CN1053125C - Polyester type ultra-dispersant agent and preparation method thereof - Google Patents
Polyester type ultra-dispersant agent and preparation method thereof Download PDFInfo
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- CN1053125C CN1053125C CN96116371A CN96116371A CN1053125C CN 1053125 C CN1053125 C CN 1053125C CN 96116371 A CN96116371 A CN 96116371A CN 96116371 A CN96116371 A CN 96116371A CN 1053125 C CN1053125 C CN 1053125C
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Abstract
The present invention discloses a super polyester type dispersant and a preparation method thereof. As the initiator and the terminator of the solvent chain part of the super dispersant are different and have four kinds of structural general formulas at right, the super dispersant not only enables solid particles to be well dispersed in strong-polar or stronger-polar organic media but also enables the solid particles to be well dispersed in medium-polar or low-polar organic media. Therefore, the needs of an industrial department in different occasions are met.
Description
The present invention relates to a kind of dispersant and preparation method thereof.
For adapt to the needs that solid particle disperses in non-aqueous media, developed a class in polymer type dispersant in recent years.One end of its molecular structure can with treat dispersed solids particle surface strong bonded, be called anchoring group, the other end and decentralized medium have good compatibility, are called solvent chain.The present polyester-type dispersant that uses, its solvent chain mainly contain poly-12-hydroxy stearic acid (being called for short 12-HSA) and poly-epsilon-caprolactone (is called for short ε-CL) two kinds.The former (as U.S.3996,059 patent), can only be used for solid particle and disperse at nonpolar or rudimentary property medium, the latter (as G.B.2,153,804 patents) also only can be used for the middle polarity medium and disperse.For the stronger decentralized medium of polarity, existing polyester-type dispersant is all powerless, perhaps dispersion effect extreme difference (show as solid particle and produce flocculation soon after disperseing by force).
The objective of the invention is to provides a kind of polyester-type dispersant with novel molecular structure for overcoming the above-mentioned defective of existing polyester-type dispersant, to satisfy the needs that solid particle disperses in strong polarizable medium.In addition, dispersant of the present invention has good dispersion effect equally in the middle polarity medium neutralizes some low polarizable medium, has extensive applicability thereby give dispersant of the present invention.
Design of the present invention is such:
In order to guarantee that dispersant of the present invention can have good dispersion effect in strong polarizable medium, the inventor finds by theory analysis and a large amount of experiments back: solvent chain is the key component that influences the hyper-dispersant dispersive property.For this solvent chain to the polyester-type dispersant improves, imagination is an initiator with unit carboxylic acid and/or unit alcohol, in the presence of catalyst, carry out ring-opening reaction clocklike with dicarboxylic acid anhydride and epoxides, make a kind of polyesters solvent chain with alternating structure, link to each other with anchoring group more under certain conditions then, form the said dispersant of the present invention.In addition, the present invention considers from being easy to industrialized angle, a kind of easy synthetic method is provided.
Main contents of the present invention:
The said polyester-type dispersant of the present invention, because the initiator of the solvent chain of dispersant part and the difference of end group, its general structure has following four kinds:
Wherein:
R
1Be C
1～C
17Alkyl; R
2Be C
1～C
18Alkyl; R
3, R
4Can be identical, also can be different, be C
2～C
6Alkyl or halo alkyl; N=1～20, m=1～500.
When dispersant is category-A structure (comprise two kinds of AI, AII, its solvent chain is the ending of end carboxyl, down together), X=OM, wherein, M is H
+, NH
4 +Or Na
+, K
+Alkali metal ion; Or X=Y-Z, wherein Y be bridging group because of, as-NH-,
,-O-etc., Z is an organic amine, the residue of organic ammonium salt or quaternary ammonium salt;
When (comprise two kinds of BI, BII, its solvent chain is terminal hydroxy group ending, down with), X is phosphate radical (or ester), sulfate radical (or ester), or X=Q-Z when dispersant is the category-B structure, and wherein Q is a bridged group, as
, Z is an organic amine, the residue of organic amine salt or quaternary ammonium salt.
The preparation method of dispersant of the present invention:
At first want the synthetic chain, promptly synthetic terminal carboxyl polyester (having the category-A structure) or hydroxyl telechelic polyester (having the category-B structure), concrete building-up process such as following:
Because initiator can be unit carboxylic acid and/or unit alcohol (they also are simultaneously the molecular weight regulators in the building-up process), in the presence of catalyst, add thermal response with dicarboxylic acid anhydride and epoxides and make, two alternation response groups (with I, II is expressed as follows) are arranged in its course of reaction:
If with the unit carboxylic acid is initiator, then course of reaction is pressed I → II → I → II ... carry out; If with unit alcohol is initiator, then course of reaction is pressed II → I → II → I ... carry out.In the reactant mixture if the excessive terminal carboxyl polyester that then obtains of acid anhydrides, with the dispersant that obtains the category-A general formula after anchoring group links to each other; If epoxides is excessive in the reactant mixture, then obtain hydroxyl telechelic polyester, with the dispersant that obtains the category-B general formula after anchoring group links to each other.
Adjustable factor is as follows in the building-up process:
(1) adopts mixed acid anhydride or hybrid ring oxidation thing, regulate between the different acid anhydrides simultaneously or the rate of charge between the different rings oxide, can change the structure and the polarity of solvent chain easily, the dispersant of final formation can be disperseed in the organic media of opposed polarity efficiently.Suitable dicarboxylic acid anhydride has maleic anhydride, succinyl oxide, tetrabydrophthalic anhydride, chlorendic anhydride, PHT4 etc.; Suitable epoxides has expoxy propane, oxirane, epoxychloropropane, epoxy bromopropane etc.
(2) change the consumption of initiator, can regulate the molecular weight of solvent chain.The number-average molecular weight Mn of solvent chain equals the gross weight (gram) of real reaction thing and the ratio of the molal quantity of initiator in theory.The actual molecular weight of solvent chain can be calculated by the acid number (Av) and the hydroxyl value (Hv) of assaying reaction system.Computing formula is: Mn=56100/ (Av+Hv).
(3) the solvent chain synthesis reaction temperature should be controlled between 110 ℃～130 ℃.Used catalyst can be tertiary amine or quaternary ammonium salt when synthetic, and as triethylamine, benzyl triethyl ammonium ammonium chloride, TBAB etc., its consumption is 0.1%～1.0% (wt%) of reactant gross weight.
(4) synthetic reaction can be carried out under normal pressure, and this moment, epoxides should add with the dropping mode; Synthetic reaction also can be pressurizeed and be carried out, and this moment, epoxides dropped in the reactor by rate of charge with other reactants.
(5) because being connected between solvent chain and the anchoring group, in fact be exactly carboxyl or hydroxyl with polar group between be connected, its reaction condition is different with the difference of polar group, but these reactions all are ripe classics reactions.For example the reaction between terminal carboxyl polyester and primary amine or the secondary amine can be carried out between 120～160 ℃, and the extent of reaction can be judged according to the acid number of product, specifically not give unnecessary details among the present invention for this reason.Only be summarized as follows below with regard to connected mode between solvent chain and the anchoring group and corresponding product:
(1) terminal carboxyl polyester can directly use as dispersant, also can generate with NH with ammonia, alkali metal oxide or hydroxide effect
4 +Or alkali metal ion is (as Na
+, K
+) be the dispersant (A-1) of anchoring group;
Terminal carboxyl polyester can be that alcamines material (as the triethanolamine) reaction of tertiary amine forms with the organic amine with polyamine or amido also is the dispersant (A-2) of anchoring group, and it be the dispersant (A-3) of anchoring group that this dispersant can also further generate with amine salt or quaternary ammonium salt with alkylating reagents reactions such as acid (comprising mineral matter, organic acid) or sulfuric acid dialkyls;
(2) hydroxyl telechelic polyester can with inorganic anhydrides material (as P
2O
5Deng) to generate end group be the dispersant (B-1) of acid group or its ester in reaction; Also can be earlier and excessive polyisocyanates reaction, and then with polyamine or alcamines substance reaction, generation is the dispersant (B-2) of anchoring group with the organic amine, and it is the dispersant (B-3) of anchoring group that this dispersant also can further generate with amine salt or quaternary amine with acid or alkylating reagent reaction;
Above-mentioned said dispersant, its structural formula can be with following various description, and wherein swash is partly represented the polyester-type solvent chain:
Wherein: M is H
+, MH
4 +Or Na
+, K
+Alkali metal ion.
Wherein: a is O, and NH, or NR group, R are C
1～C
18Alkyl,
B is C
1～C
18Alkyl,
C, d are H or C
1～C
18Alkyl, the two can be identical, can also be different.
Wherein: all with the explanation of (A-2), e is H or C for a, b, c, d
1～C
18Alkyl, F
-Be anion, as CH
3SO
4 -, Cl
-Deng.
Wherein: X be acid group or and ester, as phosphate radical (ester), sulfate radical (ester).
Wherein: a, b, c, d is with the explanation of (A-2), and G is C
1～C
18Alkyl, m=1～500.
Wherein, a, b, c, d, e, F illustrate with (A-3) that all G, m are with (B-2) explanation.
The dispersant that makes according to the method described above, when practical application, its optimum amount depends on the specific area (BET) of dispersed solid particle.Usual amounts can be at 0.5～5.0mg/M
2Choose in the scope, the optimum amount scope is 1.0～2.0mg/M
2When other factors is constant (certain as solid particle, solvent one is regularly), by investigating the variation relation of dispersion viscosity with dispersant dosage, can be in the hope of the use amount of optimum dispersant, when optimum amount, the viscosity of dispersion is minimum usually.Point out in passing in addition, when using dispersant of the present invention, should earlier dispersant be dissolved in decentralized medium, and then add solid particle and disperse (forming stable dispersion).
Further illustrate content of the present invention below in conjunction with embodiment.
Embodiment 1
In a 500ml four-hole boiling flask that has mechanical agitation, heating control apparatus, cooling and reflux device and a balance addition funnel, add caproic acid 23.2g (0.2mol) earlier, maleic anhydride 176.4g (1.8mol), benzyltriethylammoinium chloride (catalyst) 1.0 grams, 120 ℃ of heat temperature raisings, drip expoxy propane then, until the acid number A of reaction system
v=0, vacuumize and remove remaining expoxy propane, get hydroxyl telechelic polyester, its number-average molecular weight Mn=1578 adds maleic anhydride 19.6g (0.2mol) again, continues to react to acid number A under 120 ℃
v=33.0 hydroxyl value H
v=0.5, get terminal carboxyl polyester, its number-average molecular weight Mn=1676.This terminal carboxyl polyester is one of a kind of dispersant of the present invention (having AI general formula molecular structure), n=10 wherein, m=1 (being called for short hyper-dispersant A-1).
Embodiment 2
Make terminal carboxyl polyester according to embodiment 1 identical method, under 80 ℃, adding concentration is that (BASF AG produces 50% polyethyleneimine: amine aqueous solution, and the trade mark is polymin P, and molecular weight is 5 * 10 then
4) 24.0g, dimethylbenzene 45ml, and after loading onto oil water separator (changing addition funnel), (dimethylbenzene and water azeotropic steamed in the course of reaction in 10 hours in heat temperature raising to 120 a ℃ following reaction again, the layering in oil water separator of cooling back, water is directly emitted, dimethylbenzene returns in the flask reactor of four-hole and recycles), vacuumize at last except that removal xylene, (molecular structure with general formula AI n=10), records acid number A to obtain another dispersant of the present invention
v=18.2, calculate m=380 (being called for short dispersant A-2) according to the degree of the amidation process of the molecular weight of polymine and carboxyl.Because responseless part still keeps the molecular structure of dispersant A-1 in the reactant, therefore, dispersant A-2 is actually a kind of mixture that contains dispersant A-1.
Embodiment 3
Mechanical agitation is being housed, heating and temperature controlling device, cooling and reflux device is in the 500ml four-hole boiling flask of profit and separator, add dispersant A-1 335 gram (0.2mol), dimethylbenzene 40 grams, N, N-dimethyl-1,3-propane diamine 25.0 grams, add thermal response 6 hours in 160 ℃, vacuumize and remove dimethylbenzene and unnecessary organic amine, must hold the tertiary amine groups polyester.Be cooled to 50 ℃, add dimethyl suflfate 25.2 grams, system is warming up to 90 ℃ automatically, 95 ℃ of insulations 2 hours, must hold the quaternary ammonium salt base polyester, and its number-average molecular weight is 1881, has the AI formula, n=10, and m=1 abbreviates dispersant A-3 as.
Embodiment 4
Get the P that adds equivalent in embodiment 1 resulting hydroxyl telechelic polyester 315.6 grams
2O
514.2 gram, 90 ℃ down reaction kept 20 hours, must hold phosphate-basedly, polyester has BI general formula quasi-molecule structure, n=10, m=1 is called for short dispersant B-1.
Embodiment 5
Get in embodiment 1 resulting hydroxyl telechelic polyester 157.8 grams, the toluene wiring solution-forming that adds same weight, the toluene di-isocyanate(TDI) (TDI) of 2.05 times of equivalents of adding is warming up to 80 ℃ of reactions two hours then, be cooled to room temperature, add 102 gram N, N-dimethyl-1,3-propane diamine, obtain having the toluene solution of the dispersant of BI general formula quasi-molecule structure, abbreviate dispersant B-2 as, n=10 wherein, m=1.
Embodiment 6
In embodiment 5 resulting hyper-dispersant B-2, add 12.6 gram dimethyl suflfates, system will heat up automatically, keep 2hr at 95 ℃, obtain having the dispersant of BI general formula quasi-molecule structure, abbreviate dispersant B-3 as.
The initiator caproic acid that synthetic chain among the embodiment 1～6 is used changes equimolar laruyl alcohol into, and reaction condition is constant, and the dispersant that obtains then becomes AII formula structure by corresponding AI formula structure, and BI formula structure becomes BII formula structure, for example:
Embodiment 7
Except 23.2 acid of restraining oneself are changed into the 37.2 gram laruyl alcohols, the preparation method of hydroxyl telechelic polyester is all with embodiment 1, drips propylene oxide reactions down to acid number A at 120 ℃
v=0, get hydroxyl telechelic polyester.Be cooled to 60 ℃ then, add 14.2 gram P again
2O
5, in 90 ℃ of down reactions 20 hours, must hold phosphate-based polyester, have BII general formula quasi-molecule structure, abbreviate dispersant B-4 as, n=10 wherein, m=1.
Embodiment 8
At first prepare terminal carboxyl polyester by embodiment 1 similar methods, wherein except with 23.2 restrain oneself acid change into 37.2 the gram laruyl alcohols, remaining proportioning and method all with embodiment 1, obtain terminal carboxyl polyester; Press the same method of embodiment 2 then, promptly add 24.0g polymin P and 45ml dimethylbenzene, under 120 ℃, react to A
V=16.0, the dispersant that obtains having AII formula structure at last, n=10 wherein, m=417 abbreviates dispersant A-4 as.
Above-mentioned dispersant effect is exemplified below:
(1) gets in the 191 type unsaturated polyester (UP) resins that dispersant A-1 0.5g that makes according to embodiment 1 is dissolved in 49.5g, add 50gAl (OH) then
3Fire-retardant filler (average grain diameter is 8 μ) stirs, and recording viscosity with NDJ-79 type viscosimeter is 2.10PaS;
If without dispersant, only, add 50gAl (OH) then with 50g 191 type unsaturated polyester (UP) resins
3Fire-retardant filler (particle mean size is 8 μ) stirs, and recording viscosity with above-mentioned same viscosimeter is 3.50PaS, not only viscosity height, and system instability, very fast generation Al (OH)
3Precipitation.
(2) get dispersant A-2 0.4g that makes according to embodiment 2, vinyl chloride-vinyl acetate-vinyl alcohol copolymer thing 1.06g after toluene-cyclohexanone-butanone mixed solvent (mixing by 2: 2: 6 volume ratios) 5.4g mixes, adds cobalt improved γ-Fe
2O
3Magnetic 8.0g (a kind of super-fine magnetic powder), ground 2 hours with quick grinding dispersion machine, add polyurethane resin solution 12.1g then and (wherein contain polyurethane resin 1.06g, toluene-cyclohexanone-butanone mixed solvent 11.04g), ground again 2 hours, the magnetic paint viscosity of gained is 0.22PaS (used viscosimeter is the same, is omitted when narrating later on), and recording the squareness ratio that characterizes the magnetic dispersive property after the coating is 0.88; As the alkylbenzene APEO dispersant RE-610 that produces of the GAFC company that uses above-mentioned same amount, obtaining magnetic paint by above-mentioned identical proportioning and method of operating, its corresponding viscosity is 0.26pa..s, squareness ratio is 0.83; And for example by above-mentioned same consumption and proportioning and method, only dispersant changes patent GB.2 into, 153,804 examples, 2 described dispersants, and the magnetic paint of acquisition, its viscosity is 0.25PaS, squareness ratio is 0.85.Therefore dispersant A of the present invention-2 all is better than prior art.
(3) get by in the ethanolic solution of embodiment 3 prepared dispersant A-3 1.0g adding 29g polyamide (concentration is 10%), add iron oxide yellow pigments 70g again, ground 1.2 hours with quick grinding dispersion machine, obtain a kind of uniform and stable iron oxide yellow pigments slurry, its viscosity is 0.12PaS; If use patent GB.2, disclosed dispersant in 153,804 examples 2 mixes according to above-mentioned identical proportioning, and ground 2.0 hours, reach qualified fineness after, recording viscosity is 0.15PaS, and the iron oxide yellow pigments of gained slurry is unstable, easily flocculation; If be made into coating with above-mentioned two kinds of iron oxide yellow slurries, the former gloss and degree of staining all are better than the latter, and this proves absolutely that dispersant A of the present invention-3 dispersion effect in polar solvent is better than prior art, so the wide industrial development prospect is arranged.
(4) get dispersant B-2 2.0g by embodiment 5 gained, be dissolved in the acetone of 80g, add carbon black (average grain diameter is 25nm) 20g again, ground 2 hours with speed muller, it is 0.05PaS that the gained slurry records viscosity; And use GB.2, and the dispersant described in 153, the 804 patent examples 2, according to the slurry that above-mentioned identical proportioning and method grind to form, the viscosity that records is 0.2PaS, visible dispersant of the present invention has in intensive polar solvent than the better dispersion effect of existing technology.
(5) get embodiment 6 prepared dispersant B-3 0.4g, vinyl chloride-vinyl acetate-vinyl alcohol copolymer thing 1.06g, toluene-cyclohexanone-butanone (by 2: 2: 6 volume ratio preparation) mixed solvent 5.84g, cobalt improved ultra-fine γ-Fe
2O
3Magnetic 8.0g, place quick grinding dispersion machine to disperse 2 hours, and then adding polyurethane solutions 12.1g (wherein contains polyurethane resin 1.06g, toluene-cyclohexanone-butanone mixed solvent 11.04g), grind again and disperseed 2 hours, gained magnetic paint viscosity is 0.24PaS, and recording the squareness ratio that characterizes the magnetic dispersive property after the coating is 0.88; As use the RE-610 dispersant of prior art, and to disperse according to above-mentioned same proportioning and method, the viscosity of gained magnetic paint is 0.26PaS, and squareness ratio is 0.83, and visible dispersant of the present invention is better than prior art.
(6) get 7 prepared dispersant B-4 1.7g by embodiment, cyclohexanone 18g, polyurethane resin 2.0g wiring solution-forming adds TiO again
2Pigment 80g disperseed 2 hours grinding in the dispersion machine fast, the gained graining paste viscosity be 0.31PaS; If use the GB.2 of same amount, the dispersant of describing in 153, the 804 patent examples 2 disperses after the same method, and the viscosity of gained graining paste is 0.42PaS, and visible dispersant of the present invention is better than prior art.
(7) get 4 obtained dispersant B-1 1.2g, be dissolved in the 50g191 type unsaturated polyester (UP) resin, add Al (OH) again by embodiment
350g (ultra-fine Al (OH)
3Average grain diameter be 8 μ), after stirring, the viscosity of gained slurry is 2.6PaS; If use existing RE-610 dispersant, to disperse according to same proportioning and method, the viscosity of gained slurry is 3.1PaS; If do not use any dispersant, the viscosity of surveying the gained slurry is 3.5PaS, and very easily coagulative precipitation.The remarkable excellent prior art that has of the effect of visible in sum its dispersion of dispersant of the present invention has the vast market development prospect.
Claims (5)
1. a polyester-type dispersant is made of solvent chain and anchoring group, it is characterized in that: (1) said dispersant has following four kinds of general structures:
Wherein: R
1Be C
1～C
17Alkyl, R
2Be C
1-C
18Alkyl, R
3Be C
1～C
6Alkyl or halo alkyl, n=1～20, m=1～150;
(2) when dispersant is A I or AII class formation, X is OM or X=Y-Z,
Wherein:
M is H
+, MH
4 +Or Na
+, K
+Alkali metal ion,
Y is-NH-,
Or-O-,
Z is an organic amine, the residue of organic amine salt or quaternary amine;
(3) when dispersant is BI or BII class formation, X is phosphate radical (ester), sulfate radical (ester) or X=Q-Z;
Q is:
Z is an organic amine, the residue of organic amine salt or quaternary amine.
2. the preparation method of dispersant as claimed in claim 1 is formed by connecting by solvent chain and anchoring group, it is characterized in that:
(1), in the presence of catalyst, adds thermal response, the acquisition solvent chain with excessive dicarboxylic acid anhydride, epoxides with unit carboxylic acid or unit alcohol initiator; Reaction temperature is 110 ℃～130 ℃, and reaction pressure is normal pressure or pressurization;
(2) with the solvent chain and the ammonia that are obtained, or alkali metal hydroxide, or the alkali metal oxide reaction, or polyamine, or hydramine, or acid or alkylating reagent reaction, the dispersant shown in formula AI or the AII obtained;
Said unit carboxylic acid is C
2～C
18Carboxylic acid, said unit alcohol is C
1～C
18Alcohol, said catalyst is tertiary amine or quaternary amine, its consumption is 0.1%～1.0% (wt) of reaction-ure mixture, and said dicarboxylic acid anhydride is a kind of in maleic anhydride, succinyl oxide, phthalic anhydride, tetrabydrophthalic anhydride, chlorendic anhydride or the PHT4; Said epoxides is a kind of in oxirane, expoxy propane, epoxychloropropane or the epoxy bromopropane.
3. preparation method as claimed in claim 2 is characterized in that:
(1) said solvent chain is with unit carboxylic acid or unit alcohol initiator, adds thermal response with dicarboxylic acid anhydride, excessive epoxides and obtain in the presence of catalyst;
(2) with the solvent chain elder generation and excessive isocyanate reaction that are obtained, and then and polyamine, or hydramine, or acid or alkylating reagent reaction, the dispersant shown in formula BI or the BII obtained.
4. preparation method as claimed in claim 3 is characterized in that: the direct and inorganic acid anhydride reactant with the solvent chain that is obtained obtains the dispersant shown in formula BI or the BII.
5. as claim 2, or 3, or 4 described preparation methods, it is characterized in that: said catalyst is triethylamine, Bian TEBA or TBAB.
Priority Applications (1)
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|---|---|---|---|
| CN96116371A CN1053125C (en) | 1996-05-27 | 1996-05-27 | Polyester type ultra-dispersant agent and preparation method thereof |
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|---|---|---|---|
| CN96116371A CN1053125C (en) | 1996-05-27 | 1996-05-27 | Polyester type ultra-dispersant agent and preparation method thereof |
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| CN1053125C true CN1053125C (en) | 2000-06-07 |
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| JP4396777B2 (en) * | 2006-07-14 | 2010-01-13 | 東洋インキ製造株式会社 | Polyester dispersant, process for producing the same, and pigment composition using the same |
| CN101353421B (en) * | 2008-09-17 | 2010-12-08 | 武汉工程大学 | Polyester type hyperbranched polymer pigment dispersant and preparation thereof |
| CN102746501B (en) * | 2012-06-21 | 2014-08-13 | 上海核心新材料科技有限公司 | Manufacturing method of dispersant and dispersant |
| CN103626989A (en) * | 2013-05-20 | 2014-03-12 | 华东理工大学 | Preparation method for polyphosphoester viscosity-reducing dispersant for inorganic flame-retardant unsaturated resin |
| CN107022182A (en) * | 2017-05-17 | 2017-08-08 | 华东理工大学 | A kind of inorganic nano flame-retardance unsaturated resin composite and preparation method thereof |
| CN109796363B (en) * | 2018-12-06 | 2020-12-22 | 华南理工大学 | Polyhydroxy low-viscosity star-shaped hydroxyl resin with hybrid arms and preparation method and application thereof |
| KR20220139943A (en) * | 2020-03-25 | 2022-10-17 | 디아이씨 가부시끼가이샤 | Inorganic filler dispersion stabilizer, inorganic filler-containing resin composition, molded article and additive |
| CN112852301B (en) * | 2021-01-05 | 2022-03-15 | 中国第一铅笔有限公司 | Photosensitive color-changing pencil paint and process for producing photosensitive color-changing pencil by using same |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0240160A2 (en) * | 1986-03-26 | 1987-10-07 | Imperial Chemical Industries Plc | Composition comprising fine ceramic particles and an organic dispersant |
| EP0375184A2 (en) * | 1988-12-22 | 1990-06-27 | Imperial Chemical Industries Plc | Composition and use |
| EP0401790A2 (en) * | 1989-06-06 | 1990-12-12 | Plüss-Staufer AG | Highly concentrated aqueous slurry of minerals and/or fillers and/or pigments |
| EP0582928A2 (en) * | 1992-08-11 | 1994-02-16 | Hoechst Aktiengesellschaft | Surface active compounds based on modified castor oil fatty substances |
-
1996
- 1996-05-27 CN CN96116371A patent/CN1053125C/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0240160A2 (en) * | 1986-03-26 | 1987-10-07 | Imperial Chemical Industries Plc | Composition comprising fine ceramic particles and an organic dispersant |
| EP0375184A2 (en) * | 1988-12-22 | 1990-06-27 | Imperial Chemical Industries Plc | Composition and use |
| EP0401790A2 (en) * | 1989-06-06 | 1990-12-12 | Plüss-Staufer AG | Highly concentrated aqueous slurry of minerals and/or fillers and/or pigments |
| EP0582928A2 (en) * | 1992-08-11 | 1994-02-16 | Hoechst Aktiengesellschaft | Surface active compounds based on modified castor oil fatty substances |
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| CN1146371A (en) | 1997-04-02 |
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