GB745896A - Improvements relating to cellulose acetate compositions - Google Patents
Improvements relating to cellulose acetate compositionsInfo
- Publication number
- GB745896A GB745896A GB2498751A GB2498751A GB745896A GB 745896 A GB745896 A GB 745896A GB 2498751 A GB2498751 A GB 2498751A GB 2498751 A GB2498751 A GB 2498751A GB 745896 A GB745896 A GB 745896A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulpholanyl
- ethers
- sulpholauryl
- plasticizers
- esters
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229920002301 cellulose acetate Polymers 0.000 title abstract 5
- 239000000203 mixture Substances 0.000 title abstract 5
- -1 sulpholauryl Chemical class 0.000 abstract 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- 239000004014 plasticizer Substances 0.000 abstract 6
- 150000002170 ethers Chemical class 0.000 abstract 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 4
- MBDNRNMVTZADMQ-UHFFFAOYSA-N sulfolene Chemical compound O=S1(=O)CC=CC1 MBDNRNMVTZADMQ-UHFFFAOYSA-N 0.000 abstract 4
- AMXKVIWWXBYXRS-UHFFFAOYSA-N 1,1-dioxothiolan-3-ol Chemical compound OC1CCS(=O)(=O)C1 AMXKVIWWXBYXRS-UHFFFAOYSA-N 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 150000002576 ketones Chemical class 0.000 abstract 3
- QDRZGXHVBINHCR-UHFFFAOYSA-N 1,1-dioxothiolan-2-ol Chemical compound OC1CCCS1(=O)=O QDRZGXHVBINHCR-UHFFFAOYSA-N 0.000 abstract 2
- QAAMMQJXNSQLHE-UHFFFAOYSA-N 2-(1,1-dioxothiolan-2-yl)acetic acid Chemical compound OC(=O)CC1CCCS1(=O)=O QAAMMQJXNSQLHE-UHFFFAOYSA-N 0.000 abstract 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 238000000465 moulding Methods 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical class O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 abstract 2
- UXROCMRQMCSWEY-UHFFFAOYSA-N (1,1-dioxothiolan-2-yl) benzoate Chemical compound C(C1=CC=CC=C1)(=O)OC1S(=O)(=O)CCC1 UXROCMRQMCSWEY-UHFFFAOYSA-N 0.000 abstract 1
- GWSNLFQROYMISK-UHFFFAOYSA-N 1,1-dioxothiolane-2,2-diol Chemical compound OC1(S(=O)(=O)CCC1)O GWSNLFQROYMISK-UHFFFAOYSA-N 0.000 abstract 1
- KPZLTKNAKAIBKM-UHFFFAOYSA-N 1-(1,1-dioxothiolan-2-yl)propan-2-one Chemical compound CC(=O)CC1CCCS1(=O)=O KPZLTKNAKAIBKM-UHFFFAOYSA-N 0.000 abstract 1
- CTWMTKXAHVOJMD-UHFFFAOYSA-N 1-acetyloxydodecane-3-sulfonic acid Chemical compound C(C)(=O)OCCC(CCCCCCCCC)S(=O)(=O)O CTWMTKXAHVOJMD-UHFFFAOYSA-N 0.000 abstract 1
- QZVQJQAJJYKLHY-UHFFFAOYSA-N 1-benzoyloxydodecane-3-sulfonic acid Chemical compound C(C1=CC=CC=C1)(=O)OCCC(CCCCCCCCC)S(=O)(=O)O QZVQJQAJJYKLHY-UHFFFAOYSA-N 0.000 abstract 1
- KVOQKLVBMUSEJU-UHFFFAOYSA-N 14-methoxy-1-(14-methoxy-3-sulfotetradecoxy)tetradecane-3-sulfonic acid Chemical class COCCCCCCCCCCCC(CCOCCC(CCCCCCCCCCCOC)S(=O)(=O)O)S(=O)(=O)O KVOQKLVBMUSEJU-UHFFFAOYSA-N 0.000 abstract 1
- UCNXJEZGUNAERT-UHFFFAOYSA-N 14-oxopentadecane-1-sulfonic acid Chemical class S(=O)(=O)(O)CCCCCCCCCCCCCC(C)=O UCNXJEZGUNAERT-UHFFFAOYSA-N 0.000 abstract 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 abstract 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 abstract 1
- ZURHUFGDUGVBAZ-UHFFFAOYSA-N 2-ethyl-3-methylperoxythiolane 1,1-dioxide Chemical compound C(C)C1S(=O)(=O)CCC1OOC ZURHUFGDUGVBAZ-UHFFFAOYSA-N 0.000 abstract 1
- OIPVZGSYIJYEGU-UHFFFAOYSA-N 4-chloro-1,1-dioxothiolan-3-ol Chemical compound OC1CS(=O)(=O)CC1Cl OIPVZGSYIJYEGU-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 abstract 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 1
- HGYDIDRPHBTJPS-UHFFFAOYSA-N C(CCC)(=O)OC1S(=O)(=O)CCC1 Chemical compound C(CCC)(=O)OC1S(=O)(=O)CCC1 HGYDIDRPHBTJPS-UHFFFAOYSA-N 0.000 abstract 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 abstract 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 abstract 1
- HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 abstract 1
- 239000000020 Nitrocellulose Substances 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 abstract 1
- 229920003086 cellulose ether Polymers 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 abstract 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 abstract 1
- 239000011888 foil Substances 0.000 abstract 1
- 150000002334 glycols Chemical class 0.000 abstract 1
- 230000000887 hydrating effect Effects 0.000 abstract 1
- 239000004922 lacquer Substances 0.000 abstract 1
- 229940070765 laurate Drugs 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000002763 monocarboxylic acids Chemical class 0.000 abstract 1
- 229920001220 nitrocellulos Polymers 0.000 abstract 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 abstract 1
- 239000012188 paraffin wax Substances 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 229920002689 polyvinyl acetate Polymers 0.000 abstract 1
- 239000011118 polyvinyl acetate Substances 0.000 abstract 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/45—Heterocyclic compounds having sulfur in the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention comprises compositions of cellulose acetate of at least 52 per cent acetic acid content with beta-monoacylmethylene sulpholanes or similar b -esters or ethers, (see Group IV (b)), as plasticizers. In examples, films are cast from acetone solutions of cellulose acetate especially triacetate with various proportions of sulpholauryl acetone, and sulpholauryl derivatives of other aliphatic ketones, and acetophenone; 3-sulpholauryl acetate, butyrate, and derivatives of aliphatic acids up to 5 C atoms; 3-sulpholauryl benzoate in conjunction with alkyl phthalate, phosphate and glycolate plasticizers; methoxyethyl-3-sulpholauryl ethers, and other sulpholauryl aliphatic ethers containing either groups of up to 5 C atoms, and diethers such as the ethoxy ethyl-, and phenyl ether in conjunction with other plasticizers. The plasticizers may also be used in making sheets by block process, moulding compositions, and lacquers, and in proportions of about 20 to 80 per cent. The Provisional Specification refers also to sulpholauryl products from other ketones, and other ethers and esters, and other derivatives, which may be used for plasticizing cellulose nitrate and cellulose ethers; and to the use of these compounds as plasticizers &c. for acetone-soluble polymers and co-polymers including polyvinyl acetate, acrylates, vinyl chloride, vinylidene chloride, acrylonitrile, vinyl acetate and isopropenyl acetate. This subject-matter does not occur in the Specification as accepted.ALSO:The invention comprises compositions of cellulose acetate of at least 52 per cent acetic acid content with b -mono-acyl-methylene sulpholanes, or similar b -esters or ethers, as plasticizers. The sulpholane derivatives may be made by the condensation of 3-sulpholene with ketones, esterifying 3-sulpholanol (obtained by hydrating sulpholene), with acids, especially paraffin monocarboxylic acids and by etherifying sulpholanol with alcohols or ethers of glycols. In examples, the preparation is described of sulpholanyl acetone, from sulpholene and acetone, sulpholanyl butyrate from 3-sulpholanol and n butyric anhydride, sulpholanyl benzoate, from sulpholanol and benzoyl chloride, methoxy ethyl-3-sulpholanyl ether from 3-sulpholene and monomethyl ether of ethylene glycol, and also a phenyl ether of 3-sulpholanol; a number of other esters and ethers and ketone derivatives are specified. The products are incorporated into cellulose acetate compositions for making foils, mouldings, &c. The Provisional Specification refers also to sulpholanyl products from nitromethane, diethyl malonate, with hydrolysis to sulpholanyl acetic acid, ethyl cyanoacetate, with hydrolysis to sulpholanyl acetic acid, and the esters of this with alcohols; the preparation of 3-sulpholanyl - 2 - ethyl - hexoate is described; other sulpholanyl esters including the laurate, and derivatives substituted at the 3 and 4 C-atoms including diesters and diethers of 3 : 4 dihydroxysulpholane, and a 3-hydroxy-4-chlorosulpholane are included.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2498751A GB745896A (en) | 1951-10-25 | 1951-10-25 | Improvements relating to cellulose acetate compositions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2498751A GB745896A (en) | 1951-10-25 | 1951-10-25 | Improvements relating to cellulose acetate compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB745896A true GB745896A (en) | 1956-03-07 |
Family
ID=10220381
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2498751A Expired GB745896A (en) | 1951-10-25 | 1951-10-25 | Improvements relating to cellulose acetate compositions |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB745896A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3532527A (en) * | 1966-11-04 | 1970-10-06 | Dow Chemical Co | Permeable separatory membranes |
-
1951
- 1951-10-25 GB GB2498751A patent/GB745896A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3532527A (en) * | 1966-11-04 | 1970-10-06 | Dow Chemical Co | Permeable separatory membranes |
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