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    US7828957B2

    Uploaded by

    saeed talebian
    wax

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    © All Rights Reserved
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    'USO07S28957B2 2) United States Patent (10) Patent No: US 7,828,957 B2 ‘Yang et al. (45) Date of Patent: Nov. 9, 2010 (1) OLEFINWAXES HAVING IMPROVED .240795 4121980 enti HARDNESS OR VISCOSITY SShom a ‘e190 Reel 4426209 A 11984 Bolo tal (75) tnveaors: Mu Yang, 3123 Re Ridge Ct, Manel 610148 BL 1001 Deas ab TX (US) 77578; Eduardo J Baral, essa ats ater ae 382 Wildwood Valley Ct, Kingwood, area aes oe ce TX (US) 77345; Wille fsom, 2319 Eerineieiayall leaned: oe Pine Cone De, Kingwood, TX (US) eos AL 62005 Laonctal 77339; Ronald G Abbot, 3923 Laurel Rock Des Ringoond, TX (US) 77345 FORPIGN PATENT DOCUMENTS . ve sor 101964 (4) Note: Subjetio any disclaimer, theterm ofthis BE Lee patel is extended or adjusted under 38 Gp eines os USC. 1840) by 0 days oo Dox00d 9:4 oo soem 21) Appl.Nos 1RA3aH6 Wo woorsssss 112001 (22) Filed: Apes 27,2000 OTHER PUBLICATIONS ‘Wol“inferne of Meshal Propet rom stramented Dagth (6s) Prior Publication Data Scsing Indenaon a Tiny Loa and Indentation Dope" Cot : Ree Teco 354):37799 (0. eee “The Engineering Too! Box", Dynamic Absolute and Kinematic Visi yt 2001) Ratan eens ‘Publication No. 03167208, Patent Abstracts of Jan (Ju. 19, 1991), (63) Contimaton of aptication No, 11084794, fled ony ina y, Jan. 27, 2005, now Pat. No, 7,527,686, which is a ions ama ‘sninnaionin-pat of aplication No. 10996.331, Primary Exuminer—David M Brunsman fled oo Nov. 23,2004, nas Pat No. 7.341.619 6 AMSTRACT (1) Ic. co7C 3712200601) In one embodiment, we diselose hardened olefin wanes and Cost 9106 (2006001) processes for preparing them, In another embodiment, We comp 19176 (200601) {iacloae oxidized olefin wanes having low viscosity and pro- (2) US.C 208/3; 106/270. censes Tor preparing them. The waxes are suitable foe use 38 (58) Feld of Clasiiaton Search 106/270; polishes, coatings or inks, among ater uses. or example, a 2003 hardened lea wax composition produced from fesstock See application le for complete search history oft wax composton by eoning the felstock ein ‘wax composition wilh an oxyget-contining gas ate 66) References Cited Perature gener than a meling point ofthe feedstock olefin 32296 s3isuos U.S, PATENT DOCUMENTS 1965 41967 21972 Evans ea = 81975 Michel ea 31976. Ehehan ta 111976 Bienvens 1977 Bienvent 121979. Bienen eal Phitips et. Fag 20833 ‘wax composition, the hardened defn wax composition b= ‘ng: # needle penetration value at 25°C. at least 5 percent less than a needle penetration value at 25° C, of the fesstock olefin wax composition; a kinematie viscosity at 100° C. of ‘up fo about 200% greater than the kinematic viseosity ofthe eedstock oelin wax composition; and saponification um ber less than S mg KOH/g hardened olefin wax composition 20 Claims, No Drawings US 7,828,957 B2 1 OLEFIN WAXES HAVING IMPROVED. HARDNESS OR VISCOSITY, (CROSS REFERENCE TO RELATED "APPLICATIONS, The present application is a continuation application of US. patent application Ser. No, 11/045,794 filed on Jan. 27 2005, which is entitled “Olefin Waxes Having Improved Hardness or Viscosity" now U.S. Pa. No. 7,527,686 and isa ‘continvationin-part of U.S. patent application Ser. No, 10/996,331 fled Nov. 23, 2004 now US. Pat. No. 7341,619. US. patent application Ser. No. 10!996,331 is hereby incor porated herein by reference in its entirety for all purposes. BACKGROUND OF THE INVENTION ‘The present invention relates generally to the felds of alpha olefin waxes. More particularly itconcems alpha olefin wax composition having high hardness, or oxidized alpha ‘olefin wax compositions having low viscosity Hydrocarbon waxes, such a alpha olefin wanes, parafin waxes, microcrystalline waxes, polyethylene waxes, and Fisher-Tropseh waxes, are characterized by a set of basic physical property parameters, which are used to predict or ‘correlate performance in specific applications, The most ‘commonly eited wax physical properties are hardness, rap, melting point and viscosity. For most wax products, these fundamental properties are goveried by the molecular weight. As elatively low molecular weight waxes, alpha ole- fin (AO) wanes are relatively soft but have desirable high melt low stemming from their low molecular weight. On the ‘lhe hand, extremely hard waxes, such as polyethylene ‘wanes, have desirable high physical strength, but thei vi hardened wax composition is at feast 40 percent les than the needle penetration of the olefin wax eomposition. In sill a further embodiment, the necdle penetration of the additive- hardened wax composition is at east 0 percent les than the 0 o 4 needle penetration valve ofthe olefin wax composition ‘general and as the skilled artisan will be aware, the absolute valueof the needle penetration of the olefin wax composition, And the absolute rection ofthe needle penetration asaresalt ‘ofthe additive may depend on the specific eomposition ofthe flefin wax composition. “The aditive-hardened wax composition may'havea higher 4érop melt point than the olefin wax composition. Unless explicitly stated odherwise, all drop melt points refered 10 herein are measured according 10 ASTM D127. In one embodiment, the drop melt point of the additive-hardencd ‘wax composition isa last 25 percent grater than the deop pelt point of the olefin wax composition Ina futher embod ‘meal, the drop melt point of the sdditive hardened wax com- positon is atleast $0 percent greater than the drop melt point ‘ofthe olefin wax composition. In still a further embodiment, thedropmelt point of theaxditive-handened wax composition js at least 75 percent greater than the drop melt point of the olefin wax composition. Inyeta further embodiment, the dop ‘elt point of the adlitive-hardened wax composition is at Jeast 100 percent greater than the drop melt point ofthe olefin wax composition. Hardened Olefin Wax Compositions a another embodiment, the present invention relates ta hardened olefin wax composition, produced by a process comprising contacting a feedstock olefin wax composition ‘with an oxygen-containing gas ata temperature grester than the feedstock olefin wax composition melting point. In ‘another embodiment, the present invention relates toa bard- ened olefin wax composition, produced by a process compe! ing contacting # fecdstock olelin wax composition with an ‘oxygen-containing gas ata temperature greater than the feed ‘stock olefin wax composition meting point wherein the hard- enedolein wax composition has aneele penetration value at 25°C east 5 pereent les than the needle penetration valve 25°C. ofthe Feedstock olefin wax composition. In another embodiment, the present invention relates toa hardened ole- sin wax composition, produced by a process comprising con- tacting a feedstock olefin wax composition comprising aa olefin having at least 20 carbon atoms with an oxygen-con- taining gas at a temperature greater than the feedstock olefin wax composition meling point wherein the hardened olefin wax composition has a needle penetration value at 25° C. at east 5 percent less than the needle penetration value at 25°C. of the feedstock olefin wax composition. Additonal process steps and olefin wax product properties that may he used 10 further deseribe the hardened olefia wax composition are described herein. The feedstock olefin wax compositions ‘which can be used in the process steps are furher desribed herein. ‘The hardened olefin wax composition may also be described using additional qualitative and quantitative tests Por example, the hardened olefin wax composition may be defined by one or more of absolute needle penetration value, ‘elativencele penetration value, acid number, saponification ‘umber, Kinematic viscosity, of color, among others. Acid ‘number values when refered herein, are measured accord- ing to ASTM D 974, unless explicitly stated to the contrary All ssponfication numbers described herein are measred by ‘ASTM DS4, unless explicitly stated to the contrary. All kine- atic viscosities are the 100° C. Kinematic viscosities as ‘measured by ASTM D448, unless explicitly stated to the ‘contrary. All ASTM standards refered to herein ae the most csurtent versions as ofthe filing date the present application. Generally, the hardened olefin wax composition has 3 needle penetration vale st 25° C, at east 5 percent less than US 7,828,957 B2 5 the needle penetration vale at 25° C. ofthe feedstock ole wax composition. In one embodiment, the hardened olefin wax composition has a needle penetration at least 10 percent Jess than the nesdle penetration ofthe feedstock olefin wax ‘composition, In a further embodiment, the hardened olefin ‘wax composition has a needle penetration atleast 20 percent Jess than the needle penetration ofthe feedstock olefin wax ‘composition Instill further embodiment, the hardened ole fin wax composition has @ needle penetration at last 30 percent les than the needle penetration of the feedstock ole- {in wax composition. In yet a further embodiment, the hard- ‘ened olefin wax compesition as a needle peneiation atleast 40 percent less than the needle penetration of the feedstock ‘olefin wax composition. In stil further embodiment, the hardened olefin wax composition has a needle penetration at least 50 percent less than the needle penetration of the feed- stock olefin wax composition ‘Quunttatively, the hurdened olefin wax composition ean have an acid numberof less than about 12 mg KOH/g hard- ‘ened olefin wax composition. In one embodiment, the hard- 2 ‘ened olefin wx composition can have an acid number less than about 10 mg KOH/ hardened olefin wax composition. Ina further embodiment, the hardened olefin wax composi- tion ean have an acid number less than about 5 mg KOU g hardened olefin wax composition. In still a further embod ‘ment, the hardened olefin wax composition ean have an acid ‘number Jess than about 2:mg KOH/g hardened olefin wax ‘composition. In yeta futher embodiment, the hardened ole fin wax composition can have an acid number less than about Img KOH/g hardened olefin wax composition, ‘Also quantitatively, the hardened olefin wax composition ‘can have a saponification numberof less than about 45 mg. KOlig hardened olefin wax composition. In one further ‘embodiment, the hardened olefin Wax composition has 8 ‘sponification number less than about 25 mg KOH hard- ‘ened olefin wax composition. In sila luther embodiment, the hardened olefin wax composition has @ saponification number fess than about 15 mg KOHig hardened olefin wax ‘composition. In yeta further embodiment, the hardened ole fin wax composition has a saponification number less than about 10 mg KOIg hardened olefin wax composition. In ‘even further embodiment, the hardened olefin Wax compo= fition has @ ssponification number less that about 5 mg KOH hardenedoletin wax composition, Inanother embed ‘ment, the hardened olefin wax composition hus a saponifica- tion number less than about 2.5 mg KOH/g hantened ofefin wax composition ‘Also quantitatively, the hardened olefin wax composition ‘ean havea kinematie viscosity up to about 500% greater than the kinematic viscosity ofthe feedstock olefin wax composi- tion. In one further embodiment, the hardened olefin wax ‘composition has a kinematic viscosity up to about 300% treater than the kinematic viscosity ofthe feedstock olefin ‘vax composition. Insti a further embodiment, the hardened ‘olefin wax composition has a Kinematic viscosity up to about 200% greater than the kinematic viscosity of the feedstock ‘olefin wax composition. In yet a farther embodiment, the hardened olefin vx composition has a kineniaie viscosity upto about 150% wreater than the kinematic viscosity ofthe {aedstock olefin wax composition. In even a further embodi- ment, the hardened olefin wax composition has a kinematic viscosity up to abowt 100% grestr than the kinematic viseos- fay ofthe feedstock olefin Wax composition. In ven sill & further embodiment, the hardened olefin wax composition has kinematic viscosity thats substantially unchanged rela- tive to the kinematic viscosity of the feedstock olefin wax ‘composition. By “substantially unchanged kinematic viseos- 0 o 6 ty” is meant the kinematic viscosity is up to about 30% arcater than the kinematic viscosity ofthe feedstock olefia wax composition. "Also quantitatively, the hardened olefin wax composition «ean havea drop melt point substantially unchanged relative 0 the drop melt point ofthe feedstock olefin wax composition ‘By “substantially unchanged drop melt point” is meant the drop melt point of the bardencd olefin wax composition is {rom about 10% less than te drop melt point of the feedstock olefin wax composition to about 10% greater than the drop ‘melt point ofthe feedstock olefin wax composition, ‘Quulitatvely, he hardened olefin wax composition gener- ally retains its white color. However, the invention encom- passes hardened olefin wax composition colors ranging from ‘white to light yellow: Though the process of preparing the hardened olefin wax. composition having a reduced noodle penetration relative 10 the feedstock olefin war composition involves contacting the eedstock olefin wax composition with an oxygen-containing 20s ithas been discovered that conditions used w produce the hardened olefin wax composition described herein do. not always significantly oxidize the olefin wax composition. Spe- cifically, the law aid numbers and lowe saponification m= bers observed for some embodiments ofthe hardened olefin ‘wax composition indicate that a significant portion of the ‘eedstock olefin wax composition is not oxidize. Thus, the Fhardened olefin wax composition may altematively. be described in terms of physical properties ofthe fesistock ‘olefin wax composition which do not change significantly as a result ofthe oxygen-containing gas contact stp in combi ‘ation with properties of the hardened olefin wax compos tion properties Which difer significantly from the properties of the feedstock olefin vax composition as result of the ‘oxygen-containing gas contact step. Examples ofthe feed- ‘stock olefin wax composition properies which do not change significantly asa result of the oxygen-containing was contact step and which may be used either singly on combination to eseribe the hardened olefin wax composition inchnde feed- stock olefin wax composition avenge molecular weight, averoge olefin molecular weight, feedstock olefin wax com- Position earbon number composition, or feedstock olefin wax defn composition, among others. Examples of the hardened lefn war composition properties which may differ measur ably from the properties ofthe feedstock olefin wax compa sition as a result of the oxygen-containing gas contact step and which may be used ether singly orn any combination to ‘eseribe the hardened olefin wax composition include needle penetration, viscosity, drop melt point, acid number, and Ssponification number, among others. Ths, a combination of the feedstock olefin wax composition properties that do not change significantly dae t contact withthe oxygen-contain- ‘ng as eontact sep an properties which may dfler messur- ahly due to contact with the oxy gea-contsiing gus may be ‘sed to describe the hardened olefin wax composition. For ‘example, in one non-limiting exemplary hardened olefin wax ‘composition, the hardened olefin wex composition has an average molecular weight substantially the same as the feed stock olefin wax composition and a needle penetration S percent less than the needle penetration ofthe feedstock ole- jin wax composition. In second non-limiting example of hardened olefin wax composition, the hardened olefin wax ‘composition comprises an olefin wax having an average ole- fin molecular weight from 260 grams/mole to 340 grams! ‘mole anda needle penetration 30 percent less than the needle penetration ofthe Feedstock olefin wax composition, Tone embodiment, the present vention relates toa han ened olefin wax composition having an average olelia US 7,828,957 B2 7 ‘molecular weight between 260 grams/mole and 340 grams! mole and a necdle penetration value less than 100 dim. ‘When refering to bardened olefin wax compositions, the term “average olefin molecular weight” refers to the average ‘molecular weight forall olefins inthe hardened olefin wax ‘composition Inher embostiments, the hardened olefin wax ‘composition having an average olefin molecular weight, between 260 gramsimole and 340 grams/mole has a needle penetration ess than 90 dmm,altematively less than 80 dm, (ernatvely less than 70 don, and alternatively less than 60 ‘dm. In another embodiment, the hardened olefin wax compo- sition has an average olefin molecular weight between 280 zrams'mole and 320 grams/mole and a needle penetration ‘valueless than 100mm. nother embodiments, thehardened olefin wax composition having an average olefin moleculae ‘weight between 280 gramslmole and 320 gramsmole has 2 needle penetration less than 90 dmm, alternatively less than 80 dmim, alteratively less than 70 dmm, and alternatively Jess than 60 dma, ‘In another embodiment, the hardened olefin wax compo= sition has an average olefin molecular weight between 290 ‘grimsimole and 310 gramw/mole and a needle penetration valueless than 100 dmm. Inher embodiments, thehardened ‘olefin wax composition having an average olefin molecular ‘weight between 290 grams/mole ad 310 grams/mole hs @ noadle penetration less than 90 dm, alternatively less than 80 dun, alteratively less than 70 dmm, and alternatively Jess than 60 dm. ‘The hardened olefin wax composition may also have an id number, saponification number, color or combination of these as described shove, nome embodiment, the present invention relatesto a har ‘ened olefin wax composition having an average olefi ‘molecular weight between 330 grams/mole and 420 grams! mole and a needle penetation Value less than 35 dm. Ia ‘ther embodiments, the hardened olefin wax composition having an average olefin molocular weight berwoen 330 _grims/mole and 420 gramsimole as needle penetration less than 30 dm, altematively Tess than 25 dmm, and alterna tively fess than 20 des, In another embodiment, the hardened olefin wax compo= sition has an average olefin molecular weight between 350 srams/mole and 400 grams/mole and a needle penetstion Value less than 3S din. In other embodiments, the hardened ‘olefin wax composition having an average olefin molecular ‘weight betwen 350 grams/mole andl 400 grams/mole has @ noadle penetration less than 30 dm, alternatively less than 25 dmm, and altematively less than 20 dma. In another futher embodiment, the hardened olefin wax. ‘composition has an average olefin molecular weight between, 360 grams/mole and 390 gramsiniole and noodle penetra- tion value less than 3$ dmm. In other embodiments, dhe hardened olefin wax composition having an average olefin ‘molecular weight between 360 grams/mote and 390 grams! ‘mole has a needle penetration less than 30 dm, alternatively Jess than 25 dm, and altematvely’ Tess than 20 dram Independently, the hardened olefin wax composition hav= ing an average oletin molecnlar weight between 330 grams) ‘mole and 420 grams per mole ean havea kinematic viscosity between about 3 eStand about 15 eS; in a further embed rent, botwoen about 3.5 eStand about 12S; instilla furor ‘embevdiment, htween about 3.5 eSt and about 8 St; in yet a funher embodiment, tween about 3.75 eStand about 6 St. Independently. the hardened olefin wax composition having an average olefin molecular weight htween 350 grams/mole ‘and 400 grams per mole ean have a Kinematic viscosity 0 o 8 between about 3 eSt and about 15 eSt in a further embod meat, between about 3.5 cStand about 12cStinstillafurher embodiment, between about 3.5 eStand about &eSI; in yet a further embodiment, between about 3.75 eStand about 6 eSt Independently, the hardened olefin wax composition having an avemge olefin molecular weight htwoen 360 grams'mole ‘and 390 grams per mole can have a kinematic viscosity between about 3 eSt and about 15 eSt in a further embod meat, berween about 3.5 cSt and about 12eSt;instilla further ‘embodiment, between about 3.5 eSt and about 8 cSt: in yeta Turther embodiment, between sbout 3.75 eStand about 6 eS. Independently. the hardened olefin wax composition having ‘an average olefin moleculae weight berwoen 330 grams/mole ‘and 420 grams per mol, alleratively between 350 grams! ‘mole and 400 gram/mole, and alternatively between 360 grams/mole and 390 prams/mole can have a drop melt poi between shout 50° C.and about 70° C. The hardened olefin ‘wax composition may also have an acid number, saponifica- ‘ion number, color or any combination ofthese as described hove. ‘none embodiment, the present invention relates toa har ened olefin wax composition having an average olefin ‘molecular weight hetween 440 grams/mole and $50 grams! ‘mole and 2 needle penetration value less than 10 dm. In other embodiments, the hardened olefin wax composition having an average olelia molecular weight between 440 srams/mole and $50 grams mole has a nesdlepenetraton ess ‘han 9 dun, altenatvely less than 7 dum, and alternatively Jess than $ dim, ‘Tn another embodiment, the hardened olefin wax compo- sition has an average olefin molecular weight between 460 sgrams/mole and S30 grams/mole and a needle penetration value less than 10 dnn. In other embodiments, the hardened olefin wax composition having an average olefin molecular ‘weight betwoon 460 grams/mole and 530 grams/mole has a needle penetration less than 9 dau, alternatively’ less than 7 «émm, and aematively less than $ dm. ‘Tn another embodiment, the hardened olefin wax compo- sition has an average olefin molecular weight between 480 agramsmole and 510 grams/mole and a needle penetration value less than 10 dan. In other embodiments, the hardened olefin wax composition having an average olefin molecular ‘weight betwoon 480 grams/mole and 510 grams/mole has a needle penetration less than 9 dau, alternatively’ less than 7 position mole % olefin compositions are not imited to olefins having at least 20 carbon atoms. The olefin mole % valves of the compositions may also be applied to the olefin wax com- position and feedstock olefin wax composition embodiments bhaving the olefin carbon number compositions and/or the verge olefin molecular weight ranges as deseribed herein, Tn some embodiments, the components of the olefin wax. ‘composition or feedstock olefin wax composition contains a paraffin wax in addition othe olefin wax. In further embod ‘mens, the olefin wax composition may contin paraffin wax ‘having greater than 20 carbon atoms. In yet Further embodi- ments, the olefin wax composition contains less than 65 mole % paralias baving preter than 20 carbon atoms: alterna- tively, 80 mole % parailins having greater than 20 earbon ‘toms; alternatively, 35 mole % paraffins having greater than 20 carbon atoms; altematvely, 20 mole % paraffins having ‘greater than 20 carbon atoms alternatively, § mole % paral- fins having greater than 20 carbon atoms; and alternatively, $ mole % paraffins having greater than 20 earbon atoms The olefin wax composition or feedstock olefin wax com> position mole % paraffin contents are not limited to olefi having at last 20 carbon atoms. The paraffin mole % values of the compositions may also be applied to same carbon ‘number compositions andor the average molecular weight ‘anges asthe olefin carbon number compositions andr the verge olefin molecular weight ranges described erin. Tnsome embodiments, the olefin wax composition or feed- stock olefin wax composition comprises alpha olefins. Inone embodiment, the olefin wax composition comprises preater than 30 mole®% alpha olefin having at lest 20 carbon atoms. Ina further embodiment, the olefin wax composition com: prises greater than 45 mole % alpha olefins having at lest 20 carbon atoms, In yet a farther embodiment, the olefin wax ‘composition comprises greater than 60 mole % alpha olefins hhavingatJeast20 carbon atoms. Instill a further embodiment, the olefin wax composition comprises greaterthan 7S mole % alpha olefins havingat lest 20carbon atoms, Ineven a further embodiment, the olefin wax composition comprises greater ‘han 90 mole®% alpha olefins having at least 20 carbon atoms. In even stil further embodiment, the olefin wax compos ‘ion comprises greater than 9S mole alpha olefins having at Teast 20 carbon atoms ‘The olefin wax composition oF feedstock olefin compos ‘ion wax alpha olefin compositions are not limited 1 olefins having atleast 20 carbon atoms. The alpha olefin mole % values ofthe compositions may also be applied tothe oefia ‘wax composition and feedstock olefin wax composition ‘embodiments having the olefin carbon number compositions nd the carbon number ranges and average olefin molec Jar weight ranges as deseribed herein “The olefin wax composition comprises olefins andlor alpha olefins with earhon number distributions, alpha olefin con- ‘ents, molecular weight distributions, and needle penetration values as deseribed herein, In one embodiment, the olefin wax composition or faed- stock olefin wax composition comprises grestr than 70.1% olefins having from 20 to 24 earbon atoms. In a further ‘embodiment, the olefin wax composition comprises greater than 80 wt % olefins having from 20 to 24 carbon atoms. in sila further embodiment, the olefin wax composition com: Drses greater than 85 wt % percent olefins having fom 20 to Décatbon atoms, la yeta further embodiment, the olefin wax US 7,828,957 B2 17 ‘composition comprises greater than 90 wt 9% olefins having from 20 0 24 carbon atoms. Instill afurher embodiment, the ‘olefin wax composition comprises ureater than 95 wi % ole fing having from 20 to 24 carbon atoms. Tn one embodiment, the olefin wax composition of feed stock olefin wax composition comprises greater than 5O wt % ‘olefins having fiom 24 to 28 carbon stoms. In a further ‘embodiment, the olefin wax composition comprises greater than 60 wi % olefins having from 24 t028 carbon atoms. Ina further embodiment, the olefin wax composition comprises anvater than 70 wt % olefins having from 24 to 28 carbon ‘loms, In yeta further embodiment, the olefin wa compost tion comprises greater than 80 wt % oletins having from 2410 2B carbon atoms, Instill further embodiment, the olefin wax ‘composition comprises greater than 90 wt % olefins having, trom 24 1 28 carbon atoms, In one embodiment, the olefin wax composition or fee: stock olefin wax composition comprises greater than 5O wt % ‘olefins having from 26 to 28 carbon stoms. In a furor ‘embodiment, the olefin wax composition comprises greater than 60 wt % olefins having from 26 t0 28 earbon atoms In@ further embodiment, the olefin wax composition comprises eater thant 70 wt 9% olefins having from 26 to 28 carbon, ‘atoms, In yet further embodiment, the olefin Wa composi tion comprises greater than 80 wt % olefins having from 2610 2B earbon atoms, Instill further embodiment, the olefin wax ‘composition comprises greater than 90 wt ®% olefins having from 26 0 28 earbon atoms Tn one embodiment, the olefin wax composition or feed stock olefin wax composition comprises greater than 70 wt % ‘olefins having atleast 30 carbon atoms. In a further exabodi ‘ment, the olefin wax composition comprises greater than $0 ‘vt olefins having at least 30 carbon atoms. In still a farther nbodiment, the olefin wax composition comprises greater than 85 wi % percent olefins having from atleast 30 carbon ‘toms, In yt further embodiment, the olefin wax compos! tion comprises greater than 90 wt % olefins having atleast 30 ‘carbon atoms. In still a further embocliment, the olefin wax. ‘composition comprises greater than 95 wt Ye coefins having at Jeast 30 carbon atoms, ‘Altematvely the olefin wax composition or feedstock ole- fin wax composition may be describe as an olefin wax com- position having a particular average molecular weight of the ‘olefin components thereof. In some embodiments, the olefin wax componition has an average olefin molecular weight rear than 260 prams/mole. In yet anather embodiment, the blefin wax composition has an average olefin molecular ‘weight greater than 330 grams/mole. In et another embod ment, the olefin wax composition has an average olefin molecular weight greater than 400 gramsmole. In othee ‘embodiments, the olelin wax composition hs an average ‘olefin molecular weight between 260 gramsimole and 340 prams/mole;altemuatively, between 280 gramsimole and 320 ‘arams/mole alternatively, betwoen 200 gramsimole and 310 zrams'mole. In another embodiment, the olefin wax compo- sition has an average olefin molecular weight between 330 zrams/mole and 420 grams‘nole: alternatively, between 350 srams/mole and 48 grams/mole; alternatively; between 360 rams/mole and 390 gramsmole. In yetanother embodimen the olefin wax composition has an average olefin molecular weight between 440 grams/mole and 550 grams!mole alter natively, between 460 gramsimoleand $30 grams/mole;alter natively, between 480 grams/mole and 510 grams/mole ‘Commetially avilable olefin waxes commonly contain 3 umber of alpha olefins having at east about 20 carbon ims, alpha olefins having atleast about 20 carbon atoms, as well as other compounds (smaller alpha olefins, smaller or- 0 o 18 val alpha olefins, internal olefins, vinylidene, or others) For example, Alpha Olefin Cop ¢ (Chevton Phillips Chemical Company LP, The Woodlands, Tex.) comprises from about 35-55 wi % Ca olefin, about 25-45 wt % C,, olefin, bout 10-26 w1%C,, olefin, about 3 wt S6olefns smaller than C,, and about 2 wt % olefins larger than Cy. Alpha Olefin C324 isanexemplary olefin wax within the definition “comprising an olefin having at least 20 carbon atoms" as used herein. The invention isnot limited to this or any other particular com- vercially availabe olefin wax. Also, anolefin wax consisting essentially of an olefin having 20 carbon atoms (or another olefin having @ particular number of carbon atoms greater than 20) can also be used in the present invention, Inone embodiment, the olefin wax composition comprises an olefin having from about 20 carbon atoms to about 24 carbon atoms. In another embodiment, the olefin Wax com- Position comprises an olefin having from about 26 carbon ‘toms 1 abou 28 carbon atoms. In yet another embodiment the olefin wax composition comprises an olefin having. from about 26 1 about 28 carbon atoms. In an adlitional embod ‘ment, the olefin wax composition comprises an olefin having at least 30 carbon atoms. Commercially available olefin waxes may further com- prise vinylidene or intemal olefins, upto as much as about '40-50wt % ofthe wax. In one embodiment, and regardless of ‘the numberof earbons in the olefin, the olefin wax i a high alpha (HA) AO wax. By “HA wax" is meant a wax compris- ing () one or more alpha olefins and (b) less than about 20 1W1% vinylidene or internal olefin. Independent, commercially available olefin wax compo sitions may’ further comprise non-olefin hydrocarbons, such asparafins (hydrocarbons wherein all bonds between carbon atoms ae single bonds). Other components known in the at to acceptably’ be present in olen waxes can be present as ‘well For example, some applicable olefin wax compositions andlor feedstock olefia wax composition may contain oxy ‘genated components such as alcobols, aldehydes, and Ketones, among others. Thus, oxygenated components may ‘ot impact the generally observed dacrease in the needle penetration of the hardened olefin wax compositions or the ‘oxidized olefin wax compositions deseribed herein, ‘Known olefin waxes include olefin steams from ethylene oligomerization, cracked heavy wanes (ep. Fischer-Tropsch waxes), and mixtures of paraffins and olefins, among others. Additionally, the olefin wax compositions andlor the feed ‘tock olefin wax compositions may include Fischer-Tropsch ‘waxes comprising a mixture of parallia waxes and olelia ‘waxes which moot the describe olefin wax composition and! or feedstock olefin wax compositions described herein. One Ssouree of commercially available Fischer-Tropsch wares is ‘aso, Johannesburg, South Africa TInsome embodiments, the olefin wax composition or fae stock olefin wax composition comprises commercially sv able normal alpha olefin waxes. In other embodiments, the olefin wax composition consist essentially of eommereally available normal alpha olefin waxes. One source of commer- cially available alpha olefin waxes is Chevron Philips Chemical Company LP, The Woodlands, Tex. The following fare published physical and chemical characteristics of the ‘normal alpha olefin waxes Alpha Olefin Cp 24, Alpha Olefin Covsae Alpha Olefin Cg ay pha Olefin Ca, and Alpha Olefin Cy, Which ae provided for ilustraive purposesas ‘exemplaty feedstock olefin waxes. The invention is ot im ited to these particular feedstock olefin waxes, US 7,828,957 B2 19 Chances Coon on Deep met paat“E las 12) itso te. Neste Beterton Qu Pada Sito Cater St Alp te SeVilenes Slr tine CNN Despre psi“ las 12 eet Pencrton rr Fenn Reale Bneion S10 Fed nie Fed DE ASIDE) 3 (HOSS) Hey 0 855) oe ise 10 » FahPoat Merk UNSC) SR ANC) {asi bs) ‘The following examples are included to demonstrate pre= {errd embodiments ofthe invention. I'should be appreciated by those of skill nthe ar tha the techniques disclosed in the ‘examples which follow represent technigues discovered by the inventors to funtion well in the practice of the invention. However, those of skillin the art shoul in ight ofthe present disclosure, appreciate that many changes can be made in the specific embodiments which are disclosed and stil obtain @ Tike or similar result without departing from the sprit and scope ofthe invention. Examples 1-8 relate to haedened olefin waxes, Example 1 500 gof normal alpha olefin wax C30s (Chevron Phillips ‘Chemical Company LP) was placed into a fourneck flask, which was equipped witha heating mantle, a thermocouple, 3 single blade agitator, an ar sparger (eylindrcal, 1" in length and "in diameter, average pore size 15 jum), and side am ‘connected Wo a receiving Mask. The wax was heated to 220°C. 400 pm. stream of air was then nrxtuced below the wax Tiquid at CFHL. The rection was ‘maintained t 220°C. for 30 min. The contents were allowed to cool to 100°C. and were discharged. The resulting material appeared as a white slid 20 Coe Crem Cone 12s (FR) 159 (S068) se) barn ss 428) sass) 40 5058) ATR AWE) AERA) GPE ARC) yw ma) 21065) 18 (DST) warn was ASN) ns tot 1 “ B ss ™ » ATR eC) ASR ARE) as aSTMDIRD Sipeniteaton Nunbcr.ng KONWASTMDSS) dt Mak Voy 10°C, <8 (ASTM D 5) Boo go Dap Mating Pint °C. (ASTID 1 Example 2 500 g of normal alpha olefin wars C30¢ (Chevron Pillps Chemical Company LP) was placed into a four-nock flask, ‘which was equipped witha heating mantle, a thermocouple, single blade agitator. an air spangr (eylindrcal, 1" in length ® and % indiameter, average pore size 1S ym), and aside arm ‘connected toa reveving flask. The wax was heated 10 220°C. and the agitation was set at 400 rpm. A stream of aie was thea introduced below the wax liquid at | CFH, The reaetion was 45 maintained at 220° C. for I hour. The contents were allowed tooo] 100°C. and were discharged. The resulting material appeared a. a white solid US 7,828,957 B2 2 Tape Preis conto ME inswpiseh Sprateson Number meRORECASTMDI —<0S 3S Hen ico tr Coes ast 85) Bows Dap Metin Put "C|ASTMD 127) * Example 3 500 g of normal alpha olefin wax C3O+H1A (Chevron Phil lips Chemical Company LP) was placed into a four-nock ask, which was equipped with a heating mantle, a theemo- ‘couple single blade agitator, an air sparger (cylindrical, 1" in eogth and 5" in diameter, average pore size 15 um), and a side arm connected toa feociving Hask, The wax was heated 10220? Cand the agitation was set at 400 ppm. A steam of ‘ax then introduced below the wax liquid at 1 CFH. The reaction was maintained at 20°C. for 30 min, The contents ‘were allowed to coo! 10 100° C. and were discharged. The resulting material appeared asa white solid 2 single blade agitator, and. side am connected to a receiving ask. The wax was heated to 220” C. and the agitation Was sot at 100 rpm. A stream of air was then introcaced above the Surface of wax liquid at 4 CPHL. The reaction was msintained 20°C for 3 hour. The contents wore allowed t0 600] 0 100" C. and wore discharged. The resulting material appeared Dropeice cones 8 Ei Nimo ne RO STM D7 S333 Example 6 500 g of normal alpha olefin ware C304H1A (Cheveoa Phi lips Chemical Company LP) was placed into a four-neck flask, which was equipped with a heating mantle, a thermo coup single blade agitator, anda sie arm connected 0 8 receiving ask. The wax was heated to 220° C. and the aie {ation Was seta 100 rpm. A seeam of aie wes then iteodueed above the surface of wax liquid at 4 eubie fet per hour. The Tragne reaction sax mntined 220° far hoor The contents epi coms Sere alowed to colo 100° C.and were daca The ener ST © eins mater! appeared sa white sot CSB Seen tinkemeROMECASTIIDD) —ropeiee comm 15 jasmpn2y Ad Naber, g KOH ASTM D974) 02 ‘Mek Von 10°, (ASTM Ds) ao Example 16 ‘500 g of normal alpha olefin wax C26/28 (Chevron Pillps (Chemical Company LP) was placed into a four-nock flask, ‘whieh was equipped witha heating mantle, a themocouple, 3 single blade agitator. an sir spanger (eylindrical 1" in length and" in diameter, average pore size 15 um)-and a side arm ‘connected toa receiving flask. The wax was ated 1 145°C and the agitation was stat 400 pm. Then a steady steam of fir as introduced at 3.4 CFH, The reaction was asinained fa 145° C. for 24 hours. The contents were allowed t e001 0 100° C. and were discharged. The resulting material appeared as ‘same Tape Prenice cont 8 Poets conn Tele Renan Nr Ge ss eee Seis um ag KOMEASTD SN) —

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