropyl-4,4′-diisocyanatodiphenylmethane, 3,3′,5,5′-tetraethyl-4,4′-diisocyanatodiphenylmethane,
  • Polycarbodiimides when obtained from isocyanates, may additionally contain still reactive NCO groups and complex-bound monomeric isocyanates.
  • a mixture of various carbodiimides may be used.
  • the carbodiimides used may be selected from the group of monomeric and/or polymeric carbodiimides, in which case the above observations concerning the compounds of the general formulae (I) to (III) are referenced.
  • Hydroxy carboxylic esters for the purposes of the present invention preferably comprise hydroxyl carboxylic esters of 2-24 carbon atoms, such as oligolactic acid for example, and/or polyhydroxybutyrates of formula (IV)
  • n 2-20.
  • the carbon acid compounds isolated from renewable raw materials and having a functionality >1 preferably comprise natural polyols (biopolyols), for example castor oil, tall oil, starch and/or sugar.
  • biopolyols for example castor oil, tall oil, starch and/or sugar.
  • Biopolyols typically have the characteristic triglyceride structure of a plant oil. Unlike petrochemically produced polyols (petropolyols) they do not have long ethylene oxide (E0) or propylene oxide (PO) chains. Biopolymers are also not as homogeneous as petropolyols, they usually also still contain double bonds, for example castor oil (shown in idealized form hereinbelow).
  • the carbon acid compounds produced from renewable raw materials and having a functionality > 1 are preferably polyols from plant oils, for example rapeseed oil or soy oil, hereinbelow shown in idealized form:
  • unsaturated fatty acids for example oleic acid.
  • the aforementioned compound is commercially available, for example from Cargill and/or Urethane Soy Systems.
  • Conversion from plant oils or from unsaturated fatty acids can take place according to methods familiar to a person skilled in the art, for example ozonization with subsequent glycolysis, epoxidation with subsequent ring opening by, for example, alcohols or hydroformylation and subsequent reduction with hydrogen.
  • the carbon acid compounds isolated or produced from renewable raw materials and having a functionality >1 and/or the hydroxy carboxylic esters are used in admixture with common non-biobased polyols based on polyether, polyester and/or polyetherester, obtainable from Bayer AG, BASF AG, etc.
  • the proportion of biobased raw materials should preferably not be below 7%, based on the biobased carbodiimide.
  • the biobased carbodiimides according to the invention are preferably obtainable via the reaction of at least one carbodiimide with at least one carbon acid compound isolated or produced from renewable raw materials and having a functionality >1 and/or the hydroxy carboxylic ester at temperatures between 20 and 200° C. and preferably 80-90° C., in solution and/or in the absence of a solvent in the presence or absence of at least one catalyst.
  • the present invention also provides a process for producing the carbodiimides of the invention, wherein at least one carbodiimide is reacted with at least one carbon acid compound isolated or produced from renewable raw materials and having a functionality >1 and/or the hydroxy carboxylic ester and optionally non-biobased polyols based on polyether, polyester and/or polyetherester at temperatures between 20 and 200° C., preferably 80-90° C., in solution and/or in the absence of a solvent in the presence or absence of a catalyst.
  • the reaction in solution is preferably carried out using toluene, xylene, ethyl acetate, butyl acetate and/or methyl ethyl ketone as solvent, with temperatures of 80-120° C. being preferred for the reaction, depending on the solvent.
  • tertiary amines Preference is given to tertiary amines, matrix-soluble tin compounds, such as dibutyltin dilaurate for example, titanium compounds, such as alkali metal titanates for example, and/or alternatively lead, bismuth and/or zinc compounds.
  • matrix-soluble tin compounds such as dibutyltin dilaurate for example
  • titanium compounds such as alkali metal titanates for example, and/or alternatively lead, bismuth and/or zinc compounds.
  • the modified (biobased) carbodiimides thus obtained satisfy the criterion of a “green” product.
  • the ratio of the carbodiimide to the carbon acid compound or the hydroxy carboxylic ester is preferably in the range from 5:95 to 95:5, more preferably in the range from 7:93 to 60:40 and even more preferably in the range from 7:93 to 50:50.
  • the reaction of the carbon acid compound or the hydroxy carboxylic ester with the carbodiimide is preferably carried out at temperatures of 20° C. to 200° C., more preferably 25° C. to 150° C. and even more preferably 80° C. to 120° C., while the mixing time can be 0.1 min to 360 min, preferably 1 min to 180 min and more preferably 5 min to 120 min.
  • the carbodiimides according to the invention are very useful as an acceptor for free carboxylic acids and therefore are preferably used as stabilizers against the hydrolytic degradation of compounds containing ester groups, for example polymers containing ester groups, e.g. polycondensation products, such as for example thermoplastic polyesters, such as polyethylene terephthalate, polybutylene terephthalate, polyetheresters, polyamides, polyesteramides, polycaprolactones and also unsaturated polyester resins and polyesteresters, e.g. block copolymers of polyethylene terephthalate or polybutylene terephthalate and polycaprolactone, and polyaddition products, e.g. polyurethanes, polyureas and polyurethane-polyurea elastomers containing ester groups.
  • polymers containing ester groups e.g. polycondensation products
  • thermoplastic polyesters such as polyethylene terephthalate, polybutylene terephthalate, poly
  • the (poly)carbodiimides according to the invention are particularly Useful as stabilizers against the hydrolytic degradation of polyurethanes, preferably compact or cellular polyurethane elastomers and more particularly thermoplastic polyurethanes and also cellular or compact elastomers.
  • the present invention accordingly also provides for the use of the carbodiimides according to the invention in polyurethane applications, for rigid foam/coatings, flexible foam, CASE (Coatings, Adhesives, Sealants, Elastomers), thermoplastics, for hydrolysis control, in lubricant applications, such as ester-based oils for example, in transformer oils and for crosslinking of polyurethanes.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US13/698,755 2010-05-21 2011-05-19 Biobased carbodiimides, a process for preparation thereof and use thereof Abandoned US20130274506A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP10163621.5 2010-05-21
EP10163621A EP2388284A1 (de) 2010-05-21 2010-05-21 Biobasierte Carbodiimide, ein Verfahren zu deren Herstellung und deren Verwendung
PCT/EP2011/058219 WO2011144717A1 (de) 2010-05-21 2011-05-19 Biobasierte carbodiimide, ein verfahren zu deren herstellung und deren verwendung

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PCT/EP2011/058219 A-371-Of-International WO2011144717A1 (de) 2010-05-21 2011-05-19 Biobasierte carbodiimide, ein verfahren zu deren herstellung und deren verwendung

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EP (2) EP2388284A1 (ja)
JP (1) JP5604587B2 (ja)
KR (1) KR101451496B1 (ja)
CN (1) CN102947363B (ja)
AR (1) AR084112A1 (ja)
ES (1) ES2658180T3 (ja)
PT (1) PT2571915T (ja)
TR (1) TR201802217T4 (ja)
TW (1) TWI537239B (ja)
WO (1) WO2011144717A1 (ja)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017023175A1 (en) 2015-08-04 2017-02-09 Furanix Technologies B.V. Poly( alkylene furandicarboxylate)-comprising polyester

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DE202011109841U1 (de) 2010-06-02 2012-05-08 Rhein-Chemie Rheinau Gmbh Neuartige flexible Verpackungen
WO2016132889A1 (ja) * 2015-02-20 2016-08-25 株式会社日本触媒 硬化性樹脂組成物及びそれを用いてなる封止材
CN105294976A (zh) * 2015-11-20 2016-02-03 嘉兴洛克化学工业有限公司 一种耐水洗聚氨酯粘接剂及其制备方法
CN108715628B (zh) * 2018-06-22 2022-04-01 上海朗亿功能材料有限公司 一种脂环族聚碳化二亚胺抗水解剂及其制备方法

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Publication number Priority date Publication date Assignee Title
WO2017023175A1 (en) 2015-08-04 2017-02-09 Furanix Technologies B.V. Poly( alkylene furandicarboxylate)-comprising polyester

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CN102947363B (zh) 2015-02-11
AR084112A1 (es) 2013-04-24
CN102947363A (zh) 2013-02-27
ES2658180T3 (es) 2018-03-08
JP5604587B2 (ja) 2014-10-08
WO2011144717A1 (de) 2011-11-24
US9452975B2 (en) 2016-09-27
EP2571915A1 (de) 2013-03-27
US20140323754A1 (en) 2014-10-30
KR101451496B1 (ko) 2014-10-15
KR20130040918A (ko) 2013-04-24
JP2013526643A (ja) 2013-06-24
PT2571915T (pt) 2018-02-07
TWI537239B (zh) 2016-06-11
TW201209022A (en) 2012-03-01
EP2388284A1 (de) 2011-11-23
TR201802217T4 (tr) 2018-03-21
EP2571915B1 (de) 2017-11-22

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