CA2199576C - Dual-cure latex compositions - Google Patents

Dual-cure latex compositions Download PDF

Info

Publication number: CA2199576C
Authority: CA; Canada
Prior art keywords: reactive functional; molecular weight; radiation; low molecular; epoxy
Prior art date: 1996-03-26
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.): Expired - Lifetime

Application number

CA 2199576

Other languages

English (en)

French (fr)

Other versions

CA2199576A1 (en

Inventor

Andrew Joseph Swartz

Kurt Arthur Wood

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.)

Rohm and Haas Co

Original Assignee

Rohm and Haas Co

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.)

1996-03-26

Filing date

1997-03-10

Publication date

2005-10-25

1997-03-10 Application filed by Rohm and Haas Co filed Critical Rohm and Haas Co

1997-09-26 Publication of CA2199576A1 publication Critical patent/CA2199576A1/en

2005-10-25 Application granted granted Critical

2005-10-25 Publication of CA2199576C publication Critical patent/CA2199576C/en

2017-03-10 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000004816 latex Substances 0.000 title claims abstract description 49
229920000126 latex Polymers 0.000 title claims abstract description 48
239000000203 mixture Substances 0.000 title claims abstract description 46
239000004593 Epoxy Substances 0.000 claims abstract description 26
125000000524 functional group Chemical group 0.000 claims abstract description 23
239000000758 substrate Substances 0.000 claims abstract description 18
238000000034 method Methods 0.000 claims abstract description 15
238000000576 coating method Methods 0.000 claims abstract description 14
229920005989 resin Polymers 0.000 claims abstract description 13
239000011347 resin Substances 0.000 claims abstract description 13
230000005855 radiation Effects 0.000 claims abstract description 12
230000007246 mechanism Effects 0.000 claims abstract description 11
150000003384 small molecules Chemical class 0.000 claims abstract description 11
238000009833 condensation Methods 0.000 claims abstract description 10
239000011248 coating agent Substances 0.000 claims abstract description 9
230000015572 biosynthetic process Effects 0.000 claims abstract description 6
239000006185 dispersion Substances 0.000 claims abstract description 6
230000000694 effects Effects 0.000 claims abstract description 5
239000011253 protective coating Substances 0.000 claims abstract description 3
125000001931 aliphatic group Chemical group 0.000 claims description 4
229920000647 polyepoxide Polymers 0.000 claims description 4
IDSLNGDJQFVDPQ-UHFFFAOYSA-N bis(7-oxabicyclo[4.1.0]heptan-4-yl) hexanedioate Chemical compound C1CC2OC2CC1OC(=O)CCCCC(=O)OC1CC2OC2CC1 IDSLNGDJQFVDPQ-UHFFFAOYSA-N 0.000 claims description 3
125000005417 glycidoxyalkyl group Chemical group 0.000 claims description 3
229920000642 polymer Polymers 0.000 description 25
239000002253 acid Substances 0.000 description 20
238000001723 curing Methods 0.000 description 16
150000001875 compounds Chemical class 0.000 description 12
239000007787 solid Substances 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
238000009472 formulation Methods 0.000 description 7
230000005494 condensation Effects 0.000 description 6
235000019441 ethanol Nutrition 0.000 description 6
239000002245 particle Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
125000000129 anionic group Chemical group 0.000 description 5
235000014113 dietary fatty acids Nutrition 0.000 description 5
239000000194 fatty acid Substances 0.000 description 5
229930195729 fatty acid Natural products 0.000 description 5
150000004665 fatty acids Chemical class 0.000 description 5
RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 4
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
-1 acrylic ester Chemical class 0.000 description 4
239000000853 adhesive Substances 0.000 description 4
230000001070 adhesive effect Effects 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
239000000976 ink Substances 0.000 description 4
239000000178 monomer Substances 0.000 description 4
229920005862 polyol Polymers 0.000 description 4
150000003077 polyols Chemical class 0.000 description 4
239000004094 surface-active agent Substances 0.000 description 4
239000002966 varnish Substances 0.000 description 4
239000002023 wood Substances 0.000 description 4
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
239000002585 base Substances 0.000 description 3
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
239000008199 coating composition Substances 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
150000002009 diols Chemical class 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
238000002156 mixing Methods 0.000 description 3
229920000728 polyester Polymers 0.000 description 3
229920001225 polyester resin Polymers 0.000 description 3
239000004645 polyester resin Substances 0.000 description 3
229920000570 polyether Polymers 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
239000004814 polyurethane Substances 0.000 description 3
229920002635 polyurethane Polymers 0.000 description 3
239000000047 product Substances 0.000 description 3
230000006641 stabilisation Effects 0.000 description 3
238000011105 stabilization Methods 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
241000167854 Bourreria succulenta Species 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
206010073306 Exposure to radiation Diseases 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
239000004721 Polyphenylene oxide Substances 0.000 description 2
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
239000008365 aqueous carrier Substances 0.000 description 2
ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
239000012965 benzophenone Substances 0.000 description 2
235000019693 cherries Nutrition 0.000 description 2
238000007334 copolymerization reaction Methods 0.000 description 2
239000006184 cosolvent Substances 0.000 description 2
238000004132 cross linking Methods 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
125000005442 diisocyanate group Chemical group 0.000 description 2
238000007720 emulsion polymerization reaction Methods 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
125000003700 epoxy group Chemical group 0.000 description 2
239000000945 filler Substances 0.000 description 2
238000009408 flooring Methods 0.000 description 2
239000012530 fluid Substances 0.000 description 2
239000001530 fumaric acid Substances 0.000 description 2
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
239000003999 initiator Substances 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
239000003973 paint Substances 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
239000000049 pigment Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920001228 polyisocyanate Polymers 0.000 description 2
239000005056 polyisocyanate Substances 0.000 description 2
150000007519 polyprotic acids Polymers 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000007639 printing Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000010420 shell particle Substances 0.000 description 2
230000035939 shock Effects 0.000 description 2
238000003860 storage Methods 0.000 description 2
239000000052 vinegar Substances 0.000 description 2
235000021419 vinegar Nutrition 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 1
PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
OIYTYGOUZOARSH-UHFFFAOYSA-N 4-methoxy-2-methylidene-4-oxobutanoic acid Chemical compound COC(=O)CC(=C)C(O)=O OIYTYGOUZOARSH-UHFFFAOYSA-N 0.000 description 1
BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
WIVTXBIFTLNVCZ-UHFFFAOYSA-N CC(=C)C(=O)OCCP(=O)=O Chemical compound CC(=C)C(=O)OCCP(=O)=O WIVTXBIFTLNVCZ-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
241000854350 Enicospilus group Species 0.000 description 1
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
NQSMEZJWJJVYOI-UHFFFAOYSA-N Methyl 2-benzoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 NQSMEZJWJJVYOI-UHFFFAOYSA-N 0.000 description 1
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920002396 Polyurea Polymers 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
244000028419 Styrax benzoin Species 0.000 description 1
235000000126 Styrax benzoin Nutrition 0.000 description 1
ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
235000008411 Sumatra benzointree Nutrition 0.000 description 1
206010057040 Temperature intolerance Diseases 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
238000003848 UV Light-Curing Methods 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical class CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
239000006096 absorbing agent Substances 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical group CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
150000008062 acetophenones Chemical class 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
238000013019 agitation Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229920000180 alkyd Polymers 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
150000008052 alkyl sulfonates Chemical class 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
229960002130 benzoin Drugs 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
150000008366 benzophenones Chemical class 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000003139 biocide Substances 0.000 description 1
CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000002131 composite material Substances 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
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239000007771 core particle Substances 0.000 description 1
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
230000006378 damage Effects 0.000 description 1
229960002887 deanol Drugs 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000012972 dimethylethanolamine Substances 0.000 description 1
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000012674 dispersion polymerization Methods 0.000 description 1
150000002019 disulfides Chemical class 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
238000010894 electron beam technology Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000000835 fiber Substances 0.000 description 1
210000004905 finger nail Anatomy 0.000 description 1
239000006260 foam Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
230000009477 glass transition Effects 0.000 description 1
235000019382 gum benzoic Nutrition 0.000 description 1
238000013007 heat curing Methods 0.000 description 1
230000008543 heat sensitivity Effects 0.000 description 1
ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical class CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000005865 ionizing radiation Effects 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
239000010985 leather Substances 0.000 description 1
239000000944 linseed oil Substances 0.000 description 1
235000021388 linseed oil Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
238000013008 moisture curing Methods 0.000 description 1
230000000877 morphologic effect Effects 0.000 description 1
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
229940117969 neopentyl glycol Drugs 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
150000002917 oxazolidines Chemical class 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
229920002120 photoresistant polymer Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000002243 precursor Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
238000004886 process control Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
238000003847 radiation curing Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
229920006009 resin backbone Polymers 0.000 description 1
238000007650 screen-printing Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000010802 sludge Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 1
229910000679 solder Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003440 styrenes Chemical class 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000003784 tall oil Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
239000012085 test solution Substances 0.000 description 1
UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
238000004448 titration Methods 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
229920003176 water-insoluble polymer Polymers 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229910052724 xenon Inorganic materials 0.000 description 1
FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1

Landscapes

Epoxy Resins (AREA)
Paints Or Removers (AREA)
Macromonomer-Based Addition Polymer (AREA)
Silicon Polymers (AREA)
Polyurethanes Or Polyureas (AREA)

CA 2199576 1996-03-26 1997-03-10 Dual-cure latex compositions Expired - Lifetime CA2199576C (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US1408096P	1996-03-26	1996-03-26
US60/014,080		1996-03-26

Publications (2)

Publication Number	Publication Date
CA2199576A1 CA2199576A1 (en)	1997-09-26
CA2199576C true CA2199576C (en)	2005-10-25

Family

ID=21763420

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2199576 Expired - Lifetime CA2199576C (en)	1996-03-26	1997-03-10	Dual-cure latex compositions

Country Status (3)

Country	Link
CA (1)	CA2199576C (id)
ID (1)	ID16371A (id)
TW (1)	TW343985B (id)

1997
- 1997-03-10 CA CA 2199576 patent/CA2199576C/en not_active Expired - Lifetime
- 1997-03-18 ID IDP970874A patent/ID16371A/id unknown
- 1997-06-07 TW TW086107889A patent/TW343985B/zh active

Also Published As

Publication number	Publication date
TW343985B (en)	1998-11-01
CA2199576A1 (en)	1997-09-26
ID16371A (id)	1997-09-25

Legal Events

Date	Code	Title	Description
2002-02-21	EEER	Examination request
2017-05-14	MKEX	Expiry	Effective date: 20170310

Publication	Publication Date	Title
EP0796905B1 (en)	2003-09-17	Dual-cure latex compositions
MXPA97001307A (en)	1998-04-01	Compositions of latex, double cur
US4180598A (en)	1979-12-25	Radiation-curable coating compositions and method of coating metal substrates therewith
CA2126833C (en)	1999-11-30	Coating process using radiation curable compositions
EP0739922B1 (fr)	2001-08-08	Compositions en poudre à base de polyesters cristallins contenant des groupes méthacrylyle terminaux
US6380279B1 (en)	2002-04-30	Powder compositions with semicrystalline polyester and amorphous polyester base containing terminal methacryloyl groups
DE3048823A1 (de)	1981-09-17	Mit uv-strahlung haertbare harzmasse und ihre verwendung
KR100392719B1 (ko)	2003-12-31	분말도료용결합제,이의제조방법및당해결합제를함유하는분말도료
US4130522A (en)	1978-12-19	Aqueous coating composition and process
GB2315754A (en)	1998-02-11	Curable acrylic polymer compositions and their preparation
CA2199576C (en)	2005-10-25	Dual-cure latex compositions
GB2117674A (en)	1983-10-19	Multicoat forming method
US4409376A (en)	1983-10-11	Novel diluents useful in preparing high solids coating compositions
JPS6118922B2 (id)	1986-05-15
JP2001151848A (ja)	2001-06-05	活性エネルギー線硬化性ウレタン組成物の製造方法
US5190994A (en)	1993-03-02	Aqueous dispersions of hybrid polymers and coating compositions containing same
JPH0570558A (ja)	1993-03-23	変性エポキシ樹脂及びそれを用いた硬化性樹脂組成物
JP2000336132A (ja)	2000-12-05	樹脂組成物、その硬化物
JP2002060470A (ja)	2002-02-26	感光性樹脂組成物
JPS61179232A (ja)	1986-08-11	活性エネルギ−線硬化型組成物
JPS61179231A (ja)	1986-08-11	活性エネルギ−線硬化型組成物
JPH0673146A (ja)	1994-03-15	硬化性樹脂組成物及びその硬化物
JPS609045B2 (ja)	1985-03-07	顔料分散性、接着性に優れた紫外線硬化型樹脂組成物
JPS5923568B2 (ja)	1984-06-02	光硬化性樹脂組成物
JPS603405B2 (ja)	1985-01-28	紫外線硬化型樹脂組成物