WO1989000565A1 - Cyclocarbonate compounds - Google Patents

Cyclocarbonate compounds Download PDF

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Publication number
WO1989000565A1
WO1989000565A1 PCT/DE1988/000451 DE8800451W WO8900565A1 WO 1989000565 A1 WO1989000565 A1 WO 1989000565A1 DE 8800451 W DE8800451 W DE 8800451W WO 8900565 A1 WO8900565 A1 WO 8900565A1
Authority
WO
WIPO (PCT)
Prior art keywords
cyclocarbonate
radicals
mixture
halohydrin
dioxolan
Prior art date
Application number
PCT/DE1988/000451
Other languages
German (de)
English (en)
French (fr)
Inventor
Gerwald Grahe
Artur Lachowicz
Original Assignee
Dainippon Ink & Chemicals, Inc.
Dic Berlin Gmbh & Co.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Dainippon Ink & Chemicals, Inc., Dic Berlin Gmbh & Co. filed Critical Dainippon Ink & Chemicals, Inc.
Publication of WO1989000565A1 publication Critical patent/WO1989000565A1/de

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D317/34—Oxygen atoms
    • C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D317/34—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D317/34—Oxygen atoms
    • C07D317/40—Vinylene carbonate; Substituted vinylene carbonates

Definitions

  • the invention relates to cyclocarbonate compounds, processes for their preparation by reacting alkali metal hydrogen carbonates with vicinal halohydrins and their use for the preparation of the corresponding urethanes.
  • Cyclocarbonate compounds play an important role in many areas of the chemical industry both as solvents and as versatile intermediates. Numerous methods for the production of cyclocarbonates have been described ("Houben-Weyl” Methods of Organic Chemistry, Volume E 4, Georg Thieme Verlag, 1983). Probably the oldest method is based on the action of phosgene on glycols. A related process involves the reaction of glycols with chloroformic acid esters. The simplest laboratory process for the production of cyclocarbonate compounds is the transesterification of simple open-chain carbonic acid esters (advantageously diethyl carbonate) with glycols.
  • Ethylene carbonate could be obtained in low yields by reacting ethylene chlorohydrin with sodium methyl carbonate (US Pat. No. 2,784,201).
  • Simple alkylene carbonates are formed in the reaction of halohydrins with alkali metal carbonates in the presence of halogenated hydrocarbons as a diluent (US Pat. No. 2,766,258). Similar to the earlier method (DE-PS 516 281), this procedure can only be used for the production of ethylene and less advantageously propylene carbonate.
  • Vicinal halohydrins react under pressure with carbon dioxide to form cyclic carbonates (US Pat. No. 3,923,842). Vicinale can be used under mild conditions
  • Suitable cyclocarbonate compounds containing 2 to 4 carbon atoms in the chain are Suitable cyclocarbonate compounds containing 2 to 4 carbon atoms in the chain.
  • R 4 represents either a hydrogen atom or a methyl group. These compounds therefore contain no functional groups other than the cyclocarbonate function.
  • the intrinsic reactivity of the functional groups which may be present is often so high that the cyclization of the substituted halohydrins with alkali metal carbonates to cyclocarbonates may only take place under very gentle conditions, since otherwise troublesome side reactions come to the fore, e.g. B. alkaline hydrolysis, saponification, polymerization, etc.
  • the object of the invention is to develop a process for the preparation of functionally substituted cyclocarbonate compounds from functional groups having halohydrins and alkali metal carbonates, in which the disadvantages of the known processes do not occur and which can also be used for the preparation of polymeric cyclocarbonate compounds.
  • the present invention relates to a process for the preparation of cyclocarbonate compounds of the general formula
  • the substances used as starting compounds in the process according to the invention have one more than one occurring vicinal halohydrin structure, such as that in the reaction of epihalohydrin with corresponding polyfunctional compounds according to Eq. (6) emerging products is the case,
  • polyfunctional cyclocarbonates can also be prepared by the process according to the invention described here, which is illustrated by reaction equation (7):
  • R 1 is additionally a bi- or polyfunctional, optionally substituted radical.
  • Alkali metal bicarbonates serve as cyclization partners for the halohydrins in the process according to the invention, it being possible advantageously to use both sodium and potassium carbonate.
  • the process according to the invention is carried out in the presence of a solvent.
  • a solvent such as dimethylformamide, hexamethylphosphoric triamide, dimethyl sulfone, N-methylformamide, N-methyl-2-pyrrolidinone, N, N-diethylformamide, trimethylurea, trimethylphosphate, 1,3-dimethylimidazolidion-2-one, acetonitrile are suitable.
  • the invention thus also includes processes for the preparation of polymeric cyclocarbonate compounds per
  • Macromolecule contain at least one cyclocarbonate group
  • R 2 , R 3 and R k 4 each represent a hydrogen atom or an optionally substituted aliphatic, cycloaliphatic, aromatic or arylaliphatic hydrocarbon radical having 1 to 12 carbon atoms or the radicals R 2 and R 3 or R 4 are components of a 5- or 6- membered carbocyclic ring, wherein R 2 , R 3 and
  • polymeric hydrocarbons such as polyethylene, polystyrenes
  • polymeric hydrogen halides such as Teflone, polyvinylchloride
  • the polyacrylates the polymethacrylates, the polyesters, the polyimides, the polyamides, the phenoplasts, the aminoplastics, the polyurethanes, the polysilicones and the polymers of epoxides.
  • the polymeric compounds mentioned can have been prepared either by homo- or by copolymerization.
  • a particularly interesting field is the use of the cyclocarbonates obtained by the process according to the invention for the production of urethanes.
  • the corresponding reaction with primary or secondary amines proceeds according to equation (8).
  • polyurethanes can be obtained which are usually prepared from the highly toxic isocyanates.
  • dicyclocarbonates and diamines linear polyurethanes are then obtained according to equation (9).
  • Such substances can be converted into polymers with unchanged cyclocarbonate functions by polymerization, which is shown using the example of the cyclocarbonate glyceryl ester of methacrylic acid in equation (10).
  • Such linear polymers are soluble in organic solvents. By reacting with diamines or polyamines, they can change into a network structure. This process is illustrated by formula scheme (11).
  • polyurethane structures can be produced according to formula (10) and (11) without the use of isocyanates.
  • formula (10) and (11) without the use of isocyanates.
  • the polymers with cyclocarbonate functions result in mixtures which can be cured to give clear or pigmented, glossy, hard and solvent-resistant films which have all the advantages of a conventional polyurethane coating.
  • the 4-vinyl-1,3-dioxolan-2-one changes as a colorless liquid at 70 - 72 ° C (1 mbar).
  • the 1,2-cyclohexylene carbonate boils at 151 - 153 ° C (0.001 mbar) and solidifies very easily to the light brown mass.
  • the 4-methoxymethyl-1,3-dioxolan-2-one distills at 92 - 94 ° C (1 mbar) as a low-viscosity ) colorless liquid.
  • the 4-allyloxymethyl-1,3-dioxolan-2-one boils at 105 107 ° C (Imbar) as an easily movable, colorless liquid.
  • the 4-phenoxymethyl-1,3-dioxolan-2-one boils at 157-160 ° C (0.001 mbar).
  • the ethylene glycol bis (1,3-dioxolan-2-one-4-ylmethyl) ether boils at 190-195 ° C (0.001 mbar) with partial decomposition.
  • Methyl sulfoxide and 172 sodium hydrogen carbonate are reacted and worked up analogously to the information in Example 1.
  • the 4-acetyloxymethyl-1,3-dioxolan-2-one boils at 118-120 ° C (0.1 mbar) as a colorless liquid.
  • the 4-crotonoyloxymethyl-1,3-dioxolan-2-one boils at 118 - 120 ° C (0.001 mbar) as a colorless liquid.
  • the 4- (N, N-diethylamino) methyl-1,3-dioxolan-2-one distills as a light yellow liquid at 112 - 115 ° C (0.001 mbar).
  • the 4-acetyloxymethyI-1,3-dioxolan-2-one distills at 114-115 ° C (0.1 mbar) as a colorless liquid.
  • the 4-methyl-4-methoxymethyl-1,3-dioxolan-2-one distills at 102-104 ° C (1 mbar) as a colorless liquid.
  • a solution of 70 g of 3-chloro-2-hydroxypropyl methacrylate, 70 g of butyl acrylate, 17.5 g of methyl methacrylate, 17.5 g of styrene and 5 g of azo-bis-isobutyronitrile is added dropwise to 155 g of dimethylformamide over the course of two hours, which is heated to 130 ° C. The heating or cooling of the reaction vessel is adjusted so that the polymerization is carried out at 130-135 ° C.
  • the colorless, clear polymer solution is then cooled to about 80-90 ° C., 130 g of dimethylformamide, 60 g of sodium hydrogen carbonate and 1 g of trioctylmethylammonium chloride are added and the mixture is kept at 85-90 ° C. with stirring for 6 hours. The mixture is then cooled to room temperature, undissolved constituents are filtered off and the clear solution is freed of dimethylformamide in vacuo.
  • the remaining acrylic resin, still liquid at 80 ° C, is diluted with 75 g of xylene and filtered again after cooling.
  • the resulting cyclocarbonate-containing solution is weak in monetary terms, has a solids content of approx. 70% and contains practically no chlorine and no hydroxyl groups (OH number: 2-3 mg kOH / g).
  • paint solutions are formed, that produce hard, shiny, clear, lightfast and solvent-resistant polyurethane coatings both at room temperature and under baking conditions.
  • An acrylic polymer is prepared from 70 g of 3-chloro-2-hydroxypropyl methacrylate, 70 g of butyl acrylate, 40 g of styrene and 5 g of tert-butyl perbenzoate analogously to the information in Example 19 and then converted into a chlorine- and hydroxyl-free, cyclocarbonate-containing polymer.
  • a mixture of 65 g of 1,3-dichloro-2-propanol, 100 g of a solvent, 70 g of sodium hydrogen carbonate and optionally 0.5 g of a catalyst is heated to 50-120 ° C. with stirring for two to six hours.
  • the reaction mixture is then filtered, in Vacuum removed the solvent and the crude reaction product was distilled in a short column in vacuo.
  • the 4-chloromethyl-1,3-dioxolan-2-one is colorless and clear at 102-105 ° C (1 mbar).
  • Table 1 contains detailed information on Examples 21 to 29.
  • a mixture of 90 g of 3-chloro-2-hydroxypropyl isobutyrate, 200 g of dimethyl sulfoxide, 35 g of cyclohexane, 67 g of sodium hydrogen carbonate and 1 g of trioctylmethylammonium chloride is heated to boiling under reflux and the water formed is removed continuously via a water separator.
  • the 4-isobutylroxymethyl-1,3-dioxolan-2-one is isolated as a colorless liquid distilling at 138-140 ° C (0.01 mbar).
  • the distillation residue is taken up in 200 g of toluene. The mixture is then filtered and the filtrate washed twice with 20 ml of water. The organic phase is concentrated in a water jet pump vacuum and the remaining crude product is distilled in vacuo over a short column.
  • the 4-pivaloyloxymethyl-1,3-dioxolan-2-one is colorless and clear at 108-110 ° C / 0.001 mbar.
  • the 4-phenoxymethyl-1,3-dioxolan-2-one is obtained in the form of colorless crystals; Mp: 98.5-100 ° C.
  • the mixture is then filtered hot, the solvent is distilled off in vacuo at a bath temperature of 110-120 ° C. and the remaining, slightly solidifying crude product is recrystallized from boiling xylene.
  • the 4-phenoxymethyl-1,3-dioxolan-2-one is obtained in the form of yellowish crystals; Mp: 97-99 ° C.
  • DENACOL EX-211 neopentyl glycol diglycidyl ether, commercial product from Nagase Kasei Co., Japan
  • DENACOL EX-211 neopentyl glycol diglycidyl ether, commercial product from Nagase Kasei Co., Japan
  • N- (2-oxo-1,3-dioxolan-4-ylmethyl) diethanolamine remains as a yellowish, highly viscous liquid.
  • the mixture is filtered and the solvent is distilled off from the filtrate at 1 mbar and 120 ° C. bath temperature.
  • the viscous residue is mixed with 1200 g of methyl ethyl ketone and heated to boiling until the polymer goes into solution. It is filtered hot from the undissolved portions and left to cool.
  • the cyclocarbonate-containing polyurethane precipitates as a white, granular substance. The precipitate formed is filtered off and dried in a vacuum drying cabinet at 80 ° C. for 12 hours.
  • Cymel 303 (melamine resin, trade name of the company "Dyno-Cyanamid"
  • 200 g of 1-chloropropanedio-2,3 and 0.6 g of maleic anhydride are stirred at 100-105 ° C for 6 hours and the methanol formed is distilled off in a weak vacuum at 40-45 ° C .
  • 1.2 g of sodium bicarbonate are added to the mixture and the excess chloropropanediol is distilled off at 1 mbar and 130 ° C. bath temperature.
  • the colorless, viscous residue is diluted with 300 g of dimethyl sulfoxide and the solution is mixed with 154 g of sodium hydrogen carbonate.
  • the mixture is stirred at 95-105 ° C for 3 hours and filtered as usual.
  • the filtrate is slowly dripped into 3 liters of water.
  • the water, which contains the water-soluble constituents of the reaction mixture, is decanted, and the sticky polymer is dissolved with 600 ml of methyl glycol acetate with gentle heating.
  • the solution obtained is slowly dropped again in 3 l of water.
  • the aqueous phase is poured off again, the remaining sticky polymer is dried in a vacuum drying cabinet at approx. 100 ° C.
  • the polymer melts in the process and solidifies on cooling to a yellowish, glass-like, brittle mass which is soluble in glycol ethers or ether esters, but is insoluble in water.
  • a polyester is prepared from 45.1 g of 1,4-butanediol, 109.6 g of adipic acid and 0.5 g of p-toluenesulfonic acid in 175 g of toluene by removing the water of reaction by azeotropic distillation. After water no longer forms, the solution is mixed with 110.5 g of 1-chloropropanediol-2,3 and further heated to boiling on a water separator. 8.8 ml of water are separated off within 4 h. Then the toluene is distilled off at about 15 mbar, then the excess chloropropanediol at about 1 mbar and a bath temperature around 130 ° C.
  • Distillation residue is dissolved in 200 g of dimethyl sulfoxide and mixed with 67.3 g of sodium hydrogen carbonate, the mixture is stirred at 95-102 ° C within 4 hours.
  • Dimethyl sulfoxide distilled off.
  • the cyclocarbonate-containing polyester remains as a yellow to light brown, viscous liquid.
  • Adipic acid and 208.3 g of neopentyl glycol are added within
  • 210 C is a polyester with a molecular weight of 2100, acid number of 176 mg KOH / g and hydroxyl number of 13 mg
  • the volatile constituents are then distilled off at 10 mbar and 120.degree.
  • the resulting chlorohydrin product is mixed with 100 g of dimethylformamide and with 90 g
  • the cyclocarbonate-containing polyester is a light brown, tough material.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
PCT/DE1988/000451 1987-07-16 1988-07-15 Cyclocarbonate compounds WO1989000565A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19873723782 DE3723782A1 (de) 1987-07-16 1987-07-16 Verfahren zur herstellung von cyclocarbonatverbindungen
DEP3723782.9 1987-07-16

Publications (1)

Publication Number Publication Date
WO1989000565A1 true WO1989000565A1 (en) 1989-01-26

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EP (1) EP0390777A1 (enrdf_load_stackoverflow)
JP (3) JP2831671B2 (enrdf_load_stackoverflow)
DE (1) DE3723782A1 (enrdf_load_stackoverflow)
WO (1) WO1989000565A1 (enrdf_load_stackoverflow)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998034931A1 (en) * 1997-02-07 1998-08-13 Shell Internationale Research Maatschappij B.V. Process for the manufacture of epoxy compounds
US8703648B2 (en) 2009-11-26 2014-04-22 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Polysiloxane-modified polyhydroxy polyurethane resin, method for producing same, heat-sensitive recording material using the resin, imitation leather, thermoplastic polyolefin resin skin material, material for weather strip, and weather strip
EP2679644A4 (en) * 2011-02-24 2014-07-23 Dainichiseika Color Chem COATING COMPOSITION FOR FORMING A GAS BARRIER LAYER, GAS BARRIER FILM AND METHOD FOR PRODUCING THE GAS BARRIER FILM
US8951933B2 (en) 2009-11-25 2015-02-10 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Polysiloxane-modified polyhydroxy polyurethane resin, method for producing same, heat-sensitive recording material using the resin, imitation leather, thermoplastic polyolefin resin skin material, material for weather strip, and weather strip
US8975420B2 (en) 2009-11-25 2015-03-10 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Five-membered cyclocarbonate polysiloxane compound and process for preparation of same
US9359719B2 (en) 2011-04-04 2016-06-07 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Self-crosslinkable polysiloxane-modified polyhydroxy polyurethane resin, process for producing said resin, resin material comprising said resin, and artificial leather produced utilizing said resin
US9416227B2 (en) 2011-05-02 2016-08-16 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Polyhydroxyurethane microparticles, and process for producing same
US10000609B2 (en) 2010-08-26 2018-06-19 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Self-crosslinking polysiloxane-modified polyhydroxy polyurethane resin, resin material containing same, method for producing same, artificial leather comprising same, and thermoplastic polyolefin skin material comprising same
US10066048B2 (en) 2010-06-24 2018-09-04 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Self-crosslinkable polyhydroxy polyurethane resin, resinaceous material that contains the resin, process for production of the resin, and imitation leather, surfacing material and weatherstrip material, using the resin
WO2023182772A1 (ko) * 2022-03-22 2023-09-28 서울대학교산학협력단 알킬렌 카보네이트의 합성 방법
WO2025009749A1 (ko) * 2023-07-03 2025-01-09 서울대학교산학협력단 고리형 카보네이트의 합성방법

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Publication number Priority date Publication date Assignee Title
DE3804820A1 (de) * 1988-02-12 1989-08-17 Dainippon Ink & Chemicals Cyclocarbonathaltige ester und verfahren zu ihrer herstellung
US5514798A (en) * 1993-06-02 1996-05-07 Gilead Sciences, Inc. Method and cyclic carbonates for nucleotide analogues
US6120905A (en) * 1998-06-15 2000-09-19 Eurotech, Ltd. Hybrid nonisocyanate polyurethane network polymers and composites formed therefrom
JP5705511B2 (ja) * 2009-11-26 2015-04-22 大日精化工業株式会社 ポリシロキサン変性ポリヒドロキシポリウレタン樹脂、該樹脂含有組成物及び樹脂の製造方法
JP5601687B2 (ja) * 2011-01-12 2014-10-08 大日精化工業株式会社 熱可塑性ポリオレフィン樹脂製の表皮材
JP5637559B2 (ja) * 2010-12-22 2014-12-10 大日精化工業株式会社 擬革
JP5679739B2 (ja) * 2010-08-26 2015-03-04 大日精化工業株式会社 自己架橋型ポリシロキサン変性ポリヒドロキシポリウレタン樹脂およびその製造方法
JP2012162516A (ja) * 2010-11-19 2012-08-30 Mitsubishi Chemicals Corp ４−アルキニル−１，３−ジオキソラン−２−オン誘導体の製造法
CN105219125B (zh) * 2015-10-26 2017-06-16 江南大学 一种室温固化非异氰酸酯水性聚氨酯基高分子染料的制备方法
WO2017156132A1 (en) * 2016-03-08 2017-09-14 3D Systems, Incorporated Non-isocyanate polyurethane inks for 3d printing

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998034931A1 (en) * 1997-02-07 1998-08-13 Shell Internationale Research Maatschappij B.V. Process for the manufacture of epoxy compounds
US9394462B2 (en) 2009-11-25 2016-07-19 Dainichiseika Color & Chemicals Mfg. Co., Ltd Polysiloxane-modified polyhydroxy polyurethane resin, method for producing same, heat-sensitive recording material using the resin, imitation leather, thermoplastic polyolefin resin skin material, material for weather strip, and weather strip
US8951933B2 (en) 2009-11-25 2015-02-10 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Polysiloxane-modified polyhydroxy polyurethane resin, method for producing same, heat-sensitive recording material using the resin, imitation leather, thermoplastic polyolefin resin skin material, material for weather strip, and weather strip
US8975420B2 (en) 2009-11-25 2015-03-10 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Five-membered cyclocarbonate polysiloxane compound and process for preparation of same
US8703648B2 (en) 2009-11-26 2014-04-22 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Polysiloxane-modified polyhydroxy polyurethane resin, method for producing same, heat-sensitive recording material using the resin, imitation leather, thermoplastic polyolefin resin skin material, material for weather strip, and weather strip
US10066048B2 (en) 2010-06-24 2018-09-04 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Self-crosslinkable polyhydroxy polyurethane resin, resinaceous material that contains the resin, process for production of the resin, and imitation leather, surfacing material and weatherstrip material, using the resin
US10000609B2 (en) 2010-08-26 2018-06-19 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Self-crosslinking polysiloxane-modified polyhydroxy polyurethane resin, resin material containing same, method for producing same, artificial leather comprising same, and thermoplastic polyolefin skin material comprising same
US9540537B2 (en) 2011-02-24 2017-01-10 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Coating composition for forming gas barrier layer, gas barrier film, and method for producing gas barrier film
EP2865725A3 (en) * 2011-02-24 2015-05-27 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Coating composition for forming gas barrier layer, gas barrier film, and method for producing gas barrier film
EP2679644A4 (en) * 2011-02-24 2014-07-23 Dainichiseika Color Chem COATING COMPOSITION FOR FORMING A GAS BARRIER LAYER, GAS BARRIER FILM AND METHOD FOR PRODUCING THE GAS BARRIER FILM
US9359719B2 (en) 2011-04-04 2016-06-07 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Self-crosslinkable polysiloxane-modified polyhydroxy polyurethane resin, process for producing said resin, resin material comprising said resin, and artificial leather produced utilizing said resin
US9416227B2 (en) 2011-05-02 2016-08-16 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Polyhydroxyurethane microparticles, and process for producing same
WO2023182772A1 (ko) * 2022-03-22 2023-09-28 서울대학교산학협력단 알킬렌 카보네이트의 합성 방법
WO2025009749A1 (ko) * 2023-07-03 2025-01-09 서울대학교산학협력단 고리형 카보네이트의 합성방법

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Publication number Publication date
EP0390777A1 (de) 1990-10-10
JP2831671B2 (ja) 1998-12-02
JPH10265470A (ja) 1998-10-06
JPH03501121A (ja) 1991-03-14
JPH10251405A (ja) 1998-09-22
JP2854298B2 (ja) 1999-02-03
JP3072075B2 (ja) 2000-07-31
DE3723782C2 (enrdf_load_stackoverflow) 1989-10-19
DE3723782A1 (de) 1989-01-26

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