GB853886A - Improvements relating to methacrylate polymers - Google Patents
Improvements relating to methacrylate polymersInfo
- Publication number
- GB853886A GB853886A GB29971/58A GB2997158A GB853886A GB 853886 A GB853886 A GB 853886A GB 29971/58 A GB29971/58 A GB 29971/58A GB 2997158 A GB2997158 A GB 2997158A GB 853886 A GB853886 A GB 853886A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methacrylate
- toluene
- ammonia
- monoamine
- copolymers
- 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
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 title abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 12
- 229920001577 copolymer Polymers 0.000 abstract 8
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 abstract 6
- 229910021529 ammonia Inorganic materials 0.000 abstract 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 4
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 abstract 4
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 abstract 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 abstract 3
- QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 abstract 2
- 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 abstract 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 2
- 229910000831 Steel Inorganic materials 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 238000005576 amination reaction Methods 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 238000007334 copolymerization reaction Methods 0.000 abstract 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 abstract 2
- FZJCXIDLUFPGPP-UHFFFAOYSA-N propan-2-ol;toluene Chemical compound CC(C)O.CC1=CC=CC=C1 FZJCXIDLUFPGPP-UHFFFAOYSA-N 0.000 abstract 2
- 239000010959 steel Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- 244000068988 Glycine max Species 0.000 abstract 1
- 235000010469 Glycine max Nutrition 0.000 abstract 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- RKGUHWITAUJTJH-UHFFFAOYSA-N [3-(tert-butylamino)-2-hydroxypropyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CNC(C)(C)C RKGUHWITAUJTJH-UHFFFAOYSA-N 0.000 abstract 1
- 229920000180 alkyd Polymers 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical class CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 235000013305 food Nutrition 0.000 abstract 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 abstract 1
- 239000011521 glass Substances 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 abstract 1
- ZDCHZHDOCCIZIY-UHFFFAOYSA-N phthalic acid;propane-1,2,3-triol Chemical class OCC(O)CO.OC(=O)C1=CC=CC=C1C(O)=O ZDCHZHDOCCIZIY-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 238000005476 soldering Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- 239000005028 tinplate Substances 0.000 abstract 1
Classifications
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
-
- 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
- C08F220/00—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
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F220/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
-
- 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
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Paints Or Removers (AREA)
Abstract
Copolymers of methyl methacrylate are prepared having a relative viscosity of 1,117 to 1,196 and containing in the polymer chain the radical: <FORM:0853886/IV(a)/1> wherein in one R is a hydroxyl group and the other R is an amino residue of ammonia or a monoamine bonded through amino nitrogen, the radical, exclusive of amino residue, constituting 0,2% to 3% by weight of the polymer. The copolymers may be prepared either (1) by copolymerizing methyl methacrylate, glycidyl methacrylate and if desired another ethylenically unsaturated monomer inert towards the above radical, e.g. methyl acrylate, ethyl, propyl and butyl acrylates and methacrylates, lauryl methacrylate, acrylonitrile, vinyl acetate and styrene, and reacting the resulting copolymer with ammonia or a monoamine, or (2) reacting the glycidyl methacrylate with ammonia or a monoamine before the copolymerization and omitting the subsequent amination. The copolymerization and amination take place for a time and under conditions such that a polymer of the desired viscosity is produced, e.g. as described in Specifications 763,158 and 807,895. The examples describe the preparation of copolymers by a solution polymerization process employing benzoyl peroxide or azobisisobutyronitrile as a catalyst. Monoamines specified are dimethylamine, methylethylamine, ethylamine, ethanolamine, diethanolamine, t-butylamine and t-octylamine. The copolymers are used for coating purposes in the form of solutions in solvents such as toluene, toluene-methyl ethyl ketone-butanol, toluene-isopropyl alcohol and toluene-acetone-isopropyl alcohol. Specification 853,885 also is referred to.ALSO:Amino-hydroxypropyl methacrylates are made by reacting ammonia or a monoamine with glycidyl methacrylate, amines specified being ethylamine, t-butylamine, t-octylamine, ethanolamine, diethanolamine, dimethylamine and methylethylamine. In an example (7) 3-t-butylamino-2-hydroxypropyl methacrylate is prepared by adding glycidyl methacrylate to a solution of t-butylamine in water, followed by the removal of water and unreacted amine and distillation and recrystallisation of the ester product. Specifications 763,158, 807,895 and 853,885 are referred to.ALSO:Substrates of steel, tin plate, aluminium or glass are coated with copolymers of methyl, methacrylate having a relative viscosity of 1.117 to 1.196 and containing in the polymer chain the radical: <FORM:0853886/III/1> wherein one R is a hydroxyl group and the other R is an amino residue of ammonia or a monoamine bonded through nitrogen (see Group IV(a)). In examples: (1) the side seams of food cans are coated, shortly after soldering, with a toluene-isopropyl alcohol solution of a methyl methacrylate copolymer in which the amino group in the above radical is derived from ammonia; and (2) steel panels prime coated with a pigmented soya bean oilmodified glycerol phthalate alkyd resin ore coated with a toluene-methyl ethyl ketonebutanol solution of a methyl methacrylate copolymer in which the amino group in the above radical is derived from ethanolamine, followed by baking at 93 DEG C. for 30 minutes. Specifications 763,158, 807,895 and 853,885 are referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB29971/58A GB853886A (en) | 1958-09-18 | 1958-09-18 | Improvements relating to methacrylate polymers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB29971/58A GB853886A (en) | 1958-09-18 | 1958-09-18 | Improvements relating to methacrylate polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB853886A true GB853886A (en) | 1960-11-09 |
Family
ID=10300168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB29971/58A Expired GB853886A (en) | 1958-09-18 | 1958-09-18 | Improvements relating to methacrylate polymers |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB853886A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3114711A (en) * | 1961-03-31 | 1963-12-17 | California Research Corp | Lubricant composition |
| WO2015047196A1 (en) * | 2013-09-26 | 2015-04-02 | Agency For Science, Technology And Research | Polymers for making superhydrophobic surfaces |
| CN113845616A (en) * | 2021-11-04 | 2021-12-28 | 佳易容聚合物(上海)有限公司 | PMMA copolymerized functional resin and preparation method thereof |
-
1958
- 1958-09-18 GB GB29971/58A patent/GB853886A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3114711A (en) * | 1961-03-31 | 1963-12-17 | California Research Corp | Lubricant composition |
| WO2015047196A1 (en) * | 2013-09-26 | 2015-04-02 | Agency For Science, Technology And Research | Polymers for making superhydrophobic surfaces |
| CN113845616A (en) * | 2021-11-04 | 2021-12-28 | 佳易容聚合物(上海)有限公司 | PMMA copolymerized functional resin and preparation method thereof |
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