EP1383832A1 - Stabilisierter kerzenwachs - Google Patents

Stabilisierter kerzenwachs

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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Withdrawn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
English (en)
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
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 US09/824,048 external-priority patent/US6547840B2/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 US09/824,141 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/de
Withdrawn legal-status Critical Current

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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.

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  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
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EP02716843A 2001-04-02 2002-03-25 Stabilisierter kerzenwachs Withdrawn EP1383832A1 (de)

Applications Claiming Priority (11)

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

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EP1383832A1 true EP1383832A1 (de) 2004-01-28

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WO2007128672A1 (en) * 2006-05-03 2007-11-15 Ciba Holding Inc. Substituted hexahydro-1,4-diazepin-5-ones and compositions stabilized therewith
CA2812109A1 (en) 2010-09-20 2012-03-29 Kareus Therapeutics, Sa Methods and compositions for treatment of diabetes and dyslipidemia
WO2017146936A1 (en) 2016-02-26 2017-08-31 Exxonmobil Research And Engineering Company Coating compositions for oriented strand boards and associated methods of use

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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
MX214967B (es) * 1997-09-17 2003-06-26 Ciba Sc Holding Ag Morfolinas como estabilizantes de luz
US6380285B1 (en) * 2000-02-01 2002-04-30 Ciba Specialty Chemicals Corporation Bloom-resistant benzotriazole UV absorbers and compositions stabilized therewith

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