CA2338378A1 - Monomer-poor polyurethane bonding agent having an improved lubricant adhesion - Google Patents

Monomer-poor polyurethane bonding agent having an improved lubricant adhesion Download PDF

Info

Publication number: CA2338378A1
Authority: CA; Canada
Prior art keywords: isocyanate; component; groups; stage; polyurethane
Prior art date: 1998-07-20
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

Application number

CA002338378A

Other languages

English (en)

French (fr)

Inventor

Gerd Bolte

Markus Krudenscheidt

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.)

Henkel AG and Co KGaA

Original Assignee

Individual

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.)

1998-07-20

Filing date

1999-07-10

Publication date

2000-02-03

1999-07-10 Application filed by Individual filed Critical Individual

2000-02-03 Publication of CA2338378A1 publication Critical patent/CA2338378A1/en

Status Abandoned legal-status Critical Current

Links

239000004814 polyurethane Substances 0.000 title claims abstract description 83
229920002635 polyurethane Polymers 0.000 title claims abstract description 78
239000000314 lubricant Substances 0.000 title abstract description 12
239000007767 bonding agent Substances 0.000 title abstract description 7
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 99
238000004519 manufacturing process Methods 0.000 claims abstract description 33
239000000853 adhesive Substances 0.000 claims abstract description 30
230000001070 adhesive effect Effects 0.000 claims abstract description 30
239000000178 monomer Substances 0.000 claims abstract description 14
238000000576 coating method Methods 0.000 claims abstract description 12
229920005989 resin Polymers 0.000 claims abstract description 7
239000011347 resin Substances 0.000 claims abstract description 7
238000005266 casting Methods 0.000 claims abstract description 5
239000004922 lacquer Substances 0.000 claims abstract description 4
239000003973 paint Substances 0.000 claims abstract description 4
239000012948 isocyanate Substances 0.000 claims description 99
150000002513 isocyanates Chemical class 0.000 claims description 95
239000011230 binding agent Substances 0.000 claims description 68
239000000203 mixture Substances 0.000 claims description 60
229920005862 polyol Polymers 0.000 claims description 59
150000003077 polyols Chemical class 0.000 claims description 59
229920001730 Moisture cure polyurethane Polymers 0.000 claims description 52
238000000034 method Methods 0.000 claims description 38
230000008569 process Effects 0.000 claims description 36
238000006243 chemical reaction Methods 0.000 claims description 34
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
150000001875 compounds Chemical class 0.000 claims description 26
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 22
229910052757 nitrogen Inorganic materials 0.000 claims description 21
125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
230000009257 reactivity Effects 0.000 claims description 21
NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 12
NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-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 10
239000011248 coating agent Substances 0.000 claims description 7
125000000524 functional group Chemical group 0.000 claims description 7
238000002156 mixing Methods 0.000 claims description 7
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 5
238000000465 moulding Methods 0.000 claims description 4
229920000642 polymer Polymers 0.000 claims description 4
HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 claims description 3
239000000839 emulsion Substances 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000000463 material Substances 0.000 abstract description 7
239000000470 constituent Substances 0.000 abstract description 3
229920003023 plastic Polymers 0.000 abstract description 3
239000004033 plastic Substances 0.000 abstract description 3
229910052782 aluminium Inorganic materials 0.000 abstract description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract description 2
239000006185 dispersion Substances 0.000 abstract description 2
238000004026 adhesive bonding Methods 0.000 abstract 1
125000005442 diisocyanate group Chemical group 0.000 description 33
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 23
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 22
-1 aliphatic alcohols Chemical class 0.000 description 22
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 21
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239000000047 product Substances 0.000 description 13
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 11
239000005057 Hexamethylene diisocyanate Substances 0.000 description 10
150000001298 alcohols Chemical class 0.000 description 10
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239000005056 polyisocyanate Substances 0.000 description 10
229920001228 polyisocyanate Polymers 0.000 description 10
239000004014 plasticizer Substances 0.000 description 9
150000005846 sugar alcohols Polymers 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 8
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239000005058 Isophorone diisocyanate Substances 0.000 description 7
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239000007795 chemical reaction product Substances 0.000 description 7
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239000004721 Polyphenylene oxide Substances 0.000 description 6
238000004806 packaging method and process Methods 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
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238000006384 oligomerization reaction Methods 0.000 description 5
239000004848 polyfunctional curative Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
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239000004698 Polyethylene Substances 0.000 description 4
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
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239000001361 adipic acid Substances 0.000 description 4
235000011037 adipic acid Nutrition 0.000 description 4
125000002947 alkylene group Chemical group 0.000 description 4
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
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150000001991 dicarboxylic acids Chemical class 0.000 description 4
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238000009472 formulation Methods 0.000 description 4
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
150000002989 phenols Chemical class 0.000 description 4
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238000006116 polymerization reaction Methods 0.000 description 4
238000007789 sealing Methods 0.000 description 4
ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
230000008901 benefit Effects 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000000539 dimer Substances 0.000 description 3
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
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239000007788 liquid Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229920000728 polyester Polymers 0.000 description 3
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230000035484 reaction time Effects 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
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KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
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RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 2
ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/08—Polyurethanes from polyethers
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4804—Two or more polyethers of different physical or chemical nature
- C08G18/4808—Mixtures of two or more polyetherdiols
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Polyurethanes Or Polyureas (AREA)
Adhesives Or Adhesive Processes (AREA)
Paints Or Removers (AREA)
Lubricants (AREA)

CA002338378A 1998-07-20 1999-07-10 Monomer-poor polyurethane bonding agent having an improved lubricant adhesion Abandoned CA2338378A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19832556.8		1998-07-20
DE19832556		1998-07-20
PCT/EP1999/004890 WO2000005290A1 (de)	1998-07-20	1999-07-10	Monomerarmes polyurethanbindemittel mit verbesserter gleitmittelhaftung

Publications (1)

Publication Number	Publication Date
CA2338378A1 true CA2338378A1 (en)	2000-02-03

Family

ID=7874664

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002338378A Abandoned CA2338378A1 (en)	1998-07-20	1999-07-10	Monomer-poor polyurethane bonding agent having an improved lubricant adhesion

Country Status (15)

Country	Link
EP (1)	EP1100839A1 (de)
JP (1)	JP2003519243A (de)
KR (1)	KR20010053584A (de)
CN (1)	CN1310733A (de)
AU (1)	AU4909699A (de)
BR (1)	BR9912309A (de)
CA (1)	CA2338378A1 (de)
DE (1)	DE19931997A1 (de)
HR (1)	HRP20000902A2 (de)
HU (1)	HUP0102626A2 (de)
ID (1)	ID30020A (de)
NO (1)	NO20010327L (de)
SK (1)	SK992001A3 (de)
TR (1)	TR200100058T2 (de)
WO (1)	WO2000005290A1 (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR100586132B1 (ko) *	1999-04-23	2006-06-02	닛폰 폴리우레탄 고교 가부시키가이샤	라미네이트용 접착제
EP1338635B2 (de)	2002-02-22	2020-10-14	Jowat AG	Polyurethan-Zusammensetzungen mit geringem Anteil an Diisocyanatmonomer(en)
JP4783276B2 (ja) *	2006-12-25	2011-09-28	三洋化成工業株式会社	ポリエステル系ウレタン樹脂。
DE102008027914A1 (de)	2008-06-12	2009-12-17	Henkel Ag & Co. Kgaa	Vernetzende 2K-Isocyanat-Zusammensetzungen
MX344974B (es) *	2010-12-20	2017-01-12	Akzo Nobel Coatings Int Bv	Membranas y revestimientos a base de mdi de los prepolimeros con muy bajo contenido de isocianatos monomericos.
CN103502296B (zh) *	2011-04-15	2015-11-25	H.B.富勒公司	改性的二苯甲烷二异氰酸酯基粘合剂

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2917314B1 (de) *	1979-04-28	1980-09-25	Haeger & Kaessner Gmbh	Verfahren zur Herstellung elastischer,wetterbestaendiger Flaechengebilde
DE3306559A1 (de) *	1983-02-25	1984-08-30	Henkel KGaA, 4000 Düsseldorf	Verfahren zur herstellung von polyurethan-praepolymeren mit endstaendigen isocyanatgruppen und vermindertem restmonomergehalt
DE3401129A1 (de) *	1984-01-14	1985-07-18	Henkel KGaA, 4000 Düsseldorf	Verfahren zur herstellung gemischter polyurethan-prepolymerer
CA2094554C (en) *	1992-05-12	2001-12-25	Thirumurti Narayan	Polymethylene polyphenyl polyisocyanate based prepolymers
DE19700014A1 (de) *	1997-01-02	1998-07-09	Henkel Kgaa	Monomerenarmes PU-Prepolymer
JP4249898B2 (ja) *	1997-11-11	2009-04-08	ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェン	易揮発性モノマー含有量の低いポリウレタンバインダー

1999
- 1999-07-09 DE DE19931997A patent/DE19931997A1/de not_active Withdrawn
- 1999-07-10 EP EP99932867A patent/EP1100839A1/de not_active Withdrawn
- 1999-07-10 ID IDW20010162D patent/ID30020A/id unknown
- 1999-07-10 CA CA002338378A patent/CA2338378A1/en not_active Abandoned
- 1999-07-10 BR BR9912309-6A patent/BR9912309A/pt not_active Application Discontinuation
- 1999-07-10 KR KR1020017000850A patent/KR20010053584A/ko not_active Application Discontinuation
- 1999-07-10 AU AU49096/99A patent/AU4909699A/en not_active Abandoned
- 1999-07-10 TR TR2001/00058T patent/TR200100058T2/xx unknown
- 1999-07-10 CN CN99808826A patent/CN1310733A/zh active Pending
- 1999-07-10 JP JP2000561244A patent/JP2003519243A/ja active Pending
- 1999-07-10 SK SK99-2001A patent/SK992001A3/sk unknown
- 1999-07-10 WO PCT/EP1999/004890 patent/WO2000005290A1/de not_active Application Discontinuation
- 1999-07-10 HU HU0102626A patent/HUP0102626A2/hu unknown
2000
- 2000-12-28 HR HR20000902A patent/HRP20000902A2/hr not_active Application Discontinuation
2001
- 2001-01-19 NO NO20010327A patent/NO20010327L/no unknown

Also Published As

Publication number	Publication date
HUP0102626A2 (hu)	2001-11-28
TR200100058T2 (tr)	2001-05-21
AU4909699A (en)	2000-02-14
ID30020A (id)	2001-11-01
NO20010327D0 (no)	2001-01-19
JP2003519243A (ja)	2003-06-17
WO2000005290A1 (de)	2000-02-03
CN1310733A (zh)	2001-08-29
DE19931997A1 (de)	2000-01-27
BR9912309A (pt)	2001-05-08
EP1100839A1 (de)	2001-05-23
HRP20000902A2 (en)	2001-08-31
KR20010053584A (ko)	2001-06-25
NO20010327L (no)	2001-03-13
SK992001A3 (en)	2001-08-06

Legal Events

Date	Code	Title	Description
2003-11-28	EEER	Examination request
2008-12-29	FZDE	Discontinued

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MXPA01000635A (en)	2001-12-04	Monomer-poor polyurethane bonding agent having an improved lubricant adhesion
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