GB456359A - Process for the manufacture of high molecular products - Google Patents
Process for the manufacture of high molecular productsInfo
- Publication number
- GB456359A GB456359A GB13583/35A GB1358335A GB456359A GB 456359 A GB456359 A GB 456359A GB 13583/35 A GB13583/35 A GB 13583/35A GB 1358335 A GB1358335 A GB 1358335A GB 456359 A GB456359 A GB 456359A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cresol
- ether
- acid
- ethers
- methyl ether
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 8
- -1 Aromatic vinyl hydrocarbons Chemical class 0.000 abstract 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 5
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 abstract 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 abstract 4
- 229930003836 cresol Natural products 0.000 abstract 4
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 abstract 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 3
- 150000002170 ethers Chemical class 0.000 abstract 3
- DPZNOMCNRMUKPS-UHFFFAOYSA-N resorcinol dimethyl ether Natural products COC1=CC=CC(OC)=C1 DPZNOMCNRMUKPS-UHFFFAOYSA-N 0.000 abstract 3
- OSIGJGFTADMDOB-UHFFFAOYSA-N 1-Methoxy-3-methylbenzene Chemical compound COC1=CC=CC(C)=C1 OSIGJGFTADMDOB-UHFFFAOYSA-N 0.000 abstract 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 abstract 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 abstract 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 abstract 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 abstract 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 239000003921 oil Substances 0.000 abstract 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 abstract 2
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 2
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 2
- 229920002554 vinyl polymer Polymers 0.000 abstract 2
- AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical compound CCCCCOCCCCC AOPDRZXCEAKHHW-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
- DTFKRVXLBCAIOZ-UHFFFAOYSA-N 2-methylanisole Chemical compound COC1=CC=CC=C1C DTFKRVXLBCAIOZ-UHFFFAOYSA-N 0.000 abstract 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 abstract 1
- FNQIYTUXOKTMDM-UHFFFAOYSA-N 3-phenoxypropane-1,2-diol Chemical class OCC(O)COC1=CC=CC=C1 FNQIYTUXOKTMDM-UHFFFAOYSA-N 0.000 abstract 1
- QFKHNCRIMREZNN-UHFFFAOYSA-N 5-methoxy-1,5-dimethylcyclohexa-1,3-diene Chemical compound COC1(CC(=CC=C1)C)C QFKHNCRIMREZNN-UHFFFAOYSA-N 0.000 abstract 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 abstract 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 1
- 241000779819 Syncarpia glomulifera Species 0.000 abstract 1
- 229920000180 alkyd Polymers 0.000 abstract 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical group OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 abstract 1
- 239000000292 calcium oxide Substances 0.000 abstract 1
- 235000012255 calcium oxide Nutrition 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 235000011187 glycerol Nutrition 0.000 abstract 1
- 229960001867 guaiacol Drugs 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000004922 lacquer Substances 0.000 abstract 1
- 229910044991 metal oxide Inorganic materials 0.000 abstract 1
- 150000004780 naphthols Chemical class 0.000 abstract 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 abstract 1
- 229960005323 phenoxyethanol Drugs 0.000 abstract 1
- 239000001739 pinus spp. Substances 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 229920003002 synthetic resin Polymers 0.000 abstract 1
- 239000000057 synthetic resin Substances 0.000 abstract 1
- 229940036248 turpentine Drugs 0.000 abstract 1
- 239000008096 xylene 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
- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/06—Hydrocarbons
- C08F12/08—Styrene
-
- 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
- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
-
- 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
- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/34—Monomers containing two or more unsaturated aliphatic radicals
- C08F12/36—Divinylbenzene
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/36—Polymerisation in solid state
-
- 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
- C08G8/30—Chemically modified polycondensates by unsaturated compounds, e.g. terpenes
-
- 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
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/34—Monomers containing two or more unsaturated aliphatic radicals
- C08F212/36—Divinylbenzene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paints Or Removers (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Lubricants (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
Aromatic vinyl hydrocarbons are reacted with aromatic hydroxy compounds or ethers thereof in the presence of such acid-reacting substances or compounds capable of splitting off acid as are capable of accelerating the polymerization of pure styrene to yield polymeric products. Aromatic vinyl hydrocarbons specified include styrene, divinylbenzene and vinylnaphthalene, aromatic hydroxy compounds or ethers include phenol, o - cresol, m - cresol, 2-hydroxydiphenyl, 2 : 2<1>-dihydroxydiphenyl, naphthols, anisol, phenetol, cresol methyl ethers, xylene methyl ethers, resorcin dimethyl ether, glycerine phenyl ethers, hydroxyalkylphenylethers or aryloxyacetic acid ethers. Suitable polymerizing agents, which may be removed by treating the product with quicklime, barium oxide or other metallic oxide, include tin tetrachloride or borofluor acetic acid. The polymerization may be effected in an indifferent solvent such as benzine, benzene or carbon tetrachloride. The products, which may be oily to resinous bodies soluble in benzene, turpentine, and oils, or which may be soluble in caustic soda lye, may be used as softeners, intermediates in the preparation of synthetic resins, as artificial masses, and in the manufacture of lacquers containing oil, cellulose derivatives, chlorinated rubber or alkyd resins. In examples (1) styrene is polymerized with (a) m-cresol methyl ether or a crude cresol ethyl ether in the presence of borofluoroacetic acid or tin tetrachloride or (b) phenol, m-cresol, p-cresol, guaiacol, 2 : 2<1>-dihydroxydiphenyl, anisol, phenetol, m-cresol methyl ether, o-cresol methyl ether or crude cresol methyl ether, m-xylenyl methyl ether, resorcinol dimethyl ether, phenoxyethanol, b -naphthol amyl-ether, glycerine phenyl or diphenyl ether, or ethyl cresoxyacetate in the presence of borofluoroacetic acid or tin tetrachloride and of benzine or carbon tetrachloride or (21) divinylbenzene in polymerized with crude cresol, m-cresol or b -naphthol ethyl ether in the presence of borofluoroacetic acid or tin tetrachloride and of carbon tetrachloride.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3759/37A GB489973A (en) | 1937-02-08 | 1937-02-08 | Process for the manufacture of new polymeric products derived from aromatic vinyl hydrocarbons |
| DE804891X | 1937-07-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB456359A true GB456359A (en) | 1936-11-09 |
Family
ID=62527938
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB13583/35A Expired GB456359A (en) | 1937-02-08 | 1935-05-08 | Process for the manufacture of high molecular products |
| GB3759/37A Expired GB489973A (en) | 1935-04-13 | 1937-02-08 | Process for the manufacture of new polymeric products derived from aromatic vinyl hydrocarbons |
| GB20933/38A Expired GB516936A (en) | 1937-02-08 | 1938-07-14 | Process for the manufacture of new reaction products from aromatic hydrocarbons |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3759/37A Expired GB489973A (en) | 1935-04-13 | 1937-02-08 | Process for the manufacture of new polymeric products derived from aromatic vinyl hydrocarbons |
| GB20933/38A Expired GB516936A (en) | 1937-02-08 | 1938-07-14 | Process for the manufacture of new reaction products from aromatic hydrocarbons |
Country Status (3)
| Country | Link |
|---|---|
| DE (3) | DE695178C (en) |
| FR (2) | FR804891A (en) |
| GB (3) | GB456359A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE754590C (en) * | 1939-03-30 | 1953-08-03 | Bakelite Ges M B H | Process for the production of oil-soluble synthetic resins |
| US3544519A (en) * | 1967-03-30 | 1970-12-01 | Ici Ltd | Sulfonated styrene-phenol resins |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE967600C (en) * | 1939-10-30 | 1957-11-28 | Metallgesellschaft Ag | Process for the thermal treatment of polymers and copolymers of butadiene |
| US2374316A (en) * | 1940-05-15 | 1945-04-24 | Bakelite Corp | Oil soluble resins |
| DE891744C (en) * | 1940-06-26 | 1953-10-01 | Chemische Werke Huels Ges Mit | Process for the production of high molecular weight products |
| US2486831A (en) * | 1945-04-07 | 1949-11-01 | Socony Vacuum Oil Co Inc | Homopolymerization of benzyl compounds |
| US2558812A (en) * | 1947-10-24 | 1951-07-03 | Universal Oil Prod Co | Resin and process for its manufacture by condensation of a phenol, an alkyl aromatic hydrocarbon, and a polyenic hydrocarbon |
| BE489024A (en) * | 1948-05-22 | |||
| DE964441C (en) * | 1953-10-03 | 1957-05-23 | Degussa | Anti-aging agent for rubber |
| US3228899A (en) * | 1961-07-10 | 1966-01-11 | Monsanto Co | Phenolic resins from styrene, phenol and a vegetable drying oil |
-
1935
- 1935-04-13 DE DE1935I0052119 patent/DE695178C/en not_active Expired
- 1935-05-08 GB GB13583/35A patent/GB456359A/en not_active Expired
- 1935-06-30 DE DEI52683D patent/DE674984C/en not_active Expired
- 1935-07-11 DE DE1935I0052774 patent/DE696109C/en not_active Expired
-
1936
- 1936-04-10 FR FR804891D patent/FR804891A/en not_active Expired
-
1937
- 1937-02-08 GB GB3759/37A patent/GB489973A/en not_active Expired
-
1938
- 1938-07-08 FR FR49620D patent/FR49620E/en not_active Expired
- 1938-07-14 GB GB20933/38A patent/GB516936A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE754590C (en) * | 1939-03-30 | 1953-08-03 | Bakelite Ges M B H | Process for the production of oil-soluble synthetic resins |
| US3544519A (en) * | 1967-03-30 | 1970-12-01 | Ici Ltd | Sulfonated styrene-phenol resins |
Also Published As
| Publication number | Publication date |
|---|---|
| DE695178C (en) | 1940-08-19 |
| DE674984C (en) | 1939-04-26 |
| FR49620E (en) | 1939-05-16 |
| GB489973A (en) | 1938-08-08 |
| FR804891A (en) | 1936-11-04 |
| DE696109C (en) | 1940-09-11 |
| GB516936A (en) | 1940-01-16 |
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