Candle wax stabilized with morpholinones

Details Candle wax stabilized with morpholinones Candle wax stabilized with morpholinones

2001-04-02

2003-04-08

Medley, Margaret (Department: 1714)

Fuel and related compositions

Candle composition

C431S288000

Reexamination Certificate

active

06544304

ABSTRACT:

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 in combination with a UV absorber and/or an antioxidant.
BACKGROUND OF THE INVENTION
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.
U.S. Pat. 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 Apr. 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-hydroxy-benzophenone 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).
U.S. Pat. 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-methoxy-benzylidinemalonate 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 U.S. Pat. Nos. 3,530,084; 4,379,721; 4,616,051 and 5,964,905 and in copending applications Ser. Nos. 09/495,495, 09/495,496 and 09/741,583.
U.S. Pat. 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.
U.S. Pat. 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.
U.S. Pat. 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.
None of these references teach the superior performance provided when the morpholinone compounds are used in conjunction with a UV absorber and/or antioxidant to stabilize candle wax.
OBJECTS OF THE INVENTION
The object of the invention is to provide for a white and unscented; white and scented; dyed and unscented; dyed and scented; dipped and unscented; or dipped and scented candle wax stabilized by a combination of a morpholinone compound with a UV absorber and/or antioxidant.
DETAILED DISCLOSURE
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) an effective stabilizing amount of a combination of
(i) a morpholinone compound containing a moiety of generic formula I
(ii) a UV absorber or an antioxidant, or a UV absorber and an antioxidant
wherein the ratio by weight of (i) to (ii) is from 10:1 to 1:10.
In another embodiment of the instant invention, the morpholinone compound of component (b)(i) is a compound of formula Ia or Ib
where
n is 1 or 2;
R
1
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
2
has the same meaning as R
1
; or R
2
is also hydroxyalkyl of 1 to 8 carbon atoms; or R
1
and R
2
together are tetramethylene, pentamethylene or pentamethylene substituted by methyl;
R
3
has the same meaning as R
1
;
R
4
has the same meaning as R
2
; or R
3
and R
4
together are tetramethylene, penta-methylene or pentamethylene substituted by methyl;
R
5
is hydrogen; alkyl of 1 to 18 carbon atoms; alkyl of 2 to 18 carbon atoms substituted by hydroxyl, 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; phenylalkyl of 7 to 12 carbon atoms; phenylalkyl 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 n is 1;
R
6
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
1
groups; or R
6
is phenyl;
when n is 2;
R
6
is alkylene of 2 to 12 carbon atoms, o-phenylene, m-phenylene, p-phenylene or p-xylylene; and
R
7
is hydrogen or has the meaning of R
1
.
Specific morpholinone compounds of formula Ia or Ib which are useful in the instant invention include
(a) 5-hydroxymethyl-3,3,5-trimethyl-2-morpholinone;
(b) 5-dodecanoyloxymethyl-3,3,5-trimethyl-2-morpholinone;
(c) 5-(2-ethylhexanoyloxymethyl)-3,3,5-trimethyl-2-morpholinone;
(d) 5,5′-bis(decandioyloxymethyl-3,3,5-trimethyl-2-morpholinone);
(e) N-(2,2,6,6-tetramethylpiperidin-4-yl)-tetrahydro-1,4-oxazin-2-one;
(f) N-(1,2,2,6,6-pentamethylpiperidin-4-yl)-tetrahydro-6-methyl-1,4-oxazin-2-one;
(g) N-(1-acetyl-2,2,6,6-tetramethylpiperidin-4-yl)-3-n-tetradecy

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