NO123148B - - Google Patents
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- Publication number
- NO123148B NO123148B NO167730A NO16773067A NO123148B NO 123148 B NO123148 B NO 123148B NO 167730 A NO167730 A NO 167730A NO 16773067 A NO16773067 A NO 16773067A NO 123148 B NO123148 B NO 123148B
- Authority
- NO
- Norway
- Prior art keywords
- chloro
- ring
- acid
- alkyl
- carboxylic acid
- Prior art date
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- -1 3-cyanopropyl Chemical group 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 4
- JWFVGQJHBVZECV-UHFFFAOYSA-N 5-amino-2-chloropentanoic acid hydrochloride Chemical compound Cl.ClC(C(=O)O)CCCN JWFVGQJHBVZECV-UHFFFAOYSA-N 0.000 claims description 3
- CBRSWZYPLFGNGQ-UHFFFAOYSA-N 6-amino-2-chlorohexanoic acid;hydrochloride Chemical compound Cl.NCCCCC(Cl)C(O)=O CBRSWZYPLFGNGQ-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 2
- YJJLOESDBPRZIP-UHFFFAOYSA-N diethyl 2-(2-cyanoethyl)propanedioate Chemical compound CCOC(=O)C(CCC#N)C(=O)OCC YJJLOESDBPRZIP-UHFFFAOYSA-N 0.000 claims 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- CIBGXJVJPZCMFX-UHFFFAOYSA-N 2-bromobutanenitrile Chemical compound CCC(Br)C#N CIBGXJVJPZCMFX-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical group CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 229960001701 chloroform Drugs 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VLSMHEGGTFMBBZ-OOZYFLPDSA-M Kainate Chemical compound CC(=C)[C@H]1C[NH2+][C@H](C([O-])=O)[C@H]1CC([O-])=O VLSMHEGGTFMBBZ-OOZYFLPDSA-M 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04C—STRUCTURAL ELEMENTS; BUILDING MATERIALS
- E04C2/00—Building elements of relatively thin form for the construction of parts of buildings, e.g. sheet materials, slabs, or panels
- E04C2/02—Building elements of relatively thin form for the construction of parts of buildings, e.g. sheet materials, slabs, or panels characterised by specified materials
- E04C2/10—Building elements of relatively thin form for the construction of parts of buildings, e.g. sheet materials, slabs, or panels characterised by specified materials of wood, fibres, chips, vegetable stems, or the like; of plastics; of foamed products
- E04C2/20—Building elements of relatively thin form for the construction of parts of buildings, e.g. sheet materials, slabs, or panels characterised by specified materials of wood, fibres, chips, vegetable stems, or the like; of plastics; of foamed products of plastics
- E04C2/205—Building elements of relatively thin form for the construction of parts of buildings, e.g. sheet materials, slabs, or panels characterised by specified materials of wood, fibres, chips, vegetable stems, or the like; of plastics; of foamed products of plastics of foamed plastics, or of plastics and foamed plastics, optionally reinforced
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04C—STRUCTURAL ELEMENTS; BUILDING MATERIALS
- E04C2/00—Building elements of relatively thin form for the construction of parts of buildings, e.g. sheet materials, slabs, or panels
- E04C2/02—Building elements of relatively thin form for the construction of parts of buildings, e.g. sheet materials, slabs, or panels characterised by specified materials
- E04C2/26—Building elements of relatively thin form for the construction of parts of buildings, e.g. sheet materials, slabs, or panels characterised by specified materials composed of materials covered by two or more of groups E04C2/04, E04C2/08, E04C2/10 or of materials covered by one of these groups with a material not specified in one of the groups
- E04C2/284—Building elements of relatively thin form for the construction of parts of buildings, e.g. sheet materials, slabs, or panels characterised by specified materials composed of materials covered by two or more of groups E04C2/04, E04C2/08, E04C2/10 or of materials covered by one of these groups with a material not specified in one of the groups at least one of the materials being insulating
- E04C2/292—Building elements of relatively thin form for the construction of parts of buildings, e.g. sheet materials, slabs, or panels characterised by specified materials composed of materials covered by two or more of groups E04C2/04, E04C2/08, E04C2/10 or of materials covered by one of these groups with a material not specified in one of the groups at least one of the materials being insulating composed of insulating material and sheet metal
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04D—ROOF COVERINGS; SKY-LIGHTS; GUTTERS; ROOF-WORKING TOOLS
- E04D3/00—Roof covering by making use of flat or curved slabs or stiff sheets
- E04D3/35—Roofing slabs or stiff sheets comprising two or more layers, e.g. for insulation
- E04D3/351—Roofing slabs or stiff sheets comprising two or more layers, e.g. for insulation at least one of the layers being composed of insulating material, e.g. fibre or foam material
- E04D3/352—Roofing slabs or stiff sheets comprising two or more layers, e.g. for insulation at least one of the layers being composed of insulating material, e.g. fibre or foam material at least one insulating layer being located between non-insulating layers, e.g. double skin slabs or sheets
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04D—ROOF COVERINGS; SKY-LIGHTS; GUTTERS; ROOF-WORKING TOOLS
- E04D3/00—Roof covering by making use of flat or curved slabs or stiff sheets
- E04D3/35—Roofing slabs or stiff sheets comprising two or more layers, e.g. for insulation
- E04D3/357—Roofing slabs or stiff sheets comprising two or more layers, e.g. for insulation comprising hollow cavities
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04D—ROOF COVERINGS; SKY-LIGHTS; GUTTERS; ROOF-WORKING TOOLS
- E04D3/00—Roof covering by making use of flat or curved slabs or stiff sheets
- E04D3/35—Roofing slabs or stiff sheets comprising two or more layers, e.g. for insulation
- E04D3/358—Roofing slabs or stiff sheets comprising two or more layers, e.g. for insulation with at least one of the layers being offset with respect to another layer
Landscapes
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Civil Engineering (AREA)
- Structural Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Casting Or Compression Moulding Of Plastics Or The Like (AREA)
- Laminated Bodies (AREA)
- Building Environments (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Description
Fremgangsmåte til fremstilling av lokalanestetisk virksomme o-N-alkylpiperidin- og a-N-alkyl-pyrrolidinkarbonsyreamider.
Foreliggende oppfinnelse angår en fremgangsmåte til fremstilling av u-N-alkyl-piperidin- og «-N-alkyl-pyrrolidinkarbonsyreamider med de generelle formler :
I disse formler betegner R en alkylgruppe og Ar en 2-alkyl-benzen- eller en 2,6-dialkylbenzengruppe.
De nevnte amider har vist seg å være overordentlig gode lokalbedøvelsesmidler, hvis effekt mange ganger overtreffer pro-kainets.
COOC,.Hr,
i Ifølge oppfinnelsen fremstilles disse syreamider ved på kjent måte å koble dietylmalonat med a-brombutyronitril til 3-cyanpropyl-malondietylester eller ved å koble dietylmalonat med akrylnitril til 2-cyanetyl-malondietylester. Etter reduk-sjon med Raney-nikkel og hydrogengass fåes en 7-ring resp. en 6-ring. 7-ringen som består av 2-ketoheksametylenimin-3-karbonsyreetylester og 6-ringen som består av 2-piperidon-3-karbonsyreetylester kloreres begge i 3-stillingen med sulfurylklorid. De erholdte kloreringsprodukter kokes med saltsyre, hvorved ringene åpnes, r og man får 2-klor-6-aminokapronsyrehy-droklorid resp. 2-klor-5-aminovaleriansyre-hydroklorid, som kloreres ifølge Fischer (Liebigs Annalen, 363, 1908) til syreklor-ider. Man lar derpå syrekloridene reagere med et aromatisk amin med den generelle formel NHL»Ar (i hvilken Ar har den ovenfor angitte betydning) til amider av vedkom-ovennevnte amider lukkes under innvirk-mende syrer. De åpne kullstoff kjeder i ning av alkalilut så at man får a-piperidin-- karbonsyreamid og u-pyrrolidinkarbonsyre-i amid, som derpå N-alkyleres i nitrogen-ringen med vanlige alkyleringsmidler f. eks. i dialkylsulfat eller ålkylhalogenid. Fremgangsmåten ifølge oppfinnelsen - belyses nærmere ved følgende reaksjons-skjema i hvilket de enkelte trin er vist.
COOC2H-,
I det følgende beskrives som eksempler to utførelsesformer for oppfinnelsen.
Eksempel 1.
182 vektsdeler natriummalonester kobles med 148 vektsdeler a-brombutyronitril i absolutt alkohol. Etter 8 timers koking suges natriumbromidet fra, og etanol og ikke reagert brombutyronitril drives av med vanndamp. Residuet ekstraheres med eter og tørres med natriumsulfat. Eteren drives av, og residuet destilleres i vakuum. Kokepunkt 135—37° C. ved 1 mm. Den erholdte 3-cyanpropylmalonester hydreres med hydrogengass og Raney-nikkel i alko-holisk oppløsning ved 80° C. under 75 atm. overtrykk i 5 timer. Alkoholen avdestilleres, og residuet som består av 2-ketoheksametylenimin-3-karbonsyreetylester
kloreres med 0,75 deler sulfurylklorid opp-løst i kloroform ved koking i 1 time. Kloro-formen avdestilleres i vakuum. Residuet kokes med 2 deler konsentrert saltsyre i 5 timer. Etter filtrering gjennom kull og inndampning i vakuum fåes 2-klor-6-amino-kapronsyrehydroklorid som en olje. Man lar denne tørre i vakuumeksikkator. Oljen kloreres ifølge Fischer til syreklorid, som man etter suspendering i aceton lar reagere med 2 deler 2,6-xylidin. Oppløsnin-gen i aceton oppvarmes i en halv time på vannbad. Derpå avdestilleres acetonet, residuet oppløses i vann, og oppløsningen innstilles på en pH-verdi av 5,5. Overskuddet av xylidin fjernes ved ekstraksjon med eter. Den vandige oppløsning tilsettes lut til pH-verdi på 12, og man lar oppløsnin-gen stå et par dager ved romtemperatur, hvorved ringens lukning skjer så at man får pipekolylxylidid. Væske suges fra krystallene, basen vaskes med vann og tørres. Alkyleringen utføres ved oppvarming på vannbad med 2 deler dietylsulfat i 3 timer. Vann tilsettes, og oppløsningen ekstraheres med eter. Etter behandling med kull ved en pH-verdi på 5,5 utfelles basen som hvite krystaller, fra hvilke væske suges bort, hvorpå de vaskes med vann. Basen, som er N-etylpipekolyl-2,6-xylidid, er så ren at den kan brukes til fremstilling av salter.
Eksempel 2.
2-cyanetylbmalonsyreester hydreres til 2-piperidon-3-karbonsyreetylester på kjent måte. Produktet kloreres med sulfurylklorid og kokes med saltsyre hvorved man får 2-k'lor-5-aminovaleriansyrehydroklorid.
Dette floreres ifølge Fischer til syreklorid,
og man lar suspensjonen av syrekloridet i aceton reagere med 2 deler 2,6-xylidin. Det erholdte 2-klor-5-amino-valeryl-xylididhy-droklorid oppløses i vann, etter at acetonet er drevet av. pH-yerdien innstilles med lut på 5,5, og overskuddet av xylidin fjernes ved ekstraksjon med eter. Den vandige oppløsning gjøres alkalisk til en pH-verdi på 12 med lut, og man lar blandingen stå i 2 dager, hvorved ringdannelse foregår. Det erholdte prolylxylidid ekstraheres med eter. Eteren tørres'med natriumsulfat og drives av. Residuet alkyleres med 1 del dimetylsulfat ved oppvarming på vannbad i 5 timer. Residuet oppløses i vann, pH-verdien innstilles på 5,5, og oppløsningen behandles med kull. Basen utfelles med lut, væske suges fra krystallene, og de vaskes. Den erholdte base er N-metylpro-pyl-2,6-xylidid, og den kan uten ytterligere rensning brukes til fremstilling av salter.
Claims (1)
- Fremgangsmåte til fremstilling av lokalanéstetisk virksomme u-N-alkyl-pipe-ridin- og a-N-alkyl-pyrrolidinkarbonsyreamider med de generelle formler:i hvilke R betegner en alkylgruppe og Ar en 2-alkylbenzen- eller 2,6-dialkylbenzengruppe, karakterisert ved at man reduserer katalytisk med hydrogengass en 3-cyan-propyl- eller 2-cyanetylmalonsyredietyl-ester til 2-ketoheksametylenimin- eller 2-piperidon-3-karbonsyreetylester, hvoretter den erholdte 7-ring resp. 6-ring kloreres i 3-stillingen, f. eks. med sulfurylklorid, før ringen åpnes, f. eks. ved kokning med saltsyre, så at der dannes 2-klor-6-amino-kapronsyrehydroklorid resp. 2-klor-5-aminovaleriansyrehydroklorid, hvilke klo-
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5074/67A GB1150075A (en) | 1966-04-16 | 1966-04-16 | Improvements in or relating to manufacture of composite building sheets and building sheets so manufactured |
| GB1679066 | 1966-04-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO123148B true NO123148B (no) | 1971-10-04 |
Family
ID=26239603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO167730A NO123148B (no) | 1966-04-16 | 1967-04-14 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US3399503A (no) |
| BE (1) | BE696876A (no) |
| CH (1) | CH463752A (no) |
| DE (1) | DE1704951B2 (no) |
| DK (1) | DK118209B (no) |
| ES (2) | ES339312A1 (no) |
| GB (1) | GB1150075A (no) |
| LU (1) | LU53421A1 (no) |
| NL (1) | NL6705171A (no) |
| NO (1) | NO123148B (no) |
| SE (1) | SE329249B (no) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3479784A (en) * | 1967-12-05 | 1969-11-25 | Tru Lok Metal Fabricating Co I | Construction panel |
| US3482367A (en) * | 1968-04-12 | 1969-12-09 | Robertson Co H H | Field erected insulated wall structure |
| US3708943A (en) * | 1970-04-22 | 1973-01-09 | Olin Corp | Aluminum facing and roofing sheet system |
| US3849959A (en) * | 1972-11-14 | 1974-11-26 | Robertson Co H H | Building panel and laterally adjustable joint produced thereby |
| US3807103A (en) * | 1973-02-12 | 1974-04-30 | Robertson Co H H | Flashing member and wall structure utilizing the same |
| FR2225591B1 (no) * | 1973-04-12 | 1980-04-18 | Pennecot Jean | |
| US4373312A (en) * | 1978-04-04 | 1983-02-15 | Star Manufacturing Co. | Prefabricated panel construction system |
| US5857292A (en) * | 1979-11-13 | 1999-01-12 | Harold Simpson, Inc. | Roof support apparatus |
| US4348846A (en) * | 1980-10-02 | 1982-09-14 | Butler Manufacturing Company | Insulated roof |
| US4494348A (en) * | 1981-12-15 | 1985-01-22 | Kastelic Rudolph F | Pre-engineered modular building panel assembly |
| DE3306275A1 (de) * | 1983-02-23 | 1984-08-30 | Erwin 4795 Delbrück Küpper | Verfahren zur nachtraeglichen aeusseren isolierung von daechern und nach dem verfahren hergestellte isolierung von daechern |
| US5697197A (en) * | 1984-01-04 | 1997-12-16 | Harold Simpson, Inc. | Roof panel system having increased resistance to wind loads |
| DE3409768A1 (de) * | 1984-03-16 | 1985-09-19 | Allen Stefan Dipl.-Ing. 4000 Düsseldorf Wojcinski | Raumcontainer-schiessstaette |
| GB2200666A (en) * | 1987-01-30 | 1988-08-10 | Dufaylite Dev Ltd | Weatherproof and fireproof enclosures |
| DE4104237A1 (de) * | 1991-02-12 | 1992-08-13 | Martin Gumpp | Verfahren und vorrichtung zur herstellung eines ausgeschaeumten paneels |
| US5842315A (en) * | 1997-03-24 | 1998-12-01 | Tung Yik Trading Co., Ltd. | Corrugated board structure |
| US6085485A (en) * | 1997-12-11 | 2000-07-11 | Murdock; Douglas G. | Load bearing pre-fabricated building construction panel |
| ITTO20031035A1 (it) * | 2003-12-23 | 2005-06-24 | Isolpack S P A | Pannello isolante per edilizia. |
| US7540123B1 (en) * | 2006-03-09 | 2009-06-02 | Thomas Middleton Semmes | Base for rooftop air conditioning units |
| US7493729B1 (en) * | 2006-03-15 | 2009-02-24 | Thomas Middleton Semmes | Rooftop enclosure |
| IE86172B1 (en) * | 2007-05-01 | 2013-04-10 | Kingspan Res & Dev Ltd | A composite insulating panel having a heat exchange conduit means |
| US20110047908A1 (en) * | 2009-08-28 | 2011-03-03 | Brusman Bryan Daniel | High-strength insulated building panel with internal stud members |
| CA2777635C (en) * | 2009-10-16 | 2018-09-25 | Kingspan Holdings (Irl) Limited | A composite panel |
| USD668354S1 (en) | 2011-03-31 | 2012-10-02 | Firestone Building Products Company, Llc | Wall panel |
| USD667963S1 (en) | 2011-03-31 | 2012-09-25 | Firestone Building Products Company, Llc | Wall panel |
| USD668357S1 (en) | 2011-03-31 | 2012-10-02 | Firestone Building Products Company, Llc | Wall panel |
| USD668356S1 (en) | 2011-03-31 | 2012-10-02 | Firestone Building Products Company, Llc | Wall panel |
| USD668353S1 (en) | 2011-03-31 | 2012-10-02 | Firestone Building Products Company, Llc | Wall panel |
| MX353559B (es) | 2011-06-17 | 2018-01-18 | Lenmak Exterior Innovations Inc | Aparato y método para fabricar paneles de pared aislados. |
| CN104507797B (zh) * | 2012-07-06 | 2017-11-07 | C&D佐迪阿克公司 | 带有声学材料的飞机内部面板 |
| US9702147B2 (en) * | 2013-01-07 | 2017-07-11 | Clifford Eugene Babson | Panels for framing and constructing a building structure |
| US20140311077A1 (en) * | 2013-03-14 | 2014-10-23 | Amir Firouz | Structural Component System |
| US9845599B2 (en) | 2014-04-23 | 2017-12-19 | Nucor Corporation | Structural steel decking system and method of securing |
| US9863146B2 (en) | 2015-05-14 | 2018-01-09 | Nucor Corporation | Structural panel systems with a nested sidelap and method of securing |
| ITUB20153507A1 (it) * | 2015-09-09 | 2017-03-09 | Saip Surl | Apparecchiatura per la produzione di pannelli isolanti |
| CA3018206A1 (en) | 2016-03-21 | 2017-09-28 | Nucor Corporation | Structural systems with improved sidelap and buckling spans |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3062337A (en) * | 1958-10-30 | 1962-11-06 | Howe Sound Co | Insulated curtain wall structure |
-
1966
- 1966-04-16 GB GB5074/67A patent/GB1150075A/en not_active Expired
-
1967
- 1967-04-07 DE DE1967R0045719 patent/DE1704951B2/de active Granted
- 1967-04-11 BE BE696876D patent/BE696876A/xx unknown
- 1967-04-12 NL NL6705171A patent/NL6705171A/xx unknown
- 1967-04-13 CH CH517767A patent/CH463752A/de unknown
- 1967-04-14 ES ES339312A patent/ES339312A1/es not_active Expired
- 1967-04-14 LU LU53421D patent/LU53421A1/xx unknown
- 1967-04-14 NO NO167730A patent/NO123148B/no unknown
- 1967-04-14 DK DK206267AA patent/DK118209B/da unknown
- 1967-04-17 SE SE05302/67A patent/SE329249B/xx unknown
- 1967-04-17 US US631215A patent/US3399503A/en not_active Expired - Lifetime
- 1967-10-10 US US00674317A patent/US3733232A/en not_active Expired - Lifetime
-
1968
- 1968-02-15 ES ES350521A patent/ES350521A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES339312A1 (es) | 1968-07-16 |
| US3399503A (en) | 1968-09-03 |
| NL6705171A (no) | 1967-10-17 |
| US3733232A (en) | 1973-05-15 |
| BE696876A (no) | 1967-09-18 |
| DK118209B (da) | 1970-07-20 |
| ES350521A1 (es) | 1969-05-01 |
| DE1704951A1 (de) | 1971-06-03 |
| CH463752A (de) | 1968-10-15 |
| GB1150075A (en) | 1969-04-30 |
| LU53421A1 (no) | 1967-06-14 |
| SE329249B (no) | 1970-10-05 |
| DE1704951B2 (de) | 1976-08-12 |
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