US1946430A - Process for - Google Patents
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- US1946430A US1946430A US1946430DA US1946430A US 1946430 A US1946430 A US 1946430A US 1946430D A US1946430D A US 1946430DA US 1946430 A US1946430 A US 1946430A
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
- 239000007859 condensation product Substances 0.000 description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- -1 aromatic hydroxy compound Chemical class 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
- 239000000835 fiber Substances 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- 239000011592 zinc chloride Substances 0.000 description 8
- 235000005074 zinc chloride Nutrition 0.000 description 8
- 210000002268 Wool Anatomy 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- NJQRKFOZZUIMGW-UHFFFAOYSA-N 1,3,5-trichloro-2-(chloromethyl)benzene Chemical compound ClCC1=C(Cl)C=C(Cl)C=C1Cl NJQRKFOZZUIMGW-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 230000003472 neutralizing Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- MFHPYLFZSCSNST-UHFFFAOYSA-N 1-chloro-2-(trichloromethyl)benzene Chemical class ClC1=CC=CC=C1C(Cl)(Cl)Cl MFHPYLFZSCSNST-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FYAUQRPGUUXFLL-UHFFFAOYSA-N [bromo(chloro)methyl]benzene Chemical class ClC(Br)C1=CC=CC=C1 FYAUQRPGUUXFLL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000005524 benzylchlorides Chemical class 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
Definitions
- the present invention relates to a new process for preparing Water-soluble condensation products from phenolic compounds and halogenated aralkyl compounds containing no hydroxy group.
- new condensation products are obtainable by starting from an aromatic hydroxy compound, as for instance phenol, ocand c-naphthol and substitution products thereof, containing no sulfonic acid group and heating the hydroxy compound advantageously in the presence of a catalyst, as for instance, zinc chloride, aluminium chloride, with about the equimolecular quantity of a halogenated aralkyl compound, as for instance 0-, m-, p-,
- the condensation product can be isolated according to known ,methods or it can be sulfonated at a temperature between about 35-80 C. without isolation in the same apparatus by means of oleum, sulfuric acid, chlorosulfonic acid and the like.
- the sulfuric acid or the alkali metal salts of the condensation product are obtained in the known manner for example by neutralizing with caustic alkali lye and evaporating.
- the products thus obtainable are in form of their alkali metal salts weakly colored powders easily soluble in water. They possess in the free form as well as in the form of their alkali metal salts the valuable technical property of preventing animal fibers, such as wool and silk, (to which fibers they may be applied, for instance, in form of their aqueous solution) from absorbing dyestuffs which are dyed in an acid or neutrally reacting bath.
- Our new products are, therefore, auxiliary substances in dyeing and printing. When applying these new products, for instance, to mixed textile fabrics made of cotton and silk or cotton and wool etc., which are to be printed or dyed, the animal fibers, i. e.
- the product is stirred with ice and water, avoiding any strong heating, neutralized with caustic soda lye and evaporated to dryness.
- the mass can be ground to a colorless powder, which dissolves readily in water to a clear solution and in general, displays a similar behaviour as the product described in the example of application Ser. No. 313,635, filed October 19, 1928 now Patent 1,860,487.
- Process for preparing water-soluble condensation products comprising heating and aromatic hydroxy compound with about the same quantity or" a halogenated aralkylhalogenide containing no hydroxyl group to a temperature of from 15 to 100 C. for 3-15 hours in the presence of a catalyst selected from the group consisting of Zinc chloride and aluminium chloride and sulfonating the condensation product obtained at a temperature between 35 and C.
- Process for preparing water-soluble condensation products comprising heating phenol with about the same quantity of trichlorobenzylchloride to a temperature of from 15 to 100 C. for from 3 to 15 hours in the presence of a cataand sulfonating the reaction product at a tem-- perature of between 35 and C. with 28 parts of oleum of 20% strength for from 1 to 2 hours, pouring the mixture into ice and water, neutralizing with a sodium hydroxide solution and evaporating.
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
T aryl) burrs STATES PATENT OFFICE PROCESS FOR PREPARING WATER- SOLUBLE CONDENSA'I'ION PRODUCTS Alfred Thauss, Cologne-Deutz, Gustav Mauthe,
Cologne-Holweide, and Arnold Doser, Cologne- Mnlheim, Germany,
assignors, by mesne assignments, to General Aniline Works, 1110., New
York, N. Y.
No Drawing. Application March 11, 1930, Serial No. 435,019, and in Germany March 23, 1929 4 Claims.
The present invention relates to a new process for preparing Water-soluble condensation products from phenolic compounds and halogenated aralkyl compounds containing no hydroxy group.
According to the present invention new condensation products are obtainable by starting from an aromatic hydroxy compound, as for instance phenol, ocand c-naphthol and substitution products thereof, containing no sulfonic acid group and heating the hydroxy compound advantageously in the presence of a catalyst, as for instance, zinc chloride, aluminium chloride, with about the equimolecular quantity of a halogenated aralkyl compound, as for instance 0-, m-, p-,
chloroand bromo-benzylchlorides, diand trichlorobenzylchlorides, xylylchlorides, naphthylchlorides, to a temperature between about 15-l00 C. for about 3-15 hours. The condensation product can be isolated according to known ,methods or it can be sulfonated at a temperature between about 35-80 C. without isolation in the same apparatus by means of oleum, sulfuric acid, chlorosulfonic acid and the like. The sulfuric acid or the alkali metal salts of the condensation product are obtained in the known manner for example by neutralizing with caustic alkali lye and evaporating.
The reaction takes place according to the following equation:
alk=alkylene; Hal=halogen; R: The products thus obtainable are in form of their alkali metal salts weakly colored powders easily soluble in water. They possess in the free form as well as in the form of their alkali metal salts the valuable technical property of preventing animal fibers, such as wool and silk, (to which fibers they may be applied, for instance, in form of their aqueous solution) from absorbing dyestuffs which are dyed in an acid or neutrally reacting bath. Our new products are, therefore, auxiliary substances in dyeing and printing. When applying these new products, for instance, to mixed textile fabrics made of cotton and silk or cotton and wool etc., which are to be printed or dyed, the animal fibers, i. e. the silk or the wool, in the mixed fabrics are prevented. from taking up the dyestufis. In this manner multi-colored efiects are easily obtainable. Our new resists may be applied to the fibers either before or during the dyeing proc- .esses.
The following example will illustrate our invention without limiting it thereto:
Erample:19 parts by weight of phenol, 46 parts by weight of trichlorobenzylchloride obtainable by chlorinating toluene and 0.2 part by weight of Zinc chloride are heated slowly with stirring to 85 C. and when the at first vigorous evolution of hydrogen chloride has subsided the whole is further heated to about 10-l5 C. higher. This temperature is maintained for about 6-8 hours until a test portion becomes viscous on cooling. The temperature is then reduced to 40-45" C. and 28 parts by weight of 20% oleum are dropped in so slowly that the temperature does not exceed C. The internal temperature is then maintained at 65-'70 C. for l-2 hours until a test portion dissolves in water to a clear and colorless solution and remains unchanged on heating.
The working up is carried out in a very simple manner:-
The product is stirred with ice and water, avoiding any strong heating, neutralized with caustic soda lye and evaporated to dryness. The mass can be ground to a colorless powder, which dissolves readily in water to a clear solution and in general, displays a similar behaviour as the product described in the example of application Ser. No. 313,635, filed October 19, 1928 now Patent 1,860,487.
We claim:
1. Process for preparing water-soluble condensation products comprising heating and aromatic hydroxy compound with about the same quantity or" a halogenated aralkylhalogenide containing no hydroxyl group to a temperature of from 15 to 100 C. for 3-15 hours in the presence of a catalyst selected from the group consisting of Zinc chloride and aluminium chloride and sulfonating the condensation product obtained at a temperature between 35 and C.
2. Process for preparing water-soluble condensation products comprising heating phenol with about the same quantity of halogenated benzylchloride to a temperature of from 15 to C. for from 3 to 15 hours in the presence of a catalyst selected from the group consisting of zinc chloride and aluminium chloride and sulfonating the condensation product obtained at a temperature between 35 and 80 C.
3. Process for preparing water-soluble condensation products comprising heating phenol with about the same quantity of trichlorobenzylchloride to a temperature of from 15 to 100 C. for from 3 to 15 hours in the presence of a cataand sulfonating the reaction product at a tem-- perature of between 35 and C. with 28 parts of oleum of 20% strength for from 1 to 2 hours, pouring the mixture into ice and water, neutralizing with a sodium hydroxide solution and evaporating.
ALFRED THAUSS.
GUSTAV MAUTHE.
ARNOLD DOSER.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1946430A true US1946430A (en) | 1934-02-06 |
Family
ID=3426106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US1946430D Expired - Lifetime US1946430A (en) | Process for |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1946430A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2528769A (en) * | 1947-05-28 | 1950-11-07 | Socony Vacuum Oil Co Inc | Reaction product of haloalkylthiophenes and hydroxyaryl compounds |
-
0
- US US1946430D patent/US1946430A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2528769A (en) * | 1947-05-28 | 1950-11-07 | Socony Vacuum Oil Co Inc | Reaction product of haloalkylthiophenes and hydroxyaryl compounds |
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