WO1990008804A1 - Process for preparing integral skin foam - Google Patents

Process for preparing integral skin foam Download PDF

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Publication number
WO1990008804A1
WO1990008804A1 PCT/JP1990/000086 JP9000086W WO9008804A1 WO 1990008804 A1 WO1990008804 A1 WO 1990008804A1 JP 9000086 W JP9000086 W JP 9000086W WO 9008804 A1 WO9008804 A1 WO 9008804A1
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WO
WIPO (PCT)
Prior art keywords
weight
component
polyol
isocyanate
integral skin
Prior art date
Application number
PCT/JP1990/000086
Other languages
French (fr)
Inventor
Hiromichi Hotta
Kazuo Mizumura
Katsuji Kuribayashi
Original Assignee
Dow Mitsubishi Kasei Limited
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
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Priority to KR1019900702127A priority Critical patent/KR910700302A/en
Publication of WO1990008804A1 publication Critical patent/WO1990008804A1/en

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/34—Chemical features in the manufacture of articles consisting of a foamed macromolecular core and a macromolecular surface layer having a higher density than the core
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
    • C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
    • C08J9/143—Halogen containing compounds
    • C08J9/144—Halogen containing compounds containing carbon, halogen and hydrogen only
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
    • C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
    • C08J9/143—Halogen containing compounds
    • C08J9/147—Halogen containing compounds containing carbon and halogen atoms only
    • 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
    • C08G2110/0033—Foam properties having integral skins
    • 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
    • C08G2110/0041—Foam properties having specified density
    • C08G2110/0066—≥ 150kg/m3
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes

Definitions

  • the present invention pertains to a process for preparing an integral skin foam. More specifically, it pertains to a process for preparing an integral skin foam having an excellent abrasion-resistance by using specific isocyanate starting materials.
  • Integral skin foam is widely used as interior parts of automobiles, and for furniture, etc. and due to its excellent feeling and high-quality appearance, and it is expected to become widely used for steering wheels and shift knobs, among other interior parts of automobiles.
  • the starting isocyanate used mainly for the production of an integral skin foam is 4,4'-diphenyl methane diisocyanate expressed by the following
  • the object of the present invention is to provide a process for preparing an integral skin foam, characterised by using a mixture of polydiphenylmethane diisocyanates expressed by the following general formula, in which the content of a component expressed by n - 0 is 53 - 85 wt.%, as an isocyanate component in relation to the preparation of an integral skin foam having an average density of 0.3 - 0.9 g/cm by blow-reacting starting materials comprising mainly an isocyanste and a polyol in the presence of 3 - 20 wt.% of a freon-based blowing agent with respect to the total weight of the starting materials, in a tightly closed mold maintained
  • n is an integer of 0 - 4.
  • a mixture of polydiphenyl methane diisocyanate used as an isocyanate component in the present invention can be obtained by using both pure MDI and crude MDI manufactured by distillation-separation, and mixing an appropriate amount of pure MDI with crude MDI.
  • the starting material used is a mixture of polydiphenyl methane diisocyanate expressed by the following general formula containing 55 - 85 wt.% of a component expressed by n - 0.
  • composition of a components expressed by n - 1, 2, 3 and 4 is normally 35 - 65 wt.% of a component expressed by n - 1, 5 - 30 wt.% of a component expressed by n - 2, 1 - 20 wt.% of a component expressed by n - 3, and 10 - 40 wt.% of a component expressed by n - 4 with respect to the total amount of these components.
  • n is an integer of 0 - 4.
  • the polyols used in the present invention include polyether polyols obtained by adding ethylene oxide and propylene oxide to water, ethylene glycol, propylene glycol, glycorol, trimethylol propane, and pentaerythritol as a starting material, and polymer polyols obtained by gr ft-polymerizing styrene and acrylonitrile to polyether polyols.
  • the molecular weight of these polyols is normally in a range of 3,000 - 8,000.
  • the equivalent ratio of NCO/OH is selected from a range of 0.95 - 1.1.
  • freon-based blowing agents used in the present invention include volatile liquids such as trichloro onofluoromethane, monochlorodifluoromethane, and dichlorodifluoromathane, and can be used alone or as a mixture of more thereof.
  • the amount used is in the range of 3 - 20 wt.% with respect to the total weight of the starting materials.
  • the blowing pressure When the amount is less than 3 wt.%, the blowing pressure is not be increased, and it is difficult to form a skin layer, and when it exceeds 20 wt.%, the blowing pressure exceeds the cell strength, and as a result, connections are formed before the formation of skin layer and it becomes difficult to form the skin layer, whereby the abrasion-resistance is lowered.
  • the catalysts used are those commonly used and include amine-based and tin-based catalysts, which can be used alone or as a mixture thereof.
  • the amine-based catalysts include triethylene diamine, N-methyl orpholine, tetramethyl and ethylene diamine and the tin-based catalysts include stannous octoate, stannous laurate, and dibutyl tin dilaurate.
  • the amount used is normally 0.01 - 2.0 wt.% with respect to the polyol.
  • the crosslinking agents include ethylene glycol, diethylene glycol, 1,4-butanediol, and 1,2-butanediol, and the amount used is 3 - 20 wt.% with respect to the polyol.
  • a silicone foam-controlling agent and a toner aging-inhibitor can be used.
  • iron and aluminum which have a high coefficient of thermal conductivity, are used as a material of the mold.
  • a resin mold having a low coefficient of thermal conductivity is used, since the urethane temperature on the mold surface is not lowered, it becomes difficult to form a skin layer and the abrasion-resistance is lowered.
  • the mold temperature must be in a range of 40
  • integral skin foam is in a range of 0.3 - 0.9 g/cm .
  • an integral skin foam manufactured by the method of the present invention has an excellent abrasion-resistance, it is most suitable for furniture and the interior parts of automobile, particularly the steering wheel and shift knob which require a high abrasion-resistance.
  • Example 1 is explained specifically as follows using actual examples and comparison examples. It is understood, however, that the present invention is not limited to the embodiment described with respect to the following actual examples as long as the object of the present invention is obtained.
  • Example 1 is explained specifically as follows using actual examples and comparison examples. It is understood, however, that the present invention is not limited to the embodiment described with respect to the following actual examples as long as the object of the present invention is obtained.
  • n is integer of 0 - 4, 100 wt.% tri-functional polyether polyol with a molecular weight of 6,000 as a polyol, 10 wt.% 1,4-butanediol as a crosslinking agent, 10 wt.% freon as a blowing agent, 0.6 wt.% triethylene diamine as a catalyst, 0.01 wt.% dibutyl tin dilaurate, and 0.5 wt.% of a silicone foam-controlling agent, was injected at an isocyanate index of 1.15, using a high-pressure blowing machine, into an Al tightly closed mold with the dimensions of 200 X 800 x 5 mm (at a mold temperature of 50°C x 5°C), while aiming at a total
  • a mixture of polydiphenyl methane diisocyanate, in which the content of the component expressed by n 0 in the aforementioned general formula is 70 wt.%, as an isocyanate, and the same polyol component mixture as in Example 1 were molded under the same conditions as in Example 1.
  • the mixture of polydiphenyl methane diisocyanate, in which the content of the component expressed by n - 0 in the aforementioned general formula is 90 wt.%, as an isocyanate, and the same polyol component mixture as in Example 1 were molded under the same molding conditions as in Example 1.
  • the amount of abrasion was evaluated at 5,000 rotations.
  • an integral skin foam prepared by the present invention has an excellent abrasion-resistance, and thus the abrasion-resistance of steering wheels in particular can be greatly improved.

Abstract

A process for preparing an integral skin foam having an average density of 0.3-0.9 g/cm3 by blow-reacting starting materials mainly comprising an isocyanate and a polyol in the presence of 3-20 % by weight, based on the total weight of the starting materials, of a freon-based blowing agent in a tightly closed mold maintained at 40-70°C, wherein a mixture of polydiphenylmethane diisocyanates represented by general formula (I) (in which n is an integer of 0-4), which contains the polydiphenylmethane diisocyanate of the general formula in which n is 0 in an amount of 55-85 % by weight, is used as the isocyanate.

Description

DESCRIPTION
TITLE OF THE INVENTION
Process for Preparing Integral Skin Foam TECHNICAL FIELD
The present invention pertains to a process for preparing an integral skin foam. More specifically, it pertains to a process for preparing an integral skin foam having an excellent abrasion-resistance by using specific isocyanate starting materials. Integral skin foam is widely used as interior parts of automobiles, and for furniture, etc. and due to its excellent feeling and high-quality appearance, and it is expected to become widely used for steering wheels and shift knobs, among other interior parts of automobiles. BACKGROUND ART The starting isocyanate used mainly for the production of an integral skin foam is 4,4'-diphenyl methane diisocyanate expressed by the following
Figure imgf000003_0001
is used, however, although the resulting integral skin foam has no problems with regard to moldability, a problem arises of a poor abrasion-resistance. Since steering wheels and shift knobs in particular require a higer abrasion-resistance than other interior parts of automobiles, it is necessary to further improve the abrasion-resistance of integral skin foam for such applications. DISCLOSURE OF THE INVENTION
The object of the present invention is to provide a process for preparing an integral skin foam, characterised by using a mixture of polydiphenylmethane diisocyanates expressed by the following general formula, in which the content of a component expressed by n - 0 is 53 - 85 wt.%, as an isocyanate component in relation to the preparation of an integral skin foam having an average density of 0.3 - 0.9 g/cm by blow-reacting starting materials comprising mainly an isocyanste and a polyol in the presence of 3 - 20 wt.% of a freon-based blowing agent with respect to the total weight of the starting materials, in a tightly closed mold maintained
Figure imgf000004_0001
in which n is an integer of 0 - 4.
BEST MODE OF CARRYING OUT THE INVENTION The present invention is explained in detail below. A mixture of polydiphenyl methane diisocyanate used as an isocyanate component in the present invention can be obtained by using both pure MDI and crude MDI manufactured by distillation-separation, and mixing an appropriate amount of pure MDI with crude MDI. In the present invention, the starting material used is a mixture of polydiphenyl methane diisocyanate expressed by the following general formula containing 55 - 85 wt.% of a component expressed by n - 0. The composition of a components expressed by n - 1, 2, 3 and 4 is normally 35 - 65 wt.% of a component expressed by n - 1, 5 - 30 wt.% of a component expressed by n - 2, 1 - 20 wt.% of a component expressed by n - 3, and 10 - 40 wt.% of a component expressed by n - 4 with respect to the total amount of these components.
Figure imgf000004_0002
in which n is an integer of 0 - 4.
When the content of the component expressed by n - 0 in polydiphenyl methane diisocyanate mixture is in the above specific range, an integral skin foam with an improved abrasion-resistance can be obtained. When the content of the component expressed by n = 0 is less than 55 wt.%, the skin layer is too soft and the abrasion-resistance is lowered. Conversely, when it exceeds 85 wt.%, the skin layer becomes too hard, and the abrasion-resistance is again lowered.
The polyols used in the present invention include polyether polyols obtained by adding ethylene oxide and propylene oxide to water, ethylene glycol, propylene glycol, glycorol, trimethylol propane, and pentaerythritol as a starting material, and polymer polyols obtained by gr ft-polymerizing styrene and acrylonitrile to polyether polyols. The molecular weight of these polyols is normally in a range of 3,000 - 8,000.
The equivalent ratio of NCO/OH is selected from a range of 0.95 - 1.1.
The freon-based blowing agents used in the present invention include volatile liquids such as trichloro onofluoromethane, monochlorodifluoromethane, and dichlorodifluoromathane, and can be used alone or as a mixture of more thereof. The amount used is in the range of 3 - 20 wt.% with respect to the total weight of the starting materials. When the amount is less than 3 wt.%, the blowing pressure is not be increased, and it is difficult to form a skin layer, and when it exceeds 20 wt.%, the blowing pressure exceeds the cell strength, and as a result, connections are formed before the formation of skin layer and it becomes difficult to form the skin layer, whereby the abrasion-resistance is lowered.
The catalysts used are those commonly used and include amine-based and tin-based catalysts, which can be used alone or as a mixture thereof. The amine-based catalysts include triethylene diamine, N-methyl orpholine, tetramethyl and ethylene diamine and the tin-based catalysts include stannous octoate, stannous laurate, and dibutyl tin dilaurate. The amount used is normally 0.01 - 2.0 wt.% with respect to the polyol. The crosslinking agents include ethylene glycol, diethylene glycol, 1,4-butanediol, and 1,2-butanediol, and the amount used is 3 - 20 wt.% with respect to the polyol. In addition, a silicone foam-controlling agent and a toner aging-inhibitor can be used.
When an integral skin foam is to be manufactured according to the present invention, a tightly closed mold is used, since when an open mold is used, the blowing pressure is not increased in a mold and it is difficult to form the skin layer.
Preferably iron and aluminum, which have a high coefficient of thermal conductivity, are used as a material of the mold. When a resin mold having a low coefficient of thermal conductivity is used, since the urethane temperature on the mold surface is not lowered, it becomes difficult to form a skin layer and the abrasion-resistance is lowered.
The mold temperature must be in a range of 40
- 70°C. When the mold temperature is lower than 40°C, the products become too hard, resulting in a loss of feeling, and when the mold temperature exceeds 70°C, the reaction rate becomes too fast, resulting in poor flow characteristics and difficulty in forming the skin layer.
It is necessary to control the aforementioned blow-molding conditions so that the total density of the
2 integral skin foam is in a range of 0.3 - 0.9 g/cm .
3 When the total density is less than 0.3 g/cm , it is difficult to form a skin layer, and when it
3 exceeds 0.9 g/cm , the difference between the skin layer and the core layer becomes indefinite, and the products do not have the appearance of an integral skin foam. Since an integral skin foam manufactured by the method of the present invention has an excellent abrasion-resistance, it is most suitable for furniture and the interior parts of automobile, particularly the steering wheel and shift knob which require a high abrasion-resistance.
The present invention is explained specifically as follows using actual examples and comparison examples. It is understood, however, that the present invention is not limited to the embodiment described with respect to the following actual examples as long as the object of the present invention is obtained. Example 1
A mixture of a polydiphenyl methane diisocyanate expressed by the following general formula, in which the content of a component expressed by n = 0 is 55 wt.% and the remainder comprises components expressed by n = 4, as an isocyanate component,
Figure imgf000007_0001
in which n is integer of 0 - 4, 100 wt.% tri-functional polyether polyol with a molecular weight of 6,000 as a polyol, 10 wt.% 1,4-butanediol as a crosslinking agent, 10 wt.% freon as a blowing agent, 0.6 wt.% triethylene diamine as a catalyst, 0.01 wt.% dibutyl tin dilaurate, and 0.5 wt.% of a silicone foam-controlling agent, was injected at an isocyanate index of 1.15, using a high-pressure blowing machine, into an Al tightly closed mold with the dimensions of 200 X 800 x 5 mm (at a mold temperature of 50°C x 5°C), while aiming at a total
3 density of 0.7 g/cm , to manufacture an integral skin foam. After molding, a sample was left to stand at 23°C for 24 hours, and then was evaluated in terms of an amount of abrasion measured by using a taper-type abrasion tester with an abrasion ring of H-10 and the load of 500 g at 5,000 rpm. The results are shown in Table 1.
Example 2
A mixture of polydiphenyl methane diisocyanate, in which the content of the component expressed by n = 0 in the aforementioned general formula is 70 wt.%, as an isocyanate, and the same polyol component mixture as in Example 1 were molded under the same conditions as in Example 1. The amount of abrasion was evaluated at 5,000 rotations.
The results are given in Table 1.
Comparison Example 1
The mixture of polydiphenyl methane diisocyanate, in which the content of the component expressed by n - 0 in the aforementioned general formula is 90 wt.%, as an isocyanate, and the same polyol component mixture as in Example 1 were molded under the same molding conditions as in Example 1. The amount of abrasion was evaluated at 5,000 rotations.
The results are given in Table. 1.
Table 1
Ratio of Component Total Density Amount of wit n - 0 (wt.Z) (g/cm ) Abrasion ( g)
Example 1 55 0.70 65
Example 2 70 0.70 50
Comparison Example 1 90 0.71 200
INDUSTRIAL APPLICABILITY
As described in detail above, an integral skin foam prepared by the present invention has an excellent abrasion-resistance, and thus the abrasion-resistance of steering wheels in particular can be greatly improved.

Claims

1. A process for preparing an integral skin foam
3 of an average density of 0.3 - 0.9 g/cm by blow-reacting staring materials mainly comprising an isocyanate and a polyol in the presence of 3 - 20% by weight, based on the total weight of the starting materials, of a freon-based blowing agent in a tightly closed mold maintained at 40
- 70°C, wherein a mixture of polydiphenylmethane diisocyanates represented by the following general formula,
Figure imgf000009_0001
in which n is an integer of 0 - 4, which contains the polydiphenylmethane diisocyanate of the general formula in which n is 0 in an amount of 55 - 85% by weight, is used as the isocyanate.
2. A process as claimed in claim 1, wherein the mixture of polydiphenylmethane diisocyanates contains 35
- 65% by weight of the component in which n is 1, 5 - 30% by weight of the component in which n is 2, 1 - 20% by weight of the component in which n is 3, 10 - 40% by weight of the component in which n is 4.
3. A process as claimed in claim 1, wherein the polyol is selected from polyether polyols and polymer polyols obtained by graft-polymerizing styrene and acrylonitrile to the polyether polyols.
4. A process as claimed in claim 3, wherein the polyol has a molecular weight of 3,000 - 8,000.
5. A process as claimed in claim 1, wherein the equivalent ratio of NCO/OH is 0.95 - 1.1.
6. A process as claimed in claim 1, wherein the freon-based blowing agent is selected from trichloro- monofluoromethane, monochlorodifluoromethane and dichlorodifluoromethane.
PCT/JP1990/000086 1989-01-26 1990-01-25 Process for preparing integral skin foam WO1990008804A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1019900702127A KR910700302A (en) 1989-01-26 1990-01-25 Method for producing skin layer foam

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP1/17053 1989-01-26
JP1017053A JPH02196816A (en) 1989-01-26 1989-01-26 Production of integral skin foam

Publications (1)

Publication Number Publication Date
WO1990008804A1 true WO1990008804A1 (en) 1990-08-09

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KR (1) KR910700302A (en)
AR (1) AR244736A1 (en)
AU (1) AU4963590A (en)
WO (1) WO1990008804A1 (en)

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CN107365409A (en) * 2016-05-12 2017-11-21 上海飞利环球汽车零部件有限公司 A kind of engine bonnet and preparation method thereof

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1548164A (en) * 1966-12-27 1968-11-29
GB1324501A (en) * 1969-07-31 1973-07-25 Ici Ltd Moulding process for polyurethane rigid foam
GB1326901A (en) * 1969-11-21 1973-08-15 Ici Ltd Expanded polyurethanes
US3836487A (en) * 1968-09-23 1974-09-17 Goodyear Tire & Rubber High impact rigid self-skinned polyurethane foam and method
EP0294110A1 (en) * 1987-05-26 1988-12-07 Imperial Chemical Industries Plc Process for the preparation of rigid foams.
EP0297519A1 (en) * 1987-07-01 1989-01-04 BASF Corporation Process for the preparation of integral skin polyurethane steering wheels
EP0114970B1 (en) * 1983-01-26 1990-12-05 The Dow Chemical Company Improved process for the preparation of polymethylene polyphenyl polyisocyanates

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1548164A (en) * 1966-12-27 1968-11-29
US3836487A (en) * 1968-09-23 1974-09-17 Goodyear Tire & Rubber High impact rigid self-skinned polyurethane foam and method
GB1324501A (en) * 1969-07-31 1973-07-25 Ici Ltd Moulding process for polyurethane rigid foam
GB1326901A (en) * 1969-11-21 1973-08-15 Ici Ltd Expanded polyurethanes
EP0114970B1 (en) * 1983-01-26 1990-12-05 The Dow Chemical Company Improved process for the preparation of polymethylene polyphenyl polyisocyanates
EP0294110A1 (en) * 1987-05-26 1988-12-07 Imperial Chemical Industries Plc Process for the preparation of rigid foams.
EP0297519A1 (en) * 1987-07-01 1989-01-04 BASF Corporation Process for the preparation of integral skin polyurethane steering wheels

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AR244736A1 (en) 1993-11-30
AU4963590A (en) 1990-08-24
JPH02196816A (en) 1990-08-03
KR910700302A (en) 1991-03-14

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