Styrenefree unsaturated polyester resin compositions.docx
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Styrenefree unsaturated polyester resin compositions.docx
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Styrenefreeunsaturatedpolyesterresincompositions
UnitedStatesPatent
7,396,882
Hewitt, etal.
July8,2008
Styrene-freeunsaturatedpolyesterresincompositions
Abstract
Styrene-freeunsaturatedpolyesterresincompositionsareprovidedwhichhavelowvolatileorganiccompoundsandhazardousairpollutantsemissionswhentheseresincompositionsareusedinopenmoldingapplications.Aprocessforthemanufactureoftheseresincompositionsisprovided.
Inventors:
Hewitt;JohnC.(Collierville,TN),McAlvin;JohnE.(Collierville,TN),Hutson;PaulTaylor(Memphis,TN),Craig;AmberE.(Collierville,TN),Krantz;Marjorie(Byhalia,MS),Rivers;DerekK.(Memphis,TN)
Assignee:
AOC,LLC(Collierville,TN)
Appl.No.:
10/440,610
Filed:
May19,2003
RelatedU.S.PatentDocuments
ApplicationNumber
FilingDate
PatentNumber
IssueDate
60382038
May.,2002
CurrentU.S.Class:
525/290;525/192;525/193;525/207;525/263;525/278;525/286;525/312;525/445;525/75;526/283;526/290
CurrentInternationalClass:
C07C13/61 (20060101);C08F299/02 (20060101);C08L67/07 (20060101)
FieldofSearch:
526/229,317.1,303.1,283,290525/290,75,278,445,312,263,286,192,193,207
ReferencesCited[ReferencedBy]
U.S.PatentDocuments
4390662
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4777209
October1988
Hefner,Jr.
5739240
April1998
Smith
5747597
May1998
Fujitaetal.
5773531
June1998
Smith
5908875
June1999
Smith
6037385
March2000
Smith
6277939
August2001
Smith
6468662
October2002
Nava
6646057
November2003
Andersetal.
6808821
October2004
Fujitaetal.
6884841
April2005
Nava
6992140
January2006
Kosonoetal.
PrimaryExaminer:
Gulakowski;Randy
AssistantExaminer:
Bernshteyn;MichaelM
Attorney,AgentorFirm:
BakerDonelsonBearmanCaldwell&BerkowitzPC
ParentCaseText
ThisapplicationclaimsthebenefitofU.S.ProvisionalApplicationSerialNo.60/382,038,filedMay20,2002.
Claims
Whatisclaimedis:
1.Astyrene-freeunsaturatedpolyesterresincompositionconsistingessentiallyof
(1)adicyclopentadiene-basedunsaturatedpolyester;
(2)aurethane(meth)acrylate;(3)amultifunctional(meth)acrylatemonomerand(4)from5-60percentbyweightofahydroxyl-functionalized(meth)acrylatemonomer,whereintheresincompositionaftercurehasaheatdistortiontemperature(ASTMD-648)ofatleast65.degree.C.
2.Aresincompositionasdefinedbyclaim1whereintheconcentrationoftheunsaturatedpolyesterisfrom15-70percentbyweight.
3.Aresincompositionasdefinedbyclaim1whereintheunsaturatedpolyesterhasaweightaveragemolecularweightof800-10,000.
4.Aresincompositionasdefinedbyclaim1whereintheunsaturatedpolyesteristhereactionproductofdicyclopentadienewithcompoundsofcarboxylicacidsand/oranhydridesandalcohols.
5.Aresincompositionasdefinedbyclaim1whereintheunsaturatedpolyesterismodifiedwithglycidylmethacrylateataleveluptoabout20percentbyweightoftheunsaturatedpolyester.
6.Aresincompositionasdefinedbyclaim1whereintheunsaturatedpolyesterismodifiedwithanallyletherfunctionalizedalcoholorepoxyataleveluptoabout20percentbyweightoftheunsaturatedpolyester.
7.Aresincompositionasdefinedbyclaim1whereintheconcentrationoftheurethane(meth)acrylateisfrom15-70percentbyweight.
8.Aresincompositionasdefinedbyclaim1whereintheurethane(meth)acrylateisareactionproductofahydroxyl-functionalized(meth)acrylatewithadiisocyanateorpolyiisocyanate.
9.Aresincompositionasdefinedbyclaim1whereintheconcentrationofthemultifunctional(meth)acrylateisfrom5-60percentbyweight.
10.Aresincompositionasdefinedbyclaim1thatcontainsuptoabout60percentbyweightofafiller.
11.Aresincompositionasdefinedbyclaim10whereinthefilleriscalciumcarbonate,calciumsulfate,aluminumtrihydrate,clayoracombinationthereof.
12.Aresincompositionasdefinedbyclaim1thatcontainsuptoabout5percentbyweightofathixotropicagent.
13.Aresincompositionasdefinedbyclaim12whereinthethixotropicagentisfumedsilica,organoclaysoracombinationthereof.
14.Aresincompositionasdefinedbyclaim1thatcontainsuptoabout2percentbyweightofabarrierformingagent.
15.Aresincompositionasdefinedbyclaim1thatiscuredwith1-3percentbyweightofadiacylperoxide,hydroperoxide,ketoneperoxide,peroxyester,peroxyketal,dialkylperoxide,alkylperester,percarbonate,azocompoundoracombinationthereof.
16.Aresincompositionasdefinedbyclaim1thatisformulatedwithaderivativeofaniline,anamide,anaromaticamineoranaliphaticamineataleveluptoabout1percentbyweight.
17.Aresincompositionasdefinedbyclaim1thatisformulatedwithacobaltcarboxylate,vanadium,potassium,zincorironcompoundataleveluptoabout1percentbyweight.
18.Aresincompositionasdefinedbyclaim1thataftercurehasatensilestrength(ASTMD-638)andtensilemodulus(ASTMD-638)ofatleast7,000psiand350,000psi,respectively.
19.Aresincompositionasdefinedbyclaim1thataftercurehasaflexuralstrength(ASTMD-790)andflexuralmodulus(ASTMD-790)ofatleast10,000psiand350,000psi,respectively.
20.Aresincompositionasdefinedbyclaim1thatcontainsatleasttwomultifunctional(meth)acrylatemonomers.
21.Aresincompositionasdefinedbyclaim1thatcontainsatleasttwohydroxyl-functionalized(meth)acrylatemonomers.
22.Aresincompositionasdefinedbyclaim14whereinthebarrierformingagentisaparaffin,polyester,polysiloxaneoracombinationthereof.
Description
TECHNICALFIELD
Thepresentinventionrelatestopolyesterresincompositions.Inamorespecificaspect,thisinventionrelatestostyrene-freeunsaturatedpolyesterresincompositions.
BACKGROUNDOFTHEINVENTION
Thermosetresins,includingunsaturatedpolyesters,arecommonlyemployedinavarietyoffabrications,suchascastingmaterials,fiberreinforcedmaterialsandcoatings.Unsaturatedpolyesterresinsmaybedefinedasthecondensationproductsofdicarboxylicacidsoranhydrideswithdifunctionalalcohols,typicallydissolvedinareactivediluentsuchasstyrene.Sincethecommercialinceptionofunsaturatedpolyesterresins,styrenehasbeenaprimaryreactivediluentduetoitslowcost,availability,easeofuseandresultingexcellentmechanicalproperties.However,inrecentyears,governmentregulationshaverestrictedstyreneemissionsinopenmoldingfacilitiesduetoharmfulenvironmentalandhealtheffects.
Anumberofalternativeshasbeensoughttoreduceemissionsandassubstitutesforstyrene.Highermolecularweightderivativesofstyrene,suchasvinyltolueneandt-butylstyrene,havebeenutilizedasreactivediluentsandresultedindecreasedemissions.However,emissionsarestillsignificantintheseresins,andsuchalternativestyreneanalogsarevolatileorganiccompounds.Theadditionofparaffinstounsaturatedpolyesterresinshasbeenshowntoreduceemissionsbyformingathinfilmontheresinsurface.Whilesuitableforsomeapplications,thissolutionisunacceptableforotherapplicationsduetoadecreasedinterlaminateadhesion.
Inmostcases,lowvolatileacrylateandmethacrylatemonomershavebeeninadequateasreplacementsforstyreneinunsaturatedpolyesterresinssinceatmosphericoxygenseverelyretardspolymerization,resultinginanunder-cured"tacky"surface.Furthermore,thepoorcopolymerizationofmostacrylatesandmethacrylateswithmaleateandfumaratemoietiesinthepolyesterbackboneoftenresultsininferiormechanicalpropertiescomparedtostyrenatedunsaturatedpolyesterresins.
Inthisapplication,theterm(meth)acrylatewillbeunderstoodtoincludebothacrylateandmethacrylatecompounds.
Previouspatentshavedescribednon-styrenatedunsaturatedpolyesterresincompositions.
U.S.Pat.No.5,747,597describesacurableresincomprisedofanunsaturatedpolyester,epoxymethacrylateand/orurethanemethacrylate,combinedwitholigoalkylether-monoalkoxymethacrylates.Theresinwasdescribedinmanycasestoairdry"dry-to-touch"aftertheadditionofwax,free-radicalinitiator,catalystandexposuretoelevatedtemperatures(130-145.degree.F.).Tensiletestingofthecastresinrevealedhighelongationandlowstrengthproperties,whichisinsharpcontrasttodatausingthesamepolymersdissolvedinstyrenethatdemonstratedconsiderablyhighertensilestrengths.
InternationalPatentPublicationNo.WO99/23122describestheuseofhydroxyethylmethylmethacrylate,hydroxyethylpropylmethacrylateand/orurethanehydroxyethylmethacrylatewithpolyestersandvinylesters.Theresultingtensileandflexuralpropertiesofthecuredproductswerecomparabletostyrenatedunsaturatedpolyesterresins,buttack-freecureinthinfilmsandthinlaminatestendstobeaproblemwiththeseresins.Additionally,basedonourevaluation,thestoragestabilityofresinsdescribedinthispublicationisverypoor.
AdditionalU.S.patentswhichdescribenon-styrenatedunsaturatedpolyesterresincompositionsareU.S.Pat.No.5,908,875,U.S.Pat.No.5,739,240,U.S.Pat.No.6,277,939,U.S.Pat.No.5,773,531andU.S.Pat.No.6,037,385.
Anongoinggoalintheunsaturatedpolyesterindustryhasbeentodevelopimprovednon-styrenated,free-radicalcurableresinswhichhaveprocessingsimilartocurrentstyrenatedresins,benefitsinmechanicalandphysicalpropertiesandtack-freecureinthinfilms.
SUMMARYOFTHEINVENTION
Brieflydescr
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