CN103897160B - A kind of special unsaturated polyester resin of for shelf-stable cloud stone glue - Google Patents
A kind of special unsaturated polyester resin of for shelf-stable cloud stone glue Download PDFInfo
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- CN103897160B CN103897160B CN201210569179.3A CN201210569179A CN103897160B CN 103897160 B CN103897160 B CN 103897160B CN 201210569179 A CN201210569179 A CN 201210569179A CN 103897160 B CN103897160 B CN 103897160B
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Abstract
The invention provides a kind of special unsaturated polyester resin of for shelf-stable cloud stone glue, belong to adhesive area.It is an object of the invention to provide the unsaturated-resin of a kind of long shelf-life, Heat stability is good, be exclusively used in the production of cloud stone glue.It is characterized in that: the weight portion of its constitutive material is: dicyclopentadiene 85-115 part, unsaturated dicarboxylic acid anhydride 75-95 part, monounsaturated dicarboxylic acid acid anhydride 100-140 part, water 18-23 part, dihydroxylic alcohols 100-150 part, styrene 90-200 part, polymerization inhibitor 0.1-0.6 part, accelerator 0.2-1 part, catalyst 0-1.5 part, antioxidant 0-2 part and ultraviolet-resistant absorbent 0-0.2 part, this product can reach more than 3 years in room temperature (25 DEG C) the lower shelf-life, and under 110 DEG C of conditions heat stability more than 10 hours.
Description
Technical field
The present invention relates to adhesive area, be specifically related to a kind of special unsaturated polyester resin improving cloud stone glue storge quality.
Background technology
Unsaturated polyester resin is one the most frequently used in thermosetting resin, it it is the main raw material(s) producing cloud stone glue, unsaturated-resin is of a great variety, unsaturated-resin for producing cloud stone glue is different according to its kind, its viscosity, gel time, exothermic peak, cured later and heat stability etc. have bigger difference.The shelf life of products of cloud stone glue is to evaluate the important evidence of its quality, its shelf-life depends primarily on unsaturated-resin used, at present the shelf-life of cloud stone glue unsaturated-resin is not from 3 months to 6 months etc. on the market, make troubles to use procedure, and study at present and focus mostly in toughness and the adhesion strength etc. that improve cloud stone glue, it is CN201110043873.7 such as the patent No. and the patent No. is CN201010111689.7, rarer for the correlational study extending the cloud stone glue shelf-life.
Summary of the invention
It is an object of the invention to provide the unsaturated-resin of a kind of long shelf-life, Heat stability is good, be exclusively used in the production of cloud stone glue.
Technical scheme is as follows:
A kind of special unsaturated polyester resin of for shelf-stable cloud stone glue, it is characterised in that: the weight portion of its constitutive material is:
Dicyclopentadiene 85-115
Unsaturated dicarboxylic acid anhydride 75-95
Monounsaturated dicarboxylic acid acid anhydride 100-140
Water 18-23
Dihydroxylic alcohols 100-150
Styrene 90-200
The mass fraction of other materials used is:
Polymerization inhibitor 0.1-0.6
Accelerator 0.2-1
Catalyst 0-1.5
Antioxidant 0-2
Ultraviolet-resistant absorbent 0-0.2
The described special unsaturated polyester resin of for shelf-stable cloud stone glue, it is characterised in that the purity of described dicyclopentadiene is 70%-100%；
The described special unsaturated polyester resin of for shelf-stable cloud stone glue, it is characterised in that described unsaturated dicarboxylic acid anhydride include maleic anhydride, fumaric acid acid anhydride one or both；Described monounsaturated dicarboxylic acid acid anhydride includes phthalic anhydride, M-phthalic acid, p-phthalic acid, one or more of adipic acid；Described saturated dihydroxylic alcohols include ethylene glycol, diethylene glycol, propylene glycol one or more；Described polymerization inhibitor includes adjacent methyl hydroquinone, 2,5 di-tert-butyl hydroquinones, tert-butylhydroquinone, one or more of methyl hydroquinone；Described accelerator includes DMA, N, N dimethyl para-totuidine, N, N-diisopropanol para-totuidine, cobalt naphthenate, one or more of cobalt iso-octoate；Described catalyst includes phosphoric acid, phosphorous acid, sulphuric acid, one or more of benzyltriethylammoinium chloride；Described antioxidant includes triphenyl phosphite, NSC 5284, one or more of 2,6 ditertbutylparacresols；Described ultraviolet-resistant absorbent includes titanium dioxide, one or both of phenyl salicylate；
The preparation method of the described special unsaturated polyester resin of for shelf-stable cloud stone glue is: by weight by the dicyclopentadiene of 85-115 part purity 70% ~ 100%, 75-95 part unsaturated dicarboxylic acid anhydride, 18 ~ 23 parts of water, hydrolysis 3h at 110 ~ 115 DEG C, it is subsequently adding 100-140 part monounsaturated dicarboxylic acid acid anhydride, 100-150 part dihydroxylic alcohols is at catalyst, antioxidant, in 130 ~ 200 DEG C when, esterification dehydration is carried out under the existence of polymerization inhibitor, reaction utilizes vacuum pump evacuation polycondensation when being 50-60mg/KOH to acid number, react to acid number 28 ~ 32mg/KOH and release vacuum and be cooled to 120 DEG C, it is diluted in 100 ~ 140 parts of styrene, it is eventually adding accelerator, polymerization inhibitor, ultraviolet-resistant absorbent.
Above-mentioned each material all can be commercially available in market.
The special unsaturated polyester resin of for shelf-stable cloud stone glue of the present invention is except can reaching the performances such as the cohesive force of resins for universal use, gel time, measure according to physical holding of the stock and be published in " assessment of unsaturated-resin storage period " on " thermosetting resin " magazine with nineteen ninety or the assessment of dependent evaluation method that 01 phase in 2003 is published in " mensuration of UPR gel time and the phase of the storage " article in " synthetic resin and plastics ", our factory research and development resin can reach more than 3 years in room temperature (25 DEG C) the lower shelf-life, and under 110 DEG C of conditions heat stability more than 10 hours.
Detailed description of the invention
The present invention is further illustrated by the examples below with comparative example.
Embodiment 1
The raw material components part by weight of the special unsaturated polyester resin of for shelf-stable cloud stone glue is:
Dicyclopentadiene 110(purity 80%)
Maleic anhydride 85
Phthalic anhydride 125
Water 23
Ethylene glycol 28
Propylene glycol 34
Diethylene glycol 63
Styrene 90
Adjacent methyl hydroquinone 0.1
N, N-dimethyl-p-toluidine 1
Phosphoric acid 0.1
Triphenyl phosphite 1
Titanium dioxide 0.1
By above-mentioned part by weight, dicyclopentadiene, maleic anhydride, water are reacted at 110 DEG C 3h, be subsequently adding phthalic anhydride, ethylene glycol, diethylene glycol, propylene glycol phosphoric acid, triphenyl phosphite, adjacent methyl hydroquinone existence under in 200 DEG C when carry out esterification dehydration, evacuation polycondensation when reaction to acid number is 60mg/KOH, react to acid number 32mg/KOH and release vacuum and be cooled to 120 DEG C, it is diluted in styrene, it is eventually adding N, N-dimethyl-p-toluidine, adjacent methyl hydroquinone, titanium dioxide.
Obtained unsaturated polyester resin:
| 80 DEG C of reactivities | 18.2 the second |
| 80 DEG C of heat stability (GB 24 hours) | 20 days without significant change |
| 25 DEG C of gel times | 5 points 5 seconds |
| 110 DEG C of heat stability (company standard) | 12h is without significant change |
Embodiment 2
The raw material components part by weight of the special unsaturated polyester resin of for shelf-stable cloud stone glue is:
Dicyclopentadiene 100(purity 85%)
Maleic anhydride 90
Phthalic anhydride 136
Water 18
Diethylene glycol 104
Ethylene glycol 40
Styrene 200
Adjacent methyl hydroquinone 0.3
Cobalt naphthenate 0.3
Phosphorous acid 1
Triphenyl phosphite 1
Ultraviolet-resistant absorbent 0
By above-mentioned part by weight, dicyclopentadiene, maleic anhydride and water are reacted at 115 DEG C 3h, be subsequently adding phthalic anhydride, diethylene glycol, ethylene glycol phosphorous acid, triphenyl phosphite, adjacent methyl hydroquinone existence under in 130 DEG C when carry out esterification dehydration, evacuation polycondensation when reaction to acid number is 50mg/KOH, react to acid number 28mg/KOH and release vacuum and be cooled to 120 DEG C, it is diluted to dissolved with N, in the styrene of N-diisopropylamine para-totuidine, it is eventually adding cobalt naphthenate, adjacent methyl hydroquinone.
Obtained unsaturated polyester resin:
| 80 DEG C of reactivities | 19.6 the second |
| 80 DEG C of heat stability (GB 24 hours) | 20 days without significant change |
| 25 DEG C of gel times | 4 points 58 seconds |
| 110 DEG C of heat stability (company standard) | 12 hours without significant change |
Embodiment 3
The raw material components part by weight of the special unsaturated polyester resin of for shelf-stable cloud stone glue is:
Dicyclopentadiene 90(purity 95%)
Maleic anhydride 78
M-phthalic acid 100
Water 21
Propylene glycol 18
Ethylene glycol 22
Diethylene glycol 63
Styrene 120
Adjacent methyl hydroquinone 0.6
DMA 1
Sulphuric acid 1.5
2,6 ditertbutylparacresols 2
Phenyl salicylate 0.2
By above-mentioned part by weight, dicyclopentadiene, maleic anhydride, water are reacted at 113 DEG C 3h, be subsequently adding M-phthalic acid, propylene glycol, ethylene glycol, diethylene glycol sulphuric acid, 2,6 ditertbutylparacresols, adjacent methyl hydroquinone existence under in 175 DEG C when, carry out esterification dehydration, evacuation polycondensation when reaction to acid number is 55mg/KOH, react to acid number 30mg/KOH and release vacuum and be cooled to 120 DEG C, it is diluted in styrene, it is eventually adding DMA, methyl hydroquinone, phenyl salicylate.
Obtained unsaturated polyester resin:
| 80 DEG C of reactivities | 17.8 the second |
| 80 DEG C of heat stability (GB 24 hours) | 20 days without significant change |
| 25 DEG C of gel times | 5 points 15 seconds |
| 110 DEG C of heat stability (industry standard) | 12 hours without significant change |
Comparative example 1
The raw material components part by weight of the special unsaturated polyester resin of for shelf-stable cloud stone glue is:
Dicyclopentadiene 200(purity 80%)
Maleic anhydride 100
Phthalic anhydride 20
Water 20
Ethylene glycol 50
Styrene 90
Adjacent methyl hydroquinone 1
Cobalt iso-octoate 1.5
Phosphoric acid 2
Triphenyl phosphite 2.5
Titanium dioxide 0.5
By above-mentioned part by weight, by dicyclopentadiene, maleic anhydride, water hydrolysis 3h at 110 DEG C, be subsequently adding phthalic anhydride and ethylene glycol phosphoric acid, triphenyl phosphite, adjacent methyl hydroquinone existence under in 200 DEG C when carry out esterification dehydration, evacuation polycondensation when reaction to acid number is 43mg/KOH, react to acid number 32mg/KOH and release vacuum and be cooled to 120 DEG C, it is diluted in styrene, is eventually adding cobalt iso-octoate, adjacent methyl hydroquinone, titanium dioxide.
Obtained unsaturated polyester resin:
| 80 DEG C of reactivities | 600 seconds 4--> |
| 80 DEG C of heat stability | 48h |
| 25 DEG C of gel times | 28 points 35 seconds |
| 110 DEG C of heat stability (company standard) | 2.5 hours gels |
Comparative example 2
The raw material components part by weight of the special unsaturated polyester resin of for shelf-stable cloud stone glue is:
Dicyclopentadiene 100(purity 85%)
Fumaric acid acid anhydride 90
Monounsaturated dicarboxylic acid acid anhydride 0
Water 18
Diethylene glycol 80
Styrene 60
Methyl hydroquinone 1.5
Cobalt naphthenate 2
Phosphorous acid 3
NSC 5284 3
Titanium dioxide 0.8
By above-mentioned part by weight, by dicyclopentadiene, fumaric acid acid anhydride and water hydrolysis 3h at 140 DEG C, be subsequently adding diethylene glycol phosphorous acid, NSC 5284, methyl hydroquinone existence under in 100 DEG C when carry out esterification dehydration, evacuation polycondensation when reaction to acid number is 38mg/KOH, react to acid number 28mg/KOH and release vacuum and be cooled to 120 DEG C, it is diluted in styrene, is eventually adding cobalt naphthenate, methyl hydroquinone, titanium dioxide.
Obtained unsaturated polyester resin:
| 80 DEG C of reactivities | 18 points 48 seconds |
| 80 DEG C of heat stability | 24h |
| 25 DEG C of gel times | 60 points 5 seconds |
| 110 DEG C of heat stability (company standard) | 3 hours gels |
Comparative example 3
The raw material components part by weight of the special unsaturated polyester resin of for shelf-stable cloud stone glue is:
Dicyclopentadiene 120
Maleic anhydride 110
Isophthalic anhydride 30
Water 21
Propylene glycol 75
Styrene 80
Methyl hydroquinone 1.2
DMA 1.2
Sulphuric acid 2
2,6 ditertbutylparacresols 2.5
Phenyl salicylate 0.5
By above-mentioned part by weight, by dicyclopentadiene, maleic anhydride, water hydrolysis 3h at 113 DEG C, be subsequently adding M-phthalic acid and propylene glycol sulphuric acid, 2,6 ditertbutylparacresols, adjacent methyl hydroquinone existence under in 175 DEG C when, carry out esterification dehydration, evacuation polycondensation when reaction to acid number is 35mg/KOH, react to acid number 25mg/KOH and release vacuum and be cooled to 120 DEG C, it is diluted in styrene, it is eventually adding DMA, methyl hydroquinone, phenyl salicylate.
Obtained unsaturated polyester resin:
| 80 DEG C of reactivities | 40 points 13 seconds |
| 80 DEG C of heat stability | 24h |
| 25 DEG C of gel times | 25 points 35 seconds |
| 110 DEG C of heat stability (company standard) | 3 hours gels |
Comparative example 4
The raw material components part by weight of the special unsaturated polyester resin of for shelf-stable cloud stone glue is:
Dicyclopentadiene 110(purity 60%)
Maleic anhydride 85
Phthalic anhydride 125
Water 23
Ethylene glycol 28
Propylene glycol 34
Diethylene glycol: 63
Styrene 90
Adjacent methyl hydroquinone 0.2
N, N-dimethyl-p-toluidine 0.5
Phosphoric acid 0.1
Triphenyl phosphite 1
Titanium dioxide 0.1
By above-mentioned part by weight, dicyclopentadiene, maleic anhydride, water are reacted at 110 DEG C 3h, be subsequently adding phthalic anhydride, ethylene glycol, diethylene glycol, propylene glycol phosphoric acid, triphenyl phosphite, adjacent methyl hydroquinone existence under in 200 DEG C when carry out esterification dehydration, evacuation polycondensation when reaction to acid number is 43mg/KOH, react to acid number 32mg/KOH and release vacuum and be cooled to 120 DEG C, it is diluted in styrene, it is eventually adding N, N-dimethyl-p-toluidine, adjacent methyl hydroquinone, titanium dioxide.
Obtained unsaturated polyester resin:
| 80 DEG C of reactivities | 3 points 13 seconds |
| 80 DEG C of heat stability | 3 days gels |
| 25 DEG C of gel times | 13 points 35 seconds |
| 110 DEG C of heat stability (company standard) | 4.5 hours gels |
Claims (4)
1. the special unsaturated polyester resin of for shelf-stable cloud stone glue, it is characterised in that the weight portion of its constitutive material is:
Dicyclopentadiene 85-115；
Unsaturated dicarboxylic acid anhydride 75-95；
Monounsaturated dicarboxylic acid acid anhydride 100-140；
Water 18-23；
Dihydroxylic alcohols 100-150；
Styrene 90-200；
The weight portion of other materials used is:
Polymerization inhibitor 0.1-0.6；
Accelerator 0.2-1；
Catalyst 0.1-1.5；
Antioxidant 1-2；
Ultraviolet-resistant absorbent 0-0.2.
2. the special unsaturated polyester resin of for shelf-stable cloud stone glue as claimed in claim 1, it is characterised in that the purity of described dicyclopentadiene is 70%-100%.
3. the special unsaturated polyester resin of for shelf-stable cloud stone glue as claimed in claim 1 or 2, it is characterised in that described unsaturated dicarboxylic acid anhydride includes maleic anhydride；Described monounsaturated dicarboxylic acid acid anhydride includes phthalic anhydride；Described saturated dihydroxylic alcohols include ethylene glycol, diethylene glycol, propylene glycol one or more；Described polymerization inhibitor includes adjacent methyl hydroquinone, 2,5 di-tert-butyl hydroquinones, tert-butylhydroquinone, one or more of methyl hydroquinone；Described accelerator includes DMA, N, N-dimethyl-p-toluidine, N, N-diisopropanol para-totuidine, cobalt naphthenate, one or more of cobalt iso-octoate；Described catalyst includes phosphoric acid, phosphorous acid, sulphuric acid, one or more of benzyltriethylammoinium chloride；Described antioxidant includes triphenyl phosphite, NSC 5284, one or more of 2,6 ditertbutylparacresols；Described ultraviolet-resistant absorbent includes titanium dioxide, one or both of phenyl salicylate.
4. the preparation method of the special unsaturated polyester resin of for shelf-stable cloud stone glue as described in as arbitrary in claim 1-3 is: by weight by the dicyclopentadiene of 85-115 part purity 70% ~ 100%, 75-95 part unsaturated dicarboxylic acid anhydride, 18-23 part water, hydrolysis 3h at 110 ~ 115 DEG C, it is subsequently adding 100-140 part monounsaturated dicarboxylic acid acid anhydride, 100-150 part dihydroxylic alcohols is at catalyst, antioxidant, in 130 ~ 200 DEG C when, esterification dehydration is carried out under the existence of polymerization inhibitor, reaction utilizes vacuum pump evacuation polycondensation when being 50-60mg/KOH to acid number, react to acid number 28 ~ 32mg/KOH and release vacuum and be cooled to 120 DEG C, it is diluted in 90-200 part styrene, it is eventually adding accelerator, polymerization inhibitor, ultraviolet-resistant absorbent.
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| CN107177321A (en) * | 2017-06-05 | 2017-09-19 | 苏州金禾新材料股份有限公司 | A kind of disassembled foam double-faced adhesive |
| CN107903386A (en) * | 2017-11-17 | 2018-04-13 | 广东中迅新型材料有限公司 | A kind of modified unsaturated polyester resin and its artificial stone of preparation |
| CN109957098A (en) * | 2017-12-25 | 2019-07-02 | 宜兴市兴南复合材料厂有限公司 | A kind of cloud stone glue special epoxy resin and preparation method |
| CN109232874A (en) * | 2018-08-21 | 2019-01-18 | 江苏金隆新材料有限公司 | Cloud stone glue unsaturated polyester resin of epoxy resin modification and its preparation method and application |
| CN109912953B (en) * | 2019-01-23 | 2021-05-28 | 新阳科技集团有限公司 | Preparation method of terephthalic acid type unsaturated polyester resin |
| CN111205444B (en) * | 2020-03-13 | 2022-05-24 | 广东鲸鲨化工有限公司 | Modified waterborne polyester resin with high dicyclopentadiene content as well as preparation method and application thereof |
| CN115305078B (en) * | 2022-05-23 | 2023-09-19 | 长江大学 | Liquid-solid phase change self-supporting fracturing fluid composition and preparation method thereof |
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