GB947910A - Surface active ethers of n-(hydroxymethyl)-lactams - Google Patents

Surface active ethers of n-(hydroxymethyl)-lactams

Info

Publication number
GB947910A
GB947910A GB3720461A GB3720461A GB947910A GB 947910 A GB947910 A GB 947910A GB 3720461 A GB3720461 A GB 3720461A GB 3720461 A GB3720461 A GB 3720461A GB 947910 A GB947910 A GB 947910A
Authority
GB
United Kingdom
Prior art keywords
hydroxymethyl
methyl
hydrogen
ethers
polypropoxylated
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
Application number
GB3720461A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
GAF Chemicals Corp
Original Assignee
General Aniline and Film Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from US67434A external-priority patent/US3136766A/en
Priority claimed from US100583A external-priority patent/US3161051A/en
Application filed by General Aniline and Film Corp filed Critical General Aniline and Film Corp
Publication of GB947910A publication Critical patent/GB947910A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D211/74—Oxygen atoms
    • C07D211/76—Oxygen atoms attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • C07D265/32—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings with oxygen atoms directly attached to ring carbon atoms
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01F—MEASURING VOLUME, VOLUME FLOW, MASS FLOW OR LIQUID LEVEL; METERING BY VOLUME
    • G01F23/00—Indicating or measuring liquid level or level of fluent solid material, e.g. indicating in terms of volume or indicating by means of an alarm
    • G01F23/14—Indicating or measuring liquid level or level of fluent solid material, e.g. indicating in terms of volume or indicating by means of an alarm by measurement of pressure
    • G01F23/16—Indicating, recording, or alarm devices being actuated by mechanical or fluid means, e.g. using gas, mercury, or a diaphragm as transmitting element, or by a column of liquid

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Fluid Mechanics (AREA)
  • General Physics & Mathematics (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Measuring Fluid Pressure (AREA)

Abstract

The invention comprises non-foaming alkalistable surface active ethers of N-(hydroxymethyl)-lactams of the general formula: <FORM:0947910/C2/1> wherein R is an alkyl group of 8 to 18 carbon atoms or a phenyl or naphthyl group substituted by 1 or 2 alkyl groups of from 8 to 18 carbon atoms; R1 is hydrogen or methyl and wherein the ethoxy and propoxy units are arranged in any order when both are present in the -OCH2CHR1 chain; R2; R3 and R4 are hydrogen, methyl or ethyl radicals; z is a single bond, -CH2-, -CH2-CH2- or -o- and m is an integer of from 2 to 100. The ethers may be prepared by reacting polyethoxylated or polypropoxylated phenols or aliphatic alcohols or mixed polyglycol monoether of phenol or aliphatic alcohols with an N-(hydroxymethyl)-lactam at a temperature of 80 DEG C. for 4 to 12 hours in the presence of p-toluene sulphonic acid monohydrate and neutralising the reaction mass with an organic amine. The phenol or aliphatic alcohol may be polyethoxylated or polypropoxylated in situ and the N-(hydroxymethyl) lactam may be prepared by reacting alkyl substituted or unsubstituted 2-pyrrolidone, a -piperidone, caprolactam or morpholone with p-formaldehyde in the presence of potassium hydroxide. Several examples are given. U.S.A. Specifications 1,970,578, 2,213,477, 2,575,832, 2,593,112 and 2,676,975 are referred to.ALSO:The invention comprises non-foaming alkali stable surface active ethers of N-(hydroxymethyl)-lactams of the general formula: <FORM:0947910/C3/1> wherein R is a C8 to C18 alkyl group or a phenyl or naphthyl group substituted by 1 or 2 C8 to C18 alkyl groups, R1 is hydrogen or methyl, and wherein the ethoxy and propoxy units are arranged in any order when both are present in the -OCH2CHR1 chain, R2, R3 and R4 are hydrogen, methyl or ethyl radicals, Z is a single bond, -CH2-, -CH2-CH2- or -O- and m is an integer of from 2 to 100. The ethers may be prepared by reacting polyethoxylated or polypropoxylated phenols or aliphatic alcohols or mixed polyglycol monoether of phenol or aliphatic alcohols with an N-(hydroxymethyl)-lactam at a temperature of 80 DEG C. for 4 to 12 hours in the presence of p-toluene sulphonic acid monohydrate and neutralising the reaction mass with an organic amine. The phenol or aliphatic alcohol may be polyethoxylated or polypropoxylated in situ. Several examples are given. U.S.A. Specifications 1,970,578, 2,213,477, 2,575,832, 2,593,112 and 2,676,975 are referred to.ALSO:Surface-active ethers of N-(hydroxymethyl)-lactams of the general formula <FORM:0947910/C3/1> wherein R is a C8 to C18 alkyl group on a phenyl or naphthyl group substituted by 1 or 2 C8 to C18 alkyl groups, R1 is hydrogen or methyl and wherein the ethenoxy and propenoxy units are arranged in any order when both are present in the -OCH2CHR1- chain, R2, R3 and R4 are hydrogen, methyl or ethyl radicals, 2 is a single band, -CH2-, -CH2-CH2-, or -O- and m is an integer of from 2 to 100, may be mixed with alkali metal hydroxides or silicates to yield non-discoloring and non-foaming surface active compositions. Such compositions are suitable for cleaning metals prior to plating, fabricating and processing, and for washing glass, dishes and bottles. U.S.A. Specifications 1,970,578, 2,213,477, 2,575,832, 2,593,112 and 2,676,975 are referred to.
GB3720461A 1960-11-04 1961-10-17 Surface active ethers of n-(hydroxymethyl)-lactams Expired GB947910A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US67434A US3136766A (en) 1960-11-04 1960-11-04 Surface active ethers of nu-(hydroxymethyl)-lactams
US100583A US3161051A (en) 1961-04-04 1961-04-04 Level indicating device and system

Publications (1)

Publication Number Publication Date
GB947910A true GB947910A (en) 1964-01-29

Family

ID=31949672

Family Applications (2)

Application Number Title Priority Date Filing Date
GB3720461A Expired GB947910A (en) 1960-11-04 1961-10-17 Surface active ethers of n-(hydroxymethyl)-lactams
GB1225662D Expired GB947010A (en) 1960-11-04 1962-03-30 Liquid level indicating device

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB1225662D Expired GB947010A (en) 1960-11-04 1962-03-30 Liquid level indicating device

Country Status (3)

Country Link
DE (1) DE1201058B (en)
GB (2) GB947910A (en)
SE (1) SE306533B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0241050A2 (en) * 1986-04-08 1987-10-14 Hisamitsu Pharmaceutical Co., Inc. Azacycloalkane derivatives, absorption promoters containing the derivatives as the effective ingredient and external preparation containing the absorption promoters

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4454760A (en) * 1981-07-29 1984-06-19 King Engineering Corporation Pressure sensing system
US4462258A (en) * 1982-03-18 1984-07-31 King Engineering Corporation Pressure sensor and method of producing same

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB380431A (en) * 1931-04-10 1932-09-12 James Yate Johnson Improvements in the manufacture and production of assistants in the textile and related industries and dispersing agents

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0241050A2 (en) * 1986-04-08 1987-10-14 Hisamitsu Pharmaceutical Co., Inc. Azacycloalkane derivatives, absorption promoters containing the derivatives as the effective ingredient and external preparation containing the absorption promoters
WO1987006226A2 (en) * 1986-04-08 1987-10-22 Hisamitsu Pharmaceutical Co., Inc. Azacycloalkane derivatives, absorption promoters containing the derivatives as the effective ingredient and external preparations containing the absorption promoters
WO1987006226A3 (en) * 1986-04-08 1988-04-07 Hisamitsu Pharmaceutical Co Azacycloalkane derivatives, absorption promoters containing the derivatives as the effective ingredient and external preparations containing the absorption promoters
EP0241050A3 (en) * 1986-04-08 1988-12-28 Hisamitsu Pharmaceutical Co., Inc. Azacycloalkane derivatives, absorption promoters containing the derivatives as the effective ingredient and external preparation containing the absorption promoters
US4882359A (en) * 1986-04-08 1989-11-21 Hisamitsu Pharmaceutical Co., Ltd. Azacycloalkane derivatives, absorption promoters containing the derivatives as the effective ingredient and external preparations containing the absorption promoters

Also Published As

Publication number Publication date
GB947010A (en) 1964-01-22
DE1201058B (en) 1965-09-16
SE306533B (en) 1968-12-02

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