CA2040167C - Compositions thermodurcissables, composes de carboxyl a agent de durcissement inhibe et methodes de preparation desdits produits - Google Patents

Compositions thermodurcissables, composes de carboxyl a agent de durcissement inhibe et methodes de preparation desdits produits

Info

Publication number: CA2040167C
Authority: CA; Canada
Prior art keywords: compound; group; acid; good good; thermal latent
Prior art date: 1990-04-10
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

CA002040167A

Other languages

English (en)

Other versions

CA2040167A1 (fr

Inventor

Masahiro Ishidoya

Kishio Shibato

Keiji Komoto

Kenji Shibamoto

Mitsuyuki Mashita

Osamu Ohe

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.)

NOF Corp

Original Assignee

Nippon Oil and Fats Co Ltd

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.)

1990-04-10

Filing date

1991-04-10

Publication date

1997-12-16

1991-04-10 Application filed by Nippon Oil and Fats Co Ltd filed Critical Nippon Oil and Fats Co Ltd

1991-10-11 Publication of CA2040167A1 publication Critical patent/CA2040167A1/fr

1997-12-16 Application granted granted Critical

1997-12-16 Publication of CA2040167C publication Critical patent/CA2040167C/fr

2011-04-10 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 146
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 title claims abstract description 67
229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 45
238000002360 preparation method Methods 0.000 title claims description 84
238000000034 method Methods 0.000 title claims description 46
150000001875 compounds Chemical class 0.000 claims abstract description 340
-1 vinyl ether compound Chemical class 0.000 claims abstract description 107
125000000524 functional group Chemical group 0.000 claims abstract description 84
238000010438 heat treatment Methods 0.000 claims abstract description 34
239000000126 substance Substances 0.000 claims abstract description 26
125000005842 heteroatom Chemical group 0.000 claims abstract description 19
229910052717 sulfur Inorganic materials 0.000 claims abstract description 17
UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical compound C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 claims abstract description 12
239000002253 acid Substances 0.000 claims description 124
239000003377 acid catalyst Substances 0.000 claims description 41
238000006243 chemical reaction Methods 0.000 claims description 41
150000002148 esters Chemical class 0.000 claims description 34
125000004432 carbon atom Chemical group C* 0.000 claims description 33
125000003700 epoxy group Chemical group 0.000 claims description 32
238000002156 mixing Methods 0.000 claims description 28
125000000962 organic group Chemical group 0.000 claims description 26
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 21
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 18
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 14
125000000623 heterocyclic group Chemical group 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
125000004430 oxygen atom Chemical group O* 0.000 claims description 14
125000004434 sulfur atom Chemical group 0.000 claims description 13
229920005862 polyol Polymers 0.000 claims description 12
150000003077 polyols Chemical class 0.000 claims description 11
238000004132 cross linking Methods 0.000 claims description 10
239000004645 polyester resin Substances 0.000 claims description 9
229920001225 polyester resin Polymers 0.000 claims description 9
239000002841 Lewis acid Substances 0.000 claims description 8
150000001413 amino acids Chemical class 0.000 claims description 8
150000007517 lewis acids Chemical class 0.000 claims description 8
230000003472 neutralizing effect Effects 0.000 claims description 8
239000005056 polyisocyanate Substances 0.000 claims description 8
229920001228 polyisocyanate Polymers 0.000 claims description 8
150000008065 acid anhydrides Chemical class 0.000 claims description 7
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 7
125000001841 imino group Chemical group [H]N=* 0.000 claims description 7
125000005372 silanol group Chemical group 0.000 claims description 7
239000002879 Lewis base Substances 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 6
150000007527 lewis bases Chemical class 0.000 claims description 6
229910019142 PO4 Inorganic materials 0.000 claims description 5
125000004036 acetal group Chemical class 0.000 claims description 5
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 5
239000010452 phosphate Substances 0.000 claims description 5
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
150000004010 onium ions Chemical class 0.000 claims description 4
229920000642 polymer Polymers 0.000 claims description 3
239000004925 Acrylic resin Substances 0.000 claims description 2
229920000178 Acrylic resin Polymers 0.000 claims description 2
238000005886 esterification reaction Methods 0.000 claims description 2
230000032050 esterification Effects 0.000 claims 1
239000008199 coating composition Substances 0.000 abstract description 54
238000003860 storage Methods 0.000 abstract description 48
239000003054 catalyst Substances 0.000 abstract description 22
239000000853 adhesive Substances 0.000 abstract description 5
230000001070 adhesive effect Effects 0.000 abstract description 5
239000000976 ink Substances 0.000 abstract description 5
239000002991 molded plastic Substances 0.000 abstract description 5
230000000704 physical effect Effects 0.000 abstract description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract description 5
229920002554 vinyl polymer Polymers 0.000 abstract description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 4
239000011593 sulfur Substances 0.000 abstract description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 3
229910052760 oxygen Inorganic materials 0.000 abstract description 3
239000001301 oxygen Substances 0.000 abstract description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 68
239000000463 material Substances 0.000 description 54
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 52
239000000243 solution Substances 0.000 description 47
239000000047 product Substances 0.000 description 45
238000000576 coating method Methods 0.000 description 42
239000011248 coating agent Substances 0.000 description 37
238000012360 testing method Methods 0.000 description 37
239000008096 xylene Substances 0.000 description 30
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 29
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 23
230000000052 comparative effect Effects 0.000 description 22
230000008859 change Effects 0.000 description 21
239000007787 solid Substances 0.000 description 20
229920003270 Cymel® Polymers 0.000 description 19
238000003756 stirring Methods 0.000 description 18
239000002585 base Substances 0.000 description 17
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 16
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 16
238000005507 spraying Methods 0.000 description 16
SOGAXMICEFXMKE-UHFFFAOYSA-N alpha-Methyl-n-butyl acrylate Natural products CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
239000000178 monomer Substances 0.000 description 14
239000004576 sand Substances 0.000 description 14
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 13
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 13
FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 13
229960000834 vinyl ether Drugs 0.000 description 13
238000010992 reflux Methods 0.000 description 12
239000002904 solvent Substances 0.000 description 12
238000013329 compounding Methods 0.000 description 11
230000003247 decreasing effect Effects 0.000 description 11
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
125000000217 alkyl group Chemical group 0.000 description 10
125000003118 aryl group Chemical group 0.000 description 10
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
WRKCIHRWQZQBOL-UHFFFAOYSA-N octyl dihydrogen phosphate Chemical compound CCCCCCCCOP(O)(O)=O WRKCIHRWQZQBOL-UHFFFAOYSA-N 0.000 description 8
229940126062 Compound A Drugs 0.000 description 7
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
239000002994 raw material Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
239000004408 titanium dioxide Substances 0.000 description 7
OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
238000009500 colour coating Methods 0.000 description 6
229920001577 copolymer Polymers 0.000 description 6
238000004070 electrodeposition Methods 0.000 description 6
238000011156 evaluation Methods 0.000 description 6
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 6
FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 6
229920001519 homopolymer Polymers 0.000 description 6
239000012948 isocyanate Substances 0.000 description 6
150000002513 isocyanates Chemical class 0.000 description 6
SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 6
239000003973 paint Substances 0.000 description 6
235000011007 phosphoric acid Nutrition 0.000 description 6
OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 5
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
125000002877 alkyl aryl group Chemical group 0.000 description 5
150000003460 sulfonic acids Chemical class 0.000 description 5
230000000007 visual effect Effects 0.000 description 5
ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 4
GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 4
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 4
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
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BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
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235000001014 amino acid Nutrition 0.000 description 4
LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 4
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238000001816 cooling Methods 0.000 description 4
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238000013100 final test Methods 0.000 description 4
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
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UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 3
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UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
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239000004593 Epoxy Substances 0.000 description 3
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125000001931 aliphatic group Chemical group 0.000 description 3
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150000002391 heterocyclic compounds Chemical class 0.000 description 3
239000003999 initiator Substances 0.000 description 3
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
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239000012044 organic layer Substances 0.000 description 3
239000003505 polymerization initiator Substances 0.000 description 3
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SDQCGKJCBWXRMK-UHFFFAOYSA-N propan-2-yl 4-methylbenzenesulfonate Chemical compound CC(C)OS(=O)(=O)C1=CC=C(C)C=C1 SDQCGKJCBWXRMK-UHFFFAOYSA-N 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
239000010959 steel Substances 0.000 description 3
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
238000005406 washing Methods 0.000 description 3
LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 3
229910000165 zinc phosphate Inorganic materials 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
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ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
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235000019454 L-leucine Nutrition 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
239000004640 Melamine resin Substances 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 1
239000005062 Polybutadiene Substances 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920002873 Polyethylenimine Polymers 0.000 description 1
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
229920001807 Urea-formaldehyde Polymers 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229960002684 aminocaproic acid Drugs 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
229960005261 aspartic acid Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
WOBLPRFQALLAMN-UHFFFAOYSA-N butyl acetate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCCCOC(C)=O WOBLPRFQALLAMN-UHFFFAOYSA-N 0.000 description 1
QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
150000001793 charged compounds Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
229960002173 citrulline Drugs 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000005336 cracking Methods 0.000 description 1
238000007278 cyanoethylation reaction Methods 0.000 description 1
VKONPUDBRVKQLM-UHFFFAOYSA-N cyclohexane-1,4-diol Chemical compound OC1CCC(O)CC1 VKONPUDBRVKQLM-UHFFFAOYSA-N 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229950010030 dl-alanine Drugs 0.000 description 1
YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
WZCMJGCQGDDUID-UHFFFAOYSA-N ethenylsulfanylcyclohexane Chemical compound C=CSC1CCCCC1 WZCMJGCQGDDUID-UHFFFAOYSA-N 0.000 description 1
AFGACPRTZOCNIW-UHFFFAOYSA-N ethenylsulfanylethane Chemical compound CCSC=C AFGACPRTZOCNIW-UHFFFAOYSA-N 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
229960002989 glutamic acid Drugs 0.000 description 1
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
229960002449 glycine Drugs 0.000 description 1
229940043257 glycylglycine Drugs 0.000 description 1
238000007542 hardness measurement Methods 0.000 description 1
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
JLPAWRLRMTZCSF-UHFFFAOYSA-N hydroxypyruvaldehyde Chemical compound OCC(=O)C=O JLPAWRLRMTZCSF-UHFFFAOYSA-N 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
150000003951 lactams Chemical class 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
229960003136 leucine Drugs 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
150000007974 melamines Chemical class 0.000 description 1
HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
AMBKPYJJYUKNFI-UHFFFAOYSA-N methylsulfanylethene Chemical compound CSC=C AMBKPYJJYUKNFI-UHFFFAOYSA-N 0.000 description 1
UJQMLHKSZKBMMO-UHFFFAOYSA-N n,n-diethylethanamine;pyridine Chemical compound C1=CC=NC=C1.CCN(CC)CC UJQMLHKSZKBMMO-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
XXDKRMQJHKMZPC-UHFFFAOYSA-N octan-2-yl 4-methylbenzenesulfonate Chemical compound CCCCCCC(C)OS(=O)(=O)C1=CC=C(C)C=C1 XXDKRMQJHKMZPC-UHFFFAOYSA-N 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
RPDJEKMSFIRVII-UHFFFAOYSA-N oxomethylidenehydrazine Chemical group NN=C=O RPDJEKMSFIRVII-UHFFFAOYSA-N 0.000 description 1
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920002857 polybutadiene Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
229920001289 polyvinyl ether Polymers 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000008569 process Effects 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
XBMKBXSYVCYTFB-UHFFFAOYSA-N pyridine;sulfane Chemical compound S.C1=CC=NC=C1 XBMKBXSYVCYTFB-UHFFFAOYSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229960001153 serine Drugs 0.000 description 1
150000004756 silanes Chemical class 0.000 description 1
QLCKHRQGBNMBPB-UHFFFAOYSA-M sodium;3,4-dihydro-2h-pyran-2-carboxylate Chemical compound [Na+].[O-]C(=O)C1CCC=CO1 QLCKHRQGBNMBPB-UHFFFAOYSA-M 0.000 description 1
FYJOAQUACGBHMP-UHFFFAOYSA-M sodium;3,4-dihydro-2h-thiopyran-2-carboxylate Chemical compound [Na+].[O-]C(=O)C1CCC=CS1 FYJOAQUACGBHMP-UHFFFAOYSA-M 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
239000013638 trimer Substances 0.000 description 1
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
239000012855 volatile organic compound Substances 0.000 description 1
238000004383 yellowing Methods 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/06—Unsaturated polyesters

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Compositions Of Macromolecular Compounds (AREA)
Paints Or Removers (AREA)
Epoxy Resins (AREA)
Polyesters Or Polycarbonates (AREA)
Polyurethanes Or Polyureas (AREA)

CA002040167A 1990-04-10 1991-04-10 Compositions thermodurcissables, composes de carboxyl a agent de durcissement inhibe et methodes de preparation desdits produits Expired - Lifetime CA2040167C (fr)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
JP9426790		1990-04-10
JP94267/1990		1990-04-10
JP259695/1990		1990-09-28
JP25969590		1990-09-28
JP28877690		1990-10-26
JP288776/1990		1990-10-26

Publications (2)

Publication Number	Publication Date
CA2040167A1 CA2040167A1 (fr)	1991-10-11
CA2040167C true CA2040167C (fr)	1997-12-16

Family

ID=27307505

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002040167A Expired - Lifetime CA2040167C (fr)	1990-04-10	1991-04-10	Compositions thermodurcissables, composes de carboxyl a agent de durcissement inhibe et methodes de preparation desdits produits

Country Status (2)

Country	Link
KR (1)	KR950010118B1 (fr)
CA (1)	CA2040167C (fr)

1991
- 1991-04-08 KR KR1019910005563A patent/KR950010118B1/ko not_active Expired - Lifetime
- 1991-04-10 CA CA002040167A patent/CA2040167C/fr not_active Expired - Lifetime

Also Published As

Publication number	Publication date
KR910018477A (ko)	1991-11-30
CA2040167A1 (fr)	1991-10-11
KR950010118B1 (ko)	1995-09-07

Legal Events

Date	Code	Title	Description
1993-03-23	EEER	Examination request
2011-04-10	MKLA	Lapsed
2012-12-02	MKEC	Expiry (correction)	Effective date: 20121202

Publication	Publication Date	Title
US5516839A (en)	1996-05-14	Thermal latent carboxyl compounds and methods of preparation thereof
JP2898094B2 (ja)	1999-05-31	エポキシ含有ポリマーおよびポリ酸硬化剤をベースにした粉末コーティング組成物
US5419929A (en)	1995-05-30	Thermosetting compositions, thermal latent acid catalysts, methods of coating and coated articles
JPS63168423A (ja)	1988-07-12	硬化性混合物およびその用途
JPH07286138A (ja)	1995-10-31	被覆剤組成物
US5319024A (en)	1994-06-07	Thermosetting compositions, thermal latent hydroxyl compounds, thermal latent thiol compounds and methods of preparation thereof
US4321335A (en)	1982-03-23	Powder coating resin composition
CA2040167C (fr)	1997-12-16	Compositions thermodurcissables, composes de carboxyl a agent de durcissement inhibe et methodes de preparation desdits produits
EP0654069B1 (fr)	1997-04-23	Composition de peinture
US20040062871A1 (en)	2004-04-01	Method of providing cured coating films free of popping defects
JP2850897B2 (ja)	1999-01-27	潜在化カルボキシル化合物及びその製造方法
CA2079427C (fr)	2000-01-18	Compositions thermodurcissables, catalyseurs acides thermiques latents, methode d'enduction et articles ainsi enduits
CA2040592C (fr)	1997-12-02	Compositions thermodurcissables, composes hydroxyles et composes thioles, a catalyseur thermique latent, et methodes de preparation
JP3033289B2 (ja)	2000-04-17	含フッ素系熱硬化性組成物
JP2746005B2 (ja)	1998-04-28	熱硬化性組成物、熱潜在性酸触媒、塗装仕上げ方法及び塗装物品
JP4873675B2 (ja)	2012-02-08	高耐候性の塗料用樹脂組成物
JP2894317B2 (ja)	1999-05-24	塗装仕上げ方法及び塗装物品
KR950005512B1 (ko)	1995-05-24	잠재화카르복실화합물 및 그 제조방법
JP3042033B2 (ja)	2000-05-15	潜在化カルボキシル化合物及びそれを含む熱硬化性組成物
KR950010119B1 (ko)	1995-09-07	열경화성 조성물
JPH10147747A (ja)	1998-06-02	複合塗膜の塗装仕上げ方法及び塗装物品
JPH01146966A (ja)	1989-06-08	塗料用樹脂組成物
JP2004196953A (ja)	2004-07-15	粉体塗料組成物
JP2004196952A (ja)	2004-07-15	粉体塗料組成物
JPH11335593A (ja)	1999-12-07	新規な粉体塗料用樹脂組成物