WO2011125310A1 - Catalyseur pour la production de résine polyuréthane et procédé pour produire la résine polyuréthane - Google Patents

Catalyseur pour la production de résine polyuréthane et procédé pour produire la résine polyuréthane Download PDF

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Publication number
WO2011125310A1
WO2011125310A1 PCT/JP2011/001892 JP2011001892W WO2011125310A1 WO 2011125310 A1 WO2011125310 A1 WO 2011125310A1 JP 2011001892 W JP2011001892 W JP 2011001892W WO 2011125310 A1 WO2011125310 A1 WO 2011125310A1
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WIPO (PCT)
Prior art keywords
acid
catalyst
polyurethane resin
pka
group
Prior art date
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PCT/JP2011/001892
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English (en)
Japanese (ja)
Inventor
榊原徳
田中宣志
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サンアプロ株式会社
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Priority to JP2012509305A priority Critical patent/JPWO2011125310A1/ja
Publication of WO2011125310A1 publication Critical patent/WO2011125310A1/fr

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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
    • C08G18/06—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
    • C08G18/48—Polyethers
    • C08G18/487—Polyethers containing cyclic groups
    • C08G18/4883—Polyethers containing cyclic groups containing cyclic groups having at least one oxygen atom in the ring
    • 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
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/20—Heterocyclic amines; Salts thereof
    • C08G18/2045—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings
    • C08G18/2063—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings having two nitrogen atoms in the condensed ring system
    • 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
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3218—Polyhydroxy compounds containing cyclic groups having at least one oxygen atom in the ring

Definitions

  • the present invention relates to a catalyst for producing a polyurethane resin and a method for producing a polyurethane resin using the catalyst. More specifically, the present invention relates to a catalyst suitable for producing a polyurethane resin such as a rigid / semi-rigid / soft foam and a production method suitable for a rigid / semi-rigid / soft foam using the catalyst.
  • Polyurethane resins formed by reacting polyols with organic polyisocyanates or isocyanate prepolymers can be used as hard and flexible foams, paints, adhesives, elastomers, sealants, etc., because they have a variety of physical properties and functions. It is used in a wide range of industrial fields, from materials to building materials, automobiles, electronics / electricity, and industrial materials.
  • a two-part curable polyurethane resin that cures by mixing a polyol with an organic polyisocyanate or an isocyanate prepolymer it can be filled into a mold after two-part mixing or applied to a substrate to cause a curing reaction. The method is generally practiced.
  • amine catalysts and metal catalysts are usually used.
  • the curing reaction is accelerated, but the pot life of the two-component liquid mixture is shortened. Problems such as insufficient filling in the mold and curing start before application of the base material are likely to occur.
  • metal catalysts tend to be used from the viewpoint of safety because of their strong toxicity, and the need for alternative catalysts is increasing year by year.
  • a method using a cycloamidine (salt) that can bring about rapid curing after a certain time as a catalyst is employed (see, for example, Patent Document 1 and Patent Document 2).
  • chlorofluorocarbon foaming agents have been mainly used for rigid foam applications such as panels and boards.
  • ozone layer destruction due to the problem of ozone layer destruction, switching from chlorofluorocarbon foaming agents to water is proceeding.
  • water is used as a foaming agent, the viscosity-reducing effect of the fluorocarbon foaming agent is lost, so the filling property in the mold is lowered, and even if cycloamidine (salt) is used, insufficient filling occurs. There is a problem that it becomes easy.
  • the object of the present invention is to increase the viscosity of a mixed solution by suppressing the initial reactivity after two-component mixing of a polyol and an organic polyisocyanate, even in the case of rigid foams such as panels and boards using water as a foaming agent. It is an object of the present invention to provide a catalyst for producing a polyurethane resin, which can moderately maintain the filling property in a mold and can cause rapid curing after a certain time.
  • ⁇ M represents an integer of 2 to 6, and the hydrogen atom of the methylene group may be substituted with an organic group.
  • a feature of the method for producing a polyurethane resin of the present invention is that it includes a step of obtaining a polyurethane resin by reacting the above-mentioned catalyst for producing a polyurethane resin, a polyol and an organic polyisocyanate or an isocyanate prepolymer.
  • the polyurethane resin production catalyst of the present invention even in the case of rigid foams such as panels and boards using water as a foaming agent, the initial reaction after two-component mixing of polyol and organic polyisocyanate or isocyanate prepolymer, etc. By suppressing the property, the thickening is moderated and the filling property in the mold can be kept good, and then it can be cured quickly.
  • the initial reaction after mixing the two liquids is suppressed as compared with the case of using only cycloamidine.
  • the pot life can be maintained for a long time.
  • the acid forming the salt with cycloamidine (C) becomes stronger, the initial reactivity can be suppressed, but rapid curing cannot be brought about after a certain period of time, resulting in deterioration of productivity and produced polyurethane.
  • the physical properties of the resin are reduced.
  • the polyurethane resin production catalyst is used, even in the case of rigid foams such as panels and boards using water as a foaming agent, by suppressing the initial reactivity immediately after mixing the two liquids The thickening is moderated and the filling property in the mold is improved. Then, it can be quickly cured.
  • m represents an integer of 2 to 6, and preferably an integer of 3 to 5.
  • the organic group that may be substituted for the hydrogen atom of the methylene group include an alkyl group having 1 to 6 carbon atoms (such as methyl, ethyl, isopropyl, n-butyl, t-butyl, and n-hexyl), and 1 to 6 carbon atoms.
  • Hydroxyalkyl groups such as hydroxymethyl, 2-hydroxyethyl, 2-hydroxypropyl, 2-hydroxyisopropyl, 3-hydroxy-t-butyl and 6-hydroxyhexyl
  • dialkylamino groups having 2 to 12 carbon atoms (dimethylamino) Methylethylamino, diethylamino, diisopropylamino, t-butylmethylamino, di-n-hexylamino and the like.
  • Examples of the cycloamidine represented by the general formula (1) include 1,5-diazabicyclo [4,3,0] -nonene-5 (DBN), 1,5-diazabicyclo [4,4,0] -decene-5. 1,8-diazabicyclo [5,4,0] -undecene-7 (DBU; “DBU” is a registered trademark of Sun Apro Corporation), 5-hydroxypropyl-1,8-diazabicyclo [5,4, 0] -undecene-7 and 5-dibutylamino-1,8-diazabicyclo [5,4,0] -undecene-7. Of these, DBN and DBU are preferred.
  • Organic acids include aromatic hydroxy compounds ⁇ phenol, alkyl-substituted phenols (o-cresol, m-cresol, p-cresol, 2-ethylphenol, 3-ethylphenol, 4-ethylphenol, xylenols, trimethylphenols Tetramethylphenols, pentamethylphenols, etc.), alkoxy-substituted phenols (2-methoxyphenol, 3-methoxyphenol, 4-methoxyphenol, 2-ethoxyphenol, 3-ethoxyphenol, 4-ethoxyphenol, etc.), Halogen-substituted phenols (fluorophenol, chlorophenol, bromophenol, iodophenol, etc.), naphthols, aminophenols, polyphenols (catechol, resorcinol, hydroquinone, biff) Nord, bisphenols, pyrogallol
  • inorganic acid examples include boric acid and perhydrohalic acid (perbromic acid, periodic acid, etc.).
  • R 1 to R 5 each independently represents a hydrogen atom, a linear or branched alkyl group having 1 to 5 carbon atoms, or an alkoxy group
  • the linear or branched alkyl group having 1 to 5 carbon atoms include a methyl group, an ethyl group, an isopropyl group, an n-butyl group, a t-butyl group, and an n-pentyl group.
  • Examples of the linear or branched alkoxy group having 1 to 5 carbon atoms include methoxy group, ethoxy group, isopropoxy group and n-butoxy group.
  • phenol o-cresol, 2,4,6-trimethylphenol, 2-methoxyphenol and 2-ethoxyphenol are particularly preferable.
  • carboxylic acid ⁇ saturated aliphatic carboxylic acid (acetic acid, propionic acid, butyric acid, valeric acid, isovaleric acid, methylethylacetic acid, trimethylacetic acid, caproic acid, isocaproic acid, Diethylacetic acid, 2,2-dimethylbutyric acid, enanthic acid, caprylic acid, pelargonic acid, 2-ethylhexanoic acid, n-undecylenic acid, lauric acid, n-tridecylenic acid, myristic acid, n-pentadecylenic acid, palmitic acid, margarine Acid, stearic acid, n-nonadecylene acid, arachidic acid, n-heneicoic acid, etc.), unsaturated aliphatic carboxylic acids (acrylic acid, crotonic acid, isocrotonic acid, vinylacetic acid, methylethylacetic acid, trimethylacetic
  • the content of (A1) is 0.2 to 0.8 mol, preferably 0.4 to 0.6 mol, and the content of (A2) is 1 mol of (C).
  • a salt of DBU, phenol and 2-ethylhexanoic acid ⁇ mixing ratio (C: A1: A2) is a molar ratio of 1: 0.5: 0.5 ⁇ , DBU, phenol and 2-ethyl Hexanoic acid salt ⁇ mixing ratio (C: A1: A2) is molar ratio 1: 0.4: 0.4 ⁇ , DBU, o-cresol and oleic acid salt ⁇ mixing ratio (C: A1: A2) is The molar ratio is 1: 0.6: 0.4 ⁇ , the salt of DBU, 2,4,6-trimethylphenol and 2-ethylhexanoic acid ⁇ mixing ratio (C: A1: A2) is 1: 0.
  • C: A1: A2 is 1: 0.5: 0.5 ⁇ in molar ratio
  • DBU and 2- Methoxyphenol and 2-ethylhexanoic acid salt ⁇ mixing ratio is molar ratio 1: 0.5: 0.7 ⁇
  • salt of DBN, phenol and 2-ethylhexanoic acid ⁇ mixing ratio is 1: 0.5: 0.5 ⁇ in molar ratio
  • DBN and 2 A preferred example is a salt of methoxyphenol and 2-ethylhexanoic acid ⁇ mixing ratio (C: A1: A2) is 1: 0.5: 0.5 ⁇ in molar ratio.
  • the catalyst of the present invention may contain a known solvent.
  • the solvent include water and alcohol (such as ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, and butanediol).
  • the content can be determined as appropriate, and is, for example, 5 to 1900% by weight based on the weight of the salt (E).
  • the catalyst of the present invention may contain other catalysts (such as an organometallic catalyst and an amine catalyst) without departing from the spirit of the present invention.
  • organometallic catalyst include known organometallic catalysts, such as potassium carboxylates (such as potassium 2-ethylhexanoate and potassium acetate), organotin catalysts (stannous diacetate, stannous dioctoate, stannous dilaurate, stana Sudiolate, dibutyltin oxide, dibutyltin diacetate, dibutyltin dilaurate and dioctyltin dilaurate), organic bismuth catalysts (such as bismuth octylate and bismuth naphthenate), and organic cobalt catalysts (such as cobalt naphthenate) .
  • amine catalyst examples include known amine catalysts and the like, and amines (triethylenediamine, 2-methyltriethylenediamine, N-methylmorpholine, N-ethylmorpholine, dimorpholinodiethylaminoether, dimethylethanolamine, N, N, N ′ , N′-tetramethylethylenediamine, N, N, N ′, N′-tetramethylpropylenediamine, N, N, N ′, N′-tetramethylhexamethylenediamine, dimethylcyclohexylamine, 1,3,5-tris (N, N-dimethylaminopropyl) hexahydro-S-triazine, 2,4,6-tris (dimethylaminomethyl) phenol, N, N, N ′, N ′′, N ′′ -pentamethyldiethylenetriamine, N, N, N ′, N ′′, N ′′ -pentamethyldipropylenetriamine, bis
  • the amount (% by weight) of the other catalyst used is preferably 5 to 1900% by weight, more preferably 20 to 900% by weight, based on the weight of the salt (E).
  • the mixing ratio is as described above.
  • the solvent and its use amount are as described above.
  • the catalyst of the present invention is suitable for the production of polyurethane resins such as rigid, semi-rigid and flexible foams.
  • the method for producing a polyurethane resin of the present invention includes a step of reacting the polyurethane resin production catalyst of the present invention with a polyol and an organic polyisocyanate or an isocyanate prepolymer to obtain a polyurethane resin.
  • the amount of use (wt%) of the catalyst of the present invention ⁇ in the case of use in combination with other catalyst (wt) ⁇ is preferably 0.001 to 20 wt%, more preferably based on the weight of the polyol. Is an amount of 0.01 to 10% by weight, particularly preferably 0.1 to 5% by weight.
  • the polyol is not particularly limited, and known polyols can be used, and examples include polyoxyalkylene ether polyols, polyester polyols, amine polyols, polymer polyols, polybutadiene polyols, castor oil-based polyols, acrylic polyols, and mixtures thereof.
  • isocyanate a known isocyanate or the like can be used.
  • Examples of the isocyanate prepolymer include those obtained by reacting the aforementioned polyol and organic polyisocyanate.
  • the isocyanate index is not particularly limited, but is preferably 50 to 800, more preferably 70 to 400. Within this range, the resin strength is good, and the possibility that unreacted isocyanato groups remain is also reduced.
  • the polyurethane foam is obtained by reacting the polyurethane resin production catalyst with a polyol and an organic polyisocyanate or an isocyanate prepolymer in the presence of a foaming agent. Obtaining a body.
  • a foaming agent water and a volatile foaming agent can be used.
  • a known volatile foaming agent or the like can be used, such as chlorofluorocarbon (hydrogen atom-containing halogenated hydrocarbon) ⁇ for example, 1,1,1,3,3-pentafluoropropane (HFC-245fa), 1,1,1,3,3-pentafluorobutane (HFC-365mfc), 1,1,1,2-tetrafluoroethane (HFC-134a), 1,1,1,2,3,3,3- Heptafluoropropane (HFC-227ea) ⁇ , hydrofluoroether ⁇ eg, HFE-254pc ⁇ , halogenated hydrocarbon ⁇ eg, methylene chloride ⁇ , low boiling point hydrocarbon ⁇ eg, propane, butane, pentane, cyclopentane ⁇ , carbonic acid Examples thereof include gases and mixtures thereof.
  • the catalyst of the present invention exhibits an effect that cannot be obtained with other catalysts, particularly water, among these blowing agents.
  • the amount of the foaming agent used is appropriately determined according to the density of the polyurethane foam to be produced and the physical properties of the foam.
  • the density (kg / m 3 ) of the obtained polyurethane foam is determined to be 5 to 200 (preferably 10 to 100).
  • Example 2 The catalyst DBU of the present invention, a salt of phenol and 2-ethylhexanoic acid (2) were obtained in the same manner as in Example 1 except that the ratio of phenol to be reacted with DBU and 2-ethylhexanoic acid was changed.
  • the catalyst DBU of the present invention, o-cresol and oleic acid salt (3) were obtained in the same manner as in Example 1 except that
  • Example 6 The catalyst DBU of the present invention and the salt of 2-methoxyphenol and 2-ethylhexanoic acid (6) except that the ratio of 2-methoxyphenol and 2-ethylhexanoic acid to be reacted with DBU was changed as in Example 5. Got.
  • the catalyst DBU of the present invention, 2-ethoxyphenol and oleic acid salt (7) were obtained.
  • polyurethane foams were prepared in the following manner according to the formulations shown in Table 1, and the filling properties and curability were evaluated. The results are shown in Table 2 (DBU salt) and Table 3 (DBN salt).
  • Polyol Polyol foam stabilizer having a hydroxyl value of 338 obtained by addition reaction of propylene oxide to sucrose: SH 193 (polyether siloxane polymer, Toray Dow Corning Co., Ltd.) Flame retardant: TMCPP (Tris ( ⁇ -chloropropyl) phosphate, Daihachi Chemical Industry Co., Ltd.) Evaluation sample (catalyst): DBU or DBN was added in an amount of 0.3 part.
  • Other catalysts U-CAT 420A (Amine-based catalyst, San Apro Corporation)
  • Isocyanate Millionate MR-200 (crude MDI, NCO index 110, Nippon Polyurethane Industry Co., Ltd.)
  • the catalyst of the present invention is hardened while maintaining good filling properties in the mold even when water is used as a foaming agent, compared to the conventional cycloamidine (salt). I was able to promote it.
  • the polyurethane resin production catalyst of the present invention is suitably used for production of polyurethane resins such as rigid, semi-rigid and flexible foams.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

La présente invention concerne un catalyseur pour la production de résine polyuréthane, qui est capable de maintenir une bonne aptitude au remplissage dans un moule ou une bonne applicabilité sur une base en maintenant une durée de vie utile suffisamment longue (vie en pot) d'une résine, tout en permettant un durcissement rapide de la résine après un certain temps. La présente invention concerne spécifiquement un catalyseur pour la production d'une résine polyuréthane, qui est caractérisé en ce qu'il est un sel (E) qui utilise une cycloamidine (C) représentée par la formule générale (1) en combinaison avec un ou plusieurs acides choisis dans le groupe constitué d'acides (A1) ayant un pKa1 de 8 à 11 et un ou plusieurs acides choisis dans le groupe constitué d'acides (A2) ayant un pKa1 de 4 à 6. Le catalyseur pour la production d'une résine polyuréthane est également caractérisé en ce que la teneur des acides (A1) est de 0,2 à 0,8 mole pour 1 mole de la cycloamidine (C), la teneur des acides (A2) est de 0,2 à 0,8 mole pour 1 mole de la cycloamidine (C), et la teneur des acides (A1 + A2) est de 0,8 à 1,2 mole pour 1 mole de la cycloamidine (C). (Dans la formule générale (1), m représente un entier de 2 à 6, et un atome d'hydrogène dans le groupe méthylène peut être substitué par un groupe organique.)
PCT/JP2011/001892 2010-04-05 2011-03-30 Catalyseur pour la production de résine polyuréthane et procédé pour produire la résine polyuréthane WO2011125310A1 (fr)

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JP2012509305A JPWO2011125310A1 (ja) 2010-04-05 2011-03-30 ポリウレタン樹脂製造用触媒及びポリウレタン樹脂の製造方法

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JP2010-086864 2010-04-05

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012072249A (ja) * 2010-09-28 2012-04-12 San Apro Kk ポリウレタン樹脂製造用触媒及びポリウレタン樹脂の製造方法
JP2013234272A (ja) * 2012-05-09 2013-11-21 Tosoh Corp ポリウレタン樹脂製造用触媒組成物及びそれを用いたポリウレタン樹脂の製造方法
JP2018522095A (ja) * 2015-06-18 2018-08-09 ダウ グローバル テクノロジーズ エルエルシー 赤外放射で硬化可能な潜在性２液型ポリウレタン接着剤

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3769244A (en) * 1966-10-29 1973-10-30 San Abbott Ltd Polyurethane foam reaction catalyzed by salts of 1,8 - diaza-bicyclo(5,4,0)undecene-7
JPH02235916A (ja) * 1989-03-08 1990-09-18 Hitachi Chem Co Ltd 耐熱性樹脂の製造法および耐熱性樹脂組成物
JP2002187927A (ja) * 2000-10-13 2002-07-05 Tosoh Corp 二成分系ポリウレタンシーラント製造用の触媒
JP2005120222A (ja) * 2003-10-16 2005-05-12 Tosoh Corp ポリウレタン樹脂製造用触媒組成物及びポリウレタン樹脂の製造法
WO2010109789A1 (fr) * 2009-03-24 2010-09-30 サンアプロ株式会社 Catalyseur pour fabrication de résine de polyuréthane et procédé de fabrication d'une résine de polyuréthane

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3769244A (en) * 1966-10-29 1973-10-30 San Abbott Ltd Polyurethane foam reaction catalyzed by salts of 1,8 - diaza-bicyclo(5,4,0)undecene-7
JPH02235916A (ja) * 1989-03-08 1990-09-18 Hitachi Chem Co Ltd 耐熱性樹脂の製造法および耐熱性樹脂組成物
JP2002187927A (ja) * 2000-10-13 2002-07-05 Tosoh Corp 二成分系ポリウレタンシーラント製造用の触媒
JP2005120222A (ja) * 2003-10-16 2005-05-12 Tosoh Corp ポリウレタン樹脂製造用触媒組成物及びポリウレタン樹脂の製造法
WO2010109789A1 (fr) * 2009-03-24 2010-09-30 サンアプロ株式会社 Catalyseur pour fabrication de résine de polyuréthane et procédé de fabrication d'une résine de polyuréthane

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012072249A (ja) * 2010-09-28 2012-04-12 San Apro Kk ポリウレタン樹脂製造用触媒及びポリウレタン樹脂の製造方法
JP2013234272A (ja) * 2012-05-09 2013-11-21 Tosoh Corp ポリウレタン樹脂製造用触媒組成物及びそれを用いたポリウレタン樹脂の製造方法
JP2018522095A (ja) * 2015-06-18 2018-08-09 ダウ グローバル テクノロジーズ エルエルシー 赤外放射で硬化可能な潜在性２液型ポリウレタン接着剤

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