GB1071488A - Stabilisation of vinyl halide resins and polyolefins against photodegradation with acyl-dihydroxybenzophenones - Google Patents

Stabilisation of vinyl halide resins and polyolefins against photodegradation with acyl-dihydroxybenzophenones

Info

Publication number
GB1071488A
GB1071488A GB4980663A GB4980663A GB1071488A GB 1071488 A GB1071488 A GB 1071488A GB 4980663 A GB4980663 A GB 4980663A GB 4980663 A GB4980663 A GB 4980663A GB 1071488 A GB1071488 A GB 1071488A
Authority
GB
United Kingdom
Prior art keywords
barium
cadmium
acyl
isooctyl
dihydroxybenzophenones
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
GB4980663A
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.)
Argus Chemical NV
Argus Chemical Corp
Original Assignee
Argus Chemical NV
Argus Chemical 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 Argus Chemical NV, Argus Chemical Corp filed Critical Argus Chemical NV
Publication of GB1071488A publication Critical patent/GB1071488A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/835—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups having unsaturation outside an aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Paints Or Removers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Vinyl halide resin and polyolefine compositions comprises as light stabilizers acyl dihydroxybenzophenones wherein the acyl group has 12 to 30 carbon atoms and is ortho to at least one of the hydroxyl groups, preferably of formula <FORM:1071488/C3/1> where the benzoyl and acyl groups are each ortho to at least one of the hydroxyl groups, n is 1 or 2 and R is a C11- 29 aliphatic radical, an alicyclic radical or a heterocyclic radical. Other stabilizers, e.g. heat stabilizers, such as mild alkalis, lead salts, organotin carboxylates and mercaptides, metal salts of carboxylic acids and phenols, organic phosphite, organic sulphides, epoxy compounds, substituted ureas and thioureas, 2-phenylindole, epoxy compounds, aromatic amines and polyhydric compounds, may also be present and extensive lists of such compounds are given. The compositions may also comprise plasticizers, parting agents, fillers and pigments, examples of which are given. Specified resins are vinyl chloride polymers and copolymers with vinyl acetate, styrene, maleic and fumaric acid esters, and mixtures thereof with chlorinated polyethylene and acrylonitrile/butadiene/styrene copolymers, after-chlorinated polyvinyl chloride, and polymers and copolymers of ethylene, propylene, butene - 1, pentene - 1, 3 - methylbutene - 1, 4-methylpentene-1 and styrene. Many suitable acyl dihydroxybenzophenones are specified and examples describe compositions comprising polyvinyl chloride and (1) 3,5-dilauroyl-2,4-dihydroxybenzophenone and barium/cadmium laurate; (2) 3-lauroyl- and/or 5-lauroyl-2,4-dihydroxy benzophenone, isooctyl epoxystearate, barium nonyl phenolate, cadmium 2-ethylhexoate, zinc 2-ethylhexoate, isooctyl diphenyl phosphite, dioctyl phthalate and stearic acid; (3) various compositions comprising barium/cadmium laurate, dibutyltin maleate and 2,2-bis(p-hydroxyphenyl)propane, dioctyl phthalate, chlorinated polyethylene, isooctyl di-phenyl phosphite, zinc 2-ethylhexoate, barium nonylphenolate, cadmium 2-ethylhexoate, isooctyl epoxystearate and various acyl dihydroxybenzophenones; and (4)3-stearoyl-2,4-dihydroxybenzophenone, sodium carbonate and phenylurea; chlorinated polyvinyl chloride and (3) 5 - stearoyl - 6 - methyl - 2,4 - di-hydroxy-benzophenone, dibutyltin maleate and 2,2-bis(p-hydroxyphenyl) propane; and vinyl chloride/vinyl acetate copolymer and (3) 3- stearoyl - 2,4 - dihydroxy - 21,41 - dipropyl benzophenone, isooctyl diphenyl phosphite, issoctyl epoxystearate and cadmium/barium - 2,4 - dihydroxy - 21,41 - dipropyl benzophenone, isooctyl diphenyl phosphite, issoctyl epoxystearate and cadmium/barium laurate.
GB4980663A 1962-12-21 1963-12-17 Stabilisation of vinyl halide resins and polyolefins against photodegradation with acyl-dihydroxybenzophenones Expired GB1071488A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US24635362A 1962-12-21 1962-12-21

Publications (1)

Publication Number Publication Date
GB1071488A true GB1071488A (en) 1967-06-07

Family

ID=22930305

Family Applications (2)

Application Number Title Priority Date Filing Date
GB1813865A Expired GB1071489A (en) 1962-12-21 1963-12-17 Acyl dihydroxy benzophenones
GB4980663A Expired GB1071488A (en) 1962-12-21 1963-12-17 Stabilisation of vinyl halide resins and polyolefins against photodegradation with acyl-dihydroxybenzophenones

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB1813865A Expired GB1071489A (en) 1962-12-21 1963-12-17 Acyl dihydroxy benzophenones

Country Status (2)

Country Link
DE (1) DE1518148B1 (en)
GB (2) GB1071489A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2131764T3 (en) * 1994-03-04 1999-08-01 Gen Electric USEFUL COATINGS TO ABSORB ULTRAVIOLET LIGHT.

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2891996A (en) * 1956-04-23 1959-06-23 Dow Chemical Co 2, 4-dihydroxy benzophenone derivatives

Also Published As

Publication number Publication date
GB1071489A (en) 1967-06-07
DE1518148B1 (en) 1969-12-04

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