NO154136B - PAPER MACHINE WASHING MACHINE O.L. - Google Patents
PAPER MACHINE WASHING MACHINE O.L. Download PDFInfo
- Publication number
- NO154136B NO154136B NO783875A NO783875A NO154136B NO 154136 B NO154136 B NO 154136B NO 783875 A NO783875 A NO 783875A NO 783875 A NO783875 A NO 783875A NO 154136 B NO154136 B NO 154136B
- Authority
- NO
- Norway
- Prior art keywords
- diol
- radical
- mol
- polyester
- divalent
- Prior art date
Links
- 238000005406 washing Methods 0.000 title 1
- -1 alcohol alcohols Chemical class 0.000 claims description 14
- 229920000728 polyester Polymers 0.000 claims description 14
- 150000002009 diols Chemical class 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 229920000570 polyether Polymers 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000005442 diisocyanate group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- COXRPBBNPBCNDM-UHFFFAOYSA-N Dioxamide Natural products C1=C2OCOC2=CC(C=CC(=O)N(CCC=2C=C3OCOC3=CC=2)C)=C1 COXRPBBNPBCNDM-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000009987 spinning Methods 0.000 description 6
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- FPQJEXTVQZHURJ-UHFFFAOYSA-N n,n'-bis(2-hydroxyethyl)oxamide Chemical compound OCCNC(=O)C(=O)NCCO FPQJEXTVQZHURJ-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical group NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 229940093476 ethylene glycol Drugs 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000003901 oxalic acid esters Chemical class 0.000 description 2
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical group NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 2
- 229920003225 polyurethane elastomer Polymers 0.000 description 2
- JRMAQQQTXDJDNC-UHFFFAOYSA-M 2-ethoxy-2-oxoacetate Chemical compound CCOC(=O)C([O-])=O JRMAQQQTXDJDNC-UHFFFAOYSA-M 0.000 description 1
- APKFLZGRWMXNNV-UHFFFAOYSA-N 6-(carboxyamino)hexylcarbamic acid Chemical compound OC(=O)NCCCCCCNC(O)=O APKFLZGRWMXNNV-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229920000562 Poly(ethylene adipate) Polymers 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 210000004177 elastic tissue Anatomy 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- JPCJYZZUEISJGO-UHFFFAOYSA-N n,n'-bis(3-hydroxypropyl)oxamide Chemical compound OCCCNC(=O)C(=O)NCCCO JPCJYZZUEISJGO-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002166 wet spinning Methods 0.000 description 1
- 238000005491 wire drawing Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06B—TREATING TEXTILE MATERIALS USING LIQUIDS, GASES OR VAPOURS
- D06B3/00—Passing of textile materials through liquids, gases or vapours to effect treatment, e.g. washing, dyeing, bleaching, sizing, impregnating
- D06B3/02—Passing of textile materials through liquids, gases or vapours to effect treatment, e.g. washing, dyeing, bleaching, sizing, impregnating of fibres, slivers or rovings
Description
Fremgangsmåte til fremstilling av oksamidgruppeholdige polyuretanelastomere. Process for the production of polyurethane elastomers containing oxamide groups.
Oppfinnelsen vedrører fremstilling av polyuretanelastomere, som i molekylet inneholder et flertall funksjonelle grupper: The invention relates to the production of polyurethane elastomers, the molecule of which contains a plurality of functional groups:
i hvilke in which
Z er et toverdig radikal tilsvarende en polyester eller en polyeter HO-Z-OH med Z is a divalent radical corresponding to a polyester or a polyether HO-Z-OH with
en molekylvekt på 500—2500, a molecular weight of 500-2500,
T er et alifatisk cykloalifatisk eller aromatisk toverdig organisk radikal, T is an aliphatic cycloaliphatic or aromatic divalent organic radical,
D er et toverdig organisk radikal tilsvarende en av formlene - RNHCOCONHR - D is a divalent organic radical corresponding to one of the formulas - RNHCOCONHR -
eller or
- RNHCOCONH - R'- NHCOCONHR -, - RNHCOCONH - R'- NHCOCONHR -,
hvor R betegner et alkylenradikal og R' where R denotes an alkylene radical and R'
betegner et toverdig hydrokarbonradikal denotes a divalent hydrocarbon radical
eventuelt inneholdende heteroatomer optionally containing heteroatoms
eller funksjonelle grupper som ikke reagerer med isocyanater eller med nær-liggende hydrogenatomer danner et toverdig radikal i et cyklisk diamin. or functional groups that do not react with isocyanates or with nearby hydrogen atoms form a divalent radical in a cyclic diamine.
Disse kjedeformede polymere er an-vendbare for fremstilling av myke og These chain-shaped polymers are applicable for the production of soft and
elastiske fibre og folier med god stabilitet elastic fibers and foils with good stability
mot lys og varme. against light and heat.
Det er kjent å gjøre polyuretaner It is known to make polyurethanes
strekkbare til fibre ved enkel polyaddisjon stretchable to fibers by simple polyaddition
av 1,6-diisocyanato-heksan til N,N'-di-(3'-hydroksy-propyl)-oksamid eller ved en of 1,6-diisocyanato-hexane to N,N'-di-(3'-hydroxy-propyl)-oxamide or by a
polykondensasjon av en diester av heksa-metylendikarbaminsyre med l,6-bis-(3-hydroksy-propyloksamido)-heksan (se polycondensation of a diester of hexa-methylenedicarbamic acid with 1,6-bis-(3-hydroxy-propyloxamido)-hexane (see
fransk patent nr. 879 703). De dannede produkter inneholder vesentlig uretan- og oksaminsyregrupper med utelukkelse av hvert polyester- eller polyeterfragment. De gir sprø fibre, men savner mykhet og elastisitet. French Patent No. 879,703). The products formed essentially contain urethane and oxamic acid groups to the exclusion of each polyester or polyether fragment. They provide brittle fibres, but lack softness and elasticity.
Oppfinnelsen vedrører altså en fremgangsmåte for fremstilling av elastomere polyuretaner ved at man suksessivt eller samtidig omsetter 1 mol av en polyester eller polyeter HOZOH, som inneholder to hydroksylgrupper i endeplasering med 2 mol av et diisocyanat OCN-T-CNO, idet Z er et toverdig radikal og T er et alifatisk, cykloalifatisk eller aromatisk toverdig radikal, og deretter med 1 mol av en diol, og fremgangsmåten er karakterisert ved at den diol som anvendes, er en monooksamiddiol OH-R-NH-CO-CO-NH-R-OH eller en dioksamiddiol OH-R-NH-CO-CO-NH-R'-NH-CO-CO-NH-R-OH, idet R betegner et alkylenradikal og R' et toverdig hydrokarbonradikal, som eventuelt inneholder heteroatomer eller funksjonelle grupper, som ikke reagerer med isocyanater og alkoholer, idet R' også med det naboplaserte nitrogenatom kan danne et toverdig radikal i et cyklisk diamin. The invention therefore relates to a method for the production of elastomeric polyurethanes by successively or simultaneously reacting 1 mol of a polyester or polyether HOZOH, which contains two hydroxyl groups in the end position with 2 mol of a diisocyanate OCN-T-CNO, where Z is a divalent radical and T is an aliphatic, cycloaliphatic or aromatic divalent radical, and then with 1 mol of a diol, and the method is characterized in that the diol used is a monooxamide diol OH-R-NH-CO-CO-NH-R-OH or a dioxamide diol OH-R-NH-CO-CO-NH-R'-NH-CO-CO-NH-R-OH, where R denotes an alkylene radical and R' a divalent hydrocarbon radical, possibly containing heteroatoms or functional groups, which do not react with isocyanates and alcohols, as R' can also form a divalent radical in a cyclic diamine with the neighboring nitrogen atom.
De polyestre som anvendes for fremstilling av de nye polymere, er kjedeformede kondensasjonsprodukter av alifatiske og/eller cykliske disyrer og alifatiske og/eller cykliske dioler med en molekylvekt på 500—2500, inneholdende to ende-plaserte hydroksylgrupper og med et syre-tall på praktisk talt null for det formål å unngå dannelsen av sekundære produkter som ville kunne dannes ved innvirkning av frie syregrupper på diisocyanatene og diol-ene hvormed de omsettes. Slike polyestere er eksempelvis kondensasjonsprodukter av adipinsyre eller teraftalsyre med etylen-glykol og/eller propylenglykol. Man kan og-så i stedet for polyester anvende de polyetre, som fåes ved polymerisasjon eller sampolymerisasjon av olefinoksyder, som etylenoksyd eller propylenoksyd, tetrahyd-rofuran etc, idet disse polyetre likeledes har en molekylvekt på 500—2500 og en fri hydroksylgruppe ved hver kjedeende. The polyesters used for the production of the new polymers are chain-shaped condensation products of aliphatic and/or cyclic diacids and aliphatic and/or cyclic diols with a molecular weight of 500-2500, containing two end-positioned hydroxyl groups and with an acid number of practically counted zero for the purpose of avoiding the formation of secondary products which could be formed by the action of free acid groups on the diisocyanates and diols with which they are reacted. Such polyesters are, for example, condensation products of adipic acid or teraphthalic acid with ethylene glycol and/or propylene glycol. Instead of polyester, you can also use the polyethers obtained by polymerization or copolymerization of olefin oxides, such as ethylene oxide or propylene oxide, tetrahydrofuran, etc., as these polyethers also have a molecular weight of 500-2500 and a free hydroxyl group at each chain end .
De diisocyanater, som man omsetter, er alifatiske, cykloalifatiske eller aromatiske diisocyanater, som 1,6-diisocyanato-heksan, de isomere diisocyanatotoluolene, p,p'-diisocyanato-difenylmetan. De kan inne-holde andre funksjonelle grupper, som p,p'-diisocy anatotolylkartaamid. The diisocyanates which are reacted are aliphatic, cycloaliphatic or aromatic diisocyanates, such as 1,6-diisocyanato-hexane, the isomeric diisocyanatotoluenes, p,p'-diisocyanato-diphenylmethane. They may contain other functional groups, such as p,p'-diisocy anatotolylcartaamide.
Oxamiddiolene med formel (II) er de kjente produkter som man får ved omsetning av et overskudd av en amino-alkohol HO-R-NH2 med en oksalsyreester. Man kan også anvende N,N'-bis-(2-hydroksyetyl)-oksamid, fremstillet fra etanolamin og etyloksalat, som beskrevet i det amerikan-ske patent nr. 2 379 261. The oxamide diols of formula (II) are the known products which are obtained by reacting an excess of an amino alcohol HO-R-NH2 with an oxalic acid ester. One can also use N,N'-bis-(2-hydroxyethyl)-oxamide, prepared from ethanolamine and ethyl oxalate, as described in American patent no. 2,379,261.
Dioksamiddiolene med formel (III) er likeledes kjente produkter som kan frem-stilles ved omsetning av et overskudd av en oksalsyreester og et diamin H2N-R'-NH2The dioxamide diols of formula (III) are likewise known products which can be produced by reacting an excess of an oxalic acid ester and a diamine H2N-R'-NH2
(idet R' har den ovenfor angitte betydning) (where R' has the meaning given above)
lor å oppnå en oksaminsyrediester som med en aminoalkohol HO-R-NH2 (idet R har den ovenfor angitte betydning) gir den ønskede diol, i henhold til de fremgangs-måter som er angitt i fransk patent nr. 879 703 for fremstilling av 1,6-bis-hyd-roksy-propolyoksamido)-heksan med for-melen HO(CH2)3NHCOCONH-(CH2)6<->lor obtaining an oxamic acid diester which with an amino alcohol HO-R-NH2 (where R has the above meaning) gives the desired diol, according to the methods indicated in French patent no. 879 703 for the preparation of 1, 6-bis-hydroxy-propolyoxamido)-hexane with the formula HO(CH2)3NHCOCONH-(CH2)6<->
NHCOCONH(CH2)3OH. NHCOCONH(CH2)3OH.
Man kan hensiktsmessig anvende de dioksamiddioler, som er omtalt i fransk patent nr. 1 338 399 i hvilke dioler det fin-nes grupper med den generelle formel HO-Y-NH-COCONH-X-A-X-NHCOCONH-Y-OH, hvor Y betegner et alkylenradial, X betegner en toverdig hydrokarbonradikal og A betegner et oksygenatom, en sulfon-gruppe eller gruppen One can appropriately use the dioxamide diols, which are mentioned in French patent no. 1,338,399, in which diols there are groups with the general formula HO-Y-NH-COCONH-X-A-X-NHCOCONH-Y-OH, where Y denotes a alkylene radial, X denotes a divalent hydrocarbon radical and A denotes an oxygen atom, a sulfone group or the group
idet X' er et enverdig hydrokarbonradikal og enheten -NH-X-A-X-NH- eventuelt kan være erstattet med piperazinkjerne som eventuelt er substituert. where X' is a monovalent hydrocarbon radical and the unit -NH-X-A-X-NH- can optionally be replaced with a piperazine nucleus which is optionally substituted.
For fremstilling av de polymere ifølge oppfinnelsen kan man under den indiffe-rente atmosfære oppvarme, enten som så-dant eller i oppløsning, diisocyanatet med den forpolymeriserte polyester eller polyeter, hvorpå man behandler det således dannede makromolekylære diisocyanat med oksalsyrediolet. Man kan likeledes i henhold til en foretrukket utførelsesform iføl-ge oppfinnelsen samtidig oppvarme samt-lige reaksjonskomponenter til temperaturer av størrelsesorden 180—220° C. I dette til-felle oppvarmer man under en indifferent atmosfære og suksessivt, under opprett-holdelse av en kraftig omrøring, for man iakttar ofte to suksessive temperaturer der reaksjonsmassen tykkgjøres kraftig. Denne masse er helt homogen ved avslutning av reaksjonen. Den således dannede polymere kan anvendes direkte etter uthelling fra reaksjonskaret for støpning, trådtrekning etc. i smeltet tilstand. Den kan også etter avkjøling og granulering på nytt oppløses i et organisk oppløsningsmiddel som dimetylsulfoksyd, hvis man ønsker å arbeide i henhold til den teknikk som er anvendbar for polymere i oppløsning, spesielt under slike betingelser som ikke krever så høye temperaturer som de som kreves ved den polymeres opparbeidelse i smeltet tilstand. For the production of the polymers according to the invention, the diisocyanate can be heated under the indifferent atmosphere, either as such or in solution, with the prepolymerized polyester or polyether, after which the macromolecular diisocyanate thus formed is treated with the oxalic acid diol. It is also possible, according to a preferred embodiment according to the invention, to simultaneously heat all reaction components to temperatures of the order of 180-220° C. In this case, one heats under an indifferent atmosphere and successively, while maintaining a strong stirring, because one often observes two successive temperatures where the reaction mass thickens strongly. This mass is completely homogeneous at the end of the reaction. The polymer thus formed can be used directly after pouring from the reaction vessel for casting, wire drawing, etc. in the molten state. It can also, after cooling and granulation, be redissolved in an organic solvent such as dimethylsulfoxide, if one wishes to work according to the technique applicable to polymers in solution, especially under such conditions which do not require such high temperatures as those required by the processing of the polymer in the molten state.
Oppfinnelsen skal i det følgende be-lyses nærmere ved hjelp av noen eksempler. In the following, the invention will be explained in more detail with the help of some examples.
Eksempel 1. Example 1.
I et 250 ml reaksjonskar med et røre-verk og en gasstilførsel innfører man 46,86 g av et blandet (50/50) etylenglykol/pro-pylenglykolpolyadipat med en molekylvekt på 1750 og et hydroksyltall på 0,105 (hyd-roksyltallet tilsvarer antallet hydroksylgrupper pr. 100 g polymer). Man tilsetter til slutt 3,14 g N,N'-bis-(hydroksyetyl)-ok-samid og 7,39 g 1,6-diisocyanato-heksan. Reaksjonskaret spyles med nitrogen hvorved det oppvarmes suksessivt og regelmessig under omrøring (økning av temperaturen med 1° C pr. minutt) til en temperatur på 220° C som man bibeholder i 15 minutter. Reaksjonsmassen er homogen og kan direkte støpes eller spinnes. Ved spinning ved 160° C og uten strekning får man fibre som har en styrke på 0,2 g/denier og en bruddforlengelse på 1200 pst. In a 250 ml reaction vessel with a stirrer and a gas supply, 46.86 g of a mixed (50/50) ethylene glycol/propylene glycol polyadipate with a molecular weight of 1750 and a hydroxyl number of 0.105 (the hydroxyl number corresponds to the number of hydroxyl groups per .100 g of polymer). Finally, 3.14 g of N,N'-bis-(hydroxyethyl)-oxamide and 7.39 g of 1,6-diisocyanato-hexane are added. The reaction vessel is flushed with nitrogen whereby it is heated successively and regularly with stirring (increasing the temperature by 1° C per minute) to a temperature of 220° C which is maintained for 15 minutes. The reaction mass is homogeneous and can be directly cast or spun. When spinning at 160° C and without stretching, fibers are obtained that have a strength of 0.2 g/denier and an elongation at break of 1200 percent.
Eksempel 2. Example 2.
Man går frem som i ovennevnte eksempel og omsetter 3,09 g l,6-bis-(N-2-hyd-roksyetyloksamido)-heksan og 5,90 g 1,6-diisocyanatoheksan med 46,91 g av samme polyester. Man oppvarmer suksessivt under energisk omrøring til en temperatur på 190° C, hvilken temperatur bibeholdes i 30 minutter. Ved spinning av den dannede polymer ved 160° C under en strekning av disse til 120° ved utløpet fra trådspinnings-munnstykkene får man myke og elastiske tråder med en styrke på 0,3 g/denier og en bruddforlengelse på 1100 pst. One proceeds as in the above-mentioned example and reacts 3.09 g of 1,6-bis-(N-2-hydroxyethyloxamido)-hexane and 5.90 g of 1,6-diisocyanatohexane with 46.91 g of the same polyester. It is successively heated with vigorous stirring to a temperature of 190° C, which temperature is maintained for 30 minutes. By spinning the formed polymer at 160° C during a stretch of these to 120° at the outlet from the thread spinning nozzles, soft and elastic threads are obtained with a strength of 0.3 g/denier and an elongation at break of 1100 percent.
Denne polymer som er oppløselig i dimetylsulfoksyd, kan også støpes eller spinnes på i og for seg kjent måte for støpning eller våtspinning. This polymer, which is soluble in dimethylsulfoxide, can also be cast or spun in a manner known per se for casting or wet spinning.
Eksempel 3. Example 3.
Man går frem på samme måte som angitt i eksempel 2 og omsetter 3,77 g bis-(N-2-hydroksyetyloksamid)-p,p'-difenyl-metan og 5,81 g diisocyanatoheksan med 46,23 g av samme polyester. Den dannede polymere spinnes ved 175° C med en strekning av 180° ved utløpet fra trådspinnings-munnstykket, idet man får tråder som har en styrke på 0,3 g/denier og en bruddutvidelse på 1100 pst. Den polymere er likeledes oppløselig i dimetylsulfoksyd. One proceeds in the same way as stated in example 2 and reacts 3.77 g of bis-(N-2-hydroxyethyloxamide)-p,p'-diphenyl-methane and 5.81 g of diisocyanatohexane with 46.23 g of the same polyester. The polymer formed is spun at 175° C with a stretch of 180° at the exit from the thread spinning nozzle, obtaining threads that have a strength of 0.3 g/denier and an elongation at break of 1100 percent. The polymer is likewise soluble in dimethyl sulfoxide .
Eksempel 4. Example 4.
Man går frem på samme måte som angitt i eksempel 2 og omsetter 3,03 g N.N'-bis-(hydroksyetyl)-oksamid og 10,82 g p,p'-diisocyanat-difenylmetan med 46,97 g av samme polyester. Den dannede polymer gir ved smeltspinning ved 161° C og uten strekning ved utløpet fra spinnemunnstyk-ket tråder som har en styrke på 0,16 g/denier og en bruddutvidelse på 1130 pst. One proceeds in the same way as indicated in example 2 and reacts 3.03 g of N.N'-bis-(hydroxyethyl)-oxamide and 10.82 g of p,p'-diisocyanate-diphenylmethane with 46.97 g of the same polyester. The formed polymer gives, when melt spinning at 161° C and without stretching at the exit from the spinning nozzle, threads which have a strength of 0.16 g/denier and an elongation at break of 1130 percent.
Eksempel 5. Example 5.
Under de samme betingelser som angitt i eksempel 2 omsetter man 6,04 g 1,6-diisocyanat-heksan, 1,24 g N,N'-bis-(hyd-roksyetyl)-oksamid og 48,76 g av en etylen-glykoladipatpolyester med en molekylvekt på 1720 og et hydroksyltall på 0,114. Den dannede polymer gir ved spinning ved 107° C under en strekning på 200 pst. tråder, som har en styrke på 0,56 g/denier og en bruddutvidelse på 900 pst. Under the same conditions as stated in example 2, 6.04 g of 1,6-diisocyanate-hexane, 1.24 g of N,N'-bis-(hydroxyethyl)-oxamide and 48.76 g of an ethylene- glycol adipate polyester with a molecular weight of 1720 and a hydroxyl number of 0.114. The polymer formed gives, when spun at 107° C. under a stretch of 200 percent, threads having a strength of 0.56 g/denier and an elongation at break of 900 percent.
Idet det gåes ut fra samme reaksjons-komponent omsetter man på samme måte 3,19 g N,N'-bis-(hydroksyetyl)-oksamid, 7,70 g 1,6-diisocyanat-heksan og 46,81 g polyester. Ved hjelp av spinning ved 143° C av den således dannede polymere under en strekning på 125 pst. fremstiller man fibre med en styrke på 0,42 g/denier og en ut-videlse på 1000 pst. Det fremgår herav, at en økning av antallet oksamidgrupper i den polymere har øket den polymeres smel-tepunkt betraktelig. Starting from the same reaction component, 3.19 g of N,N'-bis-(hydroxyethyl)-oxamide, 7.70 g of 1,6-diisocyanate-hexane and 46.81 g of polyester are reacted in the same way. By means of spinning at 143° C of the thus formed polymer under a stretch of 125%, fibers are produced with a strength of 0.42 g/denier and an expansion of 1000%. It appears from this that an increase of the number of oxamide groups in the polymer has increased the melting point of the polymer considerably.
Eksempel 6. Example 6.
Under de samme betingelser som i fo-regående eksempel omsetter man 3,48 g bis-(N-hydroksyetyl-N'-oksamido-propoksy)-etan med 5,77 g 1,6-diisocyanat-heksan og 46,52 g av den polyester, som anvendes i eksempel 1. Den dannede polymere som er oppløselig i dimetylsulfoksyd, gir myke og elastiske folier med en bruddutvidelse på 600 pst. Under the same conditions as in the previous example, 3.48 g of bis-(N-hydroxyethyl-N'-oxamido-propoxy)-ethane are reacted with 5.77 g of 1,6-diisocyanate-hexane and 46.52 g of the polyester used in example 1. The formed polymer, which is soluble in dimethylsulfoxide, gives soft and elastic foils with an elongation at break of 600 percent.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/853,068 US4160297A (en) | 1977-11-21 | 1977-11-21 | Pulp washer |
US05/951,540 US4246669A (en) | 1978-10-16 | 1978-10-16 | Dual belt pulp washer |
Publications (3)
Publication Number | Publication Date |
---|---|
NO783875L NO783875L (en) | 1979-05-22 |
NO154136B true NO154136B (en) | 1986-04-14 |
NO154136C NO154136C (en) | 1986-07-23 |
Family
ID=27127113
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO783875A NO154136C (en) | 1977-11-21 | 1978-11-17 | PAPER MACHINE WASHING MACHINE O.L. |
Country Status (7)
Country | Link |
---|---|
JP (1) | JPS54500055A (en) |
AR (1) | AR220159A1 (en) |
CA (1) | CA1092405A (en) |
FI (1) | FI69327C (en) |
NO (1) | NO154136C (en) |
SE (1) | SE422817B (en) |
WO (1) | WO1979000309A1 (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1980000460A1 (en) * | 1978-08-18 | 1980-03-20 | Envirotech Corp | Twin belt vacuum washer |
AT385790B (en) * | 1986-09-17 | 1988-05-10 | Andritz Ag Maschf | DEVICE FOR TREATING A BETWEEN AT LEAST TWO ENDLESS PERMANENT TAPES, e.g. SCREENBAND, GUIDED MATERIALS |
AT386850B (en) * | 1986-09-17 | 1988-10-25 | Andritz Ag Maschf | DEVICE FOR TREATING A BETWEEN AT LEAST TWO ENDLESS PERMANENT TAPES, e.g. SCREENBAND, GUIDED MATERIALS |
DE4018120A1 (en) * | 1990-06-06 | 1991-12-12 | Bernt U Treu | Cellulose washing |
US5513956A (en) * | 1994-01-14 | 1996-05-07 | Arrow International Investment Corp. | Circulatory assisted device with motor driven gas pump |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL76401C (en) * | ||||
US899440A (en) * | 1905-12-29 | 1908-09-22 | Walter Erben | Apparatus for extracting grease and potash salts from wool. |
US2745712A (en) * | 1953-10-22 | 1956-05-15 | Improved Machinery Inc | Process for countercurrent washing of cooking liquor out of pulp |
DE2121722A1 (en) * | 1971-05-03 | 1972-11-23 | Vepa Ag, Riehen, Basel (Schweiz) | Impregnating appts - partic for uniformly impregnating a binding agent into fleece |
FR2147894B1 (en) * | 1971-08-04 | 1974-10-11 | Neyrpic Bmb | |
US3857261A (en) * | 1973-08-27 | 1974-12-31 | Riggs & Lombard Inc | Textile scouring range |
-
1978
- 1978-11-17 NO NO783875A patent/NO154136C/en unknown
- 1978-11-20 JP JP50015078A patent/JPS54500055A/ja active Pending
- 1978-11-20 WO PCT/US1978/000165 patent/WO1979000309A1/en unknown
- 1978-11-20 FI FI783528A patent/FI69327C/en not_active IP Right Cessation
- 1978-11-20 CA CA316,488A patent/CA1092405A/en not_active Expired
- 1978-11-21 AR AR274523A patent/AR220159A1/en active
-
1979
- 1979-07-19 SE SE7906221A patent/SE422817B/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
AR220159A1 (en) | 1980-10-15 |
FI69327B (en) | 1985-09-30 |
WO1979000309A1 (en) | 1979-06-14 |
NO154136C (en) | 1986-07-23 |
FI783528A (en) | 1979-05-22 |
NO783875L (en) | 1979-05-22 |
CA1092405A (en) | 1980-12-30 |
SE7906221L (en) | 1979-07-19 |
JPS54500055A (en) | 1979-11-08 |
FI69327C (en) | 1986-01-10 |
SE422817B (en) | 1982-03-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US8759467B2 (en) | Polyester polyol, polyurethane, obtained using the same, process for production thereof, and molded polyurethane | |
EP2042535B1 (en) | Method for producing polyurethane and use of polyurethane produced by the same | |
US3377308A (en) | Two-step process for the production of solutions of segmented polyurethane polymers | |
US20050288476A1 (en) | Thermoplastic copolymers through stoichiometric reactions between diisocyanates and oligomeric diols and diamines | |
JP2011214012A (en) | Melt spun tpu fibers and process | |
US3432456A (en) | Polyurethanes prepared from dihydrazides | |
US3359243A (en) | Linear polyurea elastomers | |
KR20090006855A (en) | Segmented polyurethane elastomers with high elongation at tear | |
US3388100A (en) | Polyurethane polymers containing amide and urea groups | |
US3929691A (en) | Solutions of copolymers containing amide and imide groups and process for their preparation | |
NO154136B (en) | PAPER MACHINE WASHING MACHINE O.L. | |
EP0544912A1 (en) | Elastic polyurethane fiber | |
US3557044A (en) | Process for making spandex polymers | |
US3507834A (en) | Filaments of segmented elastomers from sterically hindered tertiary aralkyl diisocyanates and diamines | |
US5834580A (en) | Polyurethanes prepared from amide linkages-containing diamine chain extender | |
JP2717148B2 (en) | Spandex molded products with polycarbonate soft segments | |
US3216975A (en) | Elastomers derived from hydrazino compounds of cyclic diazines | |
CH518328A (en) | Crosslinked polyurethanes for fibre prodn | |
US3541053A (en) | Segmented polyurethanes containing monodisperse hard segments | |
US3379683A (en) | Polyurethanes prepared from m-xylylenediamine | |
KR100196651B1 (en) | An improved process for preparing polyurethane fiber | |
US3496144A (en) | Production of hydrolysis-resistant polyurethane elastomers based on adipic acid; 1,6-hexanediol; 2,2,4-trimethyl-1,3-pentanediol polyesters | |
US3763058A (en) | Polyurethane elastomers with high affinity for dyes | |
US3839284A (en) | Polyurethanes prepared from 2,3,5,6-tetramethyl-p-xylylene diisocyanate | |
CN1694911A (en) | Polyurethaneurea and spandex comprising same |