NO143826B - DIAGNOSTIZING AGENT, PRINCIPLES IN THE FORM OF A TEST STRIP, FOR DETECTION OF ACET-ACETIC ACID IN BIOLOGICAL LIQUIDS - Google Patents
DIAGNOSTIZING AGENT, PRINCIPLES IN THE FORM OF A TEST STRIP, FOR DETECTION OF ACET-ACETIC ACID IN BIOLOGICAL LIQUIDS Download PDFInfo
- Publication number
- NO143826B NO143826B NO742323A NO742323A NO143826B NO 143826 B NO143826 B NO 143826B NO 742323 A NO742323 A NO 742323A NO 742323 A NO742323 A NO 742323A NO 143826 B NO143826 B NO 143826B
- Authority
- NO
- Norway
- Prior art keywords
- diagnostizing
- acet
- agent
- principles
- detection
- Prior art date
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title description 4
- 239000007788 liquid Substances 0.000 title description 3
- 239000003795 chemical substances by application Substances 0.000 title description 2
- 238000001514 detection method Methods 0.000 title 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 13
- -1 polyoxymethylenes Polymers 0.000 claims description 13
- BPGDAMSIGCZZLK-UHFFFAOYSA-N acetyloxymethyl acetate Chemical compound CC(=O)OCOC(C)=O BPGDAMSIGCZZLK-UHFFFAOYSA-N 0.000 claims description 12
- 229920006324 polyoxymethylene Polymers 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229930040373 Paraformaldehyde Natural products 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000012345 acetylating agent Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- 238000009825 accumulation Methods 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000003413 degradative effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/64—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving ketones
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/20—Oxygen containing
- Y10T436/200833—Carbonyl, ether, aldehyde or ketone containing
Description
Fremgangsmåte til å stabilisere polyoxymethylener rnot varme. Process for stabilizing polyoxymethylenes without heat.
Foreliggende oppfinnelse angår polyoxymethylener som er stabilisert mot varme, hvilke er nyttige termoplastiske materialer, samt deres fremstilling ved acetylering av polymerens ende-hydroxy-grupper med methylenglycoldiacetat. The present invention relates to polyoxymethylenes which are stabilized against heat, which are useful thermoplastic materials, as well as their production by acetylating the terminal hydroxy groups of the polymer with methylene glycol diacetate.
Oppfinnelsen skaffer en fremgangsmåte til fremstilling av polyoxymethylener som er stabilisert mot varme, hvilken fremgangsmåte omfatter transforestring av polyoxymethylenene med overskudd av methylenglycoldiacetat ved en temperatur mellom 170 og 210° C. Det foretrukne vektforhold mellom polymer og acetyle-ringsmiddel er fra 1:5 til 1:15, og de nød-vendige reaksjonstider er mindre enn 3 timer. The invention provides a method for the production of polyoxymethylenes that are stabilized against heat, which method comprises transesterification of the polyoxymethylenes with an excess of methylene glycol diacetate at a temperature between 170 and 210° C. The preferred weight ratio between polymer and acetylating agent is from 1:5 to 1 :15, and the necessary reaction times are less than 3 hours.
En hurtig og fullstendig oppløsning av polymeren inntreffer ved disse temperatu-rer, og en hurtig acetylering ved transforestring bevirkes. A rapid and complete dissolution of the polymer occurs at these temperatures, and a rapid acetylation by transesterification is effected.
Det er funnet at methylenglycoldiacetat er å foretrekke som acetyleringsimiddel fremfor eddiksyreanhydrid da spaltningen av den behandlede polymer herved blir mindre. Dette illustreres i tabell 1, hvor der er gjengitt eksempler på acetylering ved bruk av begge aoetyleringsmidler og de samme eksperimentelle betingelser. It has been found that methylene glycol diacetate is preferable as an acetylating agent to acetic anhydride as the cleavage of the treated polymer is thereby reduced. This is illustrated in table 1, where examples of acetylation using both aoethylating agents and the same experimental conditions are reproduced.
For de nevnte forsøk ble der fremstillet produkter med varierende omfang av mo-lekylkompleksene. Noen av produktene ble fremstillet ved polymeriseringsmetoden i gassfase ved hjelp av en topokjemisk reaksjon som beskrevet i italiensk patent nr. 626 461 (produkt 3 og 4) og andre ved poly-merisering i vandig oppløsning som beskrevet i italiensk patent 646 437 (produkt 1 og 2). De reduserte viskositeter (j.iS|l/C) ble målt i dimethylformamid ved 150° C. For the aforementioned experiments, products with varying extents of the molecular complexes were produced. Some of the products were produced by the polymerization method in the gas phase using a topochemical reaction as described in Italian patent no. 626 461 (product 3 and 4) and others by polymerization in aqueous solution as described in Italian patent 646 437 (product 1 and 2). The reduced viscosities (j.iS|l/C) were measured in dimethylformamide at 150°C.
Ved betraktning av de tabellariserte data ser man at produktene stabilisert med methylenglycoldiacetat oppviser en viskositet som er 5—30 pst. høyere enn viskositeten av de produkter som er stabilisert med eddiksyreanhydrid, og at jo høyere viskositeten er, desto større er for-bedringen. When considering the tabulated data, it can be seen that the products stabilized with methylene glycol diacetate exhibit a viscosity that is 5-30 per cent higher than the viscosity of the products stabilized with acetic anhydride, and that the higher the viscosity, the greater the improvement.
Et ytterligere bevis for at methylenglycoldiacetat er et mer skånsomt reagens og i mindre grad bevirker avbyggende bi-reaksjoner i den polymere illustreres i tabell 2, hvori verdiene av de reduserte viskositeter for to forskjellige polymere som er stabilisert med de to reagenser ved 170° C, er gjengitt efter økende tidsrom. Further proof that methylene glycol diacetate is a gentler reagent and causes less degradative side-reactions in the polymer is illustrated in Table 2, in which the values of the reduced viscosities for two different polymers stabilized with the two reagents at 170°C, are reproduced after increasing time periods.
Utbyttet av produktene stabilisert med methylenglycoldiacetat forbedres bemer-kelsesverdig når stabiliseringen bevirkes i nærvær av små mengder, fra 0,5 til 3 pst. av keten. Forbedrede utbytter av de ace-tylerte produkter oppnåes også når eddiksyreanhydrid tilsettes i mengder fra 3 til 30 pst. The yield of the products stabilized with methylene glycol diacetate is remarkably improved when the stabilization is effected in the presence of small amounts, from 0.5 to 3 percent, of the ketene. Improved yields of the acetylated products are also obtained when acetic anhydride is added in amounts from 3 to 30 per cent.
Utbyttene økes når begge midler be-nyttes sammen. Dette illustreres i tabellene 3, 4 og 5, hvori produkt 2 i tabell 1 er an-vendt. The dividends are increased when both funds are used together. This is illustrated in tables 3, 4 and 5, in which product 2 in table 1 is used.
For i praksis å utføre fremgangsmåten ifølge foreliggende oppfinnelse behandles et polyoxymethylendihydroxyd fremstillet ved en hvilkensomhelst egnet fremgangsmåte og av en hvilkensomhelst polymeri-seringsgrad, med ca. 10 vektsdeler methylenglycoldiacetat eller med blandinger der-av med de lavere ledd av serien av poly-oxymethylendiacetat-homologe og oppvarmes til 170—175° C i en autoklav som vip-pes eller omrøres. For produkter med me-get høy molekylvekt, som ikke er fullstendig oppløselige ved 170° C, utføres stabiliseringen ved en høyere temperatur, opp til 200—210° C. Temperaturen bibeholdes i 5—15 minutter fra det tidspunkt da produktet er fullstendig oppløst. Reaksjons-blandingen får avkjøles til romtemperatur, sentrifugeres så, vaskes dersom dette øn-skes, med en inert organisk væske, og tør-res tilslutt fortrinsvis under vakuum. In order to practically carry out the method according to the present invention, a polyoxymethylene dihydroxide produced by any suitable method and of any degree of polymerization is treated with approx. 10 parts by weight of methylene glycol diacetate or with mixtures thereof with the lower links of the series of polyoxymethylene diacetate homologues and heated to 170-175° C in an autoclave which is tilted or stirred. For products with a very high molecular weight, which are not completely soluble at 170° C, the stabilization is carried out at a higher temperature, up to 200-210° C. The temperature is maintained for 5-15 minutes from the time when the product is completely dissolved. The reaction mixture is allowed to cool to room temperature, then centrifuged, washed, if desired, with an inert organic liquid, and finally dried preferably under vacuum.
Utførelsen skjer under de samme betingelser når methylengiycoldiacetatene som anvendes inneholder keten og/eller eddiksyreanhydrid. The execution takes place under the same conditions when the methylene glycol diacetates used contain ketene and/or acetic anhydride.
Den gjenvundne væske beholder egen-skapene til acetyleringsmidlet. For å unn- gå opphopning i dette av eddiksyre dannet ved hydrolyse av acetater, forårsaket av vannet som utgjør endegruppene av hvert ledd av serien av polyoxyimethylen-diacetat-homologe, kan en tilsvarende mengde keten tilsettes f. eks. periodevis. The recovered liquid retains the properties of the acetylating agent. In order to avoid accumulation in this of acetic acid formed by hydrolysis of acetates, caused by the water which forms the end groups of each member of the series of polyoxyimethylene diacetate homologues, a corresponding amount of ketene can be added, e.g. periodically.
Eddiksyreanhydrid må også tilsettes periodevis for å unngå en uønsket opphopning av høyere ledd i polyoxymethylendi-acetatserien dannet ved addisjon av for-maldehyd som avspaltes fra produktene som stabiliseres: Acetic anhydride must also be added periodically to avoid an unwanted accumulation of higher links in the polyoxymethylene diacetate series formed by the addition of formaldehyde which splits off from the products that are stabilized:
Eksempel 1. 30 g polyoxymethylendihydroxyd, fremstillet ved topokjemisk reaksjon ifølge fremgangsmåten beskrevet 1 italiensk patent nr. 626 461, og 300 g methylenglycoldiacetat med kokepunkt i området mellom 166 og 173° C, anbringes for et tidsrom av 20 minutter i en glassautoklav. Ved produk-tets koketemperatur oppløses dette innen 10 minutter. Det får avkjøles langsomt til romtemperatur i løpet av ca. 2 timer. Det filtreres under vakuum og vaskes gjen-tagne ganger med benzen, idet der anvendes en total benzenmengde tilsvarende den dobbelte vekt av polyoxymethylendi-hydroxydet. 28,5 g tørt produkt erholdes, nemlig 95 pst. av det teoretiske. Example 1. 30 g of polyoxymethylene dihydroxide, produced by topochemical reaction according to the method described in Italian patent no. 626 461, and 300 g of methylene glycol diacetate with a boiling point in the range between 166 and 173° C, are placed for a period of 20 minutes in a glass autoclave. At the product's boiling temperature, this dissolves within 10 minutes. It is allowed to cool slowly to room temperature during approx. 2 hours. It is filtered under vacuum and washed repeatedly with benzene, using a total amount of benzene corresponding to twice the weight of the polyoxymethylene dihydroxide. 28.5 g of dry product is obtained, namely 95 per cent of the theoretical.
Den termiske stabilitet av dette og andre produkter erholdt ved fremgangsmåten ifølge foreliggende oppfinnelse ble målt ved oppvarmning av ca. 0,5 g av produktet ved 215° C i 30 minutter. Resulta-tene er uttrykt ved den kinetiske depoly-merisasjonskonstant (K^l5) som er definert som vekttapet pr. minutt beregnet pr. 100 g utgangspolymer. For dette produkt ble K.,l5 funnet å være 0,1. Den reduserte viskositet målt i dimethylformamid ved 150° C i 0,5 pst. konsentrasjon hie funnet å være 3,4. The thermal stability of this and other products obtained by the method according to the present invention was measured by heating approx. 0.5 g of the product at 215° C for 30 minutes. The results are expressed by the kinetic depolymerization constant (K^l5), which is defined as the weight loss per minute calculated per 100 g of starting polymer. For this product, K 15 was found to be 0.1. The reduced viscosity measured in dimethylformamide at 150°C in 0.5% concentration was found to be 3.4.
Eksempel 2. Example 2.
20 g polyoxymethylendihydroxyd, fremstillet ved fremgangsmåten beskrevet i italiensk patent nr. 646 437, behandles med 200 g methylenglycoldiacetat under samme betingelser som i eksempel 1 hva angår både stabiliseringsreaksjonen og de etterfølgende vaske- og tørreoperasjoner. 15,6 g tørt produkt erholdes, hvilket tilsvarer et utbytte av acetylert produkt på 78 20 g of polyoxymethylene dihydroxide, produced by the method described in Italian patent no. 646 437, is treated with 200 g of methylene glycol diacetate under the same conditions as in example 1 as regards both the stabilization reaction and the subsequent washing and drying operations. 15.6 g of dry product is obtained, which corresponds to a yield of acetylated product of 78
pst. For dette produkt ble de følgende ver-dier oppnådd: K. >iri = 0,05; redusert viskositet = 0,93. wt. For this product the following values were obtained: K. >iri = 0.05; reduced viscosity = 0.93.
Eksempel 3. 30 g av produktet fremstillet ved fremgangsmåten beskrevet i italiensk patent nr. 626 461 og 300 g methylenglycoldiacetat inneholdende i oppløsning de første ledd av den homologe serie av poiy-oxymethylendlacetater, hvori antall oxy-methylengrupper er større enn 1 og mindre enn 10, og som derfor har et kokepunkt ved 2 rnm i området mellom 45 og 120° C, oppvarmes i en glassautoklav ved 170°C for et tidsromav20 minutter. Denne temperatur bibeholdes i 30 minutter, der-efter avkjøles autøklaven og produktet filtreres og tørres som i de foregående eksempler. 26,4 g av polymeren erholdes, hvilket tilsvarer et utbytte på 88 pst. K.,,.-= 0,08. Redusert viskositet, målt som an-gitt i de foregående eksempler, var 1,05. i Example 3. 30 g of the product produced by the method described in Italian patent no. 626 461 and 300 g of methylene glycol diacetate containing in solution the first members of the homologous series of polyoxymethylene acetates, in which the number of oxymethylene groups is greater than 1 and less than 10 , and which therefore has a boiling point at 2 rnm in the range between 45 and 120° C, is heated in a glass autoclave at 170° C for a period of 20 minutes. This temperature is maintained for 30 minutes, after which the autoclave is cooled and the product is filtered and dried as in the previous examples. 26.4 g of the polymer is obtained, which corresponds to a yield of 88 percent K.,,.-= 0.08. Reduced viscosity, measured as indicated in the previous examples, was 1.05. in
Claims (3)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP48125667A JPS5143796B2 (en) | 1973-11-08 | 1973-11-08 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO742323L NO742323L (en) | 1975-06-02 |
| NO143826B true NO143826B (en) | 1981-01-05 |
| NO143826C NO143826C (en) | 1981-04-15 |
Family
ID=14915665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO742323A NO143826C (en) | 1973-11-08 | 1974-06-26 | DIAGNOSTIZING AGENT, PRINCIPLES IN THE FORM OF A TEST STRIP, FOR DETECTION OF ACET-ACETIC ACID IN BIOLOGICAL LIQUIDS |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3880590A (en) |
| JP (1) | JPS5143796B2 (en) |
| BE (1) | BE816926A (en) |
| CA (1) | CA1021237A (en) |
| CH (1) | CH587491A5 (en) |
| DE (1) | DE2432753C3 (en) |
| DK (1) | DK142296B (en) |
| ES (1) | ES427803A1 (en) |
| FR (1) | FR2250999B1 (en) |
| GB (1) | GB1451268A (en) |
| IT (1) | IT1016633B (en) |
| NL (1) | NL162478C (en) |
| NO (1) | NO143826C (en) |
| SE (1) | SE397733B (en) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2721681B2 (en) * | 1977-05-13 | 1981-05-07 | Behringwerke Ag, 3550 Marburg | Control solution for diagnostic methods of detection of substances contained in urine |
| US4147514A (en) * | 1977-11-21 | 1979-04-03 | Miles Laboratories, Inc. | Test means and method for detecting ketone bodies |
| DE3011168A1 (en) * | 1980-03-22 | 1981-10-01 | Behringwerke Ag, 3550 Marburg | DIAGNOSTIC AGENT FOR DETECTING KETONE BODIES |
| US4440724A (en) * | 1982-11-01 | 1984-04-03 | Helena Laboratories Corporation | Composition for detecting ketone bodies and method of preparation |
| US5071769A (en) * | 1986-12-22 | 1991-12-10 | Abbott Laboratories | Method and device for ketone measurement |
| US4970172A (en) * | 1986-12-22 | 1990-11-13 | Abbott Laboratories | Method and device for ketone measurements |
| US4931404A (en) * | 1986-12-22 | 1990-06-05 | Abbott Laboratories | Method and device for ketone measurement |
| US6149865A (en) * | 1997-07-07 | 2000-11-21 | Teco Diagnostics, Inc. | Test strips for the determination of the ionic strength or specific gravity of an aqueous sample |
| US5922283A (en) * | 1997-07-07 | 1999-07-13 | Teco Diagnostics | Test strips for the determination of the ionic strength or specific gravity of an aqueous sample |
| US6541216B1 (en) | 1999-12-22 | 2003-04-01 | Roche Diagnostics Corporation | Amperometric biosensor test strip |
| US6603403B2 (en) | 2000-12-12 | 2003-08-05 | Kimberly-Clark Worldwide, Inc. | Remote, wetness signaling system |
| US6583722B2 (en) | 2000-12-12 | 2003-06-24 | Kimberly-Clark Worldwide, Inc. | Wetness signaling device |
| US7695975B2 (en) * | 2005-06-23 | 2010-04-13 | Siemens Healthcare Diagnostics Inc. | Detection of adulterated samples |
| AU2013263421A1 (en) * | 2012-05-15 | 2014-12-04 | Invoy Technologies, Llc | Method and apparatus for analyzing acetone in breath |
| EP3757573A4 (en) * | 2018-02-23 | 2021-08-25 | Sysmex Corporation | Specimen for detecting ketone bodies in urine |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2186902A (en) * | 1939-04-07 | 1940-01-09 | Lilly Co Eli | Urine acetone test |
| US2362478A (en) * | 1941-12-24 | 1944-11-14 | Denver Chemical Mfg Company | Reagent for testing for acetone |
| US2509140A (en) * | 1948-03-02 | 1950-05-23 | Miles Lab | Test reagent composition |
| US2577978A (en) * | 1949-02-04 | 1951-12-11 | Miles Lab | Diagnostic composition |
| US2990253A (en) * | 1959-05-21 | 1961-06-27 | Miles Lab | Diagnostic composition |
| NL296257A (en) * | 1962-08-06 | |||
| US3537906A (en) * | 1966-01-05 | 1970-11-03 | Allis Chalmers Mfg Co | Process for producing a fuel cell electrode |
-
1973
- 1973-11-08 JP JP48125667A patent/JPS5143796B2/ja not_active Expired
-
1974
- 1974-06-21 DK DK336474AA patent/DK142296B/en not_active IP Right Cessation
- 1974-06-21 US US481913A patent/US3880590A/en not_active Expired - Lifetime
- 1974-06-26 NO NO742323A patent/NO143826C/en unknown
- 1974-06-26 BE BE145946A patent/BE816926A/en unknown
- 1974-06-27 SE SE7408488A patent/SE397733B/en unknown
- 1974-06-28 ES ES427803A patent/ES427803A1/en not_active Expired
- 1974-07-01 FR FR7422836A patent/FR2250999B1/fr not_active Expired
- 1974-07-08 DE DE2432753A patent/DE2432753C3/en not_active Expired
- 1974-07-11 CA CA204,720A patent/CA1021237A/en not_active Expired
- 1974-07-18 IT IT69297/74A patent/IT1016633B/en active
- 1974-07-19 GB GB3212274A patent/GB1451268A/en not_active Expired
- 1974-08-05 NL NL7410509.A patent/NL162478C/en not_active IP Right Cessation
- 1974-08-20 CH CH1134274A patent/CH587491A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2250999B1 (en) | 1977-10-07 |
| SE7408488L (en) | 1975-05-09 |
| DE2432753A1 (en) | 1975-05-15 |
| CA1021237A (en) | 1977-11-22 |
| DE2432753C3 (en) | 1981-09-10 |
| DK142296B (en) | 1980-10-06 |
| NL7410509A (en) | 1975-05-12 |
| NL162478C (en) | 1980-05-16 |
| BE816926A (en) | 1974-10-16 |
| CH587491A5 (en) | 1977-05-13 |
| NO742323L (en) | 1975-06-02 |
| JPS5143796B2 (en) | 1976-11-24 |
| JPS5078394A (en) | 1975-06-26 |
| US3880590A (en) | 1975-04-29 |
| SE397733B (en) | 1977-11-14 |
| DE2432753B2 (en) | 1981-01-22 |
| DK336474A (en) | 1975-07-14 |
| ES427803A1 (en) | 1977-02-01 |
| IT1016633B (en) | 1977-06-20 |
| NO143826C (en) | 1981-04-15 |
| FR2250999A1 (en) | 1975-06-06 |
| DK142296C (en) | 1981-03-02 |
| AU7061474A (en) | 1976-01-08 |
| GB1451268A (en) | 1976-09-29 |
| NL162478B (en) | 1979-12-17 |
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