GB803053A - Polymethacrolein reaction product - Google Patents

Polymethacrolein reaction product

Info

Publication number
GB803053A
GB803053A GB13381/55A GB1338155A GB803053A GB 803053 A GB803053 A GB 803053A GB 13381/55 A GB13381/55 A GB 13381/55A GB 1338155 A GB1338155 A GB 1338155A GB 803053 A GB803053 A GB 803053A
Authority
GB
United Kingdom
Prior art keywords
ammonium
products
amine
hydrogen
styrene
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
GB13381/55A
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.)
Aerojet Rocketdyne Holdings Inc
Original Assignee
General Tire and Rubber Co
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
Application filed by General Tire and Rubber Co filed Critical General Tire and Rubber Co
Publication of GB803053A publication Critical patent/GB803053A/en
Expired legal-status Critical Current

Links

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
    • C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
    • C08G2/06—Catalysts
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B22—CASTING; POWDER METALLURGY
    • B22C—FOUNDRY MOULDING
    • B22C1/00—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds
    • B22C1/16—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents
    • B22C1/20—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents of organic agents
    • B22C1/22—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents of organic agents of resins or rosins
    • B22C1/2206—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents of organic agents of resins or rosins obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • B22C1/222—Polyacrylates
    • 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
    • C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
    • C08G2/14—Polymerisation of single aldehydes not provided for in groups C08G2/08 - C08G2/12
    • 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
    • C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
    • C08G2/18—Copolymerisation of aldehydes or ketones
    • 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
    • C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
    • C08G2/30—Chemical modification by after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
    • C08L1/08—Cellulose derivatives
    • C08L1/22—Cellulose xanthate
    • C08L1/24—Viscose
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3757—(Co)polymerised carboxylic acids, -anhydrides, -esters in solid and liquid compositions
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Textile Engineering (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A detergent composition comprises a substantially linear product having an average molecular weight of at least 500 which contains units of the formula: <FORM:0803053/III/1> where X is a cation such as hydrogen, ammonium, sodium, potassium, lithium or calcium, or an organic base such as di-isobutyl amine, di-isopropyl amine, benzylamine or piperidine, (see Group IV (a), mixed with one to five times its weight of a phosphate such as an orthophosphate or metaphosphate, or preferably sodium tripolyphosphate or a thermal decomposition product resulting from drying sodium tripolyphosphate at a drying medium temperature in excess of 212 DEG F. Alkali may be added.ALSO:Relates to a substantially linear product having an average molecular weight of at least 500 which contains units of the formula <FORM:0803053/IV (a)/1> where X is a cation such as hydrogen, ammonium, sodium, potassium, lithium or calcium, or an organic base such as di-isobutyl amine, diisopropyl amine, benzylamine or piperidine. Products other than those in which X is hydrogen or ammonium may be obtained by reacting an aqueous dispersion of a polymer or copolymer of methacrolein with a base having a diisociation constant greater than that of ammonium hydroxide at 25 DEG C. Products in which X is hydrogen may be obtained by acidifying the products of the above reaction, and products in which X is ammonium may be obtained by dissolving the acid products in ammonium hydroxide. Compounds with which the methacrolein may be copolymerized to form the initial copolymer include butadiene, isoprene, chloroprene, cyanoprene, dimethyl butadiene, styrene, acrylonitrile, methyl isopropenyl ketone, vinyl chloride, vinyl acetate and maleic or fumaric acid or anhydride. The reaction products, in their free acid, ammonium salt or amine salt form, may be converted to a lactone by heating and drying, or by treating with a salt such as aluminium sulphate, zinc chloride or copper sulphate. The reaction products may be used as emulsifiers in emulsion polymerization processes, and an example describes the copolymerization of styrene and 3,4-dichloro-alpha-methylstyrene in aqueous emulsion using paramenthane peroxide as catalyst, and the product in which X is sodium as emulsifier; other copolymers which may be made in this way include styrene-butadiene, methyl isopropenyl ketone - butadiene, styrene - methyl methacrylate, and vinyl chloride-methyl acrylate. The products may be used as soil conditioners and soil stabilizers, and in the treatment of fabrics, fibres and filaments; they may be used as warp sizes and as sizes and finishing agents for paper and boxboard; they may be added to viscose dope and may serve as binders for sand cores and moulds; they may be mixed with phosphates such as sodium tripolyphosphate to form detergent compositions, and aqueous solutions of the ammonium and amine salt form of the product admixed with a pigment such as titanium dioxide may be used as intumescent paints.ALSO:Textile fibres and fabrics such as wool, cotton, nylon and rayon or glass filaments may be sized by contacting the fabric &c. with an aqueous solution of a polymer which comprises recurring units of the structural formula <FORM:0803053/IV (c)/1> where X is ammonium or an amine having less than four carbon atoms (see Group IV (a)) and drying and heating the fabric &c. to form a water-insoluble lactone having the structure <FORM:0803053/IV (c)/2> The lactones may also be formed by treating the polymer with a salt such as aluminium sulphate, zinc chloride or copper sulphate. By this treatment the fabrics &c. are creaseproofed and shrinkproofed.ALSO:A substantially linear product having an average molecular weight of at least 500 and containing units of the formula:- <FORM:0803053/I/1> where X is a cation (see Group IV(a)) may be used for conditioning soil.
GB13381/55A 1954-05-13 1955-05-09 Polymethacrolein reaction product Expired GB803053A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US803053XA 1954-05-13 1954-05-13

Publications (1)

Publication Number Publication Date
GB803053A true GB803053A (en) 1958-10-15

Family

ID=22156534

Family Applications (1)

Application Number Title Priority Date Filing Date
GB13381/55A Expired GB803053A (en) 1954-05-13 1955-05-09 Polymethacrolein reaction product

Country Status (3)

Country Link
DE (3) DE1054055B (en)
FR (1) FR1131993A (en)
GB (1) GB803053A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3121700A (en) * 1959-12-14 1964-02-18 Shell Oil Co Soluble nitrogen-containing derivatives of unsaturated aldehyde polymers, their preparation and use
US3141864A (en) * 1959-06-05 1964-07-21 Degussa Process for the production of polymerizates or mixed polymerizates of acrolein and methacrolein
US3148165A (en) * 1959-05-13 1964-09-08 Gen Tire & Rubber Co Reaction product of salt of acrolein type polymer and mono primary amine
US3167529A (en) * 1959-12-14 1965-01-26 Shell Oil Co Process for preparing high molecular weight polymers of unsaturated aldehydes and resulting products
US3177171A (en) * 1959-10-08 1965-04-06 Gen Tire & Rubber Co Process for reacting ammonia or a primary amine with an acrolein polymer and resulting product
US3322725A (en) * 1962-08-07 1967-05-30 Shell Oil Co Process for preparing polymers having a high percent of free carbonyl and resulting products
US3420798A (en) * 1965-06-23 1969-01-07 Gulf Oil Corp Cross-linked polymers of lactonized poly (methyl propenol/methacrylic acid) and method of preparing by applying heat

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL120503C (en) * 1958-07-03
DE1904941A1 (en) * 1969-02-01 1970-08-06 Degussa Polyoxycarboxylic acids

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2212894A (en) * 1937-11-08 1940-08-27 Shell Dev Polymerization of unsaturated aldehydes
DE880388C (en) * 1944-11-29 1953-06-22 Siemens Ag Mass for molded shells for metal or iron casting
DE1189677B (en) * 1952-05-15 1965-03-25 Monsanto Co Molding sand mixtures for casting metals

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3148165A (en) * 1959-05-13 1964-09-08 Gen Tire & Rubber Co Reaction product of salt of acrolein type polymer and mono primary amine
US3141864A (en) * 1959-06-05 1964-07-21 Degussa Process for the production of polymerizates or mixed polymerizates of acrolein and methacrolein
US3177171A (en) * 1959-10-08 1965-04-06 Gen Tire & Rubber Co Process for reacting ammonia or a primary amine with an acrolein polymer and resulting product
US3121700A (en) * 1959-12-14 1964-02-18 Shell Oil Co Soluble nitrogen-containing derivatives of unsaturated aldehyde polymers, their preparation and use
US3167529A (en) * 1959-12-14 1965-01-26 Shell Oil Co Process for preparing high molecular weight polymers of unsaturated aldehydes and resulting products
US3322725A (en) * 1962-08-07 1967-05-30 Shell Oil Co Process for preparing polymers having a high percent of free carbonyl and resulting products
US3420798A (en) * 1965-06-23 1969-01-07 Gulf Oil Corp Cross-linked polymers of lactonized poly (methyl propenol/methacrylic acid) and method of preparing by applying heat
US3474062A (en) * 1965-06-23 1969-10-21 Gulf Oil Corp Partially lactonized polymers of poly-(methyl propenol/methacrylic acid)

Also Published As

Publication number Publication date
DE1265918B (en) 1968-04-11
DE1024714B (en) 1958-02-20
DE1054055B (en) 1959-04-02
FR1131993A (en) 1957-03-04

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