DK145300B - PROCEDURE FOR THE PREPARATION OF ETHYLENE CARBONATE OR PROPYLENE CARBONATE - Google Patents
PROCEDURE FOR THE PREPARATION OF ETHYLENE CARBONATE OR PROPYLENE CARBONATE Download PDFInfo
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- DK145300B DK145300B DK112576AA DK112576A DK145300B DK 145300 B DK145300 B DK 145300B DK 112576A A DK112576A A DK 112576AA DK 112576 A DK112576 A DK 112576A DK 145300 B DK145300 B DK 145300B
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- carbonate
- ethylene carbonate
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- ethylene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
- C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyesters Or Polycarbonates (AREA)
- Catalysts (AREA)
Description
(19) DANMARK (? i V*"^(19) DENMARK (? I V * "^
® (12) FREMLÆGGELSESSKRIFT du 145300 B® (12) PUBLICATION MANUAL du 145300 B
DIREKTORATET FOR PATENT- OG VAREMÆRKEVÆSENETDIRECTORATE OF THE PATENT AND TRADEMARKET SYSTEM
(21) Ansøgning nr. 1125/76 (51) IntCI.* C 07 D 317/36 (22) Indleveringsdag 16. mar. 1976 (24) Løbedag 16. mar. 1976 (41) Aim. tilgængelig 18. sep. 1976 (44) Fremlagt 25. okt. 1982 (86) International ansøgning nr. -(86) International indleveringsdag (85) Videreførelsesdag -(62) Stamansøgning nr. -(21) Application No. 1125/76 (51) IntCI. * C 07 D 317/36 (22) Filing Date 16 Mar 1976 (24) Race day 16 Mar 1976 (41) Aim. available Sep 18 1976 (44) Posted Oct 25 1982 (86) International application # - (86) International filing day (85) Continuation day - (62) Master application no -
(30) Prioritet 17. raar. 1975, 21520/75, IT(30) Priority 17. weird. 1975, 21520/75, IT
(71) Ansøger MIC S.P.A., Palermo, IT.(71) Applicant MIC S.P.A., Palermo, IT.
(72) Opfinder Carlo Neri, IT: Gioacchino frLprlani, IT.(72) Inventor Carlo Neri, IT: Gioacchino frLprlani, IT.
(74) Fuldmægtig internationalt Patent-Bureau.(74) International Patent Bureau.
(54) Fremgangsmåde til fremstilling af ethylencarbonat eller propylencar= bonat.(54) Process for the preparation of ethylene carbonate or propylene carbonate.
Opfindelsen angår en særlig fremgangsmåde til fremstilling af ethylencar- bonat eller propylencarbonat ved omsætning af henholdsvis ethylenoxid eller propy- lenoxid med carbondioxid i nærværelse af en katalysator.The invention relates to a particular process for the preparation of ethylene carbonate or propylene carbonate by reacting ethylene oxide or propylene oxide with carbon dioxide in the presence of a catalyst, respectively.
Der kendes fremgangsmåder af denne art, hvor man som katalysator anvender en nitrogenholdig base. Således kendes der fra britisk patentskrift nr. 760.966 ^ en sådan fremgangsmåde, hvorved man imidlertid må arbejde ved temperaturer på 180- q 200°C og tryk på 50-100 atmosfærer for at opnå tilfredsstillende udbytter. Også 00 fra tysk fremlæggelsesskrift nr. 1.008.315 kendes der en sådan fremgangsmåde,Methods of this kind are known, whereby as a catalyst a nitrogen-containing base is used. Thus, such a process is known from British Patent Specification No. 760,966, whereby, however, one must operate at temperatures of 180 ° C to 200 ° C and pressures of 50-100 atmospheres to obtain satisfactory yields. Also, from German German Patent Specification No. 1,008,315, such a method is known,
Lf) hvor man eventuelt desuden arbejder i nærværelse af et fortyndingsmiddel, såsom *““ dioxan. Ved sidstnævnte fremgangsmåde skal der arbejdes ved temperaturer mellem ^ 100 og 400°C og et tryk på over 35 at. Ifølge eksemplerne i nævnte fremlæggelses- Ω skrift arbejdes der imidlertid altid ved tryk over 100 at.Lf) where it is also optionally employed in the presence of a diluent such as * "" dioxane. In the latter process, work must be carried out at temperatures between ^ 100 and 400 ° C and a pressure exceeding 35 at. However, according to the examples in said presentation Ω above 100 pressures are always worked.
145300 2145300 2
Det har nu vist sig, at man ved anvendelse af en kombination af en alkanol og en nitrogenholdig base som katalysator kan opnå høje udbytter ved lavere temperaturer og ved lavere tryk end de ved de kendte fremgangsmåder anvendte. Navnlig muligheden af at anvende lavere tryk betyder en lettelse af arbejdsbetingelserne.It has now been found that using a combination of an alkanol and a nitrogenous base as a catalyst, high yields can be obtained at lower temperatures and at lower pressures than those used in the known processes. In particular, the possibility of using lower pressures means a reduction in working conditions.
I overensstemmelse med det ovenstående er fremgangsmåden ifølge opfindelsen ejendommelig ved, at katalysatoren består af en kombination af en alkanol og en nitrogenholdig base.In accordance with the above, the process according to the invention is characterized in that the catalyst consists of a combination of an alkanol and a nitrogenous base.
Det er også kendt, at ethylencarbonat eller propylencarbonat kan syntetiseres under anvendelse af katalysatorer, der er dannet af tetraalkylammoniumhalo-genider, ved temperaturer omkring 200°C og CC^-tryk i nærheden af 200 atmosfærer. Anvendelsen af sådanne katalysatorer under de ovenfor angivne betingelser fremby-der betydelige tekniske vanskeligheder, som er forbundet med konstruktionen af anlæggene eller fremkomsten af korrosionsproblemer, som netop skyldes katalysatorernes kemiske natur.It is also known that ethylene carbonate or propylene carbonate can be synthesized using catalysts formed from tetraalkylammonium halides at temperatures around 200 ° C and CC₂ pressure in the vicinity of 200 atmospheres. The use of such catalysts under the above conditions presents significant technical difficulties associated with the design of the plants or the occurrence of corrosion problems due precisely to the chemical nature of the catalysts.
fremgangsmåden ifølge opfindelsen muliggør fremstilling af ethylencarbonat eller propylencarbonat ud fra ethylenoxid eller propylenoxid og under mindre drastiske betingelser og uden noget halogenid er til stede i det hele taget.the process of the invention enables the preparation of ethylene carbonate or propylene carbonate from ethylene oxide or propylene oxide and under less drastic conditions and without any halide present at all.
Eksempler på alkanoler, der kan anvendes ved fremgangsmåden ifølge opfindelsen, er methanol, ethanol, cyclohexanol og butanol, medens den nitrogenholdige base f.eks. kan vælges blandt trimethylamin, triethylamin, pyridin og dimethyl-anilin. Det er interessant, at den nitrogenholdige base også kan bestå af en basisk nitrogenholdig harpiks, der er uopløselig i reaktionsmediet, som sædvanligvis udgøres af ethylenoxidet eller propylenoxidet som sådant i blanding med den benyttede alkanol, men denne blanding kan dog også være fortyndet med et vilkårligt indifferent opløsningsmiddel.Examples of alkanols which can be used in the process of the invention are methanol, ethanol, cyclohexanol and butanol, while the nitrogenous base e.g. can be selected from trimethylamine, triethylamine, pyridine and dimethyl-aniline. Interestingly, the nitrogen-containing base may also consist of a basic nitrogen-containing resin which is insoluble in the reaction medium usually constituted by the ethylene oxide or propylene oxide as such in admixture with the alkanol used, but this mixture may also be diluted with any inert solvent.
Der kan benyttes forskellige hensigtsmæssige udførelsesformer for fremgangsmåden ifølge opfindelsen.Various convenient embodiments of the method according to the invention may be used.
Ifølge opfindelsen er det således hensigtsmæssigt, at mængden af den katalysatorkomponent, der er mindst af,ligger i omradet fra 0,1 til 30 vægtJ 1 forhold til vægten af ethylenoxid eller propylenoxid. Forholdet mellem de to katalysatorkomponenter er ikke væsentligt, idet det er muligt at arbejde med et overskud af den iiitrogenholdige base eller af alkanolen i forhold til den anden,men det sidste foretrækkes dog.Thus, according to the invention, it is desirable that the amount of the least catalyst component be in the range of 0.1 to 30% by weight of ethylene oxide or propylene oxide. The ratio of the two catalyst components is not significant, since it is possible to work with an excess of the nitrogenous base or of the alkanol relative to the other, but the latter is preferred.
. Ifølge opfindelsen er det endvidere hensigtsmæssigt, at omsætningen udføres ved temperaturer i området fra 0°C til 200°C, fortrinsvis mellem 80°C og 120°C, og under et tryk mellem 1 og 100 atmosfærer, fortrinsvis fra 1 til 30 atmosfærer.. Furthermore, according to the invention, it is convenient for the reaction to be carried out at temperatures in the range of 0 ° C to 200 ° C, preferably between 80 ° C and 120 ° C, and under a pressure between 1 and 100 atmospheres, preferably from 1 to 30 atmospheres.
Ved disse udførelsesformer opnår man især høje udbytter pr. tidsenhed, og idet man efter destillativ oparbejdning af reaktionsblandingen har mulighed for 3 U5300 kvantitativ recirkulering af ikke omsatte stoffer og katalysatorkomponenterne, kan man herigennem opnå praktisk taget kvantitative udbytter.In these embodiments, high yields are obtained in particular. time unit, and since after distillative processing of the reaction mixture it is possible to quantitatively recycle unreacted substances and the catalyst components, practically quantitative yields can be obtained.
Omsætningen kan udføres enten kontinuerligt eller chargevis og enten i homogen eller heterogen fase.The reaction can be carried out either continuously or batchwise and either in homogeneous or heterogeneous phase.
Dersom der er tale om en chargevis udførelsesform for fremgangsmåden, kan denne f.eks. bestå i, at ethylenoxid eller propylenoxid og den nitrogenholdige base og alkanolen fyldes på en autoklav, hvorefter CO2 tilføres under det ønskede tryk. Blandingen opvarmes på et bad til den ønskede temperatur, og trykket holdes konstant ved at tilføre CO2 fra en bombe. Så snart der ikke sker yderligere absorption, tømmes autoklaven, og væsken destilleres. Alkanolen og den nitrogenholdige base kan genvindes og recirkuleres.In the case of a case-by-case embodiment of the method, the latter may e.g. consist of ethylene oxide or propylene oxide and the nitrogenous base and alkanol being charged to an autoclave, after which CO2 is supplied under the desired pressure. The mixture is heated in a bath to the desired temperature and the pressure is kept constant by adding CO2 from a bomb. As soon as no further absorption occurs, the autoclave is emptied and the liquid distilled. The alkanol and nitrogenous base can be recovered and recycled.
Er der derimod tale om en kontinuerlig udførelsesform for fremgangsmåden, består denne f.eks. i, at der gennem en lodret reaktor, der er opvarmet til den ønskede temperatur og fyldt med en basisk, ikke til salt omdannet harpiks, flyder en blanding af ethylenoxid eller propylenoxid og en alkanol under CC^-tryk. Efflu-enten kondenseres og destilleres herefter således, at "forløbene" er ethylenoxid eller propylenoxid og alkanolen, der atter bringes tilbage til reaktorens top med CC^, medens "destillationsresten" består af det ved processen dannede ethylencar-bonat eller propylencarbonat.In contrast, in the case of a continuous embodiment of the method, this consists e.g. in that through a vertical reactor heated to the desired temperature and filled with a basic, non-salt converted resin, a mixture of ethylene oxide or propylene oxide and an alkanol flow under CC 2 pressure. The effluent is then condensed and distilled so that the "processes" are ethylene oxide or propylene oxide and the alkanol, which is again returned to the reactor's peak with CC
Fremgangsmåden ifølge opfindelsen belyses nærmere ved hjælp af de efterfølgende eksempler.The process according to the invention is further elucidated by the following examples.
Eksempe1 1Example1 1
Til en 300 ml autoklav , der er udstyret med omrører, sættes 60 g ethylenoxid, 15 g CH30H og 3,6 g Et3N.To a 300 ml autoclave equipped with stirrer is added 60 g of ethylene oxide, 15 g of CH 3 OH and 3.6 g of Et 3 N.
Carbondioxid ledes ved stuetemperatur under et tryk på 10 kg/cm gennem blandingen, idet denne opvarmes til 50°C.Carbon dioxide is passed at room temperature under a pressure of 10 kg / cm through the mixture, heated to 50 ° C.
Trykket forøges på grund af opvarmningen, og det holdes på dets maksimumværdi ved kontinuert at tilføre den mængde CO2, der omsættes. Ctasætningen følges ved gaschromatografi.The pressure is increased due to the heating and it is maintained at its maximum value by continuously adding the amount of CO2 that is converted. The ctase is followed by gas chromatography.
Efter 60 minutters omsætning er der en omdanne Isesgrad på 30%, og udbyttet af ethylencarbonat er 29%.After 60 minutes of turnover, there is a convert grade of 30% and the yield of ethylene carbonate is 29%.
Eksempel 2Example 2
Man følger den samme fremgangsmåde som i det foregående eksempel. Den eneste forskel er, at arbejdstemperaturen holdes i nærheden af 80°C. Efter 60 minutters omsætning, er der en omdanne Isesgrad på 70%,og ethylencarbonat opnås i et udbytte på 68%.The same procedure is followed as in the previous example. The only difference is that the working temperature is kept close to 80 ° C. After 60 minutes of turnover, there is a 70% conversion rate of ice, and ethylene carbonate is obtained in 68% yield.
145300 4145300 4
Eksempel 3Example 3
Man anvender den samme blanding som i eksempel 1, med den forskel at arbejde temperaturen holdes i nærheden af 110°G. Efter 1 times omsætning er der en omdannelsesgrad så høj som 92%, og ethylencarbonatudbyttet er 90%.The same mixture is used as in Example 1, with the difference that the working temperature is kept near 110 ° G. After 1 hour of conversion there is a conversion rate as high as 92% and the ethylene carbonate yield is 90%.
Eksempel 4Example 4
Man anvender den samme fremgangsmåde som i eksempel 1 kun med den forskel, 2 at CO2 tilføres ved stuetemperatur og under et tryk på 30 kg/cm , og at omsætnings temperaturen bringes op på 80°C.The same procedure as in Example 1 is used only with the difference 2 that CO2 is supplied at room temperature and under a pressure of 30 kg / cm and that the reaction temperature is raised to 80 ° C.
Efter 60 minutters omsætning er der en omdannelsesgrad på 83%, samt et ethylencarbonatudbytte på 81%.After 60 minutes of turnover, there is a conversion rate of 83% and an ethylene carbonate yield of 81%.
Eksempel 5 (sammenligningseksempel)Example 5 (Comparative Example)
Man anvender den samme fremgangsmåde som i eksempel 1, men med den forskel at der ikke tilsættes triethylamin.The same procedure is used as in Example 1, but with the difference that triethylamine is not added.
Efter 2 timers omsætning er der intet spor af ethylencarbonat, selv ikke det ringeste spor.After 2 hours of reaction there is no trace of ethylene carbonate, not even the slightest trace.
Eksempel 6 (sammenligningseksempel)Example 6 (Comparative Example)
Man følger den samme fremgangsmåde som i eksempel 1, men med den forskel at reaktionsblandingen ikke indeholder CH^OH overhovedet.The same procedure is followed as in Example 1, but with the difference that the reaction mixture does not contain CH 2 OH at all.
Efter mere end 2 timers omsætning findes der ikke det ringeste spor af e thylencarb onat.After more than 2 hours of turnover, the slightest trace of thylenecarb onate is not found.
Eksempe1 7Example1 7
Man anvender samme fremgangsmåde som i eksempel 2, bortset fra at triethylamin er erstattet med en ækvimolær mængde pyridin.The same procedure as in Example 2 is used except that triethylamine is replaced by an equimolar amount of pyridine.
Efter 60 minutters omsætning findes en omdannelse på 60% og et udbytte af ethylencarbonat på 50%.After 60 minutes of reaction there is a conversion of 60% and a yield of ethylene carbonate of 50%.
Eksempel 8Example 8
Fremgangsmåden er den samme som i eksempel 2, bortset fra den nitrogenhol-dige base, som er en ækvimolær mængde dimethylanilin.The procedure is the same as in Example 2, except for the nitrogen-containing base, which is an equimolar amount of dimethylaniline.
Efter 60 minutters omsætning er omdannelsesgraden 68% sammen med et udbytte på 65% ethylencarbonat.After 60 minutes of reaction, the conversion rate is 68% together with a yield of 65% ethylene carbonate.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2132075 | 1975-03-17 | ||
| IT21320/75A IT1034323B (en) | 1975-03-17 | 1975-03-17 | PROCEDURE FOR THE PREPARATION OF ALKYLENCARBONATES |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK112576A DK112576A (en) | 1976-09-18 |
| DK145300B true DK145300B (en) | 1982-10-25 |
| DK145300C DK145300C (en) | 1983-03-21 |
Family
ID=11180058
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK112576A DK145300C (en) | 1975-03-17 | 1976-03-16 | PROCEDURE FOR PREPARING ETHYLENE CARBONATE OR PROPYLENE CARBONATE |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS51118763A (en) |
| BE (1) | BE839609A (en) |
| CA (1) | CA1076590A (en) |
| CH (1) | CH620434A5 (en) |
| DE (1) | DE2611087C3 (en) |
| DK (1) | DK145300C (en) |
| ES (1) | ES446341A1 (en) |
| FR (1) | FR2304609A1 (en) |
| GB (1) | GB1485925A (en) |
| IE (1) | IE43215B1 (en) |
| IT (1) | IT1034323B (en) |
| LU (1) | LU74557A1 (en) |
| NL (1) | NL171706C (en) |
| NO (1) | NO144263C (en) |
| SE (1) | SE426944B (en) |
| ZA (1) | ZA761449B (en) |
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|---|---|---|---|---|
| US4314945A (en) * | 1977-12-22 | 1982-02-09 | Union Carbide Corporation | Alkylene carbonate process |
| US5138073A (en) * | 1981-12-02 | 1992-08-11 | Scientific Design Company, Inc. | Preparation of alkylene carbonates |
| US5023345A (en) * | 1981-12-02 | 1991-06-11 | Scientific Design Company, Inc. | Preparation of alkylene carbonates |
| US4786741A (en) * | 1982-11-15 | 1988-11-22 | Scientific Design Company, Inc. | Preparation of alkylene carbonates |
| US4841072A (en) * | 1981-12-02 | 1989-06-20 | Scientific Design Company, Inc. | Preparation of alkylene carbonates |
| GB8307613D0 (en) * | 1983-03-18 | 1983-04-27 | Bp Chem Int Ltd | Carbonates |
| DE3529263A1 (en) * | 1985-08-16 | 1987-02-19 | Hoechst Ag | METHOD FOR PRODUCING 2-OXO-1,3-DIOXOLANES |
| DE3600602A1 (en) * | 1986-01-11 | 1987-07-16 | Hoechst Ag | METHOD FOR PRODUCING 2-OXO-1,3-DIOXOLANES |
| DE4105554A1 (en) | 1991-02-22 | 1992-08-27 | Bayer Ag | METHOD FOR PRODUCING DIALKYL CARBONATES |
| DE4129753C2 (en) * | 1991-09-04 | 1995-05-04 | Dainippon Ink & Chemicals | Process for the preparation of cyclocarbonate compounds |
| AU678805B2 (en) * | 1993-01-06 | 1997-06-12 | Akzo N.V. | Oligomeric sterically hindered polyamide crosslinkers and coating compositions containing the same |
| US6077929A (en) * | 1996-10-09 | 2000-06-20 | Akzo Nobel N.V. | Internally blocked polyamine crosslinkers and coating compositions containing the same |
| WO2010089264A1 (en) | 2009-02-05 | 2010-08-12 | Basf Se | Method for producing bicarbonates |
| DE102015113351A1 (en) | 2014-09-20 | 2016-03-24 | Fischerwerke Gmbh & Co. Kg | Hardenable synthetic resin with significant amounts of cyclic carbonate groups, and / and cyclocarbonate resin-based fastening systems, their preparation and use |
| TWI618577B (en) * | 2016-02-01 | 2018-03-21 | 新綠科學股份有限公司 | Method for producing metal carbonate and catalyst for producing the same |
| RU2018141403A (en) | 2016-04-29 | 2020-05-29 | Хенкель Аг Унд Ко. Кгаа | AMIN-FUNCTIONAL POLYMERS AND METHODS FOR PRODUCING SUCH POLYMERS |
| EP3401348A1 (en) | 2017-05-11 | 2018-11-14 | Henkel AG & Co. KGaA | Method for producing functionalized polyesters |
| EP3409707A1 (en) | 2017-05-30 | 2018-12-05 | Henkel AG & Co. KGaA | Method for producing functionalized polyesters |
| EP3428216B1 (en) | 2017-07-11 | 2022-11-02 | Henkel AG & Co. KGaA | Method for producing functionalized polyesters |
| KR20210020916A (en) | 2018-06-19 | 2021-02-24 | 헨켈 아게 운트 코. 카게아아 | Highly active double metal cyanide compound |
| EP3725820B1 (en) | 2019-04-16 | 2022-04-06 | Henkel AG & Co. KGaA | Use of functionalized alpha-angelica lactones |
| WO2021004624A1 (en) | 2019-07-09 | 2021-01-14 | Henkel Ag & Co. Kgaa | Two component (2k) composition based on modified epoxy resins |
| EP3798246B1 (en) | 2019-09-27 | 2024-01-31 | Henkel AG & Co. KGaA | One component (1k) composition based on modified epoxy resin |
| EP3831863B1 (en) | 2019-12-04 | 2023-07-05 | Henkel AG & Co. KGaA | One component (1k) composition based on epoxy resin |
| EP3831862B1 (en) | 2019-12-04 | 2023-06-28 | Henkel AG & Co. KGaA | One component (1k) composition based on epoxy resin |
| EP3835378A1 (en) | 2019-12-13 | 2021-06-16 | Henkel AG & Co. KGaA | Two component (2k) curable adhesive composition |
| EP3835383B1 (en) | 2019-12-13 | 2023-04-12 | Henkel AG & Co. KGaA | One component (1k) curable adhesive composition |
| EP3835386B8 (en) | 2019-12-13 | 2024-01-10 | Henkel AG & Co. KGaA | Two component (2k) curable adhesive composition |
| PL3835381T3 (en) | 2019-12-13 | 2023-06-26 | Henkel Ag & Co. Kgaa | Two component (2k) curable adhesive composition |
| EP3916033A1 (en) | 2020-05-28 | 2021-12-01 | Henkel AG & Co. KGaA | One component (1k) composition based on epoxy resin |
| EP3943564B1 (en) | 2020-07-21 | 2024-07-17 | Henkel AG & Co. KGaA | Room temperature stable, electrically conductive 1k epoxy formulation |
| TW202219214A (en) | 2020-08-27 | 2022-05-16 | 德商漢高股份有限及兩合公司 | Electrically conductive one component (1k) epoxy formulation |
| WO2022081271A1 (en) | 2020-10-13 | 2022-04-21 | Cabot Corporation | Conductive photo-curable compositions for additive manufacturing |
| EP4015557A1 (en) | 2020-12-21 | 2022-06-22 | Henkel AG & Co. KGaA | Two component (2k) epoxy formulation |
| EP4050061A1 (en) | 2021-02-26 | 2022-08-31 | Henkel AG & Co. KGaA | Near-infrared (nir) sensitized adhesive and sealant compositions |
| EP4050060A1 (en) | 2021-02-26 | 2022-08-31 | Henkel AG & Co. KGaA | A photocurable adhesive or sealant composition |
| EP4159784A1 (en) | 2021-09-30 | 2023-04-05 | Henkel AG & Co. KGaA | Two component (2k) composition based on epoxy (meth)acrylate resin |
| WO2023241875A1 (en) | 2022-06-17 | 2023-12-21 | Henkel Ag & Co. Kgaa | Two component (2k) curable adhesive composition |
| EP4332144A1 (en) | 2022-09-05 | 2024-03-06 | Henkel AG & Co. KGaA | One component (1k) curable adhesive composition |
| WO2024078879A1 (en) | 2022-10-12 | 2024-04-18 | Henkel Ag & Co. Kgaa | Two component (2k) epoxy formulation |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4516028Y1 (en) * | 1965-08-30 | 1970-07-03 | ||
| JPS4628735Y1 (en) * | 1968-12-26 | 1971-10-05 |
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1975
- 1975-03-17 IT IT21320/75A patent/IT1034323B/en active
-
1976
- 1976-03-09 ZA ZA761449A patent/ZA761449B/en unknown
- 1976-03-12 GB GB10095/76A patent/GB1485925A/en not_active Expired
- 1976-03-15 LU LU74557A patent/LU74557A1/xx unknown
- 1976-03-15 IE IE543/76A patent/IE43215B1/en unknown
- 1976-03-15 CA CA247,964A patent/CA1076590A/en not_active Expired
- 1976-03-15 NO NO760900A patent/NO144263C/en unknown
- 1976-03-16 DE DE2611087A patent/DE2611087C3/en not_active Expired
- 1976-03-16 NL NLAANVRAGE7602749,A patent/NL171706C/en not_active IP Right Cessation
- 1976-03-16 BE BE165201A patent/BE839609A/en not_active IP Right Cessation
- 1976-03-16 FR FR7607529A patent/FR2304609A1/en active Granted
- 1976-03-16 CH CH327376A patent/CH620434A5/en not_active IP Right Cessation
- 1976-03-16 DK DK112576A patent/DK145300C/en not_active IP Right Cessation
- 1976-03-16 ES ES446341A patent/ES446341A1/en not_active Expired
- 1976-03-17 JP JP51028208A patent/JPS51118763A/en active Pending
- 1976-03-17 SE SE7603360A patent/SE426944B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK145300C (en) | 1983-03-21 |
| IE43215L (en) | 1976-09-17 |
| IE43215B1 (en) | 1981-01-14 |
| NO144263B (en) | 1981-04-21 |
| ZA761449B (en) | 1977-03-30 |
| DE2611087A1 (en) | 1976-09-23 |
| NL171706B (en) | 1982-12-01 |
| GB1485925A (en) | 1977-09-14 |
| AU1194376A (en) | 1977-09-15 |
| FR2304609A1 (en) | 1976-10-15 |
| DK112576A (en) | 1976-09-18 |
| NO760900L (en) | 1976-09-20 |
| CA1076590A (en) | 1980-04-29 |
| FR2304609B1 (en) | 1978-10-13 |
| IT1034323B (en) | 1979-09-10 |
| BE839609A (en) | 1976-09-16 |
| DE2611087B2 (en) | 1978-11-09 |
| LU74557A1 (en) | 1976-09-01 |
| JPS51118763A (en) | 1976-10-18 |
| DE2611087C3 (en) | 1979-07-05 |
| NO144263C (en) | 1981-07-29 |
| NL171706C (en) | 1983-05-02 |
| ES446341A1 (en) | 1977-06-16 |
| NL7602749A (en) | 1976-09-21 |
| SE426944B (en) | 1983-02-21 |
| CH620434A5 (en) | 1980-11-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |