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WO1996005238A1 - Mousse de polyurethanne souple et procede de fabrication - Google Patents

Mousse de polyurethanne souple et procede de fabrication Download PDF

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Publication number
WO1996005238A1
WO1996005238A1 PCT/JP1995/000613 JP9500613W WO9605238A1 WO 1996005238 A1 WO1996005238 A1 WO 1996005238A1 JP 9500613 W JP9500613 W JP 9500613W WO 9605238 A1 WO9605238 A1 WO 9605238A1
Authority
WO
WIPO (PCT)
Prior art keywords
molasses
polyurethane foam
polyol
component
flexible polyurethane
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.)
Ceased
Application number
PCT/JP1995/000613
Other languages
English (en)
Japanese (ja)
Inventor
Hyoe Hatakeyama
Shigeo Hirose
Ken Kobashigawa
Tadaaki Tokashiki
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.)
National Institute of Advanced Industrial Science and Technology AIST
Tropical Technology Center Ltd
Original Assignee
Agency of Industrial Science and Technology
Tropical Technology Center Ltd
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 Agency of Industrial Science and Technology, Tropical Technology Center Ltd filed Critical Agency of Industrial Science and Technology
Publication of WO1996005238A1 publication Critical patent/WO1996005238A1/fr
Anticipated expiration legal-status Critical
Ceased 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
    • C08G18/06—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
    • C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
    • C08G18/6484—Polysaccharides and derivatives thereof
    • 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
    • C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
    • 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
    • C08G2110/00—Foam properties
    • C08G2110/0008—Foam properties flexible
    • 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
    • C08G2230/00—Compositions for preparing biodegradable polymers

Definitions

  • the present invention relates to a flexible polyurethane foam and a method for producing the same.
  • the present invention relates to a polyurethane foam and a method for producing the same, and more particularly, to a flexible polyurethane foam easily decomposed by microorganisms in a natural environment and a method for producing the same.
  • Brass chips are now widely used because of their ease of processing, price, lightness, and ease of use.
  • plastics unlike naturally occurring polymer compounds, are hardly decomposed by microorganisms in the natural world, causing environmental pollution and a major social problem.
  • blastic waste is hardly decomposed by the action of soil bacteria and the like, it remains in the dumped place for a long time, is very unsightly, and has caused problems in ecological environment.
  • polyurethane is prepared by reacting a polyol component and an isocyanate component.
  • this is also almost non-biodegradable like other plastics, and polyurethane foam has a large capacity. It was a major cause of environmental pollution.
  • Japanese Patent Publication No. 58-65605 discloses a hydrophilic urethane foam obtained by adding a powdered organic filler of microbes to a hydrophilic urethane foam.
  • No. 63-2842842, No. 2 describes a method in which a top crack or plant powder is combined with a urethane resin obtained by the reaction of a polyol containing an ester group with an organic polyisocyanate.
  • sheets and molded products that decompose in the natural world are disclosed.
  • molasses acts as a hard segment in the polyurethane, so that only a hard polyurethane can be obtained, and there is a problem that it cannot be used for applications requiring a soft polyurethane.
  • a soft K polyurethane foam having excellent properties can be obtained by selecting a component having a constant molecular weight as a polyol component to be combined with molasses.
  • the present invention has been completed.
  • the present invention provides the following two components (a) and (b)
  • Another object of the present invention is to use the above polyurethane foam for conversion. It is intended to provide a molasses polyol composition for a biodegradable flexible polyurethane foam.
  • the molasses of the component (a) is obtained from sugarcane, sugar beet, etc., and may be purified molasses or molasses, or molasses obtained after sugar production.
  • molasses is advantageous in terms of economy.
  • This molasses generally contains about 17 to 25% water, so remove this water as needed and use it.
  • the polyol component having an average molecular weight of 600 to 600 includes polyether-based and polyester-based polyols.
  • examples thereof include polyethylene glycol, polyvinylidene glycol, polyethylene adipate, polyethylene terephthalate, polycaprolactone, and polyester polyol (PES).
  • the isocyanate compound used in the present invention is not particularly limited, and may be an aliphatic polyisocyanate, an aliphatic polyisocyanate, an aromatic polyisocyanate, or a modified product thereof. And the like.
  • the aliphatic polyisocyanate includes, for example, hexamethylene diisocyanate (HDI), and the alicyclic polyisocyanate includes, for example, isophorone diisocyanate.
  • the aromatic polyisocyanate include, for example, tolylene diisocyanate (TDI), xylylene diisocyanate, diphenylmethane diisocyanate (MDI), polymer diphenyl methane diisocyanate, triphenyl, and the like.
  • Methane triisocyanate tris (isocyanate phenyl) thiophosphate and the like.
  • the modified polyisocyanate include urethane prepolymer, hexamethylene diisocyanate buret, hexamethylene diisocyanate trimer, isophorone diisocyanate trimer and the like.
  • tolylene diisocyanate (TDI) having a ratio of 2,4 isomer / 2,6 isomer of 80,20, that is, TDI-80 is considered to be the flexibility and workability of urethane foam. Is preferred.
  • the flexible polyurethane foam of the present invention is obtained by mixing the above molasses and a polyol component to form a molasses polyol composition for a biodegradable flexible polyurethane (hereinafter, referred to as “molasses polyol composition”), and then by a conventional method. It can be produced by reacting with a known isocyanate compound.
  • molasses polyol composition a biodegradable flexible polyurethane
  • a flexible polyurethane foam obtained by reacting with an isosilicate compound in the presence of an amine catalyst and a tin catalyst can be mentioned.
  • molasses as the component (a) and (ffi molecular polyol as the bd component) are mixed, and then an amine-based catalyst and a tin-based catalyst are preferably added thereto.
  • an amine-based catalyst and a tin-based catalyst are preferably added thereto.
  • Isoshiane Bok compound adding and mixing a small amount of water if necessary, 10 ⁇ : I 5 O e C , preferably 20: line by at temperatures of L 20 ° C, to atmospheric pressure or elevated pressure reaction
  • the (bj component) polymer polyol having an average molecular weight of 1000 to 6000 in the present embodiment may be a polyether or polyester polyol such as polyethylene glycol, polypropylene glycol, polyethylene adipate, or the like. It is preferable to use a polyol such as polyethylene terephthalate or polycaprolactone.
  • the number of functional groups of the high molecular polyol is preferably divalent or trivalent, and the more preferable (bt) component has an average molecular weight of 3000 to 6000.
  • a tin-based catalyst can be used as a catalyst for the urethane reaction.
  • the reaction becomes too fast to obtain a polyurethane foam having preferable physical properties. More preferably, both of the system catalysts are used.
  • amine catalysts include diazabicyclooctane (DABCO), N-ethylmorpholine (NEM), triethylamine (TEA), N, ⁇ , ⁇ ', ⁇ ', ⁇ '-pentyl methyl getyl triamine (PMDETA) and the like, and tin-based catalysts such as sodium succinate (SO) and dibutyltin dilaurate (DBTDL).
  • DABCO diazabicyclooctane
  • NEM N-ethylmorpholine
  • TAA triethylamine
  • PMDETA triethylamine
  • tin-based catalysts such as sodium succinate (SO) and dibutyltin dilaurate (DBTDL).
  • SO sodium succinate
  • DBTDL dibutyltin dilaurate
  • the compounding amounts of the above-mentioned components are as follows: (a) 0.1 to 99.9% by weight (hereinafter simply referred to as “%”), (b) 0.1 to 99.9%, and isocyanate compound in 0.1%.
  • % 0.1 to 99.9% by weight
  • isocyanate compound in 0.1%.
  • the component (a) is in the range of 10 to 30%
  • the component (bi) is in the range of 30 to 60%
  • the content of the isocyanate compound is in the range of 10 to 60%.
  • amine catalysts and tin catalysts are presumed to be about 0.01 to 20% for amine catalysts and about 0.01 to 20% for tin catalysts.
  • the weight ratio of amine catalyst to tin catalyst is 10%. : 1 to 1: about 10 should be sufficient.
  • a molasses polyol composition is prepared by adding a polyol having an average molecular weight of 200 to 400 and selected from ethylene glycol, polyethylene glycol, and glycerin (hereinafter, referred to as “low molecular polyol”). And a flexible polyurethane foam obtained by reacting the same.
  • molasses component (a) a low molecular weight polyol which is the component (c), were mixed and dissolved, then this (b 2) molasses polyol composition added polymeric polyol is a component The product is converted and this is reacted with an isocyanate compound to produce a flexible polyurethane foam.
  • Component (c) a low-molecular-weight polyol having an average molecular weight of 200 to 400 and selected from ethylene glycol, polyethylene glycol (PEG), and glycerin, has an action of dissolving molasses.
  • the low-molecular polyol is preferably the above-mentioned one.
  • polyols polyols such as PEG-polyvinylene glycol, polyester polyol, and polyester polyol having a higher molecular weight
  • molasses can be sufficiently dissolved. Is difficult.
  • As ⁇ Ko polyols (b 2) component in the present embodiment the average molecular weight of 60 0 to 3000, PEG, polypropylene glycol (PPG), to use a polyol selected from polyester polyols (PE S) preferred.
  • PEG polypropylene glycol
  • PE S polyester polyols
  • PEG can soften polyurethane from those having an average molecular weight of 600 or more, and is solid (room temperature) from a molecular weight of 1000 or more, but molasses polyol up to an average molecular weight of about 3000. Pour point below the temperature at which the composition does not denature Since it does not have a particular viscosity, it is possible to use those having this range, that is, those having an average molecular weight in the range of 600 to 3,000.
  • PPG and PES it is preferable to use those having an average molecular weight in the range of 1000 to 4000 and an average molecular weight of 1000 to 3000 for the same reason as PEG.
  • examples of PES include polycabrolactone.
  • the amount of each component in the molasses polyol composition of this embodiment is 10 to 25 wt.%, (B 2) component 35 to 65%, be about 25 to 40% (c) component , in particular, (a) component 12 to 20% (b 2) component 40 to 60%, and preferably in the range of 28 to 40% (c) component.
  • the molasses polyol composition thus obtained can be used as it is as a polyol component of polyurethane.However, in order to obtain a better polyurethane, water derived from molasses is removed from the molasses polyol composition. However, it is preferable to reduce the water content to about 0.1 to 15%.
  • the isocyanate compound that reacts with the polyol component has high reactivity with water, if the amount of water in the polyol component is large, the foaming reaction between the isocyanate compound and water proceeds preferentially, and the isocyanate compound
  • the gelation reaction between the resin and the polyol does not proceed sufficiently, causing non-uniform cells, insufficient strength of the cell membrane, etc., reducing the strength of the polyurethane resin as a whole, and since the reaction is a heat-generating reaction, The inside of the polyurethane is burnt, making it impossible to obtain polyurethane with excellent physical properties.
  • a reduced pressure moat method As a method for removing water from the molasses polyol composition, there are a reduced pressure moat method, a freeze-drying method, and the like. Among them, under a reduced pressure of about 40 to 0.01 Torr, at a temperature of about 30 to 9 CTC. A reduced pressure reduction method for removing water is preferred.
  • the molasses polyol composition of the present embodiment obtained as described above is mixed with, for example, a polyisocyanate compound and, if necessary, a small amount of water, and then mixed to 10 to 150. (:, Preferably 20 to: I 20.
  • a polyisocyanate compound for example, a polyisocyanate compound, if necessary, a small amount of water, and then mixed to 10 to 150.
  • a polyisocyanate compound if necessary, a small amount of water
  • the proportion of the polyisocyanate compound used in the production of the polyurethane of the present embodiment is 25 to 75%, preferably 35 to 65%.
  • the molasses polyol composition which is a mixture of the component (a) and the component (b) can be subjected to rapid centrifugal separation, if necessary, to remove insoluble matters. separation temperature of approximately 1 0-6 O e C, 2, 0 0 0 to 8, may be performed 1 0-6 0 min 0 0 0 rpm about the rotational speed.
  • a non-flammable organic solvent such as methylene chloride may be used for the reaction, if necessary.
  • the ureinization reaction is carried out in a molding die having a predetermined shape, whereby a polyurethane foam having an arbitrary shape, for example, a sheet-like, plate-like, column-like, container-like, etc. It can be.
  • Polyurethane foams made by using the honey polyol composition of the present invention become flexible polyurethanes because the rigidity of molasses, which acts as a hard segment in the polyurethane, is reduced by the action of the polymer polyol. Polyurethane foam having properties is obtained.
  • Example 1 the molasses component incorporated in the polyurethane foam is rapidly decomposed by the action of microorganisms in the soil or the like after disposal, and shows biodegradability.
  • Molasses moisture content: about 20% (10 g) was weighed into 90 g of polypropylene glycol 3000 (PPG 3000, average molecular weight 3000; diol type), and mixed and stirred with a mixing stirrer for about 1 hour. 4 g of water in the obtained mixture lO Og, 3.3 g of a foam stabilizer (NUC Silicone L-520; manufactured by Nippon Tunica Co., Ltd.), 0.07 g of tin-based catalyst (di-n-butyltin dilaurate) and amine Add 0.7 g of diazabicyclooctane catalyst and mix well.
  • PPG 3000 polypropylene glycol 3000
  • diol type diol type
  • the obtained polyurethane foam had a density of 0.021 gZcm 2 and a 25% compressive strength of 0.90 kPa.
  • Polyurethane foams were prepared in the same manner as in Example 1 except that the amounts of the components were changed as shown in Table 1 (Products of the present invention 2 and 3).
  • the obtained polyurethane foam had a density of 0.02 g.Zcm 2 and a compressive strength of 30 kPa.
  • Polyurethane foams were prepared in the same manner as in Example 3 except that the amounts of the components were changed as shown in Table 2 (Products of the present invention 5 to 9).
  • Molasses (moisture content 19.6%) 2 Og was weighed into 40 g of polyethylene glycol 200 (PEG200, average molecular weight 200) and mixed with a mixing stirrer for about 1 hour. The mixture was stirred. Then, the mixture was centrifuged at 8000 rpm for 20 minutes using a fast-centrifuge to remove solid residue. The supernatant liquid after centrifugation was reduced under reduced pressure at 1 Torr for 4 hours using a centrifugal evaporator. Further, 80 g of polypropylene glycol 3000 (PPG3000, average molecular weight 3000) was added to 20 g of the obtained solution to obtain 100 g of a molasses polyol composition.
  • PPG3000 average molecular weight 3000
  • Polyurethane foam thus obtained has a density of 0.028 gZc m 3. 25% compressive strength is 1.40 k P a, ⁇ ratio was 37.7 kPa.
  • Example 6
  • a polyurethane foam was produced in the same manner as in Example 5 except that the amounts of the components were changed as shown in Table 3 (Product 11 of the present invention).
  • the polyurethane foam thus obtained had a density of 0.030 gZcm 3 , a 25% compressive strength of 1.58 kPa, and an elastic modulus of 21.2 kPa.
  • the polyurethane foam thus obtained was a flexible foam in which cells were connected, and the density was 0.14 gZcm 3 .
  • Molasses (moisture content: 19.6%) (20 g) was weighed into 40 g of PEG200, and mixed and stirred with a mixing stirrer for about 1 hour. Then, the mixture was centrifuged at 8000 rpm for 20 minutes using a centrifugal separator to remove solid residue. The supernatant liquid after the fast-centrifugal separation was concentrated under reduced pressure at a pressure of 1 Torr for 4 hours using a fast-heart evaporator. Further, 50 g of PEG600 was added to 50 g of the obtained solution to obtain 10 Og of a molasses polyol composition.
  • Molasses (moisture content 19.6%) 20 g was weighed in 4 Og of PEG200, and mixed and stirred for about 1 hour with a mixing stirrer. Next, the mixture was centrifuged at 8000 rpm for 20 minutes using a centrifuge to remove solid residue. After centrifugation, the supernatant was concentrated under reduced pressure at a pressure of 1 T rr for 4 hours using a fast-center evaporator. Furthermore, 50 g of polypropylene glycol 3000 (PPG3000, average molecular weight 3000) was added to 50 g of the obtained solution to obtain 100 g of a molasses polyol composition.
  • PPG3000 average molecular weight 3000
  • the polyurethane foam thus obtained was a flexible foam in which cells were connected, and had a density of 0.018 gZcm 3 . Comparative Example 1
  • molasses polyol composition molasses (moisture content 19.6%) 20 g was weighed in 40 g of PEG200, and mixed and stirred for about 1 hour with a mixing and stirring machine. Then, the mixture was subjected to quick-centrifugation at 80 OO rpm for 20 minutes by a quick-centrifuge to remove solid residue. The supernatant liquid after centrifugation was reduced under reduced pressure at 1 Torr for 4 hours using a centrifugal evaporator to obtain 60 g of a molasses polyol composition.
  • the polyurethane foam thus obtained had a density of 0.040 gZcm 3 , a compressive strength of 412.1 kPa and an elastic modulus of 29.2 MPa. Comparative Examples 2 and 3
  • Polyurethane foam was converted in the same manner as in Comparative Example 1 except that the amounts of the components were changed as shown in Table 4 (Comparative products 2 and 3).
  • Comparative Product 2 has a density of 0.034 g / cm 3 , a compressive strength of 230.2 kPa, and an elastic modulus of 16.7 MPa
  • Comparative Product 3 has a density of 0.045 g / c and a compressive strength of 434.9 kPa.
  • the elastic modulus was 32.2 MPa.
  • the polyurethane foam of the present invention had the same flexibility as the conventional flexible polyurethane foam while incorporating molasses. It was also excellent in biodegradability and decomposed rapidly in nature.
  • the polyurethane foam of the present invention has the same physical properties as a conventional flexible polyurethane foam, and is naturally biodegradable after it is no longer needed, and is naturally used as a material for agricultural and agricultural industries. It can be widely used for home use, industrial use, etc.

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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

L'invention concerne une mousse de polyuréthanne souple produite par la réaction d'un composé isocyanate avec (a) des mélasses et (b) un composé polyol ayant un poids moléculaire moyen entre 600 et 6000. L'invention concerne également un procédé pour produire cette mousse et une composition de mélasses/polyol destinée à la fabrication d'une mousse de polyuréthanne souple et biodégradable. Cette mousse a une souplesse similaire à celle des mousses de polyuréthanne souples usuelles, en dépit de l'incorporation de mélasses, et sa biodégradabilité est excellente, si bien qu'elle peut se dégrader rapidement dans l'environnement naturel. Comme la mousse a des propriétés similaires à celles de mousses de polyuréthanne souples usuelles et qu'elle peut se dégrader spontanément après son utilisation, elle peut être utilisée à grande échelle, non seulement en agriculture et en horticulture, mais également dans des applications domestiques et industrielles.
PCT/JP1995/000613 1994-08-17 1995-03-30 Mousse de polyurethanne souple et procede de fabrication Ceased WO1996005238A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP6214289A JPH0859782A (ja) 1994-08-17 1994-08-17 軟質ポリウレタンフォームおよび製造法
JP6/214289 1994-08-17

Publications (1)

Publication Number Publication Date
WO1996005238A1 true WO1996005238A1 (fr) 1996-02-22

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PCT/JP1995/000613 Ceased WO1996005238A1 (fr) 1994-08-17 1995-03-30 Mousse de polyurethanne souple et procede de fabrication

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WO (1) WO1996005238A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1203776A3 (fr) * 2000-10-17 2003-01-15 Canon Kabushiki Kaisha Composite à base de résine, méthode pour le produire et articles le comprenant

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100355799C (zh) * 2003-06-06 2007-12-19 伊藤制油株式会社 聚氨酯及其制造方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5374597A (en) * 1976-12-14 1978-07-03 Toyo Rubber Chem Ind Co Ltd Manufacture of flexible or semi-rigid polyurethane foam
JPS5374596A (en) * 1976-12-14 1978-07-03 Toyo Rubber Chem Ind Co Ltd Manufacture of rigid polyurethane foam
JPS58502151A (ja) * 1981-12-08 1983-12-15 ケネデイ，リチヤ−ド　ビイ． ポリウレタン発泡体とその製造方法
JPH05186556A (ja) * 1991-02-04 1993-07-27 Agency Of Ind Science & Technol 生分解性ポリウレタン及びその製造方法
JPH06128348A (ja) * 1992-10-14 1994-05-10 Agency Of Ind Science & Technol 生分解性ポリウレタン複合体及びその製造方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5374597A (en) * 1976-12-14 1978-07-03 Toyo Rubber Chem Ind Co Ltd Manufacture of flexible or semi-rigid polyurethane foam
JPS5374596A (en) * 1976-12-14 1978-07-03 Toyo Rubber Chem Ind Co Ltd Manufacture of rigid polyurethane foam
JPS58502151A (ja) * 1981-12-08 1983-12-15 ケネデイ，リチヤ−ド　ビイ． ポリウレタン発泡体とその製造方法
JPH05186556A (ja) * 1991-02-04 1993-07-27 Agency Of Ind Science & Technol 生分解性ポリウレタン及びその製造方法
JPH06128348A (ja) * 1992-10-14 1994-05-10 Agency Of Ind Science & Technol 生分解性ポリウレタン複合体及びその製造方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
POLYMER PREPRINTS, JAPAN, Vol. 42, No. 4, (1993), Published by KOBUNSHI GAKKAI, SHIGEO HIROSE et al., "Preparation and Physical Properties of Biodegradable Polyurethane Starting from Molasses", p. 1341. *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1203776A3 (fr) * 2000-10-17 2003-01-15 Canon Kabushiki Kaisha Composite à base de résine, méthode pour le produire et articles le comprenant
US6828402B2 (en) 2000-10-17 2004-12-07 Canon Kabushiki Kaisha Resin composite, method for producing the same and articles consisting of the same

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Publication number Publication date
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