GB361910A - Manufacture of condensation products of high molecular weight - Google Patents

Manufacture of condensation products of high molecular weight

Info

Publication number
GB361910A
GB361910A GB24410/30A GB2441030A GB361910A GB 361910 A GB361910 A GB 361910A GB 24410/30 A GB24410/30 A GB 24410/30A GB 2441030 A GB2441030 A GB 2441030A GB 361910 A GB361910 A GB 361910A
Authority
GB
United Kingdom
Prior art keywords
condensed
polyvinyl alcohol
product
aqueous solution
condensing
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
GB24410/30A
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Publication of GB361910A publication Critical patent/GB361910A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00Chemical modification by after-treatment
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00Chemical modification by after-treatment
    • C08F8/28Condensation with aldehydes or ketones

Landscapes

  • Chemical & Material Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Condensation products suitable for use as emulsifying agents are manufactured by condensing polyvinyl alcohol in aqueous solution with formaldehyde and urea at 45-50 DEG C., or with aldol and resorcinol at 70-75 DEG C.ALSO:Condensation products; moulding compositions; sizes; emulsions, making; printing; textiles, treating.--Condensation products of high molecular weight are manufactured by condensing a polyvinyl alcohol with an aldehyde and a body capable of condensing with aldehydes. The three components may be condensed simultaneously or the polyvinyl alcohol may be first condensed with the aldehyde and the product then condensed with the body capable of condensing with aldehydes. Under mild conditions products soluble in water are formed, whilst stronger heating causes the separation of an insoluble mass. As compounds capable of condensing with aldehydes are specified : phenols and derivatives thereof, aromatic amines such as aniline, acid amides such as urea, thiourea and p-toluenesulphamide, also substances of high molecular weight such as gelatin, casein, starch and mucilage. The reaction may be accelerated by substances which promote saponification or esterification. The procedure may be such that the formation of the polyvinyl alcohol and the condensation with the other components constitutes one operation. When the compound capable of condensing with aldehydes is a phenol, the products have a phenolic character and may be acylated or alkylated at the phenolic hydroxyl, or can be sulphonated. In examples : (1) polyvinyl alcohol (prepared by saponification of a fatty acid ester of polyvinyl alcohol, such as polyvinyl acetate, chloracetate or butyrate, in the presence of an acid or an alkaline catalyst) is condensed simultaneously with formaldehyde and urea in aqueous solution at 90-100 DEG C.; the product is a white, horn-like mass which can be used as a moulding composition; (2) a similar condensation is carried out at 45-50 DEG C. yielding a viscous homogeneous product which can be used for making emulsions, as a material for sizing and dressing, or for preparing dyestuff pastes for printing; (3) polyvinyl alcohol and glyoxal are condensed in aqueous solution at 50-60 DEG C. and the product condensed at the same temperature with thiourea; (4) an aqueous solution of polyvinyl alcohol, formaldehyde and phenol with a small amount of ammonia is boiled; the whitish plastic mass obtained is useful as a moulding composition; (5) chips of polyvinyl alcohol are suspended in ethanol and condensed at 50-60 DEG C. with benzaldehyde in the presence of hydrogen chloride; the product is condensed with commercial cresol by gently boiling, yielding a solution suitable for a lacquer; the resin may be isolated by distilling off the alcohol and is likewise useful for preparing lacquers; (6) polyvinyl alcohol, aldol and resorcinol are condensed in aqueous solution at 70-75 DEG C., yielding a viscous solution useful for making emulsions, as a material for sizing and dressing, or for preparing dyestuff pastes for printing; (7) polyvinyl alcohol (obtained by saponification of polyvinyl acetate and still containing about one-third of the acetyl groups originally present) is condensed by boiling in aqueous solution with formaldehyde and p-toluenesulphamide in the presence of sulphuric acid; the product is soluble in alcohol to produce lacquers; (8) polyvinyl alcohol (obtained by saponifying polyvinyl chloracetate) is condensed in methanol solution at 50-60 DEG C. with acetaldehyde in the presence of lactic acid, and the product is boiled on a water bath with aniline; the product is useful for preparing lacquers; (9) polyvinyl alcohol is condensed with formaldehyde in aqueous solution at 50 DEG C. and the product is gently boiled with an aqueous solution of casein; the product is useful as a moulding composition. Azo dyes may be produced by coupling a diazo-component with a condensation product prepared as above in which the compound capable of reacting with aldehydes is a phenol. The Specification as open to inspection under Sect. 91 (3) (a) comprises also an alternative process in which the aldehyde is first condensed with the third component and the product is caused to react with the polyvinyl alcohol. This subject-matter does not appear in the Specification as accepted.ALSO:Condensation products of high molecular weight are manufactured by condensing a polyvinyl alcohol with an aldehyde and a body capable of condensing with aldehydes. The three components may be condensed simultaneously, or the polyvinyl alcohol may be first condensed with the aldehyde and the product then condensed with the third component. Under mild conditions products soluble in water are formed, whilst stronger heating causes the separation of an insoluble mass. As compounds capable of condensing with aldehydes are specified: phenols and derivatives thereof, aromatic amines such as aniline, acid amides such as urea, thiourea, and p-toluenesulphamide, also substances of high molecular weight such as gelatin, casein, starch, and mucilage. The reaction may be accelerated by substances which promote saponification or esterification. The procedure may be such that the formation of the polyvinyl alcohol and the condensation with the other components constitutes one operation. In examples: (1) polyvinyl alcohol is condensed simultaneously with formaldehyde and urea in aqueous solution at 90-100 DEG C., yielding a white horn-like mass useful as a moulding composition; (2) the same substances are condensed at 45-50 DEG C., yielding a viscous homogeneous product suitable for sizing; (3) polyvinyl alcohol and glyoxal are condensed in aqueous solution at 50-60 DEG C. and the product condensed at the same temperature with thiourea; (4) an aqueous solution of polyvinyl alcohol, formaldehyde, and phenol with a small amount of ammonia is boiled; the whitish plastic mass obtained is useful as a moulding composition; (5) chips of polyvinyl alcohol suspended in ethanol are condensed at 50-60 DEG C. with benzaldehyde in the presence of hydrogen chloride and the product is condensed with commercial cresol by gently boiling; (6) polyvinyl alcohol, aldol, and resorcinol are condensed in aqueous solution at 70-75 DEG C. yielding a viscous solution useful for sizing; (7) polyvinyl alcohol (obtained by saponifying polyvinyl acetate and still containing about one-third of the acetyl groups originally present) is condensed by boiling in aqueous solution with formaldehyde and p-toluenesulphamide in the presence of sulphuric acid; (8) polyvinyl alcohol is condensed in methanol solution at 50-60 DEG C. with acetaldehyde in the presence of lactic acid, and the product is boiled on a water bath with aniline; (9) polyvinyl alcohol is condensed with formaldehyde in aqueous solution at 50 DEG C. and the product is gently boiled with an aqueous solution of casein; the product is useful as a moulding composition. The Specification as open to inspection under Sect. 91 (3) (a) comprises also an alternative process in which the aldehyde is first condensed with the third component and the product is caused to react with the polyvinyl alcohol. This subject-matter does not appear in the Specification as accepted.
GB24410/30A 1929-08-14 1930-08-14 Manufacture of condensation products of high molecular weight Expired GB361910A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE361910X 1929-08-14

Publications (1)

Publication Number Publication Date
GB361910A true GB361910A (en) 1931-11-16

Family

ID=6302444

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24410/30A Expired GB361910A (en) 1929-08-14 1930-08-14 Manufacture of condensation products of high molecular weight

Country Status (2)

Country Link
FR (1) FR700411A (en)
GB (1) GB361910A (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2420730A (en) * 1944-06-09 1947-05-20 Du Pont Treatment of polymers with acylamides and aldehydes
US2436080A (en) * 1943-05-17 1948-02-17 Du Pont Resinous composition of urea-aldehyde and hydrolyzed interpolymer of a vinyl ester
US2462252A (en) * 1944-01-25 1949-02-22 Weyerhaeuser Timber Co Production and use of synthetic resin
US2469431A (en) * 1945-09-27 1949-05-10 Carbide & Carbon Chem Corp Insolubilization of water-soluble hydroxyl-containing polymeric materials
US2481676A (en) * 1947-08-13 1949-09-13 Eastman Kodak Co Hardened polyvinyl alcohol silver halide photographic coatings
US2483330A (en) * 1941-05-19 1949-09-27 Ici Ltd Bonding fabrics
US2545683A (en) * 1947-05-24 1951-03-20 Universal Oil Prod Co Polyvinyl acetal resins
US2744875A (en) * 1951-06-14 1956-05-08 Lockheed Aircraft Corp Cellular phenolic resin materials
US2916468A (en) * 1957-03-20 1959-12-08 Union Bag Camp Paper Corp Polyvinyl alcohol containing ureaformaldehyde adehsive and method of preparing same

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1023882B (en) * 1955-02-25 1958-02-06 Hoechst Ag Process for the production of stable aqueous dispersions of curable synthetic resins

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2483330A (en) * 1941-05-19 1949-09-27 Ici Ltd Bonding fabrics
US2436080A (en) * 1943-05-17 1948-02-17 Du Pont Resinous composition of urea-aldehyde and hydrolyzed interpolymer of a vinyl ester
US2462252A (en) * 1944-01-25 1949-02-22 Weyerhaeuser Timber Co Production and use of synthetic resin
US2420730A (en) * 1944-06-09 1947-05-20 Du Pont Treatment of polymers with acylamides and aldehydes
US2469431A (en) * 1945-09-27 1949-05-10 Carbide & Carbon Chem Corp Insolubilization of water-soluble hydroxyl-containing polymeric materials
US2545683A (en) * 1947-05-24 1951-03-20 Universal Oil Prod Co Polyvinyl acetal resins
US2481676A (en) * 1947-08-13 1949-09-13 Eastman Kodak Co Hardened polyvinyl alcohol silver halide photographic coatings
US2744875A (en) * 1951-06-14 1956-05-08 Lockheed Aircraft Corp Cellular phenolic resin materials
US2916468A (en) * 1957-03-20 1959-12-08 Union Bag Camp Paper Corp Polyvinyl alcohol containing ureaformaldehyde adehsive and method of preparing same

Also Published As

Publication number Publication date
FR700411A (en) 1931-02-28

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