CN109153761B - Process for producing polyurethane foam sheet - Google Patents
Process for producing polyurethane foam sheet Download PDFInfo
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- CN109153761B CN109153761B CN201780030576.4A CN201780030576A CN109153761B CN 109153761 B CN109153761 B CN 109153761B CN 201780030576 A CN201780030576 A CN 201780030576A CN 109153761 B CN109153761 B CN 109153761B
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- polyurethane foam
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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
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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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
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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
The invention aims to provide a method for stably manufacturing a polyurethane foam sheet with excellent touch and mechanical strength. The present invention provides a method for producing a polyurethane foam sheet, comprising a polyurethane composition containing a main agent (i) containing a urethane prepolymer (a) having an isocyanate group and a curing agent (ii) containing a polyol (B), wherein the main agent (i) and the curing agent (ii) are mixed together, and an inert gas is supplied to the main agent (i) and/or the curing agent (ii) under a pressure in the range of 0.05 to 0.2 MPa.
Description
Technical Field
The present invention relates to a method for producing a polyurethane foam sheet having excellent touch and mechanical properties.
Background
Polyurethane foam sheets are widely used in various fields such as automobile interior materials, shoe soles, copying machine rollers, cushioning materials, sealing materials, and electronic sealing materials. As a method for producing the polyurethane foam sheet, for example, the following methods are widely used: the urethane foam is produced by mixing a urethane prepolymer having an isocyanate group with a polyol composition containing water or the like, and simultaneously performing urethane resination and foaming (for example, see patent document 1). However, in such foaming with water, the touch is hardened by the formation of urea bonds, and it is difficult to obtain a foamed sheet having a soft and bulky feeling.
As a method for producing the polyurethane foam sheet, for example, a method using a mechanical foaming (mechanical stirring) method is known in which, when two liquids are mixed, a reaction of the two liquids is started while blowing an inert gas (see, for example, patent document 2). However, in such a method of introducing an inert gas when mixing two liquids, if the liquid viscosity is not within a certain constant range, stable foam cannot be maintained, and it is difficult to stably obtain a foamed sheet.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 2013-053265
Patent document 2: japanese laid-open patent application No. 2001 and 089547
Disclosure of Invention
Problems to be solved by the invention
An object of the present invention is to provide a method for stably producing a polyurethane foam sheet having excellent touch and mechanical strength.
Means for solving the problems
The present invention provides a method for producing a polyurethane foam sheet, comprising a polyurethane composition containing a main agent (i) containing a urethane prepolymer (a) having an isocyanate group and a curing agent (ii) containing a polyol (B), wherein the main agent (i) and the curing agent (ii) are mixed together, and an inert gas is supplied to the main agent (i) and/or the curing agent (ii) under a pressure in the range of 0.05 to 0.2 MPa.
Effects of the invention
According to the production method of the present invention, a polyurethane foam sheet having excellent touch and mechanical strength can be obtained while maintaining stable foam generated by an inert gas.
Detailed Description
In the method for producing a polyurethane foam sheet of the present invention, before the main agent (i) and the curing agent (ii) are mixed, an inert gas is applied to the main agent (i) and/or the curing agent (ii) under a pressure in the range of 0.05 to 0.2 MPa.
As the urethane prepolymer (A) having an isocyanate group, for example, a reaction product of a polyol (a-1) and a polyisocyanate (a-2) can be used.
Examples of the polyol (a-1) include polycarbonate polyols, polyether polyols, polyester polyols, polyacrylic polyols, and polybutadiene polyols. These polyols may be used alone or in combination of two or more.
The number average molecular weight of the polyol (a-1) is preferably 700 to 10,000, more preferably 800 to 6,000, from the viewpoint of obtaining good mechanical properties. The number average molecular weight of the polyol (a-1) is a value measured by a Gel Permeation Chromatography (GPC) method under the following conditions.
A measuring device: high efficiency GPC apparatus (HLC-8220 GPC, manufactured by Tosoh corporation)
A chromatographic column: the following columns manufactured by Tosoh corporation were connected in series for use.
"TSKgel G5000" (7.8 mmI.D.. times.30 cm). times.1 roots
"TSKgel G4000" (7.8mm I.D.. times.30 cm). times.1 roots
"TSKgel G3000" (7.8 mmI.D.. times.30 cm). times.1 roots
"TSKgel G2000" (7.8 mmI.D.. times.30 cm). times.1 roots
A detector: RI (differential refractometer)
Column temperature: 40 deg.C
Eluent: tetrahydrofuran (THF)
Flow rate: 1.0 mL/min
Injection amount: 100 μ L (tetrahydrofuran solution with a sample concentration of 0.4% by mass)
Standard sample: the standard curve was made using the following standard polystyrene.
(Standard polystyrene)
TSKgel Standard polystyrene A-500 manufactured by Tosoh corporation "
TSKgel Standard polystyrene A-1000 manufactured by Tosoh corporation "
TSKgel Standard polystyrene A-2500 manufactured by Tosoh corporation "
TSKgel Standard polystyrene A-5000 manufactured by Tosoh corporation "
TSKgel Standard polystyrene F-1 manufactured by Tosoh corporation "
TSKgel Standard polystyrene F-2 manufactured by Tosoh corporation "
TSKgel Standard polystyrene F-4 manufactured by Tosoh corporation "
TSKgel Standard polystyrene F-10 manufactured by Tosoh corporation "
TSKgel Standard polystyrene F-20 manufactured by Tosoh corporation "
TSKgel Standard polystyrene F-40 manufactured by Tosoh corporation "
TSKgel Standard polystyrene F-80 manufactured by Tosoh corporation "
TSKgel Standard polystyrene F-128 manufactured by Tosoh corporation "
TSKgel Standard polystyrene F-288 manufactured by Tosoh corporation "
TSKgel Standard polystyrene F-550 manufactured by Tosoh corporation "
In the polyol (a-1), a chain extender having a number average molecular weight of 50 to 450 may be used in combination as necessary.
As the chain extender, for example: ethylene glycol, propylene glycol, 1, 3-propanediol, 1, 4-butanediol, 1, 3-butanediol, 1, 2-butanediol, 2-methyl-1, 3-propanediol, 1, 5-pentanediol, neopentyl glycol, 1, 6-hexanediol, 1, 5-hexanediol, 3-methyl-1, 5-pentanediol, chain extenders having a hydroxyl group such as 1, 7-heptanediol, 1, 8-octanediol, 1, 9-nonanediol, 1, 8-nonanediol, 2-ethyl-2-butyl-1, 3-propanediol, 1, 10-decanediol, 1, 12-dodecanediol, 1, 4-cyclohexanedimethanol, 1, 3-cyclohexanedimethanol, trimethylolpropane, trimethylolethane, and glycerin; and chain extenders having an amino group such as ethylenediamine, 1, 2-propylenediamine, 1, 6-hexamethylenediamine, piperazine, 2, 5-dimethylpiperazine, isophoronediamine, 1, 2-cyclohexanediamine, 1, 3-cyclohexanediamine, 1, 4-cyclohexanediamine, 4 ' -dicyclohexylmethanediamine, 3 ' -dimethyl-4, 4 ' -dicyclohexylmethanediamine, 1, 4-cyclohexanediamine, and hydrazine. These chain extenders may be used alone or in combination of two or more.
As the polyisocyanate (a-2), for example: aromatic polyisocyanates such as polymethylene polyphenyl polyisocyanate, diphenylmethane diisocyanate, polymeric diphenylmethane diisocyanate, carbodiimide-modified diphenylmethane diisocyanate, phenylene diisocyanate, tolylene diisocyanate, and naphthalene diisocyanate; aliphatic or alicyclic polyisocyanates such as hexamethylene diisocyanate, lysine diisocyanate, cyclohexane diisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, xylylene diisocyanate, and tetramethylxylylene diisocyanate. These polyisocyanates may be used alone or in combination of two or more. Among these, aromatic polyisocyanates are preferably used, and diphenylmethane diisocyanate is more preferably used, from the viewpoint of obtaining further excellent reactivity and mechanical strength.
The method for producing the urethane prepolymer (a) can be produced, for example, by the following steps: the polyol (a-1) is added dropwise to a reaction vessel containing the polyisocyanate (a-2), and then the reaction vessel is heated to cause the reaction under conditions in which the isocyanate group of the polyisocyanate (a-2) is excessive relative to the hydroxyl group of the polyol (a-1).
The equivalent ratio ([ NCO/OH ]) of the isocyanate group of the polyisocyanate (a-2) to the hydroxyl group of the polyol (a-1) in producing the urethane prepolymer (a) is preferably in the range of 1.5 to 25, and more preferably in the range of 3 to 15, from the viewpoint of further improving the mechanical strength.
The content of the isocyanate group (hereinafter referred to as "NCO%") in the urethane prepolymer (a) is preferably in the range of 4 to 20 mass%, more preferably in the range of 5 to 18 mass% from the viewpoints of further improvement in mechanical strength, high solubility of the inert gas to be loaded, and further excellent retention of the inert gas to be loaded. The content of isocyanate groups in the urethane prepolymer (a) is expressed in accordance with jis k 1603-1: 2007 and values determined by potentiometric titration.
As the polyol (B), for example, the same polyol as the polyol (a-1) which is a raw material of the urethane prepolymer (A) can be used. These polyols may be used alone or in combination of two or more.
In the polyol (B), the same chain extender as that described above may be used in combination as necessary. These chain extenders may be used alone or in combination of two or more.
The polyurethane composition used in the present invention contains a main agent (i) containing the urethane prepolymer (a) and a curing agent (ii) containing the polyol (B), and may contain other additives as needed.
As the above-mentioned other additives, for example: catalysts, foam regulators, antioxidants, thixotropy imparting agents, plasticizers, stabilizers, inorganic fillers, organic fillers, dyes, pigments, and the like. These additives may be used alone or in combination of two or more, and may be contained in either one of the main agent (i) and the curing agent (ii), and are preferably contained in the curing agent (ii) from the viewpoint of improving the stability of the urethane prepolymer (a). In the present invention, the curing agent (ii) may further contain water, and water may be used in combination with gas application described later for foaming.
Next, a method for producing the polyurethane foam sheet of the present invention will be described.
In the method for producing a polyurethane foam sheet, it is necessary to: before mixing the main agent (i) and the curing agent (ii), an inert gas is applied to the main agent (i) and/or the curing agent (ii) under a pressure in the range of 0.05 to 0.2 MPa.
The gas loading refers to a process of forcibly incorporating an inert gas into the main agent (i) and/or the curing agent (ii) by allowing the inert gas to enter from the outside under pressure. In addition, when the inert gas is introduced, it is preferable to stir the main agent (i) and/or the curing agent (ii) from the viewpoint of improving the solubility of the inert gas. The gas loading may be performed using a known loading device.
As the inert gas, for example: carbon dioxide, helium, nitrogen, argon, neon, and the like. Among these, carbon dioxide is preferably used from the viewpoint of ease of starting materials and high solubility in the main agent (i) and the curing agent (ii).
The pressure at the time of the gas application is required to be in the range of 0.05 to 0.2MPa in order to maintain stable bubbles generated by the inert gas. When the pressure is less than 0.05MPa, good foam cannot be incorporated, and the resulting polyurethane foam sheet is hard and has a poor touch; in addition, when it exceeds 0.2MPa, there are problems as follows: cavitation occurs during circulation and discharge of the injection-foaming machine, and a liquid cannot be stably discharged, and a uniform polyurethane foam sheet cannot be obtained. The pressure is preferably in the range of 0.07 to 0.18MPa, and more preferably in the range of 0.08 to 0.17MPa, from the viewpoint of maintaining more uniform bubbles and obtaining more excellent touch.
The time for applying the gas is preferably 10 minutes to 3 hours, and more preferably 10 to 60 minutes, from the viewpoint of uniformly applying the inert gas and preventing deterioration of the urethane prepolymer and the polyol.
The gas loading is preferably performed only on the main agent (i). The reason for this is as follows: when gas loading is performed under the same conditions (pressure and time), the solubility of the inert gas, which is the main component (i), is higher than that of the curing agent (ii), and thus a polyurethane foam sheet that easily maintains stable foam can be obtained.
The viscosity of the main agent (i) at 50 ℃ when the gas is applied is preferably in the range of 200 to 20,000 mPas, more preferably in the range of 250 to 15,000 mPas, from the viewpoint that the inert gas can be applied well even under the above pressure. The viscosity of the base (i) at 50 ℃ is a value measured by a B-type viscometer (rotor No.3, rotation speed: 12 rpm).
When the main agent (i) is subjected to the gas loading, the specific gravity of the main agent (i) immediately after the gas loading is released to the normal pressure is preferably in the range of 0.2 to 0.8, and more preferably in the range of 0.3 to 0.7, from the viewpoint of obtaining more excellent retention of bubbles and feeling.
After the gas loading, there may be mentioned: a method in which the main agent (i) and the curing agent (ii) are mixed together after the pressure is temporarily returned to normal pressure, and a urethanization reaction is carried out; and (ii) a method in which the main agent (i) and/or the curing agent (ii) to which the gas has been applied are moved to a mixer or the like connected to an application device by a pressure difference, and are mixed by the mixer or the like to carry out the urethanization reaction.
As a mixing ratio of the main agent (i) and the curing agent (ii), (i): (ii) preferably, the mass ratio is in the range of 80: 20 to 20: 80, and more preferably in the range of 75: 25 to 25: 75.
Then, the mixed main agent (i) and curing agent (ii) are applied to, for example, a release paper or a base material coated with a release agent and cured to obtain a polyurethane foam sheet.
Examples of a method for applying the mixed main agent (i) and the mixed curing agent (ii) include a method using an applicator, a roll coater, a spray coater, a T-die coater, a knife coater, and the like. The thickness of the coating is, for example, in the range of 10 to 500. mu.m.
Examples of the curing include: the method is carried out at the temperature of 60-100 ℃ for 1 minute-1 hour. Can be further cured for 1 to 3 days at the temperature of 40 to 80 ℃.
The density of the polyurethane foam sheet obtained by the above method is preferably 0.5 to 0.95g/cm from the viewpoint of obtaining a good touch3More preferably 0.65 to 0.9g/cm3The range of (1). The method for measuring the density of the polyurethane foam sheet is described in examples described below.
Examples
The present invention will be described in more detail below with reference to examples.
Production example 1 production of Main component (i-1)
100 parts by mass of 4, 4' -diphenylmethane diisocyanate (hereinafter abbreviated as "MDI") and 230 parts by mass of a polyether polyol (EXCENOL 240, manufactured by Asahi glass company, having a number average molecular weight of 3,000, hereinafter abbreviated as "PEt-1") were charged in a four-necked flask equipped with a thermometer, a stirrer, an inert gas inlet and a reflux condenser, and reacted at 80 ℃ for 3 hours to obtain NCO%: 7.2% by mass of a urethane prepolymer. This was used as the main agent (i-1). The viscosity of the main agent (i-1) at 50 ℃ is 1,240 mPas.
Production example 2 production of curing agent (ii-1)
100 parts by mass of a polyether polyol (EXCENOL 240, manufactured by Asahi glass company, having a number average molecular weight of 4,900), 2 parts by mass of ethylene glycol, 1 part by mass of glycerin, 0.3 part by mass of triethylenediamine as an amine catalyst, 0.5 part by mass of TOYOCAT ET, manufactured by Tosoh Corp., Ltd., and 0.5 part by mass of SZ-1328E, manufactured by Tolyokang Corp., Ltd., as a foam stabilizer were mixed and stirred to obtain a curing agent (ii-1).
[ example 1]
The above-mentioned main agent (i-1) is charged into a loading apparatus. Then, carbon dioxide (abbreviated as "CO" in Table 1) was used2". ) The pressure in the loading device was increased to 0.1MPa, and the raw material was loaded for 30 minutes while being stirred.
Then, the gas-loaded base compound (i-1) was charged into a base compound tank of a low-pressure urethane injection foaming machine "MT 5" manufactured by Polymer Engineering, Inc. through a charging device by a pressure difference, and circulated under a pressure of 0.05 MPa. The curing agent (ii-1) was also charged into the curing agent tank, and circulated under a pressure of 0.05 MPa. Then, (i-1) and (ii-1) were simultaneously discharged at a mass ratio of 130: 100, mixed instantaneously, and then the mixed solution was applied to a sheet coated with a release agent and heated at 80 ℃ for 10 minutes to obtain a polyurethane foamed sheet.
In parallel with this, the specific gravity of the base compound (i-1) immediately after the loading device was released to normal pressure was measured, and found to be 0.6.
[ example 2]
A polyurethane foam sheet was obtained in the same manner as in example 1, except that the pressure at the time of carbon dioxide application was changed to 0.15 MPa. In addition, the specific gravity of the base compound (i-1) immediately after the loading device was released to normal pressure was measured in the same manner, and found to be 0.4.
[ example 3]
The above curing agent (ii-1) was charged into a loading apparatus. Then, the inside of the charging device was pressurized to 0.15MPa with carbon dioxide, and the raw material was charged for 30 minutes while being stirred.
Then, the base compound (i-1) and the curing agent (ii-1) after gas loading were introduced into a tank of a low-pressure urethane injection foaming machine "MT 5" manufactured by Polymer Engineering, and the mixture was circulated under a pressure of 0.05 MPa. Then, (i-1) and (ii-1) were simultaneously discharged so that the mass ratio became 130: 100, and after instantaneous mixing, the mixed solution was applied to a sheet coated with a release agent and heated at 80 ℃ for 10 minutes to obtain a polyurethane foamed sheet.
In parallel with this, the specific gravity of the curing agent (i-1) immediately after the loading device was released to normal pressure was measured, and found to be 0.66.
Comparative example 1
Gas application was performed in the same manner as in example 1 except that the pressure at the time of carbon dioxide application was changed to 0.8MPa, but cavitation was generated, and discharge of carbon dioxide could not be stably performed, and a uniform foamed sheet could not be obtained. Therefore, the subsequent physical property measurement was not performed, and therefore, it is indicated as "-".
Comparative example 2
A polyurethane foam sheet was obtained in the same manner as in example 3, except that the pressure at the time of carbon dioxide application was changed to 0.03 MPa. Further, the specific gravity of the curing agent (i-1) immediately after the charging device was released to normal pressure was similarly measured, and found to be 0.85.
[ method for measuring Density of polyurethane foam sheet ]
The polyurethane foam sheets obtained in examples and comparative examples were cut into a length of 10cm and a width of 10cm, the thickness and weight were measured, and the density was calculated according to the following formula (1).
Density (g/cm)3) Weight (g)/10(cm) × 10(cm) × thickness (cm) (1)
[ method for evaluating touch feeling of polyurethane foam sheet ]
The feel of the polyurethane foam sheets obtained in examples and comparative examples was evaluated by feel as follows.
"A": has excellent flexibility.
"B": has good flexibility.
"C": hard or with unevenness.
[ method for measuring mechanical Strength of polyurethane foam sheet ]
The polyurethane foam sheets obtained in examples and comparative examples were cut into a width of 5mm, a length of 7cm and a thickness of 100. mu.m, and the resulting sheets were used as test pieces. The test piece was measured for 100% modulus (MPa), stress at break (MPa) and elongation at break (%) using AUTOGRAPH (manufactured by Shimadzu corporation) "G-I" at a crosshead speed of 300 mm/min.
[ Table 1]
Therefore, the following steps are carried out: the polyurethane foam sheet obtained by the production method of the present invention can stably retain bubbles generated by an inert gas, and therefore has an excellent feel. In addition, it can be seen that: the mechanical strength is also excellent.
On the other hand, in comparative example 1, in a mode in which the pressure at the time of gas application was out of the range specified in the present invention, cavitation was generated, and the discharge of carbon dioxide could not be stably performed, and a uniform foamed sheet could not be obtained.
In comparative example 2, the pressure at the time of gas application was lower than the range specified in the present invention, and even if gas application was performed for a long time, the retention of bubbles was not good, and the feel was hard and poor.
Claims (2)
1. A process for producing a polyurethane foam sheet, which comprises a polyurethane composition comprising a main agent i containing a urethane prepolymer A having an isocyanate group and a curing agent ii containing a polyol B,
the content of the isocyanate group in the urethane prepolymer A is in the range of 4 to 20% by mass,
before mixing the main agent i and the curing agent ii, gas-charging an inert gas at a pressure in the range of 0.05MPa to 0.2MPa to the main agent i and/or the curing agent ii, wherein the inert gas is carbon dioxide,
the viscosity of the main agent i at 50 ℃ when the gas loading is performed is in the range of 200 mPas to 20,000 mPas.
2. The method for producing a polyurethane foam sheet according to claim 1,
the gas loading is carried out only on the main agent i.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2016100413 | 2016-05-19 | ||
| JP2016-100413 | 2016-05-19 | ||
| PCT/JP2017/014037 WO2017199608A1 (en) | 2016-05-19 | 2017-04-04 | Method for producing polyurethane foam sheet |
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| Publication Number | Publication Date |
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| CN109153761A CN109153761A (en) | 2019-01-04 |
| CN109153761B true CN109153761B (en) | 2021-01-08 |
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| CN201780030576.4A Active CN109153761B (en) | 2016-05-19 | 2017-04-04 | Process for producing polyurethane foam sheet |
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| JP (1) | JP6281666B1 (en) |
| CN (1) | CN109153761B (en) |
| TW (1) | TWI689537B (en) |
| WO (1) | WO2017199608A1 (en) |
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| CN110627982A (en) * | 2019-10-22 | 2019-12-31 | 贵州华云汽车饰件制造有限公司 | Polyurethane foaming forming process for automotive interior parts |
| JP2022060014A (en) * | 2020-10-02 | 2022-04-14 | 積水化学工業株式会社 | Mixing system |
| TR202022114A1 (en) | 2020-12-29 | 2022-07-21 | Pimsa Otomotiv Anonim Sirketi | A POLYURETHANE FOAM COMPOSITION AND METHOD FOR ITS SYNTHESIS |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1315973A (en) * | 1998-07-09 | 2001-10-03 | 拜尔安特卫普有限公司 | permanent gas blown microcellular polyurethane elastomers |
| CN1500128A (en) * | 2001-04-01 | 2004-05-26 | Rigid polyurethane foams | |
| JP2006124579A (en) * | 2004-10-29 | 2006-05-18 | Inoac Corp | Polyurethane foam and method for producing the same |
| JP2007231256A (en) * | 2006-01-31 | 2007-09-13 | Sanyo Chem Ind Ltd | Method for producing rigid polyurethane foam for cutting working |
| JP2014024880A (en) * | 2012-07-24 | 2014-02-06 | Dic Corp | Uv-curable urethane acrylate resin composition, thin film molded article, optical film, and production method of thin film molded article |
| CN104662072A (en) * | 2012-04-26 | 2015-05-27 | 拜尔材料科学有限公司 | Viscoelastic polyurethane foams |
-
2017
- 2017-04-04 CN CN201780030576.4A patent/CN109153761B/en active Active
- 2017-04-04 WO PCT/JP2017/014037 patent/WO2017199608A1/en active Application Filing
- 2017-04-04 JP JP2017549837A patent/JP6281666B1/en active Active
- 2017-05-18 TW TW106116407A patent/TWI689537B/en active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1315973A (en) * | 1998-07-09 | 2001-10-03 | 拜尔安特卫普有限公司 | permanent gas blown microcellular polyurethane elastomers |
| CN1500128A (en) * | 2001-04-01 | 2004-05-26 | Rigid polyurethane foams | |
| JP2006124579A (en) * | 2004-10-29 | 2006-05-18 | Inoac Corp | Polyurethane foam and method for producing the same |
| JP2007231256A (en) * | 2006-01-31 | 2007-09-13 | Sanyo Chem Ind Ltd | Method for producing rigid polyurethane foam for cutting working |
| CN104662072A (en) * | 2012-04-26 | 2015-05-27 | 拜尔材料科学有限公司 | Viscoelastic polyurethane foams |
| JP2014024880A (en) * | 2012-07-24 | 2014-02-06 | Dic Corp | Uv-curable urethane acrylate resin composition, thin film molded article, optical film, and production method of thin film molded article |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2017199608A1 (en) | 2017-11-23 |
| TW201809093A (en) | 2018-03-16 |
| TWI689537B (en) | 2020-04-01 |
| CN109153761A (en) | 2019-01-04 |
| JP6281666B1 (en) | 2018-02-21 |
| JPWO2017199608A1 (en) | 2018-05-31 |
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