GB1099372A - Improvements relating to carbohydrate-derived polymers - Google Patents
Improvements relating to carbohydrate-derived polymersInfo
- Publication number
- GB1099372A GB1099372A GB906565A GB906565A GB1099372A GB 1099372 A GB1099372 A GB 1099372A GB 906565 A GB906565 A GB 906565A GB 906565 A GB906565 A GB 906565A GB 1099372 A GB1099372 A GB 1099372A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- galactose
- methyl
- esters
- diketal
- 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
- 229920000642 polymer Polymers 0.000 title abstract 5
- 150000001720 carbohydrates Chemical class 0.000 title 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 6
- 229930182830 galactose Natural products 0.000 abstract 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 4
- 150000002148 esters Chemical class 0.000 abstract 4
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 abstract 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 2
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- 125000005395 methacrylic acid group Chemical group 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 abstract 1
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- RGHNJXZEOKUKBD-MGCNEYSASA-N D-galactonic acid Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-MGCNEYSASA-N 0.000 abstract 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Natural products OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 159000000007 calcium salts Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 abstract 1
- 229940077239 chlorous acid Drugs 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentaoxide Chemical compound [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 239000011953 free-radical catalyst Substances 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 abstract 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 150000003839 salts Chemical group 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
- 239000012279 sodium borohydride Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Saccharide Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Polymers of 1,2:3,4-diketals of galactose esterified in the 6-position with an a ,b -olefinically unsaturated mono- or di-carboxylic acid are prepared by polymerizing the corresponding monomeric ester (see Division C2) in the presence of a free radical catalyst. The ketal residues may then be removed from the polymer by controlled hydrolysis, e.g. in the presence of an aqueous organic acid such as formic acid. The galactose diketal may be esterified with, for example, acrylic, methacrylic, ethacrylic, a -chloroacrylic or a -cyanoacrylic acid, or maleic, fumaric or itaconic acid or their half-esters. The ketal groups may be derived from acetone, methyl ethyl ketone, methyl propyl ketone, monochloroacetone or cyclohexanone. Polymerization can be effected in bulk or in benzene using azobisisobutyronitrile as catalyst. The galactose diketal acrylates or methacrylates may be copolymerized with monomers such as methyl acrylate, methyl methacrylate or acrylonitrile. The polymers after removal of the ketal groups can be converted to acetate, benzoate, phenyl carbamate, phenylhydrazone and phenylosazone derivatives; they may also be nitrated with nitrogen pentoxide, reduced with sodium borohydride to the corresponding polygalactitol-6-ester, and oxidized with chlorous acid to the corresponding galactonic acid polymer (or 1,4-lactone thereof) which can then be neutralized to the salt form, e.g. sodium or calcium salt.ALSO:Esters of an a ,b olefinically unsaturated polymerizable mono- or di-carboxylic acid and the hydroxyl group in the six position of galactose, specifically diisopropylidene galactose 6-methacrylate and acrylate are novel compounds and are prepared by reacting a ketone with galactose to form a 1,2:3,4-diketal and then reacting with the unsaturated acid. Acids specified are acrylic, methacrylic, a -chloroacrylic, a -cyanoacrylic, maleic, half esters of maleic or fumaric, a -ethacrylic, itaconic and half esters thereof, and the ketones may be acetone, methyl ethyl ketone, methyl propyl ketone, mono-chloracetone, and cyclohexanone, and a polymerization inhibitor may be present.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB906565A GB1099372A (en) | 1965-03-03 | 1965-03-03 | Improvements relating to carbohydrate-derived polymers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB906565A GB1099372A (en) | 1965-03-03 | 1965-03-03 | Improvements relating to carbohydrate-derived polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1099372A true GB1099372A (en) | 1968-01-17 |
Family
ID=9864724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB906565A Expired GB1099372A (en) | 1965-03-03 | 1965-03-03 | Improvements relating to carbohydrate-derived polymers |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1099372A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0237132A3 (en) * | 1986-03-13 | 1987-12-02 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of water-soluble saccharide polymers |
| EP0237131A3 (en) * | 1986-03-13 | 1987-12-02 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of water-soluble saccharide polymers |
| EP0251348A1 (en) * | 1986-05-01 | 1988-01-07 | Shell Internationale Researchmaatschappij B.V. | Water-soluble saccharide polymers |
| EP0180262A3 (en) * | 1984-10-26 | 1989-02-01 | Shell Internationale Researchmaatschappij B.V. | A process for the preparation of water soluble vinyl saccharide polymers. |
| WO2005063833A1 (en) * | 2003-12-31 | 2005-07-14 | Council Of Scientific And Industrial Research | Oligomers containing n-acetyl glucosamine |
| US6977285B2 (en) | 2004-03-30 | 2005-12-20 | Council Of Scientific And Industrial Research | Oligomers containing N-acetyl glucosamine (NAG) |
| US8871512B2 (en) | 2010-10-27 | 2014-10-28 | Empire Technology Development Llc | Biocompatible polymerizable acrylate products and methods |
| US9174871B2 (en) | 2012-11-02 | 2015-11-03 | Empire Technology Development Llc | Cement slurries having pyranose polymers |
| US9212245B2 (en) | 2012-12-04 | 2015-12-15 | Empire Technology Development Llc | High performance acrylamide adhesives |
| US9238774B2 (en) | 2012-11-02 | 2016-01-19 | Empire Technology Development Llc | Soil fixation, dust suppression and water retention |
-
1965
- 1965-03-03 GB GB906565A patent/GB1099372A/en not_active Expired
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0180262A3 (en) * | 1984-10-26 | 1989-02-01 | Shell Internationale Researchmaatschappij B.V. | A process for the preparation of water soluble vinyl saccharide polymers. |
| EP0237132A3 (en) * | 1986-03-13 | 1987-12-02 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of water-soluble saccharide polymers |
| EP0237131A3 (en) * | 1986-03-13 | 1987-12-02 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of water-soluble saccharide polymers |
| EP0251348A1 (en) * | 1986-05-01 | 1988-01-07 | Shell Internationale Researchmaatschappij B.V. | Water-soluble saccharide polymers |
| WO2005063833A1 (en) * | 2003-12-31 | 2005-07-14 | Council Of Scientific And Industrial Research | Oligomers containing n-acetyl glucosamine |
| US6977285B2 (en) | 2004-03-30 | 2005-12-20 | Council Of Scientific And Industrial Research | Oligomers containing N-acetyl glucosamine (NAG) |
| US8871512B2 (en) | 2010-10-27 | 2014-10-28 | Empire Technology Development Llc | Biocompatible polymerizable acrylate products and methods |
| US9428532B2 (en) | 2010-10-27 | 2016-08-30 | Empire Technology Development Llc | Methods for making biocompatible polymerizable acrylate products |
| US9174871B2 (en) | 2012-11-02 | 2015-11-03 | Empire Technology Development Llc | Cement slurries having pyranose polymers |
| US9238774B2 (en) | 2012-11-02 | 2016-01-19 | Empire Technology Development Llc | Soil fixation, dust suppression and water retention |
| US9212245B2 (en) | 2012-12-04 | 2015-12-15 | Empire Technology Development Llc | High performance acrylamide adhesives |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES405771A1 (en) | Sustained release polymers | |
| GB877243A (en) | Carbonatoalkyl acrylates and methacrylates and method for preparing same | |
| GB834346A (en) | Impact-resistant synthetic resinous compositions | |
| GB762953A (en) | Improvements in and relating to the polymerization of organic compounds with high energy electrons | |
| GB1291107A (en) | Coating composition and process for preparing the same | |
| GB1099372A (en) | Improvements relating to carbohydrate-derived polymers | |
| GB1209108A (en) | Emulsion production | |
| GB1102746A (en) | Process for the production of copolymers of vinyl esters and ethylene | |
| GB1249390A (en) | Copolymers of vinylesters | |
| FR1381751A (en) | Dental prostheses by the "powder-liquid process" with a mixture of methyl methacrylate monomers and (meth) acrylic esters with oh alcoholic groups | |
| GB1277791A (en) | Polymerisable amido-containing ethylenically unsaturated ester monomers and polymers thereof | |
| GB1280008A (en) | Process for grafting unsaturated acids or esters on polyethylene | |
| SE7613949L (en) | FINE-PERCOME COPOLYMER DISPERSIONS AND PROCEDURES FOR THEIR PREPARATION | |
| GB1314078A (en) | Resinuous compositions | |
| GB1060711A (en) | The preparation of hydroxyl-containing copolymers | |
| GB982577A (en) | Polymers containing phosphorus and a process for preparing them | |
| GB1156424A (en) | A Process for the Production of Cast Sheets from Methyl Methacrylate | |
| JPS5516053A (en) | Resin usable for processing e.g. paper conversion | |
| GB944359A (en) | Process for the preparation of polymers of unsaturated aldehydes by radiation | |
| GB498383A (en) | Manufacture of solutions of highly polymeric substances | |
| ES343299A1 (en) | Improvements in or relating to Polymeric Compositions | |
| GB1110266A (en) | Substituted acrylates and polymers thereof | |
| JPS5379981A (en) | Preparation of polymer emulsion | |
| GB869867A (en) | Method for preparing polymeric anhydrides and polymeric acyl halides | |
| GB1128467A (en) | Methacrylate esters and compositions containing these |