EP0341578A2 - Priming layer for leather finishing - Google Patents
Priming layer for leather finishing Download PDFInfo
- Publication number
- EP0341578A2 EP0341578A2 EP89108082A EP89108082A EP0341578A2 EP 0341578 A2 EP0341578 A2 EP 0341578A2 EP 89108082 A EP89108082 A EP 89108082A EP 89108082 A EP89108082 A EP 89108082A EP 0341578 A2 EP0341578 A2 EP 0341578A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- weight
- hydrogen
- groups
- leather
- monomers
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C14—SKINS; HIDES; PELTS; LEATHER
- C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
- C14C11/00—Surface finishing of leather
- C14C11/003—Surface finishing of leather using macromolecular compounds
Definitions
- the invention relates to a process for improving the primer for leather finishes and the use of amino-containing polyacrylates as primers for leather finishes.
- leather finishing is the protective layer that is applied to the leather that has been dried after tanning and greasing in order to protect it against moisture, dirt and damage.
- optimal dressing is required to adhere well to the leather.
- precisely this requirement is not satisfactorily met by many dressing systems (see "Das Leder" 27 142-151 (1976)).
- Another problem with hydrophobized leathers is that an improvement in the adhesion is often associated with a deterioration in the hydrophobization.
- the object underlying the invention is therefore to improve the primer for leather finishes.
- the invention accordingly relates to a process for improving the primer for leather finishes, which is characterized in that leather is prepared by copolymerization of polyacrylates containing amino groups before the primer and / or in the primer liquor A) amino group-containing monomers of the general formula I.
- radicals R1 and R2 are hydrogen or methyl groups
- radicals R3 and R4 are hydrogen or alkyl groups having 1 to 4 carbon atoms or together with the nitrogen atom form a piperazine, piperidine or morpholine ring
- Z is an oxygen atom or one NH group
- Polyacrylates containing amino groups which can be prepared by copolymerization of dimethylaminoethyl methacrylate and butyl acrylate are particularly preferred.
- the copolymerization of the amino group-containing polyacrylates is carried out by known polymerization processes in aqueous media which, if desired, contain water-miscible solvents, such as alcohols, for example isopropanol (Ullmanns Encyclopedia of Industrial Chemistry, 4th edition, vol. 19, p. 3 - 4, Verlag Chemie Weinheim 1980).
- a radical-forming substance such as potassium or ammonium peroxide sulfate, tert-butyl hydroperoxide, azobis (cyanopentanoic acid), azoisobutyronitrile or 2,2- ⁇ azobis (2-amidinopropane dihydrochloride) is added in small quantities.
- the polymerization of the monomers is preferably carried out in such a way that monomers containing amino groups and monomeric esters are simultaneously dripped into water which contains the starter.
- the polymerization temperature can vary within a wide range. Depending on the starter used, temperatures between 60 and 100 ° C can be optimal.
- the amino group-containing polyacrylates which can be used as adhesion promoters are soluble in water in neutralized state or are present in hydrosolvated form.
- the copolymerizations are preferably carried out with 5 to 80% by weight of monomers containing amino groups and 95 to 20% by weight of monomeric esters, particularly preferably with 30 to 60% by weight of monomers containing amino groups and 70 to 40% by weight of monomeric esters.
- the adhesive base liquors preferably contain 5 to 50% by weight of the amino group-containing polyacrylates characterized above. It is possible to use the amino group-containing polyacrylates obtainable by copolymerization as such or after dilution with water and / or organic solvents, for example isopropanol, butanol, glycol ethers and / or methyl ethyl ketone, in the adhesive base liquors.
- the adhesive base liquors can be silicone emulsions or solutions, emulsifiers, for example nonionic surfactants, such as ethoxylated fatty alcohols and ethoxylated alkylphenols, if desired in combination with anionic surfactants, such as alkyl alcohol polyoxyalkyl phosphates and sulfates, and / or Wax dispersions are added.
- emulsifiers for example nonionic surfactants, such as ethoxylated fatty alcohols and ethoxylated alkylphenols, if desired in combination with anionic surfactants, such as alkyl alcohol polyoxyalkyl phosphates and sulfates, and / or Wax dispersions are added.
- the primer can be dyed with dye solutions or pigment preparations.
- the adhesive base liquors are applied to leather using spray, plush, casting or roller application processes.
- the proportion of polyacrylates containing amino groups in the base liquor is between 1 and 10 parts by weight, preferably between 3 and 6 parts by weight, based in each case on 100 parts by weight of binder in the base liquor.
- the amino group-containing polyacrylates to be used according to the invention form on leather a significantly improved primer for the subsequent finishing processes.
- a very good primer is formed on hydrophobized leather without negatively influencing the hydrophobization.
- Parts by weight means parts by weight
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Treatment And Processing Of Natural Fur Or Leather (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
Die Erfindung betrifft ein Verfahren zur Verbesserung des Haftgrundes für Lederzurichtungen sowie die Verwendung von aminogruppenhaltigen Polyacrylaten als Haftgrund für Lederzurichtungen.The invention relates to a process for improving the primer for leather finishes and the use of amino-containing polyacrylates as primers for leather finishes.
Als Lederzurichtung wird die Schutzschicht bezeichnet, die auf das nach der Gerbung und Fettung getrocknete Leder aufgetragen wird, um es gegen Feuchtigkeit, Verschmutzung und Beschädigungen zu schützen. Von einer optimalen Zurichtung wird unter anderem verlangt, daß sie auf dem Leder gut haftet. Gerade diese Forderung wird jedoch von vielen Zurichtsystemen nicht in zufriedenstellender Weise erfüllt (siehe "Das Leder" 27 142 - 151 (1976)). Bei hydrophobierten Ledern kommt als weitere Schwierigkeit hinzu, daß eine Verbesserung der Haftung häufig mit einer Verschlechterung der Hydrophobierung verbunden ist.Leather finishing is the protective layer that is applied to the leather that has been dried after tanning and greasing in order to protect it against moisture, dirt and damage. Among other things, optimal dressing is required to adhere well to the leather. However, precisely this requirement is not satisfactorily met by many dressing systems (see "Das Leder" 27 142-151 (1976)). Another problem with hydrophobized leathers is that an improvement in the adhesion is often associated with a deterioration in the hydrophobization.
Die der Erfindung zugrundeliegende Aufgabe ist daher die Verbesserung des Haftgrundes für Lederzurichtungen.The object underlying the invention is therefore to improve the primer for leather finishes.
Es wurde nun die überraschende Feststellung gemacht, daß aminogruppenhaltige Polyacrylate, hergestellt durch Copolymerisation von aminogruppenhaltigen Monomeren und monomeren ungesättigten Estern, auf Ledern, insbesondere hydrophobierten Ledern, einen sehr gute Haftgrund für die nachfolgenden Zurichtprozesse bilden. Ferner war es überraschend, daß bei hydrophobierten Ledern die Haftverbesserung für Zurichtungen nicht mit einer negativen Beeinflussung der Hydrophobierung verbunden ist.It has now been made the surprising finding that polyacrylates containing amino groups, prepared by copolymerizing monomers containing amino groups and monomerically unsaturated esters, on leathers, in particular hydrophobic leathers, form a very good basis for the subsequent finishing processes. Furthermore, it was surprising that in the case of leathers which have been rendered hydrophobic, the improvement in adhesion for dressings is not associated with a negative influence on the hydrophobization.
Gegenstand der Erfindung ist demzufolge ein Verfahren zur Verbesserung des Haftgrundes für Lederzurichtungen, das dadurch gekennzeichnet ist, daß Leder vor der Grundierung und/oder in der Grundierflotte mit aminogruppenhaltigen Polyacrylaten, hergestellt durch Copolymerisation von
A) aminogruppenhaltigen Monomeren der allgemeinen Formel I
B) monomeren Estern der allgemeinen Formel II
R⁵ - CH = CR⁶ - - OR⁷
in der R⁵ und R⁶ Wasserstoff oder Methylgruppen und R⁷ eine Alkylgruppe mit 1 bis 6 C-Atomen bedeuten
behandelt werden.The invention accordingly relates to a process for improving the primer for leather finishes, which is characterized in that leather is prepared by copolymerization of polyacrylates containing amino groups before the primer and / or in the primer liquor
A) amino group-containing monomers of the general formula I.
B) monomeric esters of the general formula II
R⁵ - CH = CR⁶ - - OR⁷
in which R⁵ and R⁶ are hydrogen or methyl groups and R⁷ is an alkyl group having 1 to 6 carbon atoms
be treated.
Weiterer Erfindungsgegenstand ist die Verwendung von aminogruppenhaltigen Polyacrylaten, hergestellt durch Copolymerisation von
A) aminogruppenhaltigen Monomeren der allgemeinen Formel I
B) monomeren Estern der allgemeinen Formel II
R⁵ - CH = CR⁶ - - OR⁷
in der R⁵ und R⁶ Wasserstoff oder Methylgruppen und R⁷ eine Alkylgruppe mit 1 bis 6 C-Atomen bedeuten
als Haftgrund für Lederzurichtungen.Another object of the invention is the use of polyacrylates containing amino groups, produced by copolymerization of
A) monomers of the general formula I containing amino groups
B) monomeric esters of the general formula II
R⁵ - CH = CR⁶ - - OR⁷
in which R⁵ and R⁶ are hydrogen or methyl groups and R⁷ is an alkyl group having 1 to 6 carbon atoms
as a primer for leather finishes.
Eine Verbesserung der Haftung von Zurichtungen wird insbesondere mit solchen aminogruppenhaltigen Polyacrylaten erreicht, die durch Copolymerisation von
- A) Dimethylaminoethyl-methacrylat, Dimethylaminopropyl-methacrylamid, 2-tert.-Butylaminoethyl-methacrylat und/oder Dimethylaminoneopentyl-acrylat und
- B) Alkylestern mit 1 bis 4 C-Atomen im Alkylrest von Acrylsäure, Methacrylsäure, Crotonsäure und/oder 2-Methylcrotonsäure erhalten werden.
- A) dimethylaminoethyl methacrylate, dimethylaminopropyl methacrylamide, 2-tert-butylaminoethyl methacrylate and / or dimethylaminoneopentyl acrylate and
- B) Alkyl esters with 1 to 4 carbon atoms in the alkyl radical of acrylic acid, methacrylic acid, crotonic acid and / or 2-methylcrotonic acid are obtained.
Besonders bevorzugt werden durch Copolymerisation von Dimethylaminoethyl-methacrylat und Butylacrylat herstellbare aminogruppenhaltige Polyacrylate.Polyacrylates containing amino groups which can be prepared by copolymerization of dimethylaminoethyl methacrylate and butyl acrylate are particularly preferred.
Die Copolymerisation der aminogruppenhaltigen Polyacrylate wird nach an sich bekannten Polymerisationsverfahren in wäßrigen Medien, die gewünschtenfalls mit Wasser mischbare Lösungsmittel, wie Alkohole, zum Beispiel Isopropanol, enthalten, durchgeführt (Ullmanns Encyclopädie der technischen Chemie, 4. Aufl., Bd. 19, S. 3 - 4, Verlag Chemie Weinheim 1980). Als Starter wird eine radikalbildende Substanz, beispielsweise Kalium- oder Ammoniumperoxidsulfat, tert.-Butylhydroperoxid, Azobis(cyanpentansäure), Azoisobutyronitril oder 2,2-́Azobis(2-amidinopropandihydrochlorid) in geringen Mengen zugegeben. Vorzugsweise erfolgt die Polymerisation der Monomeren in der Weise, daß aminogruppenhaltige Monomere und monomere Ester gleichzeitig in Wasser, das den Starter enthält, getropft werden. Die Polymerisationstemperatur kann in einem weiten Bereich schwanken. In Abhängigkeit von dem eingesetzten Starter können Temperaturen zwischen 60 und 100 °C optimal sein.The copolymerization of the amino group-containing polyacrylates is carried out by known polymerization processes in aqueous media which, if desired, contain water-miscible solvents, such as alcohols, for example isopropanol (Ullmanns Encyclopedia of Industrial Chemistry, 4th edition, vol. 19, p. 3 - 4, Verlag Chemie Weinheim 1980). As a starter, a radical-forming substance, such as potassium or ammonium peroxide sulfate, tert-butyl hydroperoxide, azobis (cyanopentanoic acid), azoisobutyronitrile or 2,2-́azobis (2-amidinopropane dihydrochloride) is added in small quantities. The polymerization of the monomers is preferably carried out in such a way that monomers containing amino groups and monomeric esters are simultaneously dripped into water which contains the starter. The polymerization temperature can vary within a wide range. Depending on the starter used, temperatures between 60 and 100 ° C can be optimal.
Die als Haftverbesserer einsetzbaren aminogruppenhaltigen Polyacrylate sind in neutralisiertem Zustand in Wasser löslich oder liegen in hydrosolvierter Form vor. Vorzugsweise werden die Copolymerisationen mit 5 bis 80 Gew.-% aminogruppenhaltigen Monomeren und 95 bis 20 Gew.-% monomeren Estern, besonders bevorzugt mit 30 bis 60 Gew.-% aminogruppenhaltigen Monomeren und 70 bis 40 Gew.-% monomeren Estern, durchgeführt.The amino group-containing polyacrylates which can be used as adhesion promoters are soluble in water in neutralized state or are present in hydrosolvated form. The copolymerizations are preferably carried out with 5 to 80% by weight of monomers containing amino groups and 95 to 20% by weight of monomeric esters, particularly preferably with 30 to 60% by weight of monomers containing amino groups and 70 to 40% by weight of monomeric esters.
Die Haftgrundflotten enthalten vorzugsweise 5 bis 50 Gew.-% der oben charakterisierten aminogruppenhaltigen Polyacrylate. Es ist möglich, die durch Copolymerisation erhältlichen aminogruppenhaltigen Polyacrylate als solche oder nach Verdünnung mit Wasser und/oder organischen Lösungsmitteln, beispielsweise Isopropanol, Butanol, Glycolethern und/oder Methylethylketon, in den Haftgrundflotten einzusetzen. Den Haftgrundflotten können Siliconemulsionen oder -lösungen, Emulgatoren, beispielsweise nichtionische Tenside, wie ethoxylierte Fettalkohole und ethoxylierte Alkylphenole, gewünschtenfalls in Kombination mit anionischen Tensiden, wie Alkylalkoholpolyoxyalkylphosphate und -sulfate, und/oder Wachsdispersionen zugesetzt werden. Die Haftgrund kann mit Farbstofflösungen oder Pigmentpräparationen angefärbt werden.The adhesive base liquors preferably contain 5 to 50% by weight of the amino group-containing polyacrylates characterized above. It is possible to use the amino group-containing polyacrylates obtainable by copolymerization as such or after dilution with water and / or organic solvents, for example isopropanol, butanol, glycol ethers and / or methyl ethyl ketone, in the adhesive base liquors. The adhesive base liquors can be silicone emulsions or solutions, emulsifiers, for example nonionic surfactants, such as ethoxylated fatty alcohols and ethoxylated alkylphenols, if desired in combination with anionic surfactants, such as alkyl alcohol polyoxyalkyl phosphates and sulfates, and / or Wax dispersions are added. The primer can be dyed with dye solutions or pigment preparations.
Die Haftgrundflotten werden auf Leder mittels Spritz-, Plüsch-, Gieß- oder Walzenauftragsverfahren appliziert.The adhesive base liquors are applied to leather using spray, plush, casting or roller application processes.
Um eine Verbesserung der Haftung von Zurichtungen zu erzielen, kann es in manchen Fällen vorteilhaft sein, nur einen Teil der Haftgrundflotte auf Leder zu applizieren und den anderen Teil in der Grundierflotte einzusetzen. In diesen Fällen liegt der Anteil der aminogruppenhaltigen Polyacrylate in der Grundierflotte zwischen 1 und 10 Gew.-teilen, vorzugsweise zwischen 3 und 6 Gew.-teilen, jeweils bezogen auf 100 Gew.-teile Binder der Grundierflotte.In order to improve the adhesion of dressings, it can be advantageous in some cases to apply only part of the primer base to leather and use the other part in the primer. In these cases, the proportion of polyacrylates containing amino groups in the base liquor is between 1 and 10 parts by weight, preferably between 3 and 6 parts by weight, based in each case on 100 parts by weight of binder in the base liquor.
Die erfindungsgemäß zu verwendenden aminogruppenhaltigen Polyacrylate bilden auf Leder einen für die anschließenden Zurichtprozesse signifikant verbesserten Haftgrund. Auf hydrophobierten Ledern wird ein sehr gute Haftgrund ohne negative Beeinflussung der Hydrophobierung gebildet.The amino group-containing polyacrylates to be used according to the invention form on leather a significantly improved primer for the subsequent finishing processes. A very good primer is formed on hydrophobized leather without negatively influencing the hydrophobization.
In einem Reaktor mit Rührer, 2 Zulaufgefäßen, Heizung, Kühlung, Rückflußkühlung sowie Temperaturmessung wurden 200 g 2,2 -́Azobis(2-amidinopropandihydrochlorid) und 55,8 kg Wasser vorgelegt. In das eine Zulaufgefäß wurde eine Mischung aus 16,7 kg Dimethylaminoethylmethacrylat, 16,7 kg Butylacrylat und 0,7 kg Ameisensäure (98 %ig) gegeben, in das andere eine Lösung aus 400 g 2,2 -́Azobis(2-amidinopropandihydrochlorid) und 4,8 kg Wasser. Nach Erwärmen der Vorlagelösung im Reaktor unter Rühren auf 75 °C wurden beide Zulauflösungen parallel innerhalb von 90 Minuten zugegeben. Dabei wurde eine Innentemperatur von 80 bis 82 °C erhalten. Nach beendetem Zulauf wurde die Mischung 60 Minuten bei 75 °C gerührt. Danach wurde auf 45 °C abgekühlt und mit 4,7 kg einer 50 Gew.-%igen Ameisensäure neutralisiert. Die Neutralisation wurde bis zu einem stabilen pH-Wert von 6,5 durchgeführt.
Gew.-teile bedeutet GewichtsteileParts by weight means parts by weight
Die Haftprüfungen wurden nach IUF 470 durchgeführt.The adhesion tests were carried out according to IUF 470.
Wie Beispiel 1, jedoch ohne Haftgrund
Wie Beispiel 3, jedoch ohne Haftgrund
Claims (6)
A) aminogruppenhaltigen Monomeren der allgemeinen Formel I
B) monomeren Estern der allgemeinen Formel II
R⁵ - CH = CR⁶ - - OR⁷
in der R⁵ und R⁶ Wasserstoff oder Methylgruppen und R⁷ eine Alkylgruppe mit 1 bis 6 C-Atomen bedeuten
behandelt werden.1. A method for improving the primer for leather finishes, characterized in that leather before the primer and / or in the priming liquor with amino group-containing polyacrylates, prepared by copolymerization of
A) monomers of the general formula I containing amino groups
B) monomeric esters of the general formula II
R⁵ - CH = CR⁶ - - OR⁷
in which R⁵ and R⁶ are hydrogen or methyl groups and R⁷ is an alkyl group having 1 to 6 carbon atoms
be treated.
A) aminogruppenhaltigen Monomeren der allgemeinen Formel I
B) monomeren Estern der allgemeinen Formel II
R⁵ - CH = CR⁶ - - OR⁷
in der R⁵ und R⁶ Wasserstoff oder Methylgruppen und R⁷ eine Alkylgruppe mit 1 bis 6 C-Atomen bedeutet
als Haftgrund für Lederzurichtungen.6. Use of amino group-containing polyacrylates, produced by copolymerization of
A) monomers of the general formula I containing amino groups
B) monomeric esters of the general formula II
R⁵ - CH = CR⁶ - - OR⁷
in which R⁵ and R⁶ are hydrogen or methyl groups and R⁷ is an alkyl group having 1 to 6 carbon atoms
as a primer for leather finishes.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3816103 | 1988-05-11 | ||
DE3816103A DE3816103A1 (en) | 1988-05-11 | 1988-05-11 | IMPROVED COVERAGE FOR LEATHER FACILITIES |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0341578A2 true EP0341578A2 (en) | 1989-11-15 |
EP0341578A3 EP0341578A3 (en) | 1991-09-04 |
Family
ID=6354163
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP19890108082 Withdrawn EP0341578A3 (en) | 1988-05-11 | 1989-05-05 | Priming layer for leather finishing |
Country Status (6)
Country | Link |
---|---|
US (1) | US4946471A (en) |
EP (1) | EP0341578A3 (en) |
JP (1) | JPH0218500A (en) |
BR (1) | BR8902192A (en) |
DE (1) | DE3816103A1 (en) |
TR (1) | TR24626A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994001587A1 (en) * | 1992-07-14 | 1994-01-20 | Henkel Kommanditgesellschaft Auf Aktien | New greases for leather and their use |
WO2017105918A1 (en) * | 2015-12-17 | 2017-06-22 | 3M Innovative Properties Company | Primer composition and articles made therefrom |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5709714A (en) * | 1996-03-11 | 1998-01-20 | Rohm And Haas Company | Method of treating leather with amphoteric polymers |
JP5014739B2 (en) * | 2006-02-16 | 2012-08-29 | 花王株式会社 | Soil release agent for textiles |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1094983B (en) * | 1957-04-10 | 1960-12-15 | Ciba Geigy | Process for the polymerization of basic amides of polymerizable, ª ‡, ª ‰ -unsaturated carboxylic acids |
GB2137654A (en) * | 1980-04-11 | 1984-10-10 | Roehm Gmbh | Treating pelts and leathers |
EP0278267A1 (en) * | 1987-01-26 | 1988-08-17 | Chemische Fabrik Stockhausen GmbH | Retanning process |
-
1988
- 1988-05-11 DE DE3816103A patent/DE3816103A1/en not_active Withdrawn
-
1989
- 1989-05-03 TR TR89/0377A patent/TR24626A/en unknown
- 1989-05-05 EP EP19890108082 patent/EP0341578A3/en not_active Withdrawn
- 1989-05-10 US US07/350,055 patent/US4946471A/en not_active Expired - Fee Related
- 1989-05-10 BR BR898902192A patent/BR8902192A/en unknown
- 1989-05-11 JP JP1118504A patent/JPH0218500A/en active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1094983B (en) * | 1957-04-10 | 1960-12-15 | Ciba Geigy | Process for the polymerization of basic amides of polymerizable, ª ‡, ª ‰ -unsaturated carboxylic acids |
GB2137654A (en) * | 1980-04-11 | 1984-10-10 | Roehm Gmbh | Treating pelts and leathers |
EP0278267A1 (en) * | 1987-01-26 | 1988-08-17 | Chemische Fabrik Stockhausen GmbH | Retanning process |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994001587A1 (en) * | 1992-07-14 | 1994-01-20 | Henkel Kommanditgesellschaft Auf Aktien | New greases for leather and their use |
US5567343A (en) * | 1992-07-14 | 1996-10-22 | Henkel Kommanditgesellschaft Auf Aktien | New leather oiling preparations and their use |
US5741434A (en) * | 1992-07-14 | 1998-04-21 | Henkel Kommanditgesellschaft Auf Aktien | Leather oiling preparations and their use |
WO2017105918A1 (en) * | 2015-12-17 | 2017-06-22 | 3M Innovative Properties Company | Primer composition and articles made therefrom |
CN108431162A (en) * | 2015-12-17 | 2018-08-21 | 3M创新有限公司 | Paint base composition and the product being made from it |
US10640656B2 (en) | 2015-12-17 | 2020-05-05 | 3M Innovative Properties Company | Primer composition and articles made therefrom |
CN108431162B (en) * | 2015-12-17 | 2021-03-02 | 3M创新有限公司 | Primer composition and articles made therefrom |
Also Published As
Publication number | Publication date |
---|---|
EP0341578A3 (en) | 1991-09-04 |
JPH0218500A (en) | 1990-01-22 |
TR24626A (en) | 1991-12-24 |
BR8902192A (en) | 1990-01-02 |
US4946471A (en) | 1990-08-07 |
DE3816103A1 (en) | 1989-11-23 |
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