GB1484278A - Chemically resistant thermosetting polymers based on acrylate esters of phenolic resins - Google Patents
Chemically resistant thermosetting polymers based on acrylate esters of phenolic resinsInfo
- Publication number
- GB1484278A GB1484278A GB3710474A GB3710474A GB1484278A GB 1484278 A GB1484278 A GB 1484278A GB 3710474 A GB3710474 A GB 3710474A GB 3710474 A GB3710474 A GB 3710474A GB 1484278 A GB1484278 A GB 1484278A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- product
- novolak
- polyol
- monocarboxylic 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
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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/14—Polymers provided for in subclass C08G
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/28—Chemically modified polycondensates
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
1484278 Polymerizable ester resins UNIROYAL Ltd 23 Aug 1974 [28 Aug 1973] 37104/74 Headings C3R and C3P [Also in Division B5] A liquid mixture comprises a polymerizable ethylenically unsaturated resinous esterification product dissolved in a copolymerizable vinyl monomer, said product being the reaction product of (A) a polyol which is a reaction product of a novolak resin and 1-1À2 moles of an alkylene oxide per phenolic hydroxyl group in the novolak, and (B) an entirely monocarboxylic acid material selected from (a) an alpha, betaethylenically unsaturated monocarboxylic acid, and (b) a mixture of (a) with up to 10% wt., based on (a), of a saturated or aromatic monocarboxylic acid having a boiling point at least as high as the boiling point of (a). Polyol (A) preferably has the formula and acid (a) the formula CH 2 =C(R)COOH where R and R<SP>1</SP> are hydrogen or alkyl, R<SP>11</SP> is hydrogen or aryl, X is C 1 -C 3 alkyl or halogen, n= 1-10 and m=0-2. The preferred vinyl monomer is styrene. The above liquid mixture may be prepared by dissolving polyol (A) and monocarboxylic acid (B) in an inert organic solvent which forms an azeotrope with water and has a boiling point of from 80-130‹ C., e.g. benzene or toluene, containing a strong acid as esterification catalyst, e.g. H 2 SO 4 or p-toluene sulphonic acid, and a phenolic inhibitor of freeradical polymerization; e.g. t-butyl catechol, hydroquinone or the monomethyl ether thereof, and then heating to reflux temperature, removing the water of esterification, and solvent therefrom and dissolving the residue in a copolymerizable vinyl monomer, then neutralizing the catalyst preferably with anhydrous potassium carbonate, at elevated temperature, and removing the resulting insoluble material, the amount of solvent used being 100-400 mol. per gram-mole of (A), and the amount of inhibitor being from 100-600 p.p.m. based on the weight of the product. In an embodiment the amount of unsaturated monocarboxylic acid (a) used is from 10-20% in stoichiometric excess of that required to react with polyol (A) and an alkylene oxide is added to neutralize the excess of acid (a) thereby converting it into a hydroxyalkylated ester which acts as a copolymerizable monomer in the resulting mixture. Suitable acids (a) are acrylic, methacrylic and ethacrylic acid. Suitable saturated or aromatic monocarboxylic acids are propionic, butyric, valeric, benzoic and toluic acids. The addition copolymer may include a reinforcing filler, e.g. glass fibre. In Examples 1-3 an unsaturated resinous product is prepared by alkylating a phenolformaldehyde novolak resin with propylene oxide in the presence of benzyltrimethylammonium hydroxide, then esterifying the resulting product with methacrylic acid in the presence of H 2 SO 4 and hydroquinone using toluene as solvent, then neutralizing with anhydrous potassium carbonate. The product is dissolved in styrene and cured either with benzoyl peroxide at elevated temperature or with cumene hydroperoxide and manganese octoate at room temperature and subsequently heat-treated. In similar Example 6 propylene oxide is used to neutralize excess methacrylic acid. Similar examples are described using p-bromo-phenol- HCHO novolak, phenolbenzaldehyde novolak or p-oresol-HCHO novolak. In Example 13 copolymers are prepared from the unsaturated polyester resin of Example 1 and any one of the following monomers: acrylonitrile, methyl methacrylate, methyl acrylate, isobutyl methacrylate, lauryl methacrylate, triallyl cyanurate and chlorostyrene. Uses.-Castings, laminates, impregnants and coatings.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA179,751A CA1015490A (en) | 1973-08-28 | 1973-08-28 | Chemically resistant thermosetting polymers based on acrylate esters of modified phenolic resins |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1484278A true GB1484278A (en) | 1977-09-01 |
Family
ID=4097673
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3710474A Expired GB1484278A (en) | 1973-08-28 | 1974-08-23 | Chemically resistant thermosetting polymers based on acrylate esters of phenolic resins |
Country Status (6)
Country | Link |
---|---|
JP (1) | JPS5335597B2 (en) |
CA (1) | CA1015490A (en) |
DE (1) | DE2440580A1 (en) |
FR (1) | FR2242418B1 (en) |
GB (1) | GB1484278A (en) |
IT (1) | IT1016894B (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2742762A1 (en) * | 1995-12-21 | 1997-06-27 | Sandoz Sa | CURABLE COMPOSITION COMPRISING A NOVOLAQUE VINYL ESTER RESIN, METHOD OF FORMING A COATING ON A SUBSTRATE, COMPRISING THE APPLICATION OF SUCH A COMPOSITION, AND SUBSTRATE COVERED BY THIS COATING |
US6893784B2 (en) * | 2000-09-20 | 2005-05-17 | Taiyo Ink Manufacturing Co., Ltd. | Carboxyl group-containing photosensitive resin, alkali-developable, photocurable and thermosetting composition containing the same, and cured products thereof |
EP1858975A2 (en) * | 2005-02-25 | 2007-11-28 | Schenectady International, Inc. | Modified novolak resin for use as tackifier |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2935719A1 (en) * | 1979-09-04 | 1981-03-12 | Bayer Ag, 5090 Leverkusen | MORTAR FROM INORGANIC BINDING AGENTS, METHOD FOR THEIR PRODUCTION AND THEIR USE. |
JPS5755910A (en) * | 1980-09-19 | 1982-04-03 | Osaka Soda Co Ltd | Acrylate resin composition |
JPS58159080U (en) * | 1982-04-16 | 1983-10-24 | 日本自動販売株式会社 | beverage vending machine |
JPS58159082U (en) * | 1982-04-16 | 1983-10-24 | 日本自動販売株式会社 | beverage vending machine |
JP4167599B2 (en) * | 2002-02-19 | 2008-10-15 | 太陽インキ製造株式会社 | Curable resin and curable resin composition containing the same |
NL2005685C2 (en) * | 2010-11-12 | 2012-05-15 | Visker Beheer B V | COATING SYSTEM, APPLICATION THEREOF, AND METHOD FOR MANUFACTURING THEM. |
-
1973
- 1973-08-28 CA CA179,751A patent/CA1015490A/en not_active Expired
-
1974
- 1974-08-23 DE DE19742440580 patent/DE2440580A1/en active Pending
- 1974-08-23 GB GB3710474A patent/GB1484278A/en not_active Expired
- 1974-08-27 FR FR7429285A patent/FR2242418B1/fr not_active Expired
- 1974-08-27 IT IT6962274A patent/IT1016894B/en active
- 1974-08-28 JP JP9880774A patent/JPS5335597B2/ja not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2742762A1 (en) * | 1995-12-21 | 1997-06-27 | Sandoz Sa | CURABLE COMPOSITION COMPRISING A NOVOLAQUE VINYL ESTER RESIN, METHOD OF FORMING A COATING ON A SUBSTRATE, COMPRISING THE APPLICATION OF SUCH A COMPOSITION, AND SUBSTRATE COVERED BY THIS COATING |
US6893784B2 (en) * | 2000-09-20 | 2005-05-17 | Taiyo Ink Manufacturing Co., Ltd. | Carboxyl group-containing photosensitive resin, alkali-developable, photocurable and thermosetting composition containing the same, and cured products thereof |
EP1858975A2 (en) * | 2005-02-25 | 2007-11-28 | Schenectady International, Inc. | Modified novolak resin for use as tackifier |
EP1858975A4 (en) * | 2005-02-25 | 2009-01-07 | Schenectady Int Inc | Modified novolak resin for use as tackifier |
US7772345B2 (en) | 2005-02-25 | 2010-08-10 | Si Group, Inc. | Modified novolak resin for use as tackifier |
Also Published As
Publication number | Publication date |
---|---|
FR2242418B1 (en) | 1978-02-17 |
DE2440580A1 (en) | 1975-03-06 |
JPS5335597B2 (en) | 1978-09-28 |
FR2242418A1 (en) | 1975-03-28 |
IT1016894B (en) | 1977-06-20 |
JPS5088198A (en) | 1975-07-15 |
CA1015490A (en) | 1977-08-09 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PCNP | Patent ceased through non-payment of renewal fee |