CN103013173A - Pigment composition with anti-warping property in plastics - Google Patents
Pigment composition with anti-warping property in plastics Download PDFInfo
- Publication number
- CN103013173A CN103013173A CN2012105411063A CN201210541106A CN103013173A CN 103013173 A CN103013173 A CN 103013173A CN 2012105411063 A CN2012105411063 A CN 2012105411063A CN 201210541106 A CN201210541106 A CN 201210541106A CN 103013173 A CN103013173 A CN 103013173A
- Authority
- CN
- China
- Prior art keywords
- pigment
- plastics
- color compositions
- warpage performance
- formula
- 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.)
- Pending
Links
- 239000000049 pigment Substances 0.000 title claims abstract description 73
- 239000000203 mixture Substances 0.000 title claims abstract description 33
- 229920003023 plastic Polymers 0.000 title claims abstract description 22
- 239000004033 plastic Substances 0.000 title claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- -1 benzoglyoxaline ketone Chemical class 0.000 claims description 28
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- 239000012188 paraffin wax Substances 0.000 claims description 4
- 150000004056 anthraquinones Chemical class 0.000 claims description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 2
- 229940125904 compound 1 Drugs 0.000 claims description 2
- 229940126214 compound 3 Drugs 0.000 claims description 2
- VPWFPZBFBFHIIL-UHFFFAOYSA-L disodium 4-[(4-methyl-2-sulfophenyl)diazenyl]-3-oxidonaphthalene-2-carboxylate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC(C)=CC=C1N=NC1=C(O)C(C([O-])=O)=CC2=CC=CC=C12 VPWFPZBFBFHIIL-UHFFFAOYSA-L 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims description 2
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical class C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract description 2
- 239000004698 Polyethylene Substances 0.000 description 25
- 229920000573 polyethylene Polymers 0.000 description 25
- 239000000654 additive Substances 0.000 description 24
- 230000000996 additive effect Effects 0.000 description 24
- 238000012360 testing method Methods 0.000 description 14
- 238000000034 method Methods 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 8
- 238000001746 injection moulding Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 0 *Sc1cc(C(NC(C2=C(c3cc(Cl)cc(S*)c3)N3)=O)=C2C3=O)cc(Cl)c1 Chemical compound *Sc1cc(C(NC(C2=C(c3cc(Cl)cc(S*)c3)N3)=O)=C2C3=O)cc(Cl)c1 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 208000037656 Respiratory Sounds Diseases 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229920013820 alkyl cellulose Polymers 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 229920001887 crystalline plastic Polymers 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/004—Diketopyrrolopyrrole dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention discloses a pigment composition with anti-warping property in plastics. The pigment comprises a compound shown in the formula (1), and a derivative in which two meta-positions or two meta-positions and para-position of a benzene ring with DPP structure are substituted with long-chain alkyl, alkoxy or alkyl sulphanyl in the body pigment, thereby improving the anti-warping property of the body pigment in the plastics.
Description
Technical field
The present invention relates to a kind of for plastics without the painted color compositions of warpage.
Background technology
Warpage (warpage) is when referring to injection molding, and metamorphism, especially those partially crystalline plastics that occur are cooled off in the demoulding.Can cause thus the formation of distortion, contraction and the crackle of moulding, make the processing difficult of material.Mostly can cause the generation of warping phenomenon when using pigment dyestuff to carry out injection moulding.
There have been many domestic and international companies to propose to improve and eliminate the method for this phenomenon before.Mention among the US4889562A that the polymkeric substance at surface of pigments coating alkylcellulose improves the anti-warpage performance of pigment; Improve the anti-warpage performance of pigment among US6180694B and the US5274010A with polymkeric substance such as polyvinyl alcohol polyvinylpyrrolidones; Mention among US6409956 and the US7417154 and use acrylic acid multipolymer that surface of pigments is coated modification; Mention among the US5271759A that sodium salt, sylvite or ammonium salt with DPP pigment comes that surface of pigments is carried out modification and improve anti-warpage performance; Title complex with metals such as titanium or zirconiums among the CN1068362C comes pigment is carried out modification; The DPP pigment that the adding phenyl ring is replaced by cyano group in pigment among the US5738719 improves anti-warpage performance; Successively mentioned the long-chain derivative that in body pigment, adds DPP pigment or quinacridone among JP2004083673A, US6409956, US7417154, US2008194742, US20060052490 and the CN1509319, distinguish Alkyl sulfide ether, phenylformic acid alkyl ester, benzoyl alkylamine such as contraposition and a position at phenyl ring, the long chain quaternary of sulfonic acid improves the anti-warpage performance of body pigment.
But mostly there is also not high defective of anti-warpage performance in the technology of above-mentioned patent disclosure.
Summary of the invention
The object of the present invention is to provide a kind of color compositions that in plastics, has anti-warpage performance, the defects that exists to overcome prior art.
The color compositions that has anti-warpage performance in plastics of the present invention, principal character be, in body pigment, contains and have the compound shown in the formula 1:
Wherein:
R
1～R
10Represent respectively R
11, OR
11Or SR
11
R
11Represent the straight-chain paraffin of carbon atom numerical digit 1～30 or contain the alkane group of side chain, or the straight-chain paraffin of the carbon atom numerical digit 1～30 that replaces of halogen or contain the alkane group of side chain;
Preferably, the compound shown in the described formula 1 is:
n=1～30。
Described body pigment is DPP class, quinacridine ketone, benzoglyoxaline ketone, azo, Anthraquinones, quinophthalone class, isoindolinone or isoindoline class;
Preferably, described body pigment is Pigment red 254, Pigment red 255, Pigment red 264, Pigment red 272, pigment orange 73, pigment orange 71, Pigment Yellow 73 110, Pigment Yellow 73 109, pigment yellow 13 8, pigment yellow 13 9, pigment violet 19, pigment Violet 23, Pigment Red 207 or Pigment red 202;
The preparation method of the compound shown in the described formula 1 can be referring to the method for US7417154 bibliographical information;
Preferably, the described color compositions that has anti-warpage performance in plastics is comprised of the component of following weight percent:
Body pigment 0.01%～99.9%;
Compound 0.01%～99.9% shown in the formula 1;
Preferably, the described color compositions that has anti-warpage performance in plastics is comprised of the component of following weight percent:
Body pigment 70%～99%;
Compound 1%～30% shown in the formula 1;
Most preferred, state the color compositions that in plastics, has anti-warpage performance, formed by the component of following weight percent:
Body pigment 70%～99%;
Compound 3%～10% shown in the formula 1;
The described preparation method who has the color compositions of anti-warpage performance in plastics is simple physical mixed method, each component is mixed getting final product.
Position or position and contraposition are all replaced by the alkyl of long-chain, alkoxyl group or alkylthio between two derivative between two on the phenyl ring that in body pigment, adds the DPP structure of the present invention, thus the anti-warpage performance of body pigment in plastics improved.
Embodiment
Embodiment 1
The additive of 9.5g Pigment red 254 with the following structural formula of 0.5g (1-1) is dry mixed evenly, this mixture is being used for the painted of polyethylene board, the angularity of test polyethylene board.
（1-1）
The additive of formula (1-1) can adopt the method preparation of US7417154.
Testing method: 600g polyethylene grain and the above-mentioned pigment composition of 0.6g are mixed, granulation after 200 ℃ of dispersions in single screw extrusion machine, then Masterbatch is injection molded into the disk of the thick 2.5cm of diameter 15cm in injection moulding machine, this disk continues to be incubated 30 minutes in 90 ℃ hot water, and placed 24 hours at room temperature, repeatedly test 10 times, the depth of camber of 10 mouldings of measurement is also averaged.
Test result is as follows:
| Embodiment | Angularity/mm |
| Do not contain additive | 35.2 |
| Contain additive | 5.9 |
The result shows: the polyethylene board painted with composition of the present invention has significantly lower angularity than pure Pigment red 254 painted polyethylene boards.
Embodiment 2
To the additive of 9.7g Pigment red 254 with the following structure of 0.3g is dry mixed evenly, again this mixture is used for the painted of polyethylene board, the angularity of test polyethylene board.
The additive of formula (1-2) can adopt the method preparation of US7417154.
Testing method is with embodiment 1, and the result is as follows:
| Embodiment | Angularity/mm |
| Do not contain additive | 37.7 |
| Contain additive | 3.1 |
The result shows: the polyethylene board painted with composition of the present invention has significantly lower angularity than pure Pigment red 254 painted polyethylene boards.
Embodiment 3
To the additive of 9g Pigment Yellow 73 110 with the following structure of 1g is dry mixed evenly, again this mixture is used for the painted of polyethylene board, the angularity of test polyethylene board.
The additive of formula (1-3) can adopt the method preparation of US7417154.
Testing method is with embodiment 1, and the result is as follows:
| Embodiment | Angularity/mm |
| Do not contain additive | 31.5 |
| Contain additive | 2.9 |
The result shows: the polyethylene board painted with composition of the present invention has significantly lower angularity than pure Pigment Yellow 73 110 painted polyethylene boards.
Embodiment 4
To the additive of 9g Pigment Yellow 73 109 with the following structure of 1g is dry mixed evenly, again this mixture is used for the painted of polyethylene board, the angularity of test polyethylene board.
The additive of formula (1-4) can adopt the method preparation of US7417154.
Testing method is with embodiment 1, and the result is as follows:
| Embodiment | Angularity/mm |
| Do not contain additive | 36.1 |
| Contain additive | 5.2 |
The result shows: the polyethylene board painted with composition of the present invention has significantly lower angularity than pure Pigment Yellow 73 109 painted polyethylene boards.
Embodiment 5
To the additive of 9g pigment yellow 13 9 with the following structure of 1g is dry mixed evenly, again this mixture is used for the painted of polyethylene board, the angularity of test polyethylene board.
Additive (1-5) can adopt the method preparation of US7417154.
Testing method is with embodiment 1, and the result is as follows:
| Embodiment | Angularity/mm |
| Do not contain additive | 32.8 |
| Contain additive | 3.4 |
The result shows: the polyethylene board painted with composition of the present invention has significantly lower angularity than pure pigment yellow 13 9 painted polyethylene boards.
Embodiment 6
The additive of 9.5g pigment orange 73 with the following structure of 0.5g is dry mixed evenly, again this mixture is used for the painted of polyethylene board, the angularity of test polyethylene board.
（1-6）
Additive (1-6) can adopt the method preparation of US7417154.
Testing method is with embodiment 1, and the result is as follows:
| Embodiment | Angularity/mm |
| Do not contain additive | 40.6 |
| Contain additive | 7.3 |
The result shows: the polyethylene board painted with composition of the present invention has significantly lower angularity than pure pigment orange 73 painted polyethylene boards.
Claims (7)
1. in plastics, have the color compositions of anti-warpage performance, it is characterized in that, in body pigment, contain and have the compound shown in the formula 1:
Wherein:
R
1～R
10Represent respectively R
11, OR
11Or SR
11
R
11Represent the straight-chain paraffin of carbon atom numerical digit 1～30 or contain the alkane group of side chain, or the straight-chain paraffin of the carbon atom numerical digit 1～30 that replaces of halogen or contain the alkane group of side chain.
2. the color compositions that has anti-warpage performance in plastics according to claim 1 is characterized in that, the compound shown in the described formula 1 is:
3. the color compositions that in plastics, has anti-warpage performance according to claim 2, it is characterized in that, described body pigment is DPP class, quinacridine ketone, benzoglyoxaline ketone, azo, Anthraquinones, quinophthalone class, isoindolinone or isoindoline class.
4. the color compositions that in plastics, has anti-warpage performance according to claim 3, it is characterized in that described body pigment is Pigment red 254, Pigment red 255, Pigment red 264, Pigment red 272, pigment orange 73, pigment orange 71, Pigment Yellow 73 110, Pigment Yellow 73 109, pigment yellow 13 8, pigment yellow 13 9, pigment violet 19, pigment Violet 23, Pigment Red 207 or Pigment red 202.
5. each described color compositions that in plastics, has anti-warpage performance according to claim 1～4, it is characterized in that, the described color compositions that in plastics, has anti-warpage performance, component by following weight percent forms: body pigment 0.01%～99.9%, the compound 0.01%～99.9% shown in the formula 1.
6. each described color compositions that in plastics, has anti-warpage performance according to claim 1～4, it is characterized in that, the described color compositions that in plastics, has anti-warpage performance, component by following weight percent forms: body pigment 70%～99%, the compound 1%～30% shown in the formula 1.
7. each described color compositions that in plastics, has anti-warpage performance according to claim 1～4, it is characterized in that, state the color compositions that in plastics, has anti-warpage performance, component by following weight percent forms: body pigment 70%～99%, the compound 3%～10% shown in the formula 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012105411063A CN103013173A (en) | 2012-12-13 | 2012-12-13 | Pigment composition with anti-warping property in plastics |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012105411063A CN103013173A (en) | 2012-12-13 | 2012-12-13 | Pigment composition with anti-warping property in plastics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103013173A true CN103013173A (en) | 2013-04-03 |
Family
ID=47962303
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2012105411063A Pending CN103013173A (en) | 2012-12-13 | 2012-12-13 | Pigment composition with anti-warping property in plastics |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103013173A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104892979A (en) * | 2014-12-31 | 2015-09-09 | 先尼科化工（上海）有限公司 | Pigment composition with warping resistant property in plastic |
| CN110790995A (en) * | 2018-08-01 | 2020-02-14 | 浙江浩川科技有限公司 | Polyolefin color master batch with anti-warping performance and preparation method thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1146469A (en) * | 1995-06-15 | 1997-04-02 | 西巴-盖尔基股份公司 | Pigment compositions of diketopyrrolopyrroles |
| CN1194282A (en) * | 1996-12-02 | 1998-09-30 | 西巴特殊化学品控股有限公司 | Method for preparing pigment composition |
| JP2007266285A (en) * | 2006-03-28 | 2007-10-11 | Nippon Kayaku Co Ltd | Field effect transistor |
| JP2008078247A (en) * | 2006-09-19 | 2008-04-03 | Toyo Ink Mfg Co Ltd | Organic transistor |
| US20100032657A1 (en) * | 2006-10-12 | 2010-02-11 | Toyo Ink Mfg Co., Ltd | Organic transistor |
-
2012
- 2012-12-13 CN CN2012105411063A patent/CN103013173A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1146469A (en) * | 1995-06-15 | 1997-04-02 | 西巴-盖尔基股份公司 | Pigment compositions of diketopyrrolopyrroles |
| CN1194282A (en) * | 1996-12-02 | 1998-09-30 | 西巴特殊化学品控股有限公司 | Method for preparing pigment composition |
| JP2007266285A (en) * | 2006-03-28 | 2007-10-11 | Nippon Kayaku Co Ltd | Field effect transistor |
| JP2008078247A (en) * | 2006-09-19 | 2008-04-03 | Toyo Ink Mfg Co Ltd | Organic transistor |
| US20100032657A1 (en) * | 2006-10-12 | 2010-02-11 | Toyo Ink Mfg Co., Ltd | Organic transistor |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104892979A (en) * | 2014-12-31 | 2015-09-09 | 先尼科化工（上海）有限公司 | Pigment composition with warping resistant property in plastic |
| WO2016107184A1 (en) * | 2014-12-31 | 2016-07-07 | 先尼科化工（上海）有限公司 | Pigment composition with anti-warping property in plastics |
| JP2018501388A (en) * | 2014-12-31 | 2018-01-18 | 先尼科化工（上海）有限公司 | Pigment composition having anti-warpage properties in plastics |
| CN104892979B (en) * | 2014-12-31 | 2019-01-15 | 先尼科化工（上海）有限公司 | Color compositions in the plastic with resistance to warping energy |
| CN110790995A (en) * | 2018-08-01 | 2020-02-14 | 浙江浩川科技有限公司 | Polyolefin color master batch with anti-warping performance and preparation method thereof |
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| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| CB03 | Change of inventor or designer information |
Inventor after: Long Xiazhu Inventor after: Li Xiujuan Inventor before: Long Xiazhu |
|
| COR | Change of bibliographic data | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20130403 |
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| RJ01 | Rejection of invention patent application after publication |