GB1092884A - Copolymers - Google Patents
CopolymersInfo
- Publication number
- GB1092884A GB1092884A GB23/65A GB2365A GB1092884A GB 1092884 A GB1092884 A GB 1092884A GB 23/65 A GB23/65 A GB 23/65A GB 2365 A GB2365 A GB 2365A GB 1092884 A GB1092884 A GB 1092884A
- Authority
- GB
- United Kingdom
- Prior art keywords
- copolymers
- methacrylate
- trimethyl
- vinyl
- methacrylic acid
- 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
- 229920001577 copolymer Polymers 0.000 title abstract 4
- 239000003054 catalyst Substances 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-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
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 230000002378 acidificating effect Effects 0.000 abstract 2
- -1 alkyl maleates Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 abstract 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 abstract 1
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 abstract 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- 239000004160 Ammonium persulphate Substances 0.000 abstract 1
- 239000004342 Benzoyl peroxide Substances 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
- 229920000877 Melamine resin Polymers 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 abstract 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000004159 Potassium persulphate Substances 0.000 abstract 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 abstract 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Substances CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 abstract 1
- 235000019395 ammonium persulphate Nutrition 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 150000001993 dienes Chemical class 0.000 abstract 1
- 150000002009 diols Chemical class 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 238000012674 dispersion polymerization Methods 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 238000007720 emulsion polymerization reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 abstract 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000003701 inert diluent Substances 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 235000019394 potassium persulphate Nutrition 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 235000011152 sodium sulphate Nutrition 0.000 abstract 1
- PMZURENOXWZQFD-UHFFFAOYSA-L sodium sulphate Substances [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 abstract 1
- 229920001187 thermosetting polymer Polymers 0.000 abstract 1
- 229920001567 vinyl ester resin Polymers 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 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
- 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
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
-
- 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
- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Novel copolymers are derived from 2,2,4-trimethyl - 3 - hydroxypentyl methacrylate as essential component. The methacrylate is copolymerized with one or more other monomers such as styrene and its halogen and alkyl derivatives, vinylnaphthalene and halogen derivatives thereof, acrylonitrile, methacrylonitrile, vinyl esters, vinyl ethers, olefins, dienes, alkyl maleates and fumarates, vinyl and vinylidene halides, and aliphatic, alicyclic, aromatic and heterocyclic esters of acrylic or methacrylic acid. The copolymers may be obtained by dispersion, emulsion or solution polymerization methods using catalysts such as benzoyl, acetyl or hydrogen peroxide, cumene hydroperoxide, sodium, potassium or ammonium persulphate, possibly in a redox system, in some cases in the presence of dodecyl mercaptan. The copolymers are generally thermosetting and form hard films, for which purpose they may be admixed with, for example, melamine-formaldehyde resins.ALSO:2,2,4 - Trimethyl - 3 - hydroxypentyl methacrylate may be prepared by heating 2,2,4-trimethyl - 1,3 - pentanediol with methyl methacrylate in the presence of acidic or basic catalysts, e.g. sodium methoxide, optionally at reduced pressure and/or in the presence of excess methyl methacrylate or of an inert diluent, or by esterifying the aforementioned diol with methacrylic acid using an acidic catalyst. In either method an inhibitor such as hydroquinone is added to prevent polymerization. An example of the former method is given, the monomethacrylate ester being separated from dimethacrylate formed by distillation.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33566864A | 1964-01-03 | 1964-01-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1092884A true GB1092884A (en) | 1967-11-29 |
Family
ID=23312766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23/65A Expired GB1092884A (en) | 1964-01-03 | 1965-01-01 | Copolymers |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1432588A (en) |
| GB (1) | GB1092884A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5290602A (en) * | 1992-10-19 | 1994-03-01 | Union Carbide Chemicals & Plastics Technology Corporation | Hindered-hydroxyl functional (meth) acrylate-containing copolymers particularly suitable for use in coating compositions which are sprayed with compressed fluids as viscosity reducing diluents |
| EP0594109A1 (en) * | 1992-10-19 | 1994-04-27 | Union Carbide Chemicals & Plastics Technology Corporation | Hindered-hydroxyl functional (meth)acrylate esters, copolymers containing them and compositions including same |
| EP0646047A4 (en) * | 1991-04-19 | 1995-05-17 | Basf Corp | Etch-resistant coating. |
| US5420341A (en) * | 1992-10-19 | 1995-05-30 | Union Carbide Chemicals & Plastics | Hindered-hydroxyl functional (meth)acrylate compounds and processes for the preparation thereof |
| US5442023A (en) * | 1994-06-30 | 1995-08-15 | Union Carbide Chemicals & Plastics Technology Corporation | Hindered-hydroxyl functional (meth)acrylate monomers containing di(meth)acrylates and compositions including same |
| WO2003000434A1 (en) * | 2001-06-21 | 2003-01-03 | Basf Corporation | Basecoat composition comprising a poly(meth)acrylate binder |
| WO2003027198A1 (en) * | 2001-09-27 | 2003-04-03 | Basf Corporation | Acryl clearcoat refinish composition |
-
1964
- 1964-12-30 FR FR344A patent/FR1432588A/en not_active Expired
-
1965
- 1965-01-01 GB GB23/65A patent/GB1092884A/en not_active Expired
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0646047A4 (en) * | 1991-04-19 | 1995-05-17 | Basf Corp | Etch-resistant coating. |
| US5290602A (en) * | 1992-10-19 | 1994-03-01 | Union Carbide Chemicals & Plastics Technology Corporation | Hindered-hydroxyl functional (meth) acrylate-containing copolymers particularly suitable for use in coating compositions which are sprayed with compressed fluids as viscosity reducing diluents |
| EP0594109A1 (en) * | 1992-10-19 | 1994-04-27 | Union Carbide Chemicals & Plastics Technology Corporation | Hindered-hydroxyl functional (meth)acrylate esters, copolymers containing them and compositions including same |
| JPH06199953A (en) * | 1992-10-19 | 1994-07-19 | Union Carbide Chem & Plast Technol Corp | Copolymer containing hindered-hydroxyl-functional (meth)acrylate and composition containing same |
| US5420341A (en) * | 1992-10-19 | 1995-05-30 | Union Carbide Chemicals & Plastics | Hindered-hydroxyl functional (meth)acrylate compounds and processes for the preparation thereof |
| US5442023A (en) * | 1994-06-30 | 1995-08-15 | Union Carbide Chemicals & Plastics Technology Corporation | Hindered-hydroxyl functional (meth)acrylate monomers containing di(meth)acrylates and compositions including same |
| WO2003000434A1 (en) * | 2001-06-21 | 2003-01-03 | Basf Corporation | Basecoat composition comprising a poly(meth)acrylate binder |
| US6794442B2 (en) | 2001-06-21 | 2004-09-21 | Basf Corporation | Fast drying basecoat refinish composition |
| WO2003027198A1 (en) * | 2001-09-27 | 2003-04-03 | Basf Corporation | Acryl clearcoat refinish composition |
| US7446149B2 (en) | 2001-09-27 | 2008-11-04 | Basf Corporation | Fast drying clearcoat refinish composition |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1432588A (en) | 1966-03-25 |
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