CA2107438C - Process and apparatus for the manufacture of a molded part - Google Patents
Process and apparatus for the manufacture of a molded partInfo
- Publication number
- CA2107438C CA2107438C CA 2107438 CA2107438A CA2107438C CA 2107438 C CA2107438 C CA 2107438C CA 2107438 CA2107438 CA 2107438 CA 2107438 A CA2107438 A CA 2107438A CA 2107438 C CA2107438 C CA 2107438C
- Authority
- CA
- Canada
- Prior art keywords
- components
- mixing head
- temperature
- component
- mixing
- 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.)
- Expired - Fee Related
Links
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
- B29B7/00—Mixing; Kneading
- B29B7/80—Component parts, details or accessories; Auxiliary operations
- B29B7/82—Heating or cooling
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C67/00—Shaping techniques not covered by groups B29C39/00 - B29C65/00, B29C70/00 or B29C73/00
- B29C67/24—Shaping techniques not covered by groups B29C39/00 - B29C65/00, B29C70/00 or B29C73/00 characterised by the choice of material
- B29C67/246—Moulding high reactive monomers or prepolymers, e.g. by reaction injection moulding [RIM], liquid injection moulding [LIM]
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2075/00—Use of PU, i.e. polyureas or polyurethanes or derivatives thereof, as moulding material
Landscapes
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
- Casting Or Compression Moulding Of Plastics Or The Like (AREA)
Abstract
In a process for the manufacture of a molded part from a non-porous, elastic polyurethane, the starting components are individually isothermally transported from storage tanks through closed loop conduits and pumps into a mixing head. Mixing of the components is carried out in the mixing head at a pressure of at least 150 bar and the resulting mixture is then expelled from the mixing head and into a mold. This process obviates the annealing step required in conventional polyurethane casting processes for solidification of the molded part manufactured therewith, Apparatus for the carrying out of the process are also disclosed.
Description
21~3~
PROCESS AND APPARATUS FOR THE MANUFACTURE ~F A MOLDED PART
The invention relates to the manufacture of molded parts of non-porous, elastic polyurethane which are made by a casting process.
In conventional processes for the manufacture of such molded part~, a pre-polymer or adduct is first manufactured which is the result of a reaction between diisocyanate and polyol. This pre-polymer or adduct is then transported to a mixing head through conduits and exactly metering gear pumps. Cros~-linking or chain extending agents and, if requlred, catalysts are also transported to the mixing head by metering gear pumps. The mixing ratio between pre-polymer or adduct and cross-linking or chain extending agent~ i~ thereby 100:1 to 100:10. Usually, the mixing pressure in the conduits does not exceed the output pressure of the gear pumps and, thus, is sub~tantially below 20 bar and must be mechanically assisted by way of spike or worm mixers. The mixture of pre-polymer and cross-linking or chain-extending agents is continuously discharged from the mixing head lnto open molds which are passed thereunder.
The diisocyanates used are especially toluylenediisocyanate 1,5-naphthylenedii~ocyanate or 4,4'-diphenyl-methanediisocyanate.
Conventionally used polyols are, for example, polycaprolactone diol, polyester diol or polyether diol respectively having a molecular weight of 1,000 to 5,000 or polycarbonate diol having a molecular weight of 600 to 2,000. The molded part~ which are manufactured with this convent~onal process and in the convent~onal apparatus must b0 baked in heated tools for 10 to 40 minutes. This is usually, followed by an annealing process of one or more days.
One prior art proces~ is described in Oertel, Polyurethane Handbook, Carl-Hanser-Verlag, Miinrhen (1985), page 378, example 2.
The conventional process has the following disadvantage3. The low achievable output pre~qure of the transporting pumps reQults in a long casting time and requires the use of an open mold, which limitq the range of poss~ble geometric shapes of the molded part. Furthermore, the reaction time is between 1 and 40 minutes at about 130~C and the subsequent annealing, which depending on the wall thickness of the molded part may last several days, 910ws the process and increases its c03t.
2107~3~
It is now an ob~ect of the present invention to substantially overcome or reduce these problems in the manufacture of molded parts of non-porous, elastlc polyurethane. In particular, it is an ob~ect of the present invention to reduce the casting time and the time required for S completion of the reaction of the mixed ingredients to a fini3hed molded part.
This ob~ect is achieved according to the present invention by ~eparately heating the diisocyanate and polyol components prior to mixing to a temperature above their respective melting temperature but below their respective decomposition temperature, mixing the components under pressure in the mixlng head and transferring ~he mixture into a mold.
Preferably, at least two separate component flows are generated which flow from at least two heated storage containers for the ~tarting materials to be processed, the diisocyanate and the polyol components through closed-loop conduits and pumps and into the m~xing head. In the storage containers and the separate flow circuits, these component flows are respectively malntained at a constant temperature which lies above the melting temperature and below the decomposition temperature of the respective component. These temperatureQ are selected so that the viscosity of each component flow is below 900 Pa s as measured by DIN
51562. The component flows are ~oined in a high pressure mixing head which forms part of the isothermal temperature circuit of the diisocyanate and, thu~, is heated to ~he temperature of the diisocyanate component. The mixing head, the pumps and the circulation conduits are constructed 90 that a mixing of the starting products st a pressure of at least 150 bar i~ achieved.
Accordingly, the invention provides a process for the manufacture of a molded part from a non-porous, elastic poly~rethane, wherein a diisocyanate c; ~nt solid at room temperature and a polyol component which may also be solid at room temperature are mixed in the liquid condition, transferred ~nto a hollow mold and solidified. The diisocyanate and polyol components are separately heated to a temperature which is above the melting temperature but below the decomposition temperature of the respective component and provides a component 35 viscosity below 900 Pa s, measured according to DIN 51562. The heated components are then mixed with each other in a high pressure mixing head 2107~3~
at a pressure of at least 150 bar, expelled from the mixing head and transferred into the molding tool. The temperature of the heated ~omponents is maintained constant during the process until entry into the mixing head which iY heated to the temperature of the diisocyanate. The mixed components which are connected by a chemical reaction are no longer sub~ect to this isothermal reaction control and the high pressure after e~ection from the high pressure mixing head.
High pressure mixing heads are known, but not for use in a process of this type, 3ince an isothermal temperature control of the type disclosed herein could not be guaranteed, since in conventional apparatus using high pressure mixing head~, portions of the components, and especially of the diiqocyanate component which is solid at room temperature, would come in contact with solidified, cooled down material at some point in the conduits which was not heated and would immediately clog the conduits. Therefore, the mixing ratio required for the achievement of a reproducible reaction could not be maintained with sufficient accuracy which iq also the reason why only low pressure arrangements were used. Consequently, the operation of a high pressure arrangement as in the present invention was previously not possible.
Only the combination of the respectively isothermal component transport all the way from the storage containers through the conduitA
and pumps and, in case of the diisocyanate, in the mixing head, when combined with the component control under pressure allows the operation of a process in accordance with the invention. Maintaining the pressure in the separate component circuits up to the mixing head at at least 150 bar provides for an optimal mixing of the st~rting component~ within only a few seconds even at a feed rate of the component flows of up to 2 1/8 and promotes the chemical reaction of the componen~s to the end product in such a way that in many cases, especially ~ith component parts for couplings, the annealing required in conventional processes is obviated.
This results in production time savings of several dayq, which i8 a further important advantage of the present invention.
The individual components of an apparatus in accordance with the invention are known. However, it is important that the apparatus include means for maintaining all parts in contact with the respective components at a constant temperature and that the apparatus be constructed to 2~07~g withstand high pressures. The measures requ~red to achieve ~his do not pose any technical problems:
The isothermal control can be guaranteed wlth conventional heating arrangements surrounding the conduits for the respective components, for example in~rared radiators, heating bands or liguid heating media. The pressure required for a process in accordance with the invention is preferably achieved by pistons which compress the components. The sealing of the conduits, the pumps and the mixing head also does not po~e a problem, since known hydraulic component~ can be u~ed.
Accordingly, the invention further provides apparatus for carry~ng out the process described above which includes a~ least two ~torage containers for the components to be used, which containers are individually connected to a mixing head by closed loop conduits including pumps for liquefaction of the components. All part~ of the apparatus which are contacted by the components and especially the closed loop conduits are provlded with heating arrangements for liquefaction of the components. The heating arrangements further guarantee an isothermal temperature control of the respective component and that the mixing head. The pumps and the closed loop conduits are constructed to withstand a pressure of at least 150 bar for the mixing of the components.
The following example is used to further describe the invention:
Two ce ponpnts were maintained in constant movement in ~eparate ~torage tanks heated to the respectlve component circulation temperature in order to prevent dc l~1ne. Component A consisted of:
di-functional epsilon-polycaprolactonediol 9 Molecular weight 2,000 2,000 g Diethyltoluoldiamine 445 g Diaza-bicyclooctane (2,2,2) 2,44 g Component B was:
4,4'-diphenylmethanedlisocyanate 901.25 g The circuit for component A including the storage container, pumps and the closed loop conduit was isothermally heated to 100~C by way of an oil mantle. Component B, the diisocyanate, was heated in $he same way ~o 55~C while being transported from its storage container through the pumps and the closed loop conduit and into the mixing head. The whole heated system which held the starting materials was sub~ected to a pressure of 2~07~3g about 200 bar by way of an in~ec~ion cylinder. Thi9 pressure was the same throughout the apparatus even in the mi~ing head.
The molding tool was filled for the manufacture of a test plate with different wall thick~lesses up to 6 mm by opening valves for the respective components for an in~ection interval of 1.14 second~. These valves were also appropriately heated. The components were mixed in the high pressure mixing head in cross flow at high speed and subsequently after exiting the mixing head directly filled the cavities of the molding tool. The mixed material recelved in the tool was thereafter exposed to a pres~ure of about S0 bar by way of an integrated piston at a tool temperature of 70~C. This process step lasted for 10 seconds. The molded part was thereby consolidated. The finished molded part, the test plate, had a weight of 114 g. Corresponding molded parts can be produced with a cycle time of 15 to 30 seconds. The annealing 3tep required in conventional proces~e3 can be omitted from the present process without a re~ulting quality loss.
Changes and modifications in the ~pecifically described embodiments can be carried out without departing from the scope of the invention which is intended to be limited only by the scope of the appended claims.
PROCESS AND APPARATUS FOR THE MANUFACTURE ~F A MOLDED PART
The invention relates to the manufacture of molded parts of non-porous, elastic polyurethane which are made by a casting process.
In conventional processes for the manufacture of such molded part~, a pre-polymer or adduct is first manufactured which is the result of a reaction between diisocyanate and polyol. This pre-polymer or adduct is then transported to a mixing head through conduits and exactly metering gear pumps. Cros~-linking or chain extending agents and, if requlred, catalysts are also transported to the mixing head by metering gear pumps. The mixing ratio between pre-polymer or adduct and cross-linking or chain extending agent~ i~ thereby 100:1 to 100:10. Usually, the mixing pressure in the conduits does not exceed the output pressure of the gear pumps and, thus, is sub~tantially below 20 bar and must be mechanically assisted by way of spike or worm mixers. The mixture of pre-polymer and cross-linking or chain-extending agents is continuously discharged from the mixing head lnto open molds which are passed thereunder.
The diisocyanates used are especially toluylenediisocyanate 1,5-naphthylenedii~ocyanate or 4,4'-diphenyl-methanediisocyanate.
Conventionally used polyols are, for example, polycaprolactone diol, polyester diol or polyether diol respectively having a molecular weight of 1,000 to 5,000 or polycarbonate diol having a molecular weight of 600 to 2,000. The molded part~ which are manufactured with this convent~onal process and in the convent~onal apparatus must b0 baked in heated tools for 10 to 40 minutes. This is usually, followed by an annealing process of one or more days.
One prior art proces~ is described in Oertel, Polyurethane Handbook, Carl-Hanser-Verlag, Miinrhen (1985), page 378, example 2.
The conventional process has the following disadvantage3. The low achievable output pre~qure of the transporting pumps reQults in a long casting time and requires the use of an open mold, which limitq the range of poss~ble geometric shapes of the molded part. Furthermore, the reaction time is between 1 and 40 minutes at about 130~C and the subsequent annealing, which depending on the wall thickness of the molded part may last several days, 910ws the process and increases its c03t.
2107~3~
It is now an ob~ect of the present invention to substantially overcome or reduce these problems in the manufacture of molded parts of non-porous, elastlc polyurethane. In particular, it is an ob~ect of the present invention to reduce the casting time and the time required for S completion of the reaction of the mixed ingredients to a fini3hed molded part.
This ob~ect is achieved according to the present invention by ~eparately heating the diisocyanate and polyol components prior to mixing to a temperature above their respective melting temperature but below their respective decomposition temperature, mixing the components under pressure in the mixlng head and transferring ~he mixture into a mold.
Preferably, at least two separate component flows are generated which flow from at least two heated storage containers for the ~tarting materials to be processed, the diisocyanate and the polyol components through closed-loop conduits and pumps and into the m~xing head. In the storage containers and the separate flow circuits, these component flows are respectively malntained at a constant temperature which lies above the melting temperature and below the decomposition temperature of the respective component. These temperatureQ are selected so that the viscosity of each component flow is below 900 Pa s as measured by DIN
51562. The component flows are ~oined in a high pressure mixing head which forms part of the isothermal temperature circuit of the diisocyanate and, thu~, is heated to ~he temperature of the diisocyanate component. The mixing head, the pumps and the circulation conduits are constructed 90 that a mixing of the starting products st a pressure of at least 150 bar i~ achieved.
Accordingly, the invention provides a process for the manufacture of a molded part from a non-porous, elastic poly~rethane, wherein a diisocyanate c; ~nt solid at room temperature and a polyol component which may also be solid at room temperature are mixed in the liquid condition, transferred ~nto a hollow mold and solidified. The diisocyanate and polyol components are separately heated to a temperature which is above the melting temperature but below the decomposition temperature of the respective component and provides a component 35 viscosity below 900 Pa s, measured according to DIN 51562. The heated components are then mixed with each other in a high pressure mixing head 2107~3~
at a pressure of at least 150 bar, expelled from the mixing head and transferred into the molding tool. The temperature of the heated ~omponents is maintained constant during the process until entry into the mixing head which iY heated to the temperature of the diisocyanate. The mixed components which are connected by a chemical reaction are no longer sub~ect to this isothermal reaction control and the high pressure after e~ection from the high pressure mixing head.
High pressure mixing heads are known, but not for use in a process of this type, 3ince an isothermal temperature control of the type disclosed herein could not be guaranteed, since in conventional apparatus using high pressure mixing head~, portions of the components, and especially of the diiqocyanate component which is solid at room temperature, would come in contact with solidified, cooled down material at some point in the conduits which was not heated and would immediately clog the conduits. Therefore, the mixing ratio required for the achievement of a reproducible reaction could not be maintained with sufficient accuracy which iq also the reason why only low pressure arrangements were used. Consequently, the operation of a high pressure arrangement as in the present invention was previously not possible.
Only the combination of the respectively isothermal component transport all the way from the storage containers through the conduitA
and pumps and, in case of the diisocyanate, in the mixing head, when combined with the component control under pressure allows the operation of a process in accordance with the invention. Maintaining the pressure in the separate component circuits up to the mixing head at at least 150 bar provides for an optimal mixing of the st~rting component~ within only a few seconds even at a feed rate of the component flows of up to 2 1/8 and promotes the chemical reaction of the componen~s to the end product in such a way that in many cases, especially ~ith component parts for couplings, the annealing required in conventional processes is obviated.
This results in production time savings of several dayq, which i8 a further important advantage of the present invention.
The individual components of an apparatus in accordance with the invention are known. However, it is important that the apparatus include means for maintaining all parts in contact with the respective components at a constant temperature and that the apparatus be constructed to 2~07~g withstand high pressures. The measures requ~red to achieve ~his do not pose any technical problems:
The isothermal control can be guaranteed wlth conventional heating arrangements surrounding the conduits for the respective components, for example in~rared radiators, heating bands or liguid heating media. The pressure required for a process in accordance with the invention is preferably achieved by pistons which compress the components. The sealing of the conduits, the pumps and the mixing head also does not po~e a problem, since known hydraulic component~ can be u~ed.
Accordingly, the invention further provides apparatus for carry~ng out the process described above which includes a~ least two ~torage containers for the components to be used, which containers are individually connected to a mixing head by closed loop conduits including pumps for liquefaction of the components. All part~ of the apparatus which are contacted by the components and especially the closed loop conduits are provlded with heating arrangements for liquefaction of the components. The heating arrangements further guarantee an isothermal temperature control of the respective component and that the mixing head. The pumps and the closed loop conduits are constructed to withstand a pressure of at least 150 bar for the mixing of the components.
The following example is used to further describe the invention:
Two ce ponpnts were maintained in constant movement in ~eparate ~torage tanks heated to the respectlve component circulation temperature in order to prevent dc l~1ne. Component A consisted of:
di-functional epsilon-polycaprolactonediol 9 Molecular weight 2,000 2,000 g Diethyltoluoldiamine 445 g Diaza-bicyclooctane (2,2,2) 2,44 g Component B was:
4,4'-diphenylmethanedlisocyanate 901.25 g The circuit for component A including the storage container, pumps and the closed loop conduit was isothermally heated to 100~C by way of an oil mantle. Component B, the diisocyanate, was heated in $he same way ~o 55~C while being transported from its storage container through the pumps and the closed loop conduit and into the mixing head. The whole heated system which held the starting materials was sub~ected to a pressure of 2~07~3g about 200 bar by way of an in~ec~ion cylinder. Thi9 pressure was the same throughout the apparatus even in the mi~ing head.
The molding tool was filled for the manufacture of a test plate with different wall thick~lesses up to 6 mm by opening valves for the respective components for an in~ection interval of 1.14 second~. These valves were also appropriately heated. The components were mixed in the high pressure mixing head in cross flow at high speed and subsequently after exiting the mixing head directly filled the cavities of the molding tool. The mixed material recelved in the tool was thereafter exposed to a pres~ure of about S0 bar by way of an integrated piston at a tool temperature of 70~C. This process step lasted for 10 seconds. The molded part was thereby consolidated. The finished molded part, the test plate, had a weight of 114 g. Corresponding molded parts can be produced with a cycle time of 15 to 30 seconds. The annealing 3tep required in conventional proces~e3 can be omitted from the present process without a re~ulting quality loss.
Changes and modifications in the ~pecifically described embodiments can be carried out without departing from the scope of the invention which is intended to be limited only by the scope of the appended claims.
Claims (2)
1. Process for the manufacture of a molded part from a non-porous, elastic polyurethane, comprising the steps of separately heating a diisocyanate component which is solid at room temperature and a polyol component which may also be solid at room temperature to a temperature which is above the melting temperature and below the decomposition temperature of the respective component and provides for a viscosity below 900 Pa s of the respective components as measured according to DIN
51562, mixing the separately heated components with each other in a high pressure mixing head at a pressure of at least 150 bar, expelling the resulting mixture from the mixing head and transferring the mixture into a hollow molding tool, the heated components being maintained at a constant temperature throughout the process until entry into the mixing head which is heated to the temperature of the diisocyanate component.
51562, mixing the separately heated components with each other in a high pressure mixing head at a pressure of at least 150 bar, expelling the resulting mixture from the mixing head and transferring the mixture into a hollow molding tool, the heated components being maintained at a constant temperature throughout the process until entry into the mixing head which is heated to the temperature of the diisocyanate component.
2. Apparatus for carrying out the process of claim 1, comprising at least two storage containers for the components respectively used, the containers being individually connected to a mixing head by closed loop conduits including pumps, each closed loop conduit including a heating arrangement for liquefaction of the components, all parts of the apparatus which are in contact with at least one of the components being provided with a heating arrangement for maintaining the respectively engaged liquefied component at a constant temperature, and the mixing head, the pumps and the closed loop conduits being constructed to withstand a pressure of at least 150 bar for mixing of the components under pressure.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4232941.8-16 | 1992-10-01 | ||
| DE19924232941 DE4232941C2 (en) | 1992-10-01 | 1992-10-01 | Method and device for producing a molded part |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2107438A1 CA2107438A1 (en) | 1994-04-02 |
| CA2107438C true CA2107438C (en) | 1998-11-10 |
Family
ID=6469337
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2107438 Expired - Fee Related CA2107438C (en) | 1992-10-01 | 1993-09-30 | Process and apparatus for the manufacture of a molded part |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0590245A1 (en) |
| JP (1) | JPH06190825A (en) |
| CA (1) | CA2107438C (en) |
| DE (1) | DE4232941C2 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0879685B1 (en) * | 1997-05-22 | 2002-11-06 | Afros S.P.A. | Self-cleaning, mixing apparatus and method for the production of polyurethane mixtures |
| ATE523536T1 (en) | 2007-03-02 | 2011-09-15 | Basf Se | PRODUCTION OF HARD POLYURETHANE ELASTOMER MOLDED PARTS |
| TWI432306B (en) * | 2008-07-08 | 2014-04-01 | Gala Inc | Method and apparatus to achieve formulation and reactive polymerization utilizing a thermally and atmospherically controlled feeding system for thermoplastic materials |
| IT1392172B1 (en) * | 2008-12-03 | 2012-02-22 | Afros Spa | METHOD AND MIXING EQUIPMENT FOR HIGH PRESSURE, FOR LOADED POLYURETHANE RESINS |
| EP2952531A1 (en) | 2014-06-02 | 2015-12-09 | Basf Se | Elastic molded parts based on polyurethane |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2331241A1 (en) * | 1973-06-19 | 1975-01-09 | Demag Kunststofftech | METHOD AND DEVICE FOR MANUFACTURING MOLDED PARTS FROM PLASTICS MADE FROM SEVERAL COMPONENTS IN A CASTING FORM, IN WHICH THE COMPONENTS ARE MIXED WITH EACH OTHER BEFORE INTRODUCING INTO THE CASTING FORM |
| JPS5835467U (en) * | 1981-09-02 | 1983-03-08 | 三菱電機株式会社 | Vehicle electric motor idling device |
| US4430287A (en) * | 1982-07-21 | 1984-02-07 | The Upjohn Company | Reaction injection molding of nylon |
| JPS6011323A (en) * | 1983-07-01 | 1985-01-21 | Matsushita Electric Ind Co Ltd | Apparatus for reactive injection molding |
| JPS6027511A (en) * | 1983-07-19 | 1985-02-12 | ポリウレタン・テクノロジ−・オブ・アメリカ−マ−チン・スウイ−ツ・コンパニ−・インコ−ポレ−テツド | High-pressure collision mixer |
| JPS6241083A (en) * | 1985-08-19 | 1987-02-23 | Idemitsu Kosan Co Ltd | Optical memory material |
| US4726933A (en) * | 1985-10-08 | 1988-02-23 | Admiral Equipment Company | High pressure mixing head and reactive component injection valve |
| JPS62121017A (en) * | 1985-11-21 | 1987-06-02 | Mitsuboshi Belting Ltd | High-pressure casting machine |
| WO1988004225A1 (en) * | 1986-12-01 | 1988-06-16 | Hans Willi Meinz | Device for metering at least two flowable reaction components into a mixing chamber |
| JPS63283914A (en) * | 1987-05-18 | 1988-11-21 | Mazda Motor Corp | Mixing injection machine of reactive injection molding device |
| JPS648335U (en) * | 1987-07-01 | 1989-01-18 | ||
| JPH0629756Y2 (en) * | 1988-09-14 | 1994-08-10 | 株式会社精工舎 | Panel cover mounting structure |
| DE4211777A1 (en) * | 1991-07-04 | 1993-01-07 | Bayer Ag | METHOD FOR PRODUCING ELASTOMERIC POLYURETHANES, ESPECIALLY IN THE FORM OF SHOE SOLES |
-
1992
- 1992-10-01 DE DE19924232941 patent/DE4232941C2/en not_active Expired - Lifetime
-
1993
- 1993-07-02 EP EP93110571A patent/EP0590245A1/en not_active Withdrawn
- 1993-09-30 CA CA 2107438 patent/CA2107438C/en not_active Expired - Fee Related
- 1993-10-01 JP JP24683093A patent/JPH06190825A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE4232941C2 (en) | 1995-03-02 |
| JPH06190825A (en) | 1994-07-12 |
| DE4232941A1 (en) | 1994-04-07 |
| EP0590245A1 (en) | 1994-04-06 |
| CA2107438A1 (en) | 1994-04-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |