GB1111704A - Process for preparing phenol novolac resins - Google Patents
Process for preparing phenol novolac resinsInfo
- Publication number
- GB1111704A GB1111704A GB2940067A GB2940067A GB1111704A GB 1111704 A GB1111704 A GB 1111704A GB 2940067 A GB2940067 A GB 2940067A GB 2940067 A GB2940067 A GB 2940067A GB 1111704 A GB1111704 A GB 1111704A
- Authority
- GB
- United Kingdom
- Prior art keywords
- solvent
- water
- added
- formaldehyde
- phenol
- 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title abstract 3
- 229920003986 novolac Polymers 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 10
- 239000002904 solvent Substances 0.000 abstract 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 abstract 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000012744 reinforcing agent Substances 0.000 abstract 2
- 241001323490 Colias gigantea Species 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 1
- 235000021355 Stearic acid Nutrition 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 229920001971 elastomer Polymers 0.000 abstract 1
- 239000000806 elastomer Substances 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000004312 hexamethylene tetramine Substances 0.000 abstract 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 abstract 1
- 229960004011 methenamine Drugs 0.000 abstract 1
- 229920003052 natural elastomer Polymers 0.000 abstract 1
- 229920001194 natural rubber Polymers 0.000 abstract 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 235000006408 oxalic acid Nutrition 0.000 abstract 1
- 229920002866 paraformaldehyde Polymers 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000011369 resultant mixture Substances 0.000 abstract 1
- 239000008117 stearic acid Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 229920003051 synthetic elastomer Polymers 0.000 abstract 1
- 239000005061 synthetic rubber Substances 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
-
- 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
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
-
- 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
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
- C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L11/00—Compositions of homopolymers or copolymers of chloroprene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/16—Ethene-propene or ethene-propene-diene copolymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
- C08L23/20—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having four to nine carbon atoms
- C08L23/22—Copolymers of isobutene; Butyl rubber; Homopolymers or copolymers of other iso-olefins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L7/00—Compositions of natural rubber
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
- C08L9/02—Copolymers with acrylonitrile
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)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Novolaks are prepared by condensing biphenol-A with formaldehyde or a chemical equivalent thereof in the presence of an inert organic solvent, a minor amount of water and 0.1-0.6% of a weak acid. The formaldehyde may be a mixture of paraformaldehyde and formalin. Less than 1 mol. may be used per mol. of phenol. The solvent may be an aromatic hydrocarbon, e.g. toluene, xylene, or another solvent boiling between 100 DEG and 160 DEG C. 33-300% may be used. The weak acid may be oxalic acid and the reaction may take place under pressure. In a particular embodiment about half of the phenol, some of the HCHO, all the solvent and all the water may be heated to 80-90 DEG C. The remaining reactants may then be added whilst heating is continued, the resultant mixture being refluxed until no more than 1% of free HCHO is present, stripped of water and solvent and heated to 140 DEG C. under vacuum. 1-150% of the product may be added to an elastomer as a reinforcing agent. It may be ground up, mixed with 5-10% hexamethylene tetramine and added to an elastomeric composition which may contain a natural or synthetic rubber, e.g. a butadiene/acrylonitrile copolymer, other fillers and reinforcing agents, e.g. ZnO, vulcanizing agents, e.g. sulphur and 2-mercaptobenzthiazole and stearic acid.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC0035728 | 1965-04-29 | ||
| DEC0036494 | 1965-07-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1111704A true GB1111704A (en) | 1968-05-01 |
Family
ID=25970054
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2940067A Expired GB1111704A (en) | 1965-04-29 | 1966-04-27 | Process for preparing phenol novolac resins |
| GB1849266A Expired GB1111703A (en) | 1965-04-29 | 1966-04-27 | Improvements in or relating to elastomers |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1849266A Expired GB1111703A (en) | 1965-04-29 | 1966-04-27 | Improvements in or relating to elastomers |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE679702A (en) |
| DE (1) | DE1544711A1 (en) |
| GB (2) | GB1111704A (en) |
| NL (2) | NL6605704A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3211917A1 (en) * | 1982-03-31 | 1983-10-13 | Hoechst Ag, 6230 Frankfurt | RUBBER VOLCANISES WITH A RELATIVELY LOW HARDNESS AND METHOD FOR REDUCING THE DURAMIC DEFORMED CONVERSION OF THE VOLCANISATE'S ENERGY CONTRACT |
-
0
- NL NL134119D patent/NL134119C/xx active
-
1965
- 1965-07-24 DE DE19651544711 patent/DE1544711A1/en active Pending
-
1966
- 1966-04-19 BE BE679702D patent/BE679702A/xx unknown
- 1966-04-27 GB GB2940067A patent/GB1111704A/en not_active Expired
- 1966-04-27 GB GB1849266A patent/GB1111703A/en not_active Expired
- 1966-04-28 NL NL6605704A patent/NL6605704A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1111703A (en) | 1968-05-01 |
| DE1570351A1 (en) | 1970-02-19 |
| DE1544711A1 (en) | 1969-08-07 |
| NL134119C (en) | |
| BE679702A (en) | 1966-10-19 |
| NL6605704A (en) | 1966-10-31 |
| DE1570351B2 (en) | 1972-07-06 |
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