GB1001705A - Derivatives of 2,2-dihydroxybenzophenone - Google Patents

Derivatives of 2,2-dihydroxybenzophenone

Info

Publication number
GB1001705A
GB1001705A GB1121962A GB1121962A GB1001705A GB 1001705 A GB1001705 A GB 1001705A GB 1121962 A GB1121962 A GB 1121962A GB 1121962 A GB1121962 A GB 1121962A GB 1001705 A GB1001705 A GB 1001705A
Authority
GB
United Kingdom
Prior art keywords
acid
substituted
trihydroxy
prepared
alkyl
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
GB1121962A
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
Application filed by General Aniline and Film Corp filed Critical General Aniline and Film Corp
Publication of GB1001705A publication Critical patent/GB1001705A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
    • C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • 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
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives thereof
    • 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/123—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/133—Hydroxy compounds containing aromatic rings
    • 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/19—Hydroxy compounds containing aromatic rings
    • C08G63/193—Hydroxy compounds containing aromatic rings containing two or more aromatic rings
    • 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
    • C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/547—Hydroxy compounds containing aromatic rings
    • 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/682—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens
    • C08G63/6824—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/6826—Dicarboxylic acids and dihydroxy compounds
    • 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
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C08K5/132—Phenols containing keto groups, e.g. benzophenones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3477—Six-membered rings
    • C08K5/3492—Triazines
    • C08K5/34922—Melamine; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/06—Unsaturated polyesters

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

Polymers which are stable to ultra-violet light are derived from 2,21-dihydroxybenzophenones substituted in the 4-position by groups -O-CO-R-CO-X, in which R is the residue of a di-, tri- or tetracarboxylic acid and X is Br, Cl, OH or C1- 9 alkoxy, and optionally substituted in the 41, 6 and 61 positions with the same group or OH or alkoxy in which the alkyl group is 1-18 carbon atoms and may optionally be substituted with halogen, alkoxy, hydroxyalkoxy, cyano or aryloxy. The other positions in the benzene rings may be substituted by halogen, alkyl, alkenyl, cyano, hydroxyalkyl, cyanoalkyl, halo-alkyl, SO2CH3, SO2CH2Ph, alkoxy or alkaryl. The compounds are prepared from a 2,21-dihydroxy benzophenone having one or both 4 positions hydroxyl substituted and a dicarboxylic acid, halide, anhydride or ester. Many such ketones are specified. Acids specified are oxalic, malonic, succinic, glutaric, adipic, pimelic, azelaic, maleic, sebacic, suberic, hexahydrophthalic, phthalic, isophthalic, terephthalic, naphthalic, tricarbalkylic, trimesic, trimesitic, pyromellitic, malic and citric. The product of this reaction may be reacted as acid, acid chloride or ester with hydroxyl or amino groups in another monomer, a prepolymer or a polymer, e.g. monomers and polymers of phenol/formaldehyde, melamine/formaldehyde, polyamides, aniline/formaldehyde, styrene, maleic and acrylic monomers. In Examples (1), (3), (7), (9), (11) and (16) polyesters are prepared from phthalic anhydride, succinic anhydride, diethylene glycol and (1) the monosuccinate of 2,4,21-hydroxy-41-methoxybenzophenone, (3) the monooxalate of 2,4,21 - trihydroxybenzophenone, (7) the monosuccinate of 2,4,21-trihydroxybenzophenone, (9) the monosuccinate of 2,4,21-trihydroxy - 31 - allylbenzophenone, (11) the monosuccinate of 2,21,4-trihydroxy-51-benzylsulphonylbenzophenone and (16) the monosuccinates of 2,4,21-trihydroxy-51-allylbenzophenone, 2,4,21 - trihydroxy - 51 - (b - cyano-b ,b - dibromo - a ,a - dichloroethyl) benzophenone, 2,4,21 - trihydroxy - 51 - b - phenylethylbenzophenone, 2,4,21,41 - tetrahydroxy - 5-b - methoxyethylbenzophenone and 2,4,21,41-tetrahydroxy - 5 - b - cyanoethylbenzophenone. The products are mixed with styrene. In Examples (2), (8), (10) and (13) polyestero resins are prepared from phthalic anhydride, glycerol, styrene and (2) the monophthalate of 2,4,21-trihydroxybenzophenone (8) the diphthalate of 2,21,4,41 - tetrahydroxybenzophenone, (10) the monophthalate of 2,4,21 - hydroxy - 41 - chlorobenzophenone and (13) the diphthalate of 2,4,21,41 - tetrahydroxy - 6 - g - chloropropylbenzophenone. In Examples (14) and (15) polyester resins are prepared from benzoyl peroxide, a styrene/maleic anhydride/phthalic anhydride/ethylene glycol polymer and (14) the monomaleate of 2,4,21-trihydroxy-41-methoxybenzophenone and (15) the monomaleate of 2,4,21-trihydroxybenzophenone. In Examples (4) and (5) melamine/formaldehyde resins are prepared from the monosuccinate of 2,4,21-trihydroxybenzophenone, melamine and formaldehyde. Specification 832,043 is referred to.ALSO:The invention comprises 2,21-dihydroxybenzophenones which are substituted in the 4-position by a group -O-CO-R-CO-X and optionally in the 6,41- or 61-positions by the same group, or by other groups such as -OH or substituted or unsubstituted alkoxy, aryloxy, aralkoxy or alkaryloxy radicals. In the formula, R is the nucleus of a polycarboxylic acid and X is halogen, e.g. Cl or Br, -OH or -O-C1- 9 alkyl. Other non - chromophoric groups including halogen, alkyl, cyano, hydroxyalkyl, cyanoalkyl, haloalkyl and alkyl- or aralkylsulphonyl may also be present, as substituents in the benzene nuclei. The compounds of the invention are prepared by introducing the -O-CO-R-CO-X group by reaction of the corresponding substituted benzophenone with the appropriate polycarboxylic acid, monoester, anhydride or acid chloride, or the thus formed acid (X = OH) is converted to the ester or acid halide, e.g. chloride or bromide. The hydroxybenzophenone starting materials are obtained by condensing the appropriately substituted salicylic acid with resorcinol in presence of phosphoric acid, zinc chloride and phosphorus oxychloride or trichloride. Specification 832,043 is referred to.
GB1121962A 1961-08-04 1962-03-23 Derivatives of 2,2-dihydroxybenzophenone Expired GB1001705A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US12924661A 1961-08-04 1961-08-04

Publications (1)

Publication Number Publication Date
GB1001705A true GB1001705A (en) 1965-08-18

Family

ID=22439090

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1121962A Expired GB1001705A (en) 1961-08-04 1962-03-23 Derivatives of 2,2-dihydroxybenzophenone

Country Status (3)

Country Link
CH (1) CH422820A (en)
DE (1) DE1495873A1 (en)
GB (1) GB1001705A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106565926A (en) * 2016-10-21 2017-04-19 广西师范学院 Anti-ultraviolet aging chain extender for polyurethane and preparation method thereof
CN118166445A (en) * 2024-05-15 2024-06-11 广东华阳内衣有限公司 Antibacterial deodorizing coffee carbon fiber fabric and preparation method thereof

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103156829B (en) * 2012-12-24 2014-09-17 山西医科大学 Application of polyhydroxy bromo-benzophenone compound and derivatives thereof in treatment and prevention of atherosclerosis

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106565926A (en) * 2016-10-21 2017-04-19 广西师范学院 Anti-ultraviolet aging chain extender for polyurethane and preparation method thereof
CN106565926B (en) * 2016-10-21 2019-04-23 广西师范学院 Chain extender and preparation method thereof of the polyurethane with anti-ultraviolet ageing function
CN118166445A (en) * 2024-05-15 2024-06-11 广东华阳内衣有限公司 Antibacterial deodorizing coffee carbon fiber fabric and preparation method thereof

Also Published As

Publication number Publication date
CH422820A (en) 1966-10-31
DE1495873A1 (en) 1969-04-10

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