DE2116105A1 - 3,3-bis-(heptafluoroisopropoxymethyl) oxetane - prepn from 3,3-bis-(halomethyl) oxetanes and heptafluoroisopropanolates and use - Google Patents
3,3-bis-(heptafluoroisopropoxymethyl) oxetane - prepn from 3,3-bis-(halomethyl) oxetanes and heptafluoroisopropanolates and useInfo
- Publication number
- DE2116105A1 DE2116105A1 DE19712116105 DE2116105A DE2116105A1 DE 2116105 A1 DE2116105 A1 DE 2116105A1 DE 19712116105 DE19712116105 DE 19712116105 DE 2116105 A DE2116105 A DE 2116105A DE 2116105 A1 DE2116105 A1 DE 2116105A1
- Authority
- DE
- Germany
- Prior art keywords
- bis
- oxetane
- heptafluoroisopropoxymethyl
- heptafluoroisopropanolates
- oxetanes
- 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.)
- Pending
Links
- SMMLFWZSFNNLAQ-UHFFFAOYSA-N 3,3-bis(1,1,1,2,3,3,3-heptafluoropropan-2-yloxymethyl)oxetane Chemical compound FC(F)(F)C(F)(C(F)(F)F)OCC1(COC(F)(C(F)(F)F)C(F)(F)F)COC1 SMMLFWZSFNNLAQ-UHFFFAOYSA-N 0.000 title description 5
- QVXZSAWOXGFNIK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropan-2-ol Chemical class FC(F)(F)C(F)(O)C(F)(F)F QVXZSAWOXGFNIK-UHFFFAOYSA-N 0.000 title description 2
- 150000002921 oxetanes Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 239000004753 textile Substances 0.000 abstract description 4
- 150000002118 epoxides Chemical class 0.000 abstract description 3
- 229920000742 Cotton Polymers 0.000 abstract description 2
- 239000004952 Polyamide Substances 0.000 abstract description 2
- 229910052794 bromium Inorganic materials 0.000 abstract description 2
- 229910052801 chlorine Inorganic materials 0.000 abstract description 2
- 238000011065 in-situ storage Methods 0.000 abstract description 2
- 239000012442 inert solvent Substances 0.000 abstract description 2
- 229910052740 iodine Inorganic materials 0.000 abstract description 2
- 229920002647 polyamide Polymers 0.000 abstract description 2
- 239000005871 repellent Substances 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 210000002268 wool Anatomy 0.000 abstract description 2
- 229920006149 polyester-amide block copolymer Polymers 0.000 abstract 1
- 239000002759 woven fabric Substances 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 239000002657 fibrous material Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- LNQMSHZIJJUXBS-UHFFFAOYSA-N potassium;1,1,1,2,3,3,3-heptafluoropropan-2-olate Chemical compound [K+].FC(F)(F)C(F)([O-])C(F)(F)F LNQMSHZIJJUXBS-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 3
- KEAWKRWTPFHLNX-UHFFFAOYSA-N 2,3-bis(1,1,1,2,3,3,3-heptafluoropropan-2-yloxymethyl)oxirane Chemical compound FC(C(C(F)(F)F)(OCC1C(COC(C(F)(F)F)(C(F)(F)F)F)O1)F)(F)F KEAWKRWTPFHLNX-UHFFFAOYSA-N 0.000 description 2
- RJFWXWNWUNDRLN-UHFFFAOYSA-N 2-(1,1,1,2,3,3,3-heptafluoropropan-2-yloxymethyl)oxirane Chemical compound FC(F)(F)C(F)(C(F)(F)F)OCC1CO1 RJFWXWNWUNDRLN-UHFFFAOYSA-N 0.000 description 2
- JRMFTYIUHNPQQY-UHFFFAOYSA-N 3,3-bis(iodomethyl)oxetane Chemical compound ICC1(CI)COC1 JRMFTYIUHNPQQY-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- -1 heptafluoroisopropoxymethyl Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- SWSOIFQIPTXLOI-HNQUOIGGSA-N (e)-1,4-dichlorobut-1-ene Chemical compound ClCC\C=C\Cl SWSOIFQIPTXLOI-HNQUOIGGSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RMPOAHSJSBVTBD-UHFFFAOYSA-N FC(C(F)(F)F)(C(F)(F)F)OCCC=COC(C(F)(F)F)(C(F)(F)F)F Chemical compound FC(C(F)(F)F)(C(F)(F)F)OCCC=COC(C(F)(F)F)(C(F)(F)F)F RMPOAHSJSBVTBD-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 238000009950 felting Methods 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D305/06—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Epoxy Compounds (AREA)
- Polyethers (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
3,3-Bis-(heptafluorisopropoxymethyl)-oxetan Die Erfindung betrifft als neue organische Verbindung 3,3-Bis- (heptafluorisopropoxymethyl) -oxetn. Die Erfindung betrifft ferner ein Verfahren zur Herstellung dieser Verbindung und die Verwendung der polymeren Verbindungen zur Behandlung faseriger Materialien. 3,3-bis (heptafluoroisopropoxymethyl) oxetane The invention relates to as a new organic compound 3,3-bis (heptafluoroisopropoxymethyl) -oxetn. the The invention also relates to a process for the preparation of this compound and the Use of the polymeric compounds to treat fibrous materials.
In der Beschreibung sind Teile und Prozente jeweils Gewichtsteile und Gewichtsprozente. Der Perfluorisopropylrest ist in der Beschreibung mit dem Symbol Q bezeichnet.In the description, parts and percentages are parts by weight and percentages by weight, respectively. The perfluoroisopropyl radical is denoted by the symbol Q in the description.
In der US-Patentschrift 3 361 685 sind Polymere beschrieben, welche sich vom Heptafluorisopropylglycidyläther ableiten.In US Pat. No. 3,361,685, polymers are described which derive from heptafluoroisopropyl glycidyl ether.
Dieser hat die Formel Diese polymeren Verbindungen verleihen Geweben ein Ölabweisungsvermögen Dieses blabweisungsvermögen ist jedoch nicht in allen Fällen ausreichend.This one has the formula These polymeric compounds impart oil repellency to fabrics. However, this blue repellency is not sufficient in all cases.
Es hat deshalb nicht an Versuchen gefehlt, den Gehalt an Pluoralkylgruppen in einem Molekül zu erhöhen, um das ölschmutzabweisungsvermögen zu verbessern. So ist beispielsweise in der deutschen Patentanmeldung P 20 59 013 vorgeschlagen worden, 1,4-Dichlorbuten-<2) mit Alkaliheptafluorisopropanolat umzusetzen und das erhaltene Produkt zum 1,4-Bis-(heptafluorisopropoxy)-2,3-epoxy-butan tu oxydieren.There has therefore been no lack of attempts to ascertain the content of fluoroalkyl groups in a molecule to increase oil soil repellency. So has been proposed, for example, in German patent application P 20 59 013, 1,4-dichlorobutene <2) to implement with alkali heptafluoroisopropoxide and the obtained Oxidize the product to 1,4-bis (heptafluoroisopropoxy) -2,3-epoxy-butane.
Die hieraus durch Polymerisation hergestellten höhermole;ularen Verbindungen zeichnen sich durch höheres ölabweisungsvermögen aus. Jedoch ist die Herstellung dieser Verbindungen, insbesondere die Epoxydierung des 1,4-Bis-(heptafluorisopropoxy)-butens-(2), verhältnismäßig aufwendig und kompliziert.The higher molecular weight compounds produced therefrom by polymerization are characterized by higher oil repellency. However, the manufacture is of these compounds, in particular the epoxidation of 1,4-bis (heptafluoroisopropoxy) butene (2), relatively expensive and complicated.
Der vorliegenden Erfindung liegt deshalb die Aufgabe zugrunde, neue Verbindungen aufzufinden, welche leicht herstellbar sind, gut polymerisiert werden können und den mit ihnen behandelten Fasern ein ausgezeichnetes blabweisungsvermögen verleihen Außerdem sollen diese Verbindungen den Griff des mit ihnen behandelten Textilmaterials günstig beeinflussen.The present invention is therefore based on the object of new Finding compounds that are easy to make, polymerize well and the fibers treated with them have excellent blab-repellent properties In addition, these compounds are intended to give the feel of what is treated with them Affect textile material favorably.
Überraschenderweise wurde gefunden, daß diese Eigenschaften bes+ en monomeren Verbindungen bzw. den hieraus abgeleiteten Polymeren zu eigen sind. Diese neuen monomeren Verbindungen entsprechen der folgenden Formel Diese Verbindung kann durch Umsetzung von 3,3-Bis-(halogen)-oxetan mit Kaliumheptafluorisopropanolat hergestellt werden.Surprisingly, it has been found that these properties are specific to monomeric compounds or to the polymers derived therefrom. These new monomeric compounds correspond to the following formula This compound can be prepared by reacting 3,3-bis (halogen) oxetane with potassium heptafluoroisopropoxide.
Die Umsetzung kann in einem inerten aprotonischen Lösung mittel, wie z.B. Dimethylformamid, durchgeführt werden.The reaction can medium, such as in an inert aprotic solution e.g., dimethylformamide.
Weitere Beispiele geeigneter Lösungsmittel sind Acetonitril, Dimethyldiglykol, Tetramethylensulfon und Tetrahydrofuran.Further examples of suitable solvents are acetonitrile, dimethyl diglycol, Tetramethylene sulfone and tetrahydrofuran.
Als Halogen im Halogenmethyloxetan wird Chlor, Brom oder Jod verwendet. Außer Kaliumheptafluorisopropanolat eignet sich. auch das entsprechend Cäsiumheptafluorisopropanoliit.Chlorine, bromine or iodine are used as halogen in halomethyloxetane. Apart from potassium heptafluoroisopropoxide, it is also suitable. also the corresponding cesium heptafluoroisopropanolite.
Das erfindungsgemäße 3,3-Bis-(.heptafluorisopropoxymRthyl)-oxetan siedet bei 1870C/760 mm Hg. Das IR-Spektrum der monomeren Verbindungen ist gekennzeichnet durch starke Banden bei 1330, 1230, 1170, 1130, 1100, 1000, 730 cm und mittelstarke Banden bei 1480, 1465, 840 cm 1. Das Molgewicht beträgt 454. Die Verbindung stellt eine leicht bewegliche farblose Flüssigkeit dar. Sie hat bei 200C einen Brechungsindex von nD = 1,3228.The 3,3-bis (. Heptafluoroisopropoxymethyl) oxetane according to the invention boils at 1870C / 760 mm Hg. The IR spectrum of the monomeric compounds is indicated due to strong bands at 1330, 1230, 1170, 1130, 1100, 1000, 730 cm and medium strength Bands at 1480, 1465, 840 cm 1. The molecular weight is 454. The connection is an easily mobile colorless liquid. It has a refractive index at 200C of nD = 1.3228.
Die erfindungsgemäßen monomeren Verbindungen können mit sich oder mit anderen geeigneten Epoxiden olymerisiert werden.The monomeric compounds according to the invention can with themselves or be polymerized with other suitable epoxides.
Beispiele geeigneter Epoxide sind der aus der US-Patentschrift 3 361 685 bekannte Heptafluorisopropylglycidyläther oder das aus der deutschen Patentanmeldung P 20 59 013 bekannte 1,4-Bis-(heptafluorisopropoxy)-2,3-epoxybutan. Durch die Wahl des Comonomeren lassen sich die Eigenschaften de Polymerisats, auch in bezug auf den Griff, in gewisser Weise modifizieren.Examples of suitable epoxides are that described in US Pat. No. 3,361 685 known heptafluoroisopropyl glycidyl ether or that from the German patent application P 20 59 013 known 1,4-bis (heptafluoroisopropoxy) -2,3-epoxybutane. By choice of the comonomer can be the properties of the polymer, also with respect to modify the handle in some way.
Das monomere 3,3-Bis-theptafluorisopropoxymethyl)-ozetan kann auf textile Fasern aufgebracht und dort polymerisiert werden. Die erfindungsgemäße Verbindung kann dabei als reine Flüssigkeit oder in einem inerten Lösungsmittel gelöst auf die Faser aufgebracht werden. Das behandelte faserige Material wird dann gehärtet, z.B bei 50 bis 1500C während 5 bis 60 Minuten, um die Bindung des Monomeren an das faserige Material zu bewirken und die monomere Verbindung in situ zu polymerisieren. Hierbei wird einer der üblichen, vorstehend beschriebenen Polymerisationskatalysatoren verwendet und zweckmäßiy der Lösung des Monomeren bzw. dem reinen Monomeren zugesetzt.The monomeric 3,3-bis-theptafluorisopropoxymethyl) -ozetane can textile fibers are applied and polymerized there. The compound of the invention can be dissolved as a pure liquid or in an inert solvent the fiber can be applied. The treated fibrous material is then hardened, e.g. at 50 to 1500C during 5 to 60 minutes to bind the Monomers to effect the fibrous material and the monomeric compound in situ to polymerize. One of the conventional polymerization catalysts described above is used here used and expediently added to the solution of the monomer or the pure monomer.
Die Fixierung der erfindungsgemäßen monomeren Verbindungen auf der Faser kann durch Zusätze weiterer Verbindungen, wie z.B. Zirkonbutoxid und Dibutylzinndilaurat, verbessert wer den.The fixation of the monomeric compounds according to the invention on the By adding other compounds such as zirconium butoxide and dibutyltin dilaurate, fibers can be be improved.
Die erfindungsgemäßen Verbindungen können für alle Arten von faserigem Material verwendet werden, z.B. Wolle, Baumwolle, Polyester, Polyamid sowie Mischgewebe dieser Fasern. Das faserige Material kann dabei in Forn von losen Fasern, Fäden, Web- oder Strickwaren, Filzen oder fertigen Kleidungsstücken angewandt werden.The compounds according to the invention can be used for all types of fibrous Material can be used, e.g. wool, cotton, polyester, polyamide and mixed fabrics these fibers. The fibrous material can be in the form of loose fibers, threads, Woven or knitwear, felting or finished garments can be used.
Der Gegenstand vorliegender Erfindung soll durch das folgende Beispiel noch näher erläutert werden: Beispiel Darstellung des 3,3-Bis-(heptafluorisopropoxymethyl)-oxetans (1) Zur Synthese der Verbindung I wird 3,3-Bis-(halogemnethyl)-oxetan mit 2 Mol Kaliumheptafluorisopropanolat umgesetzt.The object of the present invention is illustrated by the following example to be explained in more detail: Example Preparation of 3,3-bis (heptafluoroisopropoxymethyl) oxetane (1) For the synthesis of the compound I is 3,3-bis (haloemnethyl) oxetane with 2 mol Potassium heptafluoroisopropoxide implemented.
Vorteilhafte Reaktionsgeschwindigkeit erhält man durch Verwendung von 3,3-Bis- (jodmethyl) -oxetan.Advantageous rate of reaction is obtained through use of 3,3-bis (iodomethyl) oxetane.
Kaliumheptafluorisopropanolat wird in bekannter Weise durch Einleiten von (CF3)2C=0 (332 g) in eine Suspension von KF (.127,2 g) in Dimethylformamid (600 ml) bei Raumtemperatur und unter feuchtigkeitsfreien Bedingungen hergestellt. Der klaren Lösung von Kaliumisopropanolat wird das 3,3-Bis-(jodmethyl)-oxetan (.308 g) zugegeben. Die Na.l-Abspaltung setzt sogleich ein. Die Reaktionstemperatur wird innerhalb von 3 Stunden auf 70 bis 750C gesteigert, dann läßt man weitere 15 Stunden bei dieser Temperatur nachreagieren.Potassium heptafluoroisopropoxide is introduced in a known manner of (CF3) 2C = 0 (332 g) in a suspension of KF (.127.2 g) in dimethylformamide (600 ml) at room temperature and under moisture-free conditions. Of the In a clear solution of potassium isopropoxide, 3,3-bis (iodomethyl) oxetane (.308 g) added. The splitting off of Na.l starts immediately. The reaction temperature becomes increased to 70 to 750 ° C. within 3 hours, then left for a further 15 hours post-react at this temperature.
Das ausgeschiedene Salz wird vom Reaktionsprodukt abgenutscht, dieses wäscht man dreimal mit H20, trocknet über Na2SC) und trennt das 3,3-Bis-(heptafluorisopropoxymethyl)-oxetan durch Kolonnendestillation ab (Siedepul .t 1870C/760 mm Hg, Brechungsindex nD = L,3228).The precipitated salt is filtered off with suction from the reaction product, this it is washed three times with H2O, dried over Na2SC) and the 3,3-bis (heptafluoroisopropoxymethyl) oxetane is separated by column distillation (boiling pulse .t 1870C / 760 mm Hg, refractive index nD = L, 3228).
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712116105 DE2116105A1 (en) | 1971-03-03 | 1971-03-03 | 3,3-bis-(heptafluoroisopropoxymethyl) oxetane - prepn from 3,3-bis-(halomethyl) oxetanes and heptafluoroisopropanolates and use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712116105 DE2116105A1 (en) | 1971-03-03 | 1971-03-03 | 3,3-bis-(heptafluoroisopropoxymethyl) oxetane - prepn from 3,3-bis-(halomethyl) oxetanes and heptafluoroisopropanolates and use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2116105A1 true DE2116105A1 (en) | 1972-09-07 |
Family
ID=5803678
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712116105 Pending DE2116105A1 (en) | 1971-03-03 | 1971-03-03 | 3,3-bis-(heptafluoroisopropoxymethyl) oxetane - prepn from 3,3-bis-(halomethyl) oxetanes and heptafluoroisopropanolates and use |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2116105A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0430887A3 (en) * | 1989-11-30 | 1991-11-13 | Ciba-Geigy Ag | Heteroatom containing 3,3-bis perfluoroalkyl oxetanes and polyethers therefrom |
| US5097067A (en) * | 1989-11-30 | 1992-03-17 | Ciba-Geigy Corporation | Carboxy acids derived from heteroatom containing 3,3-bis-perfluoroalkyl oxetanes |
-
1971
- 1971-03-03 DE DE19712116105 patent/DE2116105A1/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0430887A3 (en) * | 1989-11-30 | 1991-11-13 | Ciba-Geigy Ag | Heteroatom containing 3,3-bis perfluoroalkyl oxetanes and polyethers therefrom |
| US5097067A (en) * | 1989-11-30 | 1992-03-17 | Ciba-Geigy Corporation | Carboxy acids derived from heteroatom containing 3,3-bis-perfluoroalkyl oxetanes |
| US5097048A (en) * | 1989-11-30 | 1992-03-17 | Ciba-Geigy Corporation | Heteroatom containing 3,3-bis-perfluoroalkyl oxetanes and polyethers therefrom |
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