NO150683B - PERFLUORALLYCYL-SUBSTITUTED HALVES - OR AMIDE TENSIDES, EVEN IN THE FORM OF MIXTURES, AND USE THEREOF - Google Patents
PERFLUORALLYCYL-SUBSTITUTED HALVES - OR AMIDE TENSIDES, EVEN IN THE FORM OF MIXTURES, AND USE THEREOF Download PDFInfo
- Publication number
- NO150683B NO150683B NO784108A NO784108A NO150683B NO 150683 B NO150683 B NO 150683B NO 784108 A NO784108 A NO 784108A NO 784108 A NO784108 A NO 784108A NO 150683 B NO150683 B NO 150683B
- Authority
- NO
- Norway
- Prior art keywords
- carbon atoms
- oxide
- molecular weight
- perfluoroalkyl
- formula
- Prior art date
Links
- 239000004094 surface-active agent Substances 0.000 title claims description 18
- 239000000203 mixture Substances 0.000 title claims description 14
- 150000001408 amides Chemical class 0.000 title claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- -1 polysiloxane Polymers 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 20
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 14
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 150000002009 diols Chemical class 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 229920001296 polysiloxane Polymers 0.000 claims description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
- 239000005977 Ethylene Substances 0.000 claims description 5
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 5
- 238000009826 distribution Methods 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 229920000728 polyester Polymers 0.000 claims description 5
- 229920000570 polyether Polymers 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
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- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
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- 229920000573 polyethylene Polymers 0.000 claims 1
- 239000000654 additive Substances 0.000 description 16
- 230000000996 additive effect Effects 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 13
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000004909 Moisturizer Substances 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
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- 238000004519 manufacturing process Methods 0.000 description 7
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
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- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
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- 238000004458 analytical method Methods 0.000 description 3
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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- 125000003277 amino group Chemical group 0.000 description 2
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- 239000004009 herbicide Substances 0.000 description 2
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 2
- 239000012943 hotmelt Substances 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
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- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical class OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
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- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ZQHJVIHCDHJVII-OWOJBTEDSA-N (e)-2-chlorobut-2-enedioic acid Chemical class OC(=O)\C=C(\Cl)C(O)=O ZQHJVIHCDHJVII-OWOJBTEDSA-N 0.000 description 1
- FIXBBOOKVFTUMJ-UHFFFAOYSA-N 1-(2-aminopropoxy)propan-2-amine Chemical class CC(N)COCC(C)N FIXBBOOKVFTUMJ-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
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- PMVSDNDAUGGCCE-TYYBGVCCSA-L Ferrous fumarate Chemical compound [Fe+2].[O-]C(=O)\C=C\C([O-])=O PMVSDNDAUGGCCE-TYYBGVCCSA-L 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
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- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
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- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
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- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
- B23K—SOLDERING OR UNSOLDERING; WELDING; CLADDING OR PLATING BY SOLDERING OR WELDING; CUTTING BY APPLYING HEAT LOCALLY, e.g. FLAME CUTTING; WORKING BY LASER BEAM
- B23K35/00—Rods, electrodes, materials, or media, for use in soldering, welding, or cutting
- B23K35/22—Rods, electrodes, materials, or media, for use in soldering, welding, or cutting characterised by the composition or nature of the material
- B23K35/36—Selection of non-metallic compositions, e.g. coatings, fluxes; Selection of soldering or welding materials, conjoint with selection of non-metallic compositions, both selections being of interest
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Description
I US-patent nr. 3.621^059 omtales amider avledet fra heksa-fluorpropylenoksydpolymersyrer og polyalkylenoksyder med In US patent no. 3,621^059, amides derived from hexafluoropropylene oxide polymeric acids and polyalkylene oxides with
hvori R¥ betyr et perfluoralkylradikal med et til atte karbonatomer, n er et helt tall mellom 0 og 100, R er et alkylen-radikal med 2 til 12 karbonatomer, R 2betyr hydrogen eller et alkylradikal med 1 til 4 karbonatomer, R? er hydrogen eller et alkylradikal med 1 til 4 karbonatomer, i det minste 2 3 en av R og R i hver gjentagende enhet er hydrogen, y er et helt tall fra 1 til 60, R 4 betyr hydrogen eller et alkylradikal med 1 til 4 karbonatomer, og R^ er hydrogen eller et alkylradikal med 1 til 6 karbonatomer. Disse amider virker effektivt som overflateaktive midler og emulgeringsmidler. Alle disse overflateaktive midler er avledet fra heksafluorpropylenoksyd. I US-patent nr. 2.915.554 omtales perfluoralkansulfonamider med formel hvori R, betyr en perfluoralkylgruppe med fra 4 til 12 karbonatomer, R 6er valgt fra gruppen bestående av hydrogen og lavere-alkylradikaler, og R^ og R^ er en polyoksyalkylgruppe med formel in which R¥ means a perfluoroalkyl radical with one to eight carbon atoms, n is an integer between 0 and 100, R is an alkylene radical with 2 to 12 carbon atoms, R 2 means hydrogen or an alkyl radical with 1 to 4 carbon atoms, R? is hydrogen or an alkyl radical of 1 to 4 carbon atoms, at least 2 3 one of R and R in each repeating unit is hydrogen, y is an integer from 1 to 60, R 4 means hydrogen or an alkyl radical of 1 to 4 carbon atoms , and R 1 is hydrogen or an alkyl radical of 1 to 6 carbon atoms. These amides act effectively as surfactants and emulsifiers. All these surfactants are derived from hexafluoropropylene oxide. US patent no. 2,915,554 mentions perfluoroalkanesulfonamides of the formula in which R, means a perfluoroalkyl group with from 4 to 12 carbon atoms, R 6 is selected from the group consisting of hydrogen and lower alkyl radicals, and R^ and R^ are a polyoxyalkyl group of the formula
hvori m er et helt tall fra 2 til 3, n er et tall fra 2 til ca. 20, og hver R" er hydrogen eller et metylradikal. where m is an integer from 2 to 3, n is a number from 2 to approx. 20, and each R" is hydrogen or a methyl radical.
Disse sulfonamider virker som overflateaktive midler. Nærværet av en SC^-gruppe er nødvendig i alle tilfelle. These sulfonamides act as surfactants. The presence of an SC^ group is required in all cases.
Andre ikke-ioniske fluorkjemiske overflateaktive midler er omtalt i BRD off. skrifter nr. 2.215.388 og 2.261.681. Other non-ionic fluorochemical surfactants are discussed in BRD off. documents no. 2,215,388 and 2,261,681.
Det er nu funnet at en stor mengde anvendelige ikke-ioniske-fluorerte overflateaktive midler lett kan fremstilles uten nødvendighet av en alkyleringsreaksjon og uten nødvendighet for fremstilling av en perfluoralkylsubstituert syre som mellom-produkt, ved basekatalysert tilsetning av en Rf-substituert tiol til malein- eller fumarhalvester eller -halvamid inneholdende en hydrokarbon-, polyetylenoksyd- eller polysiloksan-gruppe i esteren eller amiddelen. Det er en ytterligere for-del som bidrar til overlegenheten av disse nye forbindelser, It has now been found that a large amount of useful non-ionic fluorinated surfactants can be easily prepared without the necessity of an alkylation reaction and without the necessity for the preparation of a perfluoroalkyl-substituted acid as an intermediate, by the base-catalyzed addition of an Rf-substituted thiol to malein- or fumar half ester or half amide containing a hydrocarbon, polyethylene oxide or polysiloxane group in the ester or amide. There is a further advantage that contributes to the superiority of these new compounds,
at de kan spesielt fremstilles for spesifikke systemer, dvs. deres forenlighet med et gitt system, enten vandig eller or-ganisk, kan optimaliseres, og selv strukturelle elementer kan tilpasses ved å velge egnede ikke-ioniske derivater for syntesen. that they can be specially prepared for specific systems, i.e. their compatibility with a given system, whether aqueous or organic, can be optimized, and even structural elements can be adapted by choosing suitable non-ionic derivatives for the synthesis.
Fremstillingen av disse nye overflateaktive midler utføres The production of these new surfactants is carried out
i to trinn: Det første innbefatter den ring-åpnende reaksjon av maleinsyreanhydrid med et polyeter-, polyesterdiol-, diamin-eller polysiloksanderivat som enten kan være en alkohol eller et primært amin (og kan også inneholde hydrofobe segmenter som alifatiske eller aromatiske hydrokarbongrupper eller poly-propylenoksydsegmenter). Annet trinn omfatter en basekatalysert addisjon av en perfluoralkylsubstituert tiol til malein-dobbelt-bindingen, utført i et egnet oppløsningsmiddel eller i masse. in two steps: The first involves the ring-opening reaction of maleic anhydride with a polyether, polyesterdiol, diamine or polysiloxane derivative which can be either an alcohol or a primary amine (and can also contain hydrophobic segments such as aliphatic or aromatic hydrocarbon groups or poly -propylene oxide segments). The second step comprises a base-catalyzed addition of a perfluoroalkyl-substituted thiol to the maleic double bond, carried out in a suitable solvent or in bulk.
De nye overflateaktive midler inneholder en karboksylgruppe og er oppløselig i fortynnet mineralsyreoppløsninger og oppfører seg deri som ikke-ioniske overflateaktive midler. Ved basisk pH bidrar karboksylgruppene til å øke oppløseligheten. The new surface-active agents contain a carboxyl group and are soluble in dilute mineral acid solutions and behave there as non-ionic surface-active agents. At basic pH, the carboxyl groups help to increase solubility.
Oppfinnelsen vedrører perfluoralkylsubstituerte halvester-og amid-tensider, eventuelt i form av blandinger, idet tensidene er karakterisert ved at de har formel The invention relates to perfluoroalkyl-substituted half-ester and amide surfactants, possibly in the form of mixtures, the surfactants being characterized by having the formula
hvori Rf betyr rettlinjet eller forgrenet perfluoralkyl med 4 til 18 karbonatomer eller perfluoralkyl substituert med per- in which Rf means straight or branched perfluoroalkyl of 4 to 18 carbon atoms or perfluoroalkyl substituted with per-
fluoralkoksy med 2 til 6 karbonatomer, ^ er forgrenet eller rettlinjet alkylen med 1 til 12 karbonatomer, alkylentio- fluoroalkoxy with 2 to 6 carbon atoms, ^ is branched or straight alkylene with 1 to 12 carbon atoms, alkylenethio-
alkylen med 2 til 12 karbonatomer, alkylenoksyalkylen med 2 til 12 karbonatomer eller alkyleniminoalkylen med 2 til 12 karbonatomer hvor nitrogenatomet har som tredje substituent hydrogen the alkylene with 2 to 12 carbon atoms, the alkyleneoxyalkylene with 2 to 12 carbon atoms or the alkyleneiminoalkylene with 2 to 12 carbon atoms where the nitrogen atom has hydrogen as the third substituent
■eller alkyl med 1 til 6 karbonatomer, X betyr oksygen eller NH, ■or alkyl with 1 to 6 carbon atoms, X means oxygen or NH,
y betyr 1 eller null, Q er et toverdig polyeter- eller polyester-radikal med en molekylvekt på 300 til 5000 eller et polysiloksan med 5 til 80 tilbakevendende enheter, og A betyr hydrogen, hydroksyl, alkoksy med 1 til 21 karbonatomer, fenoksy, alkylfenoksy med 7 til 24 karbonatomer, gruppen y means 1 or zero, Q is a divalent polyether or polyester radical with a molecular weight of 300 to 5000 or a polysiloxane with 5 to 80 repeating units, and A means hydrogen, hydroxyl, alkoxy of 1 to 21 carbon atoms, phenoxy, alkylphenoxy with 7 to 24 carbon atoms, the group
hvori Rj;, R^, X og y har overnevnte betydning. in which Rj;, R^, X and y have the above meaning.
Fenoksyradikalet (A) kan inneholde en eller flere enn en alkyl-substituent, og er f. eks. metylfenoksy, oktylfenoksy, nonyl-fenoksy eller dinonylfenoksy. The phenoxy radical (A) may contain one or more than one alkyl substituent, and is e.g. methylphenoxy, octylphenoxy, nonylphenoxy or dinonylphenoxy.
Oppfinnelsen vedrører også anvendelsen av disse forbindelser som overflateaktive midler. The invention also relates to the use of these compounds as surfactants.
Fortrinnsvis er R^ en rettlinjet eller forgrenet perfluoralkylen-kjede med 4, fortrinnsvis 6 til 12 karbonatomer, R^ alkylen med 1 til 6 karbonatomer og fortrinnsvis etylen, y betyr 0, Q et polyoksyalkylenoksyd med fra 10 til 50 tilbakevendende enheter som polyetylenoksyd, A hydroksyl, metoksy eller alkylfenoksy med 7 til 24 karbonatomer, og X betyr -0- eller -NH--fortrinnsvis -0-. Preferably R^ is a straight or branched perfluoroalkylene chain with 4, preferably 6 to 12 carbon atoms, R^ the alkylene with 1 to 6 carbon atoms and preferably ethylene, y means 0, Q a polyoxyalkylene oxide with from 10 to 50 repeating units such as polyethylene oxide, A hydroxyl, methoxy or alkylphenoxy with 7 to 24 carbon atoms, and X means -0- or -NH--preferably -0-.
Forbindelsen ifølge oppfinnelsen kan vanligvis fremstilles ved en to-trinns fremgangsmåte. Første trinn består av en kordensasjons-reaksjon av en alkohol, diol, amin eller et diamin med formel The compound according to the invention can usually be prepared by a two-step process. The first step consists of a co-condensation reaction of an alcohol, diol, amine or a diamine of formula
A-Q-X-H, hvori A, Q og X har ovennevnte betydning med malein-eller itakonanhydrid for å gi mellomprodukter med formel A-Q-X-H, wherein A, Q and X are as defined above with maleic or itaconic anhydride to give intermediates of formula
Nevnte mellomprodukter kan også fremstilles ved transforestring med lavere-alkylestere av malein-, fumar- eller itakonestere som mono- og dimetylestere av malein-, fumar- eller itakon-syrer. Det mest anvendelige utgangsmaterial for mellompro-duktene med formel (6) er maleinsyreanhydrid. Metyl-malein-syre og klormaleinsyrederivater kan benyttes ved fremstillingen, men gir upraktiske lave utbytter av det ønskede sluttprodukt. Said intermediates can also be prepared by transesterification with lower alkyl esters of maleic, fumaric or itaconic acids such as mono- and dimethyl esters of maleic, fumaric or itaconic acids. The most applicable starting material for the intermediate products with formula (6) is maleic anhydride. Methyl-maleic acid and chloromaleic acid derivatives can be used in the preparation, but give impractically low yields of the desired end product.
I annet trinn utføres en basekatalysert addisjonsreaksjon av et perfluoralkylalkylentiol med formel R^-R^-SH og et mellompro-dukt med formel (6) eller (7) dannes. In the second step, a base-catalyzed addition reaction of a perfluoroalkylalkylenethiol of formula R^-R^-SH is carried out and an intermediate product of formula (6) or (7) is formed.
Gruppen Q er et polyeter-, polyester- eller siloksandiradikal. Følgende er illustrative eksempler på polyeterdiradikaler: The group Q is a polyether, polyester or siloxane radical. The following are illustrative examples of polyether diradicals:
Eksempler på polyester-dioldiradikaler er de avledet fra disyrer og dioler, for eksempel alkylenglykolpolyadipat, poly-sebacat, polyisoftalat, polyortoftalat, polytereftalat, poly-maleat, polyglutarat og lignende, slike polyesterdioler kan være baser på en blanding av flere dioler og disyrer og er kommersielt tilgjengelige for fremstilling av polyuretan-pre-polymerer i et molekylvektområde fra 400 til 5000. Examples of polyester diol dialkyls are those derived from diacids and diols, for example alkylene glycol polyadipate, poly-sebacate, polyisophthalate, polyorthophthalate, polyterephthalate, poly-maleate, polyglutarate and the like, such polyester diols can be bases on a mixture of several diols and diacids and are commercially available for the production of polyurethane pre-polymers in a molecular weight range from 400 to 5000.
Eksempler på polysiloksaner er slike med formel Examples of polysiloxanes are those with formula
Eksempler på alkoholer, dioler og aminer anvendelig ved fremstilling av mellomprodukter (6) og (7) er angitt neden- Examples of alcohols, diols and amines applicable in the production of intermediates (6) and (7) are indicated below
for : for :
polyetylenoksyd, molekylvekt 200-500, fortrinnsvis 400- polyethylene oxide, molecular weight 200-500, preferably 400-
2000, 2000,
- polypropylenoksyd, molekylvekt 200-5000, fortrinnsvis 400-2000, - metoksypolyetylenoksyd, molekylvekt 4 00-25 000, fortrinnsvis 400-2000, - polytetrametylenoksyd, molekylvekt 3000- 6000, - polypropylene oxide, molecular weight 200-5000, preferably 400-2000, - methoxy polyethylene oxide, molecular weight 400-25000, preferably 400-2000, - polytetramethylene oxide, molecular weight 3000-6000,
poly(etylen-ko-propylenoksyd) blokk-polyerer som polypropoksy-(10-50 tilbakevendende enheter)-bispolyetoksy-(10-20) diol eller polyetoksy-(10-50)-bis-polypropoksy (10-50)-diol, poly(ethylene-co-propylene oxide) block polymers such as polypropoxy-(10-50 repeating units)-bispolyethoxy-(10-20) diol or polyethoxy-(10-50)-bis-polypropoxy (10-50)-diol,
etoksylert alkylfenol hvor alkyl er oktyl eller nonyl og den etoksylerte gruppe inneholder fra 5 til 50 etylenoksydenheter, ethoxylated alkylphenol where alkyl is octyl or nonyl and the ethoxylated group contains from 5 to 50 ethylene oxide units,
etoksylerte primære og sekundære aminer med 7 til 20 karbonatomer, ethoxylated primary and secondary amines of 7 to 20 carbon atoms,
etoksylerte fettsyrer og amider med 8 til 2 0 karbonatomer, ethoxylated fatty acids and amides with 8 to 20 carbon atoms,
alkoksylerte alkoholer og dioler med 8 til 20 karbonatomer, bis(2-amino-propyl(etere av polyetylenoksyd og polypropylenoksyd , Alkoxylated alcohols and diols with 8 to 20 carbon atoms, bis(2-amino-propyl) ethers of polyethylene oxide and polypropylene oxide,
siloksandioler og -trioler, etoksylerte merkaptogrupper med siloxanediols and -triols, ethoxylated mercapto groups with
8 til 20 karbonatomer. 8 to 20 carbon atoms.
Perfluoralkyltiolene anvendt i fremstilling av forbindelsene i-følge oppfinnelsen er velkjente. Eksempelvis er tioler med formel Rf-R -SH omtalt i et antall US-patenter innbefattende 2.894.991, 2.961.470, 2.965.677, 3.088.849, 3.172.190, 3.544.663 og 3.655.732. The perfluoroalkyl thiols used in the preparation of the compounds according to the invention are well known. For example, thiols with the formula Rf-R-SH are mentioned in a number of US patents including 2,894,991, 2,961,470, 2,965,677, 3,088,849, 3,172,190, 3,544,663 and 3,655,732.
Således vedrører US-patent nr. 3.655.732 merkaptaner med formel Thus, US Patent No. 3,655,732 relates to mercaptans of formula
hvor where
Ri betyr alkylen med 1 til 16 karbonatomer og Rf betyr perfluoralkyl og det angis at halogenider av formel R^-R 1-hal er velkjente, reaksjonen med R^I med etylen under fri-radikal-betingelser gir Rf (CI^CI^) I / mens omsetning av R^CI^I med etylen gir R^CH_(CH_CH„) I som omtales i US-patent nr. 3.088 Ri means the alkylene with 1 to 16 carbon atoms and Rf means perfluoroalkyl and it is stated that halides of the formula R^-R 1-hal are well known, the reaction of R^I with ethylene under free-radical conditions gives Rf (CI^CI^) I / while reaction of R^CI^I with ethylene gives R^CH_(CH_CH„) I which is mentioned in US Patent No. 3,088
r a £ £. a r a £ £. a
849, 3.145.222, 2.965.659 og 2.972.638. 849, 3,145,222, 2,965,659 and 2,972,638.
US-patent nr. 3.655.732 angir videre forbindelser med formel US Patent No. 3,655,732 further discloses compounds of formula
hvori in which
R og R er alkylen med 1 til 16 karbonatomer, idet summen av karbonatomene R og R ikke er større enn 25, Rf er perfluoralkyl med 4 til 14 karbonatomer og X er -S- eller NR"'-hvor R'" er hydrogen eller alkyl med 1 til 4 karbonatomer. R and R are the alkylene of 1 to 16 carbon atoms, the sum of the carbon atoms R and R not being greater than 25, Rf is perfluoroalkyl of 4 to 14 carbon atoms and X is -S- or NR"'-where R'" is hydrogen or alkyl of 1 to 4 carbon atoms.
Ifølge US-patent 3.544.663 angis at merkaptanene med formel According to US patent 3,544,663 it is stated that the mercaptans with formula
hvor where
R^ er perfluoralkyl med 5 til 13 karbonatomer, kan fremstilles ved omsetning av perfluoralkylalkylenjodid med tiourinstoff eller ved addering H2S til perfluoralkylsubstituert etylen (Rf-CI^CI^), som igjen kan fremstilles ved dehydrohalogenering av halogenidet Rf-CH2CH2-hal. R^ is perfluoroalkyl with 5 to 13 carbon atoms, can be prepared by reacting perfluoroalkylalkylene iodide with thiourea or by adding H2S to perfluoroalkyl-substituted ethylene (Rf-CI^CI^), which in turn can be prepared by dehydrohalogenation of the halide Rf-CH2CH2-hal.
Omsetningen av jodidet R^-R^-I med tiourinstoff etterfulgt av hydrolyse for å danne merkaptanet R^-R -DH er den foretrukne syntetiske vei. Reaksjonen er anvendelig både for rettlinjede og forgrenede kjeders jodider. Mange anvendelige perfluor-alkoksyalkyljodider omtales i US-patent 3.514.487 med den generelle formel Spesielt foretrukket her er tioler med formel The reaction of the iodide R^-R^-I with thiourea followed by hydrolysis to form the mercaptan R^-R-DH is the preferred synthetic route. The reaction is applicable to both linear and branched chain iodides. Many applicable perfluoro-alkoxyalkyl iodides are described in US patent 3,514,487 with the general formula Particularly preferred here are thiols with the formula
hvor where
Rf er perfluoralkyl med 6 til 12 karbonatomer. Rf is perfluoroalkyl of 6 to 12 carbon atoms.
Disse Rf-tioler kan fremstilles fra RfCH2CH2I og tiourinstoff These Rf thiols can be prepared from RfCH2CH2I and thiourea
i meget høyt utbytte. in very high yield.
Anskueliggjørende eksempler på foretrukne perfluoralkylalkylentioler er: Spesielt foretrukket perfluoralkylalkylentioler er Illustrative examples of preferred perfluoroalkylalkylenethiols are: Particularly preferred perfluoroalkylalkylenethiols are
og blandinger herav. and mixtures thereof.
Fremstillingen av de nye ikke-ioniske overflateaktive forbindelser utføres vanligvis i to trinn, idet første trinn omfatter omsetningen av det cykliske anhydrid, vanligvis malein-anhydrid, med hydroksy- eller aminosubstituerte ikke-ionisk forbindelse enten i masse eller i et felles tørt og aprotisk oppløsningsmiddel, idet det anvendelige oppløsningsmiddel in-befatter ketoner er, som aceton og metylenketon, etere som dietyleter eller etylenglykol-dimetyleter, eller tetrahydro-furan, estere, som etylacetat eller metylcellosolvacetat, amider som dimetylformamid eller N-metylpyrrolidon. Mens aminer reagerer hurtig ved værelsestemperatur, må hydroksy-forbindelser oppvarmes flere timer til 50 - 100°C. Annet trinn innbefatter tilsetning av perfluoralkylalkylentiolet til det mellomdannende maleinhalvester eller halvamid i nærvær av basisk katalysator:, som trietylamin, pyridin eller tetrametyl-ammoniumhydroksyd. Tilsetning av tioler til blandingen fører ofte til heterogent 2-fasesystem, som vil gå over i en homogen oppløsning når reaksjonen skrider frem. Dette reaksjonstrinn utføres vanligvis mellom 30 og 75°C og under nitrogen og med god omrøring. The production of the new non-ionic surface-active compounds is usually carried out in two steps, the first step comprising the reaction of the cyclic anhydride, usually maleic anhydride, with a hydroxy- or amino-substituted non-ionic compound either in bulk or in a common dry and aprotic solvent , as the applicable solvent includes ketones, such as acetone and methylene ketone, ethers such as diethyl ether or ethylene glycol dimethyl ether, or tetrahydrofuran, esters, such as ethyl acetate or methylcellosolv acetate, amides such as dimethylformamide or N-methylpyrrolidone. While amines react quickly at room temperature, hydroxy compounds must be heated for several hours to 50 - 100°C. Another step involves adding the perfluoroalkylalkylenethiol to the intermediate maleic ester or semiamide in the presence of a basic catalyst: such as triethylamine, pyridine or tetramethylammonium hydroxide. Addition of thiols to the mixture often leads to a heterogeneous 2-phase system, which will turn into a homogeneous solution as the reaction progresses. This reaction step is usually carried out between 30 and 75°C and under nitrogen and with good stirring.
Forbindelsene ifølge oppfinnelsen kan også fremstilles ved å rever-sere rekkefølgen av reaksjonen angitt ovenfor, det vil si, først utføre den basisk katalyserte addisjon av perfluorsubstitiaerte tioler til maleinsyreanhydrid etterfulgt av ringåpning med hydroksy- eller aminosubstituerte ikke-ionisk forbindelse. The compounds according to the invention can also be prepared by reversing the order of the reaction indicated above, that is, first performing the base-catalyzed addition of perfluorosubstituted thiols to maleic anhydride followed by ring opening with a hydroxy- or amino-substituted non-ionic compound.
Slike fluorkjemiske overflateaktive midler er anvendelig til Such fluorochemical surfactants are useful for
å forbedre eller å tildele egenskaper som : fukting, inntreg-ning, spredning, utjevning, skumstabilitet, strømningsegenskaper, emulgering, dispergering, og olje- og vannavstøtning. Basert på disse gode egenskaper er forskjellige anvendelser, hvorav noen vil omtales. to improve or to assign properties such as: wetting, penetration, dispersion, leveling, foam stability, flow properties, emulsification, dispersion, and oil and water repellency. Based on these good properties are different applications, some of which will be discussed.
Plast- og gummi- industri Plastic and rubber industry
Emulgeringsmidler for polymerisering, spesielt av fluor-monomerer. Emulsifiers for polymerization, especially of fluorine monomers.
- Som lateksstabilisator. - As a latex stabilizer.
- For hjelp til fremstilling av agglomerater av pulveriserte f luorkarbonpolymerer. - I synergistiske blandinger med hydrokarbon-overflateaktive midler til å fukte lavenergioverflater innbefattende naturlig og syntetisk kautsjuk, harpiks, plast. - Som tilsetning for skumanvendelser og skummemidler til hjelp ved påvisning av lekkasjer. - Som skumtilsetning for å kontrollere spredning, stigning, kantoppbygning. - For help in the production of agglomerates of powdered fluorocarbon polymers. - In synergistic mixtures with hydrocarbon surfactants to wet low energy surfaces including natural and synthetic rubber, resins, plastics. - As an additive for foam applications and foaming agents to help detect leaks. - As a foam additive to control spreading, rise, edge build-up.
Som formfrigjøringsmidler for silikoner, etc. As mold release agents for silicones, etc.
I ildfaste prosesser. In refractory processes.
Som en anti-tåke filmdanner. As an anti-fog film former.
Tilsetninger for eliminering av innesluttet luft i plast-laminater. Additives for eliminating trapped air in plastic laminates.
Fuktemiddel for hapiksformer. Moisturizer for hapik forms.
Varm-smeltetilsetning for olje- og fettavstøtning. Hot-melt additive for oil and grease repellence.
Harpikstilsetning for forbedret fukting og binding med fyll-stoff . - Strømningsmodifisering for ekstrudering av varme smelter, spredning, jevnhet., anti-kraterdannelse. Resin addition for improved wetting and binding with filler. - Flow modification for extrusion of hot melts, dispersion, uniformity., anti-cratering.
Tilsetning for harpiks-etsereagens. Additive for resin etchant.
Formfrigjøringsmiddel, avformingsmiddel. Mold release agent, release agent.
Retarderer for migrering eller fordamping av plast-myknere. Retardant for migration or evaporation of plastic softeners.
- Indre antistatisk middel for polyolefiner. - Internal antistatic agent for polyolefins.
- Antiblokkemiddel for polyolefiner. - Anti-blocking agent for polyolefins.
Petroleumsindustrien The petroleum industry
- Som en filmfordampnings-inhiMtor fQr bensin, jet-drivstoff, oppløsningsmidler, hydrokarboner. - As a film evaporation inhibitor for gasoline, jet fuel, solvents, hydrocarbons.
I ekstreme press- og smøremidler. In extreme pressure and lubricants.
Tekstil- og lærindustrier Textile and leather industries
Smussfrigjørende og smussavstøtende middel. Dirt-releasing and dirt-repellent agent.
- 01je/vann-avstøtende tekstil- og lærbehandling. - 01je/water-repellent textile and leather treatment.
- Fuktemiddel for å forbedre dekning og penetrering av - Moisturizer to improve coverage and penetration of
porer i substrater. pores in substrates.
- Anti-skummiddel i tekstilbehandlingsbad. - Anti-foam agent in textile treatment bath.
- Fuktemiddel for jevnhet av finish på garn. - Moisturizer for uniformity of finish on yarn.
- Penetreringsmiddel for finish på tau, tungdeniere-fibre. - Penetrant for finishing ropes, heavy denier fibres.
- Emulgeringsmiddel/smøremiddel/for fiberfinish. - Emulsifier/lubricant/for fiber finish.
- Rensemiddel/metallbehandlingsmiddel for polymerisasjons-utstyr. - Cleaning agent/metal treatment agent for polymerization equipment.
Strømningsmodif iserer for spinning av varmsruelter, oppløs-ninger . - Tilsetningsmiddel for tekstilappretur for jevn fordeling. Flow modifier for the spinning of hot rollers, solutions. - Textile finishing additive for even distribution.
Fuktemiddel for farvning. Moisturizer for dyeing.
- Penetreringshjelpemiddel for bleking. - Penetration aid for bleaching.
Fuktemiddel for bindemidler i ikke-vevede tekstiler. Wetting agent for binders in non-woven textiles.
Maling-, pigment- og finishing- industrier Paint, pigment and finishing industries
Utjevningsmiddel, anti-kratertilsetning for finish og maling.. Leveling agent, anti-crater additive for finish and paint..
- Tilsetning for kontroll av tilsmussing. - Additive to control soiling.
- Middel til å kontrollere forskjell i fordampning av oppløs-ningsmidler. - Means for controlling differences in evaporation of solvents.
- Utjevningsmiddel for gulvvoks. - Leveling agent for floor wax.
- Tilsetning til voks for å forbedre olje- og vannavstøtning. - Addition to wax to improve oil and water repellency.
Adhesjonsforbedrer for oljeaktige eller fettede overflater. Adhesion improver for oily or greasy surfaces.
- For å bekjempe pigmentfIotasjonsproblemer. - To combat pigment flotation problems.
- Forbedrer av finish av billakk, basert på vann-basert belegg hvori pigmentene er gjort ikke-reaktive. - Improves the finish of car paint, based on a water-based coating in which the pigments are made non-reactive.
Pigmentmalemiddel for å bevirke fuktning, dispergering, farve-fremkalling. - Skumfrembringningsstoff ved påføring av farver, blekk. Pigment coloring agent to effect wetting, dispersing, color development. - Foaming agent when applying colours, inks.
Elektrolyttiske omformningsbelegg. Electrolytic reshaping coatings.
Bergverk og metallbearbeidende industrier Mining and metalworking industries
- I rensemidler for forbedring av egenskaper. - In cleaning agents to improve properties.
- Tilsetning ved rensing med oppløsningsmidler. - Addition when cleaning with solvents.
- Tilsetning for metallpiklingsbad for å øke badets levetid og surhet. - Tilsetning for krom-elektroplettering, nedsettelse av overflate- - Additive for metal pickling baths to increase the life and acidity of the bath. - Additive for chrome electroplating, reduction of surface
spenning og skumming. tension and foaming.
- Tilsetning til loddepasta, spesielt for elektroniske kretser. - Additive to solder paste, especially for electronic circuits.
- Beskyttelsesmiddel for belegg (mattingsmotstandsevne, fett-avstøtning). - Protective agent for coatings (matting resistance, grease repellency).
Korrosjonsinhibitor. Corrosion inhibitor.
Tilsetning for etseoppløsninger for forbedret definisjon. Additive for etching solutions for improved definition.
Plastikpreplate- og silikonetseteknologi. Plastic preplate and silicone etching technology.
I loddepasta for mikroelektronikk for å redusere skumming. In solder paste for microelectronics to reduce foaming.
I kjemisk ruemiddeloppløsning, for galvanisering. In chemical embrittlement solution, for galvanizing.
Som et kolloidalt dispergeringshjelpemiddel for magnetiske As a colloidal dispersing aid for magnetic
faste stoffer. solid substances.
- Beskyttende belegg for aluminium og som anti-blokkemiddel. - Protective coating for aluminum and as an anti-blocking agent.
Fuktemiddel for lutning av kobbermalm og som friskt Moisturizer for the slope of copper ore and as fresh
flottasjonsmiddel. flotation agent.
For å bevirke avfuktning og hurtigere brytning av det beskyttende oksydlag. To effect dehumidification and faster breaking of the protective oxide layer.
Farmasøytisk industri Pharmaceutical industry
Forbedring av egenskaper for og penetrering av anti-mikro-bielle midler. Improving the properties and penetration of anti-microbial agents.
Forbedring av egenskaper for biokjemikalier, biocider, algi-cider, baktericider og bakteriostater. Improvement of properties for biochemicals, biocides, algicides, bactericides and bacteriostats.
Forbedring av styrke, homogenitet, og reduksjon av perme-abiliteten av innkapslede materialer. Improvement of strength, homogeneity, and reduction of the permeability of encapsulated materials.
- Emulgering av fluorkjemiske bloderstatninger. - Emulsification of fluorochemical blood substitutes.
Jordbruk og skogbruk Agriculture and forestry
- Fuktemiddel for herbicider, fungicider, ugressmidler, hormon-vekst-regulatorer, parasiticider, insekticider, germicider, baktericider, nematocider, mikrobicider, av-løvningsmidler og gjødningsmiddel. - Som bestanddel i kjemosteriliseringsmidler, insektfrastøtnings-midler og toksiske midler. - Wetting agent for herbicides, fungicides, herbicides, hormone-growth regulators, parasiticides, insecticides, germicides, bactericides, nematocides, microbicides, defoliants and fertilisers. - As a component in chemosterilizing agents, insect repellents and toxic agents.
- For fuktbare pulver-pesticider og kjemiske pulvere. - For wettable powder pesticides and chemical powders.
- Korrosjonsinhibitor for kjemiske midler. - Corrosion inhibitor for chemical agents.
- Fuktemiddel for løv. - Moisturizer for leaves.
- Fuktemiddel for kveg-vask, eller for å fukte fåreskinn under desalinering. - Moisturizer for cattle washing, or to moisten sheepskin during desalination.
Fuktetilsningsmiddel for fremstilling av kryssfiner. Humectant for the production of plywood.
- Penetreringsmiddel for preserverende impregnering. - Penetrant for preservative impregnation.
Tremasse-hjelpemiddel. Wood pulp aid.
For rensning av rør ved papirfremstilling, farving. For cleaning pipes in papermaking, dyeing.
- Fett/oljeavviser for papir. - Grease/oil repellent for paper.
Ild- bekjempelse Fire fighting
Fuktemiddel for å bekjempe skogbranner. Humectant to fight forest fires.
- Middel i vandig film dannende skum, brannslokkende midler. - Agent in aqueous film forming foam, fire extinguishing agents.
Komponent i fluorproteinskum. Component in fluoroprotein foam.
Tilsetning til tørre kjemiske slukkemidler. Addition to dry chemical extinguishing agents.
Middel i aerosol-slukkere. Agent in aerosol extinguishers.
Fuktemiddel for sprinkelvann. Humectant for sprinkler water.
Bilindustri, byggvedlikehold og rensing Automotive industry, building maintenance and cleaning
Fuktemiddel for rensemiddelblandinger. Moisturizer for cleaning agent mixtures.
Tilsetning for alkaliske rensemidler. Additive for alkaline cleaning agents.
- Glassrenser. - Glass cleaner.
Fuktemiddel for automobilvoks. Moisturizer for automotive wax.
- Tilsetning for å forbedre olje/vannavstøtning av voks. - Addition to improve oil/water repellency of wax.
Smøremiddel/korrosjonsinhibitor for antifrysemiddel. Lubricant/corrosion inhibitor for antifreeze.
Skyllemiddel for bilvask. Rinse aid for car washing.
- Tørr-renseblandinger og oppløsningsrensemidler for vanner-statning og skumming. Kan forbedre smuss- og suspensjonen og nedsette avsetning på nytt. - Dry cleaning mixtures and solvent cleaning agents for water replacement and foaming. Can improve dirt and suspension and reduce deposition again.
Skummiddel for rør-rensing. Foaming agent for pipe cleaning.
Anti-tåkefilmskummer for glass og plast. Anti-fog film foamer for glass and plastic.
- I skum for støvnedsettelse. - In foam for dust reduction.
For sure betonqrensere. For acidic concrete cleaners.
- Skumbobler for luftpåvisning i ventilasjonssystem. - Foam bubbles for air detection in the ventilation system.
Husholdning, kosmetikk og personlige produkter Skylle-hjelpemiddel for oppvask. Household, cosmetics and personal products Rinse aid for washing dishes.
- Flytende polermiddelblandinger. - Liquid polishing compounds.
- Utjevningsmiddel i gulv-voks. - Leveling agent in floor wax.
- Tilsetning for alkaliske ovnsrensere. - Additive for alkaline oven cleaners.
- Synergisk forbedrer for desinfeksjonsmidler. - Synergistically improves for disinfectants.
Tepperensemidler. Carpet cleaners.
- Synergisk fuktemiddel i vaskemidler. - Synergic wetting agent in detergents.
Tilsetning for beskyttende belegg på metaller (matningsmot-stand) (fettmotstand). - For forbedring av glans og antistatiske egenskaper. Additive for protective coating on metals (feed resistance) (grease resistance). - For improving gloss and antistatic properties.
Hårshampoingrediens. Hair shampoo ingredient.
Barberskumingrediens. Shaving foam ingredient.
- Olje og vannavstøtende kosmetisk pudderingrediens. - Oil and water repellent cosmetic powder ingredient.
Bestanddel i "lotions" eller kremer for hud eller hår. Ingredient in "lotions" or creams for skin or hair.
Bestanddel i hudbeskyttende kremer. Ingredient in skin protective creams.
Fotografi og grafisk Photography and graphics
Trykkfarvetilsetning for forbedring av flyt og jevnhet, basert Printing ink additive to improve flow and uniformity, based
både på vann og oppløsningsmiddel. both on water and solvent.
Fuktemiddel for blekk. Wetting agent for ink.
For å hindre pigmentstrømning og fIotasjon i trykkfarver. To prevent pigment flow and flotation in printing inks.
For å danne farveavstøtende overflater for vannfri lito-plater, eller elektrografisk belegg. - For å hindre nettverkdannelse av gelatinlag og for å bedre jevnhet. To form color resistant surfaces for waterless litho plates, or electrographic coating. - To prevent network formation of gelatin layers and to improve uniformity.
Bidra til filmtørking. Contribute to film drying.
- Forbedre filmbelegg og redusere "contractionflecks". - Improve film coverage and reduce "contraction flecks".
- Fukting-, utjevnings-, antikraterhjelpemiddel. - Moisturizing, leveling, anti-crater aid.
- Overflateaktive midler for fremkalleroppløsninger. - Surfactants for developer solutions.
- Fotoemulsjonsstabilisator. - Photoemulsion stabilizer.
- Hindre foto-smøremiddelagglomering. - Prevent photo-lubricant agglomeration.
- Belegningshjelpemiddel ved fremstilling av flerelags film-elementer. - Coating aid for the production of multi-layer film elements.
- Antistatisk fuktemiddel for filmbelegg. - Antistatic wetting agent for film coating.
- Antiduggmiddel for filmer. - Antifog agent for films.
- Bindemidler for fyllstoffer og fluorpolymerfilmer. - Binders for fillers and fluoropolymer films.
I belegg for nematiske flytende krystallceller. In coatings for nematic liquid crystal cells.
I eksemplene ble overflatespenningen målt med DuNouy tensio-meter ved 0,1 % konsentrasjon i vann ved 25°C. In the examples, the surface tension was measured with a DuNouy tensiometer at 0.1% concentration in water at 25°C.
Eksempel 1 Example 1
Fremstilling av forbindelser med formel Preparation of compounds of formula
2,5 g (0,0255 mol maleinsyreanhydrid i 2,5 g metyletylketon ble satt til 25 g (0,025 mol) polyetylenoksyd med molekylvekt 1000 (antall etylenoksydenheter mellom 15 og 30) og omrørt i 12 timer ved 75°C under nitrogen. Ved denne tid viste infra-rød analyse anhydridbånd ved 1780 cm<-1> og 1850 cm<-1>. 11,8 g perfluoralkyl-etylmerkaptan (perfluoralkylhalvdelen R f har en fordeling oå 27 % (- 5 %) C,, 50 % (-5 %) CQ, og 23 % + 6 8 (- <5><%>) <C>1Q) ( 0,025 mol) av gjennomsnittlig molekylvekt 478 ble sammen med 0,2 g trietylamin som katalysator (,0002 mol) tilsatt og blandingen omrørt i 12 timer ved 50°C. Den til å begynne med opake blanding ble klar etter 3 timer. Den klare oppløsningen ble tørket i vakuum ved 80°C i 5 timer. Produktet er en bløt voks som er oppløselig i vann. 2.5 g (0.0255 mol) of maleic anhydride in 2.5 g of methyl ethyl ketone was added to 25 g (0.025 mol) of polyethylene oxide with a molecular weight of 1000 (number of ethylene oxide units between 15 and 30) and stirred for 12 hours at 75°C under nitrogen. this time, infrared analysis showed anhydride bands at 1780 cm<-1> and 1850 cm<-1>. 11.8 g of perfluoroalkyl ethyl mercaptan (the perfluoroalkyl moiety R f has a distribution of 27% (-5%) C,, 50% (-5%) CQ, and 23% + 6 8 (- <5><%>) <C>1Q) (0.025 mol) of average molecular weight 478 were combined with 0.2 g of triethylamine as a catalyst (.0002 mol) added and the mixture stirred for 12 hours at 50°C. The initially opaque mixture became clear after 3 hours. The clear solution was dried in vacuo at 80°C for 5 hours. The product is a soft wax which is soluble in water .
Eksempel 2- 11 Example 2-11
Under anvendelse av fremgangsmåte ifølge eksempel 1, fremstilles forbindelser med struktur Using the method according to example 1, compounds with structure are prepared
med hydroksyforbindelsene angitt i tabell 1. with the hydroxy compounds listed in Table 1.
Overflatespenningen ble målt for hver prøve, innbefattende eksempel 1 på en 0,1 % oppløsning i vann. The surface tension was measured for each sample, including Example 1 at a 0.1% solution in water.
Eksempel 12 Example 12
Reaksjonsprodukter av polyetylenoksyd 600, maleinsyreanhydrid og 1,1,2,2-tetrahydxoperfluoroktylmerkaptan. Reaction products of polyethylene oxide 600, maleic anhydride and 1,1,2,2-tetrahydroxoperfluorooctyl mercaptan.
Maleinsyreanhydrid (0,25 mol), 2,5 g) oppløst i 10 g aceton Maleic anhydride (0.25 mol), 2.5 g) dissolved in 10 g of acetone
ble satt til polyetylenoksyd (molekylvekt 600), was added to polyethylene oxide (molecular weight 600),
(0,0255 mol, 15,3 g) og omrørt natten over med trietylenamin-katalysator (2,5 mol %). (0.0255 mol, 15.3 g) and stirred overnight with triethyleneamine catalyst (2.5 mol %).
Infrarødt spekter viste intet anhydridbånd ved 178 0 cm ^ og 1850 cm<-1>. Infrared spectrum showed no anhydride band at 178 0 cm ^ and 1850 cm<-1>.
1,1,2.2-tetrahydroperfluoroktylmerkaptan (0,0255 mol), (9,64 g) ble satt til og reaksjonsoppløsningen ble omrørt ved værelsestemperatur i 2 dager før tynnsjiktkromatografi (TLC) viste at det ikke var mere uomsatt merkaptan. Den klare oppløsning ble tørket under vakuum for å gi klar hvit olje (83,8 % utbytte). 1,1,2,2-tetrahydroperfluorooctyl mercaptan (0.0255 mol), (9.64 g) was added and the reaction solution was stirred at room temperature for 2 days before thin layer chromatography (TLC) showed no more unreacted mercaptan. The clear solution was dried under vacuum to give a clear white oil (83.8% yield).
Infrarød analyse er overensstemmende med strukturen. Elemen-tæranalyse for C-0H,nF..0,_S Infrared analysis is consistent with the structure. Elemental analysis for C-0H,nF..0,_S
Jo bu ±3 i-lJo bu ±3 i-l
Overflatespenningen i en 0,1 % oppløsning i vann var 27,7 (^n) . The surface tension in a 0.1% solution in water was 27.7 (^n) .
cm Eksempel 13 cm Example 13
Reaksjonsproduktet av bis-3-aminopropyleter av polyetylenoksyd (molvekt 1000), maleinsyreanhydrid og 1,1,2,2-tetrahydroper-fluoroktyl-merkaptan The reaction product of bis-3-aminopropyl ether of polyethylene oxide (mol weight 1000), maleic anhydride and 1,1,2,2-tetrahydroper-fluorooctyl-mercaptan
og dets isomer. and its isomers.
Maleinsyreanhydridet (0,0255 mol, 2,5 g) ble satt til bis-3-aminopropyleter av polyetylenoksyd (molekylvekt 1000) (0,01275^ mol, 11,86 g) i 10 g aceton og ble omrørt i 24 timer (IR viser ingen anhydridbånd ved 1780 cm og 1850 cm ). The maleic anhydride (0.0255 mol, 2.5 g) was added to bis-3-aminopropyl ether of polyethylene oxide (molecular weight 1000) (0.01275 mol, 11.86 g) in 10 g of acetone and was stirred for 24 hours (IR shows no anhydride bands at 1780 cm and 1850 cm ).
1,1,2,2-tetrahydroperfluoroktylmerkaptan ble tilsatt og reaksjonen ble omrørt natten over ved værelsestemperatur. TLC viser ikke noen spor av uomsatt merkaptan. 1,1,2,2-tetrahydroperfluorooctyl mercaptan was added and the reaction was stirred overnight at room temperature. TLC shows no trace of unreacted mercaptan.
Den klart gule oppløsning ble tørket under vakuum for å gi 26,17 g av klart gul viskøs olje (99,7 % utbytte). The clear yellow solution was dried under vacuum to give 26.17 g of clear yellow viscous oil (99.7% yield).
Infrarød analyse var overensstemmende med strukturen. Infrared analysis was consistent with the structure.
Elementæranalyse for C_,H,<n>.<F>.,<N>.<O>,<cS>Elemental analysis for C_,H,<n>.<F>.,<N>.<O>,<cS>
66 102 26 2 25 66 102 26 2 25
En 0,1 % oppløsning i vann sammen med 0,1 % C0H..-CCH.0(C_H.0),nH d vn O J. / o 4 ^4 11) A 0.1% solution in water together with 0.1% C0H..-CCH.0(C_H.0),nH d vn O J. / o 4 ^4 11)
hadde en overflatespenning på 23,8 (~^~ )• had a surface tension of 23.8 (~^~ )•
Eksempel 14 til 18 Examples 14 to 18
2,55 g maleinsyreanhydrid og 2,55 g sulfolan som oppløsnings-middel ble satt til 36,45 g dinonylfenpl med formel 2.55 g of maleic anhydride and 2.55 g of sulfolane as solvent were added to 36.45 g of dinonylphenpl with the formula
og omrørt i 20 timer ved 60 C for å danne en reaksjonsblanding inneholdende en halvester med formel and stirred for 20 hours at 60 C to form a reaction mixture containing a half-ester of the formula
og dens isomer. and its isomers.
Til denne reaksjonsblanding ble det deretter satt 0,1 g trietylamin og 11,63 g R^CH^CH^SH under nitrogen og blandingen omrørt ved 60°C i ca. 7 timer. Produktet har formel 0.1 g of triethylamine and 11.63 g of R^CH^CH^SH were then added to this reaction mixture under nitrogen and the mixture stirred at 60°C for approx. 7 hours. The product has formula
Rf-fordeling: 0,9 % C^Rg, 329 % CgF^, 37,5 % CgF17Rf distribution: 0.9% C^Rg, 329% CgF^, 37.5% CgF17
22,9 % C10F21 og 5,3 % C^ F^. 22.9% C10F21 and 5.3% C^ F^.
Eksemplene 14 til 18 utføres på samme måte. Examples 14 to 18 are carried out in the same way.
Overflatespenningen måles for hver prøve på en 0,1 % oppløsning i vann. The surface tension is measured for each sample on a 0.1% solution in water.
Eksempel 19 Example 19
Eksempel 1 ble gjentatt idet det ble benyttet følgende R^-tioler: Example 1 was repeated using the following R^ thiols:
for å gi tilsvarende vannoppløselige overflateaktive midler. to provide corresponding water-soluble surfactants.
Claims (9)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/858,218 US4171282A (en) | 1977-12-07 | 1977-12-07 | Fluorinated nonionic surfactants |
US94482078A | 1978-09-22 | 1978-09-22 |
Publications (3)
Publication Number | Publication Date |
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NO784108L NO784108L (en) | 1979-06-08 |
NO150683B true NO150683B (en) | 1984-08-20 |
NO150683C NO150683C (en) | 1984-11-28 |
Family
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Application Number | Title | Priority Date | Filing Date |
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NO784108A NO150683C (en) | 1977-12-07 | 1978-12-06 | PERFLUORALLYCYL-SUBSTITUTED HALVES - OR AMIDE TENSIDES, EVEN IN THE FORM OF MIXTURES, AND USE THEREOF |
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JP (1) | JPS5484524A (en) |
AU (1) | AU519243B2 (en) |
BR (1) | BR7808012A (en) |
CA (1) | CA1129429A (en) |
DE (1) | DE2852593A1 (en) |
FR (1) | FR2411212A1 (en) |
GB (1) | GB2010874B (en) |
IT (1) | IT1106947B (en) |
NL (1) | NL7811945A (en) |
NO (1) | NO150683C (en) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS5935573B2 (en) * | 1980-06-28 | 1984-08-29 | シ−アイ化成株式会社 | agricultural cladding |
JPS5856959A (en) * | 1981-09-29 | 1983-04-04 | Nissin Kogyo Kk | Booster of negative pressure type |
JPS6028860B2 (en) * | 1981-09-29 | 1985-07-06 | アキレス株式会社 | Eggplant cultivation film |
DK435881A (en) * | 1981-10-01 | 1983-04-02 | Niels Ole Vesterager | WASHING ACTIVE DOSAGE UNIT, METHOD OF PREPARING IT AND THE USE OF IT |
JPS5889360A (en) * | 1981-11-24 | 1983-05-27 | アキレス株式会社 | Agricultural film |
DE3903005A1 (en) * | 1989-02-02 | 1990-08-16 | Pfersee Chem Fab | METHOD FOR THE PRODUCTION OF MODIFIED POLYSILOXANES, THE POLYSILOXANES SO MANUFACTURED, THE USE THEREOF AND THE MATERIALS SO TREATED |
US5266724A (en) * | 1990-09-04 | 1993-11-30 | Matsushita Electric Industrial Co., Ltd. | Fluorine-containing compounds |
US5188747A (en) * | 1990-09-04 | 1993-02-23 | Matsushita Electric Industrial Co., Ltd. | Fluorine-containing lubricant compounds |
DE4240274B4 (en) * | 1992-12-01 | 2004-02-12 | Minnesota Mining And Manufacturing Co., Saint Paul | Polysiloxanes with fluoroaliphate and carboxyl-containing terminal groups, their preparation and their use in the treatment of fiber substrates |
DE4244951C2 (en) * | 1992-12-01 | 1998-08-06 | Minnesota Mining & Mfg | New poly:siloxane cpd(s) and carboxylic acid derivs., prepn. and use |
US5612431A (en) * | 1994-09-21 | 1997-03-18 | Minnesota Mining And Manufacturing Company | Leaching of precious metal ore with fluoroaliphatic surfactant |
BRPI0414883A (en) | 2003-09-29 | 2006-12-12 | Ethena Healthcare Inc | composition, composition concentrate, and disinfectant and gel-like alcoholic compositions |
DE102004062775A1 (en) | 2004-12-21 | 2006-06-29 | Stockhausen Gmbh | Alcoholic pump foam |
AU2006222502B2 (en) | 2005-03-07 | 2010-02-11 | Deb Ip Limited | High alcohol content foaming compositions with silicone-based surfactants |
JP6198058B2 (en) * | 2013-12-19 | 2017-09-20 | Dic株式会社 | Surfactant composition, coating composition, and resist composition |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4075237A (en) * | 1968-04-10 | 1978-02-21 | Geigy Chemical Corporation | Perfluorinated esters of fumaric acid and certain other ethylenically unsaturated poly-basic acid and soil repellant polymers thereof |
NL7204067A (en) * | 1971-03-29 | 1972-10-03 | ||
GB1354138A (en) * | 1971-10-15 | 1974-06-05 | Ici Ltd | Fluorocarbon surfactants |
GB1410328A (en) * | 1971-12-21 | 1975-10-15 | Unilever Ltd | Alkoxylation process |
DE2238740C3 (en) * | 1972-08-05 | 1981-07-16 | Bayer Ag, 5090 Leverkusen | Polyethers containing perfluoroalkyl groups and processes for their preparation and their use |
US3794672A (en) * | 1973-07-05 | 1974-02-26 | Dow Corning | Perfluoroalkyl silicon compounds containing sulfur |
CH628247A5 (en) * | 1975-01-03 | 1982-02-26 | Ciba Geigy Ag | Aqueous, film-forming concentrates for extinguishing or preventing fire with a content of non-anionic compounds containing perfluoroalkylalkylenethio groups |
US4081399A (en) * | 1975-09-22 | 1978-03-28 | Ciba-Geigy Corporation | Process for the preparation of concentrated solutions of fluorinated amphoteric surfactants |
FR2328070A1 (en) * | 1975-10-17 | 1977-05-13 | Ugine Kuhlmann | ANTI-STAIN PRODUCTS ALLOWING THE EASY REMOVAL OF SOIL IN WASHING |
-
1978
- 1978-12-05 CA CA317,372A patent/CA1129429A/en not_active Expired
- 1978-12-05 JP JP14975878A patent/JPS5484524A/en active Granted
- 1978-12-05 GB GB7847286A patent/GB2010874B/en not_active Expired
- 1978-12-05 DE DE19782852593 patent/DE2852593A1/en active Granted
- 1978-12-06 IT IT52206/78A patent/IT1106947B/en active
- 1978-12-06 AU AU42255/78A patent/AU519243B2/en not_active Expired
- 1978-12-06 NO NO784108A patent/NO150683C/en unknown
- 1978-12-06 FR FR7834422A patent/FR2411212A1/en active Granted
- 1978-12-06 BR BR7808012A patent/BR7808012A/en unknown
- 1978-12-07 NL NL7811945A patent/NL7811945A/en not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
GB2010874A (en) | 1979-07-04 |
DE2852593A1 (en) | 1979-06-13 |
NL7811945A (en) | 1979-06-11 |
IT1106947B (en) | 1985-11-18 |
FR2411212A1 (en) | 1979-07-06 |
FR2411212B1 (en) | 1983-12-16 |
BR7808012A (en) | 1979-08-07 |
JPS5484524A (en) | 1979-07-05 |
NO784108L (en) | 1979-06-08 |
AU519243B2 (en) | 1981-11-19 |
JPS632951B2 (en) | 1988-01-21 |
CA1129429A (en) | 1982-08-10 |
GB2010874B (en) | 1982-10-06 |
IT7852206A0 (en) | 1978-12-06 |
AU4225578A (en) | 1979-06-14 |
NO150683C (en) | 1984-11-28 |
DE2852593C2 (en) | 1988-04-14 |
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