CA2085592A1 - Alkali metal organosulphonate catalyst containing thermosetting composition of a mixture of polyester and aminoplast resin - Google Patents
Alkali metal organosulphonate catalyst containing thermosetting composition of a mixture of polyester and aminoplast resinInfo
- Publication number
- CA2085592A1 CA2085592A1 CA002085592A CA2085592A CA2085592A1 CA 2085592 A1 CA2085592 A1 CA 2085592A1 CA 002085592 A CA002085592 A CA 002085592A CA 2085592 A CA2085592 A CA 2085592A CA 2085592 A1 CA2085592 A1 CA 2085592A1
- Authority
- CA
- Canada
- Prior art keywords
- composition
- alkali metal
- polyester
- aminoplast resin
- mixture
- 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.)
- Abandoned
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
- C09D11/104—Polyesters
Abstract
A thermosetting composition comprising a mixture of a thermosettable polyester and an aminoplast resin together with an alkali metal sulfonate. The composition may also contain a pigment and a reactive diluent. The composition is useful as a coating or ink.
Description
W O 92~00359 PCT/US91/03225 `~`.`i' Al~ali Metal Organosulphonate Catalyst Containing Thermosetting Composition of a M~xture of Polyester and Aminoplast Resin 2~8~92 BAckg_otlllt of the lnventloll Thls i~lvel~tlo~ relAres ~o thermo~settlng coRting compositions contA~nlng nt len~st n~ t-hrtrmosett~hle rolyester and an flmlnoplast resll~ tngr~hrtr wllh .~ cntnlyst thrtreEor com~rlsing An AlkAll metal or~,nno~s~llfnnnee~ l`hl~s invetleion nlso relntes to contings nnd lnks rr~rnr~l rrom ~llt~l~ r~t~ n~t~nl~ nk~ Ar~t ~ r~AIly ~Is~Eul fnr lml-~lllt l~r~ m~ lr~c ~ tt~ ~)(Pr cr~ t ~r)ln cnl~s, e~c~
I`l~r~rm--~rtl~ r~ ~0~ r~ t~ n~--s ItIn~s cn~ltnlnlnrt one or more t~hermtxser~t~nl)ltt l~nlye~qtems nntl An nmi~ltplAst resln Are well known l~
the prior .~rl~ l`y~ic~lly~ sucll rrlor are compo~sielons Are cured by means of ncld cA~.~Iy~sls Whrtn ~such comrosltlons flre lntended for use AS coAting~s or i~k~st one or more rl~ments are added and the r~Atnly~st nf Inlvltrsnl rholrrt l~s rArA toluene sulfollc Acld (nPTS~ ~ llowrtvr!l~ en~tlll~s Anrl lnks prer~red from such composltlrlls llnvrt sevornl rllsntlvAntnges: (n) tl~ey require relntlvely ll~ttl ~ctlv~elon trmrerAturest e~tt~ 170 - 200-C., thereby nece~sslt~tlng Illgll r~ulrtrgy costs Anrt relatlvely low printing speeds;
nnrt (b) the roml-o~slt:lrul~s ~re not thorougllly cross-linked, and exhibit relAtively poor resistance to abrasion and pasteurization (typic.~lly requ~rel for heer cont~iners~.
The dlsAdv~rltages of the prlor art composltions are overcome ~y use of An alkali metal sulonate as tlle activation catalyst. Not only does tlle Alknll metAI ~sulfonAte ~ermit the se of lower ActlvAtlon tem~er~tures, I-llt mnny of the Alknll metal sulfonates also possess excellellt disrersing properties, thus resultlng in better wettln~ of tlle rl ~,ment in tlle composition and thereby resultln~ in lmproved erAnsfernhillty of the coating or ink to the substrate, as well ~s imprnved flow properties.
DET~IL$ oE T~E INVENTION
The thermosettlng compositions of the pre~ent invention comprise A mlxture of at least one thermosettable polye~ter and an 208~392 Amlnorlfl~st re~sln togetler wltll an alkali metal sulfonate.
oly~sters CO~ St of the polyconden~sstlon products of -nlynrhoxyllr nci~l~s w~ nlyhylroxy nlcohols nnl will typlcnlly ~ y vn~ q Or ~,() to ~50, pre~ernbly 100 - 150, fl~S well as ncil valuR~ of ~ to 2(), I)refera~ly 5 ~ 15~ Typically, the ~olycari)o~yllc nc~l~s rml~loyed in prerarlng the polyescers wlll be allpll.~lc or nro~tl~ nc~ls S-CIt ns phthalic, lsopht~halic, ryromellltlc, ~er~ llc, ntllp~c, etc~ and many monocarboxylic ~clds (e.g~ pelargonlc, c~l)rolc, lauric, isostearlc, ben~.olc, ~tc~) ~In m:~y ~)e ~ lrl ~n m~kr t~ romrosltlon tougher an~l more Elexlble.
Tlle ~qelected nel~ nre conlencel wlth l-olyhydroxy alcohols StlC~
RS etl~ylene, I-roryle~le, lletllylene, llrrorylene or trimethylene glycols, pent~erythrltol, glycerol, etc. a~s well as monoalcohols~
For m~ny contlng arrl~cations, lt mAy be desirable to use a mixture oE polyesters, ln orler to `tallor` the flbrAsion reslqt~qnce, ~lexlblllty, v~sco~slty, etc~ to the deslred level.
T}e aminopl~st re~s~ll serve~q n~q the crossllnklng agent for the rolyestrr~ Amln-l~ln~ql: rr~qlll~q nre A clnss of thermosettlng reslns prepared by react~op, am~o or amldino amines with an aldehyde.
2n Slltn~le rencln~ s ~llelll-le tlrea, ethylele uren, melamlne, gtlanAmllles~ etc~ wlll, glyoxal, Eormaldehyde, acetaldehyde, etc~
The Rmlnoplast resln will typlcally have an alkoxy (preferably ~, methoxymethyl) content o~ 2 to 6 and A welght average molecular weiglt of 200 to 500, preferably 300 to 400~
The selected polyester(s) and aminoplast resln are mixed 80 as to result ln R polyester:amlnoplRst resln in the range of 1:1 to 10:1, preferably 2:1 to 5:1.
For the purpose of this inventlon, the thermally-actlvated catalyqt is an alkali metal organo~ulfonate. The alkali Metal may be sodium (preferred), potassium or lithium, while the organo group may contain 1 to 22, preferably 8 to 18 carbon atoms. The organo group may be straight or branched-chain aliphatic, aromatic or heterocyclic ln nature; preferably the organo group is slkyl or W O 92/00359 PCTtUS91/03225 ~ 208~92 alkaryl gro~lr contnillln~ 8 to 18 carbon atoms. The alkali mecal organ~s~llfol~nt~ ~.c generally utlllzed ln An amount of 0.5 to 10 wt~
a, preferahly 3 7 wc~ ~, based on the weight of t)~e composition.
For .oat~ p, pllrrn~qe~q~ ent In the amoullt of 20 to 60 wt.
mfly be ndcled ~o tl~e enmposltlon The dlluent may oe any liquid tl~at wlll dls~qolve thr polye~ter and aminoplast, e.~. alcohols, nromnt~. h~(lrocnrbons, e~qlers, ketotles, etc. 11l those lnstances where ~ colore<l contln~ cnmposition is deslred, A pi~ment wlll be 1~ nddetl. An~ pl~,mPn~ co~v~t lonnlly employed for CORtingS may be n~ tl~ ~ t~ r~ ml~o~elnl~c of t~\~ rres~ t~ve~tlon~ e pl~meo~ rnrrnl Iy eml~loyed In a~ amount of 5 to 60 wt, ~, based on the we~p,ht o~ the enmlu~slt~on~ Non-limltin~ examples oE
suitnl)le pir~mPn~s ~I~-Ie yellows such as Yellow 1, Yellow 3, Yellow 12, Yellow 1/~, Yrllow 17, Yellow 6S, Yellow 73, Yellow 7/~
15 nnd Yellow R3; ornn~e~q snh a~q Or~nge 5, Ornnge 13, Oran~e 16, Orange 36 and OranF~e ~fi; I~lues and greens such A9 Blue 15, Green 7 and Green 36; and reds such n.q Red 3, Red 1~, Red 22, Red 23, Red 38, Red /~, Re~ 52, Re(l ~, Red 57, Red 60 and Red 63.
For printing lnk purroses, the composieion desirably includes a 2Q diluent to control viscoslty and to assist in transferability of the ink to the substrate. rreferably, the diluent is one which is non-volatile At the desired curing temperature and is reactive with the components of the coating composition. Volatile, non-reactive diluents are undesirable from an environmental and safety point of view And nl~qo since t:hey leave buhbles or cracks in the coating as they evaporate or they may be trapped between the outer surface of the ink coating and the overprint varnish W)liC)l is typically added after the suhstrate has been imprinted. The diluent i9 typlCAlly used in an amount of 2 to 25 wt. ~, preferably 2 to 20 wt. ~, based 3Q on the welght of ehe coating composition. Examples of suitable reactive diluents include ethylene glycol, polypropylene glycol, butylene glycol, tridecyl alcohol, octyl alcohol, lauryl alcohol, octadecyl alcohol, octylene glycol, hexyl carbitol, and the ll~e.
The coating compositions are applied to the de~ired substrate by ~praying, alr knlfe, curtain coating, roller coating, dipplng, W O 92/00359 PCr/US9I/0322~
2~39~
bru~ling, wtping, etc. nn(l the coated substrRte is then cured at elevnee~ temrerR~ures. ]n the cn~e of ink~, it has been found that., the temrernt~lre re~nlre~l ~or cnrlnF" t~ e~ the nctivAtion temrern~.ure, rnnp,~s ~roln ~ho~It I3()^C~ t~o t55~C.
The following e~nmr]es shAll serve to i11userate the present invenelorl:
~ poIyester wns prer~recl by re~cting under nitrogQn, at A
temrern~lre ~r nl-nnl~ ?()~ , 3/l pnrt~ nE ~rimellielc anllydride with 8 pnrts nt ~III-rorylene glyeol nll~ IR pnrta o~ trl~lecyl ~I.co~lol~
~0 T~a poIyester wl~lch res~tlted hnd nn ncid vnlue o~ 10 to 20 and a hyclroxyl vnlne Or ~ r~ ~r~ Seventy-Five pnrt~ o~ tl~e polyester were ndmixe~l with 25 pnrts of he~Akl~methyoxymethyl melamine to form A clenr .solutlon~
To 100 g of the above solutlon were added 0~004 mo1e of each of the catnlysts lndicAted in Table I below. An aliquot of 2.6 mg W8S
placed in n stAinless steel sample holder and heated under nitrogen in n l)upont 910 DI~ferentlAI Scnnning Calorlmeter to 300-C~ at a rate of 10'C. per minute starting at room temperature.
~ TABLE I
20 SamDle No. Catalvst Activseion TemD... C.
1 None 154.3 2 PTSA 172.9 3 Dioctyl sodium su1fo succinnte 139.5 4 Sodlum, dodecylbenzene sulfonate 141.7 Disodium, m-ben2ene dlsulfonate 146.2 6 Sodlum, butyl-napthalene sulfonate 137.6 7 Potassium methsne sulfonate 153.5 2~8~a92 A~s mny he seen from TAble 1, Samples 3 - 6 are elearly ndvnntn~,eolts 1n resrect to tlle nctlv~tion temperature~ obeained wltll rTSA or nn cntAIyst. Sample 7, which is a less preerred c~tAly~st, ~lso exhlhlts ~n ~dvantage ovrr PTSA, but shows no slgnlflcAnt ndvnntnp,~ over no cAtnly~st. Ilowever, many types of polye~ster.s, e~srecl.~lly tho.se wltll hlgll Acid value~s, eannot be efEectlvely c~lred In the nb~sence of flcid catalysts.
I`l~r~rm--~rtl~ r~ ~0~ r~ t~ n~--s ItIn~s cn~ltnlnlnrt one or more t~hermtxser~t~nl)ltt l~nlye~qtems nntl An nmi~ltplAst resln Are well known l~
the prior .~rl~ l`y~ic~lly~ sucll rrlor are compo~sielons Are cured by means of ncld cA~.~Iy~sls Whrtn ~such comrosltlons flre lntended for use AS coAting~s or i~k~st one or more rl~ments are added and the r~Atnly~st nf Inlvltrsnl rholrrt l~s rArA toluene sulfollc Acld (nPTS~ ~ llowrtvr!l~ en~tlll~s Anrl lnks prer~red from such composltlrlls llnvrt sevornl rllsntlvAntnges: (n) tl~ey require relntlvely ll~ttl ~ctlv~elon trmrerAturest e~tt~ 170 - 200-C., thereby nece~sslt~tlng Illgll r~ulrtrgy costs Anrt relatlvely low printing speeds;
nnrt (b) the roml-o~slt:lrul~s ~re not thorougllly cross-linked, and exhibit relAtively poor resistance to abrasion and pasteurization (typic.~lly requ~rel for heer cont~iners~.
The dlsAdv~rltages of the prlor art composltions are overcome ~y use of An alkali metal sulonate as tlle activation catalyst. Not only does tlle Alknll metAI ~sulfonAte ~ermit the se of lower ActlvAtlon tem~er~tures, I-llt mnny of the Alknll metal sulfonates also possess excellellt disrersing properties, thus resultlng in better wettln~ of tlle rl ~,ment in tlle composition and thereby resultln~ in lmproved erAnsfernhillty of the coating or ink to the substrate, as well ~s imprnved flow properties.
DET~IL$ oE T~E INVENTION
The thermosettlng compositions of the pre~ent invention comprise A mlxture of at least one thermosettable polye~ter and an 208~392 Amlnorlfl~st re~sln togetler wltll an alkali metal sulfonate.
oly~sters CO~ St of the polyconden~sstlon products of -nlynrhoxyllr nci~l~s w~ nlyhylroxy nlcohols nnl will typlcnlly ~ y vn~ q Or ~,() to ~50, pre~ernbly 100 - 150, fl~S well as ncil valuR~ of ~ to 2(), I)refera~ly 5 ~ 15~ Typically, the ~olycari)o~yllc nc~l~s rml~loyed in prerarlng the polyescers wlll be allpll.~lc or nro~tl~ nc~ls S-CIt ns phthalic, lsopht~halic, ryromellltlc, ~er~ llc, ntllp~c, etc~ and many monocarboxylic ~clds (e.g~ pelargonlc, c~l)rolc, lauric, isostearlc, ben~.olc, ~tc~) ~In m:~y ~)e ~ lrl ~n m~kr t~ romrosltlon tougher an~l more Elexlble.
Tlle ~qelected nel~ nre conlencel wlth l-olyhydroxy alcohols StlC~
RS etl~ylene, I-roryle~le, lletllylene, llrrorylene or trimethylene glycols, pent~erythrltol, glycerol, etc. a~s well as monoalcohols~
For m~ny contlng arrl~cations, lt mAy be desirable to use a mixture oE polyesters, ln orler to `tallor` the flbrAsion reslqt~qnce, ~lexlblllty, v~sco~slty, etc~ to the deslred level.
T}e aminopl~st re~s~ll serve~q n~q the crossllnklng agent for the rolyestrr~ Amln-l~ln~ql: rr~qlll~q nre A clnss of thermosettlng reslns prepared by react~op, am~o or amldino amines with an aldehyde.
2n Slltn~le rencln~ s ~llelll-le tlrea, ethylele uren, melamlne, gtlanAmllles~ etc~ wlll, glyoxal, Eormaldehyde, acetaldehyde, etc~
The Rmlnoplast resln will typlcally have an alkoxy (preferably ~, methoxymethyl) content o~ 2 to 6 and A welght average molecular weiglt of 200 to 500, preferably 300 to 400~
The selected polyester(s) and aminoplast resln are mixed 80 as to result ln R polyester:amlnoplRst resln in the range of 1:1 to 10:1, preferably 2:1 to 5:1.
For the purpose of this inventlon, the thermally-actlvated catalyqt is an alkali metal organo~ulfonate. The alkali Metal may be sodium (preferred), potassium or lithium, while the organo group may contain 1 to 22, preferably 8 to 18 carbon atoms. The organo group may be straight or branched-chain aliphatic, aromatic or heterocyclic ln nature; preferably the organo group is slkyl or W O 92/00359 PCTtUS91/03225 ~ 208~92 alkaryl gro~lr contnillln~ 8 to 18 carbon atoms. The alkali mecal organ~s~llfol~nt~ ~.c generally utlllzed ln An amount of 0.5 to 10 wt~
a, preferahly 3 7 wc~ ~, based on the weight of t)~e composition.
For .oat~ p, pllrrn~qe~q~ ent In the amoullt of 20 to 60 wt.
mfly be ndcled ~o tl~e enmposltlon The dlluent may oe any liquid tl~at wlll dls~qolve thr polye~ter and aminoplast, e.~. alcohols, nromnt~. h~(lrocnrbons, e~qlers, ketotles, etc. 11l those lnstances where ~ colore<l contln~ cnmposition is deslred, A pi~ment wlll be 1~ nddetl. An~ pl~,mPn~ co~v~t lonnlly employed for CORtingS may be n~ tl~ ~ t~ r~ ml~o~elnl~c of t~\~ rres~ t~ve~tlon~ e pl~meo~ rnrrnl Iy eml~loyed In a~ amount of 5 to 60 wt, ~, based on the we~p,ht o~ the enmlu~slt~on~ Non-limltin~ examples oE
suitnl)le pir~mPn~s ~I~-Ie yellows such as Yellow 1, Yellow 3, Yellow 12, Yellow 1/~, Yrllow 17, Yellow 6S, Yellow 73, Yellow 7/~
15 nnd Yellow R3; ornn~e~q snh a~q Or~nge 5, Ornnge 13, Oran~e 16, Orange 36 and OranF~e ~fi; I~lues and greens such A9 Blue 15, Green 7 and Green 36; and reds such n.q Red 3, Red 1~, Red 22, Red 23, Red 38, Red /~, Re~ 52, Re(l ~, Red 57, Red 60 and Red 63.
For printing lnk purroses, the composieion desirably includes a 2Q diluent to control viscoslty and to assist in transferability of the ink to the substrate. rreferably, the diluent is one which is non-volatile At the desired curing temperature and is reactive with the components of the coating composition. Volatile, non-reactive diluents are undesirable from an environmental and safety point of view And nl~qo since t:hey leave buhbles or cracks in the coating as they evaporate or they may be trapped between the outer surface of the ink coating and the overprint varnish W)liC)l is typically added after the suhstrate has been imprinted. The diluent i9 typlCAlly used in an amount of 2 to 25 wt. ~, preferably 2 to 20 wt. ~, based 3Q on the welght of ehe coating composition. Examples of suitable reactive diluents include ethylene glycol, polypropylene glycol, butylene glycol, tridecyl alcohol, octyl alcohol, lauryl alcohol, octadecyl alcohol, octylene glycol, hexyl carbitol, and the ll~e.
The coating compositions are applied to the de~ired substrate by ~praying, alr knlfe, curtain coating, roller coating, dipplng, W O 92/00359 PCr/US9I/0322~
2~39~
bru~ling, wtping, etc. nn(l the coated substrRte is then cured at elevnee~ temrerR~ures. ]n the cn~e of ink~, it has been found that., the temrernt~lre re~nlre~l ~or cnrlnF" t~ e~ the nctivAtion temrern~.ure, rnnp,~s ~roln ~ho~It I3()^C~ t~o t55~C.
The following e~nmr]es shAll serve to i11userate the present invenelorl:
~ poIyester wns prer~recl by re~cting under nitrogQn, at A
temrern~lre ~r nl-nnl~ ?()~ , 3/l pnrt~ nE ~rimellielc anllydride with 8 pnrts nt ~III-rorylene glyeol nll~ IR pnrta o~ trl~lecyl ~I.co~lol~
~0 T~a poIyester wl~lch res~tlted hnd nn ncid vnlue o~ 10 to 20 and a hyclroxyl vnlne Or ~ r~ ~r~ Seventy-Five pnrt~ o~ tl~e polyester were ndmixe~l with 25 pnrts of he~Akl~methyoxymethyl melamine to form A clenr .solutlon~
To 100 g of the above solutlon were added 0~004 mo1e of each of the catnlysts lndicAted in Table I below. An aliquot of 2.6 mg W8S
placed in n stAinless steel sample holder and heated under nitrogen in n l)upont 910 DI~ferentlAI Scnnning Calorlmeter to 300-C~ at a rate of 10'C. per minute starting at room temperature.
~ TABLE I
20 SamDle No. Catalvst Activseion TemD... C.
1 None 154.3 2 PTSA 172.9 3 Dioctyl sodium su1fo succinnte 139.5 4 Sodlum, dodecylbenzene sulfonate 141.7 Disodium, m-ben2ene dlsulfonate 146.2 6 Sodlum, butyl-napthalene sulfonate 137.6 7 Potassium methsne sulfonate 153.5 2~8~a92 A~s mny he seen from TAble 1, Samples 3 - 6 are elearly ndvnntn~,eolts 1n resrect to tlle nctlv~tion temperature~ obeained wltll rTSA or nn cntAIyst. Sample 7, which is a less preerred c~tAly~st, ~lso exhlhlts ~n ~dvantage ovrr PTSA, but shows no slgnlflcAnt ndvnntnp,~ over no cAtnly~st. Ilowever, many types of polye~ster.s, e~srecl.~lly tho.se wltll hlgll Acid value~s, eannot be efEectlvely c~lred In the nb~sence of flcid catalysts.
Claims (10)
1. A thermosetting composition comprising:
(a) a mixture of At least one thermosettable polyester and an aminoplast resin; and (b) at least one alkali metal organosulfonate.
(a) a mixture of At least one thermosettable polyester and an aminoplast resin; and (b) at least one alkali metal organosulfonate.
2. The composition of claim 1 wherein the polyester has a hydroxy value of 40 to 250 and an acid value of 2 to 20.
3. The composition of claim 1 wherein the aminoplast resin has an alkoxy content of 1 to 15 and a weight average molecular weight of 200 to 500.
4. The composition of claim 3 wherein the resin has a methoxymethyl content of 2 to 6.
5. The composition of claim 1 wherein the alkali metal is sodium, potassium or lithium and the organo group contains 1 to 22 carbon atoms.
6. The composition of claim 5 wherein the organo group is a C8 - C18 alkyl group.
7. The composition of claim 1 wherein the ratio of polyester to aminoplast resin is in the range of 1:1 to 10:1.
8. The composition of claim 1 wherein the alkali metal organosulfonate is present in an amount of 5.0 to 10 wt. %, based on the weight of the composition.
9. The composition of claim 1 wherein a pigment is present in an amount of 5 to 60 wt. %, based on the weight of the composition.
10. The composition of claim 9 wherein a reactive diluent is present ] in an amount of 2 to 20 wt. %, based on the weight of t he composition.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/545,440 US5068273A (en) | 1990-06-27 | 1990-06-27 | Thermosetting composition |
| US545,440 | 1990-06-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2085592A1 true CA2085592A1 (en) | 1991-12-28 |
Family
ID=24176264
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002085592A Abandoned CA2085592A1 (en) | 1990-06-27 | 1991-05-09 | Alkali metal organosulphonate catalyst containing thermosetting composition of a mixture of polyester and aminoplast resin |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5068273A (en) |
| EP (1) | EP0536156A1 (en) |
| JP (1) | JPH05507513A (en) |
| CA (1) | CA2085592A1 (en) |
| FI (1) | FI925442A (en) |
| PT (1) | PT98127A (en) |
| WO (1) | WO1992000359A1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5312877A (en) * | 1993-02-12 | 1994-05-17 | Sun Chemical Corporation | High solids coating composition |
| US7829484B2 (en) * | 2005-11-22 | 2010-11-09 | Ciba Specialty Chemicals Corp. | Wettable polyester fibers and fabrics |
| EP3114164A4 (en) * | 2014-01-12 | 2017-12-27 | King Industries, Inc. | Lower temperature cure coating compositions |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2704750A (en) * | 1951-07-03 | 1955-03-22 | Sherwin Williams Co | Aminoplast resins |
| US3583941A (en) * | 1966-09-26 | 1971-06-08 | Celanese Corp | Linear polyester polymers containing alkali metal salts of sulfonated aliphatic compounds |
| US3592796A (en) * | 1969-03-10 | 1971-07-13 | Celanese Corp | Linear polyester polymers containing alkali metal salts of sulfonated aliphatic compounds |
| US3538057A (en) * | 1969-03-27 | 1970-11-03 | Fiber Industries Inc | Basic dyeable polyester polymers containing a metal salt of a cycloalkyl sulfonate |
| US4229555A (en) * | 1979-07-26 | 1980-10-21 | Mobil Oil Corporation | Linear polyester coil coating compositions |
| US4500680A (en) * | 1983-11-14 | 1985-02-19 | Ppg Industries, Inc. | Aromatic acid catalysts providing improved humidity resistance |
| US4501854A (en) * | 1983-11-14 | 1985-02-26 | Ppg Industries, Inc. | Aminoplast curable compositions containing disulfonic acid esters as latent acid catalysts |
| US4500689A (en) * | 1983-12-30 | 1985-02-19 | Westinghouse Electric Corp. | Low cost polyester modified phenolic resin containing a combination of long and short chain alkylphenols |
| US4783497A (en) * | 1985-12-16 | 1988-11-08 | Reynolds Metals Company | Water-based polyester coating compositions containing an alkylated amino resin |
-
1990
- 1990-06-27 US US07/545,440 patent/US5068273A/en not_active Expired - Fee Related
-
1991
- 1991-05-09 EP EP91909598A patent/EP0536156A1/en not_active Ceased
- 1991-05-09 WO PCT/US1991/003225 patent/WO1992000359A1/en not_active Application Discontinuation
- 1991-05-09 CA CA002085592A patent/CA2085592A1/en not_active Abandoned
- 1991-05-09 JP JP91509038A patent/JPH05507513A/en active Pending
- 1991-06-27 PT PT98127A patent/PT98127A/en not_active Application Discontinuation
-
1992
- 1992-11-30 FI FI925442A patent/FI925442A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO1992000359A1 (en) | 1992-01-09 |
| US5068273A (en) | 1991-11-26 |
| FI925442A0 (en) | 1992-11-30 |
| FI925442A (en) | 1992-11-30 |
| EP0536156A1 (en) | 1993-04-14 |
| PT98127A (en) | 1992-04-30 |
| JPH05507513A (en) | 1993-10-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 19970509 |