Anionic compounds based on modified novolak oxyalkylates, their _preparation, and their use as foam-free surface-active agents

• US 4,403,077 A
• Filed: 05/21/1982
• Issued: 09/06/1983
• Est. Priority Date: 05/23/1981
• Status: Expired due to Term

• Current Assignee: Clariant GmbH (Clariant AG)
• Original Assignee: Hoechst Aktiengesellschaft (Sanofi )
• Inventors: Weide, Joachim, Deubel, Reinhold, Uhrig, Heinz
• Primary Examiner(s): Phynes, Lucille M.
• Application Number:
  US06/380,995
• Time in Patent Office: 473 Days
• Field of Search: 525/502, 525/505, 525/507, 528/129
• US Class Current: 525/502
• CPC Class Codes: C08G 8/28 Chemically modified polycondensates
• CPC Class Codes: C08G 8/36 by etherifying
• CPC Class Codes: C09B 67/0086 anionic dispersing agents
• CPC Class Codes: C09K 23/00 Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
• CPC Class Codes: C09K 23/02 Alkyl sulfonates or sulfuric acid ester salts derived from monohydric alcohols
• CPC Class Codes: C09K 23/42 Ethers, e.g. polyglycol ethers of alcohols or phenols
• CPC Class Codes: D06P 1/613 Polyethers without nitrogen
• CPC Class Codes: Y10S 516/03 Organic sulfoxy compound containing

Abstract

The invention relates to novolak oxyalkylate mixed esters which, on the one hand, contain benzoyl and/or naphthoyl radicals and, on the other hand, contain maleic acid and/or sulfosuccinic acid half-ester groups. They are obtained by reacting novolak oxyalkylates with benzoic acid and/or naphthoic acid or with its anhydride or chloride on the one hand and maleic anhydride on the other hand and, if appropriate, reacting the maleic acid half-ester groups with sulfites to give sulfosuccinic acid half-ester groups. These compounds are highly suitable for use as dispersing agents for the preparation of low-foam dispersions of pigments, dyestuffs and other agents and as emulsifying, leveling and dyeing auxiliaries.

Claims

1. Compound of the formula I ##STR4## in which Ar denotes benzene or naphthalene, X denotes --CH₂ --CH₂ -- and/or --CH₂ --CH(CH₃)--, 0 to (m-1) of the radicals A denote hydrogen, 1 to m of the radicals A denote benzoyl and/or naphthoyl, 1 to m of the radicals A are --CO--CH═

CH--COOM and/or --CO--CH₂ --CH(SO₃ M)--COOM, in which M represents a cation, R¹, R² and R³ denote hydrogen or alkyl having 1 to 14 C atoms, R denotes hydrogen and/or alkyl having 1 to 9 C atoms, n denotes a number from 1 to 150 and m denotes a number from 2 to 12.

2. A compound as claimed in claim 1, in which R¹ denotes hydrogen, R² and R³ denote hydrogen or alkyl having 1 to 12 C atoms, R denotes hydrogen and/or alkyl having 1 to 4 C atoms, n denotes a number from 2 to 20, m denotes a number from 4 to 10 and M denotes hydrogen, an alkali metal, one equivalent of an alkaline earth metal and/or an ammonium group which can be substituted by lower alkyl and/or lower hydroxyalkyl or M denotes an ammonium group obtained from ammonia or lower alkylamines by addition of up to 150 ethylene oxide and/or propylene oxide units.

3. A compound as claimed in claim 1, in which R denotes hydrogen and M denotes hydrogen, sodium and/or an ammonium group which can be substituted by lower alkyl and/or hydroxyalkyl or M denotes an ammonium group obtained from ammonia or lower alkylamine by addition of 5 to 30 ethylene oxide and/or propylene oxide units.

4. A compound as claimed in claim 3, in which Ar denotes benzene, R² and R³ denote hydrogen or alkyl having 1 to 9 C atoms, n denotes a number from 8 to 20 and m denotes a number from 4 to 8.

5. A compound as claimed in claim 3, in which Ar denotes naphthalene, R² and R³ denote hydrogen or alkyl having 1 to 9 C atoms, n denotes a number from 8 to 20 and m denotes a number from 4 to 8.

6. A process for preparing a compound as claimed in claims 1 or 5, which process comprises treating a compound of the formula I in which A is hydrogen with 1 to m moles of an O-acylating compound which introduces the benzoyl and/or naphthoyl radical and with 1 to m moles of maleic anhydride and, if appropriate, 1 to m moles of sulfite or hydrogen sulfite or 0.5 to 0.5 m moles of disulfite and neutralizing any free acid group present with a base which introduces the radical M.

7. The process as claimed in claim 6, wherein a compound of the formula I in which A is hydrogen is reacted with benzoic acid, naphthoic acid or the corresponding acid chlorides or anhydrides in the presence of acid catalysts.

8. The process as claimed in claim 6, wherein a compound of the formula I in which A is hydrogen is reacted with lower alkyl esters of benzoic acid or naphthoic acid in the presence of basic catalysts.

9. The process as claimed in claims 6 or 8, wherein as sulfite or hydrogen sulfite or disulfite the respective sodium salt is used.

10. The method of using a compound as claimed in claim 1, as a surface-active agent.

11. The method of using a compound as claimed in claim 1, as a coupling auxiliary.

12. The method of using a compound as claimed in claim 1, as a dispersing and distributing agent.

13. The method of using a compound as claimed in claim 1, as a wetting, emulsifying, leveling and dyeing auxiliary.