CA2049695C - Systeme de durcissement pour les prepolymeres de type isocyanate - Google Patents

Systeme de durcissement pour les prepolymeres de type isocyanate Download PDF

Info

Publication number: CA2049695C
Authority: CA; Canada
Prior art keywords: oxazolidine; curing agent; curing; composition according; hydroxyl
Prior art date: 1991-08-22
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 2049695

Other languages

English (en)

Other versions

CA2049695A1 (fr

Inventor

Witek Majewski

Hamdy Khalil

Jerzy Wypych

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.)

RPM Canada Co

Original Assignee

RPM Canada 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.)

1991-08-22

Filing date

1991-08-22

Publication date

2003-08-05

1991-08-22 Application filed by RPM Canada Co filed Critical RPM Canada Co

1991-08-22 Priority to CA 2049695 priority Critical patent/CA2049695C/fr

1993-02-23 Publication of CA2049695A1 publication Critical patent/CA2049695A1/fr

2003-08-05 Application granted granted Critical

2003-08-05 Publication of CA2049695C publication Critical patent/CA2049695C/fr

2011-08-22 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000012948 isocyanate Substances 0.000 title claims abstract description 70
150000002513 isocyanates Chemical class 0.000 title claims abstract description 65
239000000203 mixture Substances 0.000 claims abstract description 72
239000003795 chemical substances by application Substances 0.000 claims abstract description 59
WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims abstract description 58
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 50
239000003054 catalyst Substances 0.000 claims abstract description 18
150000001875 compounds Chemical class 0.000 claims abstract description 18
239000002516 radical scavenger Substances 0.000 claims abstract description 16
125000002619 bicyclic group Chemical group 0.000 claims abstract description 6
239000003960 organic solvent Substances 0.000 claims abstract description 6
125000002950 monocyclic group Chemical group 0.000 claims abstract description 5
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 26
-1 polytetramethylene Polymers 0.000 claims description 26
238000000034 method Methods 0.000 claims description 19
230000008569 process Effects 0.000 claims description 18
239000008096 xylene Substances 0.000 claims description 16
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 15
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 12
229920001610 polycaprolactone Polymers 0.000 claims description 12
239000004632 polycaprolactone Substances 0.000 claims description 12
ZAXXZBQODQDCOW-UHFFFAOYSA-N 1-methoxypropyl acetate Chemical compound CCC(OC)OC(C)=O ZAXXZBQODQDCOW-UHFFFAOYSA-N 0.000 claims description 11
NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 claims description 10
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 10
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 claims description 9
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
150000002009 diols Chemical class 0.000 claims description 9
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 8
229920005862 polyol Polymers 0.000 claims description 8
150000003077 polyols Chemical class 0.000 claims description 8
229920001451 polypropylene glycol Polymers 0.000 claims description 8
239000000463 material Substances 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 4
CBFOYGMBDYCRIO-UHFFFAOYSA-N 1-ethoxypent-2-ene Chemical group CCOCC=CCC CBFOYGMBDYCRIO-UHFFFAOYSA-N 0.000 claims description 3
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
150000008065 acid anhydrides Chemical class 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
150000001805 chlorine compounds Chemical class 0.000 claims description 3
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
230000006872 improvement Effects 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical group CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims 2
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical class CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims 2
239000012975 dibutyltin dilaurate Chemical class 0.000 claims 2
229910017464 nitrogen compound Inorganic materials 0.000 claims 2
150000002830 nitrogen compounds Chemical group 0.000 claims 2
150000007513 acids Chemical class 0.000 claims 1
229920000642 polymer Polymers 0.000 abstract description 19
238000006243 chemical reaction Methods 0.000 abstract description 16
239000004814 polyurethane Substances 0.000 abstract description 11
229920002396 Polyurea Polymers 0.000 abstract description 7
239000000945 filler Substances 0.000 abstract description 5
229920003226 polyurethane urea Polymers 0.000 abstract description 5
230000007613 environmental effect Effects 0.000 abstract 1
239000000047 product Substances 0.000 description 21
239000004848 polyfunctional curative Substances 0.000 description 13
239000002904 solvent Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 6
229920002635 polyurethane Polymers 0.000 description 6
239000000243 solution Substances 0.000 description 6
125000001931 aliphatic group Chemical group 0.000 description 5
229940113165 trimethylolpropane Drugs 0.000 description 5
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
150000002917 oxazolidines Chemical class 0.000 description 4
239000011253 protective coating Substances 0.000 description 4
239000000565 sealant Substances 0.000 description 4
239000005058 Isophorone diisocyanate Substances 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
239000011521 glass Substances 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
229910052757 nitrogen Inorganic materials 0.000 description 3
239000005056 polyisocyanate Substances 0.000 description 3
229920001228 polyisocyanate Polymers 0.000 description 3
238000007086 side reaction Methods 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
229910052797 bismuth Inorganic materials 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000004927 clay Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
238000005336 cracking Methods 0.000 description 2
229920006037 cross link polymer Polymers 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
150000002334 glycols Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
125000000160 oxazolidinyl group Chemical group 0.000 description 2
230000035515 penetration Effects 0.000 description 2
230000000704 physical effect Effects 0.000 description 2
229920005906 polyester polyol Polymers 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000012360 testing method Methods 0.000 description 2
239000004408 titanium dioxide Substances 0.000 description 2
229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
229920001730 Moisture cure polyurethane Polymers 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000012467 final product Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
150000002483 hydrogen compounds Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
HFHZKZSRXITVMK-UHFFFAOYSA-N oxyphenbutazone Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=C(O)C=C1 HFHZKZSRXITVMK-UHFFFAOYSA-N 0.000 description 1
229960000649 oxyphenbutazone Drugs 0.000 description 1
239000003973 paint Substances 0.000 description 1
230000035699 permeability Effects 0.000 description 1
229920000162 poly(ureaurethane) Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
238000010107 reaction injection moulding Methods 0.000 description 1
230000002000 scavenging effect Effects 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
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 1
239000013638 trimer Substances 0.000 description 1
150000004072 triols Chemical class 0.000 description 1
238000004078 waterproofing Methods 0.000 description 1

Landscapes

Polyurethanes Or Polyureas (AREA)

CA 2049695 1991-08-22 1991-08-22 Systeme de durcissement pour les prepolymeres de type isocyanate Expired - Lifetime CA2049695C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA 2049695 CA2049695C (fr)	1991-08-22	1991-08-22	Systeme de durcissement pour les prepolymeres de type isocyanate

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA 2049695 CA2049695C (fr)	1991-08-22	1991-08-22	Systeme de durcissement pour les prepolymeres de type isocyanate

Publications (2)

Publication Number	Publication Date
CA2049695A1 CA2049695A1 (fr)	1993-02-23
CA2049695C true CA2049695C (fr)	2003-08-05

Family

ID=4148235

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2049695 Expired - Lifetime CA2049695C (fr)	1991-08-22	1991-08-22	Systeme de durcissement pour les prepolymeres de type isocyanate

Country Status (1)

Country	Link
CA (1)	CA2049695C (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1468030A4 (fr) *	2002-01-23	2005-08-10	Rhodia	Composition d'enrobage a base de polyurethanne

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR100414602B1 (ko) *	1995-01-13	2004-02-18	에섹스 스페시얼티 프로덕츠, 인코오포레이티드	2-부분습윤경화성폴리우레탄접착제
US5922809A (en) *	1996-01-11	1999-07-13	The Dow Chemical Company	One-part moisture curable polyurethane adhesive
AR005429A1 (es) *	1996-01-11	1999-06-23	Essex Specialty Prod	Prepolimeros de poliuretano, composiciones adhesivas en un solo envase que incluyen dichos prepolimeros y procedimiento para adherir substratos con dichascomposiciones
US5852103A (en) *	1996-05-08	1998-12-22	Essex Specialty Products, Inc.	Two-part moisture curable polyurethane adhesive
US6545117B1 (en)	1997-08-07	2003-04-08	Akzo Noble N.V.	Sprayable coating compositions comprising an oxazolidine functional compound, an isocyanate functional compound, and a compound selected from a mercapto and a sulfonic acid functional compound
US5977285A (en) *	1997-08-07	1999-11-02	Akzo Nobel N.V.	Sprayable coating compositions comprising oxazolidines, isocyanates and hydroxyl or amine functional resins
DE10142296C1 (de)	2001-08-29	2003-02-13	Bayer Ag	Polyurethanelastomere, Verfahren zu ihrer Herstellung und ihre Verwendung
WO2016114876A1 (fr) *	2015-01-13	2016-07-21	The Shepherd Chemical Company	Nouveaux agents durcisseurs de polyuréthanne

1991
- 1991-08-22 CA CA 2049695 patent/CA2049695C/fr not_active Expired - Lifetime

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1468030A4 (fr) *	2002-01-23	2005-08-10	Rhodia	Composition d'enrobage a base de polyurethanne

Also Published As

Publication number	Publication date
CA2049695A1 (fr)	1993-02-23

Legal Events

Date	Code	Title	Description
1998-08-24	EEER	Examination request
2011-08-22	MKEX	Expiry

Publication	Publication Date	Title
US5126421A (en)	1992-06-30	Curing system for isocyanate prepolymers
US5171818A (en)	1992-12-15	Sprayable aliphatic polyurea-polyurethane coating compositions and methods
KR900006909B1 (ko)	1990-09-24	폴리우레탄에 기초한 화학적으로 경화시키는 2성분계 물질로 되는 조성물 및 그의 제조방법
US4695618A (en)	1987-09-22	Solventless polyurethane spray compositions and method for applying them
US4425468A (en)	1984-01-10	Polyurea-polyurethane acrylate polymer dispersions
US5124425A (en)	1992-06-23	Curable polyurethane composition excellent in flexibility
KR101307292B1 (ko)	2013-09-12	가요성 복합 엘라스토머 폴리우레탄 스킨을 제조하기 위한 방법
US5574124A (en)	1996-11-12	Isocyanate prepolymers, a process for their preparation and their use
CN1048225A (zh)	1991-01-02	喷雾聚氨酯弹性体的制造方法
MXPA96000899A (es)	1997-08-01	Revestimientos de poliuretano con ultra-bajocontenido de componentes organicos volatiles
CA2049695C (fr)	2003-08-05	Systeme de durcissement pour les prepolymeres de type isocyanate
US6084001A (en)	2000-07-04	High build polyurethane coating
US5473043A (en)	1995-12-05	Moisture-curable urethane resin compositions
JPH0525241A (ja)	1993-02-02	エーテル基とエステル基とを有するイソシアネートプレポリマー、その製造方法、並びに被覆用、封止用もしくは流延用組成物を製造するためのその使用
CA2019535C (fr)	2000-02-22	Melanges thermodurcissables et leur emploi dans la preparation de revetements pour supports resistant a la chaleur
CA2212900C (fr)	2008-01-22	Compositions reactives douees d'une vie en pot prolongee
JP3197636B2 (ja)	2001-08-13	ウレタン組成物
US5004794A (en)	1991-04-02	Isocyanate prepolymers
JPH072824B2 (ja)	1995-01-18	ポリウレタンの製造法
JPH0841156A (ja)	1996-02-13	常温硬化性塗膜防水材の製造方法
JPH05345876A (ja)	1993-12-27	ウレタン系硬質床仕上げ用組成物
EP0122894A1 (fr)	1984-10-24	Procédé de préparation de polyuréthanes par utilisation d'un oxyde de polyhydroxyalkylphosphine comme durcisseur
JPH1087778A (ja)	1998-04-07	二液型硬化性組成物
JP4198767B2 (ja)	2008-12-17	常温硬化型ポリウレタン塗膜材の製造方法
JPS6248988B2 (fr)	1987-10-16

CA2049695C - Systeme de durcissement pour les prepolymeres de type isocyanate - Google Patents

Info

Links

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (2)

Family

ID=4148235

Family Applications (1)

Country Status (1)

Cited By (1)

Families Citing this family (8)

Cited By (1)

Also Published As

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