GB744273A - Improvements in or relating to the production of modified alkyd resins - Google Patents
Improvements in or relating to the production of modified alkyd resinsInfo
- Publication number
- GB744273A GB744273A GB22148/53A GB2214853A GB744273A GB 744273 A GB744273 A GB 744273A GB 22148/53 A GB22148/53 A GB 22148/53A GB 2214853 A GB2214853 A GB 2214853A GB 744273 A GB744273 A GB 744273A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- heated together
- added
- glycerol
- linseed
- 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
- 229920000180 alkyd Polymers 0.000 title abstract 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 10
- 240000006240 Linum usitatissimum Species 0.000 abstract 3
- 235000004431 Linum usitatissimum Nutrition 0.000 abstract 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 3
- 235000004426 flaxseed Nutrition 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 abstract 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 2
- 229920002845 Poly(methacrylic acid) Polymers 0.000 abstract 2
- 241000779819 Syncarpia glomulifera Species 0.000 abstract 2
- GTTSNKDQDACYLV-UHFFFAOYSA-N Trihydroxybutane Chemical compound CCCC(O)(O)O GTTSNKDQDACYLV-UHFFFAOYSA-N 0.000 abstract 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- 239000004359 castor oil Substances 0.000 abstract 2
- 235000019438 castor oil Nutrition 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 229920001577 copolymer Polymers 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 abstract 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 2
- 239000001739 pinus spp. Substances 0.000 abstract 2
- 229920005989 resin Polymers 0.000 abstract 2
- 239000011347 resin Substances 0.000 abstract 2
- 150000005846 sugar alcohols Polymers 0.000 abstract 2
- 229940036248 turpentine Drugs 0.000 abstract 2
- 239000008096 xylene Substances 0.000 abstract 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- 244000060011 Cocos nucifera Species 0.000 abstract 1
- 235000013162 Cocos nucifera Nutrition 0.000 abstract 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 abstract 1
- 244000068988 Glycine max Species 0.000 abstract 1
- 235000010469 Glycine max Nutrition 0.000 abstract 1
- 241000350151 Guibourtia demeusei Species 0.000 abstract 1
- 235000004347 Perilla Nutrition 0.000 abstract 1
- 244000124853 Perilla frutescens Species 0.000 abstract 1
- 235000004443 Ricinus communis Nutrition 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 235000011037 adipic acid Nutrition 0.000 abstract 1
- 150000001279 adipic acids Chemical class 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000292 calcium oxide Substances 0.000 abstract 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 125000005456 glyceride group Chemical group 0.000 abstract 1
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000000944 linseed oil Substances 0.000 abstract 1
- 235000021388 linseed oil Nutrition 0.000 abstract 1
- 150000002689 maleic acids Chemical class 0.000 abstract 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 235000019198 oils Nutrition 0.000 abstract 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 abstract 1
- 239000011877 solvent mixture Substances 0.000 abstract 1
- 239000000600 sorbitol Substances 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- 235000020238 sunflower seed Nutrition 0.000 abstract 1
- 239000003784 tall oil Substances 0.000 abstract 1
- 150000003504 terephthalic acids Chemical class 0.000 abstract 1
Classifications
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/46—Polyesters chemically modified by esterification
- C08G63/48—Polyesters chemically modified by esterification by unsaturated higher fatty oils or their acids; by resin acids
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
A modified alkyd resin is made by reacting (a) a low molecular weight polymer or copolymer of an ester of acrylic acid and/or one of its alpha-substitution products with a monohydric alcohol; (b) a polycarboxylic acid or anhydride; (c) a polyhydric alcohol, and (d) a mono- or di-glyceride of an oil fatty acid. All four reactants may be heated together or two or three of them heated together, the remaining one or two added, and reaction continued. Natural or artificial resins may be added during the reaction. Specified are, for (a)-the methyl, ethyl or butyl esters of acrylic or methacrylic acid; for (b)-phthalic, terephthalic, maleic and adipic acids or anhydrides; for (c)-glycerol, pentaerythrite, trimethylol propane, hexanetriol, butanetriol, sorbitol, hexitol and glycol; for (d)-the glycerides of linseed, castor, wood-spirit, soya-bean, sunflower seed, coconut, perilla, oiticica and tall oils. The resins are soluble in xylene, turpentine substitute, esters, mono- and polyhydric alcohols, ketones and petrol, and may be emulsified. In examples: (1) a copolymer of the butyl- and ethyl-esters of methacrylic acid, glycerol and phthalic acid were heated together, linseed monoglyceride added, heating continued, and the product run into a solvent mixture of xylene and turpentine substitute; (2) an alkyd from butanetriol and phthalic anhydride was heated with linseed mono- and di-glyceride and polymethacrylic acid methyl ester; (3) castor oil, glycerol and acrylic acid ethyl ester were heated together in presence of calcium oxide, trimethylol propane and phthalic anhydride added, and heating continued; (4) polymethacrylic acid butyl ester, glycerol, phthalic anhydride and maleic anhydride were heated together, congo copal and a mixture of linseed oil and castor oil monoglyceride added, and heating continued. Specification 731,447, is referred to.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1065702X | 1951-08-28 | ||
| DE731447X | 1951-08-28 | ||
| DE744273X | 1952-11-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB744273A true GB744273A (en) | 1956-02-01 |
Family
ID=27207349
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB22148/53A Expired GB744273A (en) | 1951-08-28 | 1953-08-11 | Improvements in or relating to the production of modified alkyd resins |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1065702A (en) |
| GB (1) | GB744273A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2890186A (en) * | 1956-06-06 | 1959-06-09 | Sherwin Williams Co | Modified dialkyl fumarate alkyd resin reacted with a vinyl aromatic compound, a vinyl cyanide and an acrylate |
| US2890185A (en) * | 1956-06-06 | 1959-06-09 | Sherwin Williams Co | Modified alkyd resin reacted with a vinyl aromatic compound, a vinyl cyanide and an acrylate |
| CN112094612A (en) * | 2020-09-02 | 2020-12-18 | 德清县虎马中环佳科技有限公司 | Biomass alkyd resin adhesive and preparation method and application thereof |
-
1952
- 1952-08-27 FR FR1065702D patent/FR1065702A/en not_active Expired
-
1953
- 1953-08-11 GB GB22148/53A patent/GB744273A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2890186A (en) * | 1956-06-06 | 1959-06-09 | Sherwin Williams Co | Modified dialkyl fumarate alkyd resin reacted with a vinyl aromatic compound, a vinyl cyanide and an acrylate |
| US2890185A (en) * | 1956-06-06 | 1959-06-09 | Sherwin Williams Co | Modified alkyd resin reacted with a vinyl aromatic compound, a vinyl cyanide and an acrylate |
| CN112094612A (en) * | 2020-09-02 | 2020-12-18 | 德清县虎马中环佳科技有限公司 | Biomass alkyd resin adhesive and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1065702A (en) | 1954-05-28 |
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