EP1383832A1 - Stabilized candle wax - Google Patents

Stabilized candle wax

Info

Publication number
EP1383832A1
EP1383832A1 EP02716843A EP02716843A EP1383832A1 EP 1383832 A1 EP1383832 A1 EP 1383832A1 EP 02716843 A EP02716843 A EP 02716843A EP 02716843 A EP02716843 A EP 02716843A EP 1383832 A1 EP1383832 A1 EP 1383832A1
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
hydroxy
alkyl
tert
substituted
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.)
Withdrawn
Application number
EP02716843A
Other languages
German (de)
French (fr)
Inventor
Mervin Gale Wood
Andrea R. Roberts
Deborah Judd
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.)
BASF Schweiz AG
Ciba SC Holding AG
Original Assignee
Ciba Spezialitaetenchemie Holding AG
Ciba SC Holding 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
Priority claimed from US09/824,194 external-priority patent/US6544305B2/en
Priority claimed from US09/825,552 external-priority patent/US6562084B2/en
Priority claimed from US09/824,146 external-priority patent/US6544304B2/en
Priority claimed from US09/824,048 external-priority patent/US6547840B2/en
Priority claimed from US09/824,141 external-priority patent/US6540795B2/en
Application filed by Ciba Spezialitaetenchemie Holding AG, Ciba SC Holding AG filed Critical Ciba Spezialitaetenchemie Holding AG
Publication of EP1383832A1 publication Critical patent/EP1383832A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C5/00—Candles
    • C11C5/002—Ingredients
    • 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
    • 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
    • C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
    • C08L91/06—Waxes

Definitions

  • the instant invention pertains to white, dyed, dipped, unscented and/or scented candle wax which is effectively stabilized against discoloration and fading by the incorporation therein of a morpholinone, an oxazolidine, an imidazolidine, a piperazindione or a piperazinone, in combination with an UV absorber and/or an antioxidant.
  • candles have been known for many centuries going back to the eighth century B.C. The nature of candles is described in Ullmann's Encyclopedia of Industrial Chemistry, Volume A5 at pages 29-30 where it is seen that candles are made from paraffin, beeswax and stearin as basic materials, and where a host of additives may also be present.
  • EP 359,488 A3 and EP 133,964 B1 describe stabilized waxes used in cosmetics where the waxes are the same or similar to those used in candles.
  • EP 5,922 A1 describes lip cosmetics where the waxes are useful in lipsticks and are related to those useful in candles.
  • the light absorbers compared are 4-octyloxy-2-hydroxybenzophenone UV-531 ; 4- methoxy-2-hydroxybenzophenone UV-9; 2-(2-hydroxy-5-methylphenyl)-2H-benzotriazole UV- 5365; 2-(2-hydroxy-5-tert-octylphenyl-2H-benzotriazole UV-5411 and 2-(2-hydroxy-3,5-di-tert- amylphenyl)-2H-benzotriazole UV-2337).
  • United States Patent No. 5,964,905 teaches dyed and scented candle gels containing triblock copolymers and a hydrocarbon oil of high flash point.
  • a light (UV) absorber may be used to improve the shelf stability of the candle color when exposed to visible or ultraviolet light.
  • Two preferred absorbers are ethylhexyl p-methoxycinnamate (PARSOL® MCX, Roche) and 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole (CYASORB® 5411 , Cytec).
  • WO 00/22037 teaches the stabilization of solid, shaped and colored wax articles, including candles, using a malonate UV absorber which may optionally contain a hindered amine moiety as part of the malonate compound structure.
  • the wax articles are dyed with a variety of oil soluble dyes and pigments.
  • the samples protected by dimethyl p-methoxybenzylidinemalonate exhibited better resistance to discoloration that did samples stabilized with selected benzotriazole or benzophenone UV absorbers.
  • Japanese Hei 3-278554 teaches that wax crayons (drawing materials) colored by organic pigments can be stabilized by a hindered amine and/or benzotriazole.
  • United States Patent No. 4,547,537 teaches tetrahydro-1 ,4-oxazin-2-one moieties attached to a substituted piperidinyl hindered amine group as stabilizers for polyolefins and other polymeric substrates.
  • United States Patent Nos. 4,797,451 and 4,853,440 described paraffinic polymers such as polybutadiene or polyisoprene that have inter alia morpholinone moieties reacted into the polymer backbone.
  • United States Patent Nos. 4,528,370; 4,914,232 and 5,089,614 describe morpholinone compounds which are useful as light stabilizers.
  • WO 98/44008 describes a controlled free radical polymerization process using inter alia selected morpholinone based nitroxide groups.
  • WO 00/39209 teaches polymeric stabilizers having low polydispersity and having inter alia pendant morpholinone groups.
  • WO 99/46261 describes nitroxyl derivatives with glycidyl or alkylcarbonyl groups as initiators for radical polymerization. Some such nitroxyl derivatives may also contain morpholinone groups.
  • German Offenlegunsschrift DE 198 45 298 A1 describes N-oxyl radicals of morpholinone derivatives useful in free radical polymerization.
  • British 2,342,649 A describes heterocyclic alkoxyamines as regulators in controlled free radical polymerization processes inter alia these include molecules which contain morpholinone moieties.
  • WO 99/14206 depicts morpholinone compounds as light stabilizers for organic material especially for coatings.
  • WO 00/14177 teaches the inhibition of vinyl monomer polymerization using hindered hydroxylamines some of which may contain an oxazolidine moiety. There is no suggestion that any of these compounds would be stabilizers for candle wax.
  • United States Patent Nos. 5,264,148 and 5,223,174 describe various mono- and bicyclic oxazolidine compounds which have the property of scavenging moisture particularly aimed at efficiently, cost effectively and safely removing water from moisture-curable polyurethane coating systems or any other water-sensitive system where residual water is a problem.
  • United States Patent Nos. 3,707,541 and 3,825,555 describe the use of oxazolidine and tetrahydrooxazine compounds as insect repellents.
  • United States Patent Nos. 4,017,406, 4,116,643 and 4.369,118 describe oxazoline compounds and amine salts of carboxylate half esters of 1-aza-3,7-dioxabicyclo[3,3,0]oct-5-yl methyl alcohols as additives for lubricating oils, gasoline, middle distillate fuels and other oleaginous products.
  • United States Patent Nos. 5,328,635 and 5,433,891 disclose iminoalcohol-oxazolidine mixtures which are useful as corrosion inhibitors, moisture or formaldehyde scavengers, drying agents and the like.
  • WO 98/11181 describes substituted oxazolines, related to oxazolidines, which are antioxidants and antioxidant boosters capable of producing hydroperoxyl radicals.
  • WO 99/05108 teaches the inhibition of pulp or paper which contains lignin from yellowing by use inter alia of a substituted oxazolidine or a salt thereof.
  • Imidazolidines have been known as stabilizers for various substrates.
  • British Patent No. 1 Imidazolidines have been known as stabilizers for various substrates.
  • United States Patent No. 4,448,969 discloses the use of cyclic ether or carbonate alkylation products of 2,2,5,5-tetramethylimidazolidin-4-one for the stabilization of synthetic polymers, particularly polyolefins.
  • United States Patent Nos. 4,804,717 and 4,895,901 teach that polymeric hindered amine light stabilizers are useful for the stabilization of olefin, styrene and acrylate polymers which contain a minor amount of a pendant moiety derived from 3-hydroxy-2,2,5,5-tetramethylimidazolidine-4- one.
  • European Patent Specification 313,941 B1 describes the stabilization of photochromic dye compositions using 1 -oxyl-2,2,5,5-tetramethylimidazolidin-4-one.
  • United States Patent No. 6,020,491 teaches the use of monomeric and polymeric cyclic amine and N-halamine compounds as biocides and disinfectants for a host of substrates. Some of the structures include a substituted 2,2,5,5-tetramethylimidazolidine moiety in a pendant group.
  • WO 98/30601 describes a method of controlling polymer molecular weight and polymer structure by living free radical polymerization where nitroxide and alkoxyamine containing a 2,2,5,5-tetramethylimidazolidine moiety are employed.
  • WO 99/61396 teaches the method of stabilizing unsaturated organic polymers using a host of polymerization inhibitors based on the alkylated 2,2,5,5-tetramethylimidazolidine compounds.
  • WO 98/44008 teaches controlled free radical polymerization processes using a stable free radical agent which is a piperazinone, piperazindione or morpholinone based nitroxide.
  • a stable free radical agent which is a piperazinone, piperazindione or morpholinone based nitroxide.
  • United States Patent No. 3,936,456 describes substituted piperazinedione oxyl and hydroxylamine derivaties useful in stabilizing polyolefins.
  • United States Patent No. 4,413,096 depicts olefin copolymers having pendant hindered amine groups inter alia one containing a piperazindione moiety.
  • German Offenlegungsschrift DE 199 24 984 A1 describes compositions stabilized by a host of piperazindione derivatives.
  • United States Patent No. 6,117,995 depicts the preparation of sterically hindered amine ethers where the cyclic ring is inter alia a piperazinone. These compounds are useful as stabilizers.
  • the instant invention pertains to a composition which comprises
  • the morpholinone compound is preferably a compound of formula la-100 or lb-100
  • R 10 ⁇ is hydrogen, alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms or cycloalkenyl of 5 to 12 carbon atoms;
  • R 102 has the same meaning as R 10 ⁇ ; or R 102 is also hydroxyalkyl of 1 to 8 carbon atoms; or R 10 ⁇ and R 102 together are tetramethylene, pentamethylene or pentamethylene substituted by methyl; R 103 has the same meaning as R 10 ⁇ ;
  • R ⁇ 04 has the same meaning as R ⁇ 02 ; or R 103 and R 104 together are tetramethylene, pentamethylene or pentamethylene substituted by methyl;
  • R 105 is hydrogen; alkyl of 1 to 18 carbon atoms; alkyl of 2 to 18 carbon atoms substituted by hydroxy, by phenyl or by both hydroxy and phenyl; oxyl; hydroxy; cyanoalkyl of 2 to 12 carbon atoms; cyanoalkoxy of 2 to 12 carbon atoms; alkoxy of 1 to 18 carbon atoms; cycloalkoxy of 5 to 12 carbon atoms; alkenyl of 3 to 8 carbon atoms; alkenyloxy of 3 to 8 carbon atoms; phenylaikyl of 7 to 12 carbon atoms; phenylaikyl of 7 to 12 carbon atoms substituted by hydroxy, by alkyl of 1 to 4 carbon atoms or by alkoxy of 1 to 4 carbon atoms, or by both said alkyl and said alkoxy; phenylalkoxy of 7 to 12 carbon atoms; alkanoyl of 2 to 8 carbon atoms; or a substituted 2,
  • R 106 is a straight or branched chain alkyl of 1 to 24 carbon atoms which is unsubstituted or substituted by one to six hydroxy or -OR ⁇ groups; or R ⁇ 06 is phenyl; when n 100 is 2;
  • Rio ⁇ is alkylene of 2 to 12 carbon atoms, o-phenylene, m-phenylene, p-phenylene or p-xylylene; and R 10 is hydrogen or has the meaning of R 10 ⁇ -
  • the oxazolidine compound is preferably a compound of formula la-200, lla-200 or llla-200
  • R 2 0 1 , R20 2 , R 20 3 and R 2 o are independently alkyl of 1 to 8 carbon atoms, or R 20 ⁇ and R 202 together or R 2 o 3 and R 204 together are tetramethylene, pentamethylene or pentamethylene substituted by methyl;
  • R 205 is hydrogen, oxyl, hydroxy, aralkyl of 7 to 15 carbon atoms, alkoxy of 1 to 24 carbon atoms, alkyl of 1 to 42 carbon atoms, said alkyl substituted by one or two hydroxy groups, said alkyl substituted by alkylcarbonyloxy of 2 to 18 carbon atoms, or said alkyl interrupted by one to twenty oxygen atoms and substituted by one hydroxy, by alkylcarbonyloxy of 2 to 18 carbon atoms or by 4-hydroxy-3,5-di-tert-butylbenzoyloxy; or R 2 os is -CO-C n H 2 ⁇ +1 where n is 1 to 17, and
  • R 206 is alkyl of 1 to 8 carbon atoms, said alkyl substituted by one or two hydroxy groups, or is aryl of 6 to 10 carbon atoms.
  • the imidazoline compound is preferably a compound of formula la-300
  • R 301 and R 302 are independently alkyl of 1 to 8 carbon atoms, or R 30 ⁇ and R 302 together are tetramethylene, pentamethylene or pentamethylene substituted by methyl; and R 303 and R 30 are independently hydrogen, oxyl, hydroxy, aralkyl of 7 to 15 carbon atoms, alkoxy of 1 to 24 carbon atoms, alkyl of 1 to 42 carbon atoms, said alkyl substituted by one or two hydroxy groups, said alkyl substituted by alkylcarbonyloxy of 2 to 18 carbon atoms, or said alkyl interrupted by one to twenty oxygen atoms and substituted by one hydroxy, by alkylcarbonyloxy of 2 to 18 carbon atoms or by 4-hydroxy-3,5-di-tert-butylbenzoyloxy.
  • the piperazindione compound is preferably a compound of formula la-400
  • G 400 is alkyl of 1 to 18 carbon atoms, alkyl of 2 to 18 carbon atoms substituted by -NH 2 , by -OH, by halogen, by -OR 6 or by 4-hydroxy-3,5-di-tert-butylphenyl or by 4-hydroxy-3,5-dimethylphenyl, or by a mixture of these groups; or is interrupted by -O-, by -NH- or by -NR 06 - or by a mixture of said groups; or G 0 o is alkyl of 1 to 18 carbon atoms substituted by -COOR 407 or by phenyl; when p 400 is 2,
  • G 400 is alkylene of 2 to 10 carbon atoms, alkenylene of 4 to 12 carbon atoms, alkylene of 3 to 15 carbon atoms substituted by one to four -OH or said alkylene interrupted by one to four oxygen atoms; or G 400 is phenylene, C C alkylphenylene, -COO-, -CONH-,
  • R 403 and R 404 are independently alkyl of 1 to 12 carbon atoms, said alkyl substituted by one or two hydroxy groups; or R 40 ⁇ and R 40 together, R 403 and R 04 together or R 401 and R 402 together and with R 03 and R 04 together are tetramethylene, pentamethylene or pentamethylene substituted by methyl;
  • R 405 is hydrogen, oxyl, hydroxy, cyanoethyl, phenylaikyl of 7 to 15 carbon atoms, said phenylaikyl substituted on the phenyl ring by one to three radicals selected from alkyl of 1 to 4 carbon atoms and alkoxy of 1 to 4 carbon atoms, phenylalkoxy of 7 to 15 carbon atoms, said phenylalkoxy substituted on the phenyl ring by one to three radicals selected from alkyl of 1 to 4 carbon atoms and alkoxy of 1 to 4 carbon atoms, cycloalkoxy of 5 to 12 carbon atoms, alkenyl of 3 to 8 carbon atoms, alkynyl of 3 to 8 carbon atoms, alkoxy of 1 to 24 carbon atoms, alkyl of 1 to 24 carbon atoms, said alkyl substituted by one or two hydroxy groups, said alkyl substituted by alkylcarbonyloxy of 2 to 18 carbon atom
  • Z 4Q0 is -NH 2 , -NHR 40 6, -N(R 406 ) 2 or alkoxy of 1 to 18 carbon atoms;
  • R 406 is alkyl of 1 to 8 carbon atoms, alkanoyl of 1 to 8 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylaikyl of 7 to 15 carbon atoms which is unsubstituted or substituted on the phenyl ring by alkyl of 1 to 4 carbon atoms, by alkoxy or 1 to 4 carbon atoms or by a mixture of said groups; or R 4 o ⁇ is alkyl of 1 to 8 carbon atoms or alkanoyl of 1 to 8 carbon atoms substituted by -OH, by alkoxy of 1 to 12 carbon atoms, by benzophenonyl or benzophenonyloxy where one or both phenyl rings of the benzophenone moiety are unsubstituted or substituted by -OH, by halogen, by alkyl of 1 to 4 carbon atoms, by alkoxy of 1 to 4 carbon atoms or by a mixture of such groups; and
  • R 407 is alkyl of 1 to 18 carbon atoms, alkyl of 2 to 18 carbon atoms which is substituted by -NH 2 , by by -N(R 406 ) 2 , by nitro, by hydroxy, by alkoxy of 1 to 18 carbon atoms or by a mixture of said groups; or R ⁇ is alkenyl of 3 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, or said cycloalkyl which is substituted by alkyl of 1 to 4 carbon atoms or is interrupted by -O-.
  • the piperazinone compound is preferably a compound of formula II-500 or III-500 wherein n 50 o is 1 or 2, p 500 is 1 to 12, when n 500 is 1 ,
  • G 500 is alkyl of 1 to 18 carbon atoms, alkyl of 2 to 18 carbon atoms substituted by -NH 2 , by
  • G 50 o is alkyl of 2 to 18 carbon atoms interrupted by -O-, by -CO-, by -NH- or by -NR 506 - or by a mixture of said groups; or G 500 is alkyl of 1 to 18 carbon atoms substituted by -COOR 507 or by phenyl; when n 500 is 2,
  • G 500 is alkylene of 2 to 10 carbon atoms, alkenylene of 4 to 12 carbon atoms, alkylene of 3 to 15 carbon atoms substituted by one to four -OH or said alkylene interrupted by one to four oxygen atoms; or G 500 is phenylene, C C 4 alkylphenylene, -CO-(CH 2 ) P5 oo-CO-, -COO-, -CONH-,
  • R ⁇ 02 > R503 and R 50 are independently alkyl of 1 to 12 carbon atoms, said alkyl substituted by one or two hydroxy groups; or R 50 ⁇ and R 502 together, R 503 and R 504 together or R 50 ⁇ and R 502 together and with R 503 and R 504 together are tetramethylene, pentamethylene or pentamethylene substituted by methyl;
  • R505 >s hydrogen, oxyl, hydroxy, cyanoethyl, phenylaikyl of 7 to 15 carbon atoms, said phenylaikyl substituted on the phenyl ring by one to three radicals selected from alkyl of 1 to 4 carbon atoms and alkoxy of 1 to 4 carbon atoms, phenylalkoxy of 7 to 15 carbon atoms, said phenylalkoxy substituted on the phenyl ring by one to three radicals selected from alkyl of 1 to 4 carbon atoms and alkoxy of 1 to 4 carbon atoms, cycloalkoxy of 5 to 12 carbon atoms, alkenyl of 3 to 8 carbon atoms, alkynyl of 3 to 8 carbon atoms, alkoxy of 1 to 24 carbon atoms, alkyl of 1 to 24 carbon atoms, said alkyl substituted by one or two hydroxy groups, said aikyl substituted by alkylcarbonyloxy of 2 to 18
  • Z500 is -NH 2 , -NHR506, -N(R 50 6)2 or alkoxy of 1 to 18 carbon atoms;
  • R 506 is alkyl of 1 to 8 carbon atoms, alkanoyl of 1 to 8 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylaikyl of 7 to 15 carbon atoms which is unsubstituted or substituted on the phenyl ring by alkyl of 1 to 4 carbon atoms, by alkoxy of 1 to 4 carbon atoms or by a mixture of said groups; or R 506 is alkyl of 1 to 8 carbon atoms or alkanoyl of 1 to 8 carbon atoms substituted by -OH, by alkoxy of 1 to 12 carbon atoms, by benzophenonyl or benzophenonyloxy where one or both phenyl rings of the benzophenone moiety are unsubstituted or substituted by -OH, by halogen, by alkyl of 1 to 4 carbon atoms, by alkoxy of 1 to 4 carbon atoms or by a mixture of such groups; R 507 is hydrogen
  • R 0 ⁇ , R 202 , R 203 and R 204 are each methyl, or R 20 ⁇ and R 202 together and R 203 and R 20 together are pentamethylene.
  • R 30 ⁇ and R 302 are each methyl, or R 30 ⁇ and R 302 together are pentamethylene.
  • R 40 ⁇ , R 4 o 2 , R 4 o 3 and R 04 are each methyl, or R ⁇ and R 402 together and R 403 and R 04 together are pentamethylene.
  • R503 and R 504 are each preferably methyl, or R 501 and R 502 together and R 503 and R 50 together are preferably pentamethylene.
  • R 505 is preferably hydrogen or methyl.
  • R 508 is preferably n-butyl or cyclohexyl.
  • aryl is phenyl and an example of aralkyl is benzyl.
  • the compounds (a-100), (b-100), (c-100) and (d-100) are particularly preferred.
  • the compound (a-300) is particularly preferred.
  • the compounds (a-400) and (b-400) are particularly preferred.
  • the compounds (a-500), (b-500) and (c-500) are particularly preferred.
  • the ratio by weight of components (i) to (ii) is from 4:1 to 1 :4, in particular from 2:1 to 1 :2.
  • the total amount of components (i) and (ii) are 0.01 to 10%, preferably 0.1 to 2 %, in particular 0.1 to 0.5%, by weight based on the wax.
  • the UV absorber of component (ii) is for example a benzotriazole, a benzophenone, an ⁇ - cyanoacrylate, an oxanilide, an s-triazine, a cinnamate, a malonate, a benzoate or a salicylate, or a mixture thereof, in particular a benzotriazole, a benzophenone or an s-triazine.
  • UV absorbers useful in the instant invention are:
  • UV absorbers (a), (b), (d), (o), (p), (q), (y) and (z) are particularly preferred.
  • Another embodiment of the instant invention involves a composition wherein the antioxidant is a phenolic antioxidant, a phosphite, a nitrone, an amine oxide or a hydroxylamine, or mixture thereof.
  • the antioxidant is a phenolic antioxidant, a phosphite, a nitrone, an amine oxide or a hydroxylamine, or mixture thereof.
  • antioxidants useful in this invention are:
  • antioxidants (a'), (b'), (d'), (f), (h') and (i') are particularly preferred.
  • candles contain a host of various components.
  • the base materials may be made up of the following:
  • paraffin wax paraffin wax, natural oils, polyamide plus fatty acid/ester, fatty acids such as stearin, opacifiers, beeswax, glycerides plus oxidized wax, alcohols, and ethylene oligomers.
  • Candles also contain a number of additives such as the following:
  • mold release agents fragrances, insect repellants or insecticides, hardeners, crystal modifiers, clarifiers, guttering reducers, colorants, f.p. control agents, stretchability improvers, gelling agents, extrusion aids, and vortex reducers.
  • Each of the various components are meant to control or modify the properties of the candle to insure proper burning, reduce channelling, aid in uniform melting, and the like.
  • the colorants and fragrances obviously are there to provide the proper color, scent or other aesthetic appeal.
  • these gel candles usually contain a copolymer selected from the group consisting of a triblock, radial block, diblock or multiblock copolymer classically made up of at least two thermodynamically incompatible segments containing both hard and soft segments.
  • Typical of such block copolymers is KRATON® (Shell Chemical Co.) which consists of block segments of styrene monomer units and rubber monomer or comonomer units.
  • KRATON® D series is a linear ABA block with styrene-butadiene-styrene (SBS) or styrene-isoprene-styrene (SIS).
  • Wax samples are supplied by the Candle-Lite Corporation. These samples contain dyes and fragrances.
  • UV absorbers and hindered amine stabilizers are obtained from the Ciba Speciality Chemicals Corporation.
  • Triplicate samples of each disk are exposed under a bank of six (6) cool-white fluorescent lamps (40 watts) or under a bank of six (6) UV lamps having a wavelength of 368 nm with the test samples being twelve (12) inches (30.48 cm) below the lamps.
  • Dye color fade (or color change) is measured by a Macbeth ColorEye Spectrophotometer with a 6 inch integrating sphere. The conditions are: 10 degree observer; D65 illuminant and 8 degree viewing angle.
  • Example 101 5-hvdroxymethyl-3.3.5-trimethyl-2-morpholinone.
  • Example 103 5.5'-bis(decandioyloxvmethvl-3.3.5-trimethyl-2-morpholinone).
  • Example 104 5-dodecanovloxvmethvl-3.3.5-trimethvl-2-morpholinone.
  • ⁇ E values represent the change in color after the indicated days of exposure. A low ⁇ E value indicates less change in color and is highly desired.
  • A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
  • C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
  • E is 5-hydroxymethyl-3,3,5-trimethyl-2-morpholinone, the compound of instant Example 101.
  • A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
  • B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
  • C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
  • G is the reaction product of 2,4,6-tris(2,4-dihydroxyphenyl)-s-triazine with octyl ⁇ -haloacetate.
  • A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
  • B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
  • D is bis(1 ,2,2,6, 6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA.
  • G is the reaction product of 2,4,6-tris(2,4-dihydroxyphenyl)-s-triazine with octyl ⁇ -haloacetate.
  • H is 5-(2-ethylhexanoyloxymethyl)-3,3,5-trimethyl-2-morpholinone, the compound of instant
  • Example 103 These data show that a morpholinone compound (Compound H or I) in combination with a UV absorber protects the white scented candle wax from unwanted discoloration far better than conventional stabilizer systems.
  • Example 108 Color Fade of White Scented Candle Wax under UV Lamp Exposure.
  • B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
  • Green scented candle wax is well stabilized by 0.2% by weight of dimethyl p-methoxybenzylidenemalonate, SANDUVOR® PR 25, in combination with 0.2% by weight of N-(2,2,6,6- tetramethylpiperidin-4-yl)-tetrahydro-1 ,4-oxazin-2-one.
  • Yellow scented candle wax is well stabilized by 0.1% by weight of di(1 ,2,2,6,6-pentamethyl- piperidin-4-yl) p-methoxybenzylidenemalonate, SANDUVOR® PR 31 , in combination with 0.1% by weight of N-(1 ,2,2,6,6-pentamethylpiperidin-4-yl)-tetrahydro-6-methyl-1 ,4-oxazin-2-one.
  • Red unscented candle wax is well stabilized by 0.1% by weight of dimethyl di(p-chlorophenyl)- methylenemalonate in combination with 0.1% by weight of N-(1-acetyl-2,2,6,6-tetramethyl- piperidin-4-yl)-3-n-tetradecyl-tetrahydro-1 ,4-oxazin-2-one.
  • Red unscented candle wax is well stabilized by 0.1% by weight of 4,4'-dimethoxy-2,2'- dihydroxybenzophenone in combination with 0.1% by weight of 3,3,4-trimethyl-5-ethyl-5- hydroxymethyl-2-morpholinone.
  • Example 114
  • Yellow unscented candle wax is well stabilized by 0.2% by weight of 2-ethoxy-2-ethyloxanilide in combination with 0.1% by weight of 3,3-diethyl-5,5-dimethyl-4-hydroxy-2-morpholinone.
  • Yellow unscented candle wax is well stabilized by 0.2% by weight of 3-hydroxyphenyl benzoate in combination with 0.2% by weight of 3,3,5,5-tetramethyl-4-( ⁇ -methylbenzyl)-2-morpholinone.
  • Yellow scented candle wax is well stabilized by 0.1% by weight of 2-[2-hydroxy-3-( ⁇ , ⁇ -dimethyi- benzyl)-5-tert-octylphenyl]-2H-benzotriazole, TINUVIN® 928, CIBA, in combination with 0.2% by weight of bis(3,3,4,5-tetramethyl2-morpholinon-5-ylmethyl) terephthalate.
  • Example 121 2-[2-hydroxy-3-( ⁇ , ⁇ -dimethyi- benzyl)-5-tert-octylphenyl]-2H-benzotriazole, TINUVIN® 928, CIBA, in combination with 0.2% by weight of bis(3,3,4,5-tetramethyl2-morpholinon-5-ylmethyl) terephthalate.
  • Red scented candle wax is well stabilized by 0.1% by weight of 5-chloro-2-(2-hydroxy-3-tert- butyl-5-methylphenyl)-2H-benzotriazole, TINUVIN® 326, CIBA, in combination with 0.1% by weight of 5-hydroxymethyl-3,3,5-trimethyl-2-morpholinone.
  • Green scented candle wax is well stabilized by 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5- tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA, in combination with 0.1 % by weight of 5-dodecanoyloxymethyl-3,3,5-trimethyl-2-morpholinone.
  • Green scented candle wax is well stabilized by 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5- tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA, in combination with 0.1 % by weight of 3,3,5,5-tetramethyl-4-oxyl-2-morpholinone.
  • Blue scented candle wax is well stabilized by 0.1% by weight of 2-(2-hydroxy-5-tert-octyiphenyl-
  • Blue scented candle wax is well stabilized by 0.2% by weight of 4-octyloxy-2-hydroxybenzo- phenone in combination with 0.1% by weight of 5,5'-bis(decandioyloxymethyl-3,3,5-trimethyl-2- morpholinone).
  • Red unscented candle wax is well stabilized by 0.2% by weight of 2-ethylhexyl p-methoxy- cinnamate in combination with 0.1% by weight of N-(2,2,6,6-tetramethylpiperidin-4-yl)- tetrahydro-1 ,4-oxazin-2-one.
  • Yellow unscented candle wax is well stabilized by 0.1 % by weight of 2-ethoxy-2'-ethyl-5,4'-di- tert-butyloxanilide in combination with 0.1% by weight of N-(1-acetyl-2,2,6,6-tetramethyl- piperidin-4-yl)-3-n-tetradecyl-tetrahydro-1 ,4-oxazin-2-one.
  • Yellow unscented candle wax is well stabilized by 0.1% by weight of 2,4-bis(2,4-dimethyl- phenyl)-6-[2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine, TINUVIN® 400, CIBA, in combination with 0.1% by weight of 3,3-pentamethylene-5,5-dimethyl-2-morpholinone.
  • Blue scented candle wax is well stabilized by 0.1% by weight of 2,4-bis(2,4-dimethylphenyl)-6- [2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)-5- ⁇ -cumylphenyl]-s-triazine in combination with 0.1% by weight of 3,3,4-trimethyl-5-ethyl-5-hydroxymethyl-2-morpholinone.
  • Blue unscented candle wax is well stabilized by 0.2% by weight of 2,4-bis(2,4-dimethylphenyl)- 6-(2-hydroxy-4-octyloxyphenyl)-s-triazine in combination with 0.1% by weight of 1-acetyl- 2,2,6,6-tetramethyl-4,4-(1-oxa-2,4-dioxo-3-dodecyliminotetramethylene)piperidine, TINUVIN® 440, CIBA, and 0.1% by weight of 3,3,5,5-tetramethyl-4-oxyl-2-morpholinone.
  • White unscented candle wax is well stabilized by 0.1% by weight of 3-hydroxyphenyl benzoate in combination with 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydro- cinnamate, TINUVIN® 384, CIBA, and 0.1% by weight of 3,3,5,5-tetramethyl-4-( ⁇ -methyl- benzyl)-2-morpholinone.
  • Yellow scented candle wax is well stabilized by 0.1% by weight of dodecyl 3,3-diphenyl- ⁇ - cyanoacrylate in combination with 0.1% by weight of 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy- 4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine, TINUVIN® 400, CIBA, and 0.1% by weight of 3,3,5,5-tetramethyl-4-( ⁇ -methylbenzyloxy)-2-morpholinone.
  • Yellow scented candle wax is well stabilized by 0.1% by weight of pentaerythrityl tetrakis[3,3- diphenyl- ⁇ -cyanoacrylate] in combination with 0.2% by weight of N-(2-hydroxyethyl)-3,3,5,5- tetramethyl-2-morpholinone.
  • Example 201 3,3-Dimethyl-1 -oxa-4-azaspiro[4.5]decane.
  • Example 202 2,2,4,4-Tetra ⁇ methyl-1 ,3-oxazolidine.
  • A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
  • C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
  • D is bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA.
  • E is 2-(2-hydroxy-3- -cumyl-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 928, CIBA.
  • H is 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy-4-(3-octyl/nonyl/decyloxy-2-hydroxypropoxy)-5- ⁇ - cumylphenyl]-s-triazine.
  • ⁇ E values represent the change in color after the indicated days of exposure. A low ⁇ E value indicates less change in color and is highly desired.
  • A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
  • B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
  • D is bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA.
  • E is the reaction product of 2,4,6-tris(2,4-dihydroxyphenyl)-s-triazine with octyl ⁇ -haloacetate.
  • F is 3,3-dimethyl-1-oxa-4-azaspiro[4.5]decane, the compound of instant Example 201.
  • G is 2,2,4,4-tetramethyl-1 ,3-oxazolidine, the compound of instant Example 202.
  • H is 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy-4-(3-octyl/nonyl/decyloxy-2-hydroxypropoxy)-5- ⁇ - cumylphenyl]-s-triazine.
  • Example 206 Color Fade of Gray Scented Candle Wax under Fluorescent Lamp Exposure.
  • a variety of different stabilizers are evaluated in gray scented candle wax obtained from the Candle-Lite Corporation under fluorescent lamp exposure.
  • the ⁇ E values represent the change in color after the indicated days of exposure. A low ⁇ E value indicates less change in color and is highly desired.
  • B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
  • C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
  • F is 3,3-dimethyl-1-oxa-4-azaspiro[4.5]decane, the compound of instant Example 201.
  • H is 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy-4-(3-octyl/nonyl/decyloxy-2-hydroxypropoxy)-5- ⁇ - cumylphenyl]-s-triazine.
  • Example 207 Color Fade of Gray Scented Candle Wax under UV Lamp Exposure.
  • a variety of different stabilizers are evaluated in gray scented candle wax obtained from the Candle-Lite Corporation under fluorescent lamp exposure.
  • the ⁇ E values represent the change in color after the indicated days of exposure. A low ⁇ E value indicates less change in color and is highly desired.
  • B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
  • C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
  • E is 2-(2-hydroxy-3- ⁇ -cumyl-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 928, CIBA.
  • G is 2,2,4,4-tetramethyl-1 ,3-oxazolidine, the compound of instant Example 202.
  • Green scented candle wax is well stabilized by 0.2% by weight of dimethyl p-methoxybenzylidenemalonate, SANDUVOR® PR 25, in combination with 0.2% by weight of 3,3- dimethyl-1 -oxa-4-azaspiro[4.5]decane.
  • Yellow scented candle wax is well stabilized by 0.1% by weight of di(1 ,2,2,6,6-pentamethyl- piperidin-4-yl) p-methoxybenzylidenemalonate, SANDUVOR® PR 31 , in combination with 0.1% by weight of 2,2,4,4-tetramethyl-1 ,3-oxazolidine.
  • Red unscented candle wax is well stabilized by 0.1% by weight of dimethyl di(p-chlorophenyl)- methylenemalonate in combination with 0.1% by weight of 2,2,11 ,11 -tetramethyl-3,9-dioxa- dispiro(4.2.4.2]tetradecane.
  • Red unscented candle wax is well stabilized by 0.2% by weight of dimethyl di(p-methoxy- phenyl)methylenemalonate in combination with 0.2% by weight of 3,3-dimethyl-1-oxa-4-oxyi-4- azaspiro[4.5]decane.
  • Red unscented candle wax is well stabilized by 0.2% by weight of 4-tert-butylphenyl 2-hydroxy- benzoate in combination with 0.1% by weight of 3,3-dimethyloI-1-oxa-4-azaspiro[4.5]decane.
  • Yellow unscented candle wax is well stabilized by 0.2% by weight of 2-ethoxy-2-ethyloxanilide in combination with 0.1% by weight of 2,3,3-trimethyl-1-oxa-4-azaspiro[4.5]decane.
  • Example 215 is
  • Blue unscented candle wax is well stabilized by 0.2% by weight of dodecyl 3-phenyl-3-methyl- ⁇ - cyanoacrylate in combination with 0.1% by weight of 4-ethyl-2-isopropyloxazolidine.
  • Blue unscented candle wax is well stabilized by 0.2% by weight of dodecyl 3,3-diphenyl- ⁇ - cyanoacrylate in combination with 0.2% by weight of 1 -aza-3,7-dioxa-2,8-diisopropyl-5-ethyl- bicyclo[3.3.0]octane.
  • Yellow scented candle wax is well stabilized by 0.2% by weight of 2- ⁇ 2-hydroxy-3-tert-butyl-5-[2- (omega-hydroxy-octa(ethyleneoxy)carbonyl)ethyl]phenyl ⁇ -2H-benzotriazole, TINUVIN® 1130, CIBA, in combination with 2% by weight of 3-acetyl-4,4-dimethyl-2-(3-amyl)oxazolidine.
  • Yellow scented candle wax is well stabilized by 0.1% by weight of 2-[2-hydroxy-3-( ⁇ , ⁇ -dimethyl- benzyl)-5-tert-octylphenyl]-2H-benzotriazole, TINUVIN® 928, CIBA, in combination with 0.2% by weight of 3-acetyl-4-ethyl-2-phenyloxazolidine.
  • Red scented candle wax is well stabilized by 0.1% by weight of 5-chloro-2-(2-hydroxy-3-tert- butyl-5-methylphenyl)-2H-benzothazole, TINUVIN® 326, CIBA, in combination with 0.1% by weight of N-(2-hydroxyethyl)-2,2'-diethyl-4,4'-dimethyl-1 ,3-oxazolidine.
  • Green scented candle wax is well stabilized by 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5- tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA, in combination with 0.1 % by weight of 1-aza-3,7-dioxa-2,8-diphenyl-5-methylolbicyclo[3.3.0]octane.
  • Example 222
  • Blue scented candle wax is well stabilized by 0.1% by weight of 2-(2-hydroxy-5-tert-octylphenyl-
  • Red unscented candle wax is well stabilized by 0.2% by weight of 2-ethylhexyl p-methoxy- cinnamate in combination with 0.1% by weight of 2,2,4,4-tetramethyl-1 ,3-oxazolidine.
  • Red unscented candle wax is well stabilized by 0.1% by weight of 4,4'-dimethoxy-2,2'dihydroxy- benzophenone in combination with 0.1% by weight of 1-aza-3,7-dioxa-2,8-di-n-propyl-5- methylolbicyclo[3.3.0]octane.
  • Yellow unscented candle wax is well stabilized by 0.1% by weight of 2-ethoxy-2'-ethyl-5,4'-di- tert-butyloxanilide in combination with 0.1% by weight of 2,2,11 ,11 -tetramethyl-3, 9-dioxa- dispiro(4.2.4.2]tetradecane.
  • Yellow unscented candle wax is well stabilized by 0.1% by weight of 2,4-bis(2,4-dimethyl- phenyl)-6-[2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine, TINUVIN® 400, CIBA, in combination with 0.1% by weight of 3-acetyl-4,4-dimethyl-2-(3-amyl)oxazolidine.
  • Example 229 :
  • Blue scented candle wax is well stabilized by 0.1% by weight of 2,4-bis(2,4-dimethylphenyl)-6- [2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)-5- ⁇ -cumylphenyl]-s-triazine in combination with 0.1% by weight of 4-ethyI-2-isopropyloxazolidine.
  • Blue unscented candle wax is well stabilized by 0.1% by weight of 2,4-bis(2,4-dimethylphenyl)- 6-[2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine, TINUVIN® 400, CIBA, in combination with 0.1% by weight of bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA, and 0.1% by weight of 2,2,4,4-tetramethyl-1 ,3-oxazolidine.
  • White unscented candle wax is well stabilized by 0.1% by weight of 4-tert-octylphenyl2-hydroxy- benzoate in combination with 2% by weight of 2,2,11 ,11-tetramethyl-3,9-dioxa-dispiro(4.2.4.2]- tetradecane.
  • White unscented candle wax is well stabilized by 0.1 % by weight of 3-hydroxyphenyl benzoate in combination with 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydro- cinnamate, TINUVIN® 384, CIBA, and 0.1% by weight of 3,3-di ⁇ methyl-1-oxa-4-hydroxy-4- azaspiro[4.5]decane.
  • Yellow scented candle wax is well stabilized by 0.1 % by weight of dodecyl 3,3-diphenyl- ⁇ - cyanoacrylate in combination with 0.1% by weight of 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy- 4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine, TINUVIN® 400, CIBA, and 0.1 % by weight of 2,2,4,4-tetramethyl-1 ,3-oxazolidine.
  • Yellow scented candle wax is well stabilized by 0.1% by weight of pentaerythrityl tetrakis[3,3- diphenyl- ⁇ -cyanoacrylate] in combination with 0.2% by weight of 3-acetyl-4-ethyl-2-phenyl- oxazolidine.
  • Red scented candle wax is well stabilized by 0.2% by weight of octyl 3-(p-methoxyphenyl)-3- phenyl- ⁇ -cyanoacrylate in combination with 0.2% by weight of 1-aza-3,7-dioxa-2,8-diphenyl-5- methylolbicyclo[3.3.0]octane.
  • Example 301 2.2-Pentamethvlene-5,5-pentamethvlene-imidazolidin-4-one.
  • Example 302 Color Fade of White Scented Candle Wax under Fluorescent Lamp Exposure.
  • a variety of different stabilizers are evaluated in white scented candle wax obtained from the Candle-Lite Corporation under fluorescent lamp exposure.
  • the ⁇ E values represent the change in color after the indicated days of exposure. A low ⁇ E value indicates less change in color and is highly desired.
  • A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
  • B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
  • C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
  • D is bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA.
  • E is the reaction product of 2,4,6-tris(2,4-dihydroxyphenyl)-s-triazine with octyl ⁇ -haloacetate.
  • F is 2,2-pentamethylene-5,5-pentamethylene-imidazolidin-4-one, the compound of instant
  • Example 303 Color Fade of White Scented Candle Wax under UV Lamp Exposure.
  • A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
  • B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
  • C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
  • D is bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA.
  • E is the reaction product of 2,4,6-tris(2,4-dihydroxyphenyl)-s-triazine with octyl ⁇ -haloacetate.
  • F is 2,2-pentamethylene-5,5-pentamethylene-imidazolidin-4-one, the compound of instant
  • Example 304 Color Fade of Gray Scented Candle Wax under Fluorescent Lamp Exposure.
  • a variety of different stabilizers are evaluated in gray scented candle wax obtained from the Candle-Lite Corporation under fluorescent lamp exposure.
  • the ⁇ E values represent the change in color after the indicated days of exposure. A low ⁇ E value indicates less change in color and is highly desired.
  • A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
  • B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
  • C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
  • F is 2,2-pentamethylene-5,5-pentamethylene-imidazolidin-4-one, the compound of instant
  • G is the mixture of 3,3;3,5;5,5-methylene-bis[2,4-bis(2,4-dimethylphenyl)]-6-[2-hydroxy-4-(3- butyloxy-2-hydroxypropoxyphenyl)]-s-triazine.
  • Green scented candle wax is well stabilized by 0.2% by weight of dimethyl p-methoxybenzylidenemalonate, SANDUVOR® PR 25, in combination with 0.2% by weight of 2,2-penta- methylene-5,5-pentamethylene-imidazolidin-4-one-1-oxyl.
  • Example 306 Yellow scented candle wax is well stabilized by 0.1% by weight of di(1 ,2,2,6,6-pentamethyl- piperidin-4-yl) p-methoxybenzylidenemalonate, SANDUVOR® PR 31 , in combination with 0.1% by weight of 2,2,5,5-tetramethyl-1-(2-hydroxyethyl)-imidazolin-4-one.
  • Red unscented candle wax is well stabilized by 0.1% by weight of dimethyl di(p-chlorophenyl)- methylenemalonate in combination with 0.1% by weight of 2,2,5,5-tetramethyl-4-oxoimidazoline-
  • Red unscented candle wax is well stabilized by 0.2% by weight of dimethyl di(p-methoxy- phenyl)methylenemalonate in combination with 0.2% by weight of bis-[2-(2,2,5,5-tetramethyl-4- oxo-imidazolin-1 -yl)ethyl] sebacate.
  • Red unscented candle wax is well stabilized by 0.1% by weight of 4,4'-dimethoxy-2,2'- dihydroxybenzophenone in combination with 0.1% by weight of 2,5-dimethyl-2,5-diisobutyl-4- oxoimidazoline-1 -oxyl.
  • Red unscented candle wax is well stabilized by 0.2% by weight of 4-tert-butylphenyl 2-hydroxy- benzoate in combination with 0.1% by weight of 2,2,5,5-tetramethyl-1-methyl-3-(2-hydroxy- ethyl)-imidazolin-4-one.
  • Yellow unscented candle wax is well stabilized by 0.2% by weight of 2-ethoxy-2-ethyloxanilide in combination with 0.1% by weight of (2,2,6,6-tetramethylpiperidine-1-oxyl)-4-spiro-2'-(4- oxoimidiazoline-1-oxyl)-5'-spiro-4-(2,2,6,6-tetramethylpiperidine-1-oxyl).
  • Yellow unscented candle wax is well stabilized by 0.2% by weight of 3-hydroxyphenyl benzoate in combination with 0.2% by weight of 2,2,5,5-tetramethyl-1-methyl-3-[H(OCH 2 CH 2 ) x ]-imidazolin- 4-one where x is 2 to 21 .
  • Blue unscented candle wax is well stabilized by 0.2% by weight of dodecyl 3-phenyl-3-methyl- ⁇ - cyanoacrylate in combination with 0.1% by weight of 2,5-dimethyl-2,5-diethyl-4-oxoimidazoline-
  • Blue unscented candle wax is well stabilized by 0.2% by weight of dodecyl 3,3-diphenyl- ⁇ - cyanoacrylate in combination with 0.2% by weight of the transesterification product of a 1 :1 methyl methacrylate:ethyl acrylate copolymer with 3-hydroxyethyl-2,2,5,5-tetramethylimidazo- lidin-4-one.
  • CIBA in combination with 2% by weight of the transesterification product of a 2:1 methyl methacrylate:ethyl acrylate copolymer with 3-hydroxyethyl-2,2,5,5-tetramethylimidazolidin-4- one.
  • Yellow scented candle wax is well stabilized by 0.1% by weight of 2-[2-hydroxy-3-( ⁇ , ⁇ -dimethyl- benzyl)-5-tert-octylphenyl]-2H-benzotriazole, TINUVIN® 928, CIBA, in combination with 0.2% by weight of 2,2-[(1 -methyl)-1 ,5-pentanediyl]-5,5-[(1 -methyl)-1 ,5-pentanediyl]-imidazolidin-4-one-1 - oxyl.
  • Red scented candle wax is well stabilized by 0.1% by weight of 5-chloro-2-(2-hydroxy-3-tert- butyl-5-methylphenyl)-2H-benzotriazole, TINUVIN® 326, CIBA, in combination with 0.1% by weight of 2,2,5,5-tetramethyl-1 -methyl-3-[heptadecylcarbonyl(OCH 2 CH 2 ) J-imidazolin-4-one where x is 2 to 21.
  • Green scented candle wax is well stabilized by 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5- tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA, in combination with 0.1% by weight of 2,2,5,5-tetramethyl-1 -methyl-3-[4-hydroxy-3,5-di-tert-butylbenzoyl(OCH 2 CH 2 ) x ]-imidazolin-4- one where x is 2 to 21.
  • Green scented candle wax is well stabilized by 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5- tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA, in combination with 0.1% by weight of 2,2,5,5-tetramethyl-1-methyl-3-[2-(heptadecylcarbonyloxyethyl]-imidazolin-4-one.
  • Blue scented candle wax is well stabilized by 0.1% by weight of 2-(2-hydroxy-5-tert-octylphenyl-
  • Blue scented candle wax is well stabilized by 0.2% by weight of 4-octyloxy-2-hydroxybenzo- phenone in combination with 0.1% by weight of 2,2-pentamethylene-5,5-pentamethylene- imidazolidin-4-one-1 -oxyl.
  • Red unscented candle wax is well stabilized by 0.2% by weight of 2-ethylhexyl p-methoxy- cinnamate in combination with 0.1% by weight of 2,2-pentamethylene-5,5-pentamethylene- imidazolidin-4-one.
  • Red unscented candle wax is well stabilized by 0.1% by weight of 4,4'-dimethoxy-2,2'dihydroxy- benzophenone in combination with 0.1% by weight of the transesterification product of a 1 :1 methyl methacrylate:ethyl acrylate copolymer with 3-hydroxyethyl-2,2,5,5-tetramethylimidazo- lidin-4-one.
  • Yellow unscented candle wax is well stabilized by 0.1% by weight of 2-ethoxy-2'-ethyl-5,4'-di- tert-butyloxanilide in combination with 0.1% by weight of 2,2-pentamethylene-5,5-penta- methylene-imidazolidin-4-one.
  • Example 325
  • Yellow unscented candle wax is well stabilized by 0.1 % by weight of 2,4-bis(2,4-dimethyl- phenyl)-6-[2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine, TINUVIN® 400,
  • CIBA in combination with 0.1% by weight of the transesterification product of a 2:1 methyl methacryiate:ethyl acrylate copolymer with 3-hydroxyethyl-2,2,5,5-tetramethylimidazolidin-4- one.
  • Blue scented candle wax is well stabilized by 0.1% by weight of 2,4-bis(2,4-dimethylphenyl)-6-
  • Blue unscented candle wax is well stabilized by 0.1% by weight of 2,4-bis(2,4-dimethylphenyl)- 6-[2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyI]-s-triazine, TINUVIN® 400, CIBA, in combination with 0.1% by weight of bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, Ciba, and 0.1% by weight of 2,2,5,5-tetramethyl-1-methyl-3-[4-hydroxy-3,5-di- tert-butylbenzoy OCH ⁇ H ⁇ J-imidazolin ⁇ -one where x is 2 to 21.
  • White unscented candle wax is well stabilized by 0.1% by weight of 4-tert-octylphenyl2-hydroxy- benzoate in combination with 2% by weight of 2,2,5,5-tetramethyl-4-oxoimidazo!ine-1-oxyl.
  • Example 330 White unscented candle wax is well stabilized by 0.1 % by weight of 3-hydroxyphenyl benzoate in combination with 0.1 % by weight of octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydro- cinnamate, TINUVIN® 384, CIBA, and 0.1% by weight of 2,2,5,5-tetramethyl-1-methyl-3-[2- (heptadecylcarbonyloxyethyl]-imidazolin-4-one.
  • Yellow scented candle wax is well stabilized by 0.1% by weight of dodecyl 3,3-diphenyl- ⁇ - cyanoacrylate in combination with 0.1% by weight of 2,4-bis(2,4-dimethylphenyi)-6-[2-hydroxy-
  • Yellow scented candle wax is well stabilized by 0.1% by weight of pentaerythrityl tetrakis[3,3- diphenyl- ⁇ -cyanoacrylate] in combination with 0.2% by weight of bis-[2-(2,2,5,5-tetramethyl-4- oxo-imidazolin-1 -yl)ethyl] sebacate.
  • Red scented candle wax is well stabilized by 0.2% by weight of octyl 3-(p-methoxyphenyl)-3- phenyl- ⁇ -cyanoacrylate in combination with 0.2% by weight of 2,2-pentamethylene-5,5-penta- methylene-imidazolidin-4-one.
  • Example 401 4-(3.5-Dimethvl-4-hvdroxvbenzyl)-2.2.6.6-tetramethvl-3,5-diketopiperazine. This compound is prepared according to the procedure of Example 5e of United States Patent No. 3,969,316.
  • Example 402 15-n-Octadecyl-7,15-diazadispiro[5,1 ,5,3]hexadecane-14,16-dione.
  • Example 403 Color Fade of Pink Scented Candle Wax under Fluorescent Lamp Exposure.
  • a variety of different stabilizers are evaluated in pink scented candle wax obtained from the Candle-Lite Corporation under fluorescent lamp exposure.
  • the ⁇ E values represent the change in color after the indicated days of exposure. A low ⁇ E value indicates less change in color and is highly desired.
  • A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
  • B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
  • C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
  • D is bis(1-octyloxy-2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 123, CIBA.
  • E is 2-(2,4-dibutyloxyphenyl)-4,6-bis(2-hydroxy-4-butyloxyphenyl)-s-triazine.
  • F is 4-(3,5-dimethyl-4-hydroxybenzyl)-2,2,6,6-tetramethyl-3,5-diketopiperazine, the compound of
  • ⁇ E values represent the change in color after the indicated days of exposure. A low ⁇ E value indicates less change in color and is highly desired.
  • A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
  • B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
  • C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
  • E is 2-(2,4-dibutyloxyphenyl)-4,6-bis(2-hydroxy-4-butyloxyphenyl)-s-triazine.
  • F is 4-(3,5-dimethyl-4-hydroxybenzyl)-2,2,6,6-tetramethyl-3,5-diketopiperazine, the compound of
  • G is bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA.
  • H is 5-trifluoromethyl-2-(2-hydroxy-3- ⁇ -cumyl-5-tert-octylphenyl)-2H-benzotriazole.
  • I is C 20 -C 40 alkyl 3-(5-chloro-2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate.
  • Example 405 Color Fade of Gray Scented Candle Wax under UV Lamp Exposure.
  • ⁇ E values represent the change in color after the indicated days of exposure. A low ⁇ E value indicates less change in color and is highly desired.
  • A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
  • B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
  • C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
  • D is bis(1-octyloxy-2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 123, CIBA.
  • E is 2-(2,4-dibutyloxyphenyl)-4,6-bis(2-hydroxy-4-butyloxyphenyl)-s-triazine.
  • F is 4-(3,5-dimethyl-4-hydroxybenzyl)-2,2,6,6-tetramethyl-3,5-diketopiperazine, the compound of
  • H is 5-trifluoromethyl-2-(2-hydroxy-3- ⁇ -cumyl-5-tert-octylphenyl)-2H-benzotriazole.
  • Example 406 Color Fade of White Scented Candle Wax under Fluorescent Lamp Exposure.
  • a variety of different stabilizers are evaluated in white scented candle wax obtained from the Candle-Lite Corporation under fluorescent lamp exposure.
  • the ⁇ E values represent the change in color after the indicated days of exposure. A low ⁇ E value indicates less change in color and is highly desired.
  • A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
  • B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
  • C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
  • E is 2-(2,4-dibutyloxyphenyl)-4,6-bis(2-hydroxy-4-butyloxyphenyl)-s-triazine.
  • F is 4-(3,5-dimethyl-4-hydroxybenzyl)-2,2,6,6-tetramethyl-3,5-diketopiperazine, the compound of
  • G is bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA.
  • H is 5-trifluoromethyl-2-(2-hydroxy-3- ⁇ -cumyl-5-tert-octylphenyl)-2H-benzotriazole.
  • Example 407 Color Fade of White Scented Candle Wax under UV Lamp Exposure.
  • ⁇ E values represent the change in color after the indicated days of exposure. A low ⁇ E value indicates less change in color and is highly desired.
  • A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
  • B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
  • C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
  • E is 2-(2,4-dibutyloxyphenyl)-4,6-bis(2-hydroxy-4-butyloxyphenyl)-s-triazine.
  • F is 4-(3,5-dimethyl-4-hydroxybenzyl)-2,2,6,6-tetramethyl-3,5-diketopiperazine, the compound of
  • G is bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA.
  • H is 5-trifluoromethyl-2-(2-hydroxy-3- ⁇ -cumyl-5-tert-octylphenyl)-2H-benzotriazole.
  • I is the reaction product of 2,4,6-tris(2,4-dihydroxyphenyl)-s-triazine with octyl ⁇ -haloacetate.
  • J is 15-n-octadecyl-7, 15-diazadispiro[5, 1 ,5,3]hexadecane-14, 16-dione.
  • Example 408 Green scented candle wax is well stabilized by 0.2% by weight of dimethyl p-methoxybenzylidenemalonate, SANDUVOR® PR 25, in combination with 0.2% by weight of 15-benzyl- 7,15-diazadispiro[5.1.5.3]hexadecane-14,16-dione.
  • Yellow scented candle wax is well stabilized by 0.1% by weight of di(1 ,2,2,6,6-pentamethyl- piperidin-4-yl) p-methoxybenzylidenemalonate, SANDUVOR® PR 31 , in combination with 0.1% by weight of 4-n-octadecyl-2,2,6,6-tetramethyl-3,5-diketopiperazine.
  • Red unscented candle wax is well stabilized by 0.1% by weight of dimethyl di(p-chlorophenyl)- methylenemalonate in combination with 0.1% by weight of 4,4'-n-octamethylene-bis(2,2,6,6- tetramethyl-3,5-diketopiperazine.
  • Red unscented candle wax is well stabilized by 0.2% by weight of dimethyl di(p-methoxy- phenyl)methylenemalonate in combination with 0.2% by weight of 15-n-octadecyl-1 ,9-dimethyl-
  • Red unscented candle wax is well stabilized by 0.1% by weight of 4,4'-dimethoxy-2,2'- dihydroxybenzophenone in combination with 0.1% by weight of 3,3,5,5-tetramethyl-4-octyloxy-1-
  • Red unscented candle wax is well stabilized by 0.2% by weight of 4-tert-butylphenyl 2-hydroxy- benzoate in combination with 0.1% by weight of 3,3,5,5-tetramethyl-4-acetyl-1-(4-hydroxy-3,5- ditert-butylbenzylpiperazin-2,6-dione.
  • Yellow unscented candle wax is well stabilized by 0.2% by weight of 2-ethoxy-2-ethyloxanilide in combination with 0.1% by weight of tetramethylene bis[4-(3,3,4,5,5-pentamethylpiperazin-2,6- dione-1-yl)butyrate].
  • Example 415
  • Yellow unscented candle wax is well stabilized by 0.2% by weight of 3-hydroxyphenyl benzoate in combination with 0.2% by weight of 3,3,5,5-tetramethyl-4-hydroxy-1-octylpiperazin-2,6-dione.
  • Blue unscented candle wax is well stabilized by 0.2% by weight of dodecyl 3-phenyl-3-methyl- ⁇ - cyanoacrylate in combination with 0.1 % by weight of 1 ,3,3,5,5-pentamethyl-4-oxylpiperazin-2,6- dione.
  • Blue unscented candle wax is well stabilized by 0.2% by weight of dodecyl 3,3-diphenyl- ⁇ - cyanoacrylate in combination with 0.2% by weight of 3,3,4,5,5-pentamethyl-1-(ethoxycarbonyl- methyl)-piperazin-2,6-dione.
  • Yellow scented candle wax is well stabilized by 0.1% by weight of 2-[2-hydroxy-3-( ⁇ , ⁇ -dimethyl- benzyl)-5-tert-octylphenyl]-2H-benzotriazole, TINUVIN® 928, CIBA, in combination with 0.2% by weight of 15-n-octadecyl-7,15-diazadispiro[5,1 ,5,3]hexadecane-14,16-dione.
  • Red scented candle wax is well stabilized by 0.1 % by weight of 5-chloro-2-(2-hydroxy-3-tert- butyl-5-methylphenyl)-2H-benzotriazole, TINUVIN® 326, CIBA, in combination with 0.1% by weight of 15-benzyl-7,15-diazadispiro[5.1.5.3]hexadecane-14,16-dione.
  • Example 421 Green scented candle wax is well stabilized by 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5- tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA, in combination with 0.1% by weight of 4-n-octadecyl-2,2,6,6-tetramethyl-3,5-diketopiperazine.
  • Green scented candle wax is well stabilized by 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5- tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA, in combination with 0.1 % by weight of 4,4'-n-octamethylene-bis(2,2,6,6-tetramethyl-3,5-diketopiperazine.
  • Blue scented candle wax is well stabilized by 0.1% by weight of 2-(2-hydroxy-5-tert-octyiphenyl-
  • Blue scented candle wax is well stabilized by 0.2% by weight of 4-octyloxy-2-hydroxybenzo- phenone in combination with 0.1% by weight of 3,3,5,5-tetramethyl-4-octyloxy-1-(4-hydroxy-3,5- ditert-butylbenzylpiperazin-2,6-dione.
  • Red unscented candle wax is well stabilized by 0.2% by weight of 2-ethylhexyl p-methoxy- cinnamate in combination with 0.1% by weight of 3,3,5,5-tetramethyl-4-acetyl-1-(4-hydroxy-3,5- ditert-butylbenzylpiperazin-2,6-dione.
  • Red unscented candle wax is well stabilized by 0.1% by weight of 4,4'-dimethoxy-2,2'dihydroxy- benzophenone in combination with 0.1 % by weight of tetramethylene bis[4-(3,3,4,5,5-penta- methylpiperazin-2,6-dione-1-yl)butyrate].
  • Yellow unscented candle wax is well stabilized by 0.1% by weight of 2-ethoxy-2'-ethyl-5,4'-di- tert-butyloxanilide in combination with 0.1% by weight of 3,3,5,5-tetramethyl-4-hydroxy-1-octyl- piperazin-2,6-dione.
  • Example 428
  • Yellow unscented candle wax is well stabilized by 0.1% by weight of 2,4-bis(2,4-dimethyl- phenyl)-6-[2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine, TINUVIN® 400, CIBA, in combination with 0.1% by weight of 1 ,3,3,5,5-pentamethyl-4-oxylpiperazin-2,6-dione.
  • Blue scented candle wax is well stabilized by 0.1 % by weight of 2,4-bis(2,4-dimethylphenyl)-6- [2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)-5- ⁇ -cumylphenyl]-s-triazine in combination with 0.1% by weight of 3,3,4,5,5-pentamethyl-1-(ethoxycarbonylmethyl)-piperazin-2,6-dione.
  • Blue unscented candle wax is well stabilized by 0.1 % by weight of 2,4-bis(2,4-dimethylphenyl)- 6-[2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine, TINUVIN® 400, CIBA, in combination with 0.1% by weight of bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA, and 0.1% by weight of 15-n-octadecyl-7,15-diazadispiro[5,1 ,5,3]hexa- decane-14,16-dione.
  • White unscented candle wax is well stabilized by 0.1 % by weight of 4-tert-octylphenyl2-hydroxy- benzoate in combination with 2% by weight of 15-benzyl-7,15-diazadispiro[5.1.5.3]hexadecane- 14,16-dione;
  • White unscented candle wax is well stabilized by 0.1 % by weight of 3-hydroxyphenyl benzoate in combination with 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydro- cinnamate, TINUVIN® 384, CIBA, and 0.1% by weight of 4-n-octadecyl-2,2,6,6-tetramethyl-3,5- diketopiperazine.
  • Yellow scented candle wax is well stabilized by 0.1% by weight of dodecyl 3,3-diphenyl- ⁇ - cyanoacrylate in combination with 0.1% by weight of 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy- 4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine, TINUVIN® 400, CIBA, and 0.1% by weight of 4,4'-n-octamethylene-bis(2,2,6,6-tetramethyl-3,5-diketopiperazine.
  • Yellow scented candle wax is well stabilized by 0.1% by weight of pentaerythrityl tetrakis[3,3- diphenyl- ⁇ -cyanoacrylate] in combination with 0.2% by weight of 15-n-octadecyl-1 ,9-dimethyl- 7,15-diazadispiro[5.1.5.3]hexadecane-14,16-dione.
  • Red scented candle wax is well stabilized by 0.2% by weight of octyl 3-(p-methoxyphenyl)-3- phenyl- ⁇ -cyanoacrylate in combination with 0.2% by weight of 3,3,5,5-tetramethyl-4-octyloxy-1-
  • Example 501 1 ,3,5-tris ⁇ N-cyclohexyl-N-[2-(2,2,6,6-tetramethyl-piperazin-3-on-4-yl)ethyl]amino ⁇ - s-triazine.
  • This compound is a commercial stabilizer GOODRITE® 3150, obtained from the Goodrite Corporation and is made by the general procedures given in United States Patent No. 4,547,538.
  • Example 502 1 ,3,5-tris ⁇ N-cyclohexyl-N-[2-(1 ,2,2,6,6-pentamethylpiperazin-3-on-4-yl)ethyl] amino ⁇ -s-triazine.
  • This compound is a commercial stabilizer GOODRITE® 3159, obtained from the Goodrite Corporation and is made by the general procedures given in United States Patent No. 4,547,538.
  • Example 503 1,2-ethane-bis(3,3,5,5-tetramethylpiperazin-2-on-1-vl).
  • This compound is a commercial stabilizer GOODRITE® 3034, obtained from the Goodrite Corporation and is made by the general procedures given in United States Patent No. 4,547,538.
  • Example 504 Color Fade of Pink Scented Candle Wax under Fluorescent Lamp Exposure.
  • a variety of different stabilizers are evaluated in pink scented candle wax obtained from the Candle-Lite Corporation under fluorescent lamp exposure.
  • the ⁇ E values represent the change in color after the indicated days of exposure. A low ⁇ E value indicates less change in color and is highly desired.
  • A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
  • B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazoIe, TINUVIN® 329, CIBA.
  • C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
  • D is bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA.
  • E is 2,4-bis(2,4-dimethylphenyl)-6-(2-hydroxy-4-octyloxyphenyl)-s-triazine, UV 1164, CYTEC.
  • F is ethyl 2-cyano-3,3-diphenylacrylate, UVINUL® N-35, BASF.
  • G is 1 ,3,5-tris ⁇ N-cyclohexyl-N-[2-(2,2,6,6-tetramethylpiperazin-3-on-4-yl)ethyl]amino ⁇ -s-triazine,
  • H is 1 ,2-ethane-bis(3,3,5,5-tetramethylpiperazin-2-on-1-yl), GOODRITE® 3034, GOODRITE, the compound of Example 503.
  • Example 505 Color Fade of Pink Scented Candle Wax under UV Lamp Exposure.
  • ⁇ E values represent the change in color after the indicated days of exposure. A low ⁇ E value indicates less change in color and is highly desired.
  • A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
  • B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
  • C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
  • D is bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA.
  • E is 2,4-bis(2,4-dimethylphenyl)-6-(2-hydroxy-4-octyloxyphenyl)-s-triazine, UV 1164, CYTEC.
  • G is 1 ,3,5-tris ⁇ N-cyclohexyl-N-[2-(2,2,6,6-tetramethylpiperazin-3-on-4-yl)ethyl]amino ⁇ -s-triazine,
  • H is 1 ,2-ethane-bis(3,3,5,5-tetramethyipiperazin-2-on-1-yl), GOODRITE® 3034, GOODRITE, the compound of Example 503.
  • Example 506 Color Fade of Gray Scented Candle Wax under Fluorescent Lamp Exposure.
  • a variety of different stabilizers are evaluated in gray scented candle wax obtained from the Candle-Lite Corporation under fluorescent lamp exposure.
  • the ⁇ E values represent the change in color after the indicated days of exposure. A low ⁇ E value indicates less change in color and is highly desired.
  • A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
  • B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
  • C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
  • H is 1 ,2-ethane-bis(3,3,5,5-tetramethylpiperazin-2-on-1-yl), GOODRITE® 3034, GOODRITE, the compound of Example 503.
  • I is bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, TINUVIN® 123, CIBA.
  • Example 507 Color Fade of Gray Scented Candle Wax under UV Lamp Exposure.
  • ⁇ E values represent the change in color after the indicated days of exposure. A low ⁇ E value indicates less change in color and is highly desired.
  • A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
  • B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
  • C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
  • H is 1 ,2-ethane-bis(3,3,5,5-tetramethylpiperazin-2-on-1-yl), GOODRITE® 3034, GOODRITE, the compound of Example 503.
  • I is bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, TINUVIN® 123, CIBA.
  • Example 508 Color Fade of White Scented Candle Wax under Fluorescent Lamp Exposure.
  • a variety of different stabilizers are evaluated in white scented candle wax obtained from the Candle-Lite Corporation under fluorescent lamp exposure.
  • the ⁇ E values represent the change in color after the indicated days of exposure. A low ⁇ E value indicates less change in color and is highly desired.
  • A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
  • B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
  • C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
  • D is bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA.
  • E is 2,4-bis(2,4-dimethylphenyl)-6-(2-hydroxy-4-octyloxyphenyl)-s-triazine, UV 1164, CYTEC.
  • G is 1 ,3,5-tris ⁇ N-cyclohexyl-N-[2-(2,2,6,6-tetramethylpiperazin-3-on-4-yl)ethyl]amino ⁇ -s-triazine,
  • Green scented candle wax is well stabilized by 0.2% by weight of dimethyl p-methoxybenzylidenemalonate, SANDUVOR® PR 25, in combination with 0.2% by weight of 7-methyi- 7,15-diazadispiro[5.1.5.3]hexadecane-14-one.
  • Yellow scented candle wax is well stabilized by 0.1% by weight of di(1 ,2,2,6,6-pentamethyl- piperidin-4-yl) p-methoxybenzylidenemalonate, SANDUVOR® PR 31 , in combination with 0.1% by weight of 1 ,3,3,5,5-pentamethyl-4-(2-hydroxyethyl)-2-ketopiperazine.
  • SANDUVOR® PR 31 di(1 ,2,2,6,6-pentamethyl- piperidin-4-yl) p-methoxybenzylidenemalonate
  • SANDUVOR® PR 31 0.1% by weight of 1 ,3,3,5,5-pentamethyl-4-(2-hydroxyethyl)-2-ketopiperazine.
  • Example 511 Example 511 :
  • Red unscented candle wax is well stabilized by 0.1% by weight of dimethyl di(p-chlorophenyl)- methylenemalonate in combination with 0.1% by weight of 3,3,5,5-tetramethyl-4-octyloxy-1- octyl-2-ketopiperazine.
  • Red unscented candle wax is well stabilized by 0.2% by weight of dimethyl di(p-methoxy- phenyl)methylenemalonate in combination with 0.2% by weight of 1 ,3,3,5,5-pentamethyl-4-oxyl-
  • Red unscented candle wax is well stabilized by 0.1% by weight of 4,4'-dimethoxy-2,2'- dihydroxybenzophenone in combination with 0.1% by weight of 3,3,4,5,5-pentamethyl-1-(2- hydroxyethyl)piperazin-2-one.
  • Red unscented candle wax is well stabilized by 0.2% by weight of 4-tert-butylphenyl 2-hydroxy- benzoate in combination with 0.1% by weight of 3,3,5,5-tetramethyl-4-cyclohexyloxy-1-[2-(do- decanoyloxy)ethyl]piperazin-2-one.
  • Yellow unscented candle wax is well stabilized by 0.2% by weight of 2-ethoxy-2-ethyloxanilide in combination with 0.1% by weight of bis[2-(4-cyclohexyloxy-3,3,5,5-tetramethyl-2-ketopiperazin- 1 -yl)ethyl] sebacate.
  • Yellow unscented candle wax is well stabilized by 0.2% by weight of 3-hydroxyphenyl benzoate in combination with 0.2% by weight of 4-octyloxy-3,3,5,5-tetramethyl-1-octadecyipiperazin-2- one.
  • Blue unscented candle wax is well stabilized by 0.2% by weight of dodecyl 3-phenyl-3-methyl- ⁇ - cyanoacrylate in combination with 0.1% by weight of 1 ,3,5-tris ⁇ N-cyclohexyl-N-[2-(2,2,6,6-tetra- methylpiperazin-3-on-4-yl)ethyl]amino ⁇ -s-triazine.
  • Example 518 :
  • Blue unscented candle wax is well stabilized by 0.2% by weight of dodecyl 3,3-diphenyl- ⁇ - cyanoacrylate in combination with 0.2% by weight of 1 ,3,5-tris ⁇ N-cyclohexyl-N-[2-(1 ,2,2,6,6- pentamethylpiperazin-3-on-4-yl)ethyl]amino ⁇ -s-triazine.
  • Yellow scented candle wax is well stabilized by 0.2% by weight of 2- ⁇ 2-hydroxy-3-tert-butyl-5-[2- (omega-hydroxy-octa(ethyleneoxy)carbonyl)ethyl]phenyl ⁇ -2H-benzotriazole, TINUVIN® 1130, CIBA, in combination with 2% by weight of 1 ,2-ethane-bis(3,3,5,5-tetramethylpiperazin-2-on-1- yi).
  • Yellow scented candle wax is well stabilized by 0.1% by weight of 2-[2-hydroxy-3-( ⁇ , ⁇ -dimethyl- benzyl)-5-tert-octylphenyl]-2H-benzotriazole, TINUVIN® 928, CIBA, in combination with 0.2% by weight of 7-methyl-7,15-diazadispiro[5.1.5.3]hexadecane-14-one.
  • Red scented candle wax is well stabilized by 0.1% by weight of 2-(2-hydroxy-5-methylphenyl)-
  • Green scented candle wax is well stabilized by 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5- tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA, in combination with 0.1% by weight of 3,3,5,5-tetramethyl-4-octyloxy-1 -octyl-2-ketopiperazine.
  • Green scented candle wax is well stabilized by 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5- tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA, in combination with 0.1% by weight of 1 ,3,3,5,5-pentamethyl-4-oxyl-2-ketopiperazine.
  • Example 524 Blue scented candle wax is well stabilized by 0.1% by weight of 2-(2-hydroxy-5-tert-octylphenyl- 2H-benzotriazole, TINUVIN® 329, CIBA, in combination with 0.1 % by weight of 3,3,4,5, 5-penta- methyl-1-(2-hydroxyethyl)piperazin-2-one.
  • Blue scented candle wax is well stabilized by 0.2% by weight of 4-octyloxy-2-hydroxybenzo- phenone in combination with 0.1% by weight of 3,3,5,5-tetramethyl-4-cyclohexyloxy-1 -[2-(do- decanoyloxy)ethyl]piperazin-2-one.
  • Red unscented candle wax is well stabilized by 0.2% by weight of 2-ethylhexyl p-methoxy- cinnamate in combination with 0.1% by weight of bis[2-(4-cyclohexyloxy-3,3,5,5-tetramethyl-2- ketopiperazin-1 -yl)ethyl] sebacate.
  • Red unscented candle wax is well stabilized by 0.1% by weight of 4,4'-dimethoxy-2,2'dihydroxy- benzophenone in combination with 0.1% by weight of 4-octyloxy-3,3,5,5-tetramethyl-1- octadecylpiperazin-2-one.
  • Yellow unscented candle wax is well stabilized by 0.1% by weight of 2-ethoxy-2'-ethyl-5,4'-di- tert-butyloxanilide in combination with 0.1% by weight of 1 ,3,5-tris ⁇ N-cyclohexyl-N-[2-(2,2,6,6- tetramethylpiperazin-3-on-4-yl)ethyl]amino ⁇ -s-triazine.
  • Yellow unscented candle wax is well stabilized by 0.1% by weight of 2,4-bis(2,4-dimethyl- phenyl)-6-[2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine, TINUVIN® 400,
  • CIBA in combination with 0.1% by weight of 1 ,3,5-tris ⁇ N-cyclohexyl-N-[2-(1 ,2,2,6,6-penta- methylpiperazin-3-on-4-yl)ethyl]amino ⁇ -s-triazine.
  • Example 530 Blue scented candle wax is well stabilized by 0.1% by weight of 2,4-bis(2,4-dimethylphenyl)-6- [2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)-5- ⁇ -cumylphenyl]-s-triazine in combination with 0.1% by weight of 1 ,2-ethane-bis(3,3,5,5-tetramethylpiperazin-2-on-1-yl).
  • Blue unscented candle wax is well stabilized by 0.2% by weight of 2,4-bis(2,4-dimethylphenyl)- 6-(2-hydroxy-4-octyloxyphenyl)-s-triazine in combination with 0.1% by weight of 1-acetyl- 2,2,6,6-tetramethyl-4,4-(1 -oxa-2,4-dioxo-3-dodecyliminotetramethylene)piperidine, TINUVIN® 440, CIBA, and 0.1 % by weight of 7-methyl-7,15-diazadispiro[5.1.5.3]hexadecane-14-one.
  • TINUVIN® 292 CIBA
  • White unscented candle wax is well stabilized by 0.1% by weight of 4-tert-octylphenyl2-hydroxy- benzoate in combination with 2% by weight of 3,3,5,5-tetramethyl-4-octyloxy-1 -octyl-2-keto- piperazine.
  • White unscented candle wax is well stabilized by 0.1 % by weight of 3-hydroxyphenyl benzoate in combination with 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydro- cinnamate, TINUVIN® 384, CIBA, and 0.1% by weight of 1 ,3,3,5,5-pentamethyl-4-oxyl-2-keto- piperazine.
  • Yellow scented candle wax is well stabilized by 0.1% by weight of dodecyl 3,3-diphenyl- ⁇ - cyanoacrylate in combination with 0.1% by weight of 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy- 4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine, TINUVIN® 400, CIBA, and 0.1% by weight of 3,3,4,5,5-pentamethyl-1 -(2-hydroxyethyl)piperazin-2-one.
  • Example 536 Example 536:
  • Yellow scented candle wax is well stabilized by 0.1% by weight of pentaerythrityl tetrakis[3,3- diphenyl- ⁇ -cyanoacrylate] in combination with 0.2% by weight of 3,3,5,5-tetramethyl-4-cyclo- hexyloxy-1-[2-(dodecanoyloxy)ethyl]piperazin-2-one.
  • Red scented candle wax is well stabilized by 0.2% by weight of octyl 3-(p-methoxyphenyl)-3- phenyl- ⁇ -cyanoacrylate in combination with 0.2% by weight of bis[2-(4-cyclohexyloxy-3,3,5,5- tetramethyl-2-ketopiperazin-1 -yl)ethyl] sebacate.

Abstract

White, dyed, dipped, unscented and/or scented candle wax is effectively stabilized against discoloration and fading by the incorporation therein of a morpholinone, an oxazolidine, an imidazolidine, a piperazindione or a piperazinone, in combination with an UV absorber and/or an antioxidant.

Description

Stabilized candle wax
The instant invention pertains to white, dyed, dipped, unscented and/or scented candle wax which is effectively stabilized against discoloration and fading by the incorporation therein of a morpholinone, an oxazolidine, an imidazolidine, a piperazindione or a piperazinone, in combination with an UV absorber and/or an antioxidant.
Candles have been known for many centuries going back to the eighth century B.C. The nature of candles is described in Ullmann's Encyclopedia of Industrial Chemistry, Volume A5 at pages 29-30 where it is seen that candles are made from paraffin, beeswax and stearin as basic materials, and where a host of additives may also be present.
It is not surprising that with candles and wax becoming increasingly more important attention was paid as to how to stabilize the said materials. At the National Candle Association Meeting in Houston, 1994, R. van der Vennet presented a paper on "Antioxidants in Wax - Replacement of BHT" touting the use of Vitamin E (tocopherol) as an antioxidant to prevent the yellowing of wax when oxidized. WO 94/13736 describes the same invention.
EP 359,488 A3 and EP 133,964 B1 describe stabilized waxes used in cosmetics where the waxes are the same or similar to those used in candles.
EP 5,922 A1 describes lip cosmetics where the waxes are useful in lipsticks and are related to those useful in candles.
United States Patent No. 5,879,694 describes in detail transparent gel candles both in composition and structure. The use of BHT as an antioxidant is mentioned.
At the National Candle Association Technical Meeting on April 16, 1998, F. A. Ballentine et al., presented a paper entitled "Inhibiting Color Fading of Dyed Candles with CYASORB® Light Absorbers" in which the general theories of thermal oxidation and photodegradation are discussed along with data on the effect of light absorbers on color stability of dyed candle waxes. The light absorbers compared are 4-octyloxy-2-hydroxybenzophenone UV-531 ; 4- methoxy-2-hydroxybenzophenone UV-9; 2-(2-hydroxy-5-methylphenyl)-2H-benzotriazole UV- 5365; 2-(2-hydroxy-5-tert-octylphenyl-2H-benzotriazole UV-5411 and 2-(2-hydroxy-3,5-di-tert- amylphenyl)-2H-benzotriazole UV-2337).
United States Patent No. 5,964,905 teaches dyed and scented candle gels containing triblock copolymers and a hydrocarbon oil of high flash point. This reference teaches that a light (UV) absorber may be used to improve the shelf stability of the candle color when exposed to visible or ultraviolet light. Two preferred absorbers are ethylhexyl p-methoxycinnamate (PARSOL® MCX, Roche) and 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole (CYASORB® 5411 , Cytec).
WO 00/22037 teaches the stabilization of solid, shaped and colored wax articles, including candles, using a malonate UV absorber which may optionally contain a hindered amine moiety as part of the malonate compound structure. The wax articles are dyed with a variety of oil soluble dyes and pigments. The samples protected by dimethyl p-methoxybenzylidinemalonate exhibited better resistance to discoloration that did samples stabilized with selected benzotriazole or benzophenone UV absorbers.
Japanese Hei 3-278554 teaches that wax crayons (drawing materials) colored by organic pigments can be stabilized by a hindered amine and/or benzotriazole.
In respect to wax stabilization, the use of selected hindered amines and/or benzotriazole UV absorbers is also known in the prior art as seen in United States Patent Nos. 3,530,084; 4,379,721 ; 4,616,051 and 5,964,905.
United States Patent No. 4,547,537 teaches tetrahydro-1 ,4-oxazin-2-one moieties attached to a substituted piperidinyl hindered amine group as stabilizers for polyolefins and other polymeric substrates.
United States Patent Nos. 4,797,451 and 4,853,440 described paraffinic polymers such as polybutadiene or polyisoprene that have inter alia morpholinone moieties reacted into the polymer backbone. United States Patent Nos. 4,528,370; 4,914,232 and 5,089,614 describe morpholinone compounds which are useful as light stabilizers.
WO 98/44008 describes a controlled free radical polymerization process using inter alia selected morpholinone based nitroxide groups.
WO 00/39209 teaches polymeric stabilizers having low polydispersity and having inter alia pendant morpholinone groups.
WO 99/46261 describes nitroxyl derivatives with glycidyl or alkylcarbonyl groups as initiators for radical polymerization. Some such nitroxyl derivatives may also contain morpholinone groups.
German Offenlegunsschrift DE 198 45 298 A1 describes N-oxyl radicals of morpholinone derivatives useful in free radical polymerization.
British 2,342,649 A describes heterocyclic alkoxyamines as regulators in controlled free radical polymerization processes inter alia these include molecules which contain morpholinone moieties.
WO 99/14206 depicts morpholinone compounds as light stabilizers for organic material especially for coatings.
WO 00/14177 teaches the inhibition of vinyl monomer polymerization using hindered hydroxylamines some of which may contain an oxazolidine moiety. There is no suggestion that any of these compounds would be stabilizers for candle wax.
United States Patent Nos. 4,125,518 and 4,104,254 teach that 1-oxa-4-azaspiro[4.5]decanes and other oxazolidine molecules are useful light stabilizers for polyolefins such as polypropylene.
United States Patent Nos. 5,264,148 and 5,223,174 describe various mono- and bicyclic oxazolidine compounds which have the property of scavenging moisture particularly aimed at efficiently, cost effectively and safely removing water from moisture-curable polyurethane coating systems or any other water-sensitive system where residual water is a problem. United States Patent Nos. 3,707,541 and 3,825,555 describe the use of oxazolidine and tetrahydrooxazine compounds as insect repellents.
United States Patent Nos. 4,017,406, 4,116,643 and 4.369,118 describe oxazoline compounds and amine salts of carboxylate half esters of 1-aza-3,7-dioxabicyclo[3,3,0]oct-5-yl methyl alcohols as additives for lubricating oils, gasoline, middle distillate fuels and other oleaginous products.
United States Patent No. 5,001,233 teaches the synthesis of hydroxylamines using dioxiranes. Cyclic hydroxylamines having oxazolidine moieties present are disclosed.
United States Patent Nos. 5,328,635 and 5,433,891 disclose iminoalcohol-oxazolidine mixtures which are useful as corrosion inhibitors, moisture or formaldehyde scavengers, drying agents and the like.
WO 98/11181 describes substituted oxazolines, related to oxazolidines, which are antioxidants and antioxidant boosters capable of producing hydroperoxyl radicals.
WO 99/05108 teaches the inhibition of pulp or paper which contains lignin from yellowing by use inter alia of a substituted oxazolidine or a salt thereof.
Imidazolidines have been known as stabilizers for various substrates. British Patent No.
1 ,145,470 teaches the stabilization of polyolefins using alkylated 4-oxoimidazolidine-1 -oxides such as 2,2,5,5-tetramethyl-4-oxoimidazolidine-1-oxide.
United States Patent No. 4,448,969 discloses the use of cyclic ether or carbonate alkylation products of 2,2,5,5-tetramethylimidazolidin-4-one for the stabilization of synthetic polymers, particularly polyolefins.
United States Patent Nos. 4,804,717 and 4,895,901 teach that polymeric hindered amine light stabilizers are useful for the stabilization of olefin, styrene and acrylate polymers which contain a minor amount of a pendant moiety derived from 3-hydroxy-2,2,5,5-tetramethylimidazolidine-4- one. European Patent Specification 313,941 B1 describes the stabilization of photochromic dye compositions using 1 -oxyl-2,2,5,5-tetramethylimidazolidin-4-one.
United States Patent No. 6,020,491 teaches the use of monomeric and polymeric cyclic amine and N-halamine compounds as biocides and disinfectants for a host of substrates. Some of the structures include a substituted 2,2,5,5-tetramethylimidazolidine moiety in a pendant group.
WO 98/30601 describes a method of controlling polymer molecular weight and polymer structure by living free radical polymerization where nitroxide and alkoxyamine containing a 2,2,5,5-tetramethylimidazolidine moiety are employed.
WO 99/61396 teaches the method of stabilizing unsaturated organic polymers using a host of polymerization inhibitors based on the alkylated 2,2,5,5-tetramethylimidazolidine compounds.
United States Patent Nos. 3,899,491; 3,992,351 ; 4,007,156 and 4,007,157 teach piperazindione compounds and their conversion into corresponding piperazine derivatives as light stabilizers.
United States Patent Nos. 3,919,234 and 3,969,316 describe the generic synthesis of selected piperazindione componds as light stabilizers.
United States Patent Nos. 3,928,357; 4,051 ,137; 4,125,517 and 4,208,522 show the preparation of substituted piperazindione compounds as light stabilizers.
United States Patent Nos. 3,920,659 and 3,968,078 describe the preparation of substituted piperazindione ester compounds as light stabilizers.
United States Patent Nos. 4,590,231 ; 4,668,721 and 4,691 ,015 describe the stabilization of polyolefin compositions using various hydroxylamine compounds some of which contain a piperazindione moiety.
WO 98/44008 teaches controlled free radical polymerization processes using a stable free radical agent which is a piperazinone, piperazindione or morpholinone based nitroxide. United States Patent No. 3,936,456 describes substituted piperazinedione oxyl and hydroxylamine derivaties useful in stabilizing polyolefins.
United States Patent No. 4,413,096 depicts olefin copolymers having pendant hindered amine groups inter alia one containing a piperazindione moiety.
German Offenlegungsschrift DE 199 24 984 A1 describes compositions stabilized by a host of piperazindione derivatives.
British 2,333,774 A and WO 00/31069 describe a number of 2-oxopiperazinyl derivatives useful for the stabilization of organic materials especially polymers and photographic materials.
United States Patent Nos. 4,167,512 and 4,190,571 describe some 2-keto-1 ,4-diazacyclo- alkanes including piperazinones as light stabilizers.
United States Patent Nos. 4,547,538; 4,480,092; 5,026,848 and 5,071,981 teach various oxo- piperazinyl-triazines including oligomeric structures as light stabilizers.
United States Patent No. 4,240,961 describes the preparation of piperazinones.
United States Patent No. 6,117,995 depicts the preparation of sterically hindered amine ethers where the cyclic ring is inter alia a piperazinone. These compounds are useful as stabilizers.
United States Patent Nos. 4,033,928; 4,110,304 and 4,123,418 teach inter alia that selected piperazinones are useful in protecting epoxy resins and styrene polymers from degradation.
None of these references teach the superior performance provided when the morpholinone, the oxazolidine, the imidazolidine, the piperazindione or the piperazinone is used in conjunction with an UV absorber and/or antioxidant to stabilize candle wax.
In more detail, the instant invention pertains to a composition which comprises
(a) candle wax which is white and unscented; white and scented; dyed and unscented; dyed and scented; dipped and unscented; or dipped and scented, and
(b) a combination of (i) a compound selected from the group consisting of a morpholinone compound containing a moiety of generic formula 1-100,
an oxazolidine compound containing a moiety of generic formula I-200, II-200 or III-200,
an imidazolidine compound containing a moiety of generic formula I-300,
a piperazindione compound containing a moiety of generic formula I-400, and a piperazinone compound containing a moiety of formula 1-500;
and
(ii) an UV absorber or an antioxidant, or an UV absorber and an antioxidant, wherein the ratio by weight of (i) to (ii) is from 10:1 to 1 :10.
The morpholinone compound is preferably a compound of formula la-100 or lb-100
where
R10ι is hydrogen, alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms or cycloalkenyl of 5 to 12 carbon atoms;
R102 has the same meaning as R10ι; or R102 is also hydroxyalkyl of 1 to 8 carbon atoms; or R10ι and R102 together are tetramethylene, pentamethylene or pentamethylene substituted by methyl; R103 has the same meaning as R10ι;
Rι04 has the same meaning as Rι02; or R103 and R104 together are tetramethylene, pentamethylene or pentamethylene substituted by methyl;
R105 is hydrogen; alkyl of 1 to 18 carbon atoms; alkyl of 2 to 18 carbon atoms substituted by hydroxy, by phenyl or by both hydroxy and phenyl; oxyl; hydroxy; cyanoalkyl of 2 to 12 carbon atoms; cyanoalkoxy of 2 to 12 carbon atoms; alkoxy of 1 to 18 carbon atoms; cycloalkoxy of 5 to 12 carbon atoms; alkenyl of 3 to 8 carbon atoms; alkenyloxy of 3 to 8 carbon atoms; phenylaikyl of 7 to 12 carbon atoms; phenylaikyl of 7 to 12 carbon atoms substituted by hydroxy, by alkyl of 1 to 4 carbon atoms or by alkoxy of 1 to 4 carbon atoms, or by both said alkyl and said alkoxy; phenylalkoxy of 7 to 12 carbon atoms; alkanoyl of 2 to 8 carbon atoms; or a substituted 2,2,6,6- tetraalkylpiperidinyl moiety; when n10o is 1 ;
R106 is a straight or branched chain alkyl of 1 to 24 carbon atoms which is unsubstituted or substituted by one to six hydroxy or -ORι groups; or Rι06 is phenyl; when n100 is 2;
Rioβ is alkylene of 2 to 12 carbon atoms, o-phenylene, m-phenylene, p-phenylene or p-xylylene; and R10 is hydrogen or has the meaning of R10ι-
The oxazolidine compound is preferably a compound of formula la-200, lla-200 or llla-200
°205 where
R201, R202, R203 and R2o are independently alkyl of 1 to 8 carbon atoms, or R20ι and R202 together or R2o3 and R204 together are tetramethylene, pentamethylene or pentamethylene substituted by methyl;
R205 is hydrogen, oxyl, hydroxy, aralkyl of 7 to 15 carbon atoms, alkoxy of 1 to 24 carbon atoms, alkyl of 1 to 42 carbon atoms, said alkyl substituted by one or two hydroxy groups, said alkyl substituted by alkylcarbonyloxy of 2 to 18 carbon atoms, or said alkyl interrupted by one to twenty oxygen atoms and substituted by one hydroxy, by alkylcarbonyloxy of 2 to 18 carbon atoms or by 4-hydroxy-3,5-di-tert-butylbenzoyloxy; or R2os is -CO-CnH2π+1 where n is 1 to 17, and
R206 is alkyl of 1 to 8 carbon atoms, said alkyl substituted by one or two hydroxy groups, or is aryl of 6 to 10 carbon atoms.
The imidazoline compound is preferably a compound of formula la-300
'304 where
R301 and R302 are independently alkyl of 1 to 8 carbon atoms, or R30ι and R302 together are tetramethylene, pentamethylene or pentamethylene substituted by methyl; and R303 and R30 are independently hydrogen, oxyl, hydroxy, aralkyl of 7 to 15 carbon atoms, alkoxy of 1 to 24 carbon atoms, alkyl of 1 to 42 carbon atoms, said alkyl substituted by one or two hydroxy groups, said alkyl substituted by alkylcarbonyloxy of 2 to 18 carbon atoms, or said alkyl interrupted by one to twenty oxygen atoms and substituted by one hydroxy, by alkylcarbonyloxy of 2 to 18 carbon atoms or by 4-hydroxy-3,5-di-tert-butylbenzoyloxy.
The piperazindione compound is preferably a compound of formula la-400
where p400 is 1 or 2, when p400 is 1 ,
G400 is alkyl of 1 to 18 carbon atoms, alkyl of 2 to 18 carbon atoms substituted by -NH2, by -OH, by halogen, by -OR6or by 4-hydroxy-3,5-di-tert-butylphenyl or by 4-hydroxy-3,5-dimethylphenyl, or by a mixture of these groups; or is interrupted by -O-, by -NH- or by -NR 06- or by a mixture of said groups; or G 0o is alkyl of 1 to 18 carbon atoms substituted by -COOR407 or by phenyl; when p400 is 2,
G400 is alkylene of 2 to 10 carbon atoms, alkenylene of 4 to 12 carbon atoms, alkylene of 3 to 15 carbon atoms substituted by one to four -OH or said alkylene interrupted by one to four oxygen atoms; or G400 is phenylene, C C alkylphenylene, -COO-, -CONH-,
-NH- or -NR406-, R oι> R o2. R403 and R404 are independently alkyl of 1 to 12 carbon atoms, said alkyl substituted by one or two hydroxy groups; or R40ι and R40 together, R403 and R 04 together or R401 and R402 together and with R 03 and R 04 together are tetramethylene, pentamethylene or pentamethylene substituted by methyl;
R405 is hydrogen, oxyl, hydroxy, cyanoethyl, phenylaikyl of 7 to 15 carbon atoms, said phenylaikyl substituted on the phenyl ring by one to three radicals selected from alkyl of 1 to 4 carbon atoms and alkoxy of 1 to 4 carbon atoms, phenylalkoxy of 7 to 15 carbon atoms, said phenylalkoxy substituted on the phenyl ring by one to three radicals selected from alkyl of 1 to 4 carbon atoms and alkoxy of 1 to 4 carbon atoms, cycloalkoxy of 5 to 12 carbon atoms, alkenyl of 3 to 8 carbon atoms, alkynyl of 3 to 8 carbon atoms, alkoxy of 1 to 24 carbon atoms, alkyl of 1 to 24 carbon atoms, said alkyl substituted by one or two hydroxy groups, said alkyl substituted by alkylcarbonyloxy of 2 to 18 carbon atoms, or said alkyl interrupted by one to twenty oxygen atoms and substituted by one hydroxy, by alkylcarbonyloxy of 2 to 18 carbon atoms or by 4- hydroxy-3,5-di-tert-butylbenzoyloxy; or R40s is alkanoyl of 1 to 8 carbon atoms, alkenoyl of 3 to 5 carbon atoms, alkanoyloxy of 1 to 18 carbon atoms, glycidyl, or a group -CH CH(OH)-E40o where E400 is hydrogen, methyl or phenyl; X400 is -0-, -NH- or -NR406-;
Z4Q0 is -NH2, -NHR406, -N(R406)2 or alkoxy of 1 to 18 carbon atoms;
R406 is alkyl of 1 to 8 carbon atoms, alkanoyl of 1 to 8 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylaikyl of 7 to 15 carbon atoms which is unsubstituted or substituted on the phenyl ring by alkyl of 1 to 4 carbon atoms, by alkoxy or 1 to 4 carbon atoms or by a mixture of said groups; or R4oβ is alkyl of 1 to 8 carbon atoms or alkanoyl of 1 to 8 carbon atoms substituted by -OH, by alkoxy of 1 to 12 carbon atoms, by benzophenonyl or benzophenonyloxy where one or both phenyl rings of the benzophenone moiety are unsubstituted or substituted by -OH, by halogen, by alkyl of 1 to 4 carbon atoms, by alkoxy of 1 to 4 carbon atoms or by a mixture of such groups; and
R407 is alkyl of 1 to 18 carbon atoms, alkyl of 2 to 18 carbon atoms which is substituted by -NH2, by by -N(R406)2, by nitro, by hydroxy, by alkoxy of 1 to 18 carbon atoms or by a mixture of said groups; or R^ is alkenyl of 3 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, or said cycloalkyl which is substituted by alkyl of 1 to 4 carbon atoms or is interrupted by -O-.
The piperazinone compound is preferably a compound of formula II-500 or III-500 wherein n50o is 1 or 2, p500 is 1 to 12, when n500 is 1 ,
G500 is alkyl of 1 to 18 carbon atoms, alkyl of 2 to 18 carbon atoms substituted by -NH2, by
-NH(R506), by -OH, by halogen, by-OR506, by 4-hydroxy-3,5-di-tert-butylphenyl or by 4-hydroxy-
3,5-dimethylphenyl, or by a mixture of these groups; or G50o is alkyl of 2 to 18 carbon atoms interrupted by -O-, by -CO-, by -NH- or by -NR506- or by a mixture of said groups; or G500 is alkyl of 1 to 18 carbon atoms substituted by -COOR507 or by phenyl; when n500 is 2,
G500 is alkylene of 2 to 10 carbon atoms, alkenylene of 4 to 12 carbon atoms, alkylene of 3 to 15 carbon atoms substituted by one to four -OH or said alkylene interrupted by one to four oxygen atoms; or G500 is phenylene, C C4alkylphenylene, -CO-(CH2)P5oo-CO-, -COO-, -CONH-,
-NH- or -NR506-;
R501. Rδ02> R503 and R50 are independently alkyl of 1 to 12 carbon atoms, said alkyl substituted by one or two hydroxy groups; or R50ι and R502 together, R503 and R504 together or R50ι and R502 together and with R503 and R504 together are tetramethylene, pentamethylene or pentamethylene substituted by methyl;
R505 >s hydrogen, oxyl, hydroxy, cyanoethyl, phenylaikyl of 7 to 15 carbon atoms, said phenylaikyl substituted on the phenyl ring by one to three radicals selected from alkyl of 1 to 4 carbon atoms and alkoxy of 1 to 4 carbon atoms, phenylalkoxy of 7 to 15 carbon atoms, said phenylalkoxy substituted on the phenyl ring by one to three radicals selected from alkyl of 1 to 4 carbon atoms and alkoxy of 1 to 4 carbon atoms, cycloalkoxy of 5 to 12 carbon atoms, alkenyl of 3 to 8 carbon atoms, alkynyl of 3 to 8 carbon atoms, alkoxy of 1 to 24 carbon atoms, alkyl of 1 to 24 carbon atoms, said alkyl substituted by one or two hydroxy groups, said aikyl substituted by alkylcarbonyloxy of 2 to 18 carbon atoms, or said alkyl interrupted by one to twenty oxygen atoms and substituted by one hydroxy, by alkylcarbonyloxy of 2 to 18 carbon atoms or by 4- hydroxy-3,5-di-tert-butylbenzoyloxy; or R505 is alkanoyl of 1 to 8 carbon atoms, alkenoyl of 3 to 5 carbon atoms, alkanoyloxy of 1 to 18 carbon atoms, glycidyl, or a group -CH2CH(OH)-E500 where E500 is hydrogen, methyl or phenyl; X500 is -0-, -NH- or -NR506-;
Z500 is -NH2, -NHR506, -N(R506)2 or alkoxy of 1 to 18 carbon atoms;
R506 is alkyl of 1 to 8 carbon atoms, alkanoyl of 1 to 8 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylaikyl of 7 to 15 carbon atoms which is unsubstituted or substituted on the phenyl ring by alkyl of 1 to 4 carbon atoms, by alkoxy of 1 to 4 carbon atoms or by a mixture of said groups; or R506 is alkyl of 1 to 8 carbon atoms or alkanoyl of 1 to 8 carbon atoms substituted by -OH, by alkoxy of 1 to 12 carbon atoms, by benzophenonyl or benzophenonyloxy where one or both phenyl rings of the benzophenone moiety are unsubstituted or substituted by -OH, by halogen, by alkyl of 1 to 4 carbon atoms, by alkoxy of 1 to 4 carbon atoms or by a mixture of such groups; R507 is hydrogen, alkyl of 1 to 18 carbon atoms, alkyl of 2 to 18 carbon atoms which is substituted by -NH2, by -NHR5o6, by -N(R506)2, by nitro, by hydroxy, by alkoxy of 1 to 18 carbon atoms or by a mixture of said groups; or R507 is alkenyl of 3 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, or said cycloalkyl which is substituted by alkyl of 1 to 4 carbon atoms or is interrupted by -0-, or R507 is phenyl or phenylaikyl of 7 to 15 carbon atoms; and R508 is alkyl of 1 to 12 carbon atoms or cycloalkyl of 3 to 12 carbon atoms.
According to a preferred embodiment, R 0ι, R202, R203 and R204 are each methyl, or R20ι and R202 together and R203 and R20 together are pentamethylene.
According to a further preferred embodiment, R30ι and R302 are each methyl, or R30ι and R302 together are pentamethylene.
According to another preferred embodiment, R40ι, R4o2, R4o3 and R 04 are each methyl, or R^ and R402 together and R403 and R 04 together are pentamethylene.
R501. R502. R503 and R504 are each preferably methyl, or R501 and R502 together and R503 and R50 together are preferably pentamethylene.
R505 is preferably hydrogen or methyl.
R508 is preferably n-butyl or cyclohexyl.
An example of aryl is phenyl and an example of aralkyl is benzyl.
Specific morpholinone compounds of formula la-100 or lb-100 which are useful in the instant invention include
(a-100) 5-hydroxymethyl-3,3,5-trimethyl-2-morpholinone,
(b-100) 5-dodecanoyloxymethyl-3,3,5-trimethyl-2-morpholinone,
(c-100) 5-(2-ethylhexanoyloxymethyl)-3,3,5-trimethyl-2-morpholinone,
(d-100) 5,5'-bis(decandioyloxymethyl-3,3,5-trimethyl-2-morpholinone),
(e-100) N-(2,2,6,6-tetramethylpiperidin-4-yl)-tetrahydro-1 ,4-oxazin-2-one,
(f-100) N-(1 ,2,2,6,6-pentamethylpiperidin-4-yl)-tetrahydro-6-methyl-1 ,4-oxazin-2-one, (g-100) N-(1 -acetyl-2,2,6,6-tetramethylpiperidin-4-yl)-3-n-tetradecyl-tetrahydro-1 ,4-oxazin-2-one,
(h-100) 3,3-pentamethylene-5,5-dimethyl-2-morpholinone,
(i-100) 3,3,4-trimethyl-5-ethyl-5-hydroxymethyl-2-morpholinone,
(j-100) 3,3,5, 5-tetramethyl-4-oxyl-2-morpholinone,
(k-100) 3,3-diethyl-5,5-dimethyl-4-hydroxy-2-morpholinone,
(1-100) 3,3,5,5-tetramethyl-4-( -methylbenzyl)-2-morpholinone,
(m-100) 3,3,5,5-tetramethyl-4-( -methylbenzyloxy)-2-morpholinone,
(n-100) N-(2-hydroxyethyl)-3,3,5,5-tetramethyl-2-morpholinone,
(o-100) 3,3,4,5-tetramethyl-5-(octadecanoyloxymethyl)-2-morpholinone, and
(p-100) bis(3,3,4,5-tetramethyl2-morpholinon-5-ylmethyl) terephthalate.
The compounds (a-100), (b-100), (c-100) and (d-100) are particularly preferred.
Specific oxazolidine compounds of formula la-200, lla-200 or llla-200 which are useful in the instant invention include
(a-200) 3,3-dimethyl-1 -oxa-4-azaspiro[4.5]decane,
(b-200) 2,2,4,4-tetramethyl-1 ,3-oxazolidine,
(c-200) 2,2,11 ,11 -tetramethyl-3,9-dioxa-dispiro(4.2.4.2]tetradecane,
(d-200) 3,3-dimethyl-1-oxa-4-oxyl-4-azaspiro[4.5]decane,
(e-200) 3,3-dimethyl-1 -oxa-4-hydroxy-4-azaspiro[4.5]decane,
(f-200) 3,3-dimethylol-1 -oxa-4-azaspiro[4.5]decane,
(g-200) 2,3,3-trimethyl-1 -oxa-4-azaspiro[4.5]decane,
(h-200) 3,3-di(2-hydroxyethyl)-1 -oxa-4-azaspiro[4.5]decane,
(i-200) 4-ethyl-2-isopropyloxazolidine,
(j-200) 1-aza-3,7-dioxa-2,8-diisopropyl-5-ethylbicyclo[3.3.0]octane,
(k-200) 3-acetyl-4,4-dimethyl-2-(3-amyl)oxazolidine,
(I-200) 3-acetyl-4-ethyl-2-phenyloxazolidine,
(m-200) N-(2-hydroxyethyl)-2,2'-diethyl-4,4'-dimethyl-1 ,3-oxazolidine,
(n-200) 1 -aza-3,7-dioxa-2,8-diphenyl-5-methylolbicyclo[3.3.0]octane, and
(o-200) 1-aza-3,7-dioxa-2,8-di-n-propyl-5-methylolbicyclo[3.3.0]octane.
The compounds (a-200), (b-200) and (c-200) are particularly preferred. Specific imidazoline compounds of formula la-300 which are useful in the instant invention include
(a-300) 2,2-pentamethylene-5,5-pentamethylene-imidazolidin-4-one,
(b-300) 2,2-pentamethylene-5,5-pentamethylene-imidazolidin-4-one-1-oxyl,
(c-300) 2,2,5,5-tetramethyl-4-oxoimidazoline-1 -oxyl,
(d-300) 2,5-dimethyl-2,5-diisobutyl-4-oxoimidazoline-1-oxyl,
(e-300) (2,2,6,6-tetramethylpiperidine-1-oxyl)-4-spiro-2'-(4-oxoimidiazoline-1-oxyl)-5'-spiro-4-
(2,2,6,6-tetramethylpiperidine-1-oxyl), (f-300) 2,5-dimethyl-2,5-diethyl-4-oxoimidazoiine-1 -oxyl, (g-300) 2,2-[(1 -methyl)-1 ,5-pentanediyl]-5,5-[(1 -methyl)-1 ,5-pentanediyl]-imidazolidin-4-one-1 - oxyl, (h-300) 2,2,5,5-tetramethyl-1-(2-hydroxyethyl)-imidazolin-4-one, (i-300) bis-[2-(2,2,5,5-tetramethyl-4-oxo-imidazolin-1 -yl)ethyl] sebacate, (j-300) 2,2,5,5-tetramethyl-1-methyl-3-(2-hydroxyethyl)-imidazolin-4-one, (k-300) 2,2,5,5-tetramethyl-1-methyl-3-[H(OCH2CH2)x]-imidazolin-4-one where x is 2 to 21 , (I-300) 2,2,5,5-tetramethyl-1 -methyl-3-[heptadecylcarbonyl(OCH2CH2) J-imidazolin-4-one where x is 2 to 21 , (m-300) 2,2,5,5-tetramethyl-1-methyl-3-[4-hydroxy-3,5-di-tert-butylbenzoyl(OCH2CH2)x]-imidazo lin-4-one where x is 2 to 21 , (n-300) 2,2,5,5-tetramethyl-1-methyl-3-[2-(heptadecylcarbonyloxyethyl]-imidazolin-4-one, (o-300) 2,2,5,5-tetramethyl-3-methyl-1-[2-(heptadecylcarbonyloxyethyl]-imidazolin-4-one, (p-300) the transesterification product of a 1 :1 methyl methacrylate: ethyl acrylate copolymer with 3-hydroxyethyl-2,2,5,5-tetramethylimidazolidin-4-one, and (q-300) the transesterification product of a 2:1 methyl methacrylate: ethyl acrylate copolymer with 3-hydroxyethyl-2,2,5,5-tetramethylimidazolidin-4-one.
The compound (a-300) is particularly preferred.
Specific piperazindione compounds of formula la-400 which are useful in the instant invention include
(a-400) 4-(3,5-dimethyl-4-hydroxybenzyl)-2,2,6,6-tetramethyl-3,5-diketopiperazine,
(b-400) 15-n-octadecyl-7,15-diazadispiro[5,1 ,5,3]hexadecane-14,16-dione, (c-400) 15-benzyl-7,15-diazadispiro[5.1.5.3]hexadecane-14,16-dione,
(d-400) 4-n-octadecyl-2,2,6,6-tetramethyl-3,5-diketopiperazine,
(e-400) 4,4'-n-octamethylene-bis(2,2,6,6-tetramethyl-3,5-diketopiperazine,
(f-400) 15-n-octadecyl-1 ,9-dimethyl-7,15-diazadispiro[5.1.5.3]hexadecane-14,16-dione,
(g-400) 3,3,5,5-tetramethyl-4-octyloxy-1-(4-hydroxy-3,5-ditert-butylbenzylpiperazin-2,6-dione,
(h-400) 3,3,5,5-tetramethyl-4-acetyl-1-(4-hydroxy-3,5-ditert-butylbenzylpiperazin-2,6-dione,
(i-400) tetramethylene bis[4-(3,3,4,5,5-pentamethylpiperazin-2,6-dione-1 -yl)butyrate],
(j-400) 3,3,5,5-tetramethyl-4-hydroxy-1-octylpiperazin-2,6-dione,
(k-400) 1 ,3,3,5,5-pentamethyl-4-oxylpiperazin-2,6-dione, and
(l-400) 3,3,4,5,5-pentamethyl-1-(ethoxycarbonylmethyl)-piperazin-2,6-dione.
The compounds (a-400) and (b-400) are particularly preferred.
Specific piperazinone compounds of formula II-500 or III-500 which are useful in the instant invention include
(a-500) 1 ,3,5-tris{N-cyclohexyl-N-[2-(2,2,6,6-tetramethylpiperazin-3-on-4-yl)ethyl]amino}-s- triazine, (b-500) 1 ,3,5-tris{N-cyclohexyl-N-[2-(1 ,2,2,6,6-pentamethylpiperazin-3-on-4-yl)ethyl]amino}-s- triazine, (c-500) 1 ,2-ethane-bis(3,3,5,5-tetramethylpiperazin-2-on-1 -yl), (d-500) 7-methyl-7,15-diazadispiro[5.1.5.3]hexadecane-14-one, (e-500) 1 ,3,3,5,5-pentamethyl-4-(2-hydroxyethyl)-2-ketopiperazine, (f-500) 3,3,5,5-tetramethyl-4-octyloxy-1-octyl-2-ketopiperazine, (g-500) 1 ,3,3,5,5-pentamethyl-4-oxyl-2-ketopiperazine, (h-500) 3,3,4,5,5-pentamethyl-1-(2-hydroxyethyl)piperazin-2-one, (i-500) 3,3,5,5-tetramethyl-4-cyclohexyloxy-1-[2-(dodecanoyloxy)ethyl]piperazin-2-one, (j-500) bis[2-(4-cyclohexyloxy-3,3,5,5-tetramethyl-2-ketopiperazin-1-yl)ethyl] sebacate, and (k-500) 4-octyloxy-3,3,5,5-tetramethyl-1-octadecylpiperazin-2-one.
The compounds (a-500), (b-500) and (c-500) are particularly preferred. In another preferred embodiment of the invention, the ratio by weight of components (i) to (ii) is from 4:1 to 1 :4, in particular from 2:1 to 1 :2.
In still another embodiment of the invention, the total amount of components (i) and (ii) are 0.01 to 10%, preferably 0.1 to 2 %, in particular 0.1 to 0.5%, by weight based on the wax.
The UV absorber of component (ii) is for example a benzotriazole, a benzophenone, an α- cyanoacrylate, an oxanilide, an s-triazine, a cinnamate, a malonate, a benzoate or a salicylate, or a mixture thereof, in particular a benzotriazole, a benzophenone or an s-triazine.
Examples of the UV absorbers useful in the instant invention are
(a) 4-octyloxy-2-hydroxybenzophenone,
(b) 4-methoxy-2-hydroxybenzophenone,
(c) 2-(2-hydroxy-5-methylphenyl)-2H-benzotriazole,
(d) 2-(2-hydroxy-5-tert-octylphenyl-2H-benzotriazole,
(e) 2-(2-hydroxy-3,5-di-tert-amylphenyl)-2H-benzotriazole,
(f) octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate,
(g) 2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole, (h) 2-(2-hydroxy-5-tert-butylphenyl)-2H-benzotriazole,
(i) 5-chloro-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole,
(j) 5-chloro-2-(2-hydroxy-3-tert-butyl-5-methylphenyl)-2H-benzotriazole,
(k) 2-(2-hydroxy-3-sec-butyl-5-tert-butylphenyl)-2H-benzotriazole,
(I) 2-(2-hydroxy-4-octyloxyphenyl)-2H-benzotriazole,
(m) 2-(2-hydroxy-3-dodecyl-5-methylphenyl)-2H-benzotriazole,
(n) 2-[2-hydroxy-3,5-di(α,α-dimethylbenzyl)phenyl]-2H-benzotriazole,
(o) 2-[2-hydroxy-3-(α, -dimethylbenzyl)-5-tert-octylphenyl]-2H-benzotriazole,
(p) 2-{2-hydroxy-3-tert-butyl-5-[2-(omega-hydroxy-octa(ethyleneoxy)carbonyl)ethyl]phenyl}-2H- benzotriazole, (q) 2-{2-hydroxy-3-tert-butyl-5-[2-(octyloxy)carbonyl)ethyl]phenyl}-2H- benzotriazole, (r) 2-ethylhexyl p-methoxycinnamate, (s) 4-methoxy-2,2'-dihydroxybenzophenone, (t) 4,4'dimethoxy-2,2'-dihydroxybenzophenone, (u) 2,4-bis(2,4-dimethylphenyl)-6-(2-hydroxy-4-octyloxyphenyl)-s-triazine, (v) 2,4-diphenyl-6-(2-hydroxy-4-hexyloxyphenyl)-s-triazine,
(w) 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s- triazine, (x) 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)-5-α-cumyl phenyl]-s-triazine, (y) reaction product of 2,4,6-tris(2,4-dihydroxyphenyl)-s-triazine with octyl α-haloacetate, and (z) the mixture of 3,3;3,5;5,5-methylene-bis[2,4-bis(2,4-dimethylphenyl)]-6-[2-hydroxy-4-(3- butyloxy-2-hydroxypropoxyphenyl)]-s-triazine.
The UV absorbers (a), (b), (d), (o), (p), (q), (y) and (z) are particularly preferred.
Another embodiment of the instant invention involves a composition wherein the antioxidant is a phenolic antioxidant, a phosphite, a nitrone, an amine oxide or a hydroxylamine, or mixture thereof.
Examples of the antioxidants useful in this invention are
(a') n-octadecyl 3,5-di-tert-butyl-4-hydroxyhydrocinnamate,
(b') neopentanetetrayl tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinammate),
(c') di-n-octadecyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate,
(d') 1 ,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate,
(e') thiodiethylene bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate),
(f) 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene,
(g') 3,6-dioxaoctamethylene bis(3-methyl-5-tert-butyl-4-hydroxyhydrocinnamate),
(h') 2,6-di-tert-butyl-p-cresol,
(i') 2,2'-ethylidene-bis(4,6-di-tert-butylphenol),
(j') 1 ,3,5-tris(2,6-dimethyl-4-tert-butyl-3-hydroxybenzyl) isocyanurate,
(k') 1 ,1 ,3,-tris(2-methyl-4-hydroxy-5-tert-butylphenyl)butane,
(I') 1 ,3,5-tris[2-(3,5-di-tert-butyl-4-hydroxyhydrocinnamoyloxy)ethyl] isocyanurate,
(m') 3,5-di-(3,5-di-tert-butyl-4-hydroxybenzyl)mesitol,
(n') hexamethylene bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate),
(o') 1-(3,5-di-tert-butyl-4-hydroxyanilino)-3,5-di(octylthio)-s-triazine,
(p') N,N'-hexamethylene-bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamamide),
(q') calcium bis(ethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate), (r') ethylene bis[3,3-di(3-tert-butyl-4-hydroxyphenyl)butyrate],
(s') octyl 3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetate,
(f) bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamoyl)hydrazide,
(u') N,N-di-(C14-C2 aIkyl)-N-methylamine oxide, and
(v') N,N-dialkylhydroxylamine prepared from di(hydrogenated tallow)amine by direct oxidation.
The antioxidants (a'), (b'), (d'), (f), (h') and (i') are particularly preferred.
It should be noted that candles contain a host of various components. The base materials may be made up of the following:
paraffin wax, natural oils, polyamide plus fatty acid/ester, fatty acids such as stearin, opacifiers, beeswax, glycerides plus oxidized wax, alcohols, and ethylene oligomers.
Candles also contain a number of additives such as the following:
mold release agents, fragrances, insect repellants or insecticides, hardeners, crystal modifiers, clarifiers, guttering reducers, colorants, f.p. control agents, stretchability improvers, gelling agents, extrusion aids, and vortex reducers.
Each of the various components are meant to control or modify the properties of the candle to insure proper burning, reduce channelling, aid in uniform melting, and the like. The colorants and fragrances obviously are there to provide the proper color, scent or other aesthetic appeal.
Of increasing importance are the transparent gel candles which look like clear glass, but which burn like a classical candle. As is discussed in detail in United States Patent No. 5,879,694, the relevant parts of which are incorporated herein by reference, these gel candles usually contain a copolymer selected from the group consisting of a triblock, radial block, diblock or multiblock copolymer classically made up of at least two thermodynamically incompatible segments containing both hard and soft segments. Typical of such block copolymers is KRATON® (Shell Chemical Co.) which consists of block segments of styrene monomer units and rubber monomer or comonomer units. The most common structure found in KRATON® D series is a linear ABA block with styrene-butadiene-styrene (SBS) or styrene-isoprene-styrene (SIS).
The following examples are meant for illustrative purposes only and are not to be construed to limit the instant invention in any manner whatsoever.
Raw Materials
Wax samples are supplied by the Candle-Lite Corporation. These samples contain dyes and fragrances.
The UV absorbers and hindered amine stabilizers are obtained from the Ciba Speciality Chemicals Corporation.
Sample Preparation
The wax samples obtained from the Candle-Lite Corporation already contain a dye and a fragrance (scent). In these cases, the wax is melted and the appropriate stabilizer(s) is (are) added and dissolved in the molten wax. The stabilized wax is then poured into five (5) 44 mm diameter aluminum pans giving five (5) wax disks. Sample Exposure
Triplicate samples of each disk are exposed under a bank of six (6) cool-white fluorescent lamps (40 watts) or under a bank of six (6) UV lamps having a wavelength of 368 nm with the test samples being twelve (12) inches (30.48 cm) below the lamps.
Dye color fade (or color change) is measured by a Macbeth ColorEye Spectrophotometer with a 6 inch integrating sphere. The conditions are: 10 degree observer; D65 illuminant and 8 degree viewing angle.
Initial color measurements are taken using the above parameters. The L, a and b values are calculated using the CIE system from the reflectance values. Yl is calculated from the L, a and b values. Subsequent measurements are taken at specified intervals. Delta L, a, b and Yl values are simply the difference between the initial values and the values at each interval. Delta(Δ) E is calculated as follows:
[(Delta L)2 + (Delta a)d + (Delta b)T = Delta E
Example 101 : 5-hvdroxymethyl-3.3.5-trimethyl-2-morpholinone.
This compound is made according to the procedure of Example A1 of WO 99/14206.
Example 102: 5-(2-ethylhexanoyloxvmethyl)-3.3.5-trimethyl-2-morpholinone.
This compound is made according to the procedure of Example A19 of WO 99/14206.
Example 103: 5.5'-bis(decandioyloxvmethvl-3.3.5-trimethyl-2-morpholinone).
This compound is made according to the procedure of Example A6 of WO 99/14206.
Example 104: 5-dodecanovloxvmethvl-3.3.5-trimethvl-2-morpholinone.
This compound is made according to the procedure of Example A4 of WO 99/14206.
Example 105: Color Fade of Pink Scented Candle Wax under UV Lamp Exposure.
A variety of different stabilizers are evaluated in pink scented candle wax obtained from the
Candle-Lite Corporation under UV lamp exposure. The ΔE values represent the change in color after the indicated days of exposure. A low ΔE value indicates less change in color and is highly desired.
Sample* (wt% add) ΔE after 37 davs
Blank (no add) 20.27
D (0.3%) 15.88
B (0.15%) + C (0.15%) 9.62
A (0.15%) + D (0.15%) 7.32
E (0.15%) + A (0.15%) 4.86
*)
A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
D is bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA.
E is 5-hydroxymethyl-3,3,5-trimethyl-2-morpholinone, the compound of instant Example 101.
These data show that a morpholinone compound (Compound E) in combination with an UV absorber protects the pink scented candle wax from unwanted discoloration far better than conventional stabilizer systems.
Example 106: Color Fade of Gray Scented Candle Wax under UV Lamp Exposure.
A variety of different stabilizers are evaluated in gray scented candle wax obtained from the
Candle-Lite Corporation under UV lamp exposure. The ΔE values represent the change in color after the indicated days of exposure. A low ΔE value indicates less change in color and is highly desired. Sample* (wt% add) ΔE after 26 days
Blank (no add) 29.81
F (0.3%) 25.37
B (0.15%) + C (0.15%) 10.27
A (0.3%) 9.45
A (0.15%) + F (0.15%) 4.81
G (0.15%) + H (0.15%) 3.90
*)
A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
F is bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-l) sebacate, TINUVIN® 123, CIBA.
G is the reaction product of 2,4,6-tris(2,4-dihydroxyphenyl)-s-triazine with octyl α-haloacetate.
H is 5-(2-ethylhexanoyloxymethyl)-3,3,5-trimethyl-2-morpholinone, the compound of instant
Example 102.
These data show that a morpholinone compound (Compound H) in combination with a UV absorber protects the gray scented candle wax from unwanted discoloration far better than conventional stabilizer systems.
Example 107: Color Fade of White Scented Candle Wax under Fluorescent Lamp Exposure. A variety of different stabilizers are evaluated in white scented candle wax obtained from the Candle-Lite Corporation under fluorescent lamp exposure. The ΔE values represent the change in color after the indicated days of exposure. A low ΔE value indicates less change in color and is highly desired. Samole* (wt% add ΔE after 33 davs
Blank (no add) 34.68
D (0.3%) 32.86
A (0.3%) 30.74
A (0.15%) + D (0.15%) 30.31
B (0.15%) + D (0.15%) 25.09
B (0.15%) + C (0.15%) 21.24
H (0.15%) + G (0.15%) 16.34
I (0.15%) + C (0.15%) 15.78
I (0.15%) + A (0.15%) 13.53
H (0.15%) + A (0.15%) 13.07
*) A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
D is bis(1 ,2,2,6, 6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA.
G is the reaction product of 2,4,6-tris(2,4-dihydroxyphenyl)-s-triazine with octyl α-haloacetate.
H is 5-(2-ethylhexanoyloxymethyl)-3,3,5-trimethyl-2-morpholinone, the compound of instant
Example 102.
I is 5,5'-bis(decandioyloxymethyl-3,3,5-trimethyl-2-morpholinone), the compound of instant
Example 103. These data show that a morpholinone compound (Compound H or I) in combination with a UV absorber protects the white scented candle wax from unwanted discoloration far better than conventional stabilizer systems.
Example 108: Color Fade of White Scented Candle Wax under UV Lamp Exposure.
A variety of different stabilizers are evaluated in white scented candle wax obtained from the
Candle-Lite Corporation under UV lamp exposure. The ΔE values represent the change in color after the indicated days of exposure. A low ΔE value indicates less change in color and is highly desired.
Sample* (wt% add) ΔE after 25 days
Blank (no add) 45.09
D (0.3%) 32.03
A (0.3%) 25.50
A (0.15%) + D (0.15%) 29.74
B (0.15%) + C (0.15%) 30.11
H (0.15%) + A (0.15%) 15.77
I (0.15%) + A (0.15%) 15.36
*)
A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
D is bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA. H is 5-(2-ethylhexanoyloxymethyl)-3,3,5-trimethyl-2-morpholinone, the compound of instant Example 102.
I is 5,5'-bis(decandioyloxymethyl-3,3,5-trimethyl-2-morpholinone), the compound of instant Example 103.
These data show that a morpholinone compound (Compound H or I) in combination with a UV absorber protects the white scented candle wax from unwanted discoloration far better than conventional stabilizer systems.
Example 109:
Green scented candle wax is well stabilized by 0.2% by weight of dimethyl p-methoxybenzylidenemalonate, SANDUVOR® PR 25, in combination with 0.2% by weight of N-(2,2,6,6- tetramethylpiperidin-4-yl)-tetrahydro-1 ,4-oxazin-2-one.
Example 110:
Yellow scented candle wax is well stabilized by 0.1% by weight of di(1 ,2,2,6,6-pentamethyl- piperidin-4-yl) p-methoxybenzylidenemalonate, SANDUVOR® PR 31 , in combination with 0.1% by weight of N-(1 ,2,2,6,6-pentamethylpiperidin-4-yl)-tetrahydro-6-methyl-1 ,4-oxazin-2-one.
Example 111 :
Red unscented candle wax is well stabilized by 0.1% by weight of dimethyl di(p-chlorophenyl)- methylenemalonate in combination with 0.1% by weight of N-(1-acetyl-2,2,6,6-tetramethyl- piperidin-4-yl)-3-n-tetradecyl-tetrahydro-1 ,4-oxazin-2-one.
Example 112:
Red unscented candle wax is well stabilized by 0.2% by weight of dimethyl di(p-methoxy- phenyl)methylenemalonate in combination with 0.2% by weight of 3,3-pentamethylene-5,5- dimethyl-2-morpholinone.
Example 113:
Red unscented candle wax is well stabilized by 0.1% by weight of 4,4'-dimethoxy-2,2'- dihydroxybenzophenone in combination with 0.1% by weight of 3,3,4-trimethyl-5-ethyl-5- hydroxymethyl-2-morpholinone. Example 114:
Red unscented candle wax is well stabilized by 0.2% by weight of 4-tert-butylphenyl 2-hydroxy- benzoate in combination with 0.1% by weight of 3,3,5,5-tetramethyl-4-oxyl-2-morpholinone.
Example 115:
Yellow unscented candle wax is well stabilized by 0.2% by weight of 2-ethoxy-2-ethyloxanilide in combination with 0.1% by weight of 3,3-diethyl-5,5-dimethyl-4-hydroxy-2-morpholinone.
Example 116:
Yellow unscented candle wax is well stabilized by 0.2% by weight of 3-hydroxyphenyl benzoate in combination with 0.2% by weight of 3,3,5,5-tetramethyl-4-(α-methylbenzyl)-2-morpholinone.
Example 117:
Blue unscented candle wax is well stabilized by 0.2% by weight of dodecyl 3-phenyl-3-methyl-α- cyanoacrylate in combination with 0.1% by weight of 3,3,5,5-tetramethyl-4-(α-methylbenzyloxy)-
2-morpholinone.
Example 18:
Blue unscented candle wax is well stabilized by 0.2% by weight of dodecyl 3,3-diphenyl-α- cyanoacrylate in combination with 0.2% by weight of N-(2-hydroxyethyl)-3,3,5,5-tetramethyl-2- morpholinone.
Example 119:
Yellow scented candle wax is well stabilized by 0.2% by weight of 2-{2-hydroxy-3-tert-butyl-5-[2-
(omega-hydroxy-octa(ethyleneoxy)carbonyl)ethyl]phenyl}-2H-benzotriazole, TINUVIN® 1130,
CIBA, in combination with 2% by weight of 3,3,4,5-tetramethyl-5-(octadecanoyloxymethyl)-2- morpholinone.
Example 120:
Yellow scented candle wax is well stabilized by 0.1% by weight of 2-[2-hydroxy-3-(α,α-dimethyi- benzyl)-5-tert-octylphenyl]-2H-benzotriazole, TINUVIN® 928, CIBA, in combination with 0.2% by weight of bis(3,3,4,5-tetramethyl2-morpholinon-5-ylmethyl) terephthalate. Example 121 :
Red scented candle wax is well stabilized by 0.1% by weight of 5-chloro-2-(2-hydroxy-3-tert- butyl-5-methylphenyl)-2H-benzotriazole, TINUVIN® 326, CIBA, in combination with 0.1% by weight of 5-hydroxymethyl-3,3,5-trimethyl-2-morpholinone.
Example 122:
Green scented candle wax is well stabilized by 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5- tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA, in combination with 0.1 % by weight of 5-dodecanoyloxymethyl-3,3,5-trimethyl-2-morpholinone.
Example 123:
Green scented candle wax is well stabilized by 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5- tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA, in combination with 0.1 % by weight of 3,3,5,5-tetramethyl-4-oxyl-2-morpholinone.
Example 124:
Blue scented candle wax is well stabilized by 0.1% by weight of 2-(2-hydroxy-5-tert-octyiphenyl-
2H-benzotriazole, TINUVIN® 329, CIBA, in combination with 0.1% by weight of 5-(2-ethyl- hexanoyloxymethyl)-3,3,5-trimethyl-2-morpholinone.
Example 125:
Blue scented candle wax is well stabilized by 0.2% by weight of 4-octyloxy-2-hydroxybenzo- phenone in combination with 0.1% by weight of 5,5'-bis(decandioyloxymethyl-3,3,5-trimethyl-2- morpholinone).
Example 126:
Red unscented candle wax is well stabilized by 0.2% by weight of 2-ethylhexyl p-methoxy- cinnamate in combination with 0.1% by weight of N-(2,2,6,6-tetramethylpiperidin-4-yl)- tetrahydro-1 ,4-oxazin-2-one.
Example 127: Red unscented candle wax is well stabilized by 0.1% by weight of 4,4'-dimethoxy-2,2'dihydroxy- benzophenone in combination with 0.1% by weight of N-(1 ,2,2,6,6-pentamethylpiperidin-4-yl)- tetrahydro-6-methyl-1 ,4-oxazin-2-one.
Example 128:
Yellow unscented candle wax is well stabilized by 0.1 % by weight of 2-ethoxy-2'-ethyl-5,4'-di- tert-butyloxanilide in combination with 0.1% by weight of N-(1-acetyl-2,2,6,6-tetramethyl- piperidin-4-yl)-3-n-tetradecyl-tetrahydro-1 ,4-oxazin-2-one.
Example 129:
Yellow unscented candle wax is well stabilized by 0.1% by weight of 2,4-bis(2,4-dimethyl- phenyl)-6-[2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine, TINUVIN® 400, CIBA, in combination with 0.1% by weight of 3,3-pentamethylene-5,5-dimethyl-2-morpholinone.
Example 130:
Blue scented candle wax is well stabilized by 0.1% by weight of 2,4-bis(2,4-dimethylphenyl)-6- [2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)-5-α-cumylphenyl]-s-triazine in combination with 0.1% by weight of 3,3,4-trimethyl-5-ethyl-5-hydroxymethyl-2-morpholinone.
Example 131 :
Blue unscented candle wax is well stabilized by 0.2% by weight of 2,4-bis(2,4-dimethylphenyl)- 6-(2-hydroxy-4-octyloxyphenyl)-s-triazine in combination with 0.1% by weight of 1-acetyl- 2,2,6,6-tetramethyl-4,4-(1-oxa-2,4-dioxo-3-dodecyliminotetramethylene)piperidine, TINUVIN® 440, CIBA, and 0.1% by weight of 3,3,5,5-tetramethyl-4-oxyl-2-morpholinone.
Example 132:
Blue unscented candle wax is well stabilized by 0.1% by weight of 2,4-bis(2,4-dimethylphenyl)- 6-[2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine, TINUVIN® 400, CIBA, in combination with 0.1% by weight of bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA, and 0.1% by weight of 5-hydroxymethy-3,3,5-trimethyl-2-morpholinone.
Example 133: White unscented candle wax is well stabilized by 0.1% by weight of 4-tert-octylphenyl2-hydroxy- benzoate in combination with 2% by weight of 3,3-diethyl-5,5-dimethyl-4-hydroxy-2- morpholinone.
Example 134:
White unscented candle wax is well stabilized by 0.1% by weight of 3-hydroxyphenyl benzoate in combination with 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydro- cinnamate, TINUVIN® 384, CIBA, and 0.1% by weight of 3,3,5,5-tetramethyl-4-(α-methyl- benzyl)-2-morpholinone.
Example 135:
Yellow scented candle wax is well stabilized by 0.1% by weight of dodecyl 3,3-diphenyl-α- cyanoacrylate in combination with 0.1% by weight of 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy- 4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine, TINUVIN® 400, CIBA, and 0.1% by weight of 3,3,5,5-tetramethyl-4-(α-methylbenzyloxy)-2-morpholinone.
Example 136:
Yellow scented candle wax is well stabilized by 0.1% by weight of pentaerythrityl tetrakis[3,3- diphenyl-α-cyanoacrylate] in combination with 0.2% by weight of N-(2-hydroxyethyl)-3,3,5,5- tetramethyl-2-morpholinone.
Example 137:
Red scented candle wax is well stabilized by 0.2% by weight of octyl 3-(p-methoxyphenyl)-3- phenyl-α-cyanoacrylate in combination with 0.2% by weight of 3,3,4,5-tetramethyl-5-(octa- decanoyloxymethyl)-2-morpholinone.
Example 201 : 3,3-Dimethyl-1 -oxa-4-azaspiro[4.5]decane.
Into a solution of 45 g (460 mmol) of cyclohexanone in 300 mL of toluene is added 35.6 g (400 mmol) of 2-amino-2,2-dimethylethanol. The reaction mixture is then heated to reflux and the byproduct water is collected by a Dean-Stark trap. After 16 hours of heating at reflux, the reaction mixture is allowed to cool to ambient temperature and is then concentrated under vacuum to give 55 g of a yellow liquid. The product, identified by mass spectroscopy (m/z = 169),is obtained in an 81.4% yield. The structure is confirmed by 1Hnmr.
1Hnmr (CDCI3) (300.08 MHz) δ 1.26 (s, 6H), 1.56-1.60 (m, 10H), 3,59 (s, 2H), 2.22 (s, 1 H).
Example 202: 2,2,4,4-Tetraιmethyl-1 ,3-oxazolidine.
Into a 500 mL, three-necked flask with a reverse Dean-Stark trap is added 45 g (500 mmol) of 2-amino-2,2-dimethylethanol, 40 g (700 mmol) of acetone and 200 mL of methylene chloride. The reaction mixture is heated to reflux for 16 hours until no starting 2-amino-2,2-dimethyl- ethanol is detected. The reaction mixture is allowed to cool to ambient temperature and is than concentrated under vacuum (200 mm Hg/30°C) to give 50 g (77.5% yield) of a colorless liquid. The product is identified by mass spectroscopy (m/z = 129) and 1Hnmr analysis.
1Hnmr (CDCI3) (300.08 MHz) δ 1.26 (s, 6H), 1.39 (s, 6H), 3.60 (s, 2H), 2.17 (s, 1H).
Example 203: 2,2,11 ,11-Tetramethyl-3,9-dioxa-dispiro(4.2.4.2]tetradecane. Into a solution of 40 g (360 mmol) of 1 ,4-cyclohexanedione in 200 mL of toluene is added 63.5 g (720 mmol) of 2-amino-2,2-dimethylethanol. The reaction mixture is then heated to reflux and the by-product water is collected in a Dean-Stark trap. After 16 hours of heating at reflux, the reaction is allowed to cool to ambient temperature and is then concentrated under vacuum to give 91 g (98.4% yield) of a brownish wet solid. The product is identified by mass spectroscopy (m/z = 254) and 1Hnmr.
1Hnmr (CDCI3) (300.08 MHz) δ 1.22 (s, 12H), 1.69 (s, 4H), 1.83 (d, 4H), 3.53 (s, 4H).
Example 204: Color Fade of Pink Scented Candle Wax under Fluorescent Lamp Exposure. A variety of different stabilizers are evaluated in pink scented candle wax obtained from the Candle-Lite Corporation under fluorescent lamp exposure. The ΔE values represent the change in color after the indicated days of exposure. A low ΔE value indicates less change in color and is highly desired. Sample* (wt% add) ΔE after 30 days
Blank (no add) 14.47
A (0.3%) 10.47
D (0.3%) 10.00
B (0.15%) + C (0.15%) 8.93
B (0.15%) + D (0.15%) 3.42
F (0.15%) + C (0.15%) 3.11
G (0.15%) + E (0.15%) 3.10
F (0.15%) + H (0.15%) 2.20
*)
A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
D is bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA.
E is 2-(2-hydroxy-3- -cumyl-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 928, CIBA.
F is 3,3-dimethyl-1 -oxa-4-azaspiro[4.5]decane, the compound of instant Example 201.
G is 2,2,4,4-tetramethyl-1 ,3-oxazolidine, the compound of instant Example 202.
H is 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy-4-(3-octyl/nonyl/decyloxy-2-hydroxypropoxy)-5-α- cumylphenyl]-s-triazine. These data show that an oxazolidine compound (Compound F or G) in combination with a UV absorber protects the pink scented candle wax from unwanted discoloration far better than conventional stabilizer systems.
Example 205: Color Fade of Pink Scented Candle Wax under UV Lamp Exposure.
A variety of different stabilizers are evaluated in pink scented candle wax obtained from the
Candle-Lite Corporation under UV lamp exposure. The ΔE values represent the change in color after the indicated days of exposure. A low ΔE value indicates less change in color and is highly desired.
Sample* (wt% add) ΔE after 32 days
Blank (no add) 21.10
D (0.3%) 16.24
B (0.15%) + C (0.15%) 11.15
A (0.15%) + D (0.15%) 9.84
F (0.15%) + H (0.15%) 5.97
F (0.15%) + C (0.15%) 4.73
G (0.15%) + E (0.15%) 2.88
*)
A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
D is bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA. E is the reaction product of 2,4,6-tris(2,4-dihydroxyphenyl)-s-triazine with octyl α-haloacetate.
F is 3,3-dimethyl-1-oxa-4-azaspiro[4.5]decane, the compound of instant Example 201.
G is 2,2,4,4-tetramethyl-1 ,3-oxazolidine, the compound of instant Example 202.
H is 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy-4-(3-octyl/nonyl/decyloxy-2-hydroxypropoxy)-5-α- cumylphenyl]-s-triazine.
These data show that an oxazolidine compound (Compound F or G) in combination with a UV absorber protects the pink scented candle wax from unwanted discoloration far better than conventional stabilizer systems.
Example 206: Color Fade of Gray Scented Candle Wax under Fluorescent Lamp Exposure. A variety of different stabilizers are evaluated in gray scented candle wax obtained from the Candle-Lite Corporation under fluorescent lamp exposure. The ΔE values represent the change in color after the indicated days of exposure. A low ΔE value indicates less change in color and is highly desired.
Sample* (wt% add) ΔE after 24 days
Blank (no add) 16.22
A (0.3%) 10.36
B (0.15%) + C (0.15%) 9.22
F (0.15%) + H (0.15%) 6.22
*)
A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
F is 3,3-dimethyl-1-oxa-4-azaspiro[4.5]decane, the compound of instant Example 201. H is 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy-4-(3-octyl/nonyl/decyloxy-2-hydroxypropoxy)-5-α- cumylphenyl]-s-triazine.
These data show that an oxazolidine compound (Compound F) in combination with an s-triazine UV absorber protects the gray scented candle wax from unwanted discoloration far better than conventional stabilizer systems.
Example 207: Color Fade of Gray Scented Candle Wax under UV Lamp Exposure. A variety of different stabilizers are evaluated in gray scented candle wax obtained from the Candle-Lite Corporation under fluorescent lamp exposure. The ΔE values represent the change in color after the indicated days of exposure. A low ΔE value indicates less change in color and is highly desired.
Sample* (wt% add) ΔE after 23 days
Blank (no add) 30.07
B (0.15%) + C (0.15%) 10.96
G (0.15%) + E (0.15%) 8.13
*)
B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
E is 2-(2-hydroxy-3-α-cumyl-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 928, CIBA.
G is 2,2,4,4-tetramethyl-1 ,3-oxazolidine, the compound of instant Example 202.
These data show that an oxazolidine compound (Compound G) in combination with a benzotriazole UV absorber protects the gray scented candle wax from unwanted discoloration far better than conventional stabilizer systems. Example 208:
Green scented candle wax is well stabilized by 0.2% by weight of dimethyl p-methoxybenzylidenemalonate, SANDUVOR® PR 25, in combination with 0.2% by weight of 3,3- dimethyl-1 -oxa-4-azaspiro[4.5]decane.
Example 209:
Yellow scented candle wax is well stabilized by 0.1% by weight of di(1 ,2,2,6,6-pentamethyl- piperidin-4-yl) p-methoxybenzylidenemalonate, SANDUVOR® PR 31 , in combination with 0.1% by weight of 2,2,4,4-tetramethyl-1 ,3-oxazolidine.
Example 210:
Red unscented candle wax is well stabilized by 0.1% by weight of dimethyl di(p-chlorophenyl)- methylenemalonate in combination with 0.1% by weight of 2,2,11 ,11 -tetramethyl-3,9-dioxa- dispiro(4.2.4.2]tetradecane.
Example 211 :
Red unscented candle wax is well stabilized by 0.2% by weight of dimethyl di(p-methoxy- phenyl)methylenemalonate in combination with 0.2% by weight of 3,3-dimethyl-1-oxa-4-oxyi-4- azaspiro[4.5]decane.
Example 212:
Red unscented candle wax is well stabilized by 0.1% by weight of 4,4'-dimethoxy-2,2'- dihydroxybenzophenone in combination with 0.1% by weight of 3,3-dimethyl-1 -oxa-4-hydroxy-4- azaspiro[4.5]decane.
Example 213:
Red unscented candle wax is well stabilized by 0.2% by weight of 4-tert-butylphenyl 2-hydroxy- benzoate in combination with 0.1% by weight of 3,3-dimethyloI-1-oxa-4-azaspiro[4.5]decane.
Example 214:
Yellow unscented candle wax is well stabilized by 0.2% by weight of 2-ethoxy-2-ethyloxanilide in combination with 0.1% by weight of 2,3,3-trimethyl-1-oxa-4-azaspiro[4.5]decane. Example 215:
Yellow unscented candle wax is well stabilized by 0.2% by weight of 3-hydroxyphenyl benzoate in combination with 0.2% by weight of 3,3-di(2-hydroxyethyl)-1-oxa-4-azaspiro[4.5]decane.
Example 216:
Blue unscented candle wax is well stabilized by 0.2% by weight of dodecyl 3-phenyl-3-methyl-α- cyanoacrylate in combination with 0.1% by weight of 4-ethyl-2-isopropyloxazolidine.
Example 217:
Blue unscented candle wax is well stabilized by 0.2% by weight of dodecyl 3,3-diphenyl-α- cyanoacrylate in combination with 0.2% by weight of 1 -aza-3,7-dioxa-2,8-diisopropyl-5-ethyl- bicyclo[3.3.0]octane.
Example 218:
Yellow scented candle wax is well stabilized by 0.2% by weight of 2-{2-hydroxy-3-tert-butyl-5-[2- (omega-hydroxy-octa(ethyleneoxy)carbonyl)ethyl]phenyl}-2H-benzotriazole, TINUVIN® 1130, CIBA, in combination with 2% by weight of 3-acetyl-4,4-dimethyl-2-(3-amyl)oxazolidine.
Example 219:
Yellow scented candle wax is well stabilized by 0.1% by weight of 2-[2-hydroxy-3-(α,α-dimethyl- benzyl)-5-tert-octylphenyl]-2H-benzotriazole, TINUVIN® 928, CIBA, in combination with 0.2% by weight of 3-acetyl-4-ethyl-2-phenyloxazolidine.
Example 220:
Red scented candle wax is well stabilized by 0.1% by weight of 5-chloro-2-(2-hydroxy-3-tert- butyl-5-methylphenyl)-2H-benzothazole, TINUVIN® 326, CIBA, in combination with 0.1% by weight of N-(2-hydroxyethyl)-2,2'-diethyl-4,4'-dimethyl-1 ,3-oxazolidine.
Example 221 :
Green scented candle wax is well stabilized by 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5- tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA, in combination with 0.1 % by weight of 1-aza-3,7-dioxa-2,8-diphenyl-5-methylolbicyclo[3.3.0]octane. Example 222:
Green scented candle wax is well stabilized by 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5- tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA, in combination with 0.1% by weight of 1-aza-3,7-dioxa-2,8-di-n-propyl-5-methylolbicyclo[3.3.0]octane.
Example 223:
Blue scented candle wax is well stabilized by 0.1% by weight of 2-(2-hydroxy-5-tert-octylphenyl-
2H-benzotriazole, TINUVIN® 329, CIBA, in combination with 0.1% by weight of 3,3-dimethyl-1- oxa-4-hydroxy-4-azaspiro[4.5]decane.
Example 224:
Blue scented candle wax is well stabilized by 0.2% by weight of 4-octyloxy-2-hydroxybenzo- phenone in combination with 0.1% by weight of 3,3-dimethyl-1-oxa-4-azaspiro[4.5]decane.
Example 225:
Red unscented candle wax is well stabilized by 0.2% by weight of 2-ethylhexyl p-methoxy- cinnamate in combination with 0.1% by weight of 2,2,4,4-tetramethyl-1 ,3-oxazolidine.
Example 226:
Red unscented candle wax is well stabilized by 0.1% by weight of 4,4'-dimethoxy-2,2'dihydroxy- benzophenone in combination with 0.1% by weight of 1-aza-3,7-dioxa-2,8-di-n-propyl-5- methylolbicyclo[3.3.0]octane.
Example 227:
Yellow unscented candle wax is well stabilized by 0.1% by weight of 2-ethoxy-2'-ethyl-5,4'-di- tert-butyloxanilide in combination with 0.1% by weight of 2,2,11 ,11 -tetramethyl-3, 9-dioxa- dispiro(4.2.4.2]tetradecane.
Example 228:
Yellow unscented candle wax is well stabilized by 0.1% by weight of 2,4-bis(2,4-dimethyl- phenyl)-6-[2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine, TINUVIN® 400, CIBA, in combination with 0.1% by weight of 3-acetyl-4,4-dimethyl-2-(3-amyl)oxazolidine. Example 229:
Blue scented candle wax is well stabilized by 0.1% by weight of 2,4-bis(2,4-dimethylphenyl)-6- [2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)-5-α-cumylphenyl]-s-triazine in combination with 0.1% by weight of 4-ethyI-2-isopropyloxazolidine.
Example 230:
Blue unscented candle wax is well stabilized by 0.2% by weight of 2,4-bis(2,4-dimethylphenyl)-
6-(2-hydroxy-4-octyloxyphenyl)-s-triazine in combination with 0.1% by weight of 1-acetyl-
2,2,6,6-tetramethyl-4,4-(1-oxa-2,4-dioxo-3-dodecyliminotetramethylene)piperidine, TINUVIN®
440, CIBA, and 0.1 % by weight of 1-aza-3,7-dioxa-2,8-di-n-propyl-5-methylolbicyclo[3.3.0]- octane.
Example 231 :
Blue unscented candle wax is well stabilized by 0.1% by weight of 2,4-bis(2,4-dimethylphenyl)- 6-[2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine, TINUVIN® 400, CIBA, in combination with 0.1% by weight of bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA, and 0.1% by weight of 2,2,4,4-tetramethyl-1 ,3-oxazolidine.
Example 232:
White unscented candle wax is well stabilized by 0.1% by weight of 4-tert-octylphenyl2-hydroxy- benzoate in combination with 2% by weight of 2,2,11 ,11-tetramethyl-3,9-dioxa-dispiro(4.2.4.2]- tetradecane.
Example 233:
White unscented candle wax is well stabilized by 0.1 % by weight of 3-hydroxyphenyl benzoate in combination with 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydro- cinnamate, TINUVIN® 384, CIBA, and 0.1% by weight of 3,3-diιmethyl-1-oxa-4-hydroxy-4- azaspiro[4.5]decane.
Example 234:
Yellow scented candle wax is well stabilized by 0.1 % by weight of dodecyl 3,3-diphenyl-α- cyanoacrylate in combination with 0.1% by weight of 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy- 4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine, TINUVIN® 400, CIBA, and 0.1 % by weight of 2,2,4,4-tetramethyl-1 ,3-oxazolidine.
Example 235:
Yellow scented candle wax is well stabilized by 0.1% by weight of pentaerythrityl tetrakis[3,3- diphenyl-α-cyanoacrylate] in combination with 0.2% by weight of 3-acetyl-4-ethyl-2-phenyl- oxazolidine.
Example 236:
Red scented candle wax is well stabilized by 0.2% by weight of octyl 3-(p-methoxyphenyl)-3- phenyl-α-cyanoacrylate in combination with 0.2% by weight of 1-aza-3,7-dioxa-2,8-diphenyl-5- methylolbicyclo[3.3.0]octane.
Example 301 : 2.2-Pentamethvlene-5,5-pentamethvlene-imidazolidin-4-one.
The title compound is prepared according to the procedure given in J. Organic Chemistry, 28,
3576 (1963).
Example 302: Color Fade of White Scented Candle Wax under Fluorescent Lamp Exposure. A variety of different stabilizers are evaluated in white scented candle wax obtained from the Candle-Lite Corporation under fluorescent lamp exposure. The ΔE values represent the change in color after the indicated days of exposure. A low ΔE value indicates less change in color and is highly desired.
Sample* (wt% add) ΔE after 28 days
Blank (no add) 34.05
A (0.3%) 30.28
A (0.15%) + D (0.15%) 29.49 D (0.3%) 31.20
B (0.15%) + D (0.15%) 24.23
B (0.15%) + C (0.15%) 20.10
F (0.15%) + C (0.15%) 15.63
F (0.15%) + A (0.15%) 13.07
F (0.15%) + E (0.15%) 11.26
*)
A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
D is bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA.
E is the reaction product of 2,4,6-tris(2,4-dihydroxyphenyl)-s-triazine with octyl α-haloacetate.
F is 2,2-pentamethylene-5,5-pentamethylene-imidazolidin-4-one, the compound of instant
Example 301.
These data show that an imidazolidine compound (Compound F) in combination with a UV absorber protects the white scented candle wax from unwanted discoloration far better than conventional stabilizer systems.
Example 303: Color Fade of White Scented Candle Wax under UV Lamp Exposure.
A variety of different stabilizers are evaluated in white scented candle wax obtained from the
Candle-Lite Corporation under UV lamp exposure. The ΔE values represent the change in color after the indicated days of exposure. A low ΔE value indicates less change in color and is highly desired. Sample* (wt% add) ΔE after 25 days
Blank (no add) 45.09
D (0.3%) 32.03
A (0.15%) + D (0.15%) 29.74
B (0.15%) + C (0.15%) 30.11
A (0.3%) 25.50
F (0.15%) + E (0.15%) 15.51
*)
A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
D is bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA.
E is the reaction product of 2,4,6-tris(2,4-dihydroxyphenyl)-s-triazine with octyl α-haloacetate.
F is 2,2-pentamethylene-5,5-pentamethylene-imidazolidin-4-one, the compound of instant
Example 301.
These data show that an imidazolidine compound (Compound F) in combination with a UV absorber protects the white scented candle wax from unwanted discoloration far better than conventional stabilizer systems.
Example 304: Color Fade of Gray Scented Candle Wax under Fluorescent Lamp Exposure. A variety of different stabilizers are evaluated in gray scented candle wax obtained from the Candle-Lite Corporation under fluorescent lamp exposure. The ΔE values represent the change in color after the indicated days of exposure. A low ΔE value indicates less change in color and is highly desired. Sample* (wt% add) ΔE after 41 days
Blank (no add) 17.73
A (0.3%) 13.71
B (0.15%) + C (0.15%) 11.54
F (0.15%) + C (0.15%) 9.95
F (0.15%) + G (0.15%) 9.89
*)
A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
F is 2,2-pentamethylene-5,5-pentamethylene-imidazolidin-4-one, the compound of instant
Example 301.
G is the mixture of 3,3;3,5;5,5-methylene-bis[2,4-bis(2,4-dimethylphenyl)]-6-[2-hydroxy-4-(3- butyloxy-2-hydroxypropoxyphenyl)]-s-triazine.
These data show that an imidazolidine compound (Compound F) in combination with an s- triazine UV absorber protects the gray scented candle wax from unwanted discoloration far better than conventional stabilizer systems.
Example 305:
Green scented candle wax is well stabilized by 0.2% by weight of dimethyl p-methoxybenzylidenemalonate, SANDUVOR® PR 25, in combination with 0.2% by weight of 2,2-penta- methylene-5,5-pentamethylene-imidazolidin-4-one-1-oxyl.
Example 306: Yellow scented candle wax is well stabilized by 0.1% by weight of di(1 ,2,2,6,6-pentamethyl- piperidin-4-yl) p-methoxybenzylidenemalonate, SANDUVOR® PR 31 , in combination with 0.1% by weight of 2,2,5,5-tetramethyl-1-(2-hydroxyethyl)-imidazolin-4-one.
Example 307:
Red unscented candle wax is well stabilized by 0.1% by weight of dimethyl di(p-chlorophenyl)- methylenemalonate in combination with 0.1% by weight of 2,2,5,5-tetramethyl-4-oxoimidazoline-
1-oxyl.
Example 308:
Red unscented candle wax is well stabilized by 0.2% by weight of dimethyl di(p-methoxy- phenyl)methylenemalonate in combination with 0.2% by weight of bis-[2-(2,2,5,5-tetramethyl-4- oxo-imidazolin-1 -yl)ethyl] sebacate.
Example 309:
Red unscented candle wax is well stabilized by 0.1% by weight of 4,4'-dimethoxy-2,2'- dihydroxybenzophenone in combination with 0.1% by weight of 2,5-dimethyl-2,5-diisobutyl-4- oxoimidazoline-1 -oxyl.
Example 310:
Red unscented candle wax is well stabilized by 0.2% by weight of 4-tert-butylphenyl 2-hydroxy- benzoate in combination with 0.1% by weight of 2,2,5,5-tetramethyl-1-methyl-3-(2-hydroxy- ethyl)-imidazolin-4-one.
Example 311 :
Yellow unscented candle wax is well stabilized by 0.2% by weight of 2-ethoxy-2-ethyloxanilide in combination with 0.1% by weight of (2,2,6,6-tetramethylpiperidine-1-oxyl)-4-spiro-2'-(4- oxoimidiazoline-1-oxyl)-5'-spiro-4-(2,2,6,6-tetramethylpiperidine-1-oxyl).
Example 312:
Yellow unscented candle wax is well stabilized by 0.2% by weight of 3-hydroxyphenyl benzoate in combination with 0.2% by weight of 2,2,5,5-tetramethyl-1-methyl-3-[H(OCH2CH2)x]-imidazolin- 4-one where x is 2 to 21 . Example 313:
Blue unscented candle wax is well stabilized by 0.2% by weight of dodecyl 3-phenyl-3-methyl-α- cyanoacrylate in combination with 0.1% by weight of 2,5-dimethyl-2,5-diethyl-4-oxoimidazoline-
1-oxyl.
Example 314:
Blue unscented candle wax is well stabilized by 0.2% by weight of dodecyl 3,3-diphenyl-α- cyanoacrylate in combination with 0.2% by weight of the transesterification product of a 1 :1 methyl methacrylate:ethyl acrylate copolymer with 3-hydroxyethyl-2,2,5,5-tetramethylimidazo- lidin-4-one.
Example 315:
Yellow scented candle wax is well stabilized by 0.2% by weight of 2-{2-hydroxy-3-tert-butyl-5-[2-
(omega-hydroxy-octa(ethyleneoxy)carbonyl)ethyl]phenyl}-2H-benzotriazole, TINUVIN® 1130,
CIBA, in combination with 2% by weight of the transesterification product of a 2:1 methyl methacrylate:ethyl acrylate copolymer with 3-hydroxyethyl-2,2,5,5-tetramethylimidazolidin-4- one.
Example 316:
Yellow scented candle wax is well stabilized by 0.1% by weight of 2-[2-hydroxy-3-(α,α-dimethyl- benzyl)-5-tert-octylphenyl]-2H-benzotriazole, TINUVIN® 928, CIBA, in combination with 0.2% by weight of 2,2-[(1 -methyl)-1 ,5-pentanediyl]-5,5-[(1 -methyl)-1 ,5-pentanediyl]-imidazolidin-4-one-1 - oxyl.
Example 317:
Red scented candle wax is well stabilized by 0.1% by weight of 5-chloro-2-(2-hydroxy-3-tert- butyl-5-methylphenyl)-2H-benzotriazole, TINUVIN® 326, CIBA, in combination with 0.1% by weight of 2,2,5,5-tetramethyl-1 -methyl-3-[heptadecylcarbonyl(OCH2CH2) J-imidazolin-4-one where x is 2 to 21.
Example 318:
Green scented candle wax is well stabilized by 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5- tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA, in combination with 0.1% by weight of 2,2,5,5-tetramethyl-1 -methyl-3-[4-hydroxy-3,5-di-tert-butylbenzoyl(OCH2CH2)x]-imidazolin-4- one where x is 2 to 21.
Example 319:
Green scented candle wax is well stabilized by 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5- tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA, in combination with 0.1% by weight of 2,2,5,5-tetramethyl-1-methyl-3-[2-(heptadecylcarbonyloxyethyl]-imidazolin-4-one.
Example 320:
Blue scented candle wax is well stabilized by 0.1% by weight of 2-(2-hydroxy-5-tert-octylphenyl-
2H-benzotriazole, TINUVIN® 329, CIBA, in combination with 0.1% by weight of 2,2,5,5-tetra- methyl-3-methyl-1 -[2-(heptadecylcarbonyloxyethyl]-imidazolin-4-one.
Example 321 :
Blue scented candle wax is well stabilized by 0.2% by weight of 4-octyloxy-2-hydroxybenzo- phenone in combination with 0.1% by weight of 2,2-pentamethylene-5,5-pentamethylene- imidazolidin-4-one-1 -oxyl.
Example 322:
Red unscented candle wax is well stabilized by 0.2% by weight of 2-ethylhexyl p-methoxy- cinnamate in combination with 0.1% by weight of 2,2-pentamethylene-5,5-pentamethylene- imidazolidin-4-one.
Example 323:
Red unscented candle wax is well stabilized by 0.1% by weight of 4,4'-dimethoxy-2,2'dihydroxy- benzophenone in combination with 0.1% by weight of the transesterification product of a 1 :1 methyl methacrylate:ethyl acrylate copolymer with 3-hydroxyethyl-2,2,5,5-tetramethylimidazo- lidin-4-one.
Example 324:
Yellow unscented candle wax is well stabilized by 0.1% by weight of 2-ethoxy-2'-ethyl-5,4'-di- tert-butyloxanilide in combination with 0.1% by weight of 2,2-pentamethylene-5,5-penta- methylene-imidazolidin-4-one. Example 325:
Yellow unscented candle wax is well stabilized by 0.1 % by weight of 2,4-bis(2,4-dimethyl- phenyl)-6-[2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine, TINUVIN® 400,
CIBA, in combination with 0.1% by weight of the transesterification product of a 2:1 methyl methacryiate:ethyl acrylate copolymer with 3-hydroxyethyl-2,2,5,5-tetramethylimidazolidin-4- one.
Example 326:
Blue scented candle wax is well stabilized by 0.1% by weight of 2,4-bis(2,4-dimethylphenyl)-6-
[2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)-5-α-cumylphenyl]-s-triazine in combination with 0.1% by weight of (2,2,6,6-tetramethylpiperidine-1-oxyl)-4-spiro-2'-(4-oxoimidiazoline-1- oxyl)-5'-spiro-4-(2,2,6,6-tetramethylpiperidine-1-oxyl).
Example 327:
Blue unscented candle wax is well stabilized by 0.2% by weight of 2,4-bis(2,4-dimethylphenyl)-
6-(2-hydroxy-4-octyloxyphenyl)-s-triazine in combination with 0.1% by weight of 1-acetyl-
2,2,6,6-tetramethyl-4,4-(1-oxa-2,4-dioxo-3-dodecyliminotetramethylene)piperidine, TINUVIN®
440, CIBA, and 0.1% by weight of bis-[2-(2,2,5,5-tetramethyl-4-oxo-imidazolin-1-yl)ethyl] sebacate.
Example 328:
Blue unscented candle wax is well stabilized by 0.1% by weight of 2,4-bis(2,4-dimethylphenyl)- 6-[2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyI]-s-triazine, TINUVIN® 400, CIBA, in combination with 0.1% by weight of bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, Ciba, and 0.1% by weight of 2,2,5,5-tetramethyl-1-methyl-3-[4-hydroxy-3,5-di- tert-butylbenzoy OCH^H^J-imidazolin^-one where x is 2 to 21.
Example 329:
White unscented candle wax is well stabilized by 0.1% by weight of 4-tert-octylphenyl2-hydroxy- benzoate in combination with 2% by weight of 2,2,5,5-tetramethyl-4-oxoimidazo!ine-1-oxyl.
Example 330: White unscented candle wax is well stabilized by 0.1 % by weight of 3-hydroxyphenyl benzoate in combination with 0.1 % by weight of octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydro- cinnamate, TINUVIN® 384, CIBA, and 0.1% by weight of 2,2,5,5-tetramethyl-1-methyl-3-[2- (heptadecylcarbonyloxyethyl]-imidazolin-4-one.
Example 331 :
Yellow scented candle wax is well stabilized by 0.1% by weight of dodecyl 3,3-diphenyl-α- cyanoacrylate in combination with 0.1% by weight of 2,4-bis(2,4-dimethylphenyi)-6-[2-hydroxy-
4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine, TINUVIN® 400, CIBA, and 0.1 % by weight of 2,2-[(1 -methyl)-1 ,5-pentanediyl]-5,5-[(1 -ιmethyl)-1 ,5-pentanediyl]-imidazolidin-4-one-1 ■ oxyl.
Example 332:
Yellow scented candle wax is well stabilized by 0.1% by weight of pentaerythrityl tetrakis[3,3- diphenyl-α-cyanoacrylate] in combination with 0.2% by weight of bis-[2-(2,2,5,5-tetramethyl-4- oxo-imidazolin-1 -yl)ethyl] sebacate.
Example 333:
Red scented candle wax is well stabilized by 0.2% by weight of octyl 3-(p-methoxyphenyl)-3- phenyl-α-cyanoacrylate in combination with 0.2% by weight of 2,2-pentamethylene-5,5-penta- methylene-imidazolidin-4-one.
Example 401 : 4-(3.5-Dimethvl-4-hvdroxvbenzyl)-2.2.6.6-tetramethvl-3,5-diketopiperazine. This compound is prepared according to the procedure of Example 5e of United States Patent No. 3,969,316.
Example 402: 15-n-Octadecyl-7,15-diazadispiro[5,1 ,5,3]hexadecane-14,16-dione.
This compound is prepared according to the procedure of Example 4 of United States Patent
No. 5,125,517.
Example 403: Color Fade of Pink Scented Candle Wax under Fluorescent Lamp Exposure. A variety of different stabilizers are evaluated in pink scented candle wax obtained from the Candle-Lite Corporation under fluorescent lamp exposure. The ΔE values represent the change in color after the indicated days of exposure. A low ΔE value indicates less change in color and is highly desired.
Sample* (wt% add) ΔE after 30 davs
Blank (no add) 14.47
A (0.3%) 10.47
D (0.3%) 14.05
B (0.15%) + C (0.15%) 8.93
A (0.15%) + D (0.15%) 5.72
E (0.15%) + F (0.15%) 4.49
*)
A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
D is bis(1-octyloxy-2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 123, CIBA.
E is 2-(2,4-dibutyloxyphenyl)-4,6-bis(2-hydroxy-4-butyloxyphenyl)-s-triazine.
F is 4-(3,5-dimethyl-4-hydroxybenzyl)-2,2,6,6-tetramethyl-3,5-diketopiperazine, the compound of
Example 401.
These data show that a piperazindione compound (Compound F) in combination with a UV absorber protects the pink scented candle wax from unwanted discoloration far better than conventional stabilizer systems. Example 404: Color Fade of Pink Scented Candle Wax under UV Lamp Exposure.
A variety of different stabilizers are evaluated in pink scented candle wax obtained from the
Candle-Lite Corporation under UV lamp exposure. The ΔE values represent the change in color after the indicated days of exposure. A low ΔE value indicates less change in color and is highly desired.
Sample* (wt% add) ΔE after 32 days
Blank (no add) 21.10
G (0.3%) 16.24
B (0.15%) + C (0.15%) 11.15
A (0.15%) + G (0.15%) 9.84
E (0.15%) + F (0.15%) 8.02
H (0.15%) + F (0.15%) 7.51
I (0.15%) + F (0.15%) 7.30
*)
A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
E is 2-(2,4-dibutyloxyphenyl)-4,6-bis(2-hydroxy-4-butyloxyphenyl)-s-triazine.
F is 4-(3,5-dimethyl-4-hydroxybenzyl)-2,2,6,6-tetramethyl-3,5-diketopiperazine, the compound of
Example 401.
G is bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA.
H is 5-trifluoromethyl-2-(2-hydroxy-3-α-cumyl-5-tert-octylphenyl)-2H-benzotriazole. I is C20-C40alkyl 3-(5-chloro-2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate.
These data show that a piperiazindione compound (Compound F) in combination with a UV absorber protects the pink scented candle wax from unwanted discoloration far better than conventional stabilizer systems.
Example 405: Color Fade of Gray Scented Candle Wax under UV Lamp Exposure.
A variety of different stabilizers are evaluated in gray scented candle wax obtained from the
Candle-Lite Corporation under UV lamp exposure. The ΔE values represent the change in color after the indicated days of exposure. A low ΔE value indicates less change in color and is highly desired.
Sample* (wt% add) ΔE after 23 days
Blank (no add) 30.07
D (0.3%) 25.70
A (0.3%) 9.14
B (0.15%) + C (0.15%) 10.96
A (0.15%) + D (0.15%) 5.11
E (0.15%) + F (0.15%) 4.60
H (0.15%) + F (0.15%) 4.96
A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA. B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA. C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
D is bis(1-octyloxy-2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 123, CIBA.
E is 2-(2,4-dibutyloxyphenyl)-4,6-bis(2-hydroxy-4-butyloxyphenyl)-s-triazine.
F is 4-(3,5-dimethyl-4-hydroxybenzyl)-2,2,6,6-tetramethyl-3,5-diketopiperazine, the compound of
Example 401.
H is 5-trifluoromethyl-2-(2-hydroxy-3-α-cumyl-5-tert-octylphenyl)-2H-benzotriazole.
These data show that a piperazindione compound (Compound F) in combination with a UV absorber protects the gray scented candle wax from unwanted discoloration far better than conventional stabilizer systems.
Example 406: Color Fade of White Scented Candle Wax under Fluorescent Lamp Exposure. A variety of different stabilizers are evaluated in white scented candle wax obtained from the Candle-Lite Corporation under fluorescent lamp exposure. The ΔE values represent the change in color after the indicated days of exposure. A low ΔE value indicates less change in color and is highly desired.
Sample* (wt% add) ΔE after 28 days
Blank (no add) 34.05
A (0.3%) 30.28
G (0.3%) 31.20
A (0.15%) + G (0.15%) 29.49
B (0.15%) + G (0.15%) 24.23
B (0.15%) + C (0.15%) 20.10
C (0.15%) + F (0.15%) 15.15 E (0.15%) + F (0.15%) 12.37
H (0.15%) + F (0.15%) 10.32
*)
A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
E is 2-(2,4-dibutyloxyphenyl)-4,6-bis(2-hydroxy-4-butyloxyphenyl)-s-triazine.
F is 4-(3,5-dimethyl-4-hydroxybenzyl)-2,2,6,6-tetramethyl-3,5-diketopiperazine, the compound of
Example 401.
G is bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA.
H is 5-trifluoromethyl-2-(2-hydroxy-3-α-cumyl-5-tert-octylphenyl)-2H-benzotriazole.
These data show that a piperazindione compound (Compound F) in combination with a benzotriazole UV absorber protects the white scented candle wax from unwanted discoloration far better than conventional stabilizer systems.
Example 407: Color Fade of White Scented Candle Wax under UV Lamp Exposure.
A variety of different stabilizers are evaluated in white scented candle wax obtained from the
Candle-Lite Corporation under UV lamp exposure. The ΔE values represent the change in color after the indicated days of exposure. A low ΔE value indicates less change in color and is highly desired.
Sample* (wt% add) ΔE after 25 days
Blank (no add) 45.09
G (0.3%) 32.30 B (0.15%) + C (0.15%) 30.11
A (0.15%) + G (0.15%) 29.74
A (0.3%) 25.50
I (0.15%) + J (0.15%) 17.82
E (0.15%) + F (0.15%) 17.43
H (0.15%) + F (0.15%) 10.84
*)
A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
E is 2-(2,4-dibutyloxyphenyl)-4,6-bis(2-hydroxy-4-butyloxyphenyl)-s-triazine.
F is 4-(3,5-dimethyl-4-hydroxybenzyl)-2,2,6,6-tetramethyl-3,5-diketopiperazine, the compound of
Example 401.
G is bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA.
H is 5-trifluoromethyl-2-(2-hydroxy-3-α-cumyl-5-tert-octylphenyl)-2H-benzotriazole.
I is the reaction product of 2,4,6-tris(2,4-dihydroxyphenyl)-s-triazine with octyl α-haloacetate.
J is 15-n-octadecyl-7, 15-diazadispiro[5, 1 ,5,3]hexadecane-14, 16-dione.
These data show that a piperazindione compound (Compound F or J) in combination with a benzotriazole UV absorber protects the white scented candle wax from unwanted discoloration far better than conventional stabilizer systems.
Example 408: Green scented candle wax is well stabilized by 0.2% by weight of dimethyl p-methoxybenzylidenemalonate, SANDUVOR® PR 25, in combination with 0.2% by weight of 15-benzyl- 7,15-diazadispiro[5.1.5.3]hexadecane-14,16-dione.
Example 409:
Yellow scented candle wax is well stabilized by 0.1% by weight of di(1 ,2,2,6,6-pentamethyl- piperidin-4-yl) p-methoxybenzylidenemalonate, SANDUVOR® PR 31 , in combination with 0.1% by weight of 4-n-octadecyl-2,2,6,6-tetramethyl-3,5-diketopiperazine.
Example 410:
Red unscented candle wax is well stabilized by 0.1% by weight of dimethyl di(p-chlorophenyl)- methylenemalonate in combination with 0.1% by weight of 4,4'-n-octamethylene-bis(2,2,6,6- tetramethyl-3,5-diketopiperazine.
Example 411 :
Red unscented candle wax is well stabilized by 0.2% by weight of dimethyl di(p-methoxy- phenyl)methylenemalonate in combination with 0.2% by weight of 15-n-octadecyl-1 ,9-dimethyl-
7,15-diazadispiro[5.1.5.3]hexadecane-14,16-dione.
Example 412:
Red unscented candle wax is well stabilized by 0.1% by weight of 4,4'-dimethoxy-2,2'- dihydroxybenzophenone in combination with 0.1% by weight of 3,3,5,5-tetramethyl-4-octyloxy-1-
(4-hydroxy-3,5-ditert-butylbenzylpiperazin-2,6-dione.
Example 413:
Red unscented candle wax is well stabilized by 0.2% by weight of 4-tert-butylphenyl 2-hydroxy- benzoate in combination with 0.1% by weight of 3,3,5,5-tetramethyl-4-acetyl-1-(4-hydroxy-3,5- ditert-butylbenzylpiperazin-2,6-dione.
Example 414:
Yellow unscented candle wax is well stabilized by 0.2% by weight of 2-ethoxy-2-ethyloxanilide in combination with 0.1% by weight of tetramethylene bis[4-(3,3,4,5,5-pentamethylpiperazin-2,6- dione-1-yl)butyrate]. Example 415:
Yellow unscented candle wax is well stabilized by 0.2% by weight of 3-hydroxyphenyl benzoate in combination with 0.2% by weight of 3,3,5,5-tetramethyl-4-hydroxy-1-octylpiperazin-2,6-dione.
Example 416:
Blue unscented candle wax is well stabilized by 0.2% by weight of dodecyl 3-phenyl-3-methyl-α- cyanoacrylate in combination with 0.1 % by weight of 1 ,3,3,5,5-pentamethyl-4-oxylpiperazin-2,6- dione.
Example 417:
Blue unscented candle wax is well stabilized by 0.2% by weight of dodecyl 3,3-diphenyl-α- cyanoacrylate in combination with 0.2% by weight of 3,3,4,5,5-pentamethyl-1-(ethoxycarbonyl- methyl)-piperazin-2,6-dione.
Example 418:
Yellow scented candle wax is well stabilized by 0.2% by weight of 2-{2-hydroxy-3-tert-butyl-5-[2-
(omega-hydroxy-octa(ethyleneoxy)carbonyI)ethyl]phenyl}-2H-benzotriazole, TINUVIN® 1130,
CIBA, in combination with 2% by weight of (a) 4-(3,5-dimethyl-4-hydroxybenzyl)-2,2,6,6-tetra- methyl-3,5-diketopiperazine.
Example 419:
Yellow scented candle wax is well stabilized by 0.1% by weight of 2-[2-hydroxy-3-(α,α-dimethyl- benzyl)-5-tert-octylphenyl]-2H-benzotriazole, TINUVIN® 928, CIBA, in combination with 0.2% by weight of 15-n-octadecyl-7,15-diazadispiro[5,1 ,5,3]hexadecane-14,16-dione.
Example 420:
Red scented candle wax is well stabilized by 0.1 % by weight of 5-chloro-2-(2-hydroxy-3-tert- butyl-5-methylphenyl)-2H-benzotriazole, TINUVIN® 326, CIBA, in combination with 0.1% by weight of 15-benzyl-7,15-diazadispiro[5.1.5.3]hexadecane-14,16-dione.
Example 421 : Green scented candle wax is well stabilized by 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5- tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA, in combination with 0.1% by weight of 4-n-octadecyl-2,2,6,6-tetramethyl-3,5-diketopiperazine.
Example 422:
Green scented candle wax is well stabilized by 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5- tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA, in combination with 0.1 % by weight of 4,4'-n-octamethylene-bis(2,2,6,6-tetramethyl-3,5-diketopiperazine.
Example 423:
Blue scented candle wax is well stabilized by 0.1% by weight of 2-(2-hydroxy-5-tert-octyiphenyl-
2H-benzotriazole, TINUVIN® 329, CIBA, in combination with 0.1% by weight of 15-n-octadecyl-
1 ,9-dimethyl-7,15-diazadispiro[5.1.5.3]hexadecane-14,16-dione.
Example 424:
Blue scented candle wax is well stabilized by 0.2% by weight of 4-octyloxy-2-hydroxybenzo- phenone in combination with 0.1% by weight of 3,3,5,5-tetramethyl-4-octyloxy-1-(4-hydroxy-3,5- ditert-butylbenzylpiperazin-2,6-dione.
Example 425:
Red unscented candle wax is well stabilized by 0.2% by weight of 2-ethylhexyl p-methoxy- cinnamate in combination with 0.1% by weight of 3,3,5,5-tetramethyl-4-acetyl-1-(4-hydroxy-3,5- ditert-butylbenzylpiperazin-2,6-dione.
Example 426:
Red unscented candle wax is well stabilized by 0.1% by weight of 4,4'-dimethoxy-2,2'dihydroxy- benzophenone in combination with 0.1 % by weight of tetramethylene bis[4-(3,3,4,5,5-penta- methylpiperazin-2,6-dione-1-yl)butyrate].
Example 427:
Yellow unscented candle wax is well stabilized by 0.1% by weight of 2-ethoxy-2'-ethyl-5,4'-di- tert-butyloxanilide in combination with 0.1% by weight of 3,3,5,5-tetramethyl-4-hydroxy-1-octyl- piperazin-2,6-dione. Example 428:
Yellow unscented candle wax is well stabilized by 0.1% by weight of 2,4-bis(2,4-dimethyl- phenyl)-6-[2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine, TINUVIN® 400, CIBA, in combination with 0.1% by weight of 1 ,3,3,5,5-pentamethyl-4-oxylpiperazin-2,6-dione.
Example 429:
Blue scented candle wax is well stabilized by 0.1 % by weight of 2,4-bis(2,4-dimethylphenyl)-6- [2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)-5-α-cumylphenyl]-s-triazine in combination with 0.1% by weight of 3,3,4,5,5-pentamethyl-1-(ethoxycarbonylmethyl)-piperazin-2,6-dione.
Example 430:
Blue unscented candle wax is well stabilized by 0.2% by weight of 2,4-bis(2,4-dimethylphenyl)-
6-(2-hydroxy-4-octyloxyphenyl)-s-triazine in combination with 0.1% by weight of 1-acetyl-
2,2,6,6-tetramethyl-4,4-(1-oxa-2,4-dioxo-3-dodecyliminotetramethylene)piperidine, TINUVIN®
440, CIBA, and 0.1 % by weight of 4-(3,5-dimethyl-4-hydroxybenzyl)-2,2,6,6-tetramethyl-3,5- diketopiperazine.
Example 431 :
Blue unscented candle wax is well stabilized by 0.1 % by weight of 2,4-bis(2,4-dimethylphenyl)- 6-[2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine, TINUVIN® 400, CIBA, in combination with 0.1% by weight of bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA, and 0.1% by weight of 15-n-octadecyl-7,15-diazadispiro[5,1 ,5,3]hexa- decane-14,16-dione.
Example 432:
White unscented candle wax is well stabilized by 0.1 % by weight of 4-tert-octylphenyl2-hydroxy- benzoate in combination with 2% by weight of 15-benzyl-7,15-diazadispiro[5.1.5.3]hexadecane- 14,16-dione;
Example 433:
White unscented candle wax is well stabilized by 0.1 % by weight of 3-hydroxyphenyl benzoate in combination with 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydro- cinnamate, TINUVIN® 384, CIBA, and 0.1% by weight of 4-n-octadecyl-2,2,6,6-tetramethyl-3,5- diketopiperazine.
Example 434:
Yellow scented candle wax is well stabilized by 0.1% by weight of dodecyl 3,3-diphenyl-α- cyanoacrylate in combination with 0.1% by weight of 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy- 4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine, TINUVIN® 400, CIBA, and 0.1% by weight of 4,4'-n-octamethylene-bis(2,2,6,6-tetramethyl-3,5-diketopiperazine.
Example 435:
Yellow scented candle wax is well stabilized by 0.1% by weight of pentaerythrityl tetrakis[3,3- diphenyl-α-cyanoacrylate] in combination with 0.2% by weight of 15-n-octadecyl-1 ,9-dimethyl- 7,15-diazadispiro[5.1.5.3]hexadecane-14,16-dione.
Example 436:
Red scented candle wax is well stabilized by 0.2% by weight of octyl 3-(p-methoxyphenyl)-3- phenyl-α-cyanoacrylate in combination with 0.2% by weight of 3,3,5,5-tetramethyl-4-octyloxy-1-
(4-hydroxy-3,5-ditert-butylbenzylpiperazin-2,6-dione.
Example 501 : 1 ,3,5-tris{N-cyclohexyl-N-[2-(2,2,6,6-tetramethyl-piperazin-3-on-4-yl)ethyl]amino}- s-triazine. This compound is a commercial stabilizer GOODRITE® 3150, obtained from the Goodrite Corporation and is made by the general procedures given in United States Patent No. 4,547,538.
Example 502: 1 ,3,5-tris{N-cyclohexyl-N-[2-(1 ,2,2,6,6-pentamethylpiperazin-3-on-4-yl)ethyl] amino}-s-triazine. This compound is a commercial stabilizer GOODRITE® 3159, obtained from the Goodrite Corporation and is made by the general procedures given in United States Patent No. 4,547,538.
Example 503: 1,2-ethane-bis(3,3,5,5-tetramethylpiperazin-2-on-1-vl). This compound is a commercial stabilizer GOODRITE® 3034, obtained from the Goodrite Corporation and is made by the general procedures given in United States Patent No. 4,547,538.
Example 504: Color Fade of Pink Scented Candle Wax under Fluorescent Lamp Exposure. A variety of different stabilizers are evaluated in pink scented candle wax obtained from the Candle-Lite Corporation under fluorescent lamp exposure. The ΔE values represent the change in color after the indicated days of exposure. A low ΔE value indicates less change in color and is highly desired.
Sample* (wt% add) ΔE after 35 days
Blank (no add) 13.66
A (0.3%) 10.04
D (0.3%) 9.37
B (0.15%) + C (0.15%) 7.12
A (0.15%) + D (0.15%) 3.96
G (0.15%) + F (0.15%) 2.78
H (0.15%) + C (0.15%) 2.46
G (0.15%) + E (0.15%) 1.80
*)
A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazoIe, TINUVIN® 329, CIBA.
C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA. D is bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA.
E is 2,4-bis(2,4-dimethylphenyl)-6-(2-hydroxy-4-octyloxyphenyl)-s-triazine, UV 1164, CYTEC.
F is ethyl 2-cyano-3,3-diphenylacrylate, UVINUL® N-35, BASF.
G is 1 ,3,5-tris{N-cyclohexyl-N-[2-(2,2,6,6-tetramethylpiperazin-3-on-4-yl)ethyl]amino}-s-triazine,
GOODRITE® 3150, GOODRITE, the compound of Example 501.
H is 1 ,2-ethane-bis(3,3,5,5-tetramethylpiperazin-2-on-1-yl), GOODRITE® 3034, GOODRITE, the compound of Example 503.
These data show that a piperazinone compound (Compound G or H) in combination with a UV absorber protects the pink scented candle wax from unwanted discoloration far better than conventional stabilizer systems.
Example 505: Color Fade of Pink Scented Candle Wax under UV Lamp Exposure.
A variety of different stabilizers are evaluated in pink scented candle wax obtained from the
Candle-Lite Corporation under UV lamp exposure. The ΔE values represent the change in color after the indicated days of exposure. A low ΔE value indicates less change in color and is highly desired.
Sample* (wt% add) ΔE after 37 days
Blank (no add) 20.27
D (0.3%) 15.88
A (0.15%) + D (0.15%) 7.32
B (0.15%) + C (0.15%) 9.62
H (0.15%) + C (0.15%) 4.83
G (0.15%) + E (0.15%) 2.88 *)
A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
D is bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA.
E is 2,4-bis(2,4-dimethylphenyl)-6-(2-hydroxy-4-octyloxyphenyl)-s-triazine, UV 1164, CYTEC.
G is 1 ,3,5-tris{N-cyclohexyl-N-[2-(2,2,6,6-tetramethylpiperazin-3-on-4-yl)ethyl]amino}-s-triazine,
GOODRITE® 3150, GOODRITE, the compound of Example 501.
H is 1 ,2-ethane-bis(3,3,5,5-tetramethyipiperazin-2-on-1-yl), GOODRITE® 3034, GOODRITE, the compound of Example 503.
These data show that a piperazinone compound (Compound G or H) in combination with a UV absorber protects the pink scented candle wax from unwanted discoloration far better than conventional stabilizer systems.
Example 506: Color Fade of Gray Scented Candle Wax under Fluorescent Lamp Exposure. A variety of different stabilizers are evaluated in gray scented candle wax obtained from the Candle-Lite Corporation under fluorescent lamp exposure. The ΔE values represent the change in color after the indicated days of exposure. A low ΔE value indicates less change in color and is highly desired.
Sample* (wt% add) ΔE after 34 days
Blank (no add) 16.01
A (0.3%) 11.26
1 (0.3%) 11.32
B (0.15%) + C (0.15%) 8.52 A (0.15%) + 1 (0.15%) 3.16
H (0.15%) + A (0.15%) 2.76
*)
A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
H is 1 ,2-ethane-bis(3,3,5,5-tetramethylpiperazin-2-on-1-yl), GOODRITE® 3034, GOODRITE, the compound of Example 503.
I is bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, TINUVIN® 123, CIBA.
These data show that a piperazinone compound (Compound H) in combination with a UV absorber protects the gray scented candle wax from unwanted discoloration far better than conventional stabilizer systems.
Example 507: Color Fade of Gray Scented Candle Wax under UV Lamp Exposure.
A variety of different stabilizers are evaluated in gray scented candle wax obtained from the
Candle-Lite Corporation under UV lamp exposure. The ΔE values represent the change in color after the indicated days of exposure. A low ΔE value indicates less change in color and is highly desired.
Sample* (wt% add) ΔE after 26 days
Blank (no add) 29.81
I (0.3%) 25.37
A (0.3%) 9.45
B (0.15%) + C (0.15%) 10.27 A (0.15%) + 1 (0.15%) 4.81
H (0.15%) + A (0.15%) 3.71
*)
A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
H is 1 ,2-ethane-bis(3,3,5,5-tetramethylpiperazin-2-on-1-yl), GOODRITE® 3034, GOODRITE, the compound of Example 503.
I is bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, TINUVIN® 123, CIBA.
These data show that a piperazinone compound (Compound H) in combination with a UV absorber protects the gray scented candle wax from unwanted discoloration far better than conventional stabilizer systems.
Example 508: Color Fade of White Scented Candle Wax under Fluorescent Lamp Exposure. A variety of different stabilizers are evaluated in white scented candle wax obtained from the Candle-Lite Corporation under fluorescent lamp exposure. The ΔE values represent the change in color after the indicated days of exposure. A low ΔE value indicates less change in color and is highly desired.
Sample* (wt% add) ΔE after 33 days
Blank (no add) 34.68
A (0.3%) 30.74
D (0.3%) 32.86 B (0.15%) + C (0.15%) 21.24
A (0.15%) + D (0.15%) 30.31
B (0.15%) + D (0.15%) 25.09
G (0.15%) + E (0.15%) 17.23
*)
A is octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA.
B is 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole, TINUVIN® 329, CIBA.
C is 4-octyloxy-2-hydroxybenzophenone, CHIMMASORB® 81 , CIBA.
D is bis(1 ,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, TINUVIN® 292, CIBA.
E is 2,4-bis(2,4-dimethylphenyl)-6-(2-hydroxy-4-octyloxyphenyl)-s-triazine, UV 1164, CYTEC.
G is 1 ,3,5-tris{N-cyclohexyl-N-[2-(2,2,6,6-tetramethylpiperazin-3-on-4-yl)ethyl]amino}-s-triazine,
GOODRITE® 3150, GOODRITE, the compound of Example 501.
These data show that a piperazinone compound (Compound G) in combination with a UV absorber protects the white scented candle wax from unwanted discoloration far better than conventional stabilizer systems.
Example 509:
Green scented candle wax is well stabilized by 0.2% by weight of dimethyl p-methoxybenzylidenemalonate, SANDUVOR® PR 25, in combination with 0.2% by weight of 7-methyi- 7,15-diazadispiro[5.1.5.3]hexadecane-14-one.
Example 510:
Yellow scented candle wax is well stabilized by 0.1% by weight of di(1 ,2,2,6,6-pentamethyl- piperidin-4-yl) p-methoxybenzylidenemalonate, SANDUVOR® PR 31 , in combination with 0.1% by weight of 1 ,3,3,5,5-pentamethyl-4-(2-hydroxyethyl)-2-ketopiperazine. Example 511 :
Red unscented candle wax is well stabilized by 0.1% by weight of dimethyl di(p-chlorophenyl)- methylenemalonate in combination with 0.1% by weight of 3,3,5,5-tetramethyl-4-octyloxy-1- octyl-2-ketopiperazine.
Example 512:
Red unscented candle wax is well stabilized by 0.2% by weight of dimethyl di(p-methoxy- phenyl)methylenemalonate in combination with 0.2% by weight of 1 ,3,3,5,5-pentamethyl-4-oxyl-
2-ketopiperazine.
Example 513:
Red unscented candle wax is well stabilized by 0.1% by weight of 4,4'-dimethoxy-2,2'- dihydroxybenzophenone in combination with 0.1% by weight of 3,3,4,5,5-pentamethyl-1-(2- hydroxyethyl)piperazin-2-one.
Example 514:
Red unscented candle wax is well stabilized by 0.2% by weight of 4-tert-butylphenyl 2-hydroxy- benzoate in combination with 0.1% by weight of 3,3,5,5-tetramethyl-4-cyclohexyloxy-1-[2-(do- decanoyloxy)ethyl]piperazin-2-one.
Example 515:
Yellow unscented candle wax is well stabilized by 0.2% by weight of 2-ethoxy-2-ethyloxanilide in combination with 0.1% by weight of bis[2-(4-cyclohexyloxy-3,3,5,5-tetramethyl-2-ketopiperazin- 1 -yl)ethyl] sebacate.
Example 516:
Yellow unscented candle wax is well stabilized by 0.2% by weight of 3-hydroxyphenyl benzoate in combination with 0.2% by weight of 4-octyloxy-3,3,5,5-tetramethyl-1-octadecyipiperazin-2- one.
Example 517:
Blue unscented candle wax is well stabilized by 0.2% by weight of dodecyl 3-phenyl-3-methyl-α- cyanoacrylate in combination with 0.1% by weight of 1 ,3,5-tris{N-cyclohexyl-N-[2-(2,2,6,6-tetra- methylpiperazin-3-on-4-yl)ethyl]amino}-s-triazine. Example 518:
Blue unscented candle wax is well stabilized by 0.2% by weight of dodecyl 3,3-diphenyl-α- cyanoacrylate in combination with 0.2% by weight of 1 ,3,5-tris{N-cyclohexyl-N-[2-(1 ,2,2,6,6- pentamethylpiperazin-3-on-4-yl)ethyl]amino}-s-triazine.
Example 519:
Yellow scented candle wax is well stabilized by 0.2% by weight of 2-{2-hydroxy-3-tert-butyl-5-[2- (omega-hydroxy-octa(ethyleneoxy)carbonyl)ethyl]phenyl}-2H-benzotriazole, TINUVIN® 1130, CIBA, in combination with 2% by weight of 1 ,2-ethane-bis(3,3,5,5-tetramethylpiperazin-2-on-1- yi).
Example 520:
Yellow scented candle wax is well stabilized by 0.1% by weight of 2-[2-hydroxy-3-(α,α-dimethyl- benzyl)-5-tert-octylphenyl]-2H-benzotriazole, TINUVIN® 928, CIBA, in combination with 0.2% by weight of 7-methyl-7,15-diazadispiro[5.1.5.3]hexadecane-14-one.
Example 521 :
Red scented candle wax is well stabilized by 0.1% by weight of 2-(2-hydroxy-5-methylphenyl)-
2H-benzotriazole, TINUVIN® P, CIBA, in combination with 0.1% by weight of 1 ,3,3,5,5- pentamethyl-4-(2-hydroxyethyl)-2-ketopiperazine.
Example 522:
Green scented candle wax is well stabilized by 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5- tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA, in combination with 0.1% by weight of 3,3,5,5-tetramethyl-4-octyloxy-1 -octyl-2-ketopiperazine.
Example 523:
Green scented candle wax is well stabilized by 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5- tert-butyl-4-hydroxyhydrocinnamate, TINUVIN® 384, CIBA, in combination with 0.1% by weight of 1 ,3,3,5,5-pentamethyl-4-oxyl-2-ketopiperazine.
Example 524: Blue scented candle wax is well stabilized by 0.1% by weight of 2-(2-hydroxy-5-tert-octylphenyl- 2H-benzotriazole, TINUVIN® 329, CIBA, in combination with 0.1 % by weight of 3,3,4,5, 5-penta- methyl-1-(2-hydroxyethyl)piperazin-2-one.
Example 525:
Blue scented candle wax is well stabilized by 0.2% by weight of 4-octyloxy-2-hydroxybenzo- phenone in combination with 0.1% by weight of 3,3,5,5-tetramethyl-4-cyclohexyloxy-1 -[2-(do- decanoyloxy)ethyl]piperazin-2-one.
Example 526:
Red unscented candle wax is well stabilized by 0.2% by weight of 2-ethylhexyl p-methoxy- cinnamate in combination with 0.1% by weight of bis[2-(4-cyclohexyloxy-3,3,5,5-tetramethyl-2- ketopiperazin-1 -yl)ethyl] sebacate.
Example 527:
Red unscented candle wax is well stabilized by 0.1% by weight of 4,4'-dimethoxy-2,2'dihydroxy- benzophenone in combination with 0.1% by weight of 4-octyloxy-3,3,5,5-tetramethyl-1- octadecylpiperazin-2-one.
Example 528:
Yellow unscented candle wax is well stabilized by 0.1% by weight of 2-ethoxy-2'-ethyl-5,4'-di- tert-butyloxanilide in combination with 0.1% by weight of 1 ,3,5-tris{N-cyclohexyl-N-[2-(2,2,6,6- tetramethylpiperazin-3-on-4-yl)ethyl]amino}-s-triazine.
Example 529:
Yellow unscented candle wax is well stabilized by 0.1% by weight of 2,4-bis(2,4-dimethyl- phenyl)-6-[2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine, TINUVIN® 400,
CIBA, in combination with 0.1% by weight of 1 ,3,5-tris{N-cyclohexyl-N-[2-(1 ,2,2,6,6-penta- methylpiperazin-3-on-4-yl)ethyl]amino}-s-triazine.
Example 530: Blue scented candle wax is well stabilized by 0.1% by weight of 2,4-bis(2,4-dimethylphenyl)-6- [2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)-5-α-cumylphenyl]-s-triazine in combination with 0.1% by weight of 1 ,2-ethane-bis(3,3,5,5-tetramethylpiperazin-2-on-1-yl).
Example 531 :
Blue unscented candle wax is well stabilized by 0.2% by weight of 2,4-bis(2,4-dimethylphenyl)- 6-(2-hydroxy-4-octyloxyphenyl)-s-triazine in combination with 0.1% by weight of 1-acetyl- 2,2,6,6-tetramethyl-4,4-(1 -oxa-2,4-dioxo-3-dodecyliminotetramethylene)piperidine, TINUVIN® 440, CIBA, and 0.1 % by weight of 7-methyl-7,15-diazadispiro[5.1.5.3]hexadecane-14-one.
Example 532:
Blue unscented candle wax is well stabilized by 0.1% by weight of 2,4-bis(2,4-dimethylphenyl)-
6-[2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine, TINUVIN® 400, CIBA, in combination with 0.1% by weight of bis(1,2,2,6,6-pentamethylpiperidin-4-yl) sebacate,
TINUVIN® 292, CIBA, and 0.1% by weight of 1 ,3,3,5,5-pentamethyl-4-(2-hydroxyethyl)-2-keto- piperazine.
Example 533:
White unscented candle wax is well stabilized by 0.1% by weight of 4-tert-octylphenyl2-hydroxy- benzoate in combination with 2% by weight of 3,3,5,5-tetramethyl-4-octyloxy-1 -octyl-2-keto- piperazine.
Example 534:
White unscented candle wax is well stabilized by 0.1 % by weight of 3-hydroxyphenyl benzoate in combination with 0.1% by weight of octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydro- cinnamate, TINUVIN® 384, CIBA, and 0.1% by weight of 1 ,3,3,5,5-pentamethyl-4-oxyl-2-keto- piperazine.
Example 535:
Yellow scented candle wax is well stabilized by 0.1% by weight of dodecyl 3,3-diphenyl-α- cyanoacrylate in combination with 0.1% by weight of 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy- 4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s-triazine, TINUVIN® 400, CIBA, and 0.1% by weight of 3,3,4,5,5-pentamethyl-1 -(2-hydroxyethyl)piperazin-2-one. Example 536:
Yellow scented candle wax is well stabilized by 0.1% by weight of pentaerythrityl tetrakis[3,3- diphenyl-α-cyanoacrylate] in combination with 0.2% by weight of 3,3,5,5-tetramethyl-4-cyclo- hexyloxy-1-[2-(dodecanoyloxy)ethyl]piperazin-2-one.
Example 537:
Red scented candle wax is well stabilized by 0.2% by weight of octyl 3-(p-methoxyphenyl)-3- phenyl-α-cyanoacrylate in combination with 0.2% by weight of bis[2-(4-cyclohexyloxy-3,3,5,5- tetramethyl-2-ketopiperazin-1 -yl)ethyl] sebacate.

Claims

CLAIMS:
1. A composition which comprises
(a) candle wax which is white and unscented; white and scented; dyed and unscented; dyed and scented; dipped and unscented; or dipped and scented, and
(b) a combination of
(i) a compound selected from the group consisting of a morpholinone compound containing a moiety of generic formula 1-100,
an oxazolidine compound containing a moiety of generic formula I-200, II-200 or III-200,
an imidazolidine compound containing a moiety of generic formula I-300, a piperazindione compound containing a moiety of generic formula 1-400, and
a piperazinone compound containing a moiety of formula 1-500;
and
(ii) an UV absorber or an antioxidant, or an UV absorber and an antioxidant, wherein the ratio by weight of (i) to (ii) is from 10:1 to 1 :10.
2. A composition according to claim 1 wherein the compound of component (b)(i) is a morpholinone compound of formula la-100 or lb-100;
where n100 is 1 or 2;
R10ι is hydrogen, alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms or cycloalkenyl of 5 to 12 carbon atoms;
R102 has the same meaning as R10 , or R102 is also hydroxyalkyl of 1 to 8 carbon atoms; or R101 and R102 together are tetramethylene, pentamethylene or pentamethylene substituted by methyl; Rι03 has the same meaning as R10ι;
R104 has the same meaning as R102; orR103 and Rι04 together are tetramethylene, pentamethylene or pentamethylene substituted by methyl;
R105 is hydrogen; alkyl of 1 to 18 carbon atoms; alkyl of 2 to 18 carbon atoms substituted by hydroxy, by phenyl or by both hydroxy and phenyl; oxyl; hydroxy; cyanoalkyl of 2 to 12 carbon atoms; cyanoalkoxy of 2 to 12 carbon atoms; alkoxy of 1 to 18 carbon atoms; cycloalkoxy of 5 to 12 carbon atoms; alkenyl of 3 to 8 carbon atoms; alkenyloxy of 3 to 8 carbon atoms; phenylaikyl of 7 to 12 carbon atoms; phenylaikyl of 7 to 12 carbon atoms substituted by hydroxy, by alkyl of 1 to 4 carbon atoms or by alkoxy of 1 to 4 carbon atoms, or by both said alkyl and said alkoxy; phenylalkoxy of 7 to 12 carbon atoms; alkanoyl of 2 to 8 carbon atoms; or a substituted 2,2,6,6- tetraalkylpiperidinyl moiety; when n10o is 1;
R106 is a straight or branched chain alkyl of 1 to 24 carbon atoms which is unsubstituted or substituted by one to six hydroxy or -ORi groups; or R106 is phenyl; when n10o is 2;
R106 is alkylene of 2 to 12 carbon atoms, o-phenylene, m-phenylene, p-phenylene or p-xylylene; and R10 is hydrogen or has the meaning of R10ι.
3. A composition according to claim 1 wherein the compound of component (b)(i) is a oxazolidine compound of formula la-200, lla-200 or llla-200
'205
where
R2oι> R202. R203 and R204 are independently alkyl of 1 to 8 carbon atoms, or R20ι and R202 together or R203 and R204 together are tetramethylene, pentamethylene or pentamethylene substituted by methyl;
R205 is hydrogen, oxyl, hydroxy, aralkyl of 7 to 15 carbon atoms, alkoxy of 1 to 24 carbon atoms, alkyl of 1 to 42 carbon atoms, said alkyl substituted by one or two hydroxy groups, said alkyl substituted by alkylcarbonyloxy of 2 to 18 carbon atoms, or said alkyl interrupted by one to twenty oxygen atoms and substituted by one hydroxy, by alkylcarbonyloxy of 2 to 18 carbon atoms or by 4-hydroxy-3,5-di-tert-butylbenzoyloxy; or R205 is -CO-CnH2n+ι where n is 1 to 17, and
R206 is alkyl of 1 to 8 carbon atoms, said alkyl substituted by one or two hydroxy groups, or is aryl of 6 to 10 carbon atoms.
4. A composition according to claim 1 wherein the compound of component (b)(i) is an imidazoline compound of formula la-300 where
R30ι and R302 are independently alkyl of 1 to 8 carbon atoms, or R30ι and R302 together are tetramethylene, pentamethylene or pentamethylene substituted by methyl; and
R303 and R304 are independently hydrogen, oxyl, hydroxy, aralkyl of 7 to 15 carbon atoms, alkoxy of 1 to 24 carbon atoms, alkyl of 1 to 42 carbon atoms, said alkyl substituted by one or two hydroxy groups, said alkyl substituted by alkylcarbonyloxy of 2 to 18 carbon atoms, or said alkyl interrupted by one to twenty oxygen atoms and substituted by one hydroxy, by alkylcarbonyloxy of 2 to 18 carbon atoms or by 4-hydroxy-3,5-di-tert-butylbenzoyloxy.
5. A composition according to claim 1 wherein the compound of component (b)(i) is a piperazindione compound of formula la-400
where p400 is 1 or 2, when p400 is 1 ,
G.400 is alkyl of 1 to 18 carbon atoms, alkyl of 2 to 18 carbon atoms substituted by -NH2, by -OH, by halogen, by -OR6or by 4-hydroxy-3,5-di-tert-butylphenyl or by 4-hydroxy-3,5-dimethylphenyl, or by a mixture of these groups; or is interrupted by -0-, by -NH- or by -NR 06- or by a mixture of said groups; or G400 is alkyl of 1 to 18 carbon atoms substituted by -COOR407 or by phenyl; when p400 is 2, G 0o is alkylene of 2 to 10 carbon atoms, alkenylene of 4 to 12 carbon atoms, alkylene of 3 to 15 carbon atoms substituted by one to four -OH or said alkylene interrupted by one to four oxygen atoms; or G400 is phenylene, CrC4alkylphenylene, -COO-, -CONH-,
-NH- or -NR406-,
R4oι. R4o2> R.03 and R40 are independently alkyl of 1 to 12 carbon atoms, said alkyl substituted by one or two hydroxy groups; or and R40 together or R40ι and R402 together and with R403 and R404 together are tetramethylene, pentamethylene or pentamethylene substituted by methyl;
R405 is hydrogen, oxyl, hydroxy, cyanoethyl, phenylaikyl of 7 to 15 carbon atoms, said phenylaikyl substituted on the phenyl ring by one to three radicals selected from alkyl of 1 to 4 carbon atoms and alkoxy of 1 to 4 carbon atoms, phenylalkoxy of 7 to 15 carbon atoms, said phenylalkoxy substituted on the phenyl ring by one to three radicals selected from alkyl of 1 to 4 carbon atoms and alkoxy of 1 to 4 carbon atoms, cycloalkoxy of 5 to 12 carbon atoms, alkenyl of 3 to 8 carbon atoms, alkynyl of 3 to 8 carbon atoms, alkoxy of 1 to 24 carbon atoms, alkyl of 1 to 24 carbon atoms, said alkyl substituted by one or two hydroxy groups, said alkyl substituted by alkylcarbonyloxy of 2 to 18 carbon atoms, or said alkyl interrupted by one to twenty oxygen atoms and substituted by one hydroxy, by alkylcarbonyloxy of 2 to 18 carbon atoms or by 4- hydroxy-3,5-di-tert-butylbenzoyloxy; or R405 is alkanoyl of 1 to 8 carbon atoms, alkenoyl of 3 to 5 carbon atoms, alkanoyloxy of 1 to 18 carbon atoms, glycidyl, or a group -CH2CH(OH)-E400 where E400 is hydrogen, methyl or phenyl; X400 is -O-, -NH- or -NR^e-;
Z40o is -NH2, -NHR^e, -N(R406)2 or alkoxy of 1 to 18 carbon atoms;
R406 is alkyl of 1 to 8 carbon atoms, alkanoyl of 1 to 8 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylaikyl of 7 to 15 carbon atoms which is unsubstituted or substituted on the phenyl ring by alkyl of 1 to 4 carbon atoms, by alkoxy or 1 to 4 carbon atoms or by a mixture of said groups; or R406 is alkyl of 1 to 8 carbon atoms or alkanoyl of 1 to 8 carbon atoms substituted by -OH, by alkoxy of 1 to 12 carbon atoms, by benzophenonyl or benzophenonyloxy where one or both phenyl rings of the benzophenone moiety are unsubstituted or substituted by -OH, by halogen, by alkyl of 1 to 4 carbon atoms, by alkoxy of 1 to 4 carbon atoms or by a mixture of such groups; and
R40 is alkyl of 1 to 18 carbon atoms, alkyl of 2 to 18 carbon atoms which is substituted by -NH , by -NHR406, by -N(R406)2ι by nitro, by hydroxy, by alkoxy of 1 to 18 carbon atoms or by a mixture of said groups; or R 0 is alkenyl of 3 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, or said cycloalkyl which is substituted by alkyl of 1 to 4 carbon atoms or is interrupted by -0-.
6. A composition according to claim 1 wherein the compound of component (b)(i) is a piperazinone compound of formula II-500 or III-500
wherein n50o is 1 or 2,
Psoo is l to 12, when n50o is 1 ,
G50o is alkyl of 1 to 18 carbon atoms, alkyl of 2 to 18 carbon atoms substituted by -NH2, by
-NH(R5o6), by -OH, by halogen, by -OR506, by 4-hydroxy-3,5-di-tert-butylphenyl or by 4-hydroxy-
3,5-dimethylphenyl, or by a mixture of these groups; or G50o is alkyl of 2 to 18 carbon atoms interrupted by -0-, by -CO-, by -NH- or by -NR506- or by a mixture of said groups; or G50o is alkyl of 1 to 18 carbon atoms substituted by-COOR507 or by phenyl; when n 0o is 2,
G500 is alkylene of 2 to 10 carbon atoms, alkenylene of 4 to 12 carbon atoms, alkylene of 3 to 15 carbon atoms substituted by one to four -OH or said alkylene interrupted by one to four oxygen atoms; or G500 is phenylene, CrC^lkylphenylene, -CO-(CH2)p50o-CO-, -COO-, -CONH-,
-NH- or -NR506-;
R501, R502, R5Q3 and R504 are independently alkyl of 1 to 12 carbon atoms, said alkyl substituted by one or two hydroxy groups; or R5Qι and R502 together, R503 and R504 together or R50ι and R5o2 together and with R503 and R504 together are tetramethylene, pentamethylene or pentamethylene substituted by methyl;
R505 is hydrogen, oxyl, hydroxy, cyanoethyl, phenylaikyl of 7 to 15 carbon atoms, said phenylaikyl substituted on the phenyl ring by one to three radicals selected from alkyl of 1 to 4 carbon atoms and alkoxy of 1 to 4 carbon atoms, phenylalkoxy of 7 to 15 carbon atoms, said phenylalkoxy substituted on the phenyl ring by one to three radicals selected from alkyl of 1 to 4 carbon atoms and alkoxy of 1 to 4 carbon atoms, cycloalkoxy of 5 to 12 carbon atoms, alkenyl of 3 to 8 carbon atoms, alkynyl of 3 to 8 carbon atoms, alkoxy of 1 to 24 carbon atoms, alkyl of 1 to 24 carbon atoms, said alkyl substituted by one or two hydroxy groups, said alkyl substituted by alkylcarbonyloxy of 2 to 18 carbon atoms, or said alkyl interrupted by one to twenty oxygen atoms and substituted by one hydroxy, by alkylcarbonyloxy of 2 to 18 carbon atoms or by 4- hydroxy-3,5-di-tert-butylbenzoyloxy; or R505 is alkanoyl of 1 to 8 carbon atoms, alkenoyl of 3 to 5 carbon atoms, alkanoyloxy of 1 to 18 carbon atoms, glycidyl, or a group -CH2CH(OH)-E500 where E50o is hydrogen, methyl or phenyl;
Xsoo is -O-, -NH- or -NR506-;
Z500 is -NH2, -NHR506, -N(R5o6)2 or alkoxy of 1 to 18 carbon atoms;
R506 is alkyl of 1 to 8 carbon atoms, alkanoyl of 1 to 8 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylaikyl of 7 to 15 carbon atoms which is unsubstituted or substituted on the phenyl ring by alkyl of 1 to 4 carbon atoms, by alkoxy of 1 to 4 carbon atoms or by a mixture of said groups; or R506 is alkyl of 1 to 8 carbon atoms or alkanoyl of 1 to 8 carbon atoms substituted by -OH, by alkoxy of 1 to 12 carbon atoms, by benzophenonyl or benzophenonyloxy where one or both phenyl rings of the benzophenone moiety are unsubstituted or substituted by -OH, by halogen, by alkyl of 1 to 4 carbon atoms, by alkoxy of 1 to 4 carbon atoms or by a mixture of such groups;
R507 is hydrogen, alkyl of 1 to 18 carbon atoms, alkyl of 2 to 18 carbon atoms which is substituted by -NH2, by -NHR506, by -N(R5o6)2, by nitro, by hydroxy, by alkoxy of 1 to 18 carbon atoms or by a mixture of said groups; or R50 is alkenyl of 3 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, or said cycloalkyl which is substituted by alkyl of 1 to 4 carbon atoms or is interrupted by -0-, or R507 is phenyl or phenylaikyl of 7 to 15 carbon atoms; and R5o8 is alkyl of 1 to 12 carbon atoms or cycloalkyl of 3 to 12 carbon atoms.
7. A composition according to claim 3 where in the compound of formula la-200, lla-200 or llla-200, R20i, R202, R203 and R20 are each methyl, or R201 and R202 together and R203 and R204 together are pentamethylene.
8. A composition according to claim 4 where in the compound of formula la-300, R30ι and R302 are each methyl, or R30ι and R302 together are pentamethylene.
9. A composition according to claim 5 where in the compound of formula la-400, R40ι, R^, Rrø and R404 are each methyl, or R40ι and R^ together and R 03 and Rω together are pentamethylene.
10. A composition according to claim 6 where in the compound of formula II-500 or III-500, R50ι, R502- R503 and R50 are each methyl, or R50ι and R502 together and R503 and R504 together are pentamethylene.
11. A composition according to claim 6 where in the compound of formula II-500 or III-500, R505 is hydrogen or methyl.
12. A composition according to claim 6 where in the compound of formula III-500, R508 is n-butyl or cyclohexyl.
13. A composition according to claim 1 wherein the morpholinone compound is
(a-100) 5-hydroxymethyl-3,3,5-trimethyl-2-morpholinone,
(b-100) 5-dodecanoyloxymethyl-3,3,5-trimethyl-2-morpholinone,
(c-100) 5-(2-ethylhexanoyloxymethyl)-3,3,5-trimethyl-2-morpholinone,
(d-100) 5,5'-bis(decandioyloxymethyl-3,3,5-trimethyl-2-morpholinone),
(e-100) N-(2,2,6,6-tetramethylpiperidin-4-yl)-tetrahydro-1 ,4-oxazin-2-one,
(f-100) N-(1 ,2,2,6,6-pentamethylpiperidin-4-yl)-tetrahydro-6-methyl-1 ,4-oxazin-2-one,
(g-100) N-(1 -acetyl-2,2,6,6-tetramethylpiperidin-4-yl)-3-n-tetradecyl-tetrahydro-1 ,4-oxazin-2-one,
(h-100) 3,3-pentamethylene-5,5-dimethyl-2-morpholinone,
(i-100) 3,3,4-trimethyl-5-ethyl-5-hydroxymethyl-2-morpholinone,
(j-100) 3,3,5,5-tetramethyl-4-oxyl-2-morpholinone,
(k-100) 3,3-diethyl-5,5-dimethyl-4-hydroxy-2-morpholinone,
(1-100) 3,3,5,5-tetramethyl-4-(α-methylbenzyl)-2-morpholinone,
(m-100) 3,3,5,5-tetramethyl-4-(α-methylbenzyloxy)-2-morpholinone,
(n-100) N-(2-hydroxyethyl)-3,3,5,5-tetramethyl-2-morpholinone,
(o-100) 3,3,4,5-tetramethyl-5-(octadecanoyloxymethyl)-2-morpholinone, or
(p-100) bis(3,3,4,5-tetramethyl2-morpholinon-5-ylmethyl) terephthalate;
the oxazolidine compound is
(a-200) 3,3-dimethyl-1 -oxa-4-azaspiro[4.5]decane,
(b-200) 2,2,4, 4-tetramethyl-1 ,3-oxazolidine,
(c-200) 2,2,11 ,11 -tetramethyl-3,9-dioxa-dispiro(4.2.4.2]tetradecane,
(d-200) 3,3-dimethyl-1 -oxa-4-oxyl-4-azaspiro[4.5]decane,
(e-200) 3,3-dimethyl-1 -oxa-4-hydroxy-4-azaspiro[4.5]decane,
(f-200) 3,3-dimethylol-1 -oxa-4-azaspiro[4.5]decane,
(g-200) 2,3,3-trimethyl-1 -oxa-4-azaspiro[4.5]decane,
(h-200) 3,3-di(2-hydroxyethyl)-1 -oxa-4-azaspiro[4.5]decane,
(i-200) 4-ethyl-2-isopropyloxazolidine,
Q-200) 1-aza-3,7-dioxa-2,8-diisopropyl-5-ethylbicyclo[3.3.0]octane,
(k-200) 3-acetyl-4,4-dimethyl-2-(3-amyl)oxazolidine,
(I-200) 3-acetyl-4-ethyl-2-phenyloxazolidine,
(m-200) N-(2-hydroxyethyl)-2,2'-diethyl-4,4'-dimethyl-1 ,3-oxazolidine, (n-200) 1 -aza-3,7-dioxa-2,8-diphenyl-5-methylolbicyclo[3.3.0]octane, or (o-200) 1-aza-3,7-dioxa-2,8-di-n-propyl-5-methylolbicyclo[3.3.0]octane;
the imidazoline compound is
(a-300) 2,2-pentamethylene-5,5-pentamethylene-imidazolidin-4-one,
(b-300) 2,2-pentamethylene-5,5-pentamethylene-imidazolidin-4-one-1-oxyl,
(c-300) 2,2,5,5-tetramethyl-4-oxoimidazoline-1 -oxyl,
(d-300) 2,5-dimethyl-2,5-diisobutyl-4-oxoimidazoline-1 -oxyl,
(e-300) (2,2,6,6-tetramethylpiperidine-1-oxyl)-4-spiro-2'-(4-oxoimidiazoline-1-oxyl)-5'-spiro-4-
(2,2,6,6-tetramethylpiperidine-1-oxyl), (f-300) 2,5-dimethyl-2,5-diethyl-4-oxoimidazoline-1 -oxyl, (g-300) 2,2-[(1 -methyl)-1 ,5-pentanediyl]-5,5-[(1 -methyl)-1 ,5-pentanediyl]-imidazolidin-4-one-1 - oxyl, (h-300) 2,2,5,5-tetramethyl-1-(2-hydroxyethyl)-imidazolin-4-one, (i-300) bis-[2-(2,2,5,5-tetramethyl-4-oxo-imidazolin-1 -yl)ethyl] sebacate, (j-300) 2,2,5,5-tetramethyl-1-methyl-3-(2-hydroxyethyl)-imidazolin-4-one, (k-300) 2,2,5,5-tetramethyl-1-methyl-3-[H(OCH2CH2)x]-imidazolin-4-one where x is 2 to 21 , (I-300) 2,2,5,5-tetramethyl-1 -methyl-3-[heptadecylcarbonyl(OCH2CH2)x]-imidazolin-4-one where x is 2 to 21 , (m-300) 2,2,5,5-tetramethyl-1-methyl-3-[4-hydroxy-3,5-di-tert-butylbenzoyl(OCH2CH2)χ]-imidazo lin-4-one where x is 2 to 21 , (n-300) 2,2,5,5-tetramethyl-1-methyl-3-[2-(heptadecyIcarbonyloxyethyl]-imidazolin-4-one, (o-300) 2,2,5,5-tetramethyl-3-methyl-1-[2-(heptadecylcarbonyloxyethyl]-imidazolin-4-one, (p-300) the transesterification product of a 1 :1 methyl methacrylate:ethyl acrylate copolymer with 3-hydroxyethyl-2,2,5,5-tetramethylimidazolidin-4-one, or (q-300) the transesterification product of a 2:1 methyl methacrylate:ethyl acrylate copolymer with 3-hydroxyethyl-2,2,5,5-tetramethylimidazolidin-4-one;
the piperazindione compound is
(a-400) 4-(3,5-dimethyl-4-hydroxybenzyl)-2,2,6,6-tetramethyl-3,5-diketopiperazine,
(b-400) 15-n-octadecyl-7,15-diazadispiro[5,1 ,5,3]hexadecane-14,16-dione,
(c-400) 15-benzyl-7,15-diazadispiro[5.1.5.3]hexadecane-14,16-dione,
(d-400) 4-n-octadecyl-2,2,6,6-tetramethyl-3,5-diketopiperazine,
(e-400) 4,4'-n-octamethylene-bis(2,2,6,6-tetramethyl-3,5-diketopiperazine, (f-400) 15-n-octadecyl-1 ,9-dimethyl-7,15-diazadispiro[5.1.5.3]hexadecane-14,16-dione,
(g-400) 3,3,5,5-tetramethyl-4-octyloxy-1-(4-hydroxy-3,5-ditert-butylbenzylpiperazin-2,6-dione,
(h-400) 3,3,5,5-tetramethyl-4-acetyl-1-(4-hydroxy-3,5-ditert-butylbenzylpiperazin-2,6-dione,
(i-400) tetramethylene bis[4-(3,3,4,5,5-pentamethylpiperazin-2,6-dione-1-yl)butyrate],
(j-400) 3,3,5,5-tetramethyl-4-hydroxy-1-octylpiperazin-2,6-dione,
(k-400) 1 ,3,3,5,5-pentamethyl-4-oxylpiperazin-2,6-dione, or
(I-400) 3,3,4,5,5-pentamethyl-1 -(ethoxycarbonylmethyl)-piperazin-2,6-dione; and
the piperazinone compound is
(a-500) 1 ,3,5-tris{N-cyclohexyl-N-[2-(2,2,6,6-tetramethylpiperazin-3-on-4-yl)ethyl]amino}-s- triazine, (b-500) 1,3,5-tris{N-cyclohexyl-N-[2-(1,2,2,6,6-pentamethylpiperazin-3-on-4-yl)ethyl]amino}-s- triazine, (c-500) 1 ,2-ethane-bis(3,3,5,5-tetramethylpiperazin-2-on-1 -yl), (d-500) 7-methyl-7,15-diazadispiro[5.1.5.3]hexadecane-14-one, (e-500) 1,3,3,5,5-pentamethyl-4-(2-hydroxyethyl)-2-ketopiperazine, (f-500) 3,3,5,5-tetramethyl-4-octyloxy-1-octyl-2-ketopiperazine, (g-500) 1 ,3,3,5,5-pentamethyl-4-oxyl-2-ketopiperazine, (h-500) 3,3,4,5,5-pentamethyl-1-(2-hydroxyethyl)piperazin-2-one, (i-500) 3,3,5,5-tetramethyl-4-cyclohexyloxy-1-[2-(dodecanoyloxy)ethyl]piperazin-2-one, (j-500) bis[2-(4-cyclohexyloxy-3,3,5,5-tetramethyl-2-ketopiperazin-1-yl)ethyl] sebacate, or (k-500) 4-octyloxy-3,3,5,5-tetramethyl-1-octadecylpiperazin-2-one.
14. A composition according to claim 1 wherein the total amount of components (i) and (ii) are 0.01 to 10% by weight based on the wax.
15. A composition according to claim 1 wherein the UV absorber of component (ii) is a benzotriazole, a benzophenone, an α-cyanoacrylate, an oxanilide, an s-triazine, a cinnamate, a malonate, a benzoate or a salicylate, or a mixture thereof.
16. A composition according to claim 1 wherein the UV absorber is
(a) 4-octyloxy-2-hydroxybenzophenone,
(b) 4-methoxy-2-hydroxybenzophenone, (c) 2-(2-hydroxy-5-methylphenyl)-2H-benzotriazole, (d) 2-(2-hydroxy-5-tert-octylphenyl-2H-benzotriazole,
(e) 2-(2-hydroxy-3,5-di-tert-amylphenyl)-2H-benzotriazole,
(f) octyl 3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate,
(g) 2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole, (h) 2-(2-hydroxy-5-tert-butylphenyl)-2H-benzotriazole,
(i) 5-chloro-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole,
(j) 5-chloro-2-(2-hydroxy-3-tert-butyl-5-methylphenyl)-2H-benzotriazole,
(k) 2-(2-hydroxy-3-sec-butyl-5-tert-butylphenyl)-2H-benzotriazole,
(I) 2-(2-hydroxy-4-octyloxyphenyl)-2H-benzotriazole,
(m) 2-(2-hydroxy-3-dodecyl-5-methylphenyl)-2H-benzotriazole,
(n) 2-[2-hydroxy-3,5-di(α,α-dimethylbenzyl)phenyl]-2H-benzotriazole,
(o) 2-[2-hydroxy-3-(α,α-dimethylbenzyl)-5-tert-octylphenyl]-2H-benzotriazole,
(p) 2-{2-hydroxy-3-tert-butyl-5-[2-(omega-hydroxy-octa(ethyleneoxy)carbonyl)ethyl]phenyl}-2H- benzotriazole, (q) 2-{2-hydroxy-3-tert-butyl-5-[2-(octyloxy)carbonyl)ethyl]phenyl}-2H- benzotriazole, (r) 2-ethylhexyl p-methoxycinnamate, (s) 4-methoxy-2,2'-dihydroxybenzophenone, (t) 4,4'dimethoxy-2,2'-dihydroxybenzophenone,
(u) 2,4-bis(2,4-dimethylphenyl)-6-(2-hydroxy-4-octyloxyphenyl)-s-triazine, (v) 2,4-diphenyl-6-(2-hydroxy-4-hexyloxyphenyl)-s-triazine, (w) 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)phenyl]-s- triazine, (x) 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy-4-(3-do-/tri-decyloxy-2-hydroxypropoxy)-5-α-cumyl phenyl]-s-triazine, (y) reaction product of 2,4,6-tris(2,4-dihydroxyphenyl)-s-triazine with octyl α-haloacetate, or (z) the mixture of 3,3;3,5;5,5-methylene-bis[2,4-bis(2,4-dimethylphenyl)]-6-[2-hydroxy-4-(3- butyloxy-2-hydroxypropoxyphenyl)]-s-triazine.
17. A composition according to claim 1 wherein the antioxidant is a phenolic antioxidant, a phosphite, a nitrone, an amine oxide or a hydroxylamine, or mixture thereof.
18. A composition according to claim 1 wherein the antioxidant is
(a') n-octadecyl 3,5-di-tert-butyl-4-hydroxyhydrocinnamate,
(b') neopentanetetrayl tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinammate),
(c') di-n-octadecyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate,
(d') 1 ,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate,
(e') thiodiethylene bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate),
(f) 1 ,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene,
(g') 3,6-dioxaoctamethylene bis(3-methyl-5-tert-butyl-4-hydroxyhydrocinnamate) ,
(h') 2,6-di-tert-butyl-p-cresol,
(i') 2,2'-ethylidene-bis(4,6-di-tert-butylphenoI),
(j') 1 ,3,5-tris(2,6-dimethyl-4-tert-butyl-3-hydroxybenzyl) isocyanurate,
(k') 1 ,1 ,3,-tris(2-methyl-4-hydroxy-5-tert-butylphenyl)butane,
(I') 1 ,3,5-tris[2-(3,5-di-tert-butyl-4-hydroxyhydrocinnamoyloxy)ethyl] isocyanurate,
(m') 3,5-di-(3,5-di-tert-butyl-4-hydroxybenzyl)mesitol,
(n') hexamethylene bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate),
(o') 1-(3,5-di-tert-butyl-4-hydroxyaniIino)-3,5-di(octylthio)-s-triazine,
(p') N,N,-hexamethylene-bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamamide),
(q') calcium bis(ethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate),
(r') ethylene bis[3,3-di(3-tert-butyl-4-hydroxyphenyl)butyrate],
(s') octyl 3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetate,
(f) bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamoyl)hydrazide,
(u') N,N-di-(C14-C2 alkyl)-N-methylamine oxide, or
(v') N,N-diaIkylhydroxylamine prepared from di(hydrogenated tallow)amine by direct oxidation.
EP02716843A 2001-04-02 2002-03-25 Stabilized candle wax Withdrawn EP1383832A1 (en)

Applications Claiming Priority (11)

Application Number Priority Date Filing Date Title
US09/824,194 US6544305B2 (en) 2001-04-02 2001-04-02 Candle wax stabilized with piperazinones
US09/825,552 US6562084B2 (en) 2001-04-02 2001-04-02 Candle wax stabilized with piperazindiones
US824146 2001-04-02
US824048 2001-04-02
US824194 2001-04-02
US09/824,146 US6544304B2 (en) 2001-04-02 2001-04-02 Candle wax stabilized with morpholinones
US825552 2001-04-02
US824141 2001-04-02
US09/824,048 US6547840B2 (en) 2001-04-02 2001-04-02 Candle wax stabilized with imidazolidines
US09/824,141 US6540795B2 (en) 2001-04-02 2001-04-02 Candle wax stabilized with oxazolidines
PCT/EP2002/003310 WO2002079313A1 (en) 2001-04-02 2002-03-25 Stabilized candle wax

Publications (1)

Publication Number Publication Date
EP1383832A1 true EP1383832A1 (en) 2004-01-28

Family

ID=27542239

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02716843A Withdrawn EP1383832A1 (en) 2001-04-02 2002-03-25 Stabilized candle wax

Country Status (3)

Country Link
EP (1) EP1383832A1 (en)
JP (1) JP2004523638A (en)
WO (1) WO2002079313A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007128672A1 (en) * 2006-05-03 2007-11-15 Ciba Holding Inc. Substituted hexahydro-1,4-diazepin-5-ones and compositions stabilized therewith
EP2618824A4 (en) 2010-09-20 2015-05-06 Kareus Therapeutics Sa Methods and compositions for treatment of diabetes and dyslipidemia
SG11201805780VA (en) 2016-02-26 2018-09-27 Exxonmobil Res & Eng Co Coating compositions for oriented strand boards and associated methods of use

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5280124A (en) * 1991-02-12 1994-01-18 Ciba-Geigy Corporation 5-sulfonyl-substituted benzotriazole UV-absorbers
US5962683A (en) * 1996-06-28 1999-10-05 Ciba Specialty Chemicals Corp. Oxazoline compounds as stabilizers
US6166218A (en) * 1996-11-07 2000-12-26 Ciba Specialty Chemicals Corporation Benzotriazole UV absorbers having enhanced durability
US5869554A (en) * 1997-09-02 1999-02-09 General Electric Company Polycarbonate compositions comprising hindered amine light stabilizers and ultraviolet light absorbers
JP2001516751A (en) * 1997-09-17 2001-10-02 チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド Morpholinone as a light stabilizer
US6380285B1 (en) * 2000-02-01 2002-04-30 Ciba Specialty Chemicals Corporation Bloom-resistant benzotriazole UV absorbers and compositions stabilized therewith

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO02079313A1 *

Also Published As

Publication number Publication date
JP2004523638A (en) 2004-08-05
WO2002079313A1 (en) 2002-10-10

Similar Documents

Publication Publication Date Title
US6905525B2 (en) Candle wax stabilized with piperazinones
AU777649B2 (en) Bloom-resistant benzotriazole UV absorbers and compositions stabilized therewith
US6740132B2 (en) Candle wax compositions stabilized with UV absorber-metal combinations
US6296674B1 (en) Candle wax stabilized with red-shift benzotriazoles
CA2346267A1 (en) Solid, shaped and colored wax articles
JP2004534009A (en) Benzotriazoles and their use as UV stabilizers
US6540795B2 (en) Candle wax stabilized with oxazolidines
JP2004525185A (en) Long-chain sterically hindered amines and compositions stabilized thereby
JP4767470B2 (en) Candle wax stabilized by a combination of UV absorber and selected hindered amine
US6544305B2 (en) Candle wax stabilized with piperazinones
US6562083B2 (en) Candle wax stabilized with s-triazines/hals
WO2002079313A1 (en) Stabilized candle wax
US6562084B2 (en) Candle wax stabilized with piperazindiones
US6544304B2 (en) Candle wax stabilized with morpholinones
US6547840B2 (en) Candle wax stabilized with imidazolidines

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20030901

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE TR

AX Request for extension of the european patent

Extension state: AL LT LV MK RO SI

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20060620