GB666873A - Manufacture of artificial resins from aldehydes and aromatic hydrocarbons - Google Patents
Manufacture of artificial resins from aldehydes and aromatic hydrocarbonsInfo
- Publication number
- GB666873A GB666873A GB26190/48A GB2619048A GB666873A GB 666873 A GB666873 A GB 666873A GB 26190/48 A GB26190/48 A GB 26190/48A GB 2619048 A GB2619048 A GB 2619048A GB 666873 A GB666873 A GB 666873A
- Authority
- GB
- United Kingdom
- Prior art keywords
- toluene
- acid
- acidity
- resin
- sulphonic 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
- 239000011347 resin Substances 0.000 title abstract 6
- 229920005989 resin Polymers 0.000 title abstract 6
- 150000001299 aldehydes Chemical class 0.000 title abstract 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 7
- 239000003054 catalyst Substances 0.000 abstract 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 abstract 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 abstract 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 230000006641 stabilisation Effects 0.000 abstract 2
- 238000011105 stabilization Methods 0.000 abstract 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical class C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 abstract 1
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 abstract 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- -1 alkaline earth metal carbonates Chemical class 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000001099 ammonium carbonate Substances 0.000 abstract 1
- 235000012501 ammonium carbonate Nutrition 0.000 abstract 1
- 235000010216 calcium carbonate Nutrition 0.000 abstract 1
- 229910000019 calcium carbonate Inorganic materials 0.000 abstract 1
- 239000000292 calcium oxide Substances 0.000 abstract 1
- 235000012255 calcium oxide Nutrition 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical group 0.000 abstract 1
- 150000004679 hydroxides Chemical class 0.000 abstract 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 235000017550 sodium carbonate Nutrition 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G10/00—Condensation polymers of aldehydes or ketones with aromatic hydrocarbons or halogenated aromatic hydrocarbons only
- C08G10/02—Condensation polymers of aldehydes or ketones with aromatic hydrocarbons or halogenated aromatic hydrocarbons only of aldehydes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/38—Boron-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/18—Condensation polymers of aldehydes or ketones with aromatic hydrocarbons or their halogen derivatives only
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The melting point of a resin obtained by condensation of an unsubstituted or hydrocarbon substituted aromatic hydrocarbon with an aldehyde is increased by heating with an acid-reacting hardening catalyst at a temperature above 140 DEG C., e.g. from 140 DEG to 200 DEG C., with subsequent stabilization of the resin by elimination of acidity. Resins specified are the condensation products of formaldehyde and naphthalene, xylene, naphtha fractions and methyl naphthalenes. Catalysts specified are sulphuric acid, phosphoric acid, ferric chloride, aluminium chloride, p-toluene sulphonic acid and p-toluene sulphochloride. Solvents such as toluene may be used. The acidity may be removed by neutralization, e.g. with alkali and alkaline earth metal carbonates, hydroxides and oxides, such as Na2CO3, CaCO3 and CaO, gaseous ammonia, ammonium carbonate, and organic bases, e.g. pyridine and quinoline and their derivatives. In the case of volatile catalysts, e.g. p-toluene sulphonic acid, the acidity may be removed by passing steam into the molten hardened resin. In example (1) a toluene solution of a naphthalene-formaldehyde resin is heated until free from water, p-toluene sulphonic acid is then added and the mixture heated, steam being finally admitted to remove the volatile catalyst. Further examples are given (2-5) showing how the acid concentration and/or time affects the degree of hardening and (6-8) showing comparatively how stabilization proceeds. Specification 633,923 is referred to.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB26190/48A GB666873A (en) | 1948-10-07 | 1948-10-07 | Manufacture of artificial resins from aldehydes and aromatic hydrocarbons |
| GB14628/52A GB735876A (en) | 1948-10-07 | 1952-06-10 | Manufacture of artificial resins from aldehydes and aromatic hydrocarbons |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB26190/48A GB666873A (en) | 1948-10-07 | 1948-10-07 | Manufacture of artificial resins from aldehydes and aromatic hydrocarbons |
| GB14628/52A GB735876A (en) | 1948-10-07 | 1952-06-10 | Manufacture of artificial resins from aldehydes and aromatic hydrocarbons |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB666873A true GB666873A (en) | 1952-02-20 |
Family
ID=62529117
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB26190/48A Expired GB666873A (en) | 1948-10-07 | 1948-10-07 | Manufacture of artificial resins from aldehydes and aromatic hydrocarbons |
| GB14628/52A Expired GB735876A (en) | 1948-10-07 | 1952-06-10 | Manufacture of artificial resins from aldehydes and aromatic hydrocarbons |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB14628/52A Expired GB735876A (en) | 1948-10-07 | 1952-06-10 | Manufacture of artificial resins from aldehydes and aromatic hydrocarbons |
Country Status (1)
| Country | Link |
|---|---|
| GB (2) | GB666873A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2958676A (en) * | 1957-11-26 | 1960-11-01 | Basf Ag | Naphthalene-formaldehyde condensation products |
| DE1184957B (en) * | 1961-08-08 | 1965-01-07 | Exxon Research Engineering Co | Process for the preparation of higher molecular weight condensation products by reacting alkyl-substituted benzenes with formaldehyde |
| US3178393A (en) * | 1960-08-10 | 1965-04-13 | Velsicol Chemical Corp | Formaldehyde-aromatic hydrocarbon condensation product prepared with a hydrocarbon sulfonic acid |
| EP2810969A4 (en) * | 2012-01-31 | 2015-09-02 | Mitsubishi Gas Chemical Co | Naphthalene-formaldehyde resin, naphthalene-formaldehyde resin with bonds formed by deacetalization, and modified naphthalene-formaldehyde resin |
| EP2821421A4 (en) * | 2012-02-27 | 2015-09-30 | Mitsubishi Gas Chemical Co | Acidified mono alkyl naphthalene formaldehyde resin |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1545157A1 (en) * | 1964-01-31 | 1970-01-22 | Glanzstoff Ag | Process to improve the stability of polyolefins |
-
1948
- 1948-10-07 GB GB26190/48A patent/GB666873A/en not_active Expired
-
1952
- 1952-06-10 GB GB14628/52A patent/GB735876A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2958676A (en) * | 1957-11-26 | 1960-11-01 | Basf Ag | Naphthalene-formaldehyde condensation products |
| US3178393A (en) * | 1960-08-10 | 1965-04-13 | Velsicol Chemical Corp | Formaldehyde-aromatic hydrocarbon condensation product prepared with a hydrocarbon sulfonic acid |
| DE1184957B (en) * | 1961-08-08 | 1965-01-07 | Exxon Research Engineering Co | Process for the preparation of higher molecular weight condensation products by reacting alkyl-substituted benzenes with formaldehyde |
| EP2810969A4 (en) * | 2012-01-31 | 2015-09-02 | Mitsubishi Gas Chemical Co | Naphthalene-formaldehyde resin, naphthalene-formaldehyde resin with bonds formed by deacetalization, and modified naphthalene-formaldehyde resin |
| US9200105B2 (en) | 2012-01-31 | 2015-12-01 | Mitsubishi Gas Chemical Company, Inc. | Naphthalene formaldehyde resin, deacetalized naphthalene formaldehyde resin, and modified naphthalene formaldehyde resin |
| EP2821421A4 (en) * | 2012-02-27 | 2015-09-30 | Mitsubishi Gas Chemical Co | Acidified mono alkyl naphthalene formaldehyde resin |
Also Published As
| Publication number | Publication date |
|---|---|
| GB735876A (en) | 1955-08-31 |
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