IE33366L - Alkyl sulphoxide/alkyl sulphone terminated oligomers - Google Patents

Alkyl sulphoxide/alkyl sulphone terminated oligomers

Info

Publication number
IE33366L
IE33366L IE154469A IE154469A IE33366L IE 33366 L IE33366 L IE 33366L IE 154469 A IE154469 A IE 154469A IE 154469 A IE154469 A IE 154469A IE 33366 L IE33366 L IE 33366L
Authority
IE
Ireland
Prior art keywords
styrene
oligomers
butadiene
acrylonitrile
ethyl
Prior art date
Application number
IE154469A
Other versions
IE33366B1 (en
Original Assignee
Uniroyal Inc
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 Uniroyal Inc filed Critical Uniroyal Inc
Publication of IE33366L publication Critical patent/IE33366L/en
Publication of IE33366B1 publication Critical patent/IE33366B1/en

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
    • C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/12—Polymerisation in non-solvents
    • C08F2/16—Aqueous medium
    • C08F2/22—Emulsion polymerisation
    • C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Paper (AREA)
  • Mutual Connection Of Rods And Tubes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

1283087 Sulphoxide and sulphone terminated oligomers; emulsion polymerization processes UNIROYAL Inc 7 Nov 1969 [19 Nov 1968] 54636/69 Heading C3P Oligomers having the formula are prepared by oxidizing an oligomer of the formula In the above formulµ R represents an alkyl group (primary, secondary or tertiary) having from 5-20 carbon atoms, R 1 and R 3 are each H, methyl, ethyl or -COOH, R 2 and R 4 are each H, methyl, ethyl, -COOH or -CH 2 COOH, Y is a strongly hydrophilic group selected from -COOH, -CONH 2 , -OCH 3 , -OC 2 H 5 , -CH 2 OH and X is either a group as defined for y or is a less hydrophilic group selected from -COOC 2 H 4 OH, a+b is from 2 to 50, and a/a+b is from 0 to 1 unless X is a said less hydrophilic group in which case a/a+b is less than 0À6, and n is 1 or 2. (Alkyl sulphide-terminated oligomers similar to those used as starting material are described in Specification 1,207,532.) Oxidation of the oligomers is suitably effected, generally in an aqueous medium, with hydrogen peroxide or ozone, e.g. at 30-90‹ C.; one mole equivalent of oxidizing agent yields the terminal sulphoxide derivative and two mole equivalents yields the corresponding sulphone. The new oligomers are soluble in water or can be rendered soluble in water (when they contain acidic groups) by conversion to salts, e.g. ammonium, substituted ammonium, alkali metal, alkaline earth metal and Group III metal salts. Monomers from which the oligomers are derived include acrylic acid, acrylonitrile, acrylamide, itaconic acid, methacrylic acid and methacrylamide. Oligomerization of the monomers is suitably effected in the presence of an appropriate mercaptan R-SH in an organic solvent, e.g. methanol or isopropanol, using as initiator ammonium persulphate, lauroyl peroxide or lauroyl peroxide/dimethyl aniline. The new oligomers are useful as emulsifiers in the emulsion polymerization of ethylenically unsaturated monomers, e.g. butadiene, butadiene-styrene, butadiene-acrylonitrile, butadiene vinylidene chloride, butadiene-methacrylonitrile (and corresponding monomer(s) in combination with a small amount of an unsaturated acid monomer, e.g. itaconic acid), styrene, styrene-acrylonitrile, styrene-methacrylonitrile, ethyl acrylate, ethyl acrylate-vinyl acetate, ethyl acrylate-methyl methacrylate, ethyl acrylate-styrene, ethyl acrylate-butyl acrylate, butyl acrylate-acrylonitrile, and combinations of an ester such as ethyl or butyl acrylate with a minor amount of a mixture of (a) styrene, methyl methacrylate, butyl acrylate or vinyl acetate with (b) acrylic, methacrylic or itaconic acid. In examples the monomers used are (a) butadiene, styrene and itaconic acid, and (b) styrene and acrylonitrile; in addition to the oligomeric emulsifiers used, other components present include potassium persulphate, tetrasodium salt of EDTA and t-dodecyl mercaptan. [GB1283087A]
IE154469A 1968-11-19 1969-11-13 Alkyl-sulfoxide and alkyl-sulfone terminated oligomers of ethylenically unsaturated monomers IE33366B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US77717568A 1968-11-19 1968-11-19

Publications (2)

Publication Number Publication Date
IE33366L true IE33366L (en) 1970-05-19
IE33366B1 IE33366B1 (en) 1974-05-29

Family

ID=25109499

Family Applications (1)

Application Number Title Priority Date Filing Date
IE154469A IE33366B1 (en) 1968-11-19 1969-11-13 Alkyl-sulfoxide and alkyl-sulfone terminated oligomers of ethylenically unsaturated monomers

Country Status (15)

Country Link
AT (2) AT304070B (en)
BE (1) BE741797A (en)
BR (1) BR6914155D0 (en)
CA (1) CA923905A (en)
CH (1) CH526591A (en)
DE (1) DE1957384A1 (en)
ES (2) ES373674A1 (en)
FI (1) FI50535C (en)
FR (1) FR2023631A1 (en)
GB (1) GB1283087A (en)
IE (1) IE33366B1 (en)
LU (1) LU59831A1 (en)
NL (1) NL163520C (en)
NO (1) NO133759C (en)
SE (2) SE396221B (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1526301A (en) 1975-07-23 1978-09-27 Ciba Geigy Ag Compositions of matter for use in the treatment of aqueous systems
US4189383A (en) 1975-07-23 1980-02-19 Ciba-Geigy Corporation Novel compositions of matter for use in the treatment of aqueous systems
US4110429A (en) 1976-12-30 1978-08-29 Colgate-Palmolive Company Antibacterial oral composition
GB2264301B (en) * 1992-02-10 1996-07-31 Toa Gosei Chem Ind A process for producing a polymer having excellent weatherability
US5618898A (en) * 1992-02-10 1997-04-08 Toagosei Chemical Industry Co., Ltd. Weather-resistant solvent-based coating obtained by polymerization with thioether bond converted to sulfone bond
CN110483774B (en) * 2019-08-06 2022-01-28 金发科技股份有限公司 Aromatic sulfone polymer and preparation method thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3203938A (en) * 1961-11-10 1965-08-31 American Cyanamid Co Process for copolymerizing an alkali metal ethylene sulfonate in lower saturated alcohols with free radical polymerization catalysts
CH465551A (en) * 1964-11-13 1969-01-15 Geigy Ag J R Process for dyeing or printing textile fibers made of linear polyesters, cellulose esters or synthetic polyamides with disperse dyes

Also Published As

Publication number Publication date
FI50535B (en) 1975-12-31
NL163520C (en) 1980-09-15
BE741797A (en) 1970-05-19
AT304070B (en) 1972-12-27
ES376148A1 (en) 1972-03-16
NO133759B (en) 1976-03-15
IE33366B1 (en) 1974-05-29
GB1283087A (en) 1972-07-26
SE396221B (en) 1977-09-12
BR6914155D0 (en) 1973-01-11
FI50535C (en) 1976-04-12
NL6916918A (en) 1970-05-21
FR2023631A1 (en) 1970-08-21
CH526591A (en) 1972-08-15
SE359826B (en) 1973-09-10
NO133759C (en) 1976-06-23
DE1957384A1 (en) 1970-06-11
LU59831A1 (en) 1970-01-19
AT305622B (en) 1973-03-12
ES373674A1 (en) 1972-02-01
NL163520B (en) 1980-04-15
CA923905A (en) 1973-04-03

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